2-Chloro-5-aminophenol

Base Information

• Chemical Name: 2-Chloro-5-aminophenol
• CAS No.: 6358-06-1
• Molecular Formula: C6H6ClNO
• Molecular Weight: 143.573
• Hs Code.: 29089990
• European Community (EC) Number: 677-109-0
• DSSTox Substance ID: DTXSID1073369
• Nikkaji Number: J81.199H
• Wikidata: Q72517034
• Mol file: 6358-06-1.mol

Synonyms:2-Chloro-5-aminophenol;5-Amino-2-chlorophenol;6358-06-1;4-CHLORO-3-HYDROXYANILINE;Phenol, 5-amino-2-chloro-;3-Amino-6-chlorophenol;BRN 2081092;5-amino-2-chloro-phenol;3-hydroxy-4-chloroaniline;4-chloro-3-hydroxy aniline;SCHEMBL1014786;DTXSID1073369;JSCNCRWPXOTDDZ-UHFFFAOYSA-;AMY13788;MFCD01707858;AKOS013153303;AC-1558;CS-W013317;PS-3508;AC-18195;LS-103881;FT-0650688;EN300-84106;4-13-00-01000 (Beilstein Handbook Reference);A834421;Q-100011;5-CHLORO-4-NITRO-1-BENZOFURAN-2-CARBOXYLICACID;740789-42-8

Chemical Property of 2-Chloro-5-aminophenol

Chemical Property:

• Appearance/Colour: Off-white powder
• Vapor Pressure: 0.00247mmHg at 25°C
• Melting Point: 160 °C
• Refractive Index: 1.65
• Boiling Point: 278.8 °C at 760 mmHg
• PKA: 8.55±0.10(Predicted)
• Flash Point: 122.4 °C
• PSA: 46.25000
• Density: 1.406 g/cm³
• LogP: 2.20900
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Sensitive.: Light Sensitive
• Solubility.: DMSO, Methanol
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 143.0137915
• Heavy Atom Count: 9
• Complexity: 99.1

Purity/Quality:

99% ^*data from raw suppliers

5-Amino-2-chlorophenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1N)O)Cl
• Uses: 5-Amino-2-chlorophenol is used in the synthesis of antimalarial quinolones. Also used in the synthesis of potent anti-HIV agents based upon pyrimidinylphenylamine 1.

Technology Process of 2-Chloro-5-aminophenol

There total 5 articles about 2-Chloro-5-aminophenol 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%

5-nitro-2-chlorophenol (619-10-3) → 5-amino-2-chlorophenol (6358-06-1)

Guidance literature:

Pt/C; In ethyl acetate;

Reference yield:

4-chloro-m-anisidine (13726-14-2) → 5-amino-2-chlorophenol (6358-06-1)

Guidance literature:

With hydrogen bromide; acetic acid; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate;

Reference yield:

2-methoxy-4-nitrophenylamine (97-52-9) → 5-amino-2-chlorophenol (6358-06-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 67 percent / tert-butylnitrite; CuCl₂ / acetonitrile / 2 h / 0 °C

2: 56 percent / HBr / H₂O / 24 h / Heating

3: 90 percent / H₂ / PtO₂ / ethanol

With tert.-butylnitrite; hydrogen bromide; hydrogen; copper dichloride; platinum(IV) oxide; In ethanol; water; acetonitrile;

DOI:10.1002/etc.5620200701

upstream raw materials:

5-nitro-2-chlorophenol

5-Nitro-2-aminophenol

2-methoxy-4-nitrophenylamine

4-chloro-m-anisidine

Downstream raw materials:

C₁₆H₁₈ClN₃O₃

tert-butyl (4-chloro-3-hydroxyphenyl)carbamate

N-(3-hydroxy-4-chlorophenyl)-3,4,5,6-tetrahydrophthalimide

2-chloro-5-acetylamino phenol