40648-23-5

Basic information

• Product Name: 6-bromo-1-methylcyclohexene
• CAS NO: 40648-23-5
• Molecular Formula: C₇H₁₁Br
• Molecular Weight: 175.0662
• Mol File: 40648-23-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 166.7°C at 760 mmHg
• Flash Point: 60.7°C
• Density: 1.325g/cm³
• Vapor Pressure: 2.32mmHg at 25°C
• Refractive Index: 1.513
• CAS DataBase Reference: 6-bromo-1-methylcyclohexene(CAS DataBase Reference)
• NIST Chemistry Reference: 6-bromo-1-methylcyclohexene(40648-23-5)
• EPA Substance Registry System: 6-bromo-1-methylcyclohexene(40648-23-5)

Safety Data

• Hazardous Substances Data: 40648-23-5(Hazardous Substances Data)

Usage

General Description

6-bromo-1-methylcyclohexene is a chemical compound that consists of a six-membered carbon ring with a bromine atom attached at the 6th position and a methyl group attached at the 1st position. It is classified as a cycloalkene, meaning it contains a double bond within the ring structure. 6-bromo-1-methylcyclohexene is commonly used in organic synthesis and as a building block for the production of other chemicals. It is also known to undergo various reactions such as addition, substitution, and elimination, making it a versatile intermediate in chemical processes. Additionally, 6-bromo-1-methylcyclohexene is known to be a flammable liquid with low solubility in water, and caution should be exercised when handling and storing this compound.

Upstream product

• 591-49-1 1-methylcyclohex-1-ene 
• 73446-71-6 2-bromo-1-hydroxy-1-methylcyclohexane 
• 20461-30-7 2-methylcyclohex-2-en-1-ol 

Downstream Products

• 53097-22-6 dimethyl-(2-methyl-cyclohex-2-enyl)-amine 
• 1121-18-2 2-methyl-2-cyclohexen-1-one 
• 148874-05-9 2-But-3-ynyl-2-(2-methyl-cyclohex-2-enyl)-benzo[1,3]dithiole 1,1,3,3-tetraoxide 
• 1182228-57-4 (-)-(S)-(2-(2-methylcyclohex-2-enyl)ethyl)benzene 
• 1241733-41-4 C₁₅H₂₀O 
• 51552-22-8 2-methylcyclohex-2-enamine 
• 83529-02-6 N-(2-methylcyclohex-2-en-1-yl)acetamide 

Relevant articles and documents

Guanidine–Copper Complex Catalyzed Allylic Borylation for the Enantioconvergent Synthesis of Tertiary Cyclic Allylboronates

An enantioconvergent synthesis of chiral cyclic allylboronates from racemic allylic bromides was achieved by using a guanidine–copper catalyst. The allylboronates were obtained with high γ/α regioselectivities (up to 99:1) and enantioselectivities (up to 99 % ee), and could be further transformed into diverse functionalized allylic compounds without erosion of optical purity. Experimental and DFT mechanistic studies support an SN2′ borylation process catalyzed by a monodentate guanidine–copper(I) complex that proceeds through a special direct enantioconvergent transformation mechanism.

(Guanidine)copper Complex-Catalyzed Enantioselective Dynamic Kinetic Allylic Alkynylation under Biphasic Condition

Highly enantioselective allylic alkynylation of racemic bromides under biphasic condition is furnished in this report. This approach employs functionalized terminal alkynes as pro-nucleophiles and provides 6- and 7-membered cyclic 1,4-enynes with high yields and excellent enantioselectivities (up to 96% ee) under mild conditions. Enantioretentive derivatizations highlight the synthetic utility of this transformation. Cold-spray ionization mass spectrometry (CSI-MS) and X-ray crystallography were used to identify some catalytic intermediates, which include guanidinium cuprate ion pairs and a copper-alkynide complex. A linear correlation between the enantiopurity of the catalyst and reaction product indicates the presence of a copper complex bearing a single guanidine ligand at the enantio-determining step. Further experimental and computational studies supported that the alkynylation of allylic bromide underwent an anti-SN2′ pathway catalyzed by nucleophilic cuprate species. Moreover, metal-assisted racemization of allylic bromide allowed the reaction to proceed in a dynamic kinetic fashion to afford the major enantiomer in high yield.

Copper-catalyzed asymmetric allylic alkylation of racemic cyclic substrates: Application of dynamic kinetic asymmetric transformation (DYKAT)

The copper-catalyzed asymmetric allylic alkylation (AAA) is of great interest in organic synthesis. This reaction was extensively studied using a broad range of substrates, ligands and organometallic reagents. However, the use of racemic substrates was still limited. Although some processes of kinetic resolution are reported in the literature, no examples of quantitative deracemization are described as is the case for the Pd-catalyzed allylic alkylation. We present here a full account of our investigations through the development of the first example of such a process in copper-catalyzed AAA. High enantioselectivities (up to 99% ee), scope of the reaction and mechanistic considerations are reported herein.