53994-69-7

Basic information

• Product Name: 7-Amino-3-chloro cephalosporanic acid
• Synonyms: 7-amino-3-chloro-8-oxo-,(6R,7R)-5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid;7-AMINO-3-CHLORO-3-CEPHEM-4-CARBOXYLIC ACID;7-AMINO-3-CHLORO-8-OXO-5-THIA-1-AZA-BICYCLO-[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID;7-AMINO-3-CHLORO CEPHALOSPORANIC ACID;ANCA;(6R-trans)-7-amino-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;7-amino-3-coloro-3-cephem-4-carboxylic acid;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-amino-3-chloro-8-oxo-,(6R,7R)-
• CAS NO: 53994-69-7
• Molecular Formula: C7H7ClN2O3S
• Molecular Weight: 234.66
• EINECS: 258-907-4
• Product Categories: Organic acids;Amines;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 53994-69-7.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 498.9oC at 760mmHg
• Flash Point: 255.5oC
• Appearance: /
• Density: 1.81g/cm3
• Vapor Pressure: 2.61E-11mmHg at 25°C
• Refractive Index: 1.735
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Aqueous Acid (Slightly, Heated), DMSO (Slightly, Heated, Sonicated)
• PKA: 1.87±0.50(Predicted)
• CAS DataBase Reference: 7-Amino-3-chloro cephalosporanic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Amino-3-chloro cephalosporanic acid(53994-69-7)
• EPA Substance Registry System: 7-Amino-3-chloro cephalosporanic acid(53994-69-7)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 53994-69-7(Hazardous Substances Data)

Usage

Description

7-Amino-3-chloro cephalosporanic acid, also known as 7-ACA, is a key intermediate compound in the synthesis of semi-synthetic cephalosporin antibiotics. It is a pale yellow solid with significant importance in the pharmaceutical industry due to its role in the production of various antibiotics.

Uses

Used in Pharmaceutical Industry:
7-Amino-3-chloro cephalosporanic acid is used as an intermediate for the preparation of semi-synthetic cephalosporin antibiotics. It serves as a crucial building block in the development of these life-saving medications, which are widely used to treat a range of bacterial infections. 7-Amino-3-chloro cephalosporanic acid's chemical properties make it an ideal candidate for the synthesis of various cephalosporin derivatives, enhancing their effectiveness and broadening their application in combating bacterial diseases.

InChI:InChI=1/C7H7ClN2O3S/c8-2-1-14-6-3(9)5(11)10(6)4(2)7(12)13/h3,6H,1,9H2,(H,12,13)/t3-,6-/m0/s1

Downstream Products

• 115339-15-6 7-<(4-hydroxyphenyl)acetamido>-3-chloro-3-cephem-4-carboxylic acid 
• 80730-79-6 C₁₉H₁₆ClN₃O₃S 
• 115384-96-8 7-[(4-hydroxyphenoxy)acetamido]-3-chloro-3-cephem-4-carboxylic acid 
• 53994-70-0 (6R,7R)-7-Amino-3-chloro-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 1027958-86-6 (6R,7R)-7-{2-{(Z)-3-[4-Benzhydryloxy-5-(4-methoxy-benzyloxy)-1-oxy-pyridin-2-yl]-isoxazol-5-ylmethoxyimino}-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-3-chloro-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 331780-41-7 (6R,7R)-7-[2-(5-amino-[1,2,4]thiadiazol-3-yl)-2-(Z)-trityloxyimino-acetylamino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester 
• 331780-46-2 (7R,6R)-7-[2-(5-amino-[1,2,4]thiadiazol-3-yl)-2-(Z)-trityloxyimino-acetylamino]-3-[2-(2-tert-butoxycarbonylamino-ethylsulfanylmethyl)-pyridin-3-ylsulfanyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tertbutyl ester 
• 171017-56-4 (6R,7R)-3-chloro-7-<2-(2-hydroxyphenyl)-4-thiazolyl>acetylamino-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenylmethyl ester 
• 171017-64-4 (6R,7R)-3-chloro-7-<2-(3-hydroxy-2-pyridyl)-4-thiazolyl>acetylamino-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenylmethyl ester 
• 171017-60-0 (6R,7R)-3-chloro-7-<2-(2,6-dihydroxyphenyl)-4-thiazolyl>acetylamino-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenylmethyl ester 
• 115385-03-0 7-<<2-<(triphenylmethyl)amino>thiazol-4-yl>acetamido>-3-chloro-3-cephem-4-carboxylic acid 
• 144460-65-1 C₂₁H₁₇⁽²⁾H₃N₂O₃S 
• 144460-61-7 (2R,6R,7R)-1-aza-3-<((2)H3)-methyl>-7-amino-(N-t-butyloxycarbonyl)-8-oxo-5-thiabicyclo<4.2.0>oct-3-ene-2-carboxylic acid benzhydryl ester 
• 144460-63-9 (6R,7R)-1-aza-3-<((2)H3)-methyl>-7-amino-(N-t-butyloxycarbonyl)-8-oxo-5-thiabicyclo<4.2.0>oct-2-ene-2-carboxylic acid benzhydryl ester 

Relevant articles and documents

On the substrate preference of glutaryl acylases

The substrate preferences of three acylases - two wild-type enzymes and an evolved variant obtained by directed evolution - which are prototypical enzymes for glutaryl-7-ACA acylase and cephalosporin C acylase subfamilies, have been investigated. A preliminary screening of enzymes' performances on a large set of substrates has been carried out by a colorimetric assay performed in 96-well plates and by a pH-Stat monitoring the hydrolytic activities. Subsequently, kinetic data for selected substrates have been determined, thus elucidating the substrate preference of members of glutaryl-7-ACA acylase vs. cephalosporin C acylase subfamilies. These achievements pave the way to the ability of choosing the best enzyme for the hydrolysis of different compounds of industrial importance.