1121-49-9

Usage

Uses

Used in Pharmaceutical Industry:
Bromomethylenecyclohexane 96 is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique chemical structure allows for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, Bromomethylenecyclohexane 96 is utilized as an intermediate for the production of pesticides and other crop protection agents, contributing to enhanced agricultural productivity and crop protection.
Used in Chemical Reactions as a Solvent:
Bromomethylenecyclohexane 96 is employed as a solvent in a variety of chemical reactions, facilitating the process and improving the efficiency of these reactions.
Used in Organic Compound Synthesis:
As an intermediate, Bromomethylenecyclohexane 96 is instrumental in the synthesis of other organic compounds, expanding the range of available chemical products and contributing to the advancement of organic chemistry.

InChI:InChI=1/C7H11Br/c8-6-7-4-2-1-3-5-7/h6H,1-5H2

Upstream product

• 110-86-1 pyridine 
• 1713-51-5 bromo-(1-bromo-cyclohexyl)-acetic acid 
• 108-85-0 1-bromocyclohexane 
• 75-63-8 Bromotrifluoromethane 
• 931-51-1 cyclohexylmagnesiumchloride 
• 22690-21-7 1-bromo-1-bromomethylcyclohexane 
• 60014-80-4 1-dibromomethyl-1-(trimethylsiloxy)cyclohexane 
• 1034-49-7 (bromomethyl)triphenyl phosphonium bromide 
• 108-94-1 cyclohexanone 
• 1124-50-1 dibromomethyl-phenyl-mercury 
• 931-50-0 cyclohexylmagnesium bromide 
• 67-56-1 methanol 
• 60014-85-9 (1,1-dibromomethylene)cyclohexane 
• 52183-68-3 1-dibromomethyl-1-cyclohexanol 

Downstream Products

• 98758-86-2 (+/-)-α-cyclohexylidenemethyl-2-methylenebicyclo<3.1.0>hexane-1-methanol 
• 88908-88-7 2-Cyclohexylidene-1-((1R,5R)-2-methylene-bicyclo[3.1.0]hex-1-yl)-ethanol 
• 138572-92-6 tert-Butyl-[4-((Z)-2-cyclohex-1-enyl-vinyl)-3,6,6-trimethyl-cyclohex-3-enyloxy]-dimethyl-silane 
• 88908-95-6 (+/-)-(Z)-2-(3β,5α-dihydroxy-2-methylene-cyclohexylidene)ethylidenecyclohexane 
• 53723-48-1 1,1'-(1,2-ethanediylidene)biscyclohexane 
• 591-49-1 1-methylcyclohex-1-ene 
• 184-26-9 1,4-dioxaspiro[4.6]undecane 
• 1192-37-6 methylenecyclohexane 
• 1552-91-6 cyclohexylideneacetic acid 
• 16963-29-4 4-(cyclohexylidenemethyl)morpholine 
• 929032-91-7 4-cyclohexylidenemethyl-4-hydroxy-2,3-dimethoxy-cyclobut-2-enone 
• 7577-08-4 1-(cyclohexylidenemethyl)-4-methoxy-benzene 
• 88924-29-2 tributyl(cyclohexylidenemethyl)stannane 

Relevant academic research and scientific papers

A Convenient Stereoselective Reduction of Gem-Dibromides with a Combination of Dimethyl Phosphite and Potassium Carbonate

An efficient and highly stereoselective reduction of a gem-dibromocyclopropane to the corresponding monobromocyclopropane under mild reaction conditions was developed using a combination of dimethyl phosphite and potassium carbonate. This reaction provided a simple and practical way for the synthesis of the valuable monobromocyclopropanes and β-monobromoalkenes.

Thermally induced cyclobutenone rearrangements and domino reactions

(Chemical Equation Presented) Four thermal-rearrangement pathways and a domino reaction leading to quinones arise from the thermolysis of cyclobutenones. The course of vinylcyclobutenone rearrangements is dictated by the nature of the substituent, R (see

Halodephosphorylation of α,β-unsaturated phosphonic acid monoesters

Reaction of α,β-ethylenic and acetylenic phosphonic acid monoesters with (biscollidine)iodine(I) or (biscollidine)bromine(I) hexafluorophosphate led to α,β-unsaturated halides by, without precedent, dephosphorylation reactions.

4-endo-trig cyclization processes using bis(collidine)bromine(i) hexafluorophosphate as reagent: Preparation of 2-oxetanones, 2-azetidinones, and oxetanes

Reaction in methylene chloride of bis(collidine)bromine(I) hexafluorophosphate with α,β-unsaturated acids and α,β-unsaturated N- sulfonamides was found to lead diastereospecifically to the corresponding 2- oxetanones and 2-azetidinones in moderate yields (23-60%), by an almost unknown 4-endo cyclization. This process allow the synthesis of these interesting classes of products in one step from common substrates. Similarly, the reaction of cinnamic alcohols led, by the same cyclization procedure, to oxetanes (20-36%); the presence of a gem-dimethyl group in α of the alcohol function appeared beneficial.

The regiochemistry and stereochemistry of α,β-epoxysilane ring opening with silyl halides or pseudohalides

The reaction of trimethylsilyl halides with α,β-epoxysilanes leads to either a vinyl halide by addition/elimination or a vinyl enol ether by rearrangement; the route depends upon the nature of the groups attached to the epoxyde ring.With groups β to the silicon that can stabilise an adjacent positive charge the directive effect of silicon towards substitution at the α position is overcome such that the enol ether is obtained.Trimethylsilyl pseudohalides behave similarly except that the intermediate addition product can be isolated.The stereoselectivity of ring opening is found to vary with the reagent. epoxyde / epoxysilane / ring opening / regiochemistry / halosilane

Efficient Syntheses of Multisubstituted Methylenecyclopropanes via Novel Ultrasonicated Reactions of 1,1-Dihaloolefins and Metals

Ultrasonicated reactions of 1,1-dihaloolefins with lithium, magnesium or sodium in the presence of alkenes rapidly afford multisubstituted methylenecyclopropanes.

New strategies for the synthesis of vitamin D metabolites via Pd-catalyzed reactions

The invention of new palladium-catalyzed reactions offers new insights into synthetic strategies directed toward the vitamin D system. The palladium-catalyzed cycloisomerization of 1,6- and 1,7-enynes to dialkylidenecycloalkanes permits a lynchpin approach to the A ring of vitamin Ds. Using the thioacetal of formaldehyde, the proper subunits containing the olefin and the acetylene were attached. Pd(2+) effected cycloisomerization to an A ring subunit. A more effective strategy evolved from the evolution of a Pd-catalyzed alkylative cyclization of enynes. Whereas prior work established the feasibility of this process for 1,6-enynes, model studies reported herein demonstrate the feasibility of its extension to 1,7-enynes. This reaction permits the creation of a new concept for vitamin D synthesis wherein A ring formation is concomitant with its attachment to an appropriate CD fragment. An asymmetric synthesis of the requistite 1,7-enyne required six steps. Bromomethylenation of Grundmann's ketone and its side chain hydroxylated derivative proceeded with excellent geometrical selectivity (>30:1) using the Wittig reaction. A Pd catalyst generated from (dba)3Pd2·CHCl3 and triphenylphosphine stitched together these two units in a single step resulting in syntheses of alphacalcidiol and calcitriol.

Synthesis of Mono and gem-Dihalogeno-olefins from Carbonyl Compounds and in situ Generated Lithium Carbenoids

The treatment of carbonyl compounds (5) with dihalogenomethane and lithium dicyclohexylamide at -78 deg C leads after acid hydrolysis to the crude alcohols (6), which by silylation with trimethylchlorosilane-hexamethyldisilazane-pyridine affords the crude

A General Method for the Synthesis of 3,5-Cyclovitamin D3 and Derivatives. A Stereoselective Synthesis of Vitamin D3

A stereoselective synthesis of vitamin D3 (1) was achieved via 3,5-cyclovitamin D3 (33) which was synthesized from the chiral aldehyde (3) and the vinyl bromide (27) derived from Grundmann's ketone (25). (+/-)-(Z)-5-(2-Cyclohexylidene-ethylidene)-4-methylenecyclohexane-r-1, t-3-diol (24) as a model compound of 1α-hydroxyvitamin D3 was also stereoselectively synthesized via the solvolysis of (+/-)-α-cyclohexylidenemethyl-3β-methoxymethoxy-2-methylenebicyclohexane-1-methanol (21) which was prepared from the aldehyde (12) and the organostannane (16).