550477
3,9-Dodecadiyne
97%
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About This Item
Linear Formula:
CH3CH2C≡C(CH2)4C≡CCH2CH3
CAS Number:
Molecular Weight:
162.27
UNSPSC Code:
12352100
PubChem Substance ID:
MDL number:
InChI
1S/C12H18/c1-3-5-7-9-11-12-10-8-6-4-2/h3-4,9-12H2,1-2H3
SMILES string
CCC#CCCCCC#CCC
InChI key
SLQXYOMUNKJHRV-UHFFFAOYSA-N
assay
97%
refractive index
n20/D 1.465 (lit.)
bp
55-58 °C/0.5 mmHg (lit.)
density
0.809 g/mL at 25 °C (lit.)
General description
3,9-Dodecadiyne is an internal diyne that can undergo nickel-catalyzed cycloaddition with aryl nitriles to form pyridines.
Application
3,9-Dodecadiyne may be used as a monomer to prepare soluble hyperbranched poly(phenylenealkenes) via transition metal-catalyzed polycyclotrimerization. It may also be used as a starting material for preparing 1,2,3,4,9,10-hexaethyl-6,7,8,9-tetrahydroanthracene.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
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New catalysts for polymerizations of substituted acetylenes.
Tang BZ, et al.
ACS Symp. Ser., 760 (2000)
A nickel-catalyzed route to pyridines.
McCormick MM, et al.
Journal of the American Chemical Society, 127(14), 5030-5031 (2005)
Novel synthetic route to octasubstituted naphthalenes from four alkynes and one olefin unit via zirconacyclopentadienes and 1,2-diiodo-3,4,5,6-tetraalkylbenzene.
Zhou X, et al.
The Journal of Organic Chemistry, 69(13), 4559-4562 (2004)
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