158365-99-2

Basic information

• Product Name: 2-BUTYL-5-CHLORO-1H-IMIDAZOLE
• Synonyms: 2-BUTYL-5-CHLORO-1H-IMIDAZOLE;2-n-Butyl-5-chloro-1H-iMidazole
• CAS NO: 158365-99-2
• Molecular Formula: C₇H₁₁ClN₂
• Molecular Weight: 158.63
• Product Categories: Imidazoles & Benzimidazoles;Halides;Imidazoles & Benzimidazoles;Heterocycles
• Mol File: 158365-99-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 86-88°C
• Boiling Point: 317.014°C at 760 mmHg
• Flash Point: 174.89°C
• Appearance: /
• Density: 1.143g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.524
• Storage Temp.: Refrigerator
• CAS DataBase Reference: 2-BUTYL-5-CHLORO-1H-IMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BUTYL-5-CHLORO-1H-IMIDAZOLE(158365-99-2)
• EPA Substance Registry System: 2-BUTYL-5-CHLORO-1H-IMIDAZOLE(158365-99-2)

Safety Data

• Hazardous Substances Data: 158365-99-2(Hazardous Substances Data)

Usage

Chemical Properties

Brown SolidLight Brown Solid

Synthesis Reference(s)

The Journal of Organic Chemistry, 64, p. 8084, 1999 DOI: 10.1021/jo9824910

InChI:InChI=1/C7H11ClN2/c1-2-3-4-7-9-5-6(8)10-7/h5H,2-4H2,1H3,(H,9,10)

Upstream product

• 999-09-7 ethyl valerimidate 
• 109-51-3 pentanimidamide 
• 57246-71-6 methyl pentanimidate 
• 110-59-8 pentanonitrile 
• 36801-39-5 N-(cyanomethyl)pentanamide 
• 154147-42-9 2-butyl-2-imidazolin-5-one 

Downstream Products

• 83857-96-9 2-n-butyl-5-Chloroimidazole-4-Carbaldehyde 
• 83857-96-9 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde 

Relevant articles and documents

Novel Syntheses of 2-Butyl-5-chloro-3H-imidazole-4-carbaldehyde: A Key Intermediate for the Synthesis of the Angiotensin II Antagonist Losartan

Reaction of glycine methyl ester (19) with imidate 18 under carefully optimized conditions allowed preparation of the rather unstable imidazolinone 11 in ca. 90% yield. Reaction of 11 with POCl3/ DMF followed by aqueous workup gave aldehyde 2, a key intermediate for the synthesis of the angiotensin II antagonist Losartan, in ca. 55% yield. Structural identification of intermediates and byproducts formed during both the reaction to prepare 11 and the reaction of 11 with POCl3/DMF allowed development of several closely related syntheses of aldehyde 2.

Process for preparing 2,4,5-trisubstituted imidazoles from N-acylated alpha-amino nitriles

The invention is a process for preparing an imidazole of formula I which comprises treating an N-acylated α-amino nitrile with a phosphine and a carbon tetrahalide of the formula CX4, wherein X is Cl or Br, to form a haloimidazole of the formula wherein R1 is selected from the group consisting of hydrogen, C1-6alkyl, —CH2-aryl, and aryl; and R2 is selected from the group consisting of hydrogen, C1-6alkyl, —CH2—O-aryl and aryl; and X is selected from the group consisting of Cl and Br.