931-48-6

Basic information

• Product Name: CYCLOHEXYLACETYLENE
• Synonyms: Cyclohexane, ethynyl-;cyclohexane,ethynyl-;ethyne,cyclohexyl-;ETHYNYLCYCLOHEXANE;CYCLOHEXYLACETYLENE;CYCLOHEXYLETHYNE;Cyclohexane, ethynyl- (6CI, 7CI, 8CI, 9CI);1-Ethynylcyclohexane
• CAS NO: 931-48-6
• Molecular Formula: C₈H₁₂
• Molecular Weight: 108.18
• EINECS: 213-236-6
• Mol File: 931-48-6.mol

Chemical Properties

• Melting Point: 130-132 °C
• Boiling Point: 130-132 °C(lit.)
• Flash Point: 66 °F(lit.)
• Appearance: Yellow to light brown/liquid
• Density: 0.828 g/mL at 25 °C(lit.)
• Vapor Pressure: 13.9mmHg at 25°C
• Refractive Index: n20/D 1.4540(lit.)
• Storage Temp.: Flammables area
• Water Solubility: Immiscible with water.
• BRN: 1815535
• CAS DataBase Reference: CYCLOHEXYLACETYLENE(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLOHEXYLACETYLENE(931-48-6)
• EPA Substance Registry System: CYCLOHEXYLACETYLENE(931-48-6)

Safety Data

• Hazard Codes: F
• Statements: 11-36/37/38
• Safety Statements: 16-37/39-26
• RIDADR: UN 3295 3/PG 2
• WGK Germany: 3
• F: 10
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 931-48-6(Hazardous Substances Data)

Usage

Uses

Used in Catalyst Preparation:
Cyclohexylacetylene is used as a vital intermediate in the preparation of hydrido-vinylidene complexes of osmium. These complexes serve as catalysts in several homogeneous and heterogeneous catalytic reactions, such as alkene oligomerization, polymerization, and Fischer-Tropsch synthesis.
Used in Organometallic Chemistry:
Cyclohexylacetylene (Ethynylcyclohexane) is used in the preparation of organometallic complexes, such as [Os((E)-CH=CHR)(=C=C=CPh2)(CH3CN)2(P(i)Pr3)2]BF4 (R = Ph, Cy). These complexes have potential applications in various chemical transformations and catalysis processes, showcasing the importance of cyclohexylacetylene in organometallic chemistry.

InChI:InChI=1/C8H12/c1-2-8-6-4-3-5-7-8/h1,8H,3-7H2

Upstream product

• 5173-61-5 (2,2-dichloro-ethyl)-cyclohexane 
• 823-76-7 Cyclohexyl methyl ketone 
• 81602-60-0 1,2-dibromo-1-cyclohexylethane 
• 67489-19-4 Cyclohexyl-methylthio-methylketon-p-tosylhydrazon 
• 1088-01-3 tricyclohexylborane 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 6917-84-6 Di-(cyclohexyl)-n-butylboran 
• 60754-49-6 1,1-dibromo-2-cyclohexylethene 
• 66270-60-8 (cyclohexylethynyl)trimethylsilane 
• 17615-02-0 1-cyclohexyl-2-(triphenyl-λ⁵-phosphanylidene)ethan-1-one 
• 122471-82-3 1-(2-Cyclohexylidene-2-phenylselanyl-ethanesulfonyl)-4-methyl-benzene 
• 246023-17-6 α-(dichloromethyl)cyclohexanemethanol 4-methylbenzenesulfonate 
• 861547-47-9 (1-chlorovinyl)cyclohexane 
• 56772-65-7 2-cyclohexyl-1,1-dichloroethylene 

Downstream Products

• 73542-37-7 3-cyclohexyl-2-propynenitrile 
• 65199-70-4 (+/-)-4-cyclohexyl-but-3-yn-2-ol 
• 5664-20-0 vinylidenecyclohexane 
• 100-41-4 ethylbenzene 
• 4361-27-7 cyclohexylpropiolic acid 
• 103262-97-1 1-cyclohexylvinyl acetate 
• 823-76-7 Cyclohexyl methyl ketone 
• 18736-95-3 1-cyclohexylpropyne 
• 100314-63-4 butyric acid-(1-cyclohexyl-vinyl ester) 
• 67500-42-9 2-Cyclohexyl-cycloprop-2-enecarboxylic acid methyl ester 
• 64632-96-8 5-Cyclohexyl-2.3-dimethyl-4-pentyn-3-ol 
• 57628-03-2 (3,3-dimethylbut-1-ynyl)cyclohexane 
• 22031-57-8 (E)-3-cyclohexylprop-2-enenitrile 
• 134864-35-0 (1E,3E)-1-cyclohexyl-1,3-octadiene 

Relevant articles and documents

Difluorocyclobutylacetylenes as positive allosteric modulators of mGluR5 with reduced bioactivation potential

Schizophrenia is a serious illness that affects millions of patients and has been associated with N-methyl-D-aspartate receptor (NMDAR) hypofunction. It has been demonstrated that activation of metabotropic glutamate receptor 5 (mGluR5) enhances NMDA receptor function, suggesting the potential utility of mGluR5 positive allosteric modulators (PAMs) in the treatment of schizophrenia. Herein we describe the optimization of an mGluR5 PAM by replacement of a phenyl with aliphatic heterocycles and carbocycles as a strategy to reduce bioactivation in a biaryl acetylene chemotype. Replacement with a difluorocyclobutane followed by further optimization culminated in the identification of compound 32, a low fold shift PAM with reduced bioactivation potential. Compound 32 demonstrated favorable brain uptake and robust efficacy in mouse novel object recognition (NOR) at low doses.

Lanthanide-Catalyzed Reversible Alkynyl Exchange by Carbon–Carbon Single-Bond Cleavage Assisted by a Secondary Amino Group

Lanthanide-catalyzed alkynyl exchange through C?C single-bond cleavage assisted by a secondary amino group is reported. A lanthanide amido complex is proposed as a key intermediate, which undergoes unprecedented reversible β-alkynyl elimination followed by alkynyl exchange and imine reinsertion. The in situ homo- and cross-dimerization of the liberated alkyne can serve as an additional driving force to shift the metathesis equilibrium to completion. This reaction is formally complementary to conventional alkyne metathesis and allows the selective transformation of internal propargylamines into those bearing different substituents on the alkyne terminus in moderate to excellent yields under operationally simple reaction conditions.

"quick and click" assembly of functionalised indole rings via metal-promoted cyclative tandem reactions

An efficient and convenient synthesis of a variety of decorated indoles using a three-component tandem metal-catalysed process is described. We propose here a new "synthetic kit" that allows for the "quick and click" assembly of indole rings using readily available, and inexpensive starting materials under environmentally friendly reaction conditions. This journal is

Thieme Chemistry Journal Awardees - Where are they now? A general one-step synthesis of alkynes from enolisable carbonyl compounds

Terminal and internal acetylenes were obtained in good to excellent isolated yields from carbonyl compounds by converting the carbonyl functionality into the enol nonaflate intermediate followed by elimination to give the C-C triple bond. The one-pot transformations were uniformly induced by phosphazene bases combined with mildly electrophilic nonafluorobutane-1-sulfonyl fluoride. The method is the most general among those reported to date as it applies to both acyclic ketones and aldehydes. Only moderate kinetic regioselectivity in favour of alk-1-yne achieved from methyl n-alkyl ketone represents a limitation of the method. In all the other instances, individual acetylenic products were obtained. Georg Thieme Verlag Stuttgart.

Terminal alkynes from aldehydes via dehydrohalogenation of (Z)-1-iodo-1-alkenes with TBAF

Terminal alkynes were prepared in near quantitative yields via dehydrohalogenation of (Z)-1-iodo-1-alkenes with tetrabutylammonium fluoride (TBAF) under mild conditions. The methodology was expanded to include a one-pot, direct synthesis of terminal alkynes from aldehydes without the necessity of isolating and purifying the intermediate iodoalkene.

Design, synthesis and biological evaluation of novel, simplified analogues of laulimalide: Modification of the side chain

Novel, simplified analogues of the microtubule-stabilizing anticancer agent laulimalide, including the first derivatives with unnatural side chains, were designed by molecular modelling, synthesized by a late-stage diversification strategy, and evaluated in vitro for growth inhibition of human ovarian carcinoma cell lines (A2780, A2780/AD10).

Process for the preparation of cyclopropylacetylene

The present invention relates generally to novel methods for the preparation of cyclopropylacetylene which is an essential reagent in the asymmetric synthesis of (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one; a useful human immunodeficiency virus (HIV) reverse transcriptase inhibitor with superior anti-retroviral activity. In the process, for example, cyclopropane carboxaldehyde is alkylated to form 1,1,1-trichloro-2-cyclopropyl-ethanol; which in turn undergoes elimination to form 1,1-dichloro-2-cyclopropyl-ethene; which in turn undergoes elimination to form cyclopropyl acetylene.

Reaction of Grignard compounds with 4-chloro-2-methyl-3-butyn-2-ol in Diethyl Ether equivalents

Reactions of RMgX · THF complexes with 4-chloro-2-methyl-3-butyn-2-ol in aromatic hydrocarbons were studied. The complexes formed by arylmagnesium halides require the presence of anisole for the reaction to occur. 4-Chloro-2-methyl-3-butyn-2-ol can be synthesized by reaction of 2-methyl-3-butyn-2-ol with sodium hypochloride in the two-phase system water-benzene.

A new and practical synthesis of vinyl dichlorides via a non-Wittig-type approach

A practical approach for the conversion of aldehydes to vinyl dichlorides has been developed. These are three-step, one-pot reactions involving the formation of trichlorocarbinol by treatment of aldehydes with trichloroacetic acid and sodium trichloroacetate followed by in situ protection and elimination reactions to form the desired vinyl dichlorides in 85 to 95% yields. (C) 2000 Dupont Pharmaceuticals Company.