6,6-Dibromopenicillanic acid sulfone

Base Information

• Chemical Name: 6,6-Dibromopenicillanic acid sulfone
• CAS No.: 76646-91-8
• Molecular Formula: C8H9 Br2 N O5 S
• Molecular Weight: 391.037
• Hs Code.: 2941906000
• European Community (EC) Number: 427-200-4
• UNII: 3KI73KUS8T
• DSSTox Substance ID: DTXSID90227466
• Nikkaji Number: J274.611E
• Wikidata: Q27257421
• Mol file: 76646-91-8.mol

Synonyms:76646-91-8;6,6-Dibromopenicillanic acid sulfone;6,6-Dibromopenicillanic Acid S,S-Dioxide;6,6-DIBROMOPENICILLANIC ACID 1,1-DIOXIDE;UNII-3KI73KUS8T;3KI73KUS8T;Sulbactam sodium specified impurity E [EP];EC 427-200-4;(2S,5R)-6,6-dibromo-3,3-dimethyl-4,4,7-trioxo-4lambda6-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-2-carboxylic acid 4,4-dioxide;4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6,6-dibromo-3,3-dimethyl-7-oxo-, 4,4-dioxide, (2S,5R)-;SCHEMBL4614159;DTXSID90227466;MFCD28137728;6,6-Dibromo-1,1-dioxopenicillamic acid;A865437;SULBACTAM SODIUM IMPURITY E [EP IMPURITY];Q27257421;(2S,5R)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid 4,4-dioxide

Chemical Property of 6,6-Dibromopenicillanic acid sulfone

Chemical Property:

• Vapor Pressure: 5.95E-16mmHg at 25°C
• Melting Point: 177-178 °C (decomp)
• Refractive Index: 1.685
• Boiling Point: 600.1°C at 760 mmHg
• PKA: 2.03±0.60(Predicted)
• Flash Point: 316.8°C
• PSA: 100.13000
• Density: 2.29g/cm³
• LogP: 1.31970
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 390.85477
• Heavy Atom Count: 17
• Complexity: 521

Purity/Quality:

99.9% ^*data from raw suppliers

6,6-DibromopenicillanicAcidS,S-Dioxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(N2C(S1(=O)=O)C(C2=O)(Br)Br)C(=O)O)C
• Isomeric SMILES: CC1([C@@H](N2[C@H](S1(=O)=O)C(C2=O)(Br)Br)C(=O)O)C
• Uses: 6,6-Dibromopenicillanic Acid S,S-Dioxide is an impurity of the semi-synthetic β-lactamase inhibitor Sulbactam (S699185). 6,6-Dibromopenicillanic Acid S,S-Dioxide (Sulbactam EP Impurity E) is an impurity of the semi-synthetic β-lactamase inhibitor Sulbactam (S699185).

Technology Process of 6,6-Dibromopenicillanic acid sulfone

There total 9 articles about 6,6-Dibromopenicillanic acid sulfone 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: 90.3%

→ 6,6-dibromopenicillanic acid-1,1-dioxide (76646-91-8)

Guidance literature:

Reference yield: 90.0%

6,6-dibromopenicillanic acid (24158-88-1) → 6,6-dibromopenicillanic acid-1,1-dioxide (76646-91-8)

Guidance literature:

With potassium permanganate; phosphoric acid;

DOI:10.1139/v01-062

Reference yield: 82.2%

(5R,6R)-6-amino-2,2-dimethyl-1,1-dioxopenam-3-carboxylic acid (36091-15-3) + sodium hydrogensulfite → 6,6-dibromopenicillanic acid-1,1-dioxide (76646-91-8)

Guidance literature:

With hydrogen bromide; bromine; sodium nitrite; In methanol; dichloromethane;

upstream raw materials:

(5R,6R)-6-amino-2,2-dimethyl-1,1-dioxopenam-3-carboxylic acid

6,6-dibromopenicillanic acid

6-Aminopenicillanic Acid

Sodium 6,6-dibromopenicillanate

Downstream raw materials:

p-methoxybenzyl 6,6-dibromopenicillinate 1,1-dioxide

(2S,5R)-6,6-dibromo-3,3-dimethyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester

sodium sulbactam

sulbactam

Refernces

• 1、 Mata, Ernesto G.. "β-Lactams on solid support: Mild and efficient removal of penicillin derivatives from Merrifield resin using aluminum chloride". . p. 6335 - 6338. Retrieved 1997.
• 2、 -. "Extends the batanbatan acid synthesis method (by machine translation)". Page/Page column 5-15. . Retrieved 2019/03/31.
• 3、 -. "New indications of troxofine ceftriaxone sodium pharmaceutical preparation for treatment of infection of patients with immunodeficiency". Paragraph 0129; 0131. . Retrieved 2019/11/13.