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118-90-1

Basic Information
CAS No.: 118-90-1
Name: o-Toluic acid
Molecular Structure:
Molecular Structure of 118-90-1 (o-Toluic acid)
Formula: C8H8O2
Molecular Weight: 136.16
Synonyms: o-Toluate;2-Methylbenzoic acid;o-Methylbenzoic acid;o-Methylbenzoate;2-methylbenzoate;Orthotoluic acid;Benzoic acid, 2-methyl-;Toluic acid;2-Methylbenzoic acid;o-Toluic acid;
EINECS: 204-284-9
Density: 1.151 g/cm3
Melting Point: 103-105 ºC
Boiling Point: 260.9 ºC at 760 mmHg
Flash Point: 118.8 ºC
Solubility: <0.1 g/100 mL at 19 ºC in water
Appearance: Pale yellow crystals or off-white flaky solid.
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 22-36/37/38
Safety: 26-36-22
Transport Information:
PSA: 37.30000
LogP: 1.69320
Synthetic route
174473-23-5

2-methylbenzyltri-n-butylstannane

118-90-1

ortho-methylbenzoic acid

Conditions
ConditionsYield
With C2H2Cl2F3O2V; oxygen In tert-butyl alcohol at 50℃; for 72h;100%
With VO(CH2CF3)Cl2; oxygen In tert-butyl alcohol at 50℃; for 72h;100%
529-19-1

2-Methylbenzonitrile

118-90-1

ortho-methylbenzoic acid

Conditions
ConditionsYield
With phosphate buffer at 30℃; for 120h; rhodococcus rhodocrous AJ270, pH 7.0;99%
With potassium phosphate buffer at 30℃; for 120h; Rhodococcus sp. AJ270 cells;98.9%
With benzene-1,2-dicarboxylic acid for 0.833333h; microwave-irradiation;91%
529-20-4

2-methylphenyl aldehyde

118-90-1

ortho-methylbenzoic acid

Conditions
ConditionsYield
With 2-mesityl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In acetonitrile at 20℃;99%
With sodium chlorite; dimethyl sulfoxide In water; acetonitrile at 10℃; for 1.2h;98.6%
With oxygen; copper(II) acetate monohydrate; cobalt(II) diacetate tetrahydrate In water at 70℃; under 760.051 Torr; for 12h;96%
89-71-4

2-Methyl-benzoic acid methyl ester

118-90-1

ortho-methylbenzoic acid

Conditions
ConditionsYield
With iodine; aluminium In acetonitrile at 80℃; for 18h;99%
With methanesulfonic acid; 1-methylimidazolium hydrobromide at 120℃; for 2h;92%
With AlBrCl3(1-)*C5H5N*H(1+) at 140℃; for 3h;91%
89-95-2

2-methyl-benzyl alcohol

118-90-1

ortho-methylbenzoic acid

Conditions
ConditionsYield
With oxygen; sodium carbonate In water at 100℃; under 52505.3 Torr; for 0.533333h; Flow reactor; Green chemistry;98%
With picoline; tert.-butylhydroperoxide; chlorophyllin coppered trisodium salt In water at 80℃; for 15h; chemoselective reaction;97%
With dichloro(1,5-cyclooctadiene)ruthenium(II); C30H30N3P2(1+)*Cl(1-); potassium hydroxide In toluene at 120℃; for 24h; Inert atmosphere; Schlenk technique;96%
95-47-6

o-xylene

118-90-1

ortho-methylbenzoic acid

Conditions
ConditionsYield
With oxygen; tetra-N-butylammonium tribromide In ethyl acetate at 20℃; for 48h; Catalytic behavior; Irradiation;97%
With tert.-butylhydroperoxide; water at 20℃; for 12h; Inert atmosphere;90%
With tert.-butylhydroperoxide; chromium-pillared montmorillonite In 2,2,4-trimethylpentane; dichloromethane for 48h; Ambient temperature;87%
16537-18-1

o-toluic acid t-butyl ester

118-90-1

ortho-methylbenzoic acid

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran at 20℃; for 30h;97%
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6h;74%
67157-60-2

2-methyl-benzoic acid benzyl ester

108-88-3

toluene

A

118-90-1

ortho-methylbenzoic acid

B

620-83-7

1-methyl-4-(phenylmethyl)benzene

C

713-36-0

2-benzyltoluene

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; water at 80℃; for 2h; regioselective reaction;A 97%
B n/a
C n/a
201230-82-2

carbon monoxide

95-46-5

2-methylphenyl bromide

118-90-1

ortho-methylbenzoic acid

Conditions
ConditionsYield
With tetrabutylammomium bromide; dicobalt octacarbonyl In sodium hydroxide; benzene at 65℃; for 1.5h; Irradiation;96%
With sodium hydroxide; tetrabutylammomium bromide; dicobalt octacarbonyl In water; benzene at 65℃; under 760 Torr; for 2.25h; Irradiation;96%
With sodium hydroxide; tetra-(n-butyl)ammonium iodide; bis(benzonitrile)palladium(II) dichloride; triphenylphosphine In xylene at 90℃; for 4h; Carbonylation;18%
615-37-2

ortho-methylphenyl iodide

201230-82-2

carbon monoxide

118-90-1

ortho-methylbenzoic acid

Conditions
ConditionsYield
With potassium hydroxide; amphiphilic resin-supported phosphine-palladium; water at 25℃; under 760 Torr; for 12h; Product distribution; Further Variations:; Reagents; hydroxycarbonylation;96%
With water; palladium diacetate; potassium carbonate at 20℃; under 760.051 Torr; for 12h;89%
With water; potassium carbonate In acetonitrile at 100℃; under 3750.38 Torr; for 0.0161111h;86%
64-18-6

formic acid

615-37-2

ortho-methylphenyl iodide

118-90-1

ortho-methylbenzoic acid

Conditions
ConditionsYield
With palladium diacetate; triethylamine; dicyclohexyl-carbodiimide; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere; Sealed tube;95%
With palladium diacetate; triethylamine; dicyclohexyl-carbodiimide; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 100℃; for 20h; Inert atmosphere; Sealed tube;83%
3609-56-1

allyl 2-methylbenzoate

118-90-1

ortho-methylbenzoic acid

Conditions
ConditionsYield
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 25℃; for 3.5h; Inert atmosphere;95%
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide; mineral oil at 25℃; for 4h; Inert atmosphere;95%

methyl 3-oxo-3-(o-tolyl)propanedithioate

118-90-1

ortho-methylbenzoic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 100℃; for 9.5h; Reflux; chemoselective reaction;94%
57139-25-0

N-methoxy-2-methylbenzamide

118-90-1

ortho-methylbenzoic acid

Conditions
ConditionsYield
With tert.-butylnitrite; water at 29℃; for 0.583333h;94%
577-16-2, 122382-54-1

2-Methylacetophenone

118-90-1

ortho-methylbenzoic acid

Conditions
ConditionsYield
With 1,10-Phenanthroline; oxygen; copper diacetate; potassium hydroxide In dimethyl sulfoxide at 130℃; under 3000.3 Torr; for 12h; Autoclave;93%
With sodium hypochlorite; lithium hypochlorite In ethanol at 77℃; for 2h;89%
With copper(l) iodide; hydroxylamine hydrochloride; oxygen In dimethyl sulfoxide at 100℃; for 8h;87%
64158-25-4

2,2'-dimethylhydrobenzoin

118-90-1

ortho-methylbenzoic acid

Conditions
ConditionsYield
With sodium hypochlorite In acetonitrile at 20℃; for 3h;93%
529-19-1

2-Methylbenzonitrile

A

118-90-1

ortho-methylbenzoic acid

B

527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With phosphate buffer at 30℃; for 5.5h; rhodococcus rhodocrous AJ270, pH 7.0;A 7%
B 92%
With potassium phosphate buffer at 30℃; for 5.5h; Rhodococcus sp. AJ270 cells;A 6.6%
B 92.4%
124-38-9

carbon dioxide

366-39-2

2-methylphenyl sulfurofluoridate

118-90-1

ortho-methylbenzoic acid

Conditions
ConditionsYield
With manganese; bis(triphenylphosphine)nickel(II) chloride; 2.9-dimethyl-1,10-phenanthroline In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; for 20h; Schlenk technique; Inert atmosphere; Glovebox;92%
95-52-3

2-Fluorotoluene

124-38-9

carbon dioxide

118-90-1

ortho-methylbenzoic acid

Conditions
ConditionsYield
Stage #1: 2-Fluorotoluene With C78H70Al2Cl4N6P4Rh2; magnesium; ethylene dibromide In tetrahydrofuran at 20℃; for 22h; Inert atmosphere; Glovebox;
Stage #2: carbon dioxide In tetrahydrofuran at 20℃; under 760.051 Torr; for 0.5h;
92%
124-38-9

carbon dioxide

2093-46-1

2-methylphenyl diazonium tetrafluoroborate

118-90-1

ortho-methylbenzoic acid

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate In N,N-dimethyl-formamide for 2h; Electrochemical reaction;91%
55886-48-1

2-methylcyclohexa-2,5-diene-1-carboxylic acid

118-90-1

ortho-methylbenzoic acid

Conditions
ConditionsYield
In acetone at 0℃; for 2h;90%
1130-97-8

2-methylbenzoic acid, 2,2-dimethylhydrazide

118-90-1

ortho-methylbenzoic acid

Conditions
ConditionsYield
With manganese(IV) oxide; acetic acid In water at 25℃; Oxidation;90%
With copper dichloride In 1,4-dioxane; water Oxidation;83%
611-15-4

1-methyl-2-vinyl-benzene

118-90-1

ortho-methylbenzoic acid

Conditions
ConditionsYield
Stage #1: 1-methyl-2-vinyl-benzene With tert.-butylhydroperoxide; iron(III) chloride hexahydrate; sodium hydroxide In water at 80℃; for 10h;
Stage #2: With hydrogenchloride In water at 20℃;
90%
With methyl 3,5-bis((1H-1,2,4-triazol-1-yl)methyl)benzoate; oxygen; sodium acetate; nickel dibromide at 120℃; under 760.051 - 912.061 Torr; for 48h; chemoselective reaction;72%
Stage #1: 1-methyl-2-vinyl-benzene With tert.-butylhydroperoxide; iodine; sodium hydroxide In water at 105℃; for 16h; Sealed tube;
Stage #2: With hydrogenchloride In water
51%
With Oxone In water; acetonitrile for 24h; Reflux;8%
16419-60-6

2-Methylphenylboronic acid

141-97-9

ethyl acetoacetate

118-90-1

ortho-methylbenzoic acid

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate In dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere;90%
38362-89-9

1-methyl-2-(2-nitroethyl)benzene

118-90-1

ortho-methylbenzoic acid

Conditions
ConditionsYield
With zinc diacetate; water; tetra-(n-butyl)ammonium iodide at 80℃; for 24h;90%
With water; tetra-(n-butyl)ammonium iodide at 80℃; for 15h; Reagent/catalyst;90%
With tetra-(n-butyl)ammonium iodide; acetic acid In water at 80℃; for 15h; Reagent/catalyst;89%
95-47-6

o-xylene

A

118-90-1

ortho-methylbenzoic acid

B

88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
Stage #1: o-xylene With manganese(IV) oxide; C32H16N8O4Ru; C46H39CrN12O2; oxygen at 195℃; under 14251.4 Torr; for 0.2h;
Stage #2: With manganese(IV) oxide; C32H16N8O4Ru; C46H39CrN12O2; oxygen; acetic acid at 150℃; under 4500.45 Torr; for 4h; Temperature; Pressure; Reagent/catalyst;
A 89.3%
B 10.6%
Stage #1: o-xylene With N-acetylphthalimide; Cr(4+)*4NO3(1-); C36H24N8NiO4; C52H44FeN4O8; oxygen at 120℃; under 2250.23 Torr; for 1.5h;
Stage #2: With N-acetylphthalimide; Cr(4+)*4NO3(1-); C36H24N8NiO4; C52H44FeN4O8; oxygen; acetic acid at 170℃; under 12001.2 Torr; for 0.6h; Temperature; Pressure; Reagent/catalyst;
A 14.4%
B 85.3%
With zinc(II) oxide In N,N-dimethyl-formamide for 0.133333h; microwave irradiation;A 80%
B 5 % Spectr.
67-56-1

methanol

7658-80-2

2-methylbenzohydrazide

A

118-90-1

ortho-methylbenzoic acid

B

89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With copper diacetate; oxygenA 89%
B 7%
529-20-4

2-methylphenyl aldehyde

A

118-90-1

ortho-methylbenzoic acid

B

95-48-7

ortho-cresol

Conditions
ConditionsYield
With selenium(IV) oxide; dihydrogen peroxide In tetrahydrofuran for 10h; Heating;A 88%
B 9 % Chromat.
With dihydrogen peroxide; methyltrioctylammonium tetrakis(oxodiperoxotungsto)phosphate at 90℃; for 1.5h;A 23%
B 10%
766-47-2

1-ethynyl-2-methylbenzene

118-90-1

ortho-methylbenzoic acid

Conditions
ConditionsYield
Stage #1: 1-ethynyl-2-methylbenzene With tert.-butylhydroperoxide; iron(III) chloride hexahydrate; sodium hydroxide In water at 80℃; for 10h;
Stage #2: With hydrogenchloride In water at 20℃;
88%
1623774-99-1

N-(2-(1-benzyl-1H-1, 2, 3-triazol-4-yl)propan-2-yl)-2-methylbenzamide

118-90-1

ortho-methylbenzoic acid

Conditions
ConditionsYield
With nitrosonium tetrafluoroborate In acetonitrile at 50℃; for 0.166667h;87%
118-90-1

ortho-methylbenzoic acid

64-17-5

ethanol

87-24-1

ethyl 2-methylbenzoate

Conditions
ConditionsYield
With sulfuric acid at 100℃; for 12h;100%
With thionyl chloride at 0 - 80℃; Inert atmosphere;99.5%
With thionyl chloride at 0 - 80℃; Inert atmosphere;99.5%
118-90-1

ortho-methylbenzoic acid

933-88-0

ortho-toluoyl chloride

Conditions
ConditionsYield
With oxalyl dichloride In benzene at 20℃; for 14h;100%
With thionyl chloride Reflux;100%
With thionyl chloride; N,N-dimethyl-formamide at 90℃; for 3h; Concentration; Reagent/catalyst; Temperature;99.7%
118-90-1

ortho-methylbenzoic acid

75-03-6

ethyl iodide

2438-03-1

2-(n-Propyl)-benzoesaeure

Conditions
ConditionsYield
Stage #1: ortho-methylbenzoic acid With sec.-butyllithium In tetrahydrofuran; 1-hexene; cyclohexane at -78 - 20℃;
Stage #2: ethyl iodide In tetrahydrofuran; 1-hexene; cyclohexane at -78 - 20℃;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; cyclohexane
100%
With sec.-butyllithium In cyclohexane for 8h; Ambient temperature;82%
With sec.-butyllithium 1.) THF, cyclohexane, -78 deg C, 1 h, 2.) THF, cyclohexane, RT, 4 h; Yield given. Multistep reaction;
118-90-1

ortho-methylbenzoic acid

chloridotetrakis(acetato)diruthenium(II,III)

Ru2Cl(μ-O2CC6H4-o-Me)4

Conditions
ConditionsYield
In water at 130℃; for 16h; Microwave irradiation;100%
118-90-1

ortho-methylbenzoic acid

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

2,5-dioxopyrrolidin-1-yl 2-methylbenzoate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;100%
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 25℃; for 3h;32.9%
118-90-1

ortho-methylbenzoic acid

607-86-3

2-methylbenzoic anhydride

Conditions
ConditionsYield
With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine In dichloromethane at 20℃; for 0.5h;99%
With 2,6-dimethylpyridine; tris(2,2'-bipyridyl)ruthenium dichloride; carbon tetrabromide; N,N-dimethyl-formamide at 25 - 30℃; for 12h; Inert atmosphere; Photolysis;97%
With Selectfluor; triphenylphosphine In acetonitrile at 20℃; for 4h; Schlenk technique; Inert atmosphere;92%
118-90-1

ortho-methylbenzoic acid

62-53-3

aniline

7055-03-0

2-methyl-N-phenylbenzamide

Conditions
ConditionsYield
Stage #1: ortho-methylbenzoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: aniline With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60℃; Inert atmosphere;
99%
With TEA; 1,2-benzisoxazol-3-yl diphenyl phosphate In various solvent(s) for 2h; Ambient temperature;90%
Stage #1: ortho-methylbenzoic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 3h;
Stage #2: aniline In dichloromethane at 20℃;
31.7%
118-90-1

ortho-methylbenzoic acid

74-88-4

methyl iodide

55262-10-7

1,2-dimethyl-2,5-cyclohexadiene-1-carboxylic acid

Conditions
ConditionsYield
Stage #1: ortho-methylbenzoic acid With ammonia; lithium In tetrahydrofuran at -78℃; Birch reduction; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere;
Stage #3: With hydrogenchloride In tetrahydrofuran; water
99%
Stage #1: ortho-methylbenzoic acid With ammonia; lithium In water at -60℃; for 0.5h; Birch reduction;
Stage #2: methyl iodide In water regioselective reaction;
98%
Stage #1: ortho-methylbenzoic acid With lithium In tetrahydrofuran; ammonia at -78℃;
Stage #2: methyl iodide
91%
(i) Li, liq. NH3, (ii) /BRN= 969135/; Multistep reaction;
118-90-1

ortho-methylbenzoic acid

501-65-5

diphenyl acetylene

8-methyl-3,4-diphenyl-1H-isochromen-1-one

Conditions
ConditionsYield
With dichloro[1,3-di(ethoxycarbonyl)-2,4,5-trimethylcyclopentadienyl]rhodium(III) dimer; copper(II) acetate monohydrate; silver(I) triflimide In dichloromethane at 20℃; for 24h; Sealed tube;99%
With carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; sodium acetate; copper(II) oxide In 2,2,2-trifluoroethanol at 80℃; for 24h; Schlenk technique; Molecular sieve; Inert atmosphere;92%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; C15H23NO4 In 2,2,2-trifluoroethanol at 30℃; for 35h; Reagent/catalyst; Temperature;90%
118-90-1

ortho-methylbenzoic acid

7550-45-0

titanium tetrachloride

4Ti(4+)*5Cl(1-)*7(O2CC6H4CH3)(1-)*2O(2-)={Ti4Cl5(O2CC6H4CH3)7O2}

Conditions
ConditionsYield
In light petroleum byproducts: CH3C6H4COCl, HCl; exclusion of air and moisture, addn. of TiCl4 (by syringe) to the org. compound stirred in light petroleum (b.p. 100-120°C) at 0°C, slowly warming to room temp., then heating to reflux, 4 h, pptn.; cooling, filtration, washing (hexane), drying in vac. for 2 h, elem. anal.;99%
In light petroleum compds. are heated under reflux at 100-120°C;; elem. anal.;;>99
118-90-1

ortho-methylbenzoic acid

105-58-8

Diethyl carbonate

87-24-1

ethyl 2-methylbenzoate

Conditions
ConditionsYield
With sulfuric acid at 110 - 120℃; for 13h; Neat (no solvent);99%
118-90-1

ortho-methylbenzoic acid

75-09-2

dichloromethane

144168-19-4

bis(2-methylbenzoyloxy)methane

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 60℃; for 3h; Reagent/catalyst; Solvent;99%
With potassium carbonate In dimethyl sulfoxide at 130℃; for 5h;98%
118-90-1

ortho-methylbenzoic acid

696-62-8

para-iodoanisole

4'-methoxy-3-methyl-[1,1'-biphenyl]-2-carboxylic acid

Conditions
ConditionsYield
With C30H54N6Ru(2+)*2BF4(1-); potassium perfluoro-tert-butoxide; potassium carbonate at 140℃; for 16h; Reagent/catalyst; Temperature; Glovebox; Inert atmosphere;99%
With palladium diacetate; caesium carbonate; N-acetyl-L-isoleucine; silver carbonate at 30℃; for 36h; Schlenk technique; Inert atmosphere;59%
With dipotassium hydrogenphosphate; sodium acetate; palladium diacetate; silver carbonate In tert-butyl alcohol at 140℃; for 48h;
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; potassium carbonate; tricyclohexylphosphine In 1-methyl-pyrrolidin-2-one at 100℃; for 24h; Inert atmosphere; Glovebox; Sealed tube;
1824-81-3

2-Amino-6-methylpyridine

118-90-1

ortho-methylbenzoic acid

2-methyl-N-(6-methylpyridin-2-yl)benzamide

Conditions
ConditionsYield
Stage #1: ortho-methylbenzoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: 2-Amino-6-methylpyridine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60℃; Inert atmosphere;
99%
118-90-1

ortho-methylbenzoic acid

15796-89-1

N-methyl-N-phenylmethacrylamide

1,3-dimethyl-3-(2-oxo-2-(o-tolyl)eth yl)indolin-2-one

Conditions
ConditionsYield
With 2,6-dimethylpyridine; di-tert-butyl dicarbonate; tris[2-phenylpyridinato-C2,N]iridium(III); magnesium chloride In N,N-dimethyl-formamide at 20℃; for 48h; Sealed tube; Inert atmosphere; UV-irradiation;99%
118-90-1

ortho-methylbenzoic acid

292638-85-8

acrylic acid methyl ester

methyl 2-(4-methyl-3-oxo-1,3-dihydroisobenzofuran-1-yl)acetate

Conditions
ConditionsYield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; potassium acetate In water at 100℃; for 24h; Green chemistry;99%
With C45H51Cl2CuN4P4Ru(1+)*BF4(1-); sodium acetate In water at 100℃; for 12h; Inert atmosphere; Schlenk technique;90%
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; oxygen; potassium acetate In butan-1-ol at 80℃; under 760.051 Torr; for 18h; Schlenk technique; chemoselective reaction;72%
118-90-1

ortho-methylbenzoic acid

682-30-4

Diethyl vinylphosphonate

diethyl ((4-methyl-3-oxo-1,3-dihydroisobenzofuran-1-yl)methyl)phosphonate

Conditions
ConditionsYield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; potassium acetate In water at 100℃; for 24h; Catalytic behavior; Reagent/catalyst; Temperature; Green chemistry;99%
118-90-1

ortho-methylbenzoic acid

771-61-9

2,3,4,5,6-pentafluorophenol

pentafluorophenyl 2-methylbenzoate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;99%
118-90-1

ortho-methylbenzoic acid

616-38-6

carbonic acid dimethyl ester

89-71-4

2-Methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid; acetic acid at 85 - 90℃; for 12h; Neat (no solvent); Large scale reaction;98.34%
118-90-1

ortho-methylbenzoic acid

108-98-5

thiophenol

35092-37-6

2-Methyl-thiobenzoesaeure-S-phenylester

Conditions
ConditionsYield
With pyridine; O-phenyl phosphorodichloridate In 1,2-dimethoxyethane for 16h; Ambient temperature;98%
Stage #1: ortho-methylbenzoic acid With aluminum (III) chloride In ethyl acetate at 0℃; for 2h;
Stage #2: thiophenol With zinc(II) chloride In ethyl acetate for 4h; Reflux;
85%
(i) SOCl2, (ii) /BRN= 506523/; Multistep reaction;
Stage #1: ortho-methylbenzoic acid With dmap; 3-((1H-benzo[d][1,2,3]triazol-5-yl)methyl)-1,2-dimethyl-1H-imidazole-3-ium hexafluorophosphate; dicyclohexyl-carbodiimide In acetonitrile at 20℃; Green chemistry;
Stage #2: thiophenol With dmap In water at 100℃; for 0.166667h; Microwave irradiation; Green chemistry;
118-90-1

ortho-methylbenzoic acid

54811-50-6

2-iodo-6-methylbenzoic acid

Conditions
ConditionsYield
With N-iodo-succinimide; palladium diacetate In N,N-dimethyl-formamide at 100℃; for 16h; Inert atmosphere;98%
With N-iodo-succinimide; [Ir(III)(η5-pentamethylcyclopentadienyl)(H2O)3](SO4) at 40℃; for 16h; Reagent/catalyst; Temperature;98%
With N-iodo-succinimide; palladium diacetate In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; N,N-dimethyl-formamide95%
118-90-1

ortho-methylbenzoic acid

74-83-9

methyl bromide

55262-10-7

1,2-dimethyl-2,5-cyclohexadiene-1-carboxylic acid

Conditions
ConditionsYield
Stage #1: ortho-methylbenzoic acid With ammonia; lithium at -60℃; Birch reduction;
Stage #2: methyl bromide at -60 - 20℃;
98%
With ammonia; lithium 1.) -60 deg C, 20 min, 2.) from -60 deg C to 25 deg C, 16 h; Yield given. Multistep reaction;
118-90-1

ortho-methylbenzoic acid

75-26-3

isopropyl bromide

31689-42-6

2-methyl-1-(1-methylethyl)cyclohexa-2,5-diene-1-carboxylic acid

Conditions
ConditionsYield
Stage #1: ortho-methylbenzoic acid With ammonia; lithium at -60℃; Birch reduction;
Stage #2: isopropyl bromide at -60 - 20℃;
98%
Stage #1: ortho-methylbenzoic acid With ammonia; lithium In water at -60℃; for 0.5h; Birch reduction;
Stage #2: isopropyl bromide In water regioselective reaction;
98%
With ammonia; lithium 1.) -60 deg C, 20 min, 2.) from -60 deg C to 25 deg C, 16 h; Yield given. Multistep reaction;
Stage #1: ortho-methylbenzoic acid With ammonia; lithium at -78℃; for 1h;
Stage #2: isopropyl bromide at -78℃; for 0.25h;
118-90-1

ortho-methylbenzoic acid

19227-13-5

(Z)-N'-hydroxy-4-methylbenzimidamide

5-o-tolyl-3-p-tolyl-[1,2,4]oxadiazole

Conditions
ConditionsYield
Stage #1: ortho-methylbenzoic acid With PS-PPh3; trichloroacetonitrile In tetrahydrofuran at 100℃; for 0.0833333h; microwave irradiation;
Stage #2: (Z)-N'-hydroxy-4-methylbenzimidamide With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 150℃; for 0.25h; microwave irradiation;
98%
118-90-1

ortho-methylbenzoic acid

98-85-1, 13323-81-4

1-Phenylethanol

51801-00-4

1-phenylethyl 2-methylbenzoate

Conditions
ConditionsYield
With potassium hydroxide98%
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Chemistry

Molecular Structure of o-Toluic acid (CAS NO.118-90-1):

IUPAC Name: 2-Methylbenzoic acid 
Molecular Formula: C8H8O2
Molecular Weight: 136.15 
EINECS: 204-284-9
Melting Point: 103 °C
Index of Refraction: 1.556
Molar Refractivity: 38 cm3
Molar Volume: 118.2 cm3
Surface Tension: 45.4 dyne/cm
Density: 1.151 g/cm3
Flash Point: 118.8 °C
Enthalpy of Vaporization: 52.68 kJ/mol
Boiling Point: 260.9 °C at 760 mmHg
Vapour Pressure: 0.00603 mmHg at 25 °C
Water Solubility: <0.1 g/100 mL at 19 °C
Appearance: Pale yellow crystals or off-white flaky solid.
Product Categories: Organic acids
Classification Code: Drug / Therapeutic Agent
Canonical SMILES: CC1=CC=CC=C1C(=O)O
InChI: InChI=1S/C8H8O2/c1-6-4-2-3-5-7(6)8(9)10/h2-5H,1H3,(H,9,10)
InChIKey: ZWLPBLYKEWSWPD-UHFFFAOYSA-N
Stability: Stable. Combustible. Incompatible with strong oxidizing agents, strong bases.

History

o-Toluic acid was first noticed by Sir William Ramsay, credited discoverer of the noble gases and winner of the 1904 Nobel Prize in Chemistry.

Uses

 o-Toluic acid (CAS NO.118-90-1) can be used for spices, m-cresol, pesticides fungicides phosphorylaminopropyl, vinyl chloride polymerization initiator MBPO, color film reagent organic synthesis intermediates.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 422mg/kg (422mg/kg) BEHAVIORAL: REGIDITY

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Journal of Medicinal Chemistry. Vol. 11, Pg. 1020, 1968.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Safety Information of o-Toluic acid (CAS NO.118-90-1):
Hazard Codes: HarmfulXn,IrritantXi
Risk Statements: 36/37/38-22 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R22:Harmful if swallowed.
Safety Statements: 26-36-22 
S22:Do not breathe dust. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS: XU1400000
Poison by ingestion. When heated to decomposition it emits acrid smoke and irritating fumes.

Specification

 o-Toluic acid (CAS NO.118-90-1), its Synonyms are 2-Methylbenzoic acid ; Orthotoluic acid ; Toluic acid ; o-Methylbenzoic acid ; o-Toluylic acid ; Benzoic acid, 2-methyl- .

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