Cas no 53994-69-7 (7-Amino-3-chloro-3-cephem-4-carboxylic acid)

7-Amino-3-chloro-3-cephem-4-carboxylic acid is a key intermediate in the synthesis of cephalosporin antibiotics, a class of β-lactam compounds widely used for their broad-spectrum antibacterial activity. Its structural features, including the 3-chloro substitution and 4-carboxylic acid group, enhance reactivity for further chemical modifications, enabling the production of semi-synthetic cephalosporins with improved stability and efficacy. This compound is particularly valuable in pharmaceutical manufacturing due to its role in developing antibiotics with resistance to β-lactamases. High purity and consistent quality are critical to ensure optimal yields in downstream synthesis. Proper handling and storage are recommended to maintain stability.
7-Amino-3-chloro-3-cephem-4-carboxylic acid structure
53994-69-7 structure
Product Name:7-Amino-3-chloro-3-cephem-4-carboxylic acid
CAS No:53994-69-7
MF:C7H7ClN2O3S
MW:234.660079240799
MDL:MFCD09039101
CID:56506
PubChem ID:6998927
Update Time:2025-10-30

7-Amino-3-chloro-3-cephem-4-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • (6R,7R)-7-Amino-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
    • 7-Amino-3-chloro cephalosporanic acid
    • 7-Amino-3-Chloro-3-Cephem-4-Carboxylic Acid
    • 7-ACCA
    • 7-Amino-3-Chloro Cephalosporanic Acid(7-ACCA )
    • (6R-trans)-7-amino-3-chloro-8-oxo-5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
    • 3-Chloro-7-amino-3-cephem-4-carboxylic Acid
    • 7-AC
    • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 7-amino-3-chloro-8-oxo-, (6R-trans)-
    • 7b-Amino-3-chloro-3-cephem-4-carboxylicacid
    • 7-Amino-3-chlorocephalosporanicacid
    • B9T49E55O2
    • (6R-trans)-7-Amino-3-chloro-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
    • 7-Amino-3-chlorocephalosporanic Acid
    • PubChem20435
    • OQSAF
    • 5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-AMINO-3-CHLORO-8-OXO-, (6R,7R)-
    • 7.BETA.-AMINO-3-CHLORO-3-CEPHEM-4-CARBOXYLIC ACID
    • (6R-TRANS)-7-AMINO-3-CHLORO-8-OXO-5-THIA-1- AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID
    • BCP10736
    • (6R,7R)-7-Ammonio-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
    • DTXSID501128595
    • 5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-AMINO-3-CHLORO-8-OXO-, (6R-TRANS)-
    • CS-0128939
    • EINECS 258-907-4
    • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-amino-3-chloro-8-oxo-, (6R,7R)-
    • Q27274555
    • EC 258-907-4
    • SCHEMBL6238516
    • UNII-B9T49E55O2
    • CEFACLOR IMPURITY B [EP IMPURITY]
    • AKOS016010169
    • OQSAFIZCBAZPMY-AWFVSMACSA-N
    • HY-131124
    • MFCD09039101
    • 7beta-amino-3-chloro-3-cephem-4-carboxylic acid
    • (6R,7R)-7-Amino-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid
    • AS-11699
    • D70579
    • WLZ3836
    • 53994-69-7
    • (6R,7R)-7-Amino-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; 3-Chloro-7-amino-3-cephem-4-carboxylic Acid; (6R-trans)-7-amino-3-chloro-8-oxo-5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;7-Amino-3-chlorocephalosporanic Acid; Cefaclor EP Impurity E; Cefaclor EP Impurity B
    • 7-Amino-3-chloro-3-cephem-4-carboxylic acid
    • MDL: MFCD09039101
    • Inchi: 1S/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-/m1/s1
    • InChI Key: OQSAFIZCBAZPMY-AWFVSMACSA-N
    • SMILES: ClC1CS[C@@H]2[C@@H](C(N2C=1C(=O)O)=O)N

Computed Properties

  • Exact Mass: 233.98700
  • Monoisotopic Mass: 233.987
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 1
  • Complexity: 357
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -2.8
  • Topological Polar Surface Area: 109

Experimental Properties

  • Density: 1.81
  • Melting Point: 230°C (dec.)
  • Boiling Point: 498.9°C at 760 mmHg
  • Flash Point: 255.5°C
  • Refractive Index: 1.735
  • PSA: 108.93000
  • LogP: 0.40200

7-Amino-3-chloro-3-cephem-4-carboxylic acid Security Information

7-Amino-3-chloro-3-cephem-4-carboxylic acid Customs Data

  • HS CODE:2934996000
  • Customs Data:

    China Customs Code:

    2934996000

    Overview:

    2934996000. 7-Phenylacetamide-3-Chloromethyl-4-Cephalosporanic acid p-methoxybenzyl ester\7-Aminocephalosporanic acid\7-Aminodeacetoxycephalosporanic acid. VAT:17.0%. Tax refund rate:9.0%. Regulatory conditions:nothing. Minimum tariff:6.0%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2934996000. VAT:17.0%. Tax rebate rate:9.0%. . MFN tariff:6.0%. General tariff:20.0%

7-Amino-3-chloro-3-cephem-4-carboxylic acid Pricemore >>

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Additional information on 7-Amino-3-chloro-3-cephem-4-carboxylic acid

Recent Advances in the Synthesis and Applications of 7-Amino-3-chloro-3-cephem-4-carboxylic acid (CAS: 53994-69-7)

7-Amino-3-chloro-3-cephem-4-carboxylic acid (CAS: 53994-69-7) is a key intermediate in the synthesis of cephalosporin antibiotics, a class of β-lactam antibiotics widely used to treat bacterial infections. Recent studies have focused on optimizing its synthesis, exploring its biological activity, and developing novel derivatives with enhanced therapeutic properties. This research briefing provides an overview of the latest advancements related to this compound, highlighting its significance in the pharmaceutical industry.

A recent study published in the Journal of Medicinal Chemistry (2023) demonstrated an improved synthetic route for 7-Amino-3-chloro-3-cephem-4-carboxylic acid, achieving higher yields and purity compared to traditional methods. The researchers utilized a combination of enzymatic catalysis and green chemistry principles, reducing the environmental impact of the synthesis process. This advancement is particularly relevant given the growing demand for sustainable pharmaceutical manufacturing practices.

In terms of biological applications, a 2024 study in Antimicrobial Agents and Chemotherapy investigated the compound's potential as a scaffold for developing new antibiotics against multidrug-resistant Gram-negative bacteria. The research team synthesized several derivatives of 7-Amino-3-chloro-3-cephem-4-carboxylic acid and evaluated their antibacterial activity, identifying two promising candidates with potent activity against carbapenem-resistant Enterobacteriaceae (CRE).

Structural analysis of 7-Amino-3-chloro-3-cephem-4-carboxylic acid and its derivatives has also been a focus of recent research. X-ray crystallography studies published in Acta Crystallographica Section D (2023) provided detailed insights into the molecular interactions between these compounds and bacterial penicillin-binding proteins (PBPs), offering valuable information for structure-based drug design.

The pharmaceutical industry has shown increasing interest in this compound, with several patent applications filed in 2023-2024 for novel synthetic methods and therapeutic applications. One notable development is its potential use in combination therapies, where it serves as a precursor for cephalosporins designed to work synergistically with β-lactamase inhibitors.

Quality control and analytical methods for 7-Amino-3-chloro-3-cephem-4-carboxylic acid have also seen advancements. A 2024 publication in the Journal of Pharmaceutical and Biomedical Analysis presented a validated HPLC method for the simultaneous determination of this compound and its potential impurities, addressing the need for robust quality assurance in API manufacturing.

Looking forward, researchers are exploring the potential of 7-Amino-3-chloro-3-cephem-4-carboxylic acid beyond traditional antibiotic applications. Preliminary studies suggest its derivatives may have applications in anticancer therapies and as modulators of the gut microbiome, though these areas require further investigation.

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