2-Methylhippuric acid

Base Information

• Chemical Name: 2-Methylhippuric acid
• CAS No.: 42013-20-7
• Molecular Formula: C10H11NO3
• Molecular Weight: 193.202
• Hs Code.: 2924299090
• European Community (EC) Number: 255-622-7
• NSC Number: 163983
• UNII: J043BCI40Z
• DSSTox Substance ID: DTXSID60194818
• Nikkaji Number: J47.329D
• Wikidata: Q22132784
• NCI Thesaurus Code: C173416
• Metabolomics Workbench ID: 41498
• ChEMBL ID: CHEMBL457228
• Mol file: 42013-20-7.mol

Synonyms:2-methylhippuric acid;o-methylhippuric acid;ortho-methylhippuric acid

Chemical Property of 2-Methylhippuric acid

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 8.89E-08mmHg at 25°C
• Melting Point: 161-164 °C(lit.)
• Refractive Index: 1.5300 (estimate)
• Boiling Point: 419.2 °C at 760 mmHg
• PKA: 3.71±0.10(Predicted)
• Flash Point: 207.3 °C
• PSA: 66.40000
• Density: 1.229 g/cm³
• LogP: 1.20030
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 193.07389321
• Heavy Atom Count: 14
• Complexity: 227

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Methyl hippuric acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=CC=C1C(=O)NCC(=O)O
• Uses: The main metabolite of o-xylene.

Technology Process of 2-Methylhippuric acid

There total 4 articles about 2-Methylhippuric 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:

ortho-toluoyl chloride (933-88-0) + glycine (56-40-6,18875-39-3,25718-94-9) → 2-[(2-methylphenyl)formamido]acetic acid (42013-20-7)

Guidance literature:

With sodium hydroxide;

Reference yield:

N-o-toluoyl-glycine ethyl ester (78973-74-7) → 2-[(2-methylphenyl)formamido]acetic acid (42013-20-7)

Guidance literature:

With water; sodium hydroxide; In 2-methyltetrahydrofuran; at 25 - 28 ℃; for 1h;

DOI:10.1021/op100032s

Reference yield:

ortho-toluoyl chloride (933-88-0) → 2-[(2-methylphenyl)formamido]acetic acid (42013-20-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydrogencarbonate / 2-methyltetrahydrofuran; water / 0.5 h / Cooling

1.2: 3 h / 10 °C / Cooling

2.1: water; sodium hydroxide / 2-methyltetrahydrofuran / 1 h / 25 - 28 °C

With water; sodium hydrogencarbonate; sodium hydroxide; In 2-methyltetrahydrofuran; water; 1.2: Schotten-Baumann reaction;

DOI:10.1021/op100032s

upstream raw materials:

ortho-toluoyl chloride

glycine

N-o-toluoyl-glycine ethyl ester

Downstream raw materials:

[(2-methylbenzoyl)amino]methyl acetate

C₁₂H₁₃NO₄

4-(4-nitrobenzylidene)-2-(2-methylphenyl)-5(4H)-oxazolone

4-(4-methoxybenzylidene)-2-(2-methylphenyl)-5(4H)-oxazolone

Refernces

• 1、 Chen, Jianzhong,Gridnev, Ilya D.,Hu, Yawen,Li, Bowen,Zhang, Wanbin,Zhang, Zhenfeng. "Nickel-Catalyzed Asymmetric Hydrogenation of 2-Amidoacrylates". supporting information. p. 5371 - 5375. Retrieved 2020/02/15.
• 2、 Han, Wen-Yong,Zuo, Jian,Wu, Zhi-Jun,Zhang, Xiao-Mei,Yuan, Wei-Cheng. "Lewis acid catalyzed formation of 3-amino-3-carboxy-tetrahydroquinoline derivatives via tandem 1,5-hydride transfer/cyclization process". . p. 7019 - 7025. Retrieved 2013/07/26.