3-Methoxy-2-methylbenzoic acid

Base Information

• Chemical Name: 3-Methoxy-2-methylbenzoic acid
• CAS No.: 55289-06-0
• Molecular Formula: C9H10O3
• Molecular Weight: 166.177
• Hs Code.: 2918990090
• European Community (EC) Number: 676-588-3
• DSSTox Substance ID: DTXSID00427374
• Nikkaji Number: J623.098I
• Wikidata: Q72490341
• Mol file: 55289-06-0.mol

Synonyms:3-methoxy-2-methylbenzoic acid;55289-06-0;3-Methoxy-o-toluic Acid;3-Methoxy-2-methylbenzoicacid;2-Methyl-m-anisic Acid;Benzoic acid, 3-methoxy-2-methyl-;2-METHYL-3-METHOXYBENZOIC ACID;MFCD02094039;3-methoxy-2-methyl-benzoic Acid;SCHEMBL311839;2-methyl-3-methoxy-benzoic acid;3-Methoxy-2-methyl benzoic acid;DTXSID00427374;2-methyl-3-methoxyl-benzoic acid;JPCISVSOTKMFPG-UHFFFAOYSA-N;BCP19993;AKOS005259940;AC-3996;AM84144;CS-W002884;MF-0044;SB11451;SY020989;3-methoxy-2-methylbenzoic acid, AldrichCPR;A8005;FT-0615969;M2217;EN300-299886;A1-00444;J-512749

Chemical Property of 3-Methoxy-2-methylbenzoic acid

Chemical Property:

• Melting Point: 147.0 to 151.0 °C
• Boiling Point: 297 °C at 760 mmHg
• PKA: 3.83±0.10(Predicted)
• Flash Point: 119.9 °C
• PSA: 46.53000
• Density: 1.168 g/cm³
• LogP: 1.70180
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Soluble in methanol. Insoluble in water.
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 166.062994177
• Heavy Atom Count: 12
• Complexity: 167

Purity/Quality:

99% ^*data from raw suppliers

3-Methoxy-2-methylbenzoic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: R36/37/38:Irritating to eyes, respiratory system and skin.
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=CC=C1OC)C(=O)O
• Uses: 3-Methoxy-2-methylbenzoic acid is used as a Corey-Bakshi-Shibata oxazaborolidine catalyst for asymmetric reduction and asymmetric synthesis. It is used in the asymmetric reduction of prochiral ketones. Other applications include the enantioselective synthesis of α-hydroxy acids, α-amino acids, C2 symmetrical ferrocenyl diols and propargyl alcohols. It is also used in desymmetrizing reduction leading to (S)-4-hydroxycyclohexenone.

Technology Process of 3-Methoxy-2-methylbenzoic acid

There total 38 articles about 3-Methoxy-2-methylbenzoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

metallic magnesium powder + 1-chloro-3-methoxy-2-methylbenzene (3260-88-6) + isopropyl bromide (75-26-3) → 3-methoxy-2-methylbenzoic acid (55289-06-0)

Guidance literature:

With hydrogenchloride; sodium hydroxide; In tetrahydrofuran; water; toluene;

Reference yield: 90.4%

3-hydroxy 2-methylbenzoic acid (603-80-5) + dimethyl sulfate (77-78-1) → 3-methoxy-2-methylbenzoic acid (55289-06-0)

Guidance literature:

3-hydroxy 2-methylbenzoic acid; With sodium hydroxide; In water; at 40 ℃; pH=5.5 - 10.5;

dimethyl sulfate; With sodium hydroxide; In water; at 40 - 45 ℃; for 4h; pH=10.4 - 10.6;

With sodium hydroxide; sulfuric acid; more than 3 stages;

Reference yield: 80.0%

3-chloro-2-methylbenzoic acid (7499-08-3) + sodium methylate (124-41-4) → 3-methoxy-2-methylbenzoic acid (55289-06-0)

Guidance literature:

With dimethyl sulfoxide; copper(l) chloride; In methanol; at 100 - 105 ℃; for 2h; Temperature; Reagent/catalyst;

upstream raw materials:

1-bromo-3-methoxy-2-methylbenzene

3-methoxy-2-methylbenzoic acid methyl ester

3-methoxy-2-methylbenzonitrile

3-hydroxy 2-methylbenzoic acid

Downstream raw materials:

2-bromomethyl-3-methoxybenzoic acid

2-(bromomethyl)-3-methoxybenzoic acid ethyl ester

1-(chloromethyl)-3-methoxy-2-methylbenzene

3-<3-Methoxy-2-methyl-benzyl>-2-methyl-4-oxo-cyclohexan-1-carbonsaeure-ethylester

Refernces

• 1、 -. "Preparation method of 6-chloro-2-methoxytoluene and synthesis process of methoxyfenozide". Paragraph 0074-0077; 0096-0100. . Retrieved 2021/08/14.
• 2、 -. "2-methyl-3-methoxybenzoyl chloride synthesizing process". Paragraph 0018; 0022; 0023; 0027; 0028. . Retrieved 2019/03/15.