Methyl (2S-cis)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate

Base Information

• Chemical Name: Methyl (2S-cis)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate
• CAS No.: 24138-27-0
• Molecular Formula: C9H11 Br2 N O3 S
• Molecular Weight: 373.065
• European Community (EC) Number: 246-027-3
• DSSTox Substance ID: DTXSID00946954
• Nikkaji Number: J242.737K
• Wikidata: Q82924706
• Mol file: 24138-27-0.mol

Synonyms:24138-27-0;Methyl (2S-cis)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate;EINECS 246-027-3;methyl (2S,5R)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;C9H11Br2NO3S;C9-H11-Br2-N-O3-S;METHYL (2S-CIS)-6,6-DIBROMO-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLATE;SCHEMBL9385846;DTXSID00946954;methyl 6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;6,6-Dibromopenicillanic acid methyl ester;Methyl(2s-cis)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Chemical Property of Methyl (2S-cis)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate

Chemical Property:

• Vapor Pressure: 8.84E-07mmHg at 25°C
• Boiling Point: 405.3°Cat760mmHg
• Flash Point: 198.9°C
• PSA: 71.91000
• Density: 1.96g/cm³
• LogP: 1.64570
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 372.88059
• Heavy Atom Count: 16
• Complexity: 372

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(N2C(S1)C(C2=O)(Br)Br)C(=O)OC)C
• Isomeric SMILES: CC1([C@@H](N2[C@H](S1)C(C2=O)(Br)Br)C(=O)OC)C

Technology Process of Methyl (2S-cis)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate

There total 8 articles about Methyl (2S-cis)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

6,6-dibromopenicillanic acid (24158-88-1) + methyl iodide (74-88-4) → methyl-6,6-dibromopenicillanate (24138-27-0)

Guidance literature:

With sodium hydrogencarbonate; In N,N-dimethyl-formamide; for 16h; Ambient temperature;

DOI:10.1021/jo00356a020

Reference yield:

brobactam (26631-90-3) + methyl iodide (74-88-4) → methyl-6,6-dibromopenicillanate (24138-27-0)

Guidance literature:

In N-methyl-acetamide; ethyl acetate; 6,6-dibromopenicillanic acid;

Reference yield:

6-diazo-penicillanic acid methyl ester (56414-10-9) → methyl-6,6-dibromopenicillanate (24138-27-0)

Guidance literature:

With bromine; In tetrachloromethane;

upstream raw materials:

diazomethane

6,6-dibromopenicillanic acid

6-Aminopenicillanic Acid

6-diazo-penicillanic acid methyl ester

Downstream raw materials:

(2S,5R,6S)-6-Bromo-6-((S)-1-hydroxy-ethyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester

methyl 6-α-bromo-6-β-<(1R)-hydroxyethyl>penicillanate

methyl (3S,5R,6R)-6-bromo-6-<(S)-1-hydroxyethyl>penicillanate

methyl (3S,5R,6R)-6-bromo-6-<(R)-1-hydroxyethyl>penicillanate