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

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

Uses

Used in Organic Synthesis:
6-bromo-1-methylcyclohexene is used as a building block for the production of other chemicals due to its ability to undergo addition, substitution, and elimination reactions. Its reactivity and structural features make it a valuable component in the synthesis of complex organic molecules.
Used in Chemical Production:
As a versatile intermediate, 6-bromo-1-methylcyclohexene is utilized in the manufacturing of various chemical products. Its unique structure and reactivity contribute to the development of new compounds and materials with specific properties and applications.
Used in Research and Development:
6-bromo-1-methylcyclohexene serves as a key compound in research and development efforts, particularly in the field of organic chemistry. Its properties and reactions are studied to gain insights into new chemical pathways and to develop innovative synthetic methods.
Used in Pharmaceutical Industry:
6-bromo-1-methylcyclohexene is used as a starting material or intermediate in the synthesis of pharmaceutical compounds. Its unique structure and reactivity enable the creation of novel drug candidates with potential therapeutic applications.
Used in Material Science:
In the field of material science, 6-bromo-1-methylcyclohexene is employed in the development of new materials with specific properties, such as polymers, coatings, and adhesives. Its chemical versatility allows for the design of materials with tailored characteristics for various applications.
Used in Environmental Applications:
6-bromo-1-methylcyclohexene can be used in environmental applications, such as the synthesis of biodegradable polymers or the development of chemical processes that reduce the environmental impact of industrial operations.

Upstream product

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

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 
• 83529-02-6 N-(2-methylcyclohex-2-en-1-yl)acetamide 
• 51552-22-8 2-methylcyclohex-2-enamine 

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.

Discovery of Novel 1-Cyclopentenyl-3-phenylureas as Selective, Brain Penetrant, and Orally Bioavailable CXCR2 Antagonists

CXCR2 has emerged as a therapeutic target for not only peripheral inflammatory diseases but also neurological abnormalities in the central nervous system (CNS). Herein, we describe the discovery of a novel 1-cyclopentenyl-3-phenylurea series as potent and CNS penetrant CXCR2 antagonists. Extensive SAR studies, wherein molecules' property forecast index (PFI) was carefully optimized for overall balanced developability profiles, led to the discovery of the advanced lead compound 68 with a desirable PFI. Compound 68 demonstrated good in vitro pharmacology with excellent selectivity over CXCR1 and other chemokine receptors. Rat and dog pharmacokinetics (PK) revealed good oral bioavailability, high oral exposure, and desirable elimination half-life of the compound in both species. In addition, the compound demonstrated dose-dependent efficacy in the in vivo pharmacology neutrophil infiltration "air pouch" model in rodents after oral administration. Further, compound 68 is a CNS penetrant molecule with high unbound fraction in brain tissue.

(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.

TRIAZOLYL DERIVATIVES AS SYK INHIBITORS

Provided are triazole derivatives of Formula I which are potent inhibitors of spleen tyrosine kinase and pharmaceutical composition. The triazole derivatives are useful in the treatment and prevention of diseases mediated by said enzyme, such as asthma, COPD, rheumatoid arthritis, and cancer.

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.

Initiated tert-Butyl Hydroperoxide-loaded Low-temperature Autoxidation of Alkenes: Alternative Hydroperoxide Syntheses and the Preparation of a Complete Set of Reference Material

A complete set of characterization data for the allylic hydroperoxides prepared from 1-methylcyclohexene and the isomeric 4-methyloct-4-enes is presented.The data relies upon the preparation of allylic hydroperoxides by tert-butyl hydroperoxide-loaded autoxidations, singlet-ene oxidations and nucleophilic substitution reactions.Appropriate allylic alcohols and relevant scission products have been prepared to support the assignments given.