CAS 76646-91-8 6,6-Dibromopenicillanic acid sulfone (HCID 1427720)

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Basic information

CAS: 76646-91-8
Standard SMILES: CC1(C)[C@H](C(=O)O)N2C(=O)C(Br)(Br)[C@H]2S1(=O)=O
InChIKey: DZYBRGUNKNPEKM-BBIVZNJYSA-N
Molecular formula: C8H9Br2NO5S
Average molar mass: 391.04 g/mol
Monoisotopic mass: 388.85681759

Names & identifiers

Preferred name: 6,6-Dibromopenicillanic acid sulfone
IUPAC: (2S,5R)-6,6-dibromo-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
English name: (3S)-6,6-DIBROMO-2,2-DIMETHYLPENAM-3-CARBOXYLIC ACID 1,1-DIOXIDE
Molecular formula: C8H9Br2NO5S
Molecular weight: 391.03

Names & synonyms

6,6-Dibromopenicillanic acid sulfone6,6-DIBROMOPENICILLANIC ACID 1,1-DIOXIDE(2S,5R)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxideUNII-3KI73KUS8T3KI73KUS8TSulbactam sodium specified impurity E [EP]DTXSID90227466EC 427-200-4(2S,5R)-6,6-Dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid 4,4-dioxide4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6,6-dibromo-3,3-dimethyl-7-oxo-, 4,4-dioxide, (2S,5R)-SULBACTAM SODIUM IMPURITY E [EP IMPURITY]SULBACTAM SODIUM IMPURITY E (EP IMPURITY)

Show more names

SulbactaM Related CoMpound ESulbactam EP Imp ESULBACTUM RELAED COMPOUND ESulbactam Sodium EP Impurity ESulbactam Related Compound E / EP Impurity ESulbactam Impurity 5(Sulbactam EP Impurity E)Sulbactam EP Impurity E (Sulbactam USP Related Compound E)

4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6,6-dibromo-3,3-dimethyl-7-oxo-, 4,4-dioxide, (2S,5R)-RefChem:103758DTXCID90149957Sulbactam sodium specified impurity E427-200-476646-91-86,6-Dibromopenicillanic Acid S,S-DioxideSulbactam EP Impurity E

Properties

Computed structural properties

XLogP: 0.6
Topological polar surface area: 100 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 5
Rotatable bonds: 1
Heavy atoms: 17
Formal charge: 0
Complexity: 521

Physicochemical properties

Melting point: 177 · 177-178 °C (decomp)
Boiling point: 600.1 · 600.1±55.0 °C(Predicted)
Density: 2.29 · 2.29±0.1 g/cm3(Predicted)
storage temp.: -20 °C · -20°C
pka: 2.03 · 2.03±0.60(Predicted)
Major Application: pharmaceutical
InChI: 1S/C8H9Br2NO5S/c1-7(2)3(4(12)13)11-5(14)8(9,10)6(11)17(7,15)16/h3,6H,1-2H3,(H,12,13)/t3-,6+/m0/s1
InChIKey: DZYBRGUNKNPEKM-BBIVZNJYSA-N
SMILES: [S]1(=O)(=O)[C@H]2N([C@H](C1(C)C)C(=O)O)C(=O)C2(Br)Br
FDA UNII: 3 KI73KUS8T · 3KI73KUS8T
UNSPSC Code: 41116107 · 41116107
NACRES: 24 · NA.24
Symbol(GHS): 5 · GHS05,GHS07
Signal word: Danger
Hazard statements: 302 · H302-H315-H317-H318

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P272, P280, P301+P317, P302+P352, P305+P354+P338, P317, P321, P330, P332+P317, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P272, P280, P301+P317, P302+P352, P305+P354+P338, P317, P321, P330, P332+P317, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

Hazard information

Regulatory InformationStatus: Active Update: 15-12-2008 https://echa.europa.eu/registration-dossier/-/registered-dossier/13949

Hazard Classes and Categories · 3 items

Acute Tox. 4 (100%)

Acute toxicity - category 4

Acute Tox. 4 *

Safety data

wgk: WGK 3
hs_code: 2941906000
Signal word: Danger
Symbol(GHS): GHS05,GHS07
Storage Class: 11 - Combustible Solids
Hazard statements: H302-H315-H317-H318
REACH Registrations: Inactive
Hazard Classifications: Acute Tox. 4 OralEye Dam. 1Skin Irrit. 2Skin Sens. 1
Precautionary statements: P264-P270-P301+P312-P330-P501-P264-P280-P302+P352-P321-P332+P313-P362-P261-P272-P280-P302+P352-P333+P313-P321-P363-P501-P280-P305+P351+P338-P310

Chemistry & industry

Applications

Uses6,6-Dibromopenicillanic Acid S,S-Dioxide is an impurity of the semi-synthetic β-lactamase inhibitor Sulbactam (S699185).

Uses6,6-Dibromopenicillanic Acid S,S-Dioxide (Sulbactam EP Impurity E) is an impurity of the semi-synthetic β-lactamase inhibitor Sulbactam (S699185).