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91-02-1

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91-02-1 Usage

Description

2-Benzoylpyridine is a colorless to slightly yellow crystalline compound that serves as a versatile reagent and precursor in various chemical applications.

Uses

Used in Organic Synthesis:
2-Benzoylpyridine is used as a reagent in organic synthesis, facilitating the formation of complex organic molecules and contributing to the development of new chemical compounds.
Used in Polymers Industry:
In the polymers industry, 2-Benzoylpyridine is used as a reagent to assist crosslinking in acrylic coating compounds. This enhances the properties of the coatings, such as durability, adhesion, and resistance to environmental factors.
Used in Pharmaceutical Research:
2-Benzoylpyridine is a precursor for thioemicarbazone compounds, which exhibit high cytotoxic activity against human leukemia cell lines. This makes it a valuable component in the development of potential anti-cancer drugs.
Additionally, 2-Benzoylpyridine possesses some anti-inflammatory qualities, which can be beneficial in the research and development of medications for inflammatory conditions.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 24, p. 1061, 1987 DOI: 10.1002/jhet.5570240429Tetrahedron Letters, 25, p. 1715, 1984 DOI: 10.1016/S0040-4039(01)81152-7

Purification Methods

Dissolve 2-benzoylpyridine in Et2O, shake it with aqueous NaHCO3, H2O, dry it over MgSO4 and evaporate. The residue solidifies on cooling. The solid can be recrystallised from pet ether. Its hydrochloride crystallises from Me2CO, m 126-127o, and the 2,4-dinitrophenylhydrazone has m 193-195o. It distils at high vacuum. [Kinkerton & Thames J Organomet Chem 24 623 1970, Beilstein 21/8 V 566.]

Check Digit Verification of cas no

The CAS Registry Mumber 91-02-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 1 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 91-02:
(4*9)+(3*1)+(2*0)+(1*2)=41
41 % 10 = 1
So 91-02-1 is a valid CAS Registry Number.
InChI:InChI=1/C12H9NO/c14-12(10-6-2-1-3-7-10)11-8-4-5-9-13-11/h1-9H

91-02-1 Well-known Company Product Price

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  • Alfa Aesar

  • (A10857)  2-Benzoylpyridine, 99%   

  • 91-02-1

  • 50g

  • 351.0CNY

  • Detail
  • Alfa Aesar

  • (A10857)  2-Benzoylpyridine, 99%   

  • 91-02-1

  • 250g

  • 1349.0CNY

  • Detail
  • Alfa Aesar

  • (A10857)  2-Benzoylpyridine, 99%   

  • 91-02-1

  • 1000g

  • 4983.0CNY

  • Detail
  • Aldrich

  • (B14000)  2-Benzoylpyridine  ≥99%

  • 91-02-1

  • B14000-25G

  • 246.87CNY

  • Detail
  • Aldrich

  • (B14000)  2-Benzoylpyridine  ≥99%

  • 91-02-1

  • B14000-100G

  • 683.28CNY

  • Detail

91-02-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Benzoylpyridine

1.2 Other means of identification

Product number -
Other names 2-benzoyl-pyridin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:91-02-1 SDS

91-02-1Synthetic route

phenyl(2-pyridinyl)methanol
31796-72-2

phenyl(2-pyridinyl)methanol

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With butyltriphenylphosphonium chlorochromate In acetonitrile for 0.166667h; Heating;100%
With tert.-butylhydroperoxide; tetrabutyl-ammonium chloride; sodium carbonate; copper dichloride; 2,2′‐biquinoline‐4,4′‐dicarboxylic acid dipotassium salt In water at 40℃; for 48h;100%
With dicarbonyl(cyclopentadienyl)iron(II) chloride; sodium hydride In toluene for 20h; Catalytic behavior; Reagent/catalyst; Temperature; Reflux; Inert atmosphere; Schlenk technique;100%
(1-oxido-2-pyridinyl)phenylmethanone
4789-06-4

(1-oxido-2-pyridinyl)phenylmethanone

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With phosphorus trichloride In chloroform at 0 - 80℃; for 1.16667h;100%
2-Benzylpyridine
101-82-6

2-Benzylpyridine

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With pyridine; tert.-butylhydroperoxide; iodine In water at 80℃; chemoselective reaction;99%
With oxygen In 1,2-dichloro-benzene at 110℃; under 760.051 Torr; for 6h; Schlenk technique;99%
With potassium bromate; cerium(IV) oxide In 1,4-dioxane; water; acetic acid at 95℃; for 4h;95%
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In toluene for 3h;99%
With oxygen; potassium carbonate In water; dimethyl sulfoxide Ambient temperature;48%
With oxygen; sodium hydride 1.) THF, 5 min; Yield given. Multistep reaction;
2-benzoylpyridine phenylhydrazone

2-benzoylpyridine phenylhydrazone

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With benzyltriphenylphosphonium dichromate; silica gel for 0.166667h;98%
With 1-benzyl-4-aza-1-azoniabiyclo<2.2.2>octane peroxodisulfate In acetonitrile for 1h; Heating;96%
With benzyltriphenylphosphonium dichromate In acetonitrile for 0.5h; Oxidation; Heating;96%
2-(1-phenylvinyl)pyridine
15260-65-8

2-(1-phenylvinyl)pyridine

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With oxygen at 110℃; for 8h; Sealed tube;97.3%
With oxygen at 110℃; for 8h; Schlenk technique; Green chemistry;95%
With 1-hydroxy-pyrrolidine-2,5-dione; graphitic carbon nitride; oxygen In acetonitrile at 20℃; Inert atmosphere; Irradiation;75%
phenyl-pyridin-2-yl-methanethione

phenyl-pyridin-2-yl-methanethione

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With 3-carboxypyridinium chlorochromate In acetonitrile for 0.0333333h; Product distribution; Further Variations:; Reagents; Temperatures; without microwave irradiation; solvent-free; microwave irradiation;96%
2-iodopyridine
5029-67-4

2-iodopyridine

carbon monoxide
201230-82-2

carbon monoxide

phenylboronic acid
98-80-6

phenylboronic acid

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With (bis(tricyclohexyl)phosphine)palladium(II) dichloride; potassium carbonate In tetrahydrofuran at 100℃; under 3750.3 Torr; for 20h;95%
Stage #1: 2-iodopyridine; phenylboronic acid With potassium carbonate In toluene for 0.166667h; Suzuki cross-coupling reaction; Autoclave;
Stage #2: carbon monoxide In toluene at 100℃; under 10343.2 Torr; for 10h; Suzuki cross-coupling reaction; Autoclave;
89%
With Bedford’s palladacycle; potassium carbonate; methoxybenzene at 120℃; under 3750.38 Torr; for 12h; Suzuki-Miyaura Coupling; Autoclave;89%
2-Benzylpyridine
101-82-6

2-Benzylpyridine

A

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

B

[18O]-2-benzoylpyridine

[18O]-2-benzoylpyridine

Conditions
ConditionsYield
With N-Bromosuccinimide; (18O)-dimethylsulfoxide at 20 - 120℃; for 24h; Reagent/catalyst; Inert atmosphere; Schlenk technique;A n/a
B 95%
2-(2-phenyl-[1,3]dithian-2-yl)-pyridine

2-(2-phenyl-[1,3]dithian-2-yl)-pyridine

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With bismuth(III) chloride; benzyltriphenylphosphonium peroxymonosulfate In acetonitrile for 3h; Heating;94%
2-bis(methylthio)phenylmethylpyridine
950993-49-4

2-bis(methylthio)phenylmethylpyridine

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With calcium carbonate; mercury dichloride In water; acetonitrile at 20℃;93%
phenylglyoxylyl chloride
25726-04-9

phenylglyoxylyl chloride

2-trimethylstannylpyridine
13737-05-8

2-trimethylstannylpyridine

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
In benzene for 0.5h; Ambient temperature;91%
(3,3-Dichloro-3,4,5,6-tetrahydro-pyridin-2-yl)-phenyl-methanone
176173-93-6

(3,3-Dichloro-3,4,5,6-tetrahydro-pyridin-2-yl)-phenyl-methanone

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran for 3h; Heating;90%
(E)-2-pyridylphenyl ketoxime
14178-31-5

(E)-2-pyridylphenyl ketoxime

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With iron(III) chloride In N,N-dimethyl-formamide at 25℃; for 0.5h; sonication;90%
2-iodopyridine
5029-67-4

2-iodopyridine

benzoic acid
65-85-0

benzoic acid

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
Stage #1: benzoic acid With isopropylmagnesium bromide In tetrahydrofuran; 2-methyltetrahydrofuran at 15℃; Inert atmosphere; Cooling with ice;
Stage #2: 2-iodopyridine In tetrahydrofuran; 2-methyltetrahydrofuran Inert atmosphere;
Stage #3: With TurboGrignard In tetrahydrofuran; 2-methyltetrahydrofuran for 0.166667h; Reagent/catalyst; Inert atmosphere;
88%
phenylglyoxylyl chloride
25726-04-9

phenylglyoxylyl chloride

2-tri-n-butylstannylpyridine
17997-47-6

2-tri-n-butylstannylpyridine

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
In benzene for 0.5h; Ambient temperature;87%
carbon monoxide
201230-82-2

carbon monoxide

toluene-4-sulfonic acid phenyl ester
640-60-8

toluene-4-sulfonic acid phenyl ester

pyridin-2-ylboronic acid
197958-29-5

pyridin-2-ylboronic acid

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With palladium(II) trifluoroacetate; 1,2-bis-(diphenylphosphino)ethane In N,N-dimethyl acetamide at 80℃; under 760.051 Torr; for 6h; Suzuki-Miyaura Coupling;87%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

N-methoxy-N-methylcyanoformamide

N-methoxy-N-methylcyanoformamide

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
Stage #1: 2-bromo-pyridine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Weinreb Ketone Synthesis;
Stage #2: N-methoxy-N-methylcyanoformamide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.33h; Weinreb Ketone Synthesis;
Stage #3: phenylmagnesium bromide In tetrahydrofuran; hexane at -78℃; for 0.333333h;
86%
2-iodopyridine
5029-67-4

2-iodopyridine

benzaldehyde
100-52-7

benzaldehyde

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With caesium carbonate In 1,4-dioxane for 12h; Reflux;86%
2-Benzylpyridine
101-82-6

2-Benzylpyridine

acetic acid
64-19-7

acetic acid

A

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

B

phenyl(pyridin-2-yl)methyl acetate
74031-79-1

phenyl(pyridin-2-yl)methyl acetate

Conditions
ConditionsYield
Stage #1: 2-Benzylpyridine; acetic acid With iodine for 0.0833333h;
Stage #2: With tert.-butylhydroperoxide In decane at 20 - 100℃; for 1.5h; Reagent/catalyst; Solvent; Temperature;
A 10%
B 85%
With copper(l) iodide; oxygen; palladium diacetate at 120℃; for 24h; Autoclave;
2-oxo-2-(pyridin-2-yl)acetic acid

2-oxo-2-(pyridin-2-yl)acetic acid

phenylboronic acid
98-80-6

phenylboronic acid

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With silver carbonate In acetonitrile at 60℃; for 1h;85%
pyridin-2-yl trifluoromethanesulfonate
65007-00-3

pyridin-2-yl trifluoromethanesulfonate

carbon monoxide
201230-82-2

carbon monoxide

phenylboronic acid
98-80-6

phenylboronic acid

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium(II) trifluoroacetate In tert-butyl methyl ether at 80℃; under 760.051 Torr; for 6h; Suzuki-Miyaura Coupling;85%
carbon monoxide
201230-82-2

carbon monoxide

Phenyl triflate
17763-67-6

Phenyl triflate

pyridin-2-ylboronic acid
197958-29-5

pyridin-2-ylboronic acid

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium(II) trifluoroacetate In tert-butyl methyl ether at 80℃; under 760.051 Torr; for 6h; Suzuki-Miyaura Coupling;85%
pyridine
110-86-1

pyridine

benzyl alcohol
100-51-6

benzyl alcohol

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With dipotassium peroxodisulfate In water at 120℃; for 18h; Green chemistry; regioselective reaction;85%
pyridine N-oxide
694-59-7

pyridine N-oxide

phenylacetylene
536-74-3

phenylacetylene

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With dipotassium peroxodisulfate; water; silver nitrate at 20℃; Reagent/catalyst;85%
With tetrafluoroboric acid; oxygen; 9-(2-mesityl)-10-methylacridinium perchlorate In acetonitrile at 50℃; for 12h; Schlenk technique; Irradiation;60%
2-iodopyridine
5029-67-4

2-iodopyridine

chloroform
67-66-3

chloroform

phenylboronic acid
98-80-6

phenylboronic acid

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With C33H27N2O3PPd; potassium hydroxide In toluene at 80℃; Suzuki-Miyaura Coupling; Sealed tube;85%
pyridine N-oxide
694-59-7

pyridine N-oxide

silver phenylacetylide
33440-88-9

silver phenylacetylide

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With dipotassium peroxodisulfate; water at 20℃; Reagent/catalyst;84%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

benzoic acid
65-85-0

benzoic acid

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
Stage #1: benzoic acid With isopropylmagnesium bromide In tetrahydrofuran; 2-methyltetrahydrofuran at 15℃; Inert atmosphere; Cooling with ice;
Stage #2: 2-bromo-pyridine In tetrahydrofuran; 2-methyltetrahydrofuran Inert atmosphere;
Stage #3: With TurboGrignard In tetrahydrofuran; 2-methyltetrahydrofuran for 4h; Inert atmosphere;
83%
2-Cyanopyridine
100-70-9

2-Cyanopyridine

bromobenzene
108-86-1

bromobenzene

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
Stage #1: bromobenzene With iodine; magnesium In tetrahydrofuran
Stage #2: 2-Cyanopyridine In tetrahydrofuran at 0℃;
82%
Stage #1: 2-Cyanopyridine; bromobenzene With magnesium In tetrahydrofuran at 0℃;
Stage #2: With ammonium chloride In tetrahydrofuran
Stage #1: bromobenzene With iodine; magnesium In tetrahydrofuran
Stage #2: 2-Cyanopyridine In tetrahydrofuran at 0℃;
Stage #1: bromobenzene With iodine; magnesium In tetrahydrofuran at 20℃; Cooling;
Stage #2: 2-Cyanopyridine In tetrahydrofuran at 0 - 20℃;
Stage #3: With hydrogenchloride; water In diethyl ether for 0.5h;
Stage #1: bromobenzene With iodine; magnesium In tetrahydrofuran Inert atmosphere;
Stage #2: 2-Cyanopyridine In tetrahydrofuran at 0℃; Inert atmosphere;
Stage #3: With water; ammonium chloride In tetrahydrofuran
phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

phenyl(2-pyridinyl)methanol
31796-72-2

phenyl(2-pyridinyl)methanol

Conditions
ConditionsYield
With magnesium(II) perchlorate; polymer-bound NADH (2a) In acetonitrile; benzene at 80℃; for 120h; Further byproducts given;100%
With hydrogen; silver perchlorate; potassium hexamethylsilazane In toluene at 25℃; under 15001.5 Torr; for 17h; Reagent/catalyst; Glovebox;99%
With sodium tetrahydroborate In methanol at 10 - 20℃; for 1.5h;97%
phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

methylamine
74-89-5

methylamine

N-[phenyl(pyridin-2-yl)methylene]methanamine
1182372-35-5

N-[phenyl(pyridin-2-yl)methylene]methanamine

Conditions
ConditionsYield
In methanol at 20℃; for 24h;100%
In methanol for 7h; Reflux;
phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

2-benzylpiperidine
32838-55-4

2-benzylpiperidine

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen; acetic acid at 20℃; under 760.051 Torr; for 8h;100%
Multi-step reaction with 2 steps
1: acetic acid; platinum on carbon; hydrogen / 6 h / 1551.49 - 2068.65 Torr
2: acetic acid; perchloric acid; platinum on carbon; hydrogen / 72 h / 50 - 55 Torr
View Scheme
phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

benzylamine
100-46-9

benzylamine

1-phenyl-3-phenylimidazo[1,5-a]pyridine
79159-65-2

1-phenyl-3-phenylimidazo[1,5-a]pyridine

Conditions
ConditionsYield
With iodine; sodium acetate In 1,2-dichloro-ethane for 5.5h; Solvent; Reagent/catalyst; Temperature; Reflux;99%
With copper(II) acetate monohydrate In N,N-dimethyl-formamide at 110℃; for 8h; Reagent/catalyst; Temperature; Solvent;93%
Stage #1: phenyl(pyridin-2-yl)methanone With manganese(IV) oxide; toluene-4-sulfonic acid at 20℃; for 0.25h; Inert atmosphere;
Stage #2: benzylamine at 170℃; for 5.5h; Temperature; Inert atmosphere; Microwave irradiation;
72%
phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

1,1,1-trifluoroacetophenone
434-45-7

1,1,1-trifluoroacetophenone

2,2,2-trifluoro-1-phenyl-1-(pyridin-2-yl)ethanol

2,2,2-trifluoro-1-phenyl-1-(pyridin-2-yl)ethanol

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 0.333333h;99%
phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

(R)-(-)-α-phenyl-2-pyridylmethanol
5583-33-5

(R)-(-)-α-phenyl-2-pyridylmethanol

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C39H45FeN2O2PS; hydrogen; lithium tert-butoxide In isopropyl alcohol at 25 - 30℃; under 22502.3 Torr; for 12h; Reagent/catalyst; Autoclave; enantioselective reaction;99%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C37H41FeN2O2PS; hydrogen; lithium tert-butoxide In methanol at 40℃; under 22502.3 Torr; for 12h; Reagent/catalyst; Solvent; Temperature; Pressure; Autoclave; enantioselective reaction;97%
With C36H40Cl2N2P2Ru; potassium tert-butylate In dichloromethane; isopropyl alcohol at 23℃; for 2h; enantioselective reaction;92%
phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

(S)-(+)-α-phenyl-2-pyridylmethanol
5583-33-5, 14159-57-0, 31796-72-2, 5583-34-6

(S)-(+)-α-phenyl-2-pyridylmethanol

Conditions
ConditionsYield
With C60H60P2Rh(1+)*BF4(1-); hydrogen In dichloromethane at 20℃; under 6080.41 Torr; for 24h; Autoclave; enantioselective reaction;99%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C43H53FeN2O2PS; hydrogen; lithium tert-butoxide In isopropyl alcohol at 25 - 30℃; under 22502.3 Torr; for 12h; Catalytic behavior; Temperature; Reagent/catalyst; Solvent; Autoclave; enantioselective reaction;99%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C37H41FeN2O2PS; hydrogen; lithium tert-butoxide In methanol at 40℃; under 22502.3 Torr; for 12h; Reagent/catalyst; Pressure; Solvent; Temperature; Autoclave; enantioselective reaction;97%
phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

[tin(II)(CH(CMeN(2,6-iPr2C6H3)2)2(hydrido)]
888939-69-3

[tin(II)(CH(CMeN(2,6-iPr2C6H3)2)2(hydrido)]

[tin(II)(CH(CMeN(2,6-iPr2C6H3))2)(OCH(Ph)(2-Py))]
1138335-32-6

[tin(II)(CH(CMeN(2,6-iPr2C6H3))2)(OCH(Ph)(2-Py))]

Conditions
ConditionsYield
In toluene treatment of tin complex with 2-benzoylpyridine;99%
phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

para-methylbenzylamine
104-84-7

para-methylbenzylamine

1-phenyl-3-(p-tolyl)imidazo[1,5-a]pyridine

1-phenyl-3-(p-tolyl)imidazo[1,5-a]pyridine

Conditions
ConditionsYield
With iodine; sodium acetate In 1,2-dichloro-ethane for 2h; Solvent; Reflux;99%
With copper(II) acetate monohydrate In N,N-dimethyl-formamide at 110℃; for 8h;93%
phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

para-fluorobenzylamine
140-75-0

para-fluorobenzylamine

3-(4-fluorophenyl)-1-(phenyl)imidazo[1,5-a]pyridine

3-(4-fluorophenyl)-1-(phenyl)imidazo[1,5-a]pyridine

Conditions
ConditionsYield
With iodine; sodium acetate In 1,2-dichloro-ethane for 4h; Reflux;99%
With copper(II) acetate monohydrate In N,N-dimethyl-formamide at 110℃; for 8h;91%
Stage #1: phenyl(pyridin-2-yl)methanone With manganese(IV) oxide; toluene-4-sulfonic acid at 20℃; for 0.25h; Inert atmosphere;
Stage #2: para-fluorobenzylamine at 170℃; for 5.5h; Inert atmosphere; Microwave irradiation;
65%
phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

(naphth-1-yl)methylamine
118-31-0

(naphth-1-yl)methylamine

3-(naphthalen-1-yl)-1-phenylimidazo[1,5-a]pyridine

3-(naphthalen-1-yl)-1-phenylimidazo[1,5-a]pyridine

Conditions
ConditionsYield
With iodine; sodium acetate In 1,2-dichloro-ethane for 6h; Reflux;99%
With copper(II) acetate monohydrate In N,N-dimethyl-formamide at 110℃; for 8h;90%
(2-aminomethylpyridine)
3731-51-9

(2-aminomethylpyridine)

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

1-phenyl-3-(pyridin-2-yl)imidazo[1,5-a]pyridine
1346167-09-6

1-phenyl-3-(pyridin-2-yl)imidazo[1,5-a]pyridine

Conditions
ConditionsYield
With iodine; sodium acetate In 1,2-dichloro-ethane for 2h; Reflux;99%
Stage #1: phenyl(pyridin-2-yl)methanone With manganese(IV) oxide; toluene-4-sulfonic acid at 20℃; for 0.25h; Inert atmosphere;
Stage #2: 2-(Aminomethyl)pyridine at 170℃; for 5.5h; Inert atmosphere; Microwave irradiation;
41%
With copper(II) acetate monohydrate In N,N-dimethyl-formamide at 110℃; for 8h;31%
phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

2-(1-phenylvinyl)pyridine
15260-65-8

2-(1-phenylvinyl)pyridine

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h;
Stage #2: phenyl(pyridin-2-yl)methanone In tetrahydrofuran at 50℃; for 1h;
99%
With potassium tert-butylate In tetrahydrofuran Inert atmosphere;50%
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Wittig Olefination; Schlenk technique; Inert atmosphere;
Stage #2: phenyl(pyridin-2-yl)methanone In tetrahydrofuran at 50℃; Wittig Olefination; Schlenk technique; Inert atmosphere;
40%
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 1h;21%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃;
Stage #2: phenyl(pyridin-2-yl)methanone In tetrahydrofuran; hexane at 20℃; for 12h;
2.18 g
phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

alpha-phenyl-2-piperidinemethanol
23702-98-9

alpha-phenyl-2-piperidinemethanol

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethyl [2]alcohol at 60℃; under 15001.5 Torr; for 6h;98%
With platinum on carbon; hydrogen; acetic acid under 1551.49 - 2068.65 Torr; for 6h;80%
With hydrogenchloride; hydrogen; platinum(IV) oxide In ethanol under 41253.3 Torr; for 10h;100 % Spectr.
phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

tert-butyl 3-hydroxy-3-phenyl-3-(pyridin-2-yl)propionate

tert-butyl 3-hydroxy-3-phenyl-3-(pyridin-2-yl)propionate

Conditions
ConditionsYield
Stage #1: With pyridine; cinchonine In tetrahydrofuran at 0℃; for 0.5h; Reformatsky Reaction;
Stage #2: phenyl(pyridin-2-yl)methanone In tetrahydrofuran at -40℃; for 4h;
98%
phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

terephthalaldehyde,
623-27-8

terephthalaldehyde,

C32H22N4

C32H22N4

Conditions
ConditionsYield
With ammonium acetate; acetic acid at 118℃; for 12h;98%
phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

4-phenylsemicarbazide hydrochloride
5441-14-5

4-phenylsemicarbazide hydrochloride

C19H16N4O*ClH

C19H16N4O*ClH

Conditions
ConditionsYield
In ethanol for 6h; Reflux;98%
phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

methyllithium
917-54-4

methyllithium

1-phenyl-1-(pyridin-2-yl)ethanol
19490-92-7

1-phenyl-1-(pyridin-2-yl)ethanol

Conditions
ConditionsYield
In diethyl ether at -78 - 20℃; for 1h; Schlenk technique; Inert atmosphere;97%
phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

methyllithium
917-54-4

methyllithium

A

2-(pyridine-2-yl)propan-2-ol
37988-38-8

2-(pyridine-2-yl)propan-2-ol

B

1-phenyl-1-(pyridin-2-yl)ethanol
19490-92-7

1-phenyl-1-(pyridin-2-yl)ethanol

Conditions
ConditionsYield
In diethyl ether at -78 - 20℃; for 1.25h;A 55%
B 97%
phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

3-methyl-benzenemethanamine
100-81-2

3-methyl-benzenemethanamine

1-phenyl-3-(m-tolyl)imidazo[1,5-a]pyridine

1-phenyl-3-(m-tolyl)imidazo[1,5-a]pyridine

Conditions
ConditionsYield
With iodine; sodium acetate In 1,2-dichloro-ethane for 5h; Reflux;97%
With copper(II) acetate monohydrate In N,N-dimethyl-formamide at 110℃; for 8h;93%
phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

diethyl cyanophosphonate
2942-58-7

diethyl cyanophosphonate

lithium cyanide
2408-36-8

lithium cyanide

cyano-phenyl-(pyridin-2-yl)methyl diethylphosphate

cyano-phenyl-(pyridin-2-yl)methyl diethylphosphate

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 0.0833333h;97%
phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Diphenylphosphine oxide
4559-70-0

Diphenylphosphine oxide

(diphenylphosphoryl)(phenyl)pyridine-2-ylmethanol

(diphenylphosphoryl)(phenyl)pyridine-2-ylmethanol

Conditions
ConditionsYield
In neat (no solvent) at 60 - 62℃; for 0.25h; Temperature; Inert atmosphere; Green chemistry;97%
phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

acrylonitrile
107-13-1

acrylonitrile

4-hydroxy-4-phenyl-4-(pyridin-2-yl)butanenitrile

4-hydroxy-4-phenyl-4-(pyridin-2-yl)butanenitrile

Conditions
ConditionsYield
With ammonia; water; zinc In acetonitrile at 20℃; under 760.051 Torr; for 20h; Sealed tube;96%

91-02-1Relevant articles and documents

Ruthenium-catalyzed meta -C-H bond alkylation of aryl 2-pyridyl ketones

Li, Gang,Jia, Chunqi,Cai, Xiaofeng,Zhong, Lei,Zou, Lei,Cui, Xiuling

, p. 293 - 296 (2019)

The first example of meta-selective CAr-H bond functionalization of aryl 2-pyridyl ketones has been developed using [Ru(p-cymene)Cl2]2 as the catalyst and alkyl bromide as the coupling reagent. This development provides an efficient strategy for modifying the meta-position of aryl 2-pyridyl ketone skeletons, which are found in various functional molecules.

Poly(ethylene glycol) dimethyl ether mediated oxidative scission of aromatic olefins to carbonyl compounds by molecular oxygen

Yu, Tao,Guo, Mingqing,Wen, Simiaomiao,Zhao, Rongrong,Wang, Jinlong,Sun, Yanli,Liu, Qixing,Zhou, Haifeng

, p. 13848 - 13852 (2021/04/22)

A simple, and practical oxidative scission of aromatic olefins to carbonyl compounds using O2as the sole oxidant with poly(ethylene glycol) dimethyl ether as a benign solvent has been developed. A wide range of monosubstituted,gem-disubstituted, 1,2-disubstituted, trisubstituted and tetrasubstituted aromatic olefins was successfully converted into the corresponding aldehydes and ketones in excellent yields even with gram-scale reaction. Some control experiments were also conducted to support a possible reaction pathway.

Photo-induced oxidative cleavage of C-C double bonds for the synthesis of biaryl methanoneviaCeCl3catalysis

Xie, Pan,Xue, Cheng,Du, Dongdong,Shi, SanShan

supporting information, p. 6781 - 6785 (2021/08/20)

A Ce-catalyzed strategy is developed to produce biaryl methanonesviaphotooxidative cleavage of C-C double bonds at room temperature. This reaction is performed under air and demonstrates high activity as well as functional group tolerance. A synergistic Ce/ROH catalytic mechanism is also proposed based on the experimental observations. This protocol should be the first successful Ce-catalyzed photooxidation reaction of olefins with air as the oxidant, which would provide inspiration for the development of novel Ce-catalyzed photochemical synthesis processes.

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