161233
1,4-Diphenylbutadiyne
99%
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About This Item
Linear Formula:
C6H5C≡CC≡CC6H5
CAS Number:
Molecular Weight:
202.25
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
212-953-1
MDL number:
Assay:
99%
Form:
solid
InChI key
HMQFJYLWNWIYKQ-UHFFFAOYSA-N
InChI
1S/C16H10/c1-3-9-15(10-4-1)13-7-8-14-16-11-5-2-6-12-16/h1-6,9-12H
SMILES string
c1ccc(cc1)C#CC#Cc2ccccc2
assay
99%
form
solid
mp
86-87 °C (lit.)
General description
1,4-Diphenylbutadiyne reacts with [WI2(CO)3(NCMe)2] in CH2Cl2 to give the iodo-bridged dimer [W(μ-I)I(CO)(NCMe)(η2PhC2C2Ph)]2. 1,4-Diphenylbutadiyne on UV irradiation with olefins such as 2,3-dimethyl-2-butene, 1,4-cyclohexadiene and dimethyl fumarate yields cross-cycloaddition products.
Application
1,4-Diphenylbutadiyne was used in the preparation of 7,8-dehydropurpurin dimers via two-fold Pd-catalyzed [3+2] annulation of meso-bromoporphyrin.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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1,4-Diphenylbutadiyne, a new non-photodynamic phototoxic compound.
J Kagan et al.
Photochemistry and photobiology, 32(5), 607-611 (1980-11-01)
Norihito Fukui et al.
Angewandte Chemie (International ed. in English), 53(17), 4395-4398 (2014-03-20)
7,8-Dehydropurpurin has attracted much attention owing to the dual 18π- and 20π-electron circuits in its macrocyclic conjugation. The two-fold Pd-catalyzed [3+2] annulation of meso-bromoporphyrin with 1,4-diphenylbutadiyne furnished 7,8-dehydropurpurin dimers. The 8(a) ,8(a) -linked dimer displays a red-shifted and enhanced absorption
1, 4-Diphenylbutadiyne complexes of tungsten (II).
Ajayi-Obe T, et al.
Journal of Organometallic Chemistry, 468(1), 165-170 (1994)
Photoaddition reactions of 1, 4-diphenylbutadiyne with olefins.
Sang CS and Sung SK.
Tetrahedron Letters, 26(6), 765-766 (1985)
Carsten Glock et al.
Chemical communications (Cambridge, England), 48(56), 7094-7096 (2012-06-12)
Calciate-mediated intermolecular hydroamination of diphenylbutadiyne with N-phenyl and N-isopropyl-substituted anilines yields E- and Z-isomers of the corresponding 1-anilino-1,4-diphenylbut-1-ene-3-yne. In the case of HNPh(2) solely heterobimetallic K(2)Ca(NPh(2))(4) is able to effectively catalyze this hydroamination reaction in tetrahydrofuran at elevated temperatures.
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