17299-10-4

Basic information

• Product Name: 1-(bromomethyl)cyclohexanol
• CAS NO: 17299-10-4
• Molecular Formula: C₇H₁₃BrO
• Molecular Weight: 193.0815
• Mol File: 17299-10-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 243.1°C at 760 mmHg
• Flash Point: 100.8°C
• Density: 1.418g/cm³
• Vapor Pressure: 0.00555mmHg at 25°C
• Refractive Index: 1.523
• CAS DataBase Reference: 1-(bromomethyl)cyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(bromomethyl)cyclohexanol(17299-10-4)
• EPA Substance Registry System: 1-(bromomethyl)cyclohexanol(17299-10-4)

Safety Data

• Hazardous Substances Data: 17299-10-4(Hazardous Substances Data)

Usage

General Description

1-(bromomethyl)cyclohexanol is a chemical compound with the molecular formula C7H13BrO. It is a colorless or pale yellow liquid with a molecular weight of 197.08 g/mol. The compound is primarily used as an intermediate in the production of pharmaceuticals, agrochemicals, and other organic compounds. It is also used in research and development as a starting material for various organic synthesis reactions. 1-(bromomethyl)cyclohexanol is considered to be hazardous, as it is toxic if ingested, inhaled, or absorbed through the skin, and can cause severe eye and skin irritation. It should be handled with appropriate safety precautions in a well-ventilated area and with the use of personal protective equipment.

Upstream product

• 1192-37-6 methylenecyclohexane 
• 108-94-1 cyclohexanone 
• 74-95-3 1,1-dibromomethane 
• 185-70-6 1-oxaspiro(2.5)octane 

Downstream Products

• 88476-49-7 1-(bromomethyl)-1-cyclohexyl chloroformate 
• 88476-36-2 1-(bromomethyl)-1-cyclohexyl phenylcarbamate 

Relevant articles and documents

A new entry of highly selective and nucleophilic BrH2C-and CLH2c-titanium complexes for carbonyl coupling

The direct coupling of various aldehydes and ketones with CH2Br2 or CH2Cl2 promoted by TiCl4-Mg bimetallic complex provides an extremely simple, practical, and efficient approach for the construction of bromomethyl or chloromethyl carbinols. The high chemoselectivity of this chemistry is illus-trated by the TiCl4-Mg-promoted selective coupling of CH2Br2 or CH2Cl2 with an aldehyde in the presence of ketone and selective transfer of CH2Br or CH2Cl to saturated carbonyl moiety. This protocol is also suitable for sterically hindered and enoliza-ble carbonyl compounds.

Et2Zn-mediated rearrangement of bromohydrins

(Chemical Equation Presented) A simple and highly efficient method for the rearrangement of bromohydrins mediated by Et2Zn to synthesize carbonyl compounds was described. Various β-bromo alcohols were treated with 0.6 equiv of Et2Zn to form a zinc complex in CH 2Cl2 at room temperature for 2 h, followed by 1,2-migration to give the corresponding carbonyl compounds. This remarkable and clean rearrangement is general for acyclic and cyclic bromohydrins, and a variety of ring-expansive and -contractive carbonyl compounds were obtained in good to excellent yields according to the feature of the starting bromohydrins. The functional group tolerance of organozinc reagents in this reaction will be useful in organic synthesis. The scope and limitations of this rearrangement process were also investigated.

Regio- and Stereoselective Synthesis of β-Halohydrins from 1,2-Epoxides with Ammonium Halides in the Presence of Metal Salts

A simple efficient, stereoselective, and regioselective method for the synthesis of β-chlorohydrins, β-bromohydrins, and β-iodohydrins by the direct opening of 1,2-epoxides with the corresponding ammonium halide in acetonitrile, in the presence of metal salts, is described.This new method appears to be of general use and competitive with the other methods previously reported.