Product Name

  • Name

    Methyl o-toluate

  • EINECS 201-932-2
  • CAS No. 89-71-4
  • Article Data173
  • CAS DataBase
  • Density 1.045 g/cm3
  • Solubility Not miscible or difficult to mix in water.
  • Melting Point -50ºC
  • Formula C9H10O2
  • Boiling Point 215 °C at 760 mmHg
  • Molecular Weight 150.177
  • Flash Point 82.2 °C
  • Transport Information
  • Appearance clear colorless liquid
  • Safety 37/39-26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 89-71-4 (Methyl o-toluate)
  • Hazard Symbols IrritantXi
  • Synonyms o-Toluicacid, methyl ester (6CI,7CI,8CI);2-Methylbenzoic acid methyl ester;2-Toluicacid methyl ester;Methyl 2-methylbenzoate;Methyl 2-toluate;Methylo-methylbenzoate;Methyl orthotoluate;NSC 9402;
  • PSA 26.30000
  • LogP 1.78160

Synthetic route

methanol
67-56-1

methanol

2-methyl-benzyl alcohol
89-95-2

2-methyl-benzyl alcohol

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: methanol With sodium tetrachloroaurate(III) dihyrate; potassium carbonate at 20℃; for 0.0166667h; Green chemistry;
Stage #2: 2-methyl-benzyl alcohol at 20℃; for 0.0333333h; Green chemistry;
Stage #3: With oxygen at 80℃; under 760.051 Torr; Autoclave; Green chemistry;		94%
With Au#Co; oxygen; potassium carbonate at 80℃; under 750.075 Torr; for 7h; Autoclave;94%
With potassium carbonate at 80℃; under 750.075 Torr; for 6h;91.7%
ortho-methylbenzoic acid
118-90-1

ortho-methylbenzoic acid

methanol
67-56-1

methanol

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid for 41h; Heating;93%
With sulfuric acid for 4h; Heating;90%
With beef pancreas lipase at 20℃; for 5h;86%
ortho-methylbenzoic acid
118-90-1

ortho-methylbenzoic acid

methyl iodide
74-88-4

methyl iodide

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With sodium hydrogencarbonate In N-methyl-acetamide90.6%
With potassium carbonate In acetone; acetonitrile at 20 - 50℃; for 2h; Inert atmosphere;
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 10h; Inert atmosphere; Sealed tube;
In acetonitrile for 8h; Inert atmosphere; Alkaline conditions;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

5,5-dimethyl-2-(o-tolyl)-1,3,2-dioxaborinane
91994-11-5

5,5-dimethyl-2-(o-tolyl)-1,3,2-dioxaborinane

methyl iodide
74-88-4

methyl iodide

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: di-tert-butyl dicarbonate; 5,5-dimethyl-2-(o-tolyl)-1,3,2-dioxaborinane With 4,4'-dimethyl-2,2'-bipyridines; lithium methanolate; copper(l) chloride In N,N-dimethyl acetamide at 30℃; for 6h; Inert atmosphere; Schlenk technique;
Stage #2: methyl iodide In N,N-dimethyl acetamide at 30℃; for 2h; Schlenk technique;		85%
...Expand
methanol
67-56-1

methanol

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With triethylamine; Azobenzene In tetrahydrofuran at 20℃; for 24h;97%
With urea hydrogen peroxide adduct; p-toluenesulfonyl chloride at 60℃; for 8h;88%
With dihydrogen peroxide; bromine In dichloromethane; water for 4h; Reflux;87%
methanol
67-56-1

methanol

2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

B

N,N,2-trimethylbenzamide
6639-19-6

N,N,2-trimethylbenzamide

Conditions
ConditionsYield
Stage #1: 2-methylphenyl bromide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78 - 20℃; for 2h;
Stage #3: methanol Further stages;		A 78%
B 7%
...Expand
methanol
67-56-1

methanol

ortho-toluoyl chloride
933-88-0

ortho-toluoyl chloride

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With triethylamine at 20℃; for 0.5h;
With triethylamine In dichloromethane at 0℃;
at 0 - 5℃;
With triethylamine In dichloromethane at 0℃; Inert atmosphere;1.42 g
2-Methylacetophenone
577-16-2, 122382-54-1

2-Methylacetophenone

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With oxygen; 1-(n-butyl)-3-methylimidazolium triflate at 20℃; for 0.333333h; Baeyer-Villiger Ketone Oxidation; Electrochemical reaction; Green chemistry;94%
carbon monoxide
201230-82-2

carbon monoxide

2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

A

ortho-methylbenzoic acid
118-90-1

ortho-methylbenzoic acid

B

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With methanol; tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 18h; Irradiation;A 9.5%
B 53%
...Expand
ortho-methylbenzoic acid
118-90-1

ortho-methylbenzoic acid

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: oxalyl chloride / CH2Cl2; dimethylformamide / 2 h / Heating
2.1: pyridine / CH2Cl2 / 20 h
3.1: Na2HPO4 / acetonitrile / 20 °C
3.2: 94 percent / aq. NaHCO3 / 18 h
View Scheme
Multi-step reaction with 3 steps
1.1: oxalyl chloride / CH2Cl2; dimethylformamide / 2 h / Heating
2.1: pyridine / CH2Cl2 / 20 h
3.1: Na2HPO4 / acetonitrile / 20 °C
3.2: 87 percent / aq. NaHCO3 / 18 h
View Scheme
With sulfuric acid In methanol; water
ortho-methylbenzoic acid
118-90-1

ortho-methylbenzoic acid

methoxybenzene
100-66-3

methoxybenzene

A

4-Methylanisole
104-93-8

4-Methylanisole

B

2-methylmethoxybenzene
578-58-5

2-methylmethoxybenzene

C

phenyl 2-methylbenzoate
15813-38-4

phenyl 2-methylbenzoate

D

(4-methoxyphenyl)(2-methylphenyl)methanone
41204-59-5

(4-methoxyphenyl)(2-methylphenyl)methanone

E

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With erbium(III) triflate In neat (no solvent) at 220℃; for 0.5h; Friedel-Crafts Acylation; Microwave irradiation;A n/a
B n/a
C n/a
D 72%
E n/a
...Expand
methanol
67-56-1

methanol

o-xylene
95-47-6

o-xylene

A

ortho-methylbenzoic acid
118-90-1

ortho-methylbenzoic acid

B

phthalic acid dimethyl ester
131-11-3

phthalic acid dimethyl ester

C

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: o-xylene With ruthenium(II) chloride; [C20H8N4(C6H4Cl)4Fe]2O; N-hydroxy-3-pyridylmethyl phthalimide; oxygen at 185℃; under 10501.1 Torr;
Stage #2: methanol Reagent/catalyst; Pressure; Temperature;		A 31.2%
B 33.1%
C 28.4%
...Expand
methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

A

ortho-methylbenzoic acid
118-90-1

ortho-methylbenzoic acid

B

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 18h; Irradiation;A 9.5%
B 53%
...Expand
methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With benzophenone; sodium methylate; cobalt(II) acetate at 40℃; under 750.075 Torr; for 15h; Irradiation;70%
Stage #1: methanol; carbon monoxide; 2-methylphenyl bromide With potassium carbonate at 20℃; for 0.25h;
Stage #2: With dicobalt octacarbonyl; methyloxirane at 63℃;
With bis(diphenylphosphino)propanepalladium(II) dichloride; potassium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; under 3750.38 Torr; for 24h; Reagent/catalyst; Inert atmosphere; Autoclave; chemoselective reaction;100 %Chromat.
...Expand
N,N,2-trimethylbenzamide
6639-19-6

N,N,2-trimethylbenzamide

trimethoxonium tetrafluoroborate
420-37-1

trimethoxonium tetrafluoroborate

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: N,N,2-trimethylbenzamide; trimethoxonium tetrafluoroborate With disodium hydrogenphosphate In acetonitrile at 20℃; Methylation;
Stage #2: With sodium hydrogencarbonate for 18h; Hydrolysis;		94%
N,N-diethyl-ortho-toluamide
2728-04-3

N,N-diethyl-ortho-toluamide

trimethoxonium tetrafluoroborate
420-37-1

trimethoxonium tetrafluoroborate

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: N,N-diethyl-ortho-toluamide; trimethoxonium tetrafluoroborate With disodium hydrogenphosphate In acetonitrile at 20℃; Methylation;
Stage #2: With sodium hydrogencarbonate for 18h; Hydrolysis;		87%
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

methyl trifluoromethanesulfonate
333-27-7

methyl trifluoromethanesulfonate

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: 2-bromobenzoic acid methyl ester With sec.-butyllithium In tetrahydrofuran; hexane; cyclohexane at -48℃;
Stage #2: methyl trifluoromethanesulfonate In tetrahydrofuran; hexane; cyclohexane at -48℃;		65 %Chromat.
Stage #1: 2-bromobenzoic acid methyl ester With sec.-butyllithium In tetrahydrofuran; hexane; cyclohexane at -48℃; for 5.55556E-06h;
Stage #2: methyl trifluoromethanesulfonate In tetrahydrofuran; hexane; cyclohexane at -48℃; for 0.000638889h;		65 %Chromat.
methanol
67-56-1

methanol

o-xylene
95-47-6

o-xylene

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With hydrogenchloride; oxygen; 9-(2-mesityl)-10-methylacridinium perchlorate at 20℃; under 760.051 Torr; for 30h; Schlenk technique; Irradiation; Green chemistry;87%
With oxygen at 120℃; under 7500.75 Torr; for 72h;66%
methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

o-toluidine
95-53-4

o-toluidine

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: o-toluidine With tetrafluoroboric acid; acetic acid; isopentyl nitrite In water at 20℃; for 0.0833333h;
Stage #2: methanol; carbon monoxide With Eosin Y at 18℃; under 37503.8 Torr; for 4h; Inert atmosphere; Darkness; Irradiation;		73%
...Expand
methanol
67-56-1

methanol

ortho-methylphenyl iodide
615-37-2

ortho-methylphenyl iodide

carbon monoxide
201230-82-2

carbon monoxide

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With triethylamine at 100℃; under 3750.38 Torr; for 1.5h; Inert atmosphere;98%
With triethylamine; palladium on activated charcoal at 130℃; under 3750.38 Torr; for 2h; Sonogashira coupling;69%
With dichloro bis(acetonitrile) palladium(II); potassium carbonate; triphenylphosphine at 63℃;
With palladium diacetate; potassium carbonate at 100℃; under 5250.53 Torr; for 3h; Catalytic behavior;83 %Chromat.
...Expand
ortho-methylbenzoic acid
118-90-1

ortho-methylbenzoic acid

methyl 1-imidazolecarboxylate
61985-23-7

methyl 1-imidazolecarboxylate

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere;90%
2-methylphenylzinc chloride
84109-17-1

2-methylphenylzinc chloride

methyl chloroformate
79-22-1

methyl chloroformate

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; benzene at 25℃;73%
methanol
67-56-1

methanol

N,2-dimethyl-N-phenylbenzamide
22978-37-6

N,2-dimethyl-N-phenylbenzamide

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); 1,3-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene In toluene at 80℃; for 12h;89%
2-methylbenzoyl fluoride
364-20-5

2-methylbenzoyl fluoride

tris(2,4,6-trimethoxyphenyl)phosphine
91608-15-0

tris(2,4,6-trimethoxyphenyl)phosphine

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
In toluene at 130℃; for 24h; Schlenk technique; Inert atmosphere;90%
methyl 2-{[(4-methylphenyl)sulfonyl]oxy}benzoate
51207-44-4

methyl 2-{[(4-methylphenyl)sulfonyl]oxy}benzoate

methyl p-toluene sulfonate
80-48-8

methyl p-toluene sulfonate

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With (1,2-dimethoxyethane)dichloronickel(II); tetra-(n-butyl)ammonium iodide; triphenylphosphine; magnesium chloride; zinc In N,N-dimethyl acetamide at 25℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube;68%
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

methyl p-toluene sulfonate
80-48-8

methyl p-toluene sulfonate

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With nickel(II) iodide; 4,4'-dimethyl-2,2'-bipyridines; tetra-(n-butyl)ammonium iodide; magnesium chloride; zinc In N,N-dimethyl acetamide at 20℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube;72%
O-methyl S-p-methylphenyl thiocarbonate
3186-53-6

O-methyl S-p-methylphenyl thiocarbonate

2-Methylphenylboronic acid
16419-60-6

2-Methylphenylboronic acid

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); copper(I) thiophene-2-carboxylate; trifuran-2-yl-phosphane In 1,4-dioxane at 60℃; for 16h; Sealed tube; Inert atmosphere;65%
methanol
67-56-1

methanol

2-methylbenzoyl cyanide
5955-73-7

2-methylbenzoyl cyanide

A

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

B

methyl 2-oxo-2-(o-tolyl)acetate
34966-54-6

methyl 2-oxo-2-(o-tolyl)acetate

Conditions
ConditionsYield
With sulfuric acid; sodium bromide Mechanism; Product distribution; other sodium halides;
With sulfuric acid; sodium bromide 1.) 70 deg C; 2.) reflux; Yield given. Multistep reaction. Yields of byproduct given;
Stage #1: 2-methylbenzoyl cyanide With hydrogenchloride In 5,5-dimethyl-1,3-cyclohexadiene at -5 - 0℃; for 1h;
Stage #2: methanol With sulfuric acid In 5,5-dimethyl-1,3-cyclohexadiene at 15 - 65℃; for 14h;
...Expand
N-methoxy-2-methylbenzamide
57139-25-0

N-methoxy-2-methylbenzamide

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 85℃; for 1.91667h; Electrolysis;52%
2,5-dihydrotoluene
4313-57-9

2,5-dihydrotoluene

propynoic acid methyl ester
922-67-8

propynoic acid methyl ester

A

2-Methyl-benzoic acid methyl ester
89-71-4

2-Methyl-benzoic acid methyl ester

B

(E)-3-(6-Methylene-cyclohex-3-enyl)-acrylic acid methyl ester
73588-12-2

(E)-3-(6-Methylene-cyclohex-3-enyl)-acrylic acid methyl ester

Conditions
ConditionsYield
ethylaluminum dichloride In dichloromethane for 96h;A 13%
B 66%
...Expand

Methyl o-toluate Specification

The Benzoic acid,2-methyl-, methyl ester is an organic compound with the formula C9H10O2. The IUPAC name of this chemical is methyl 2-methylbenzoate. With the CAS registry number 89-71-4, it is also named as o-Toluic acid, methyl ester. The product's categories are Carboxylicester; Aromatic Esters. Besides, it is a clear colorless liquid, which should be stored in a closed cool and dry place. It is used for organic synthesis.

Physical properties about Benzoic acid,2-methyl-, methyl ester are: (1)ACD/LogP: 2.66; (2)ACD/LogD (pH 5.5): 2.66; (3)ACD/LogD (pH 7.4): 2.66; (4)ACD/BCF (pH 5.5): 61.46; (5)ACD/BCF (pH 7.4): 61.46; (6)ACD/KOC (pH 5.5): 663.56; (7)ACD/KOC (pH 7.4): 663.56; (8)#H bond acceptors: 2 ; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 26.3 Å2; (11)Index of Refraction: 1.508; (12)Molar Refractivity: 42.85 cm3; (13)Molar Volume: 143.6 cm3; (14)Polarizability: 16.98×10-24cm3; (15)Surface Tension: 35.1 dyne/cm; (16)Density: 1.045 g/cm3; (17)Flash Point: 82.2 °C; (18)Enthalpy of Vaporization: 45.13 kJ/mol; (19)Boiling Point: 215 °C at 760 mmHg; (20)Vapour Pressure: 0.151 mmHg at 25°C.

Preparation: this chemical can be prepared by 2-methyl-benzoic acid and methanol. This reaction will need reagent H2SO4.



Uses of Benzoic acid,2-methyl-, methyl ester: it can be used to produce 2-bromomethyl-benzoic acid methyl ester. It will need reagent NBS and solvent CCl4.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC)c1ccccc1C
(2)InChI: InChI=1/C9H10O2/c1-7-5-3-4-6-8(7)9(10)11-2/h3-6H,1-2H3
(3)InChIKey: WVWZECQNFWFVFW-UHFFFAOYAO
(4)Std. InChI: InChI=1S/C9H10O2/c1-7-5-3-4-6-8(7)9(10)11-2/h3-6H,1-2H3
(5)Std. InChIKey: WVWZECQNFWFVFW-UHFFFAOYSA-N

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