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540-88-5

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540-88-5 Usage

Chemical Properties

tert-Butyl acetate or t-butyl acetate is a colorless flammable liquid with a camphoror blueberry-like smell. It is used as a solvent in the production of lacquers, enamels, inks, adhesives, thinners, and industrial cleaners. It is also used as an additive to improve the antiknock properties of motor fuels. tert-Butyl acetate has three isomers: n-butyl acetate, isobutyl acetate, and sec-butyl acetate.

Physical properties

Colorless liquid with a fruity odor. Odor threshold concentration in water is 4 ppm (CHRIS, 1994). Nagata and Takeuchi (1990) reported an odor threshold concentration of 71 ppbv.

Uses

tert-Butyl acetate is common industrial solvent used in the making of lacquers, artificial leather, airplane dope, perfume, and as a food additive.

Production Methods

tert-Butyl acetate is prepared from isobutylene reacting with acetic acid in the liquid phase with vanadium pentoxideimpregnated silica as the catalyst and with heat to increase the yield .

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 3, p. 142, 1955Synthesis, p. 1015, 1987Tetrahedron Letters, 37, p. 4555, 1996 DOI: 10.1016/0040-4039(96)00902-1

General Description

Tert-butyl acetate is a colorless liquid with a mild odor. Floats on water. Produces irritating vapor. (USCG, 1999)

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

tert-Butyl acetate is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. tert-Butyl acetate is incompatible with the following: Nitrates; strong oxidizers, alkalis & acids .

Hazard

Flammable, moderate fire risk. Eye and upper respiratory tract irritant.

Health Hazard

Exposure to tert-butyl acetate causes eye, skin, and respiratory irritation in workers. By analogy with the effects of exposure to similar esters, tert-butyl acetate may act as a CNS depressant at high concentrations. The signs and symptoms of acute exposure to tert-butyl acetate include, but are not limited to, itchy or inflamed eyes and irritation of the nose and upper respiratory tract. Exposures to tert-butyl acetate at high concentrations may cause headache, drowsiness, and other narcotic effects.

Safety Profile

Poison by inhalation and ingestion. Flammable. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

Environmental fate

Chemical/Physical. Hydrolyzes in water to tert-butyl alcohol and acetic acid. The estimated hydrolysis half-life at 25 °C and pH 7 is 140 yr (Mabey and Mill, 1978).

storage

tert-Butyl acetate should be stored in a cool, dry, well-ventilated area in tightly sealed containers that are labeled in accordance with regulatory standards. Containers of tert butyl acetate should be protected from physical damage and should be stored separately from nitrates, strong oxidizers, strong acids, strong alkalis, heat, sparks, and open flame. Because containers that formerly contained tert-butyl acetate may still hold product resi dues, they should be handled appropriately

Purification Methods

Wash the ester with 5% Na2CO3 solution, then saturated aqueous CaCl2, dry with CaSO4 and distil it. [McClosky et al. Org Synth Coll Vol IV 263 1963, Mangia et al. Org Prep Proc Int 18 13 1986, Beilstein 2 IV 151.]

Precautions

If exposures to tert-butyl acetate or a solution in work areas gets into the eyes, immediately fl ush the eyes with large amounts of water for a minimum of 15 min, lifting the lower and upper lids occasionally. Always use safety goggles or eye protection in combination with breathing protection.

Check Digit Verification of cas no

The CAS Registry Mumber 540-88-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,4 and 0 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 540-88:
(5*5)+(4*4)+(3*0)+(2*8)+(1*8)=65
65 % 10 = 5
So 540-88-5 is a valid CAS Registry Number.
InChI:InChI=1/C6H12O2/c1-5(7)8-6(2,3)4/h1-4H3

540-88-5 Well-known Company Product Price

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  • Alfa Aesar

  • (L08855)  tert-Butyl acetate, 99%   

  • 540-88-5

  • 50g

  • 197.0CNY

  • Detail
  • Alfa Aesar

  • (L08855)  tert-Butyl acetate, 99%   

  • 540-88-5

  • 250g

  • 530.0CNY

  • Detail
  • Alfa Aesar

  • (L08855)  tert-Butyl acetate, 99%   

  • 540-88-5

  • 1000g

  • 1658.0CNY

  • Detail

540-88-5SDS

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 tert-Butyl acetate

1.2 Other means of identification

Product number -
Other names tert-butyl N-acetate

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:540-88-5 SDS

540-88-5Synthetic route

acetic anhydride
108-24-7

acetic anhydride

tert-butyl alcohol
75-65-0

tert-butyl alcohol

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

Conditions
ConditionsYield
at 200℃; under 22502.3 Torr; for 0.166667h; Product distribution / selectivity;100%
With Cp2Ti(OSO2C8F17)2 at 100℃; for 0.0833333h; Neat (no solvent);99%
With bismuth(lll) trifluoromethanesulfonate In acetonitrile at 20℃; for 0.166667h;98%
3,3-dimethyl-butan-2-one
75-97-8

3,3-dimethyl-butan-2-one

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

Conditions
ConditionsYield
With N-hydroxyphthalimide; oxygen; benzaldehyde In 1,2-dichloro-ethane at 40℃; for 18h; Baeyer-Villiger Ketone Oxidation;99.3%
With Oxone at 40℃; for 8h; Baeyer-Villiger oxidation; Ionic liquid;88%
With oxygen; benzaldehyde; nickel(II) iodide; Dowex 50W; iron(II) In 1,2-dichloro-ethane at 20℃; for 15h; Baeyer-Villiger oxidation;52%
acetyl chloride
75-36-5

acetyl chloride

tert-butyl alcohol
75-65-0

tert-butyl alcohol

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

Conditions
ConditionsYield
In dichloromethane at 20℃; for 24h;98%
zirconium(IV) oxychloride at 20℃; for 0.0666667h;96%
bismuth(III) oxychloride at 20℃; for 0.0666667h;96%
tertiary butyl chloride
507-20-0

tertiary butyl chloride

acetic acid
64-19-7

acetic acid

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

Conditions
ConditionsYield
With calcined zinc oxide; acetic anhydride at 15℃; for 0.5h;96%
tert-butyl peroxyacetate
107-71-1

tert-butyl peroxyacetate

triphenylantimony
603-36-1

triphenylantimony

A

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

B

triphenylantimony diacetate

triphenylantimony diacetate

Conditions
ConditionsYield
With water; acetic anhydride In tetrahydrofuran; toluene byproducts: tert-butanol, phenol; toluene soln. of peracetate, acetic anhydride, and Sb-compd. heating in evacuated tube (70°C, 35 h), liquid fraction condensing in cold trap, THF+H2O addn., liquid fraction condensing; solid residue extracting by hexane (removing SbPh3) and CHCl3 (product);elem. anal.;A n/a
B 94%
tert-butoxytrimethylsilane
13058-24-7

tert-butoxytrimethylsilane

acetic anhydride
108-24-7

acetic anhydride

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

Conditions
ConditionsYield
at 20℃; for 0.666667h;93%
Ethyl tert-butyl ether
637-92-3

Ethyl tert-butyl ether

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

Conditions
ConditionsYield
With manganese (VII)-oxide In tetrachloromethane; acetone at -45℃;92%
With sodium hypochlorite; cis-{RuCl2(Me2SO)4} In dichloromethane at 20℃; for 5h; pH=9.5;
With sodium hypochlorite; cis-Ru(dmso)2Cl2 In dichloromethane at 20℃; for 5h; pH=9.5; Product distribution; Further Variations:; Catalysts; Solvents;73 % Chromat.
acetic acid
64-19-7

acetic acid

tert-butyl alcohol
75-65-0

tert-butyl alcohol

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate for 1.41667h; Heating;84%
With sulfuric acid; silica gel In hexane for 0.833333h; Heating;82%
With silica gel In dichloromethane for 4h; Ambient temperature;80%
acetyl chloride
75-36-5

acetyl chloride

tert-butyl alcohol
75-65-0

tert-butyl alcohol

A

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

B

tertiary butyl chloride
507-20-0

tertiary butyl chloride

Conditions
ConditionsYield
In dichloromethane 1.) 0 deg C, 2.) room temperature, 1 h; Yield given;A n/a
B 81%
In dichloromethane for 1h; Rate constant; Mechanism; Ambient temperature; further solvents and times; further alcohols;
tert-butyl alcohol
75-65-0

tert-butyl alcohol

A

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

B

tertiary butyl chloride
507-20-0

tertiary butyl chloride

Conditions
ConditionsYield
With acetyl chloride In dichloromethane for 1h; 0 deg C -> room temperature; Yields of byproduct given;A n/a
B 81%
Acetic acid 3-tert-butylperoxy-2,3-dimethyl-4-oxo-3,4-dihydro-naphthalen-1-yl ester
96503-20-7

Acetic acid 3-tert-butylperoxy-2,3-dimethyl-4-oxo-3,4-dihydro-naphthalen-1-yl ester

A

1a,7a-dimethylnaphtho[2,3-b]oxirene-2,7(1aH,7aH)-dione
53948-58-6

1a,7a-dimethylnaphtho[2,3-b]oxirene-2,7(1aH,7aH)-dione

B

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

Conditions
ConditionsYield
zinc trifluoromethanesulfonate In chloroform for 48h; Ambient temperature;A 80%
B 46%
Isopropenyl acetate
108-22-5

Isopropenyl acetate

tert-butyl alcohol
75-65-0

tert-butyl alcohol

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

Conditions
ConditionsYield
With iodine at 85 - 90℃; for 0.0833333h;75%
meta-fluoroaniline
372-19-0

meta-fluoroaniline

bromoacetic acid tert-butyl ester
5292-43-3

bromoacetic acid tert-butyl ester

7-fluoro-4-[2-[4-(thieno[3,2-c]pyridin-4-yl)piperazin-1-yl]ethyl]quinolin-2(1H)-one
189003-71-2

7-fluoro-4-[2-[4-(thieno[3,2-c]pyridin-4-yl)piperazin-1-yl]ethyl]quinolin-2(1H)-one

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

Conditions
ConditionsYield
With tetrabutylammomium bromide In tetrahydrofuran; dichloromethane75%
acetic acid 1-(2,5-dichloro-phenyl)-2,2-bis-methylsulfanyl-vinyl ester
243990-72-9

acetic acid 1-(2,5-dichloro-phenyl)-2,2-bis-methylsulfanyl-vinyl ester

tert-butyl alcohol
75-65-0

tert-butyl alcohol

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: tert-butyl alcohol With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 0.25h; Metallation;
Stage #2: acetic acid 1-(2,5-dichloro-phenyl)-2,2-bis-methylsulfanyl-vinyl ester In tetrahydrofuran; hexane for 1h; Acetylation; Heating;
74%
tert-butyl peroxyacetate
107-71-1

tert-butyl peroxyacetate

triphenylbismuthane
603-33-8

triphenylbismuthane

A

triphenylbismuthine diacetate

triphenylbismuthine diacetate

B

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

Conditions
ConditionsYield
With water; acetic anhydride In tetrahydrofuran; toluene byproducts: tert-butanol, phenol, phenylacetate; toluene soln. of peracetate, acetic anhydride, and Bi-compd. heating (evacuated tube, 70°C, 35 h), liquid fraction condensing in cold trap (liquid N2), THF+H2O addn., liquid fraction condensing; solid residue extracting by hexane (removing BiPh3) and CHCl3 (product);elem. anal.;A 59%
B 72%
With water In tetrahydrofuran; toluene byproducts: tert-butanol, tert-butoxyphenol, phenol; toluene soln. of peracetate and Bi-compd. (evacuated tube), liquid fraction condensing in cold trap, THF+H2O addn., liquid fraction condensing; solid residue extracting by hexane (removing BiPh3) and CHCl3 (product);A 32%
B 24%
acetic acid methyl ester
79-20-9

acetic acid methyl ester

potassium tert-butylate
865-47-4

potassium tert-butylate

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

Conditions
ConditionsYield
In diethyl ether at 20℃;69%
ethyl acetate
141-78-6

ethyl acetate

tert-butyl alcohol
75-65-0

tert-butyl alcohol

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

Conditions
ConditionsYield
phosphotungstic acid at 65 - 70℃; for 1h;62%
K2CO3 + 5percent Carbowax 6000 at 170℃; Product distribution;
tertiary butyl chloride
507-20-0

tertiary butyl chloride

zinc diacetate
557-34-6

zinc diacetate

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

Conditions
ConditionsYield
With potassium carbonate; tetraoctyl ammonium bromide In chloroform for 0.25h; sonicated;60%
With pyridine In benzene at 80℃; for 18h;33%
t-butyl bromide
507-19-7

t-butyl bromide

zinc diacetate
557-34-6

zinc diacetate

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

Conditions
ConditionsYield
With pyridine In benzene at 80℃; for 2h;50%
t-butyl bromide
507-19-7

t-butyl bromide

sodium acetate
127-09-3

sodium acetate

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

Conditions
ConditionsYield
With polyethylene glycol 400 at 65 - 70℃; for 7h;41%
tert-Butyl 2,4-dinitro-3-(n-propylamino)-6-(trifluoromethyl)phenyl trithiocarbonate
74512-00-8

tert-Butyl 2,4-dinitro-3-(n-propylamino)-6-(trifluoromethyl)phenyl trithiocarbonate

A

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

B

4-(n-propylamino)-5-nitro-7-(trifluoromethyl)-1,3-benzodithiole-2-thione
74512-01-9

4-(n-propylamino)-5-nitro-7-(trifluoromethyl)-1,3-benzodithiole-2-thione

Conditions
ConditionsYield
With acetic acid at 110 - 115℃; for 1.33333h;A 40%
B 38%
carbon disulfide
75-15-0

carbon disulfide

vinyl acetate
108-05-4

vinyl acetate

potassium tert-butylate
865-47-4

potassium tert-butylate

methyl iodide
74-88-4

methyl iodide

A

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

B

3,3-bis(methylthio)acrylaldehyde
78263-38-4

3,3-bis(methylthio)acrylaldehyde

Conditions
ConditionsYield
Stage #1: vinyl acetate; potassium tert-butylate In tetrahydrofuran at -78℃; Metallation; Substitution;
Stage #2: carbon disulfide In tetrahydrofuran at 0℃; for 0.75h; Addition;
Stage #3: methyl iodide In tetrahydrofuran at 0℃; for 12h; Methylation;
A n/a
B 40%
Isobutane
75-28-5

Isobutane

acetic acid
64-19-7

acetic acid

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

Conditions
ConditionsYield
With cobalt acetate; iodine; oxygen; N–hydroxysaccharin; sodium nitrite at 60℃; under 8250.83 Torr; for 6h; Temperature; Pressure; Reagent/catalyst; Concentration;35.9%
ortho-methylphenyl iodide
615-37-2

ortho-methylphenyl iodide

tert-Butyl acrylate
1663-39-4

tert-Butyl acrylate

N-(2-bromophenyl)-2,2,2-trifluoroacetamide
2727-71-1

N-(2-bromophenyl)-2,2,2-trifluoroacetamide

A

7-methylphenanthridine
34635-71-7

7-methylphenanthridine

B

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

C

5,6-dihydro-6-t-butoxycarbonylmethyl-7-methylphenanthridine
1238735-10-8

5,6-dihydro-6-t-butoxycarbonylmethyl-7-methylphenanthridine

Conditions
ConditionsYield
With norborn-2-ene; palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 105℃; for 24h; Inert atmosphere; chemoselective reaction;A 35%
B 32 %Chromat.
C 10%
methyl (E)-4-bromo-2-pentenoate
27830-44-0

methyl (E)-4-bromo-2-pentenoate

(2-tert-butoxy-2-oxoethyl)zinc(II) bromide
51656-70-3

(2-tert-butoxy-2-oxoethyl)zinc(II) bromide

A

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

B

di-tert-Butyl succinate
926-26-1

di-tert-Butyl succinate

C

(E)-4-Methyl-hex-2-enedioic acid 6-tert-butyl ester 1-methyl ester
92975-35-4

(E)-4-Methyl-hex-2-enedioic acid 6-tert-butyl ester 1-methyl ester

Conditions
ConditionsYield
In N,N,N,N,N,N-hexamethylphosphoric triamide at 25℃;A n/a
B n/a
C 20%
tert-butyl tetrahydropyranyl ether
1927-69-1

tert-butyl tetrahydropyranyl ether

acetyl chloride
75-36-5

acetyl chloride

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

Conditions
ConditionsYield
With montmorillonite K-10 In chloroform at 20℃; for 0.3h;10%
(4RS,5SR)-2,4-dimethyl-5-trimethylstannyl-2-hexanol
108964-71-2

(4RS,5SR)-2,4-dimethyl-5-trimethylstannyl-2-hexanol

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

Conditions
ConditionsYield
With borontrifluoride acetic acid In chloroform-d1 at -23℃; for 0.75h;9%
pyridine
110-86-1

pyridine

tetrachloromethane
56-23-5

tetrachloromethane

acetyl chloride
75-36-5

acetyl chloride

tert-butyl alcohol
75-65-0

tert-butyl alcohol

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

Conditions
ConditionsYield
at 65℃;
tetrachloromethane
56-23-5

tetrachloromethane

N-isobutyl-N-nitroso-acetamide
15289-94-8

N-isobutyl-N-nitroso-acetamide

A

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

B

sec-Butyl acetate
105-46-4

sec-Butyl acetate

C

2-methylpropyl acetate
110-19-0

2-methylpropyl acetate

Conditions
ConditionsYield
at 77℃;
Isobutyl iodide
513-38-2

Isobutyl iodide

A

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

B

tert-butyl alcohol
75-65-0

tert-butyl alcohol

Conditions
ConditionsYield
With acetic acid; silver(l) oxide
acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

1,2-bis(4-methoxyphenyl)butanone
4390-94-7

1,2-bis(4-methoxyphenyl)butanone

t-butyl 3-hydroxy-3,4-bis-(p-methoxyphenyl)-hexanoate
78765-20-5

t-butyl 3-hydroxy-3,4-bis-(p-methoxyphenyl)-hexanoate

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 2h;100%
acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

(S)-methyl 4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate
124655-05-6

(S)-methyl 4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate

(5S)-6-(tert-butyl-diphenylsilanyloxy)-5-hydroxy-3-oxohexanoic acid tert-butyl ester
124655-06-7

(5S)-6-(tert-butyl-diphenylsilanyloxy)-5-hydroxy-3-oxohexanoic acid tert-butyl ester

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at -70 - -15℃; for 1.75h;100%
Stage #1: acetic acid tert-butyl ester With n-butyllithium; diisopropylamine In tetrahydrofuran; hexanes at -40℃; for 0.5h; Claisen condensation; Inert atmosphere;
Stage #2: (S)-methyl 4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate In tetrahydrofuran; hexanes at -40 - 0℃; Inert atmosphere;
85%
acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

3-(Tetrahydro-pyran-2-yloxy)-8-{2-[2-(tetrahydro-pyran-2-yloxy)-heptyl]-[1,3]dithiolan-2-yl}-octanal
108400-92-6

3-(Tetrahydro-pyran-2-yloxy)-8-{2-[2-(tetrahydro-pyran-2-yloxy)-heptyl]-[1,3]dithiolan-2-yl}-octanal

t-butyl 3-hydroxy-5,13-di(tetrahydropyranyl)oxy-11-oxooctadecanoate-11-ethylenedithioketal
114903-16-1

t-butyl 3-hydroxy-5,13-di(tetrahydropyranyl)oxy-11-oxooctadecanoate-11-ethylenedithioketal

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 3h;100%
acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

(R,S)-4,5-diaminopentanoic acid dihydrochloride
89717-54-4

(R,S)-4,5-diaminopentanoic acid dihydrochloride

4,5-Diaminovaleric acid tert-butyl ester

4,5-Diaminovaleric acid tert-butyl ester

Conditions
ConditionsYield
With perchloric acid for 22h; Ambient temperature;100%
acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

9,17-di(tetrahydropyranyl)oxy-7,15-dioxodocosa-2,4-dienal-7,15-di(ethylenedithio)ketal

9,17-di(tetrahydropyranyl)oxy-7,15-dioxodocosa-2,4-dienal-7,15-di(ethylenedithio)ketal

t-butyl 3-hydroxy-11,19-di(tetrahydropyranyl)oxy-9,17-dioxotetracosa-4,6-doenoate-9,17-di(ethylenedithio)ketal

t-butyl 3-hydroxy-11,19-di(tetrahydropyranyl)oxy-9,17-dioxotetracosa-4,6-doenoate-9,17-di(ethylenedithio)ketal

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 2h;100%

540-88-5Relevant articles and documents

Esterification of tert-butanol and acetic acid by silicotungestic acid catalyst supported on bentonite

Jin, Jian-Zhong,Sun, Na-Bo

, p. 4441 - 4443 (2013)

A series of solid acid catalysts were synthesized by incipient wetness impregnation method by varying the wt % of silicotungstic acid on bentonite. Silicotungestic acid supported on bentonite was used to catalytic synthesis of tert-butyl acetate with acetic acid and tert-butyl alcohol. The main reaction parameters such as silicotungstic acid loading on bentonite, the amount of catalyst, molar ratio of reactants, reaction temperature and reaction time have been investigated. The optimum conditions were determined as follows: silicotungstic acid loading on bentonite 25 wt %, catalyst 0.7 g, mole ratio of tert-butanol to acetic acid 1:1.1, reaction temperature 110 °C and reaction time 2 h. The esterification yield of tert-butyl acetate was about 87.2 %. The catalyst could be used repeatedly for many times without distinct loss in activity.

Dehydrogenative ester synthesis from enol ethers and water with a ruthenium complex catalyzing two reactions in synergy

Ben-David, Yehoshoa,Diskin-Posner, Yael,Kar, Sayan,Luo, Jie,Milstein, David,Rauch, Michael

supporting information, p. 1481 - 1487 (2022/03/07)

We report the dehydrogenative synthesis of esters from enol ethers using water as the formal oxidant, catalyzed by a newly developed ruthenium acridine-based PNP(Ph)-type complex. Mechanistic experiments and density functional theory (DFT) studies suggest that an inner-sphere stepwise coupled reaction pathway is operational instead of a more intuitive outer-sphere tandem hydration-dehydrogenation pathway.

Green, efficient and economical coal fly ash based phosphomolybdic acid catalysts: preparation, characterization and application

Malpani, Sakshi Kabra,Goyal, Deepti,Katara, Stuti,Rani, Ashu

, p. 3017 - 3034 (2021/02/26)

Abstract: Cost-effective, efficient and green solid acid catalysts have been synthesized by incipient wetness impregnation of various weight fractions of phosphomolybdic acid (5, 10, 15 and 25 wt. %) on mechanically and thermally activated coal fly ash. N2 adsorption–desorption, XRD, FT-IR, SEM, SEM–EDX, TEM, TGA, UV–Vis DRS, solid state 31P MAS NMR were used for characterization of as synthesized catalysts. Catalytic active sites were developed on inert surface of coal fly ash by using various activation techniques whose performance was assessed over a series of acylation of various aliphatic alcohols. For rapid and higher catalytic activity, reactions were conducted in microwave heating mode. Impregnation of phosphomolybdic acid generates Lewis acidic sites on coal fly ash surface as inferred by pyridine adsorbed FT-IR studies which were then utilized in acylation reactions. Various reaction parameters like weight fraction of catalysts, molar ratio of reactants, time, temperature, etc. were optimized for attaining highest conversion %. The catalyst with 15 wt. % of phosphomolybdic acid was found to be more efficient and could be recycled up to five reaction cycles with analogous conversion %. Negligible leaching of catalyst was confirmed by hot filtration test. This work suggests an alternative approach for valorisation of industrial solid waste, coal fly ash in development of innovative, economical solid catalysts. Graphic abstract: [Figure not available: see fulltext.].

Genome mining reveals new bacterial type I Baeyer-Villiger monooxygenases with (bio)synthetic potential

Bianchi, Dario A.,Carabajal, María Ayelén,Ceccoli, Romina D.,Rial, Daniela V.

, (2020/03/19)

Baeyer-Villiger monooxygenases (BVMOs) are oxidorreductases that catalyze the oxidation of ketones in a very selective manner. By genome mining we detected seven putative type I BVMOs in Bradyrhizobium diazoefficiens USDA 110. As we established the phylogenetic relationships among them and with other type I BVMOs, we found out that they belong to different clades of the phylogenetic tree. Thus, we decided to clone and heterologously express five of them. Three of them, each one from a divergent phylogenetic group, were obtained as soluble proteins, allowing us to proceed with their biocatalytic assessment and enzymatic characterization. As to substrate scope and selectivity, we observed a complementary behavior among the three BVMOs. BVMO2 was the more versatile biocatalyst in whole-cell systems while BVMO4 and BVMO5 showed a narrow substrate profile with preference for linear ketones and particular regioselectivity for (±)-cis-bicyclo[3.2.0]hept-2-en-6-one.

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