4-Amino-2-chlorobenzoic acid

Base Information

• Chemical Name: 4-Amino-2-chlorobenzoic acid
• CAS No.: 2457-76-3
• Molecular Formula: C7H6ClNO2
• Molecular Weight: 171.583
• Hs Code.: 29224995
• European Community (EC) Number: 219-540-5
• NSC Number: 64328,53160,33944
• UNII: Y3S6924IA6
• DSSTox Substance ID: DTXSID9062431
• Nikkaji Number: J1.811B
• Wikidata: Q27126727
• Metabolomics Workbench ID: 60634
• ChEMBL ID: CHEMBL3278354
• Mol file: 2457-76-3.mol

Synonyms:2-chloro-4-aminobenzoic acid;2-chloro-GABA;4-amino-2-chlorobenzoic acid

Chemical Property of 4-Amino-2-chlorobenzoic acid

Chemical Property:

• Appearance/Colour: beige to light brown powder
• Vapor Pressure: 5.58E-06mmHg at 25°C
• Melting Point: 211 °C (dec.)(lit.)
• Refractive Index: 1.5560 (estimate)
• Boiling Point: 365.3 °C at 760 mmHg
• PKA: 3.81±0.25(Predicted)
• Flash Point: 174.8 °C
• PSA: 63.32000
• Density: 1.476 g/cm³
• LogP: 2.20160
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.5
• 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:

99.9% ^*data from raw suppliers

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

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1N)Cl)C(=O)O
• Uses: 4-Amino-2-chlorobenzoic acid is the principal metabolite of 2-Chloroprocaine, a compound that is widely used for epidural analgesia in obstetrics.

Technology Process of 4-Amino-2-chlorobenzoic acid

There total 11 articles about 4-Amino-2-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: 98.0%

2-chloro-4-nitrobenzoic acid (99-60-5) → 4-amino-2-chlorobenzoic acid (2457-76-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; under 760 Torr;

DOI:10.1021/jm040144e

Reference yield: 93.6%

4-[bis((trimethylsilyl)ethoxymethyl)amino]-2-chlorobenzaldehyde → 4-amino-2-chlorobenzoic acid (2457-76-3)

Guidance literature:

With Wilkinson's catalyst; hydrogen; dihydrogen peroxide; at 20 - 70 ℃; for 13h; under 3800.26 - 7600.51 Torr; Temperature;

Reference yield:

2-chloro-4-nitrotoluene (121-86-8) → 4-amino-2-chlorobenzoic acid (2457-76-3)

Guidance literature:

Multi-step reaction with 2 steps

1: aqueous nitric acid / 120 - 180 °C

2: tin (II)-chloride; aqueous hydrochloric acid

With hydrogenchloride; nitric acid; tin(ll) chloride;

DOI:10.1007/BF02809649

upstream raw materials:

2-chloro-4-nitrobenzoic acid

4-Acetylamino-2-chlorobenzoic acid

ethyl acetate

2-chloro-4-nitrotoluene

Downstream raw materials:

chloroprocaine hydrochloride

4-(N'-allyl-thioureido)-2-chloro-benzoic acid

ortho-chlorobenzoic acid

4-(tert-butoxycarbonylamino)-2-chlorobenzoic acid

Refernces

• 1、 Karami, Kazem,Rahimi, Mahzad,Dinari, Mohammad. "High catalytic activity of a new Ag phosphorus ylide complex supported on montmorillonite: synthesis, characterization, and application for room temperature nitro reduction". . p. 281 - 291. Retrieved 2018/03/29.
• 2、 -. "HEDGEHOG ANTAGONISTS HAVING ZINC BINDING MOIETIES". Paragraph 0162; 0187. . Retrieved 2014/02/16.