N-(Chloroacetyl) anthranilic acid

Base Information

• Chemical Name: N-(Chloroacetyl) anthranilic acid
• CAS No.: 14422-49-2
• Molecular Formula: C9H8 Cl N O3
• Molecular Weight: 213.62
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID60932272
• Wikidata: Q82907956
• Mol file: 14422-49-2.mol

Synonyms:2-[(2-chloroacetyl)amino]benzoate;Benzoic acid, 2-((chloroacetyl)amino)-;N-(Chloroacetyl) anthranilic acid;DTXSID60932272;2-(2-CHLOROACETAMIDO)BENZOATE;N-(2-Carboxyphenyl)-2-chloroethanimidate;D84592

Chemical Property of N-(Chloroacetyl) anthranilic acid

Chemical Property:

• Vapor Pressure: 5.53E-09mmHg at 25°C
• Melting Point: 196-197 °C
• Boiling Point: 452.7°Cat760mmHg
• PKA: 3.15±0.10(Predicted)
• Flash Point: 227.6°C
• PSA: 66.40000
• Density: 1.458g/cm³
• LogP: 1.63510
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 212.0114458
• Heavy Atom Count: 14
• Complexity: 227

Purity/Quality:

98%Min ^*data from raw suppliers

2-[(Chloroacetyl)amino]benzoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C(=O)[O-])NC(=O)CCl

Technology Process of N-(Chloroacetyl) anthranilic acid

There total 5 articles about N-(Chloroacetyl) 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: 97.0%

anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) + chloroacetyl chloride (79-04-9) → 2-chloroacetamidobenzoic acid (14422-49-2)

Guidance literature:

In benzene; for 2h; Heating;

DOI:10.1016/S0040-4020(01)80886-3

Reference yield:

anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) + chloroacetic acid ethyl ester (105-39-5) → 2-chloroacetamidobenzoic acid (14422-49-2)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 5 ℃; for 10h;

DOI:10.3390/PH14090870

Reference yield:

phthalimide (136918-14-4,85-41-6) → 2-chloroacetamidobenzoic acid (14422-49-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydroxide; bromine / water / 0.03 h / -5 °C / Reflux

1.2: pH 4 - 5

2.1: N,N-dimethyl-formamide / 0 - 20 °C

With bromine; sodium hydroxide; In water; N,N-dimethyl-formamide;

DOI:10.1039/c3cc45203d

upstream raw materials:

anthranilic acid

chloroacetyl chloride

phthalimide

chloroacetic acid ethyl ester

Downstream raw materials:

N^O-o-Carboxy-phenyl-N^S-cyclohexyl-thiooxamid

2-{2-[Acetyl-(4-methoxy-phenyl)-amino]-acetylamino}-benzoic acid

2-Chlormethyl-3,4-dihydro-3-(4-nitrophenyl)-4-chinazolinon

2-Chlormethyl-3,4-dihydro-3-(2-nitrophenyl)-4-chinazolinon

Refernces

• 1、 Alam, Mohammad Mahboob,Alfaifi, Mohammad Y.,Alfaifi, Sulaiman Y. M.,Almalki, Abdulraheem S. A.,Alsenani, Nawaf I.,Alsharif, Meshari A.,Elbehairi, Serag Eldin I.,Elhenawy, Ahmed A.,Malebari, Azizah M.,Nazreen, Syed. "Naproxen based 1,3,4-oxadiazole derivatives as EGFR inhibitors: Design, synthesis, anticancer, and computational studies". . . Retrieved 2021/10/05.
• 2、 Aarjane, Mohammed,Slassi, Siham,Tazi, Bouchra,Maouloua, Mohamed,Amine, Amina. "Novel series of acridone-1,2,3-triazole derivatives: microwave-assisted synthesis, DFT study and antibacterial activities". . . Retrieved 2019/09/06.