16681-59-7

Basic information

• Product Name: 2-Bromo-1-methyl-1H-imidazole
• Synonyms: 2-BROMO-1-METHYL-1H-IMIDAZOLE;2-BROMO-1-METHYLIMIDAZOLE;2-Bromo-1-methyl-1H-imidazole 97%;1-METHYL-2-BROMOIMIDAZOLE;3-METHYL-3-PHENYLBUTANOIC ACID;1-Methyl-2-bromo-1H-imidazole;2-Bromo-N-methylimidazole;1H-Imidazole,2-bromo-1-methyl-
• CAS NO: 16681-59-7
• Molecular Formula: C₄H₅BrN₂
• Molecular Weight: 161
• Product Categories: blocks;Bromides;Imidazoles;Imidazol&Benzimidazole;Halogenated Heterocycles;Heterocyclic Building Blocks;ImidazolesBuilding Blocks
• Mol File: 16681-59-7.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 172 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to pale yellow to pink/Liquid
• Density: 1.649 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.5440(lit.)
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• PKA: 3.83±0.25(Predicted)
• CAS DataBase Reference: 2-Bromo-1-methyl-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-1-methyl-1H-imidazole(16681-59-7)
• EPA Substance Registry System: 2-Bromo-1-methyl-1H-imidazole(16681-59-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-38-41
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 16681-59-7(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 16681-59-7 differently. You can refer to the following data:
1. 2-Bromo-1-methylimidazole is used in in pharmaceuticals, drug candidates, ligands for transition metal catalysts and other molecular functional materials.
2. 2-Bromo-1-methyl-1H-imidazole can be used in the synthesis of the following:N-(4-methoxyphenyl)-1-methyl-1H-imidazol-2-amine via C-N coupling with p-anisidine1,2-bis[2-methyl-5-(1-methyl-1H-imidazol-2-yl)-3-thienyl]-cyclopentene, a ligand which can form bimetallic platinum(II) complex with potent cytotoxic activity

Upstream product

• 616-47-7 1-methyl-1H-imidazole 
• 60-56-0 1-methyl-1,3-dihydro-imidazole-2-thione 

Downstream Products

• 912844-34-9 C₂₃H₂₁N₃O₃ 
• 960067-92-9 C₁₀H₉BrN₂ 
• 1310383-27-7 (4-(1-methyl-1H-imidazol-2-yl)phenyl)boronic acid 
• 1141892-94-5 2-(3,4-Dimethoxy-phenyl)-1-methyl-1H-imidazole 
• 1126369-73-0 4-(benzyloxy)-N-(2-methyl-5-(1-methyl-1H-imidazol-2-yl)phenyl)benzamide 
• 1126368-31-7 N-[4-chloro-2-methyl-5-(1-methyl-1H-imidazol-2-yl)phenyl]-4-(pyridin-2-ylmethoxy)benzamide 
• 113049-35-7 1-(1-methyl-1H-imidazol-2-yl)piperazine 
• 872327-70-3 N-methyl-2-(2,4-difluorophenyl)imidazole 
• 53857-59-3 2,5-dibromo-1-methyl-1H-imidazole 

Relevant articles and documents

New cephalosporins and 7α-methoxy cephalosporins. Chemistry and biological activities

The synthesis and the in vitro activity of a number of cephalosporins and 7α-methoxy cephalosporins having 7-acyl subsituents derived from 1-methyl-4 (or 5)-nitro-1H-imidazolyl-thioacetic acids are described. The microbiological profile is influenced by the position of both the nitro group and the side-chain sulfur atom on the 1-methyl imidazole, and by the nature of the 3-substituent.

Reaction of imidazoles with cyanogen bromide: Cyanation at N 1 or bromination at C 2?

The reaction in acetonitrile solution of a number of imidazoles (1H-, 1-methyl-, 2-methyl-, 4-methyl-, 1,2-, 1,4- and 1,5-dimethyl-, 1-ethyl-, 1-benzyl- and 1-butyl-imidazole) and imidazole complexes ([Co(NH3)5(imH)](ClO4)3, [Co(NH3)5(im)] (ClO4)2 and [Co(NH3)5(1-Meim)] (ClO4)3) with BrCN has been studied. Those imidazoles bearing an N-alkyl substituent and having a hydrogen at C2 react to give the 2-bromo products, while the N-H imidazoles react to give W-cyano derivatives. The product(s) from the reaction of 1,2-dimethylimidazole with BrCN could not be characterized. Of the complexes, only [Co(NH3)5(im)] (ClO4)2 reacts, giving the 2-bromo product. Our observations suggest a lone pair on a ring nitrogen atom is necessary for an imidazole to react with BrCN, and a possible mechanism is suggested. The X-ray structure of 2-methylimidazole-1-carbonitrile is reported. Crystal data (-143°C) for C5H5N3: monoclinic, P21/c, a 10.201(5), b 7.110(3), c 7.227(3) A, β 100.47(2)°, V 515.4(4) A3, Z 4, dcalcd 1-380 g cm-3. Refinement of the structure converged with R1 0.0444 for 1183 reflections with Fo > 4F(Fo) and ωR2 0.1259 for all 1278 data.

Tetrahalogenomethanes: Simple reagents for the synthesis of monohalogenated and mixed dihalogenated aromatic heterocycles via metal-halogen exchange from lithium compounds

Tetrabromo- or tetrachloromethane and 2-lithio derivatives of aromatic heterocycles rapidly produce the corresponding 2-bromo or 2-chloro derivatives in high yields through a metal-halogen exchange mechanism. This kind of reaction was also used to obtain, in good yields, 5-bromo-2-chlorothiazole and 5-bromo-2-chloro-N-methylimidazole.

PI4KIIIBETA INHIBITORS

The invention relates to compounds of formula (I) which are inhibitors of kinase activity, pharmaceutical formulations containing the compounds and their uses in treating and preventing viral infections and disorders caused or exacerbated by the viral inf

T -BuONa-mediated direct C-H halogenation of electron-deficient (hetero)arenes

An efficient halogenation of electron-deficient (hetero)arenes is described. The reaction utilizes common t-BuONa as a catalyst (for iodination) or a promoter (for bromination and chlorination), and perfluorobutyl iodide, CBr4 or CCl4 as the readily-available halogenating agents, respectively. The protocol features broad scope, high efficiency, mild conditions and gram scalability. An ionic pathway involving halogen bond formation and halophilic attack is proposed. The utility of the resulting iodinated heteroarenes is demonstrated in visible light-mediated Caryl-Caryl cross-coupling reaction.