Bromonitrin C
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| Category | Antibiotics |
| Catalog number | BBF-00590 |
| CAS | 32736-23-5 |
| Molecular Weight | 424.87 |
| Molecular Formula | C10H5Br3N2O2 |
| Purity | 95% |
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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.
Specification
| 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 |
Properties
| Appearance | Orange Needle Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; fungi |
| Melting Point | 84-85°C |
| Solubility | Soluble in Chloroform, Methanol, water, acetone |
Reference Reading
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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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
