1885-22-9

Basic information

• Product Name: Bromomalononitrile
• Synonyms: Bromomalononitrile;2-broMoMalononitrile;Bromodicyanomethane
• CAS NO: 1885-22-9
• Molecular Formula: C₃HBrN₂
• Molecular Weight: 144.95744
• Mol File: 1885-22-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: 65-66℃
• Boiling Point: 147.6°Cat760mmHg
• Flash Point: 43.1°C
• Appearance: /
• Density: 1.849g/cm³
• Vapor Pressure: 4.39mmHg at 25°C
• Refractive Index: 1.51
• CAS DataBase Reference: Bromomalononitrile(CAS DataBase Reference)
• NIST Chemistry Reference: Bromomalononitrile(1885-22-9)
• EPA Substance Registry System: Bromomalononitrile(1885-22-9)

Safety Data

• Hazardous Substances Data: 1885-22-9(Hazardous Substances Data)

Usage

Preparation

Bromomalononitrile was prepared by bromination of malononitrile by the method of Ferris, et al.5 To this end, bromine (48.5 g, 0.30 mol) was added over a period of 5 hr to malononitrile (20 g, 0.30 mol) dissolved in water (300 mL) in an ice bath, and kept overnight under those conditions. A slight brown-white precipitate separated from the solution. It was washed with water and taken up in CHCl3 (100 mL). After drying (Na2SO4) and concentrating under reduced pressure to about one half the original volume, the solution was cooled in a refrigerator to deposit colorless crystals, which were then purified by recrystallization from CHCl3 to give 21 g (48%) of the desired bromomalononitrile , mp 63-64°C (Ferris, et al.,5 reported 20% yield).Org. Synth. 1998, 75, 210DOI: 10.15227/orgsyn.075.0210

InChI:InChI=1/C3HBrN2/c4-3(1-5)2-6/h3H

Upstream product

• 1885-23-0 dibromomalononitrile 
• 7732-18-5 water 
• 109-77-3 malononitrile 
• 7726-95-6 bromine 
• 41470-37-5 Dicyanomethyl-anion 

Downstream Products

• 23767-82-0 3-furan-2-yl-cyclopropane-1,1,2,2-tetracarbonitrile 
• 13017-67-9 3,3-dimethylcyclopropane-1,1,2,2-tetracarbonitrile 
• 23767-79-5 3-phenylcyclopropane-1,1,2,2-tetracarbonitrile 
• 90594-33-5 3-Methyl-1,1,2,2-cyclopropantetracarbonitril 
• 24543-06-4 ethyl 1,2,2-tricyano-3,3-dimethylcyclopropane-1-carboxylate 
• 56991-09-4 3-allyl-4-amino-2-imino-2,3-dihydro-thiazole-5-carbonitrile 
• 6904-07-0 sec-butylmalononitrile 
• 30963-90-7 cyclopentylidenemalononitrile 
• 13764-23-3 2-(2-bromo-1,2-dimethylpropyl)malononitrile 
• 13764-28-8 2,2,3-trimethyl-1,1-cyclopropanedicarbonitrile 
• 6129-65-3 2-(2-bromo-1,1,2-trimethylpropyl)malononitrile 
• 1195-70-6 3,3-dicyano-1,1,2,2-tetramethylcyclopropane 
• 62897-31-8 (E)-2,7-Dicyano-4,5-diphenyl-octa-2,4,6-trienedinitrile 
• 62897-37-4 3-Brom-1-hepten-1.1-dicarbonitril 

Relevant articles and documents

Ethylenebis(N-methylimidazolium) ditribromide (EBMIDTB): An efficient reagent for the monobromination of 1,3-diketones and β-ketoesters

Ethylenebis(N-methylimidazolium) ditribromide, a stable crystalline solid, is easily prepared by reaction of the corresponding dibromide salt with bromine in n-hexane. 1,3-Diketones and β-ketoesters can be brominated chemoselectively to the corresponding α-monobrominated products by using this reagent at 0-5°C. Under the same reaction conditions, diethyl malonate, ethyl cyanoacetate, and malonitrile were monobrominated at moderate yield.

Chemical reactivity of 3-hydrazino-5,6-diphenyl-1,2,4-triazine towards π-acceptors activated carbonitriles

Behaviour of 3-hydrazino-5,6-diphenyl-1,2,4-triazine 1 as electron donor towards different electron acceptors activated carbonitriles has been investigated and a novel fused heterocyclic system and 2,3-disubstituted 1,2,4-triazines have been obtained. Compound 1 reacts with 1,2-dicyanobenzene as π-acceptor in DMF to form benzencarboximidamide 16, while reaction of 1 with a-bromomalononitrile 17 in boiling DMF affords compound 18. On the other hand, compound 1 reacts with tetracyanoethane 23 in DMF to yield compound 24. The route of reaction in DMF indicates that charge-transfer complexation is the key intermediate to obtain new heterocyclic systems. Structures of the products are established by MS, IR, UV-Vis, CHN and 1H NMR spectral data.

Microwave-assisted synthesis of some BI- and tricyclic pyrimidine derivatives

Pyrimidine derivatives 4a-4c was prepared by a Biginelli cyclocondensation of β-ketoesters, aryl aldehydes, and thiourea derivatives under microwave irradiation. A simple and fast synthesis of bicyclic pyrimidine derivatives 6a-6c was performed by microwave-assisted reaction of 4a-4c with bromomalononitrile (5). Reaction of bicyclic pyrimidines 6a-6c with HCO2H and HONH3Cl under microwave irradiation gave tricyclic pyrimidines 7a-7c and 8a-8c respectively.