1003-21-0

Basic information

• Product Name: 5-BROMO-1-METHYL-1H-IMIDAZOLE
• Synonyms: 5-BROMO-N-METHYLIMIDAZOLE;5-BROMO-1-METHYL-1H-IMIDAZOLE;5-BROMO-1-METHYLIMIDAZOLE;5-Bromo-1-methylimidazole,97%;5-BroMo-1-Methyl-1H-iMidazole 97%;1H-Imidazole,5-bromo-1-methyl-
• CAS NO: 1003-21-0
• Molecular Formula: C₄H₅BrN₂
• Molecular Weight: 161
• Product Categories: blocks;Bromides;Imidazoles;pharmacetical;Imidazol&Benzimidazole;Halogenated Heterocycles;Heterocyclic Building Blocks;ImidazolesBuilding Blocks;Building Blocks;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 1003-21-0.mol
• Article Data: 11

Chemical Properties

• Melting Point: 40-44 °C(lit.)
• Boiling Point: 120°C 15mm
• Flash Point: 180 °F
• Appearance: White to tan crystalline solid
• Density: 1.693 g/cm³
• Vapor Pressure: 0.0106mmHg at 25°C
• Refractive Index: 1.606
• Storage Temp.: Keep Cold
• PKA: 5.25±0.10(Predicted)
• CAS DataBase Reference: 5-BROMO-1-METHYL-1H-IMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-1-METHYL-1H-IMIDAZOLE(1003-21-0)
• EPA Substance Registry System: 5-BROMO-1-METHYL-1H-IMIDAZOLE(1003-21-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3335
• WGK Germany: 3
• Hazardous Substances Data: 1003-21-0(Hazardous Substances Data)

Usage

Chemical Properties

White to tan crystalline solid

InChI:InChI=1/C4H5BrN2/c1-7-3-6-2-4(7)5/h2-3H,1H3

Upstream product

• 616-47-7 1-methyl-1H-imidazole 
• 7664-93-9 sulfuric acid 
• 2302-25-2 4-bromo-1 H-imidazole 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 
• 2302-25-2 5-bromo-1H-imidazole 
• 141524-72-3 4-bromo-1,3-dimethyl-1H-imidazolium iodide 

Downstream Products

• 1196707-69-3 (R)-1-methyl-N-(1-phenylethyl)-1H-imidazole-5-carboxamide 
• 501421-81-4 (R,S)-6-[(4-chlorophenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-4-(3-(3-hydroxy-3-methylbutyn-1-yl)-phenyl)-1-methyl-1H-quinolin-2-one 
• 1431700-88-7 C₂₄H₂₅N₅O₂ 
• 1318212-69-9 5-(diphenylphosphino)-1-methyl-1H-imidazole 
• 480439-45-0 5-[(trimethylsilyl)ethynyl]-1-methylimidazole 
• 1227277-90-8 6-((4-chlorophenyl)(hydroxy)(1-methyl-1H-imidazol-5-yl)methyl)-4-(3-methoxyphenyl)-1-methyl-1,8-naphthyridin-2(1H)-one 
• 1227279-34-6 6-((4-chlorophenyl)(hydroxy)(1-methyl-1H-imidazol-5-yl)methyl)-1-methyl-4-(3-((trimethylsilyl)ethynyl)phenyl)-1,8-naphthyridin-2(1H)-one 
• 1227277-71-5 4-(3-chlorophenyl)-6-((4-chlorophenyl)(hydroxy)(1-methyl-1H-imidazol-5-yl)methyl)-1-methyl-1,8-napthyridin-2(1H)-one 
• 1218910-50-9 C₁₀H₉BrN₂ 
• 1187312-98-6 C₃₁H₂₆FN₅O₂S 
• 1071444-92-2 C₂₃H₂₁N₃O₃ 
• 1047645-35-1 1,1-dimethylethyl [2-({[5-(1-methyl-1H-imidazol-5-yl)-2-thienyl]carbonyl}amino)-3-phenylpropyl]carbamate 
• 883738-23-6 3-(3-methyl-3H-imidazol-4-yl)-phenylboronic acid 
• 865798-15-8 ethyl 5-bromo-1-methyl-1H-imidazole-2-carboxylate 

Relevant articles and documents

Direct, Regioselective N-Alkylation of 1,3-Azoles

Regioselective N-alkylation of 1,3-azoles is a valuable transformation. Organomagnesium reagents were discovered to be competent bases to affect regioselective alkylation of various 1,3-azoles. Counterintuitively, substitution selectively occurred at the more sterically hindered nitrogen atom. Numerous examples are provided, on varying 1,3-azole scaffolds, with yields ranging from 25 to 95%.

Synthesis of chiral pilocarpine analogues via a C-8 ketone intermediate.

The synthesis of a chiral pilocarpine analogue 3 in which the lactone ring is replaced by an oxazolidinone and the bridging methylene group is in the ketone oxidation state has been accomplished. The utility of this compound as a key intermediate for the preparation of more complex structures was demonstrated by its reduction to two alcohol epimers and its reaction with a methylene ylide.

SYNTHESIS OF 5-ARYLTHIO-3-METHYL-L-HISTIDINE, A MODEL FOR THE STARFISH ALKALOID IMBRICATINE

Syntheses of 3 methyl-5-phenylthio-L-histidine (8a) and 3-methyl-5-(1-naphthyl)thio-L-histidine (8b), selected as models for the asteroid alkaloid imbricatine (7), have now become feasible through a 10-step route starting from 4(5)-bromoimidazole (9).The key steps involve replacement of the 4-bromo group by an arylthio group in the aldehyde (14) and construction of the L-alanine moiety in the chlorides (17a,b) by the "bis-lactim ether" method.