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
• Article Data: 25

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

Description

Cyclohexylacetylene, also known as Ethynylcyclohexane, is an organic compound characterized by a cyclohexane ring with an acetylene functional group. It is a versatile building block in organic synthesis and has unique properties due to its triple bond, making it a valuable intermediate in various chemical reactions.

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 
• 17615-02-0 1-cyclohexyl-2-(triphenyl-λ⁵-phosphanylidene)ethan-1-one 
• 56772-65-7 2-cyclohexyl-1,1-dichloroethylene 
• 98-89-5 Cyclohexanecarboxylic acid 
• 695-12-5 vinylcyclohexane 
• 6917-84-6 Di-(cyclohexyl)-n-butylboran 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 1088-01-3 tricyclohexylborane 
• 861547-47-9 (1-chlorovinyl)cyclohexane 
• 67489-19-4 Cyclohexyl-methylthio-methylketon-p-tosylhydrazon 
• 81602-60-0 1,2-dibromo-1-cyclohexylethane 
• 100-49-2 cyclohexylmethyl alcohol 
• 67404-69-7 (Z)-1-iodo-2-cyclohexyl-1-ethene 

Downstream Products

• 73542-37-7 3-cyclohexyl-2-propynenitrile 
• 103262-97-1 1-cyclohexylvinyl acetate 
• 823-76-7 Cyclohexyl methyl ketone 
• 100314-63-4 butyric acid-(1-cyclohexyl-vinyl ester) 
• 64632-96-8 5-Cyclohexyl-2.3-dimethyl-4-pentyn-3-ol 
• 134864-35-0 (1E,3E)-1-cyclohexyl-1,3-octadiene 
• 93579-08-9 (E)-1-cyclohexyl-3-oxo-1-octene 
• 10564-83-7 4-cyclohexylbut-3-yn-2-one 
• 67857-89-0 (E)-penta-1,4-dienylcyclohexane 
• 57013-02-2 (Z)-1,2-dicyclohexylethylene 
• 37490-23-6 (E)-1-vinyl-2-cyclohexyl-catecholborane 
• 112043-59-1 7-cyclohexyl-(Z)-6-hepten-1-ol 
• 98978-39-3 N-(3-cyclohexyl-2-propynyl)-N-methyl-1-naphthalenemethanamine 
• 5664-17-5 cyclohexylallene 

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.

"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

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.