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Bromonitrin C

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Bromonitrin C
Category Antibiotics
Catalog number BBF-00590
CAS 32736-23-5
Molecular Weight 424.87
Molecular Formula C10H5Br3N2O2
Purity 95%

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Capabilities & Facilities

Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

Bromonitrin C is an antibiotic produced by Pseudomonas pyrrolnimica in a bromide-containing medium. It has anti-Gram-positive bacteria, Penicillium chrysogenum, Trichophyton interdigita and Candida albicans.

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Synonyms 2,3-dibromo-4-(5-bromo-2-nitrophenyl)-1H-pyrrole;BromonitrinC;32736-23-5
IUPAC Name 2,3-dibromo-4-(5-bromo-2-nitrophenyl)-1H-pyrrole
Canonical SMILES C1=CC(=C(C=C1Br)C2=CNC(=C2Br)Br)[N+](=O)[O-]
InChI InChI=1S/C10H5Br3N2O2/c11-5-1-2-8(15(16)17)6(3-5)7-4-14-10(13)9(7)12/h1-4,14H
InChI Key ODHIIACYHYEABI-UHFFFAOYSA-N
Appearance Orange Needle Crystal
Antibiotic Activity Spectrum Gram-positive bacteria; fungi
Melting Point 84-85°C
Solubility Soluble in Chloroform, Methanol, water, acetone
1.Cyclic nitriles: diastereoselective alkylations.
Fleming FF1, Gudipati S, Zhang Z, Liu W, Steward OW. J Org Chem. 2005 May 13;70(10):3845-9.
[reaction: see text] Diastereoselective alkylations of metalated conformationally locked 4-tert-butylcyclohexanecarbonitrile are highly diastereoselective with magnesium and copper counterions but only modestly diastereoselective with lithium as the counterion. Selective generation of diverse metalated nitriles is readily achieved through bromine-magnesium, -copper, and -lithium exchange reactions of the corresponding bromonitrile or, for lithium, by deprotonating the parent nitrile with lithium diethylamide. Collectively, high alkylation stereoselectivities correlate with the retentive alkylations of C-metalated nitriles, whereas N-lithiated nitriles alkylate with modest selectivity, reflecting minimal steric differences in the corresponding axial and equatorial electrophile trajectories.
2.The first enantioenriched metalated nitrile possessing macroscopic configurational stability.
Carlier PR1, Zhang Y. Org Lett. 2007 Mar 29;9(7):1319-22. Epub 2007 Mar 10.
[structure: see text]. Magnesium-bromine exchange on enantiopure cyclopropyl bromonitrile 5 at -100 degrees C for 1 min followed by a D2O quench gives the deuterionitrile in 81% ee (retention); additional trapping experiments establish t(1/2)(rac) = 11.4 h at -100 degrees C. These experiments provide the first glimpse into the stereochemical aspects of Mg-Br exchange. The intermediate formed is the first metalated nitrile demonstrated to possess macroscopic configurational stability.

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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