6294-39-9

Usage

Uses

Used in Organic Synthesis:
1-bromo-2-methylcyclohexane is used as a reagent in organic synthesis for its ability to participate in various chemical reactions, contributing to the formation of a wide range of organic compounds.
Used in Chemical Production:
1-bromo-2-methylcyclohexane is used as a starting material for the production of other chemicals, highlighting its versatility in the chemical industry.
Used in Pharmaceutical Preparation:
1-bromo-2-methylcyclohexane is used in the preparation of pharmaceuticals, serving as a key intermediate in the synthesis of various medicinal compounds.
Used in Agrochemical Preparation:
1-bromo-2-methylcyclohexane is also used in the preparation of agrochemicals, playing a role in the development of substances for agricultural applications.
Safety Precautions:
It is important to handle 1-bromo-2-methylcyclohexane with care due to its flammable nature and potential to cause irritation to the skin, eyes, and respiratory system upon exposure. Proper safety measures should be followed when working with 1-bromo-2-methylcyclohexane.

InChI:InChI=1/C12H14N4OS/c1-8(17)13-10-6-4-9(5-7-10)11-14-15-12(18-3)16(11)2/h4-7H,1-3H3,(H,13,17)

Upstream product

• 286-08-8 bicyclo[4.1.0]heptane 
• 591-49-1 1-methylcyclohex-1-ene 
• 75-62-7 Bromotrichloromethane 
• 583-59-5 2-Methylcyclohexanol 

Downstream Products

• 189238-63-9 N-phenyl-2-methylcyclohexylamine 
• 82976-59-8 Ethyl α-cyano-2-methylcyclohexaneacetate 
• 583-60-8 2-Methylcyclohexanone 
• 1087768-55-5 2-Phenoxy-1-methyl-cyclohexan 

Relevant academic research and scientific papers

Formation of three-membered rings by SHi displacement. Reverse of cyclopropyl ring opening

The general methods, photoinitiated or peroxide-initiated free radical chain additions of halomethanes to olefins, yield 1,2-addition products at temperatures ranging from 20 to 100°C. At lower temperatures, -42 to -104°C, a competitive reaction, subsequent to the addition of CCl2X., yields alkylcyclopropanes. The reactions of 1-octene or 1-hexene and 1-methylcyclohexene with atomic hydrogen carried out in the presence of several transfer agents (CCl4, CCl3Br, CCl2Br2) initiate a radical chain addition of CCl2X. and yield cyclized materials resulting from the SHi displacement of halogen by a carbon-centered radical. The radical displacement of a halogen on carbon, the reverse of homolytic displacement on cyclopropyl carbon, is dominant at low temperatures. The rate constants for cyclization (kc) vs transfer with halomethane (kt) showed isokinetic temperatures of -46°C (CCl4, 1-hexene); -35°C (CCl4, 1-methylcyclohexene). The isokinetic temperatures for the reactions of the two substrates carried out in the presence of BrCCl3 were calculated as -204 °C (1-octene) and -109°C (1-methylcyclohexene).

Homolytic Ring Fission reactions of Bicycloalkanes and Bicycloalk-2-yl Radicals: Electron Spin Resonance Study of Cycloalkenylmethyl Radicals

Hydrogen abstraction from bicycloalkanes (n=3-6) by t-butoxyl radicals was examined by an e.s.r. technique.The main site of attack was C(2) giving bicycloalk-2-yl radicals which rearranged by β-scission of the outer cyclopropane bonds to give cycloalkenylmethyl radicals.This is in contrast to the bicycloalk-2-yl radicals (n=1,2) which rearranged by fission of the inter-ring bonds to give cycloalkenyl radicals. β-Scission in bicycloalk-2-yl radicals was examined by semi-empirical SCF MO calculations.The conformations and barriers to internal rotation of the cycloalkenylmethyl radicals were determined from the variation in the β-H hyperfine splitting constants with temperature.Photobromination of bicycloalkanes (n=3,4) was also investigated in CCl4 solution.The main process was bimolecular homolytic substitution (SH2) by bromine atoms at the cyclopropane carbons, but there was an increase in hydrogen abstraction with ring size.The SH2 reactions parallel the β-scission reactions of the bicycloalk-2-yl radicals in that the main bond undergoing fission changes from the inter-ring bond to the outer cyclopropane bond as the ring size increases.