1124-14-7

Usage

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

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

Downstream Products

• 71236-50-5 4-Cyclopropylphenyltrimethylsilan 
• 26979-28-2 p-Cyclopropylphenyldiphenylmethanol 
• 130820-13-2 1-(4-cyclopropylphenyl)-1-phenyl-3-(1-piperidinyl)propanol 
• 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 
• 109088-45-1 1-Cyclopropyl-4-(2,2-dimethyl-3-methylene-cyclopropyl)-benzene 
• 109088-59-7 1-Cyclopropyl-4-diazomethyl-benzene 
• 109088-68-8 (4-Cyclopropyl-phenyl)-diazo-acetic acid ethyl ester 
• 109122-72-7 1-(4-Cyclopropyl-phenyl)-2,2-dimethyl-3-methylene-cyclopropanecarboxylic acid ethyl ester 
• 109088-61-1 <(triisopropylphenyl)sulfonyl>hydrazone of p-cyclopropylbenzaldehyde 
• 863032-11-5 4-(4-cyclopropylphenyl)but-3-yn-1-ol 
• 109088-62-2 C₉H₉Li 

Relevant academic research and scientific papers

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.

Oxidative esterification of primary alcohols at room temperature under aqueous medium

Oxidative esterification of aliphatic primary alcohols with bromide and bromate couple in aqueous acidic medium at room temperature is reported with a wide range of substrate scope for both aliphatic and cyclic alcohols and obtained excellent yields of products.

Aminofluorination of Cyclopropanes: A Multifold Approach through a Common, Catalytically Generated Intermediate

We have discovered a highly regioselective aminofluorination of cyclopropanes. Remarkably, four unique sets of conditions-two photochemical, two purely chemical-generated the same aminofluorinated adducts in good to excellent yields. The multiple, diverse ways in which the reaction could be initiated provided valuable clues that led to the proposal of a "unifying" chain propagation mechanism beyond initiation, tied by a common intermediate. In all, the proposed mechanism herein is substantiated by product distribution studies, kinetic analyses, LFERs, Rehm-Weller estimations of ΔGET, competition experiments, KIEs, fluorescence data, and DFT calculations. From a more physical standpoint, transient-absorption experiments have allowed direct spectroscopic observation of radical ion intermediates (previously only postulated or probed indirectly in photochemical fluorination systems) and, consequently, have provided kinetic support for chain propagation. Lastly, calculations suggest that solvent may play an important role in the cyclopropane ring-opening step.

Synergistic effect of additives on cyclopropanation of olefins

An efficient cyclopropanation of olefins with Zn(CH2I) 2, a catalytic amount of CCl3CO2H, and 1,2-dimethoxyethane at room temperature is described. A wide variety of olefins, including acid-sensitive substrates,

An efficient synthesis of 3-substituted N-glycoside indoles useful as sodium-dependent glucose transporter inhibitors

A practical synthesis of two N-glycoside indoles 1 and 2, identified as highly potent sodium-dependent glucose transporter (SGLT) inhibitors is described. Highlights of the synthetic process include a selective and quantitative Vilsmeier acylation and a h

PROCESS FOR THE PREPARATION OF COMPOUNDS USEFUL AS INHIBITORS OF SGLT-2

The present invention is directed to a novel process for the preparation of compounds having inhibitory activity against sodium-dependent glucose transporter (SGLT) being present in the intestine or kidney.

2-PYRIDONE COMPOUNDS

A 2-pyridone compound represented by the formula [1]: {wherein in the formula [1], the ring represented by A represents a benzene ring or a pyridine ring, X represents any of the structures represented by the formulas [3] shown below: V represents a single bond or a lower alkylene group, and W represents a single bond, an ether bond or a lower alkylene group (wherein the lower alkylene group may contain an ether bond)}, a tautomer or stereoisomer of the compound, a pharmaceutically acceptable salt thereof, or a solvate thereof is a compound that has an excellent GK activating effect and is useful as a pharmaceutical.

Phenyl bridging in ring-substituted cumyloxyl radicals. a product and time-resolved kinetic study

The reactivity of cumyloxyl radicals bearing cyclopropyl and 2,2-diphenylcyclopropyl groups in the para position has been investigated. Depending on radical structure, products deriving from C-C β-scission and/or cyclopropyl ring-opening are observed, sup