59469-74-8

Basic information

• Product Name: 8-Chloro-6-(2-fluorophenyl)-1-methyl-6H-Imidazo[1,5-a][1,4]benzodiazepine
• Synonyms: 8-Chloro-6-(2-fluorophenyl)-1-methyl-6H-Imidazo[1,5-a][1,4]benzodiazepine
• CAS NO: 59469-74-8
• Molecular Formula: C18H13ClFN3
• Molecular Weight: 325.773
• Mol File: 59469-74-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 180-181 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• Boiling Point: 472.2±55.0 °C(Predicted)
• Density: 1.35±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 8-Chloro-6-(2-fluorophenyl)-1-methyl-6H-Imidazo[1,5-a][1,4]benzodiazepine(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Chloro-6-(2-fluorophenyl)-1-methyl-6H-Imidazo[1,5-a][1,4]benzodiazepine(59469-74-8)
• EPA Substance Registry System: 8-Chloro-6-(2-fluorophenyl)-1-methyl-6H-Imidazo[1,5-a][1,4]benzodiazepine(59469-74-8)

Safety Data

• Hazardous Substances Data: 59469-74-8(Hazardous Substances Data)

Usage

Description

8-Chloro-6-(2-fluorophenyl)-1-methyl-6H-Imidazo[1,5-a][1,4]benzodiazepine is a chemical compound belonging to the imidazobenzodiazepine class. It is an isomer of Midazolam, a well-known anesthetic, anticonvulsant, sedative, and hypnotic agent. 8-Chloro-6-(2-fluorophenyl)-1-methyl-6H-Imidazo[1,5-a][1,4]benzodiazepine is characterized by its unique molecular structure, which includes a chlorine atom at the 8th position, a 2-fluorophenyl group at the 6th position, and a methyl group at the 1st position.

Uses

Used in Pharmaceutical Industry:
8-Chloro-6-(2-fluorophenyl)-1-methyl-6H-Imidazo[1,5-a][1,4]benzodiazepine is used as an active pharmaceutical ingredient for its anesthetic, anticonvulsant, sedative, and hypnotic properties. Its chemical structure and isomerism with Midazolam suggest potential applications in the development of new drugs with improved efficacy, reduced side effects, or novel therapeutic indications.
Used in Research and Development:
In the field of medicinal chemistry and pharmaceutical research, this compound serves as a valuable research tool for understanding the structure-activity relationships of imidazobenzodiazepines. It can be used to investigate the effects of structural modifications on the pharmacological properties of Midazolam and its analogs, potentially leading to the discovery of new drugs with enhanced therapeutic profiles.
Used in Drug Formulation and Delivery:
8-Chloro-6-(2-fluorophenyl)-1-methyl-6H-Imidazo[1,5-a][1,4]benzodiazepine may also be utilized in the development of novel drug formulations and delivery systems. Its unique chemical properties could be exploited to improve the bioavailability, stability, or targeted delivery of the compound, potentially enhancing its therapeutic effects and reducing side effects.

Upstream product

• 59467-70-8 Midazolam 
• 59468-44-9 8-Chloro-6-(2-fluorophenyl)-1-methyl-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid 

Downstream Products

• 59468-72-3 5-chloro-2'-fluoro-2-(5-hydroxymethyl-2-methyl-imidazol-1-yl)-benzophenone 
• 64740-65-4 8-chloro-6-(2-fluoro-phenyl)-1-methyl-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-4-carboxylic acid methyl ester 
• 59469-38-4 2-Chloro-13a-(2-fluorophenyl)-12,13a-dihydro-6-methyl-9H,11H-imidazo[1,5-a]oxazolo[3,2-d][1,4]benzodiazepine 
• 59468-92-7 3-bromo-8-chloro-6-(2-fluoro-phenyl)-1-methyl-4H-benzo[f]imidazo[1,5-a][1,4]diazepine 
• 59469-01-1 8-chloro-6-(2-fluoro-phenyl)-1-methyl-5-(toluene-4-sulfonyl)-5,6-dihydro-4H-benzo[f]imidazo[1,5-a][1,4]diazepine 
• 59469-06-6 5-acetyl-8-chloro-6-(2-fluoro-phenyl)-1-methyl-5,6-dihydro-4H-benzo[f]imidazo[1,5-a][1,4]diazepine 
• 59469-02-2 8-chloro-6-(2-fluoro-phenyl)-1-methyl-5-nitroso-5,6-dihydro-4H-benzo[f]imidazo[1,5-a][1,4]diazepine 
• 59469-05-5 5-allyl-8-chloro-6-(2-fluoro-phenyl)-1-methyl-5,6-dihydro-4H-benzo[f]imidazo[1,5-a][1,4]diazepine 
• 59469-04-4 8-chloro-6-(2-fluoro-phenyl)-1,5-dimethyl-5,6-dihydro-4H-benzo[f]imidazo[1,5-a][1,4]diazepine 
• 59468-07-4 8-chloro-6-(2-fluorophenyl)-5,6-dihydro-1-methyl-6H-imidazo<1,5-a><1,4>benzodiazepine 
• 59468-73-4 5-aminomethyl-1-[4-chloro-2-(2-fluorobenzoyl)phenyl]-2-methyl-imidazole dihydrochloride 
• 59467-70-8 Midazolam 
• 145175-81-1 C₁₈H₁₄⁽²⁾HClFN₃ 
• 145175-80-0 1,3-bis-<8-chloro-6-(2-fluorophenyl)-5,6-dihydro-1-methyl-4H-imidazo<1,5-a><1,4>benzodiazepin-4-yl>-2-propanone 

Relevant articles and documents

PROCESS FOR THE SYNTHESIS OF 4H-IMIDAZO [1,5-a] [1,4] BENZODIAZEPINES, IN PARTICULAR MIDAZOLAM AND SALTS THEREOF

The present invention refers to a process for the preparation of 4H-imidazo[1,5-a][1,4]benzodiazepines, in particular Midazolam, through an efficient and selective decarboxylation reaction of the derivative compound of the 5-aminomethyl-1-phenyl-1H-imidazole-4-carboxylic acid of formula (II) avoiding the formation of the 6H-imidazo[1,5-a][1,4]benzodiazepines by-products and the ensuing process for the isomerisation of a 4H-imidazo[1,5-a][1,4]benzodiazepine product.

Imidazodiazepines and processes therefor

Novel Imidazobenzodiazepines and their analogs are useful as anticonvulsants, muscle relaxant, anxiolytic and sedative agents. Preferred compounds of this class belong to the imidazo[1,5-a][1,4]diazepine series which may have a very wide variety of organic substituents. An especially preferred genus included within the purview of the invention encompasses a compound of the formula STR1 wherein R1 is hydrogen and lower alkyl preferably methyl; R3 and R5 are hydrogen; R4 is hydrogen, nitro and halogen, most preferably, chlorine, and in a most preferred embodiment when positioned on the fused benzo portion of the imidazobenzodiazepine is in the 8-position thereof, R6 is phenyl or halo, nitro, or lower alkyl-substituted phenyl, preferably, halo, with fluorine being the preferred halogen, the substituted fluoro being positioned in the 2-position of the phenyl moiety and R2 is hydrogen and lower alkyl.