24158-88-1

Basic information

• Product Name: 6,6-DIBROMOPENICILLANIC ACID
• Synonyms: 6,6-DIBROMOPENICILLANIC ACID;(2S-cis)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;(2S,5R)-6,6-Dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid;Einecs 246-046-7;SulbactaM Related CoMpound F;Sulbactam EP Impurity F
• CAS NO: 24158-88-1
• Molecular Formula: C₈H₉Br₂NO₃S
• Molecular Weight: 359.03
• EINECS: 246-046-7
• Product Categories: Heterocycles, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds
• Mol File: 24158-88-1.mol
• Article Data: 25

Chemical Properties

• Melting Point: 142-145 °C
• Boiling Point: 476.6°C at 760 mmHg
• Flash Point: 242°C
• Appearance: /
• Density: 2.17g/cm³
• Vapor Pressure: 2.14E-10mmHg at 25°C
• Refractive Index: 1.704
• PKA: 2.43±0.50(Predicted)
• CAS DataBase Reference: 6,6-DIBROMOPENICILLANIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 6,6-DIBROMOPENICILLANIC ACID(24158-88-1)
• EPA Substance Registry System: 6,6-DIBROMOPENICILLANIC ACID(24158-88-1)

Safety Data

• Hazardous Substances Data: 24158-88-1(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 24158-88-1 differently. You can refer to the following data:
1. 6,6-Dibromopenicillanic Acid is an impurity of the semi-synthetic β-lactamase inhibitor Sulbactam (S699185).
2. 6,6-Dibromopenicillanic Acid (Sulbactam EP Impurity F) is an impurity of the semi-synthetic β-lactamase inhibitor Sulbactam (S699185).

InChI:InChI=1/C8H9Br2NO3S/c1-7(2)3(4(12)13)11-5(14)8(9,10)6(11)15-7/h3,6H,1-2H3,(H,12,13)/t3-,6+/m0/s1

Upstream product

• 551-16-6 6-Aminopenicillanic Acid 
• 69388-93-8 6,6-dibromopenicillanic acid pivaloyloxymethyl ester 
• 551-16-6 6-aminopenicillanic acid 

Downstream Products

• 24138-27-0 methyl-6,6-dibromopenicillanate 
• 98510-71-5 4-Nitrobenzyl 6,6-dibromopenicillanate 
• 35564-99-9 benzyl 6,6-dibromo-2,2-dimethyl-(5R)penam-3α-carboxylate 
• 77442-41-2 dicyclohexylammonium 6α-bromo-penicillanate 
• 24138-28-1 6-bromopenicillanic acid 
• 615551-73-0 (2S,5R,6R)-3,3-Dimethyl-4,4,7-trioxo-6-(2,2,2-trichloro-ethoxycarbonylsulfanylmethyl)-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 615551-69-4 (2S,5R,6R)-6-Acetylsulfanylmethyl-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 615551-61-6 (2S,5R,6S)-6-Acetylsulfanylmethyl-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 615551-74-1 (2S,5R,6R)-6-Mercaptomethyl-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 615551-66-1 (2S,5R,6S)-6-Mercaptomethyl-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 615551-68-3 (2S,5R,6S)-6-Methanesulfonyloxymethyl-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 615551-60-5 (2S,5R,6R)-6-Methanesulfonyloxymethyl-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 615551-70-7 (2S,5R,6R)-6-Mercaptomethyl-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 615551-62-7 (2S,5R,6S)-6-Mercaptomethyl-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 

Relevant articles and documents

Synthesis and evaluation of novel β-lactam inhibitors of human leukocyte elastase

A series of β-lactam derivatives were synthesized and tested to determine the structure-activity relationship for inhibition of human leukocyte elastase (HLE), a serine protease involved in several degenerative lung and tissue diseases. The most potent IC50 values were obtained with neutral hydrophobic 7α-methoxy cephalosporanic acid derivatives. Tryptophanyl-9-fluorenylmethyl ester and N-benzhydryl piperazine derivatives of 7α-methoxy cephalosporanic acid represent two novel HLE inhibitors, with length of action persisting beyond 24 h.

Synthesis method of sulbactam

The invention relates to a synthesis method of sulbactam, and belongs to the field of beta-lactamase inhibitor synthesis. In the method, 6-aminopenicillanic acid (6-APA) as a raw material is dissolvedin an organic solvent, and is adopted together with bromine as substrates under a strong acid condition, 6,6-dibromo penicillanic acid is formed through diazotization bromination in a manner of dropwise adding a sodium nitrite solution, and then one-step oxidation and reduction are performed to obtain sulbactam. According to the method, a hydrogen peroxide one-step oxidation mode is adopted, andthe use of potassium permanganate is avoided from the source, so that the generation of waste salt is reduced, and meanwhile, the use of a large amount of ethyl acetate is avoided. The method not onlyreduces the emission of three wastes from the source and greatly reduces the emission of organic matters and waste salt in the original process, but also greatly reduces the side reaction and the rawmaterial cost.

C type beta-lactamase inhibitor, and preparation method and applications thereof

The invention provides a C type beta-lactamase inhibitor. The C type beta-lactamase inhibitor is 6 alpha-(1R-hydroxy-3(2-thiophene-yl)propyl) penicillic acid, and the structure of the C type beta-lactamase inhibitor is represented by formula 1 in the invention.

Method for preparing sulbactam acid

The invention relates to the field of pharmaceutical synthesis and provides a method for preparing sulbactam acid. The method is used for solving the problem of the traditional synthesis methods thatthe yield is low. The method comprises the following steps: S1. diazotation and bromination reaction: adding bromine, a dilute sulfuric acid solution and sodium nitrite solids into 6-aminopenicillanicacid, so as to obtain a first intermediate, wherein the dilute sulfuric acid solution adopts depleted deuterium water as a solvent; S2. oxidation reaction: dropwise adding potassium permanganate anda dilute sulfuric acid solution into the first intermediate, so as to obtain a second intermediate; and S3. hydrogenation reaction: add strontium powder and a dilute sulfuric acid solution into the second intermediate, thereby obtaining a product, i.e., the sulbactam acid, wherein the dilute sulfuric acid solution adopts depleted deuterium water as a solvent. Through preparing the dilute sulfuricacid solution by adopting the depleted deuterium water as the solvent and adopting the strontium powder as a catalyst, the improvement on reaction activity of dilute sulfuric acid is facilitated, theconversion ratio of reaction is increased, and thus, the increase of reaction yield is facilitated, so that the yield of reaction can be higher than 90%.