10297-06-0

Basic information

• Product Name: 6-CHLORO-1-HEXYNE
• Synonyms: 6-CHLORO-1-HEXYNE;5-HEXYNECHLORIDE;5-HEXYNYL CHLORIDE;1-Chloro-5-hexyne;6-CHLORO-1-HEXYNE 97%;6-CHLOROHEX-1-YNE;6-Chloro-1-hexyne,97%;6-Chloro-1-hexyne, 97% 25ML
• CAS NO: 10297-06-0
• Molecular Formula: C₆H₉Cl
• Molecular Weight: 116.59
• Product Categories: Acetylenes;Functionalized Acetylenes;Alkynyl;Halogenated Hydrocarbons;Organic Building Blocks;Building Blocks;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 10297-06-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 83 °C95 mm Hg(lit.)
• Flash Point: 99 °F
• Appearance: Clear yellow/Liquid
• Density: 0.962 g/mL at 25 °C(lit.)
• Vapor Pressure: 5.88mmHg at 25°C
• Refractive Index: n20/D 1.451(lit.)
• Storage Temp.: Flammables area
• CAS DataBase Reference: 6-CHLORO-1-HEXYNE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLORO-1-HEXYNE(10297-06-0)
• EPA Substance Registry System: 6-CHLORO-1-HEXYNE(10297-06-0)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 10297-06-0(Hazardous Substances Data)

Usage

Chemical Properties

Clear yellow liquid

Uses

6-Chloro-1-hexyne is used as an organic chemical synthesis intermediate.

InChI:InChI=1/C6H9Cl/c1-2-3-4-5-6-7/h1H,3-6H2

Upstream product

• 6940-78-9 4-chlorobutyl bromide 
• 74-86-2 acetylene 
• 14267-92-6 1-chloro-4-pentyne 
• 928-90-5 5-hexyl-1-ol 
• 10297-05-9 1-chloro 4-iodobutane 
• 1066-26-8 sodium acetylide 

Downstream Products

• 18215-67-3 1-<6-Chlor-hexin-(1)-yl>-cyclohexanol-(1) 
• 141503-18-6 9-Chloro-1,3-diphenyl-non-4-yn-1-one 
• 6097-08-1 2-(hex-5-yn-1-yl)isoindole-1,3-dione 
• 935858-03-0 2-(4-(hex-5-ynyl)piperazin-1-yl)-1,1,2-triphenylethanol 
• 1005325-88-1 C₂₅H₃₀ClNO₅ 
• 1213229-21-0 N-benzothiazol-6-yl-2-(3-(5-hexynyloxy)phenyl)acetamide 
• 1213229-18-5 N-benzothiazol-6-yl-2-(2-fluoro-3-(5-hexynyloxy)phenyl)acetamide 
• 1221065-57-1 (S,E)-8-chloro-2-ethyl-1-phenyloct-3-en-1-one 
• 1233676-40-8 C₁₄H₁₉Cl 
• 1202053-58-4 C₁₅H₁₈O₂ 
• 1296846-39-3 [8-chloro-4-(2-chloroethenylidene)octyl]benzene 
• 1296846-48-4 3-[6-chloro-2-(2-chloroethenylidene)hexyl]benzonitrile 
• 1315319-59-5 1,2,4-tris(4-chlorobutyl)benzene 
• 1354023-27-0 1-(6-chlorohex-1-yn-1-yl)-2-ethynylbenzene 

Relevant articles and documents

ω-alkyne-mono- and diphosphonates - Synthesis and sonogashira cross-coupling reaction with aryl halides

A convergent approach to functionalise aromatic compounds with a linker terminated by a phosphonate group is reported. The starting point of this strategy is the synthesis of five new ω-alkyne-phosphonates. The linker between the phosphonate group and the alkyne part is either an alkyl or an ether chain. This strategy is based on the use of the phosphonate group as the anchoring point for the attachment of organic compounds onto alumina and the alkyne group, which is used to functionalise aryl halide compounds by a Sonogashira cross-coupling. The use of 1,10-phenanthroline as substrate illustrates the application of this strategy to an aromatic ligand. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Preparation of cycloalkylacetylene compounds using dialkylaminomagnesium halide or bis(dialkylamino)magnesium

The process of invention reacts an alkynyl halide with a mixture that includes a dialkylaminomagnesium halide or a bis(dialkylamino)magnesium compound to produce a cycloalkylacetylene compound. Preferably, the dialkylaminomagnesium halide compound is of the general formula R 2 NMgX (where R is a linear, branched, or cyclic alkyl substituent or R 2 N represents a heterocyclic alkyl amine and X is Cl, Br, or I) and the bis(dialkylamino)magnesium compound is of the general formula (R 2 N) 2 Mg (where R is a linear, branched, or cyclic alkyl substituent or R 2 N represents a heterocyclic alkylamine). In a preferred method of the invention, the reaction is conducted at moderate temperatures for a period of about 12 to 24 hours. The reaction mixture preferably includes tetrahydrofuran (THF), or a hydrocarbon, or a hydrocarbonether mixture. The preferred compounds produced by this process are cycloalkylacetylene compounds having 5 to 20 carbons, such as cyclopropylacetylene and cyclobutylacetylene.