18791-98-5

Usage

Uses

Used in Pharmaceutical Industry:
3-Bromothiophene-2-carbonitrile is used as a building block for the synthesis of various pharmaceutical compounds. Its reactivity and functional groups make it a valuable intermediate in the development of new drugs.
Used in Organic Synthesis:
3-Bromothiophene-2-carbonitrile is used as a key intermediate in the synthesis of complex organic molecules. Its bromine and nitrile groups facilitate various chemical reactions, making it a versatile component in the construction of a wide range of organic compounds.
Used in Chemical Research:
3-Bromothiophene-2-carbonitrile is used as a reagent in chemical research, particularly in the study of cross-coupling reactions and electrochemical properties. Its unique structure allows for the exploration of new reaction pathways and the development of novel synthetic methods.
Safety Considerations:
When handling 3-Bromothiophene-2-carbonitrile, appropriate protective measures must be taken, as it may cause skin and eye irritation, and is harmful if swallowed or inhaled. Its exact physical and chemical properties such as boiling point or density may vary depending on the specific conditions and purity levels.

InChI:InChI=1/C5H2BrNS/c6-4-1-2-8-5(4)3-7/h1-2H

Upstream product

• 89283-98-7 3-bromo-thiophene-2-carbaldehyde oxime 
• 3140-93-0 2,3-dibromothiophen 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 930-96-1 3-bromo-2-thiophenecarboxaldehyde 
• 24287-92-1 2-Bromo-3-iodothiophene 

Downstream Products

• 78031-18-2 3-bromo-2-carboxamidothiophene 
• 670749-52-7 3-(6-Chloro-5-phenyl-1H-indazol-3-ylamino)thiophene-2-carbonitrile 
• 651353-89-8 1,1-dimethylethyl (4S)-4-[(2R)-2-[(2-cyano-3-thienyl)thio]-2-phenylethyl]-2,2-dimethyl-3-oxazolidinecarboxylate 
• 56489-05-5 3-aminothiophene-2-carbonitrile 
• 1013926-24-3 [2-((4S)-4-tert-butyl-4,5-dihydrooxazol-2-yl)phenyl](thiophene-2-carbonitrile)amine 
• 1013926-22-1 [2-((4S)-4-isopropyl-4,5-dihydrooxazol-2-yl)phenyl](thiophene-2-carbonitrile)amine 
• 1013926-23-2 [2-((4S)-4-phenyl-4,5-dihydrooxazol-2-yl)phenyl](thiophene-2-carbonitrile)amine 
• 1013926-21-0 {2-[(4S)-4-benzyl-4,5-dihydrooxazol-2-yl]phenyl}(thiophene-2-carbonitrile)amine 
• 1219628-68-8 3-(6-hydroxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)naphthalen-2-yl)thiophene-2-carbonitrile 
• 189269-12-3 3-(3-tert-Butyldiphenylsilyloxymethyl-2,4-dimethylphenyl)-2-[4-(methylcarbamoyl)cinnamoylaminomethyl]-thiophene 
• 189269-11-2 2-aminomethyl-3-(3-tert-butyldiphenylsilyloxymethyl-2,4-dimethylphenyl)thiophene 

Relevant academic research and scientific papers

Regiocontrolled Halogen Dance of Bromothiophenes and Bromofurans

The LDA (lithium diisopropylamide)-promoted regiocontrolled halogen dance of α-bromothiophenes and α-bromofurans is described. Bromothiophenes bearing a diethyl acetal moiety undergo selective deprotonation at the β-position adjacent to the bromo group. In contrast, oxazoline, ester, and amide groups act as directing groups in the initial lithiation step to generate a carbanion at the β-position neighboring the directing group to exclusively give the other regioisomer. These results can be applied to the regiocontrolled halogen dance of bromofuran derivatives.

Schmidt reaction in ionic liquids: Highly efficient and selective conversion of aromatic and heteroaromatic aldehydes to nitriles with [BMIM(SO3H)][OTf] as catalyst and [BMIM][PF6] as solvent

A mild and selective method is presented for the conversion of aromatic and heteroaromatic aldehydes to nitriles via the Schmidt reaction with TMSN 3 by using [BMIM(SO3H)][OTf] as catalyst and [BMIM][PF6] as solvent. The method offers high yields and simple product isolation, and avoids the use of liquid superacids or corrosive Lewis acids commonly employed for this transformation. It also offers some potential for recycling/reuse of the IL solvent.

Synthesis of 2,3-Substituted Thienylboronic Acids and Esters

A noncryogenic protocol for the synthesis of 2-substituted 3-thienylboronic acids and esters as well as 3-substituted 2-thienylboronic acids and esters has been developed. Electrophiles were introduced regiospecifically in the 2-position of 2,3-dibromothiophene and in the 3-position of 2-bromo-3-iodothiophene by halogen-magnesium exchange followed by quenching with electrophiles. Palladium-catalyzed borylation of the 2,3-substituted halothiophenes with pinacolborane and P(t-Bu)3 as ligand for Pd produced 9 and 10. The borylation protocol was tolerated by a range of functional groups; however, strongly electron-withdrawing substituents decreased the stability of the thienylboronic acids and esters.