932-86-5

Basic information

• Product Name: (2-bromoethylidene)cyclohexane
• Synonyms: (2-bromoethylidene)cyclohexane
• CAS NO: 932-86-5
• Molecular Formula: C₈H₁₃Br
• Molecular Weight: 189.09282
• EINECS: 213-259-1
• Mol File: 932-86-5.mol

Chemical Properties

• Boiling Point: 220.2°Cat760mmHg
• Flash Point: 83.6°C
• Appearance: /
• Density: 1.381g/cm³
• Vapor Pressure: 0.17mmHg at 25°C
• Refractive Index: 1.591
• CAS DataBase Reference: (2-bromoethylidene)cyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: (2-bromoethylidene)cyclohexane(932-86-5)
• EPA Substance Registry System: (2-bromoethylidene)cyclohexane(932-86-5)

Safety Data

• Hazardous Substances Data: 932-86-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(2-bromoethylidene)cyclohexane is used as a key intermediate in various organic synthesis reactions. Its unique structure allows it to participate in a range of chemical transformations, making it a valuable compound in the field of organic chemistry.
Used in Chemical Transformations:
As a reagent, (2-bromoethylidene)cyclohexane is utilized in chemical transformations to produce a variety of desired products. Its reactivity with other compounds enables the synthesis of new molecules with potential applications in various industries.
Used in Pharmaceutical Industry:
(2-bromoethylidene)cyclohexane is used as a building block for the synthesis of pharmaceutical compounds. Its unique chemical properties allow it to be incorporated into drug molecules, potentially leading to the development of new medications.
Used in Chemical Research:
In the field of chemical research, (2-bromoethylidene)cyclohexane serves as a model compound for studying reaction mechanisms and exploring new synthetic pathways. Its reactivity and structural features make it an interesting subject for scientific investigation.
Safety Note:
It is important to handle (2-bromoethylidene)cyclohexane with caution, as it is a flammable and potentially hazardous material. Proper safety measures should be taken during its use to minimize risks.

InChI:InChI=1/C8H13Br/c9-7-6-8-4-2-1-3-5-8/h6H,1-5,7H2

Upstream product

• 1940-19-8 1-vinylcyclohexanol 
• 932-89-8 2-cyclohexylidene ethanol 
• 110-86-1 pyridine 
• 7789-60-8 phosphorus tribromide 
• 1552-92-7 ethyl cyclohexylideneacetate 
• 108-94-1 cyclohexanone 
• 1826-67-1 vinyl magnesium bromide 
• 78-27-3 1-Ethynylcyclohexan-1-ol 

Downstream Products

• 52414-80-9 2-(2-cyclohexyliden-ethyl)-2-methyl-cyclohexane-1,3-dione 
• 854724-19-9 3-<2-Dimethylamino-aethyl>-cyclohexen-(1) 
• 5848-61-3 ethyl-(2-cyclohexyliden-ethyl)-malonic acid diethyl ester 
• 701-98-4 β-cyclohexylidenepropionic acid 
• 107256-79-1 α-[(diisopropylamino)ethyl]-α-(2-cyclohexylethyl)-o-chlorophenylacetamide 
• 1001653-47-9 [2-((Z)-3-ethynyl-oct-2-enyloxy)-ethylidene]-cyclohexane 
• 1001653-51-5 [2-((Z)-3-ethynyl-1-isopropyl-oct-2-enyloxy)-ethylidene]-cyclohexane 
• 1001653-27-5 [2-((Z)-3-methyl-pent-2-en-4-ynyloxy)-ethylidene]-cyclohexane 
• 1001653-43-5 [(Z)-3-(2-cyclohexylidene-ethyloxy)-1-ethynylpropenyl]benzene 
• 66165-04-6 (2-cyclohexylideneethyl)(phenyl)sulfane 
• 1421845-45-5 C₁₇H₁₉NO 
• 78249-37-3 6-Cyclohexylidene-3-oxo-hexanoic acid methyl ester 
• 94371-47-8 (1S,4R,5S)-5-Benzenesulfonyl-5-(2-cyclohexylidene-ethyl)-6-methylene-bicyclo[2.2.1]hept-2-ene 
• 74788-88-8 α-<(diisopropylamino)ethyl>-α-(2-cyclohexylidenylethyl)-o-chlorophenylacetonitrile 

Relevant articles and documents

The Application of 1,2-Oxazinanes as Chiral Cyclic Weinreb Amide-Type Auxiliaries Leading to a Three-Component, One-Pot Reaction

1,2-Oxazines were synthesised via a copper-catalysed aerobic acyl nitroso Diels-Alder reaction from 1,4-disubstituted 1,3-dienes and N-Boc-hydroxylamine. From this, 1,2-oxazinanes were obtained in a novel follow-up reaction path. The stability of several 1,2-oxazines and 1,2-oxazinanes towards organometallic compounds was tested to rate their operability as cyclic chiral Weinreb amide auxiliaries. 3,6-Di-tertbutyl-1,2-oxazinane gave the best results and was introduced as a chiral Weinreb amide-type auxiliary to yield chiral α-substituted ketones in a diastereomeric ratio of up to 98:2. The removal of the auxiliary can be performed with BuLi to form unsymmetrical α-chiral ketones. Thereafter, the chiral auxiliary can be re-isolated and purified by sublimation under vacuum.

Visible-Light-Promoted Intramolecular α-Allylation of Aldehydes in the Absence of Sacrificial Hydrogen Acceptors

We report herein an unprecedented protocol for radical cyclization of aldehydes with pendant alkenes via synergistic photoredox, cobaloxime, and amine catalysis. The transformation was achieved in the absence of external oxidants, providing a variety of 5-, 6-, and 7-membered ring products with alkene transposition in satisfactory yields. The reaction exhibits wide functional group compatibility and occurs under mild conditions with extrusion of H2.

Hypervalent iodine initiated intramolecular alkene dimerisation: A stereodivergent entry to cyclobutanes

The emergence of new methods for the stereoselective synthesis of strained carbocycles is a challenging but worthwhile endeavour. Cyclobutanes, in particular, have attracted the attention of both medicinal chemists and material scientists for their unique properties. Herein, we present a new method that allows access to highly functionalized cyclobutanes with complementary all-trans and trans-cis-trans relative stereochemistry, that could not be accessed before. This approach consists of an intramolecular dimerisation of non-conjugated dienes using an oxidative single electron transfer (SET) process, and is initiated by catalytic amounts of hypervalent iodine reagents. The potential uses of these cyclobutanes is demonstrated with selective functionalization, including the formation of diols and carboxylic acids.

Synthesis of Cyclobutene-Fused Eight-Membered Carbocycles through Gold-Catalyzed Intramolecular Enyne [2+2] Cycloaddition

Cationic gold(I) complexes with hollow-shaped triethynylphosphine ligands efficiently catalyzed intramolecular [2+2] cycloaddition of 1,9-enynes to afford cyclobutene-fused eight-membered carbocycles that were difficult to synthesize by other catalytic systems. Various 1,9-enynes with carbon linkers with or without a fused ring underwent efficient [2+2] cycloaddition with 5 mol% of the Au catalyst bearing the triarylmethyl-end-capped triethynylphosphine in CH2Cl2 at rt in the presence of MS 4A as an additive. More challenging 1,9-enyne substrates with fully saturated acyclic carbon linkers underwent eight-membered ring formation at 60 °C in ClCH2CH2Cl in the absence of MS 4A, forming monocyclic 1,3-dienes as major products. (Figure presented.).

Transition-Metal-Free Formylation of Allylzinc Reagents Leading to α-Quaternary Aldehydes

The first example of formylation of allylzinc reagents using S-phenyl thioformate is presented. The reaction proceeded under mild conditions without any transition-metal catalyst, forming quaternary carbon centers with reactive functionalities, such as formyl and vinyl groups. Moreover, Barbier-type formylation of an allylic bromide with a sterically demanding thioformate was achieved. As a preliminary result, asymmetric formylation was conducted using a menthol-derived chiral thioformate.

Carbene-catalyzed desymmetrization of 1,3-diols: Access to optically enriched tertiary alkyl chlorides

The introduction of a chlorine atom to a carbon center in an enantioselective manner via conventional C-Cl bond formation is difficult. Here we report a new approach to this class of tertiary alkyl chlorides with high optical purities. Instead of forming a new C-Cl bond, our approach involves carbene-catalyzed desymmetrization of 2-chloro-1,3-diols as the key step to set up the chiral carbon center with excellent enantiomeric excess.

Preparation of polycyclic compounds by intramolecular photospirocyclization and photocycloaddition reactions of 4-alkenyl-1-cyanonaphthalene derivatives

Photoreactions of 4-pentenyl-1-cyanonaphthalenes yield spirocyclic products along with [4?+?2] cycloadducts. Photoreactions of 5-phenyl derivatives produce a product having tricyclo[6.3.0.01,4]undecadiene skeleton. Formation of angular triquinanes takes place in photoreactions of cycloalkene-linked cyanonaphthalenes. The observation demonstrates that π–π arene ring interactions, steric hindrance, and suitable locations of reaction sites in syn and anti singlet exciplexes govern the modes followed in intramolecular photoreactions of 4-alkenyl-1-cyanonaphthalenes.

Dialkylzinc-mediated allylic polyfluoroarylation reaction

Abstract We present an allylic polyfluoroarylation reaction with broad substrate scope and excellent functional group tolerance, using organozinc reagents under mild conditions. A catalytic amount of triphenylphosphine oxide efficiently promotes iodine-zinc exchange reaction between polyfluoroaryl iodide and dimethylzinc, and the resulting phosphine oxide-activated polyfluoroarylzinc undergoes substitution reaction with allylic halides to afford the corresponding polyfluoroarylated products.

GERANYLGERANYLACETONE DERIVATIVES

Provided herein are geranylgeranylacetone derivatives and methods of using them.

Selectivity control by silver catalysts in the cycloisomerization of 1,6-enynes derived from propiolamides

Silver-catalyzed cycloisomerizations of 1,6-enynes derived from propiolamides led to a selective formation of Alder-ene type 1,4-dienes. Interestingly, AgNTf2 outperformed gold or platinum catalysts in terms of selectivity and reactivity, providing the 1,4-dienes at room temperature. The presence of C(5) carbonyl group in combination with Ag salts is key to the selectivity and the β-oxo coordinated silver carbenoids were proposed as an intermediate based on the reaction profiles.