70289-39-3

Basic information

• Product Name: (4-BROMOPHENYL)(CYCLOPROPYL)METHANOL
• Synonyms: (4-BROMOPHENYL)(CYCLOPROPYL)METHANOL;p-bromo-alpha-cyclopropylbenzyl alcohol;4-Bromo-α-cyclopropylbenzenemethanol;4-BROMOPHENYL CYCLOPROPYL CARBINOL
• CAS NO: 70289-39-3
• Molecular Formula: C₁₀H₁₁BrO
• Molecular Weight: 227.1
• EINECS: 274-546-5
• Mol File: 70289-39-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 57 °C
• Boiling Point: 321.4°C at 760 mmHg
• Flash Point: 148.2°C
• Appearance: /
• Density: 1.555g/cm³
• Vapor Pressure: 0.000123mmHg at 25°C
• Refractive Index: 1.634
• CAS DataBase Reference: (4-BROMOPHENYL)(CYCLOPROPYL)METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (4-BROMOPHENYL)(CYCLOPROPYL)METHANOL(70289-39-3)
• EPA Substance Registry System: (4-BROMOPHENYL)(CYCLOPROPYL)METHANOL(70289-39-3)

Safety Data

• Hazardous Substances Data: 70289-39-3(Hazardous Substances Data)

Usage

Description

(4-BROMOPHENYL)(CYCLOPROPYL)METHANOL, also known as bromo(cyclopropyl)benzyl alcohol, is a chemical compound with the molecular formula C10H11BrO. It is a white to off-white solid that is often used in organic synthesis as a building block for various pharmaceuticals and agrochemicals. (4-BROMOPHENYL)(CYCLOPROPYL)METHANOL is known for its ability to act as a versatile precursor for the synthesis of a variety of bioactive compounds, due to the presence of the cyclopropyl and benzyl alcohol functional groups. Its unique structure and reactivity make it a valuable tool in the field of organic chemistry.

Uses

Used in Pharmaceutical Industry:
(4-BROMOPHENYL)(CYCLOPROPYL)METHANOL is used as a building block for the synthesis of various medicines. Its cyclopropyl and benzyl alcohol functional groups make it a versatile precursor for the development of bioactive compounds with potential therapeutic applications.
Used in Agrochemical Industry:
(4-BROMOPHENYL)(CYCLOPROPYL)METHANOL is used as a starting material in the preparation of agrochemicals. Its unique structure and reactivity allow for the synthesis of compounds with pesticidal or herbicidal properties, contributing to the development of effective crop protection solutions.
Used in Organic Synthesis:
(4-BROMOPHENYL)(CYCLOPROPYL)METHANOL is used as a versatile precursor in the preparation of other chemical compounds. Its cyclopropyl and benzyl alcohol functional groups enable the synthesis of a wide range of organic compounds for various applications, including the development of new materials and the improvement of existing ones.

InChI:InChI=1/C10H11BrO/c11-9-5-3-8(4-6-9)10(12)7-1-2-7/h3-7,10,12H,1-2H2

Upstream product

• 6952-89-2 (4-bromophenyl)(cyclopropyl)methanone 
• 4333-56-6 cyclopropyl bromide 
• 1122-91-4 4-bromo-benzaldehyde 
• 108-86-1 bromobenzene 
• 23719-80-4 cyclopropylmagnesium bromide 
• 106-37-6 1.4-dibromobenzene 
• 1489-69-6 Cyclopropanecarboxaldehyde 
• 589-87-7 1,4-bromoiodobenzene 

Downstream Products

• 179251-28-6 1-Bromo-4-(cyclopropylmethyl)-benzene 
• 1093214-56-2 4-(cyclopropylmethyl)benzoic acid. 

Relevant articles and documents

CHEMICAL COMPOUNDS

The present disclosure describes novel compounds, or their pharmaceutically acceptable salts, pharmaceutical compositions containing them, and their medical uses. The compounds of the disclosure have activity as Janus kinase (JAK) inhibitors and are useful in the treatment or control of inflammation, auto-immune diseases, cancer, and other disorders and indications where modulation of JAK would be desirable. Also described herein are methods of treating inflammation, auto-immune diseases, cancer, and other conditions susceptible to inhibition of JAK by administering a compound herein described.

PYRAZOLE COMPOUNDS AS BTK INHIBITORS

The present invention encompasses compounds of the formula (I) wherein the groups R1, Cy, and Y are defined herein, which are suitable for the treatment of diseases related to BTK, process of making, pharmaceutical preparations which contain compounds and their methods of use.

Mechanistic Evidence regarding the Magnesium Halide Transformation of Cyclopropylmethanols into Homoallylic Halides

Cyclopropylmethanols are converted into homoallylic halides in high yield by treatment with magnesium bromide or iodide in refluxing, anhydrous diethyl ether.For uncovering of the details of the reaction mechanism, (cyclopropylphenylmethoxy)magnesium bromide (3a) was prepared by treatment of cyclopropylphenylmethanol (1) with hydridomagnesium bromide.Alkoyoxymagnesium bromide 3a was stable in refluxing diethyl ether and was not changed when treated with tetrabutylammonium bromide but was transformed into 4-bromo-1-phenyl-1-butene by treatment with hydrogen bromide or magnesium bromide.These results, together with first-order kinetics for the reaction of magnesium halide with 1, suggest a mechanism involving rapid formation of an intermediate ion pair (4), a magnesium oxonium bromide, which undergoes rate-determining ring opening to give homoallylic halide.A Hammett study of the reaction of substituted cyclopropylphenylmethanols with magnesium iodide provides a p value of -1.82, revealing substantial positive charge development on the carbinol carbon in the latter step.This investigation provides one of only a very few reported examples of Hammett studies used to probe positive charge development for a reaction carried out in anhydrous diethyl ether.