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469777

Sigma-Aldrich

6-Chloro-1-hexyne

98%

Synonym(s):

(4-Chlorobutyl)acetylene, 1-Chlorohex-5-yne

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About This Item

Linear Formula:
Cl(CH2)4C≡CH
CAS Number:
10297-06-0
Molecular Weight:
116.59
MDL number:
MFCD00013697
UNSPSC Code:
12352100
PubChem Substance ID:
24870482
NACRES:
NA.22

Quality Level

100

Assay

98%

refractive index

n20/D 1.451 (lit.)

bp

83 °C/95 mmHg (lit.)

density

0.962 g/mL at 25 °C (lit.)

SMILES string

ClCCCCC#C

InChI

1S/C6H9Cl/c1-2-3-4-5-6-7/h1H,3-6H2

InChI key

ZUKOCGMVJUXIJA-UHFFFAOYSA-N

Related Categories

General description

6-Chloro-1-hexyne is a halogenated hydrocarbon. It shows high reactivity in milling process during the synthesis of chloroalkyl-functionalized silicon nanoparticles due to the presence of triple bond.

Application

6-Chloro-1-hexyne was used in the preparation of novel bis(indolyl)maleimide pyridinophanes and disubstituted polyacetylenes bearing naphthalene pendants with varying spacer lengths. It may be used in the preparation of diethyl 6-chloro-1-hexynylphosphonate, by lithiation with n-BuLi followed by the reaction with diethyl chlorophosphate.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226 - H315 - H319 - H335

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

98.6 °F - closed cup

Flash Point(C)

37 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Comparison of amine-induced cyclization of 6-chloro-1-hexynylphosphonate and isobutyl 7-chlorohept-2-ynoate.
Srivastava HK, et al.
Tetrahedron, 65(22), 4389-4395 (2009)
Han-Cheng Zhang et al.
Bioorganic & medicinal chemistry letters, 17(10), 2863-2868 (2007-03-14)
Novel bis(indolyl)maleimide pyridinophanes 3, 9a, 9b, 10a, 10b, and 11 were prepared by cobalt-mediated [2+2+2] cycloaddition of an appropriate alpha,omega-diyne with an N,N-dialkylcyanamide. These macrocyclic heterophanes were found to be potent, selective inhibitors of glycogen synthase kinase-3beta. An X-ray structure
Jacky W Y Lam et al.
The journal of physical chemistry. B, 112(36), 11227-11235 (2008-08-19)
Poly(1-phenyl-1-alkyne)s bearing chromophoric pendants and containing alkyl spacers (-{(C 6H 5)CC[(CH 2) m OCOC 6H 4CCNp]} n - [P 1( m) ( m = 3, 4, 9); Np = 1-naphthyl]) were synthesized, and the effects of structural variations on the
Mechanochemical synthesis of functionalized silicon nanoparticles with terminal chlorine groups.
Hallmann S, et al.
Journal of Materials Research, 26(08), 1052-1060 (2011)

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