Product Name

  • Name

    Methyl 4-methylbenzoate

  • EINECS 202-784-1
  • CAS No. 99-75-2
  • Article Data455
  • CAS DataBase
  • Density 1.045 g/cm3
  • Solubility <0.1 g/100 mL at 22 °C in water
  • Melting Point 32-35 °C(lit.)
  • Formula C9H10O2
  • Boiling Point 222.5 °C at 760 mmHg
  • Molecular Weight 150.177
  • Flash Point 90.6 °C
  • Transport Information
  • Appearance crystals, melting is a colorless liquid
  • Safety 37/39-26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 99-75-2 (Methyl 4-methylbenzoate)
  • Hazard Symbols IrritantXi
  • Synonyms p-Toluicacid, methyl ester (6CI,8CI);4-(Methoxycarbonyl)toluene;4-Methylbenzoic acidmethyl ester;
  • PSA 26.30000
  • LogP 1.78160

Synthetic route

methanol
67-56-1

methanol

p-Toluic acid
99-94-5

p-Toluic acid

4-methyl-benzoic acid methyl ester
99-75-2

4-methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With boron trifluoride at 65℃; for 0.333333h;100%
With sulfuric acid for 4h; Reflux;100%
With sulfuric acid Fischer-Speier esterification method; Reflux;100%
p-Toluic acid
99-94-5

p-Toluic acid

methyl iodide
74-88-4

methyl iodide

4-methyl-benzoic acid methyl ester
99-75-2

4-methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;100%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 5h;
With N'',N'''''-1,8-naphthalenediyl bis[N,N,N',N'-tetramethyl]guanidine In N,N-dimethyl-formamide at 20℃; Kinetics;
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 10h; Inert atmosphere; Sealed tube;
methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

4-tolyl iodide
624-31-7

4-tolyl iodide

4-methyl-benzoic acid methyl ester
99-75-2

4-methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With triethylamine at 100℃; under 3750.38 Torr; for 1.5h; Inert atmosphere;99%
With triethylamine at 100℃; under 3750.38 Torr; for 1h; Autoclave;98%
With palladium diacetate; caesium carbonate; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane In N,N-dimethyl-formamide at 80℃; under 2327.23 Torr;97%
...Expand
methanol
67-56-1

methanol

4-Methylbenzyl alcohol
589-18-4

4-Methylbenzyl alcohol

4-methyl-benzoic acid methyl ester
99-75-2

4-methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; benzyl chloride In tetrahydrofuran at 65 - 70℃; for 20h; Concentration; Inert atmosphere; Schlenk technique;99%
With potassium carbonate at 60℃; under 750.075 Torr; for 2h; Temperature; Pressure;98.8%
With palladium 10% on activated carbon; oxygen; sodium carbonate at 120℃; under 15001.5 Torr; for 1.5h; Microwave irradiation; Green chemistry;97%
methanol
67-56-1

methanol

para-methylbenzamide
619-55-6

para-methylbenzamide

4-methyl-benzoic acid methyl ester
99-75-2

4-methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With thionyl chloride at 0 - 55℃; for 6h;99%
With potassium hydrogensulfate at 65℃; for 48h;91%
p-Toluic acid
99-94-5

p-Toluic acid

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

4-methyl-benzoic acid methyl ester
99-75-2

4-methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With diiron nonacarbonyl at 180℃; for 1h; Sealed tube;99%
With sulfuric acid at 80 - 85℃; for 10h; Neat (no solvent);95.7%
methanol
67-56-1

methanol

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

4-methyl-benzoic acid methyl ester
99-75-2

4-methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With perchloric acid; sodium percarbonate; vanadia for 0.75h; Cooling;98%
With palladium 10% on activated carbon; oxygen; sodium carbonate at 100℃; under 15001.5 Torr; for 1h; Microwave irradiation; Green chemistry;98%
With oxygen; potassium carbonate at 60℃; for 2h; Autoclave;97%
1-methoxy-2,2,6,6-tetramethylpiperidine
34672-84-9

1-methoxy-2,2,6,6-tetramethylpiperidine

p-Toluic acid
99-94-5

p-Toluic acid

4-methyl-benzoic acid methyl ester
99-75-2

4-methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With 2,6-di-tert-butyl-pyridine In acetonitrile at 21 - 25℃; for 18h; Electrochemical reaction;97%
methanol
67-56-1

methanol

(1H-pyrrol-1-yl)(p-tolyl)methanone
70971-70-9

(1H-pyrrol-1-yl)(p-tolyl)methanone

4-methyl-benzoic acid methyl ester
99-75-2

4-methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)nickel (0) In toluene at 20℃; for 1h; Sealed tube; chemoselective reaction;97%
para-methylacetophenone
122-00-9

para-methylacetophenone

4-methyl-benzoic acid methyl ester
99-75-2

4-methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With Co4HP2Mo15V3O62; N-(4-sulfonic acid)butyl triethylammonium tetrafluoroborate; dihydrogen peroxide at 50℃; for 4h; Green chemistry;96%
With oxygen; 1-(n-butyl)-3-methylimidazolium triflate at 20℃; for 0.333333h; Baeyer-Villiger Ketone Oxidation; Electrochemical reaction; Green chemistry;95%
4-methylbenzaldehyde dimethylacetal
3395-83-3

4-methylbenzaldehyde dimethylacetal

4-methyl-benzoic acid methyl ester
99-75-2

4-methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With 3,3-dimethyldioxirane In acetone at 25℃; Kinetics;95%
With 3,3-dimethyldioxirane In acetone at 25℃;95%
With boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid In chloroform for 1h; Ambient temperature; Yield given;
4-methyl-1-[dimethoxy(methylthio)methyl]benzene

4-methyl-1-[dimethoxy(methylthio)methyl]benzene

A

4-methyl-benzoic acid methyl ester
99-75-2

4-methyl-benzoic acid methyl ester

B

1-(methanesulfinyl-dimethoxy-methyl)-4-methyl-benzene

1-(methanesulfinyl-dimethoxy-methyl)-4-methyl-benzene

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 3h;A 95%
B 5%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at -78℃; for 1h;A 49%
B 9%
4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

4-methyl-benzoic acid methyl ester
99-75-2

4-methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With maghemite-supported nanogold; oxygen; potassium carbonate In methanol at 80℃; for 7h; Green chemistry;95%
Multi-step reaction with 2 steps
1: 55 - 60 °C
2: dihydrogen peroxide / 8 h / 55 - 60 °C
View Scheme
Multi-step reaction with 2 steps
1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; 2,2':6,2''-terpyridine; sodium hydrogencarbonate / 6 h / 90 °C / Sealed tube; Green chemistry
2: trichloro(2,2':6',2''-terpyridine)rhodium(III); sodium hydrogencarbonate / 12 h / 90 °C / Green chemistry
View Scheme
Multi-step reaction with 2 steps
1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; 2,2':6,2''-terpyridine; sodium hydroxide; methanol / 6 h / 90 °C / Sealed tube; Green chemistry
2: trichloro(2,2':6',2''-terpyridine)rhodium(III); sodium hydrogencarbonate / 12 h / 90 °C / Green chemistry
View Scheme
Multi-step reaction with 2 steps
1: recombinant aldehyde dehydrogenase from bovine lens; 1,4-dithio-D,L-threitol; water‐forming NADH oxidase from Streptococcus mutans; NAD / aq. phosphate buffer / 4 h / 40 °C / pH 8.5 / Green chemistry; Enzymatic reaction
2: methanol; ethyl acetate / 1 h / 30 °C
View Scheme
methyl 4-formylbenzoate
1571-08-0

methyl 4-formylbenzoate

4-methyl-benzoic acid methyl ester
99-75-2

4-methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With hydrogen In ethanol at 80℃; under 2250.23 Torr; for 2h; Inert atmosphere;95%

Methyl 4-methylbenzoate Chemical Properties

IUPAC Name: Methyl 4-methylbenzoate
Molecular Formula: C9H10O2
Molecule structure of Methyl 4-toluate (CAS NO.99-75-2):

Molecular Weight: 150.17 g/mol
Product Categories: CARBOXYLICESTER; Aromatic Esters; Organics; Acids & Esters; C8 to C9; Carbonyl Compounds; Esters
EINECS: 202-784-1 
Surface Tension: 35.1 dyne/cm 
Density: 1.045 g/ml  
Melting Point: 32-35 °C(lit.)
Flash Point: 90.6 °C 
Enthalpy of Vaporization: 45.9 kJ/mol 
Boiling Point: 222.5 °C at 760 mmHg 
Vapour Pressure: 0.101 mmHg at 25°C 
XLogP3: 2.7
H-Bond Acceptor: 2
Rotatable Bond Count: 2
Tautomer Count: 3
Exact Mass: 150.06808
MonoIsotopic Mass: 150.06808
Topological Polar Surface Area: 26.3
Heavy Atom Count: 11 
Canonical SMILES: CC1=CC=C(C=C1)C(=O)OC
InChI: InChI=1S/C9H10O2/c1-7-3-5-8(6-4-7)9(10)11-2/h3-6H,1-2H3
InChIKey: QSSJZLPUHJDYKF-UHFFFAOYSA-N

Methyl 4-methylbenzoate Uses

The Methyl 4-toluate (CAS NO.99-75-2) is used as a pharmaceutical intermediate.

Methyl 4-methylbenzoate Toxicity Data With Reference

1.    

skn-rbt 500 mg/24H MOD

     FCTXAV    Food and Cosmetics Toxicology. 17 (1979),873.
2.    

orl-rat LD50:3300 mg/kg

     FCTXAV    Food and Cosmetics Toxicology. 17 (1979),873.
3.    

orl-mus LD50:3800 mg/kg

     85GMAT    Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure Izmerov, N.F., et al.,Moscow, USSR.: Centre of International Projects, GKNT,1982,87.
4.    

ipr-mus LD50:1250 mg/kg

     85GMAT    Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure Izmerov, N.F., et al.,Moscow, USSR.: Centre of International Projects, GKNT,1982,87.

Methyl 4-methylbenzoate Consensus Reports

Reported in EPA TSCA Inventory.

Methyl 4-methylbenzoate Safety Profile

Moderately toxic by ingestion and intraperitoneal routes. A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes: IrritantXi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin ;
Safety Statements: 37/39-26-36
S37/39:Wear suitable gloves and eye/face protection ;
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice ;
S36:Wear suitable protective clothing ;
WGK Germany: 2
RTECS: XU2150000
HS Code: 29163900
Hazardous Substances Data: 99-75-2(Hazardous Substances Data)

Methyl 4-methylbenzoate Specification

 Methyl 4-toluate (CAS NO.99-75-2) is also named as 4-(Methoxycarbonyl)toluene ; 4-09-00-01726 (Beilstein Handbook Reference) ; 4-Methylbenzoic acid methyl ester ; AI3-04243 ; BRN 1100609 ; CCRIS 6071 ; HSDB 5327 ; Methyl 4-methylbenzoate ; Methyl p-methylbenzoate ; Methyl p-toluate ; Methyl p-toluenecarboxylate ; Methyl-p-toluate ; NSC 24761 ; p(Methoxycarbonyl)toluene ; p-Carbomethoxytoluene . Methyl 4-toluate (CAS NO.99-75-2) is white low melting crystalline solid. It is an ester. Esters react with acids to liberate heat along with alcohols and acids.  Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. 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.

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