2-Amino-4-chlorophenol

Base Information

• Chemical Name: 2-Amino-4-chlorophenol
• CAS No.: 95-85-2
• Molecular Formula: C6H6ClNO
• Molecular Weight: 143.573
• Hs Code.: 29222900
• European Community (EC) Number: 202-458-9
• ICSC Number: 1652
• NSC Number: 247814
• UN Number: 2673
• UNII: 2Z43LEA3DX
• DSSTox Substance ID: DTXSID5024473
• Nikkaji Number: J31.070K
• Wikidata: Q27255828
• ChEMBL ID: CHEMBL251389
• Mol file: 95-85-2.mol

Synonyms:2-amino-4-chlorophenol;2-amino-4-chlorophenol hydrochloride;2-amino-4-chlorophenol, sulfate(1:1);4-chloro-2-aminophenol;5-chloro-2-hydroxyaniline

Chemical Property of 2-Amino-4-chlorophenol

Chemical Property:

• Appearance/Colour: brown crystalline solid
• Melting Point: 136-141 °C(lit.)
• Refractive Index: 1.5618 (estimate)
• Boiling Point: 276.8 °C at 760 mmHg
• PKA: 9.31±0.18(Predicted)
• Flash Point: 121.2 °C
• PSA: 46.25000
• Density: 1.406 g/cm³
• LogP: 2.20900
• Storage Temp.: Store below +30°C.
• Solubility.: 2.3g/l
• Water Solubility.: Insoluble.
• 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
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

2-Amino-4-chlorophenol ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amino Phenols
• Canonical SMILES: C1=CC(=C(C=C1Cl)N)O
• Inhalation Risk: A nuisance-causing concentration of airborne particles can be reached quickly when dispersed, especially if powdered.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization.
• Uses: Intermediate. 2-Amino-4-chlorophenol is a widely used reagent in the synthesis of various drugs, dyes and pesticides. A reagent in the synthesis of aggrecanase-2 inhibitors based on acylthiosemicarbazide zinc-binding, used in the treatment of osteoarthritis.

Technology Process of 2-Amino-4-chlorophenol

There total 24 articles about 2-Amino-4-chlorophenol 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: 99.0%

p-chloro-o-nitrophenol (89-64-5) → 2-hydroxy-5-chloro-aniline (95-85-2)

Guidance literature:

With hydrazine hydrate; In water; at 110 ℃; Sealed tube; Green chemistry;

DOI:10.1039/c7gc00986k

Reference yield: 93.0%

2-amino-phenol (95-55-6) → 2-hydroxy-5-chloro-aniline (95-85-2)

Guidance literature:

With N-chloro-succinimide; 2C₅HN₁₀^(3-)*2Mn⁽²⁺⁾*Cu⁽²⁺⁾*5H₂O; In acetonitrile; at 90 ℃; for 6h; Reagent/catalyst; regioselective reaction;

DOI:10.1021/acs.inorgchem.9b01891

Reference yield: 83.0%

sodium; 4-(5-chloro-2-hydroxy-phenylazo)-benzenesulfonate → 2-hydroxy-5-chloro-aniline (95-85-2)

Guidance literature:

With sodium hydroxide; sodium dithionite; In water; for 0.00694444h; microwave irradiation;

upstream raw materials:

p-chloro-o-nitrophenol

sulfuric acid mono-(2-amino-4-chloro-phenyl ester)

2-hydroxy-5-chloroazobenzene

O-(4-chlorophenyl)hydroxylamine

Downstream raw materials:

3-[1-(5-chloro-2-hydroxy-phenylimino)-ethyl]-dihydro-furan-2-one

N-(5-chloro-2-hydroxyphenyl)acetamide

N-benzylidene-2-hydroxy-5-chloroaniline

N-(5-chloro-2-hydroxyphenyl)benzamide

Refernces

• 1、 Ellaithy,El-Ragehy,El-Ghobashy. "Kinetic study of alkaline induced hydrolysis of the skeletal muscle relaxant chlorzoxazone using ratio spectra first derivative spectrophotometry". . p. 337 - 342. Retrieved 2003.
• 2、 Taheri-Ledari, Reza,Mirmohammadi, Seyedeh Shadi,Valadi, Kobra,Maleki, Ali,Shalan, Ahmed Esmail. "Convenient conversion of hazardous nitrobenzene derivatives to aniline analogues by Ag nanoparticles, stabilized on a naturally magnetic pumice/chitosan substrate". . p. 43670 - 43681. Retrieved 2020/12/25.
• 3、 Alarcón-Espósito, Jazmín,Araya-Maturana, Ramiro,Cabezas, David,Cerda-Cavieres, Christopher,Chung, Hery,Iturriaga-Vásquez, Patricio,Mella-Raipán, Jaime,Ojeda-Gómez, Claudia,Pessoa-Mahana, Carlos D.,Pessoa-Mahana, Hernán,Quiroz, Gabriel,Reyes-Parada, Miguel,Rodríguez-Lavado, Julio,Saitz, Claudio. "Synthesis, docking, 3-D-qsar, and biological assays of novel indole derivatives targeting serotonin transporter, dopamine D2 receptor, and mao-a enzyme: In the pursuit for potential multitarget directed ligands". . . Retrieved 2020/10/18.