1003-50-5

Basic information

• Product Name: 4,5-DIBROMO-1-METHYL-1H-IMIDAZOLE
• Synonyms: 4,5-DIBROMO-1-METHYL-1H-IMIDAZOLE;4,5-DIBROMO-1-METHYLIMIDAZOLE;4,5-Dibromo-1-methyl-1H-imidazole 98%;4,5-Dibromo-1-methyl-1H-imidazole98%
• CAS NO: 1003-50-5
• Molecular Formula: C4H4Br2N2
• Molecular Weight: 239.9
• Product Categories: blocks;Bromides;Imidazoles;Imidazol&Benzimidazole;Building Blocks;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 1003-50-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 68-71°C
• Boiling Point: 339 °C at 760 mmHg
• Flash Point: 158.8 °C
• Appearance: /
• Density: 2.22 g/cm³
• Vapor Pressure: 0.000186mmHg at 25°C
• Refractive Index: 1.671
• Storage Temp.: Keep Cold
• PKA: 2.51±0.61(Predicted)
• CAS DataBase Reference: 4,5-DIBROMO-1-METHYL-1H-IMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-DIBROMO-1-METHYL-1H-IMIDAZOLE(1003-50-5)
• EPA Substance Registry System: 4,5-DIBROMO-1-METHYL-1H-IMIDAZOLE(1003-50-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-41-22
• Safety Statements: 26-36/37/39-39
• WGK Germany: 3
• Hazardous Substances Data: 1003-50-5(Hazardous Substances Data)

Usage

General Description

4,5-DIBROMO-1-METHYL-1H-IMIDAZOLE is a chemical compound with the molecular formula C5H5Br2N2. It is a white to off-white crystalline powder that is primarily used as an intermediate in the synthesis of pharmaceutical compounds. 4,5-DIBROMO-1-METHYL-1H-IMIDAZOLE is known for its ability to act as a reactive intermediate in the synthesis of various biologically active compounds, including antiparasitic and antimicrobial agents. It is also used in the production of veterinary medicines and agrochemicals. Additionally, this chemical has applications in the field of organic synthesis and can be used as a building block for the creation of diverse chemical structures. However, it is important to handle 4,5-DIBROMO-1-METHYL-1H-IMIDAZOLE with care, as it may pose certain health hazards and should be used in accordance with proper safety precautions.

InChI:InChI=1/C4H4Br2N2/c1-8-2-7-3(5)4(8)6/h2H,1H3

Upstream product

• 600-39-5 dimethyloxamide 
• 616-47-7 1-methyl-1H-imidazole 
• 1003-91-4 N-methyl-2,4,5-tribromoimidazole 
• 615-35-0 N,N'-dimethyloxamide 
• 7789-69-7 phosphorus pentabromide 
• 67-66-3 chloroform 
• 7726-95-6 bromine 
• 2302-30-9 4,5-dibromo-1H-imidazole 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 1246624-38-3 4,5-dibromo-1-methyl-2-(4-methoxyphenyl)imidazole 
• 1246624-41-8 4,5-dibromo-1-methyl-2-(4-methylphenyl)-1H-imidazole 
• 881997-92-8 4,5-dibromo-1-methyl-2-phenyl-1H-imidazole 
• 53857-60-6 2,4-dibromo-1-methyl-1H-imidazole 
• 25676-75-9 4-bromo-1-methyl-1H-imidazole 
• 19485-35-9 1-methyl-4,5-dicyanoimidazole 

Relevant articles and documents

Efficient and regioselective bromination of aromatic compounds with ethylenebis(N-methylimidazolium) ditribromide (EBMIDTB)

A regioselective and highly efficient method for bromination of phenol and aniline derivatives using ethylenebis(N-methylimidazolium) ditribromide (EBMIDTB) as an efficient reagent in dichloromethane at ambient temperature is reported. The reagent can be recovered and reused several times.

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.

A General Route to 4-Substituted Imidazoles

Literature routes to di(imidazol-4-yl)methanol (1a) dinitrate and tri(imidazol-4-yl)methanol (2a) trihydrochloride were improved to give 32 and 16percent overall yields, respectively; but we failed to synthesize bis- (1b) and tris-(1-methylimidazol-4-yl)methanol (2b) by the methylation of the corresponding N-methoxymethyl compounds (3; x=2 and x=3).Attempted 4-lithiation of the 1,2,5-protected imidazole (4a) with BuLi-TMEDA failed, giving after hydrolysis 1-methyl-5-trimethylsilylimidazole (4b); similar failures were observed for 2,5-dicarboxy-1-methylimidazole, which after metallation with BuLi-TMEDA and hydrolysis afforded 1-methylimidazole-5-carboxylic acid (5).Our attempts to obtain 4-bromo-1-methylimidazole (10a) and 4-bromo-1-ethylimidazole suitable for a halogen-lithium exchange or for Grignard reaction also failed.Attempted selective lithiation of 2-phenylthio-1-tritylimidazole (16) at the 4-position, then theatment with ethyl formate, led only to a mixture of 4- and 5-substituted products in very low yield, and 1-diethoxymethyl-2-phenylthioimidazole (18) was unstable and difficult to purify. 4-Bromoimidazole with two mol equiv. of t-butyl-lithium gives 1,4-dilithioimidazole, which is now shown to provide a general route to 4-substituted imidazoles.