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271349

Sigma-Aldrich

5-Hexynenitrile

97%

Synonym(s):

5-Cyano-1-pentyne

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About This Item

Linear Formula:
HC≡C(CH2)3CN
CAS Number:
14918-21-9
Molecular Weight:
93.13
Beilstein:
1735926
MDL number:
MFCD00001978
UNSPSC Code:
12352100
PubChem Substance ID:
24856432
NACRES:
NA.22

Quality Level

100

Assay

97%

form

liquid

refractive index

n20/D 1.44 (lit.)

bp

115-117 °C (lit.)

density

0.889 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C#CCCCC#N

InChI

1S/C6H7N/c1-2-3-4-5-6-7/h1H,3-5H2

InChI key

JZYKFLLRVPPISG-UHFFFAOYSA-N

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Application

5-Hexynenitrile was used in the synthesis of annelated symmetric and asymmetric 3,3′-disubstituted 2,2′-bipyridines by cobalt(I)-catalyzed [2+2+2] cycloadditions with 1,3-diynes.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - 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)

107.6 °F - closed cup

Flash Point(C)

42 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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J A Varela et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 7(23), 5203-5213 (2002-01-05)
A one-step, regioselective synthesis of annelated symmetric and asymmetric 3,3'-disubstituted 2,2'-bipyridines by cobalt(I)-catalyzed [2+2+2] cycloadditions between 5-hexynenitrile and 1,3-diynes is described. In the symmetric case, the total regioselectivity of the first cycloaddition is ensured electronically by the conjugation of the
Zhiguo Li et al.
Chemphyschem : a European journal of chemical physics and physical chemistry, 15(11), 2247-2251 (2014-05-08)
The Cu(I) -catalyzed 1,3-dipolar azide-alkyne cycloaddition (CuAAC) has arisen as one of the most useful chemical transformations for introducing complexity onto surfaces and materials owing to its functional-group tolerance and high yield. However, methods for monitoring such reactions in situ

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