17715-00-3

Basic information

• Product Name: 3-CYCLOHEXYL-1-PROPYNE
• Synonyms: 3-CYCLOHEXYL-1-PROPYNE;1-PROP-2-YNYLCYCLOHEXANE;(2-propynyl)-cyclohexan;(2-propynyl)cyclohexane;2-propynyl-cyclohexan;2-propynylcyclohexane;3-cyclohexyl-propyn;3-Cyclohexylpropyne
• CAS NO: 17715-00-3
• Molecular Formula: C₉H₁₄
• Molecular Weight: 122.21
• Product Categories: Alkynes;Organic Building Blocks;Terminal;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 17715-00-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 157-158 °C(lit.)
• Flash Point: 95 °F
• Appearance: /
• Density: 0.845 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.92mmHg at 25°C
• Refractive Index: n20/D 1.4590(lit.)
• Water Solubility: Slightly soluble in water.
• BRN: 1849402
• CAS DataBase Reference: 3-CYCLOHEXYL-1-PROPYNE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CYCLOHEXYL-1-PROPYNE(17715-00-3)
• EPA Substance Registry System: 3-CYCLOHEXYL-1-PROPYNE(17715-00-3)

Safety Data

• Hazard Codes: Xn
• Statements: 10-22-41
• Safety Statements: 16-26-36
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• RTECS: UK4725000
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 17715-00-3(Hazardous Substances Data)

Usage

Uses

3-Cyclohexyl-1-propyne, is used as a pharmaceutical intermediate. It can be used to produce (5-bromo-4,4,5,5-tetrafluoro-pent-2-enyl)-cyclohexane at the temperature of 40°C. It will need reagents (NH4)2S2O8, HCO2Na·2H2O and solvent dimethylformamide with the reaction time of 3 hours. It is also used as organic synthesis intermediates.

InChI:InChI=1/C9H14/c1-2-6-9-7-4-3-5-8-9/h9H,3-5,7-8H2,1H3

Upstream product

• 13169-00-1 Methoxyallene 
• 931-51-1 cyclohexylmagnesiumchloride 
• 542-18-7 cyclohexyl chloride 
• 513-31-5 2-bromoallyl bromide 
• 931-50-0 cyclohexylmagnesium bromide 
• 5664-17-5 cyclohexylallene 
• 106-96-7 propargyl bromide 

Downstream Products

• 97196-80-0 1,1-diethoxy-4-cyclohexylbut-2-yne 
• 134589-75-6 [4-Cyclohexyl-1-phenyl-but-2-yn-(E)-ylidene]-phenyl-amine 
• 1678-92-8 propylcyclohexane 
• 103-65-1 phenylpropane 
• 2114-42-3 allylcyclohexane 
• 460752-15-2 2-cyclohexyl-3-butyn-1-ol 
• 132539-51-6 (3-cyclohexylprop-1-ynyl)trimethylsilane 
• 1210053-95-4 (E)-5-(2-cyclohexylethyl)-4-ethylidene-3,4-dihydro-2H-pyrrole 
• 1228115-74-9 C₁₅H₂₃NO₃ 
• 1235872-93-1 3-(2-cyclohexyl-1-methylethyl)-1H-indole 
• 1239341-59-3 3-cyclohexyl-2-(pentylthio)-1-propene 
• 1292358-61-2 1-benzyl-3-hydroxy-3-(3-cyclohexylprop-1-ynyl)indolin-2-one 
• 1271376-78-3 1-(3-(4-(cyclohexylmethyl)-1H-1,2,3-triazol-1-yl)propyl)piperidine 
• 1271376-74-9 1-(3-(4-(cyclohexylmethyl)-1H-1,2,3-triazol-1-yl)propyl)-4-methylpiperazine 

Relevant articles and documents

The stereochemistry of the vinylogous Peterson elimination

Base-induced eliminations of the vinylogous β-hydroxysilanes 7, 9, 11 and 12 are stereospecifically syn, giving largely the trans,trans-diene 8 from 7 and 11, the cis,trans-diene 10 from 9, and the trans,cis-diene 13 from 12. When a cis double bond is produced, it is selectively placed adjacent to the carbon atom that originally carried the hydroxy group. E2′ Reactions with silyl as the electrofugal group and acetate as the nucleofugal group, initiated by fluoride ion, are not stereospecific, but can be highly stereoselective in favour of the trans,trans-diene 8 when the carbon substituent at the silicon-bearing end is a cyclohexyl group and the double bond is cis, and in favour of the trans,cis-diene 13 when the carbon substituent at the silicon-bearing end is a methyl group and the double bond is trans. Attempts to use the Peterson reactions to make o-quinodimethanes stereospecifically failed, with no evidence of 1,4-elimination from the alcohols 40 and 41. The corresponding E2′ reaction from the esters using fluoride ion on the acetates or formates 46 and 47 gave stereoselectively the E,E-quinodimethane 48.