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7-Amino-3-(1,2,3-triazol-4-ylthio)methyl cephalosporanic acid is a chemical compound derived from cephalosporanic acid, a key component in the synthesis of cephalosporin antibiotics. 7-Amino-3-(1,2,3-triazol-4-ylthio)methyl cephalosporanic acid features a triazole ring attached to the cephalosporanic core, which enhances its antimicrobial properties and broadens its spectrum of activity.

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  • 37539-03-0 Structure
  • Basic information

    1. Product Name: 7-Amino-3-(1,2,3-triazol-4-ylthio)methyl cephalosporanic acid
    2. Synonyms: 7-TACA;7-AMINO-3-(1,2,3-TRIAZOL-4-YLTHIO)METHYL CEPHALOSPORANIC ACID;7-AMINO-3-(1,2,3-TRIAZOL-4-YLTHIO)METHYL CEPHALOSPORANIC ACID(7-TACA);7-Amino-3-((1,2,3-Triazol-5-YL)Thiomethyl)Cephalos;(7R)-7-AMINO-3-[(1H-1,2,3-TRIAZOL-4-YLSULFANYL)METHYL]-3,4-DIDEHYDROCEPHAM-4-CARBOXYLIC ACID;(6R-trans)-7-Amino-8-oxo-3-[(1H-1,2,3-triazol-4-ylthio)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;7-Amino-3-((1H-1,2,3-triazol-5-yl)-thiomethyl)-ceph-3-em-4-carboxylic acid;TACA
    3. CAS NO:37539-03-0
    4. Molecular Formula: C10H11N5O3S2
    5. Molecular Weight: 313.36
    6. EINECS: 253-547-4
    7. Product Categories: Organic acids
    8. Mol File: 37539-03-0.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 723.3 °C at 760 mmHg
    3. Flash Point: 391.2 °C
    4. Appearance: /
    5. Density: 1.8g/cm3
    6. Vapor Pressure: 5.85E-22mmHg at 25°C
    7. Refractive Index: 1.798
    8. Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
    9. Solubility: Methanol (Slightly, Heated, Sonicated), Water (Slightly)
    10. PKA: 2.56±0.50(Predicted)
    11. Stability: Light Sensitive, Temperature Sensitive, Unstable in Solution
    12. CAS DataBase Reference: 7-Amino-3-(1,2,3-triazol-4-ylthio)methyl cephalosporanic acid(CAS DataBase Reference)
    13. NIST Chemistry Reference: 7-Amino-3-(1,2,3-triazol-4-ylthio)methyl cephalosporanic acid(37539-03-0)
    14. EPA Substance Registry System: 7-Amino-3-(1,2,3-triazol-4-ylthio)methyl cephalosporanic acid(37539-03-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 37539-03-0(Hazardous Substances Data)

37539-03-0 Usage

Uses

Used in Pharmaceutical Industry:
7-Amino-3-(1,2,3-triazol-4-ylthio)methyl cephalosporanic acid is used as an intermediate in the synthesis of triazole-based semi-synthetic cephalosporins for the development of new antibiotics. These semi-synthetic cephalosporins exhibit improved potency, stability, and effectiveness against a wider range of bacterial infections, making them valuable in the treatment of various diseases caused by resistant bacteria.
Additionally, this compound may also be utilized in research and development for the creation of novel cephalosporin derivatives with enhanced properties, such as increased bioavailability, reduced side effects, and targeted delivery to specific sites of infection.

Check Digit Verification of cas no

The CAS Registry Mumber 37539-03-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,7,5,3 and 9 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 37539-03:
(7*3)+(6*7)+(5*5)+(4*3)+(3*9)+(2*0)+(1*3)=130
130 % 10 = 0
So 37539-03-0 is a valid CAS Registry Number.
InChI:InChI=1/C10H11N5O3S2/c11-6-8(16)15-7(10(17)18)4(3-20-9(6)15)2-19-5-1-12-14-13-5/h1,6,9H,2-3,11H2,(H,17,18)(H,12,13,14)/t6-,9-/m0/s1

37539-03-0 Well-known Company Product Price

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  • Sigma-Aldrich

  • (C0682410)  Cefatrizine impurity A  European Pharmacopoeia (EP) Reference Standard

  • 37539-03-0

  • C0682410

  • 1,880.19CNY

  • Detail

37539-03-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 7-Amino-3-(1,2,3-triazol-5-ylthiomethyl)-3-cephem-4-carboxylic Acid

1.2 Other means of identification

Product number -
Other names (6R,7R)-7-amino-8-oxo-3-(2H-triazol-4-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:37539-03-0 SDS

37539-03-0Downstream Products

37539-03-0Relevant articles and documents

Process for preparing cephalosporin intermediates

-

, (2008/06/13)

Processes for the preparation of stable, crystalline cephalosporin intermediates of the formula STR1 wherein X is HI or HCl, and Nu and Nu≈ are certain N-containing heterocyclic rings attached via a sulfur atom or a ring nitrogen atom, respectively, which are substantially free of the Δ2 isomer; processes for intermediates in the preparation of the above compounds; and processes for the preparation of broad-spectrum cephalosporin antibiotics.

Use of Bistrimethylsilylated Intermediates in the Preparation of Semisynthetic 7-Amino-3-substituted-cephems. Expedient Syntheses of a New 3-cephalosporin

Walker, Donald G.,Brodfuehrer, Paul R.,Brundidge, Steven P.,Shih, Kun Mao,Sapino, Chester

, p. 983 - 991 (2007/10/02)

Several "one-pot" methods for conversion of 7-ACA (6) to a variety of 7-amino-3-(ammoniomethyl)- or 7-amino-3-methyl>cephalosporin derivatives via bistrimethylsilylated intermediates are presented.For example, bistrimethylsilylation of 7-ACA (6) in 1,1,2-trichlorotrifluoroethane (Freon TF) using HMDS and 3 mol percent TMSI, followed by treatment with 1.15 equiv of TMSI and subsequent reactions with tertiary alicyclic or heteroaromatic amines or heteroaromatic thiols, led to the desired products in good yields.Alternatively, novel reaction of the bistrimethylsilylated derivative 15 with amine/TMSI adducts in Freon TF at 35 deg C provided an alternative approach to some 7-amino-3-(ammoniomethyl)cephalosporins.The solvent dependence of Δ3/Δ2 isomer ratios in quaternization reactions of 11 with N-methylpyrrolidine is presented.Hypotheses for the explanation of experimental results observed on reaction of 15 in Freon TF with amine/TMSI adducts are presented.Acylation of 17 (X = Cl, I) with 8 in aqueous THF provided 18 (BMY-28142) as its sulfate salt in overall yields of 18percent and 43percent, respectively, from 7-ACA (6).

Cephalosporin intermediates

-

, (2008/06/13)

Stable, crystalline cephalosporin intermediates of the formula STR1 wherein X is HI or HCl and Nu and Nu≈ are certain N-containing heterocyclic rings attached via a sulfur atom or a ring nitrogen atom, respectively, which are substantially free of the Δ2 isomer; processes for, and intermediates in, the preparation of the above compounds; and processes for the preparation of broad-spectrum cephalosporin antibiotics.

Cephalosporin antibiotics

-

, (2008/06/13)

Novel cephalosporin antibiotic derivatives.

Trifluoromethylmercaptoacetamidocephalosporins

-

, (2008/06/13)

This invention is directed to antibacterial compounds, in particular, to 7-trifluoromethylmercaptoacetamidocephalosporins.

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