Bromobimane or monobromobimane is a

heterocyclic compound A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and ...

and bimane dye that is used as a reagent in

biochemistry Biochemistry or biological chemistry is the study of chemical processes within and relating to living organisms. A sub-discipline of both chemistry and biology, biochemistry may be divided into three fields: structural biology, enzymology and ...

. While bromobimane itself is essentially nonfluorescent, it

alkylate An alkylation unit (alky) is one of the conversion processes used in petroleum refineries. It is used to convert isobutane and low-molecular-weight alkenes (primarily a mixture of propene and butene) into alkylate, a high octane gasoline component ...

thiol In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl gro ...

groups, displacing the bromine and adding the fluorescent tag (λ_emission = 478 nm) to the thiol. Its alkylating properties are comparable to

iodoacetamide 2-Iodoacetamide is an alkylating agent used for peptide mapping purposes. Its actions are similar to those of iodoacetate. It is commonly used to bind covalently with the thiol group of cysteine so the protein cannot form disulfide bonds. Also used ...

Synthesis

Bromobimane is prepared from 3,4-dimethyl-2-pyrazolin-5-one (a condensation product of ethyl 2-methylacetoacetate with hydrazine) by chlorination followed by basic treatment; with aqueous K₂CO₃ under heterogeneous conditions, the required ''syn''-bimane, 2,3,5,6-tetramethyl-1''H'',7''H''-pyrazolo

,2-''a'' The comma is a punctuation mark that appears in several variants in different languages. It has the same shape as an apostrophe or single closing quotation mark () in many typefaces, but it differs from them in being placed on the baseline o ...

yrazole-1,7-dione, is the major product. It can then be selectively brominated to the target bromobimane (with 1 equivalent of Br₂; or dibromobimane, if 2 equivalents of Br₂ are used):{{cite journal, author1=Kosower, Edward M., author2=Pazhenchevsky, Barak, title=Bimanes. 5. Synthesis and Properties of ''syn''- and ''anti''-1,5-Diazabicyclo .3.0ctadienediones (9,10-Dioxabimanes), journal=Journal of the American Chemical Society, volume=102, issue=15, pages=4983–4993, year=1980, doi=10.1021/ja00535a028 Bromobimanes are light-sensitive compounds and should be kept refrigerated and protected from light.

References

Alkylating agents Organobromides Lactams Hydrazides