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2-Methyl-3-biphenylmethanol
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Name

2-Methyl-3-biphenylmethanol

 EINECS 1312995-182-4
CAS No. 76350-90-8 Density 1.073 g/cm3
PSA 20.23000 LogP 3.15430
Solubility Insoluble in water, soluble in ethanol, benzene and toluene Melting Point 73-76 °C(lit.)
Formula C14H14O Boiling Point 330.922 °C at 760 mmHg
Molecular Weight 198.265 Flash Point 143.013 °C
Transport Information N/A Appearance white to light yellow crystal powder
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 76350-90-8 (2-Methyl-3-biphenylmethanol) Hazard Symbols N/A
Synonyms

2-Methyl-3-phenylbenzylalcohol;2-Methylbiphenyl-3-ylmethanol;3-Hydroxymethyl-2-methylbiphenyl;2-Methyl-3-biphenylmethanol;

Article Data 25

2-Methyl-3-biphenylmethanol Synthetic route

83647-43-2

3-bromo-2-methylbenzyl alcohol

98-80-6

phenylboronic acid

76350-90-8

(2-methyl-[1,1'-biphenyl]-3-yl)methanol

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydrogencarbonate In ethanol; toluene at 80℃; for 0.5h; Suzuki-Miyaura Coupling; Inert atmosphere;98%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium acetate In tetrahydrofuran Suzuki-Miyaura Coupling; Reflux;98%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydrogencarbonate In ethanol; toluene at 80℃; for 3h; Inert atmosphere;98%
502483-86-5

1,3-dihydro-4-phenylisobenzofuran

76350-90-8

(2-methyl-[1,1'-biphenyl]-3-yl)methanol

Conditions
ConditionsYield
Stage #1: 1,3-dihydro-4-phenylisobenzofuran With lithium; 4,4'-di-tert-butylbiphenyl In tetrahydrofuran at -78℃; for 3h;
Stage #2: With water In tetrahydrofuran at -78℃; for 0.333333h;
Stage #3: With water In tetrahydrofuran at -78 - 20℃; Further stages.;		95%
Multi-step reaction with 2 steps
1.1: Li; DTBB / tetrahydrofuran / 3 h / -78 °C
2.1: H2O / 0.5 h / -78 °C
2.2: H2O / -78 - 20 °C
View Scheme
84541-46-8

3-chloromethyl-2-methyl-[1,1'-biphenyl]

76350-90-8

(2-methyl-[1,1'-biphenyl]-3-yl)methanol

Conditions
ConditionsYield
With tetrabutylammomium bromide; water; sodium acetate at 100℃; for 15h; Reagent/catalyst;91%

Bifenthrin

A

76350-90-8

(2-methyl-[1,1'-biphenyl]-3-yl)methanol

B

76023-99-9

(1R,3R)-3-((Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2,-dimethylcyclopropane-1-carboxylic acid

Conditions
ConditionsYield
With potassium hydroxide In methanol for 2h; Hydrolysis; Heating;

C14H12OLi(1-)*Li(1+)

76350-90-8

(2-methyl-[1,1'-biphenyl]-3-yl)methanol

Conditions
ConditionsYield
Stage #1: C14H12OLi(1-)*Li(1+) With water at -78℃; for 0.5h;
Stage #2: With water at -78 - 20℃; Further stages.;

4-bromo-1,3-dihydro-2-benzofuran

76350-90-8

(2-methyl-[1,1'-biphenyl]-3-yl)methanol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: palladium
2.1: Li; DTBB / tetrahydrofuran / 3 h / -78 °C
3.1: H2O / 0.5 h / -78 °C
3.2: H2O / -78 - 20 °C
View Scheme
576-23-8

2,3-dimethylbromobenzene

76350-90-8

(2-methyl-[1,1'-biphenyl]-3-yl)methanol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: N-bromosuccinimide; AIBN
2.1: tetrabutylammonium hydroxide / dioxane
3.1: palladium
4.1: Li; DTBB / tetrahydrofuran / 3 h / -78 °C
5.1: H2O / 0.5 h / -78 °C
5.2: H2O / -78 - 20 °C
View Scheme
127168-82-5

1-bromo-2,3-bis(bromomethyl)benzene

76350-90-8

(2-methyl-[1,1'-biphenyl]-3-yl)methanol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: tetrabutylammonium hydroxide / dioxane
2.1: palladium
3.1: Li; DTBB / tetrahydrofuran / 3 h / -78 °C
4.1: H2O / 0.5 h / -78 °C
4.2: H2O / -78 - 20 °C
View Scheme

bifenthrin

A

74609-46-4

3-(2-chloro-3,3,3-trifluoroprop-1-en-yl)-2,2-dimethylcyclopropanecarboxylic acid

B

76350-90-8

(2-methyl-[1,1'-biphenyl]-3-yl)methanol

Conditions
ConditionsYield
With carboxylesterase EstSt7 from Sulfolobus tokodaii strain 7; water In ethanol at 80℃; pH=9; Kinetics; Enzymatic reaction;
76006-33-2

3-bromo-2-methylbenzoic acid

76350-90-8

(2-methyl-[1,1'-biphenyl]-3-yl)methanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: borane-THF / tetrahydrofuran / 20 °C / Cooling with ice
2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydrogencarbonate / toluene; ethanol / 0.5 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: borane-THF / tetrahydrofuran / 15 h / 0 - 20 °C / Inert atmosphere
2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydrogencarbonate / ethanol; toluene / 0.5 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: borane-THF / tetrahydrofuran / 15 h / 0 - 20 °C / Inert atmosphere
2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydrogencarbonate / toluene; ethanol / 0.5 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: sulfuric acid / 60 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C
2.2: 1 h / 0 °C
3.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 3 h / 100 °C / Inert atmosphere
View Scheme

2-Methyl-3-biphenylmethanol Specification

The 2-Methyl-3-biphenylmethanol, with the CAS registry number 76350-90-8, is also known as 3-Hydroxymethyl-2-methylbiphenyl. It belongs to the product categories of Aromatic alcohols and diols; Alkohols; Pesticide; C9 to C30; Oxygen Compounds; Aromatics; Intermediates & Fine Chemicals; Pharmaceuticals. This chemical's molecular formula is C14H14O and molecular weight is 198.26. What's more, its systematic name is (2-Methyl-3-biphenylyl)methanol. This chemical should be sealed and stored in a cool and dry place. Moreover, it should be protected from oxides. It is used as as Bifenthrin intermediate.

Physical properties of 2-Methyl-3-biphenylmethanol are: (1)ACD/LogP: 3.252; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.25; (4)ACD/LogD (pH 7.4): 3.25; (5)ACD/BCF (pH 5.5): 174.41; (6)ACD/BCF (pH 7.4): 174.41; (7)ACD/KOC (pH 5.5): 1399.98; (8)ACD/KOC (pH 7.4): 1399.98; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 20.23 Å2; (13)Index of Refraction: 1.587; (14)Molar Refractivity: 62.121 cm3; (15)Molar Volume: 184.81 cm3; (16)Polarizability: 24.627×10-24cm3; (17)Surface Tension: 42.5 dyne/cm; (18)Density: 1.073 g/cm3; (19)Flash Point: 143.013 °C; (20)Enthalpy of Vaporization: 60.541 kJ/mol; (21)Boiling Point: 330.922 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Uses of 2-Methyl-3-biphenylmethanol: it can be used to produce 2,2-dimethyl-3-(2-methyl-propenyl)-cyclopropanecarboxylic acid 2-methyl-biphenyl-3-ylmethyl ester at the ambient temperature. It will need solvents diethyl ether, pyridine with the reaction time of 3 hours. The yield is about 85%.

2-Methyl-3-biphenylmethanol can be used to produce 2,2-dimethyl-3-(2-methyl-propenyl)-cyclopropanecarboxylic acid 2-methyl-biphenyl-3-ylmethyl ester at the ambient temperature

You can still convert the following datas into molecular structure:
(1)SMILES: OCc2cccc(c1ccccc1)c2C
(2)Std. InChI: InChI=1S/C14H14O/c1-11-13(10-15)8-5-9-14(11)12-6-3-2-4-7-12/h2-9,15H,10H2,1H3
(3)Std. InChIKey: BGTLHJPGBIVQLJ-UHFFFAOYSA-N

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