28077-73-8

Basic information

• Product Name: 2-Hexyne, 6-chloro-
• Synonyms: 2-Hexyne, 6-chloro-;6-Chloro-2-hexyne
• CAS NO: 28077-73-8
• Molecular Formula: C₆H₉Cl
• Molecular Weight: 116.59
• Mol File: 28077-73-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Hexyne, 6-chloro-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Hexyne, 6-chloro-(28077-73-8)
• EPA Substance Registry System: 2-Hexyne, 6-chloro-(28077-73-8)

Safety Data

• Hazardous Substances Data: 28077-73-8(Hazardous Substances Data)

Upstream product

• 14267-92-6 1-chloro-4-pentyne 
• 109-70-6 1.3-chlorobromopropane 
• 74-99-7 prop-1-yne 
• 74-88-4 methyl iodide 

Downstream Products

• 928-93-8 4-hexyn-1-ol 
• 28077-74-9 6-iodo-2-hexyne 
• 1192-29-6 2-ethyl-1-pyrroline 
• 62614-72-6 cis-1-chlorohex-4-ene 

Relevant articles and documents

Photochemical Route to a Represantative 1,8-Annulated 7-Methylene-1,3,5-cyclooctatriene

The bifunctional 2-cyclohexanone that is produced by addition of the Grignard reagent derived from 6-chloro-2-hexyne to 3-ethoxycyclohexenone was irradiated. Cycloaddition occurred to produce a highly sensitive tricyclic cyclobutene (14), which underwent ready double-bond migration in the presence of palladium(II) acetate.With the exocyclic ? bond in position, the α,β-unsaturated ketone functionality was next elaborated.Although oxidation of 15 via organoselenium methodology did give 16, the yield was only modest.A more expedient approach involved initial con version of 14 to its silyl enol ether and concurrent oxidation-olefin isomerization with Pd(II).Hydride reduction of the resulting dienone proceeded stereospecifically to deliver an allylic alcohol that underwent smooth dehydratation to give the target hydrocarbon 11 when treated with 2,4-dinitrobenzenesulfenyl chloride and triethylamine.The available evidence suggests that disrotatory ring opening within intermediate 18 occurs readily.

A Commercially Available and User-Friendly Catalyst for Hydroamination Reactions under Technical Conditions

The activity of a simple, commercially available copper salt, [Cu(NCMe)4](BF4) in intramolecular hydroamination reactions of alkynes and allenes is presented. Reactions were successfully carried out in technical acetonitrile in the presence of air. While attempts of alkene hydroamination failed, this catalyst was also found active in intermolecular aza-Michael reactions.

The scope of catalytic enantioselective tandem carbonyl ylide formation - Intramolecular [3 + 2] cycloadditions

Catalytic enantioselective tandem carbonyl ylide formation-intramolecular 1,3-dipolar cycloaddition reactions of 2-diazo-3,6-diketoesters show promising scope in terms of asymmetric induction as the tethered alkene/alkyne dipolarophile component is varied. Cycloadditions were found to occur in moderate to very good yields, with a difference in ee exhibited by the electronically different 2-diazo-3,6-diketoesters 1, 25 and 33, 34. Values for ee of up to 90% for alkene dipolarophiles and up to 86% for alkyne dipolarophiles were obtained.

An investigation of l,4,7-tri(4-alkynyl)-l,4,7-triazacyclononanes: Ligand synthesis and metal co-ordination chemistry

Three triazacyclononanes bearing pendant alkynyl groups [l,4,7-tri(4-pentynyl)-l,4,7-triazacyclononane (ptacn), 1,4,7-tri(5-phenyl-4-pentynyl)-l,4,7-triazacyclononane (pptacn) and 1,4,7-tri(4-hexynyl)-1,4,7-triazacyclononane (4htacn)] have been synthesize

Organolanthanide-catalyzed intramolecular hydroamination/cyclization of aminoalkynes

This contribution reports the efficient and regiospecific Cp'2LnCH(SiMe3)2 (Ln = La, Nd, Sm, Lu; Cp' = η5-Me5C5)- and Me2SiCp''2LnCH(SiMe3)2 (Ln = Nd, Sm; Cp'' = η5-Me4C5)-catalyzed hydroamination/cyclization of aliphatic and aromatic aminoalkynes of the formula RC≡C(CH2)(n)NH2 to yield the corresponding cyclic imines RCH2C=N(CH2)(n-1)CH2, where R, n, N(t) h-1 (°C) = Ph, 3, 77 (21°C); Ph, 3, 2830 (60°C); Me, 3, 96 (21°C); CH2=CMeCH2, 3, 20 (21°C); H, 3, 580 (21°C); Ph, 4, 4 (21°C); Ph, 4, 328 (60°C); Ph, 5, 0.11 (60°C); and SiMe3, 3, >7600 (21°C), and of aliphatic secondary amino-alkynes of the formula RC≡C(CH2)3NHR1 to generate the corresponding cyclic enamines RCH=CNR1(CH2)2CH2 where R, R1, N(t) h-1 (°C) = SiMe3, CH2=CHCH2, 56 (21°C); H, CH2=CHCH2, 27 (21°C); SiMe3, CH2=CH(CH2)3, 129 (21°C); and H, CH2=CH(CH2)3, 47 (21°C). Kinetic and mechanistic evidence is presented arguing that the turnover-limiting step is an intramolecular alkyne insertion into the Ln-N bond followed by rapid protonolysis of the resulting Ln-C bond. The use of larger metal ionic radius Cp'2LnCH(SiMe3)2 and more open Me2SiCp''2LnCH(SiMe3)2 complexes as the precatalysts results in a decrease in the rate of hydroamination/cyclization, arguing that the steric demands in the -C≡C- insertive transition state are relaxed compared to those of the analogous aminoolefin hydroamination/cyclization.

Synthesis of Arylcycloalkanes from ω-Alkenyl Benzylselenides

Arylcycloalkanes are produced from ω-alkenyl benzylselenides on reaction with alkyllithiums or on Lewis acid mediated electrophilic cyclisation.

Diastereoselective cycloisomerizations of enediynes via palladium catalysis

Considerations of atom economy drive a search for reactions that are simple additions which, performed intramolecularly, are cycloisomerizations. Exposure of acyclic enediynes to a catalyst generated by mixing a Pd(0) complex with acetic acid normally in

The synthesis of (E)-arylidene and allylidene cyclopentanes by means of a pallodium(0)-catalyzed complex

When treated with an unsaturated halide in a palladium-catalyzed process, the anions from γ-acetylenic malonates 4 and 5 stereospecifically lead to cyclopentanes having an exo tri- or tetra-substituted double bond. This reaction which forms simultaneously two carbon-carbon bonds is believed to proceed by nucleophilic attack of the anion on the triple bond activated by the σ-aryl or σ-vinyl palladium complex.

Photochemistry of N-Alk-4-enyl and N-Alk-5-enyl-phthalimides: Two Different Types of Cyclization Reaction

Photochemical reactions of N-alk-4- and -5-enylphthalimides (1a-e) have been investigated.In the photolyses of acetonitrile solutions of (1a-e), intramolecular cyclization reactions accompanying C(=O)-N bond cleavage to give (2a-e) were generally predominant, together with intramolecular hydrogen abstraction in some cases.Photolyses of cis- and trans-N-hex-4-enylphthalimides in acetonitrile solution showed stereospecific cyclization reactions; irridiation of cis-(1e) gave cis-(2e) and that of trans-(1e) gave trans-(2e) selectively with low conversion.In methanol (1d), which has a vinyl ether moiety, gave different types of cyclization product: namely, (8a) and (9a), methanol-incorporated products probably resulting from an intramolecular electron transfer process.