N-(Carboxymethyl)anthranilic acid

Base Information

• Chemical Name: N-(Carboxymethyl)anthranilic acid
• CAS No.: 612-42-0
• Molecular Formula: C9H9NO4
• Molecular Weight: 195.175
• Hs Code.: 29224985
• European Community (EC) Number: 210-311-5
• NSC Number: 80600
• DSSTox Substance ID: DTXSID9060609
• Nikkaji Number: J7.018A
• Wikidata: Q27454068
• Metabolomics Workbench ID: 134132
• ChEMBL ID: CHEMBL443231
• Mol file: 612-42-0.mol

Synonyms:N-(2-carboxyphenyl)glycine

Chemical Property of N-(Carboxymethyl)anthranilic acid

Chemical Property:

• Appearance/Colour: light yellow to yellow Crystalline powder
• Vapor Pressure: 3.31E-10mmHg at 25°C
• Melting Point: 218 °C (dec.)(lit.)
• Refractive Index: 1.66
• Boiling Point: 484.7 °C at 760 mmHg
• PKA: 3?+-.0.36(Predicted)
• Flash Point: 246.9 °C
• PSA: 86.63000
• Density: 1.472 g/cm³
• LogP: 0.95430
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 195.05315777
• Heavy Atom Count: 14
• Complexity: 229

Purity/Quality:

98%min ^*data from raw suppliers

N-(2-Carboxyphenyl)glycine ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C(=O)O)NCC(=O)O

Technology Process of N-(Carboxymethyl)anthranilic acid

There total 42 articles about N-(Carboxymethyl)anthranilic 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: 94.0%

glycine (56-40-6,18875-39-3,25718-94-9) + ortho-chlorobenzoic acid (118-91-2) → phenylglycine-o-carboxylic acid (612-42-0)

Guidance literature:

With copper; potassium carbonate; In N,N-dimethyl-formamide; at 25 ℃; for 0.416667h; ultrasonic irradiation;

DOI:10.1002/ejoc.200700281

Reference yield: 90.0%

sodium monochloroacetic acid (3926-62-3) + sodium o-aminobenzoate (552-37-4) → phenylglycine-o-carboxylic acid (612-42-0)

Guidance literature:

With Na⁽¹⁺⁾*H₂O = Na(H₂O)⁽¹⁺⁾; sodium carbonate; In water; for 0.233333h; Reflux; Microwave irradiation;

DOI:10.1002/hlca.200890212

Reference yield: 80.0%

anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) + chloroacetic acid (79-11-8) → phenylglycine-o-carboxylic acid (612-42-0)

Guidance literature:

With sodium carbonate; sodium hydroxide; In 1,4-dioxane; water; Heating;

DOI:10.1016/j.bioorg.2019.103062

upstream raw materials:

2-(N-(carboxymethyl)acetamido)benzoic acid

2-(carbamoylmethylamino)benzoic acid

2-(oxalamino)benzoic acid

2-(carboxyphenyl)iminodiacetic acid

Downstream raw materials:

N-(2-nitrophenyl)anthranilic acid

2-[[2-oxo-2-(phenylamino)ethyl]amino]benzoic acid

N-propionylphenylglycine-o-carboxylic acid

N-(ethoxycarbonylmethyl)anthranilic acid

Refernces

• 1、 Fei, Xing-Hai,Guan, Xiang,He, Bin,Li, Zong-Qin,Wang, Da-Peng,Yang, Fen-Fen,Yang, Yuan-Yong,Zhao, Yong-Long,Zhou, Meng. "Construction of Oxepino[3,2-b]indoles via [4+3] Annulation of 2-Ylideneoxindoles with Crotonate-Derived Sulfur Ylides". supporting information. p. 3018 - 3024. Retrieved 2021/06/26.
• 2、 Bakulina, Olga,Chizhova, Maria,Dar'in, Dmitry,Krasavin, Mikhail. "A General Way to Construct Arene-Fused Seven-Membered Nitrogen Heterocycles". supporting information. p. 362 - 371. Retrieved 2018/01/27.