141524-74-5

Basic information

• Product Name: 4-BROMO-1-METHYL-1H-IMIDAZOLE-5-CARBOXALDEHYDE
• Synonyms: 4-BROMO-1-METHYLIMIDAZOLE-5-CARBOXALDEHYDE;4-BROMO-1-METHYL-1H-IMIDAZOLE-5-CARBOXALDEHYDE;4-Bromo-1-methyl-1H-imidazole-5-carboxaldehyde 98%;4-BroMo-1-Methyl-1H-iMidazol-5-carbaldehyde;1H-IMidazole-5-carboxaldehyde, 4-broMo-1-Methyl-;4-BroMo-1-Methyl-1H-iMidazole-5-carbaldehyde;5-bromo-3-methylimidazole-4-carbaldehyde
• CAS NO: 141524-74-5
• Molecular Formula: C₅H₅BrN₂O
• Molecular Weight: 189.01
• Product Categories: Aldehydes;blocks;Bromides;Imidazoles;Imidazol&Benzimidazole
• Mol File: 141524-74-5.mol

Chemical Properties

• Melting Point: 60-64°C
• Boiling Point: 349.115 °C at 760 mmHg
• Flash Point: 164.939 °C
• Appearance: /
• Density: 1.738 g/cm³
• Vapor Pressure: 4.81E-05mmHg at 25°C
• Refractive Index: 1.621
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 1.12±0.61(Predicted)
• CAS DataBase Reference: 4-BROMO-1-METHYL-1H-IMIDAZOLE-5-CARBOXALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMO-1-METHYL-1H-IMIDAZOLE-5-CARBOXALDEHYDE(141524-74-5)
• EPA Substance Registry System: 4-BROMO-1-METHYL-1H-IMIDAZOLE-5-CARBOXALDEHYDE(141524-74-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 141524-74-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 59, p. 5524, 1994 DOI: 10.1021/jo00098a006

InChI:InChI=1/C5H5BrN2O/c1-8-3-7-5(6)4(8)2-9/h2-3H,1H3

Upstream product

• 68-12-2 N,N-dimethyl-formamide 
• 158585-80-9 1-Methyl-4,5-dibromoimidazole-2-carboxylic acid 
• 143122-18-3 5-hydroxymethyl-2-mercapto-1-methyl-1H-imidazole 
• 38993-84-9 (1-methyl-1H-imidazol-5-yl)methanol 
• 1003-91-4 N-methyl-2,4,5-tribromoimidazole 
• 74-88-4 methyl iodide 
• 141524-73-4 1-methyl-4-bromo-5-hydroxymethyl-1H-imidazole 

Downstream Products

• 141524-62-1 4-<<(4-methoxyphenyl)methyl>thio>-1-methyl-1H-imidazole-5-carbaldehyde 
• 39021-62-0 1-methylimidazole-5-carbaldehyde 
• 158585-82-1 1-methyl-4-phenyl-1H-imidazole-5-carbaldehyde 
• 213692-64-9 (5R,10aR)-9-<(5-formyl-1-methyl-1H-imidazol-4-yl)thio>-6,8-dimethoxy-5-<(4-methoxyphenyl)methyl>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one 
• 221333-22-8 (5S,10aS)-6,8-dimethoxy-9-<(5-formyl-1-methyl-1H-imidazol-4-yl)thio>-5-<(4-methoxyphenyl)methyl>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one 
• 1126369-59-2 N-(5-(5-formyl-1-methyl-1H-imidazol-4-yl)-2-methylphenyl)-4-(pyridin-2-ylmethoxy)benzamide 
• 1126367-52-9 2,4-dimethyl-5-(1-methyl-1H-imidazol-4-yl)aniline 
• 1258282-96-0 5-benzenesulfonyl-3-methyl-3H-imidazole-4-carbaldehyde 
• 368-16-1 3-methyl-L-histidine 
• 141610-84-6 (2R-cis)-2,5-dihydro-3,6-dimethoxy-2-(1-methylethyl)-5-<<1-methyl-4-(phenylthio)-1H-imidazol-5-yl>methyl>pyrazine 
• 141524-78-9 (2R-trans)-2,5-dihydro-3,6-dimethoxy-2-(1-methylethyl)-5-<<1-methyl-4-(phenylthio)-1H-imidazol-5-yl>methyl>pyrazine 
• 141524-79-0 3-methyl-5-(phenylthio)-L-histidine methyl ester 
• 141524-71-2 3-methyl-5-(phenylthio)-L-histidine 
• 141524-76-7 1-methyl-4-(phenylthio)-1H-imidazole-5-methanol 

Relevant articles and documents

4,5-Disubstituted N-Methylimidazoles as Versatile Building Blocks for Defined Side-Chain Introduction

Fungerin is a 1,4,5-trisubstituted imidazole natural product characterised by a broad spectrum of antifungal activities. We planned to develop flexible strategies to access to such compounds. Imidazoles bearing suitable anchor groups at C-4 and C-5 allow the introduction of various substituted side-chains, generating libraries of fungerin derivatives for biological tests. Starting from commercially available reactants, two N-methyl 4,5-substituted imidazole core units were synthesised. Derivatives of type 1 contained two orthogonally protected C-1 anchors. Selective side-chain introduction was achieved through a sequence of Grignard coupling at C-5 to replace a tosylate and a Horner olefination through an aldehyde attached to C-4. Two target fungerin derivatives were synthesised. Since the organometallic substitution of the C-5-CH2-positioned leaving group proved to suffer from limitations concerning potential competing side-reactions, a type 2 imidazole core was built up. These structures had a halogen centre at C-4 and a hydroxyethyl anchor at C-5. Now, selective side-chain introduction allowed us to use Julia olefination to form the allyl side-chain at C-5 and Heck reactions to introduce the C-4 acryl substituents. Eight derivatives, including fungerin, were synthesised by this latter strategy, without producing any regioisomers. The second approach had the advantage that various side-chains could be coupled at C-4 and C-5 in two final steps. Thus, this strategy represents a versatile way to build up libraries of fungerin derivatives for biological testing.

MATRIX METALLOPROTEINASE (MMP) INHIBITORS AND METHODS OF USE THEREOF

Hydantoin based compounds useful as inhibitors of matrix metalloproteinases (MMPs), particularly macrophage elastase (MMP-12) are described. Also described are related compositions and methods of using the compounds to inhibit MMP-12 and treat diseases mediated by MMP-12, such as asthma, chronic obstructive pulmonary disease (COPD), emphysema, acute lung injury, idiopathic pulmonary fibrosis (IPF), sarcoidosis, systemic sclerosis, liver fibrosis, nonalcoholic steatohepatitis (NASH), arthritis, cancer, heart disease, inflammatory bowel disease (IBD), acute kidney injury (AKI), chronic kidney disease (CKD), Alport syndrome, and nephritis.

HEMOGLOBIN MODIFIER COMPOUNDS AND USES THEREOF

Described herein are compounds, including pharmaceutically acceptable salts thereof, methods of making such compounds, pharmaceutical compositions comprising such compounds, and methods of using such compounds to treat, prevent or diagnose blood-based diseases, disorders or conditions.

Carboxylate protection for the synthesis of 4,5-disubstituted 1-methylimidazoles

Using the carboxylate function as a readily removed blocking group for the 2-position, a regioselective synthesis of diverse 4,5-disubstituted 1-methylimidazoles has been developed starting from 1-methyltribromoimidazole, 5.

Preparatory study for the synthesis of the starfish alkaloid imbricatine. Syntheses of 5-arylthio-3-methyl-L-histidines

Chiral syntheses of 3-methyl-5-(phenylthio)-L-histidine (8a) and 3-methyl-5-(1-naphthalenylthio)-L-histidine (8b), selected as models for the asteroid alkaloid imbricatine (7), have been accomplished through a 10-step route starting from 4(5)-bromoimidazole (9). The key steps involved were methylation of 9, hydroxymethylation of 4-bromo-1-methyl-1H-imidazole (11), replacement of the 4-bromo group by an arylthio group in the aldehyde 14, and introduction of a chiral α-amino acid moiety into the chlorides 17a and 17b by the 'bis-lactim ether' method. The synthesis of the 4-(4-methoxybenzyl)thio analogue 17c, carried out in a similar manner, concluded formal syntheses of ovothiols A and C (1 and 3).

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.