3964-54-3

Basic information

• Product Name: 3-CHLORO-4-HYDROXYACETANILIDE
• Synonyms: 3-CHLORO-4-HYDROXYACETANILIDE;N-(3-chloro-4-hydroxyphenyl)acetamide;2-Chloro-4-acetamidophenol;3''-CHLORO-4''-HYDROXYACETANILIDE 97%;N-(3-chloro-4-hydroxy-phenyl)ethanamide;4-AcetylaMino-2-chlorophenol;2-Chloro-4-acetylaMinophenol;4-AcetaMido-2-chlorophenol
• CAS NO: 3964-54-3
• Molecular Formula: C₈H₈ClNO₂
• Molecular Weight: 185.61
• EINECS: 223-570-4
• Product Categories: Aromatics;Impurities;Intermediates & Fine Chemicals;Isotope Labelled Compounds;Pharmaceuticals
• Mol File: 3964-54-3.mol
• Article Data: 10

Chemical Properties

• Melting Point: 143-144°C
• Boiling Point: 379.9 °C at 760 mmHg
• Flash Point: 183.5 °C
• Appearance: /
• Density: 1.396 g/cm³
• Vapor Pressure: 2.6E-06mmHg at 25°C
• Refractive Index: 1.63
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 8.44±0.18(Predicted)
• CAS DataBase Reference: 3-CHLORO-4-HYDROXYACETANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-4-HYDROXYACETANILIDE(3964-54-3)
• EPA Substance Registry System: 3-CHLORO-4-HYDROXYACETANILIDE(3964-54-3)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 3964-54-3(Hazardous Substances Data)

Usage

Chemical Properties

Pale Purple Solid

Uses

Paracetamol (Acetaminophen -A161220) impurity.

InChI:InChI=1/C8H8ClNO2/c1-5(11)10-6-2-3-8(12)7(9)4-6/h2-4,12H,1H3,(H,10,11)

Upstream product

• 50700-49-7 N-acetyl-p-benzoquinoneimine 
• 99512-61-5 N-(pivaloyloxy)-4-methoxyacetanilide 
• 60-35-5 acetamide 
• 3964-52-1 2-chloro 4-aminophenol 
• 5345-54-0 3-chloro-4-methoxyaniline 
• 103-90-2 4-acetaminophenol 
• 75-36-5 acetyl chloride 
• 2457-76-3 4-amino-2-chlorobenzoic acid 
• 72-89-9 acetylcoenzyme A 
• 91631-56-0 N-sulfonoxy-p-bromoacetanilide pyridinium salt 
• 7073-42-9 N-(3-chloro-4-methoxyphenyl)acetamide 
• 91631-54-8 N-sulfonoxy-p-chloroacetanilide pyridinium salt 
• 102725-57-5 N-(pivaloyloxy)phenacetin 
• 64-19-7 acetic acid 

Downstream Products

• 1239465-30-5 N-[4-(2-adamantan-1-yl-2-oxoethoxy)-3-chlorophenyl]acetamide 
• 174668-87-2 3-chloro-4-tetrahydropyranyloxy-aniline 
• 220587-30-4 N-acetyl-3-chloro-4-tetrahydropyranyloxy-aniline 
• 60963-13-5 N-[3-Chloro-4-(2,6-dichloro-4-nitro-phenoxy)-phenyl]-acetamide 
• 110179-58-3 acetic acid-[3-chloro-4-(2-diethylamino-ethoxy)-anilide] 
• 60963-42-0 N-[4-(4-Amino-2,6-dichloro-phenoxy)-3-chloro-phenyl]-acetamide 

Relevant articles and documents

De novo biosynthesis and whole-cell catalytic production of paracetamol on a gram scale in Escherichia coli

The synthetic drug paracetamol is one of the most commonly used analgesic, antipyretic agents around the world. Global massive demand promoted its synthesis in large quantities. Chemical synthesis is the main approach for paracetamol production. However, the reaction process contributes toward environmental pollution, and the reaction conditions are harsh. Herein, we reported the construction of the paracetamol de novo biosynthetic pathway in Escherichia coli. Five enzymes from different microbial sources were heterologously expressed into E. coli to construct the APAP (1) producing strain PA1. Through protein engineering of ABH (4-aminobenzoate hydroxylase) and PANAT (arylamine N-acetyltransferase), enhancement of the host cell resistance to the substrate or final product, and utilizing synthetic protein scaffolds to optimize the metabolic flux, the engineered strain could produce 942.5 mg L-1 (6.24 mM) paracetamol in a fed-batch 5 L fermenter directly from glucose or glycerol, which circumvents the fossil fuel resource use. Moreover, we established a whole-cell cascade biocatalytic synthesis way to paracetamol and analogues. Using p-aminobenzoate as the substrate, 4.2 g L-1 (27.7 mM) paracetamol can be formed after 9 h (95% conversion rate). After metabolic engineering, enzyme molecular modification, and other optimizations, we created the biotransformation strategy to manufacture paracetamol on a gram scale. This study provides a promising green and efficient alternative to the traditional chemical manufacturing method.

Bisacetamide hydrochloride: A chemoselective and inexpensive N-acetylating reagent for aminophenols

A facile and chemoselective acetylation of aminophenols using bisacetamide hydrochloride under conventional heating and microwave irradiation has been developed. Also, a rapid method for the microwave-assisted preparation of aminophenols is described herein.

Novel thiopyrano[3,2-b] and cycloalkeno[1,2-b]indole derivatives with high inhibitory properties in LTB4 production

Series of thiopyrano[3,2-b] and cycloalkeno[1,2-b]indoles were synthesized and evaluated in order to determine the necessary structural requirements for high leukotrienes biosynthesis inhibition. In vitro experiments showed that compounds 11b and 12b belonging to the second series were the most active and selective compounds on LTB4 production. Further in vivo investigations have shown additional very significant activity in the acute phorbol ester induced mouse ear swelling which is predictive of potential antipsoriatic properties.