2-Amino-4-chlorobenzoic acid

Base Information

• Chemical Name: 2-Amino-4-chlorobenzoic acid
• CAS No.: 89-77-0
• Molecular Formula: C7H6ClNO2
• Molecular Weight: 171.583
• Hs Code.: 2922.49
• European Community (EC) Number: 201-938-5
• NSC Number: 17188
• UNII: G55K85R12H
• DSSTox Substance ID: DTXSID80237473
• Nikkaji Number: J4.307I
• Wikidata: Q27278774
• Mol file: 89-77-0.mol

Synonyms:2-amino-4-chlorobenzoic acid;4CABA cpd

Chemical Property of 2-Amino-4-chlorobenzoic acid

Chemical Property:

• Appearance/Colour: off-white powder
• Vapor Pressure: 1.55E-05mmHg at 25°C
• Melting Point: 231-233 °C(lit.)
• Refractive Index: 1.5560 (estimate)
• Boiling Point: 351.2 °C at 760 mmHg
• PKA: 4.71±0.10(Predicted)
• Flash Point: 166.2 °C
• PSA: 63.32000
• Density: 1.476 g/cm³
• LogP: 2.20160
• Storage Temp.: Store below +30°C.
• Solubility.: almost transparency in 1mol/L NaOH
• Water Solubility.: slightly soluble
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 171.0087061
• Heavy Atom Count: 11
• Complexity: 163

Purity/Quality:

99% ^*data from raw suppliers

2-Amino-4-chlorobenzoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1Cl)N)C(=O)O
• Uses: 2-Amino-4-chlorobenzoic Acid is used in the preparation of quinazolinone derivatives observed to be useful in the treatment of Alzheimer’s disease. Also it aids in the synthesis of non-nucleoside, thumb pocket 2 HCV NS5B polymerase inhibitors used in Hepatitis C therapy.

Technology Process of 2-Amino-4-chlorobenzoic acid

There total 23 articles about 2-Amino-4-chlorobenzoic 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: 88.0%

2,4 dichlorobenzoic acid (50-84-0) → 2-Amino-4-chlorobenzoic acid (89-77-0)

Guidance literature:

With ammonium hydroxide; at 126 - 129 ℃; for 6h; under 3800 - 9120 Torr;

DOI:10.1007/BF00764884

Reference yield: 74.0%

4-chloro-2-nitrotoluene (89-59-8) → 2-Amino-4-chlorobenzoic acid (89-77-0)

Guidance literature:

With selenium; nitrobenzene; sodium hydroxide; In methanol; water; dimethyl sulfoxide; at 90 ℃; for 5h; Inert atmosphere;

DOI:10.1039/d0gc04407e

Reference yield: 68.0%

2,4-dichlorobenzoic acid potassium salt (66909-52-2) → 2-Amino-4-chlorobenzoic acid (89-77-0)

Guidance literature:

With ammonium hydroxide; copper diacetate; at 126 - 129 ℃; for 10h;

DOI:10.1007/BF00764884

upstream raw materials:

6-chloroisatin

2,4 dichlorobenzoic acid

4-chloro-2-nitro-benzoic acid

2-amino-4-chlorobenzamide

Downstream raw materials:

4-chloro-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)benzoic acid

7-chloro-2-phenyl-4H-benzo[d][1,3]oxazin-4-one

2-benzamido-4-chlorobenzoic acid

7-chloro-3,4-dihydroquinazolin-4-one

Refernces

• 1、 Jiang, Xuefeng,Li, Yiming,Lin, Zhenyang,Wang, Yuhong,Yang, Tilong. "Selenium-catalyzed intramolecular atom- And redox-economical transformation ofo-nitrotoluenes into anthranilic acids". supporting information. p. 2986 - 2991. Retrieved 2021/05/05.
• 2、 Han, Sheng,Sang, Yali,Wu, Yan,Tao, Yuan,Pannecouque, Christophe,De Clercq, Erik,Zhuang, Chunlin,Chen, Fen-Er. "Molecular Hybridization-Inspired Optimization of Diarylbenzopyrimidines as HIV-1 Nonnucleoside Reverse Transcriptase Inhibitors with Improved Activity against K103N and E138K Mutants and Pharmacokinetic Profiles". . . Retrieved 2019/11/11.