1124-14-7

Basic information

• Product Name: 1-Bromo-4-cyclopropylbenzene
• Synonyms: 4-BROMOCYCLOPROPYLBENZENE;(4-Bromophenyl)cyclopropane;(p-Bromophenyl)cyclopropane;1-Bromo-4-cyclopropylbenzene;4-Cyclopropylbromobenzene;4-Cyclopropylphenyl bromide;Benzene, 1-broMo-4-cyclopropyl-
• CAS NO: 1124-14-7
• Molecular Formula: C₉H₉Br
• Molecular Weight: 197.07
• Mol File: 1124-14-7.mol
• Article Data: 19

Chemical Properties

• Melting Point: 15 °C
• Boiling Point: 231 °C
• Flash Point: 96 °C
• Appearance: /
• Density: 1.474
• Vapor Pressure: 0.096mmHg at 25°C
• Refractive Index: 1.604
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-Bromo-4-cyclopropylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Bromo-4-cyclopropylbenzene(1124-14-7)
• EPA Substance Registry System: 1-Bromo-4-cyclopropylbenzene(1124-14-7)

Safety Data

• Hazardous Substances Data: 1124-14-7(Hazardous Substances Data)

Usage

Description

1-Bromo-4-cyclopropylbenzene is an organic compound characterized by the presence of a bromine atom attached to a benzene ring, with a cyclopropyl group at the 4-position. This chemical structure endows it with unique properties that make it a valuable intermediate in the synthesis of various pharmaceutical compounds.

Uses

Used in Pharmaceutical Industry:
1-Bromo-4-cyclopropylbenzene is used as a key reagent for the synthesis of sodium-dependent glucose transporter inhibitors. These inhibitors play a crucial role in managing blood glucose levels, making them essential in the development of treatments for diabetes and other metabolic disorders.
Additionally, 1-Bromo-4-cyclopropylbenzene is utilized in the synthesis of Tofoglifozin, a novel selective sodium-glucose cotransporter 2 (SGLT2) inhibitor. SGLT2 inhibitors are a class of drugs that work by blocking the reabsorption of glucose in the kidneys, thereby reducing blood glucose levels. Tofoglifozin, in particular, has shown promise as a potential treatment for type 2 diabetes, offering a new therapeutic option for patients with this condition.

InChI:InChI=1/C9H9Br/c10-9-5-3-8(4-6-9)7-1-2-7/h3-7H,1-2H2

Upstream product

• 1128-70-7 3-(4-bromo-phenyl)-4,5-dihydro-1H-pyrazole 
• 73387-46-9 3-(4-bromophenyl)-1H-pyrazole 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 75-11-6 diiodomethane 
• 873-49-4 cyclopropylbenzene 
• 122-97-4 3-Phenyl-1-propanol 
• 14399-53-2 bis(iodomethyl)zinc 
• 593-71-5 Chloroiodomethane 
• 6921-44-4 4-nitrophenylcyclopropane 
• 3158-71-2 4-cyclopropylaniline 
• 19434-65-2 3-chloropropanaldehyde 
• 18620-02-5 (4-bromophenyl)magnesium bromide 

Downstream Products

• 130820-10-9 1-benzyl-4-(4-cyclopropylphenyl)piperidine-4-ol 
• 90712-56-4 5-(4-Bromophenyl)-4,5-dihydroisoxazole 
• 20034-50-8 4-cyclopropylbenzaldehyde 
• 134920-37-9 N-[1-(4-bromophenyl)propyl]acetamide 
• 34733-62-5 1-Methoxy-3-brom-1-p-bromphenylpropan 
• 49678-04-8 trans-4-bromocinnamaldehyde 
• 27549-93-5 (E)-3-(4-bromophenyl)acrylonitrile 
• 36372-60-8 2-propionyl-5-bromonitrosobenzene 
• 36372-62-0 1-(2-amino-4-bromophenyl)propan-1-one 
• 27546-47-0 <2,4-Dimethyl-phenyl>-cyclopropan 
• 77446-30-1 <2,4,6-Trimethyl-phenyl>-cyclopropan 
• 90841-16-0 (2-Brom-4-methyl-phenyl)-cyclopropan 
• 92846-05-4 <5-Brom-2,4-dimethyl-phenyl>-cyclopropan 
• 863032-11-5 4-(4-cyclopropylphenyl)but-3-yn-1-ol 

Relevant articles and documents

Silylium-Ion-Promoted Ring-Opening Hydrosilylation and Disilylation of Unactivated Cyclopropanes

A silylium-ion-promoted ring-opening hydrosilylation of unactivated cyclopropanes is reported. The reaction is facilitated by the γ-silicon effect, and the regioselectivity is influenced by various stabilizing effects on the carbenium-ion intermediates, including the β-silicon effect. The experimental observations are in accord with the computed reaction mechanism. The work also showcases the ability of silylium ions to isomerize cyclopropyl to allyl groups, and the resulting α-olefins engage in a silylium-ion-mediated disilylation with hexamethyldisilane.

Intermolecular Electrophilic Bromoesterification and Bromoetherification of Unactivated Cyclopropanes

1,3-difunctionalization of cyclopropane is an useful organic transformation. The corresponding 1,3-difunctionalized products are synthetic synthons and building blocks in many organic syntheses. Many existing ring-opening difunctionalization methodologies rely primarily on the use of donor?acceptor cyclopropanes, while the difunctionalization of unactivated cyclopropanes is less exploited. In this research, 1,3-bromoesterification and 1,3-bromoetherification of unactivated cyclopropanes were successfully achieved using N-bromosuccinimide as the brominating agent with high yields and regioselectivity. (Figure presented.).

Lewis Base-Promoted Ring-Opening 1,3-Dioxygenation of Unactivated Cyclopropanes Using a Hypervalent Iodine Reagent

A facile and effective system has been developed for the regio- and chemoselective ring-opening/electrophilic functionalization of cyclopropanes through C?C bond activation by [bis(trifluoroacetoxy)iodo]benzene with the aid of the Lewis basic promoter p-toluenesulfonamide. The p-toluenesulfonamide-promoted system works well for a wide range of cyclopropanes, resulting in the formation of 1,3-diol products in good yields and regioselectivity.