ChemicalBook > CAS DataBase List > METHYL 2-METHOXY-4-METHYLBENZOATE

METHYL 2-METHOXY-4-METHYLBENZOATE

Product Name: METHYL 2-METHOXY-4-METHYLBENZOATE
CAS No.: 81245-24-1
Chemical Name: METHYL 2-METHOXY-4-METHYLBENZOATE
Synonyms: Methyl o-methoxy-p-toluate;METHYL 2-METHOXY-4-METHYLBENZOATE;Methyl 4-Methyl-2-Methoxybenzoate;2-Methoxy-4-Methylbenzoic acid Methyl ester;Benzoic acid, 2-Methoxy-4-Methyl-, Methyl ester;2-methoxy-4-methyl-Benzoic acid methyl ester (9CI ACI);Benzoic acid, 2-methoxy-4-methyl-, methyl ester (9CI, ACI)
CBNumber: CB4712301
Molecular Formula: C10H12O3
Formula Weight: 180.2
MOL File: Mol file

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METHYL 2-METHOXY-4-METHYLBENZOATE Property

Melting point:: 29℃
Boiling point:: 263-265℃
Density: 1.075±0.06 g/cm3(Predicted)
refractive index: 1.5230 (589.3 nm 18℃)
storage temp.: Sealed in dry,Room Temperature
Appearance: Colorless to light yellow Liquid
InChI: InChI=1S/C10H12O3/c1-7-4-5-8(10(11)13-3)9(6-7)12-2/h4-6H,1-3H3
InChIKey: LHNVKRSDQCCHEK-UHFFFAOYSA-N
SMILES: C(OC)(=O)C1=CC=C(C)C=C1OC

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Safety

HS Code: 2918290090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H227Combustible liquid

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC

Product number: M338578
Product name: Methyl2-Methoxy-4-methylbenzoate
Packaging: 50mg
Price: $60
Updated: 2021/12/16

AK Scientific

Product number: W8578
Product name: Methyl2-methoxy-4-methylbenzoate
Packaging: 1g
Price: $42
Updated: 2021/12/16

ChemScene

Product number: CS-M1058
Product name: methyl2-methoxy-4-methylbenzoate
Purity: >97.0%
Packaging: 5g
Price: $55
Updated: 2021/12/16

AK Scientific

Product number: W8578
Product name: Methyl2-methoxy-4-methylbenzoate
Packaging: 5g
Price: $78
Updated: 2021/12/16

ChemScene

Product number: CS-M1058
Product name: methyl2-methoxy-4-methylbenzoate
Purity: >97.0%
Packaging: 10g
Price: $100
Updated: 2021/12/16

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METHYL 2-METHOXY-4-METHYLBENZOATE Chemical Properties,Usage,Production

Synthesis

50-85-1

77-78-1

81245-24-1

1. To a 1-liter three-necked round-bottomed flask (equipped with a dropping funnel, condenser, and magnetic stirring bar) were added 4-methylsalicylic acid (50 g, 0.33 mol), K2CO3 (91.1 g, 0.66 mol, 2 eq.), and anhydrous acetone. The mixture was heated to reflux while dimethyl sulfate (112.3 g, 0.891 mol, 2.7 eq.) was added dropwise. The reaction mixture was refluxed for about 14 hours (completion of the reaction was monitored by TLC). The inorganic salt was removed by filtration and the THF filtrate was evaporated under reduced pressure to give a yellow oil. 2. The residue was dissolved in a mixture of 400 mL of methanol and concentrated NH4OH (115 mL). Stir for 30 minutes at room temperature. The methanol was removed by distillation, the residue was diluted with water (500 ml) and the oily product was extracted with ether (3 x 300 ml). The organic extracts were combined, dried with sodium sulfate, and the ether was removed under reduced pressure to give pure methyl 2-methoxy-4-methylbenzoate (57 g, 96% yield) as a yellow oil. 3. To a dry 2-liter, three-necked, round-bottomed flask (equipped with an argon inlet, a thermometer, a magnetic stirring bar, and a septum) was added THF (220 ml) and diisopropylamine (54.6 ml, 0.39 mol, 1.2 eq.). The mixture was cooled to -50 °C and a solution of 2.5 M n-BuLi (156 mL, 0.39 mol, 1.2 eq.) was slowly added through the cannula. After stirring at -50 °C for 30 min, the resulting LDA solution was cooled to -78 °C, HMPA (67.8 mL, 0.39 mol, 1.2 eq.) was added, followed by a solution of methyl 2-methoxy-4-methylbenzoate (57 g, 0.32 mol) in THF (220 mL), keeping the temperature at -78 °C. The reaction mixture was stirred at -78 °C for an additional 2 h and then transferred to a flask containing 100 g of dry ice and THF (200 mL). After stirring at -78 °C for 30 min, the mixture was slowly warmed to room temperature and poured into water (1.5 liters). The organic layer was separated and the aqueous layer was further extracted with ether (3 x 1 liter). The aqueous layer was acidified with 10% H2SO4 (150 ml) and the reaction product was extracted with CH2Cl2 (3 x 1.5 liters). The organic extracts were combined, dried with anhydrous Na2SO4, the solvent was removed under reduced pressure, and the crude product was purified by fast chromatography (eluent: EtOAc:hexane 3:7) and recrystallized from CH2Cl2:hexane 1:1 to give pure methyl 4-carboxymethyl-2-methoxybenzoate (38.8 g, 54.7% yield). 4. Methyl 4-carboxymethyl-2-methoxybenzoate (12.7 g, 0.0567 mol) was dissolved in glacial acetic acid (100 mL) and bromine (3.2 mL, 0.0624 mol, 1.1 eq.) was added dropwise via a syringe, maintaining the internal temperature at room temperature. After stirring for 4 h, the AcOH was removed by evaporation and the orange oil was evaporated twice with toluene to give an orange solid. The substance was ground with CH2Cl2 and filtered to remove some of the precipitated product. The remaining product in the filtrate was concentrated on a silica gel column, eluting with EtOAc:hexane (6:4) containing 1% AcOH. Further purification by a second chromatography and recrystallization from EtOAc:hexane gave pure methyl 5-bromo-4-carboxymethyl-2-methoxybenzoate (9 g total, 52% yield) as a white solid.

References

[1] Patent: WO2004/108673, 2004, A2. Location in patent: Page 45-46
[2] Bioorganic and medicinal chemistry, 2002, vol. 10, # 9, p. 3013 - 3021
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2334 - 2356
[4] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 19, p. 4987 - 4993
[5] Patent: WO2004/65367, 2004, A1. Location in patent: Page 152 - 153; 157

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View Lastest Price from METHYL 2-METHOXY-4-METHYLBENZOATE manufacturers

Zhuozhou Wenxi import and Export Co., Ltd

Product: METHYL 2-METHOXY-4-METHYLBENZOATE 81245-24-1
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-07-11

Zhuozhou Wenxi import and Export Co., Ltd

Product: METHYL 2-METHOXY-4-METHYLBENZOATE 81245-24-1
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-07-09

Career Henan Chemical Co

Product: METHYL 2-METHOXY-4-METHYLBENZOATE 81245-24-1
Price: US $1.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 20KG
Release date: 2018-08-14

81245-24-1, METHYL 2-METHOXY-4-METHYLBENZOATERelated Search:

METHYL 2-METHOXY-4-METHYLBENZOATE

2-Methoxy-4-Methylbenzoic acid Methyl ester

Methyl 4-Methyl-2-Methoxybenzoate

Methyl o-methoxy-p-toluate

Benzoic acid, 2-Methoxy-4-Methyl-, Methyl ester

Benzoic acid, 2-methoxy-4-methyl-, methyl ester (9CI, ACI)

2-methoxy-4-methyl-Benzoic acid methyl ester (9CI ACI)

81245-24-1