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

Chlorzoxazone Related Compound A ^*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

(5-chloro-2-hydroxy-phenyl)-carbamic acid ethyl ester

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

4-chloro-2-(4-nitro-benzylidenamino)-phenol

Refernces

Synthesis, characterization and antimicrobial activity of some transition metal complexes of N-(5-chloro-2-hydroxyphenyl)-3-methoxy-salicylaldimine

10.4314/bcse.v29i1.6

The study focuses on the synthesis, characterization, and antimicrobial activity of transition metal complexes derived from N-(5-chloro-2-hydroxyphenyl)-3-methoxy-salicylaldimine (H2L), an ONO type tridentate ligand. The complexes of Cr(III), Fe(II), Fe(III), Co(II), Ni(II), Cu(II), and Zn(II) were prepared and characterized using various analytical techniques including elemental analysis, magnetic moment measurements, molar conductivity, thermogravimetric analysis (TGA), nuclear magnetic resonance (NMR), infrared (IR), ultraviolet-visible (UV-vis), and electrospray ionization-mass spectrometry (ESI-MS). The research revealed that all complexes, except for [Zn(L)(H2O)2], are paramagnetic and mostly adopt octahedral geometries, with the exception of Zn(II) and Fe(III) which exhibit five coordination geometries and Cu(II) which has a four-coordinated dimeric structure with acetato bridging. The antimicrobial activities of these complexes were tested against six bacterial strains and Candida albicans as a fungal strain, with Ni(II) and Co(II) complexes showing significant selective activity against S. epidermidis and C. albicans, and the Cr(III) complex displaying antibacterial activity against S. epidermidis, while the Zn(II) complex showed antifungal activity against C. albicans. The ligand itself did not exhibit any antimicrobial activity.