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99-75-2

Basic Information
CAS No.: 99-75-2
Name: Methyl 4-methylbenzoate
Article Data: 455
Molecular Structure:
Molecular Structure of 99-75-2 (Methyl 4-methylbenzoate)
Formula: C9H10O2
Molecular Weight: 150.177
Synonyms: p-Toluicacid, methyl ester (6CI,8CI);4-(Methoxycarbonyl)toluene;4-Methylbenzoic acidmethyl ester;
EINECS: 202-784-1
Density: 1.045 g/cm3
Melting Point: 32-35 °C(lit.)
Boiling Point: 222.5 °C at 760 mmHg
Flash Point: 90.6 °C
Solubility: <0.1 g/100 mL at 22 °C in water
Appearance: crystals, melting is a colorless liquid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 37/39-26-36
PSA: 26.30000
LogP: 1.78160
Synthetic route
67-56-1

methanol

99-94-5

p-Toluic acid

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%
99-94-5

p-Toluic acid

74-88-4

methyl iodide

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;
67-56-1

methanol

201230-82-2

carbon monoxide

624-31-7

4-tolyl iodide

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%
67-56-1

methanol

589-18-4

4-Methylbenzyl alcohol

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%
67-56-1

methanol

619-55-6

para-methylbenzamide

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%
99-94-5

p-Toluic acid

616-38-6

carbonic acid dimethyl 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%
67-56-1

methanol

104-87-0

4-methyl-benzaldehyde

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%
34672-84-9

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

99-94-5

p-Toluic acid

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%
67-56-1

methanol

70971-70-9

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

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%
122-00-9

para-methylacetophenone

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%
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Chemistry

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

Uses

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

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.

Consensus Reports

Reported in EPA TSCA Inventory.

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)

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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