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Key Documents

D204803

Sigma-Aldrich

Diphenylacetylene

98%

Synonym(s):

Tolan

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About This Item

Linear Formula:
C6H5C≡CC6H5
CAS Number:
Molecular Weight:
178.23
Beilstein:
606478
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

98%

form

crystals

bp

170 °C/19 mmHg (lit.)

mp

59-61 °C (lit.)

density

0.99 g/mL at 25 °C (lit.)

SMILES string

c1ccc(cc1)C#Cc2ccccc2

InChI

1S/C14H10/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H

InChI key

JRXXLCKWQFKACW-UHFFFAOYSA-N

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Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Neola F McKinley et al.
The Journal of organic chemistry, 71(25), 9552-9555 (2006-12-02)
Carbolithiation of diphenylacetylene can be exploited to generate (E)-1-lithio-1,2-diphenylalkyl-1-enes which can be reacted in situ with triisopropylborate to stereoselectively provide (E)-1,2-diphenyl-1-alkylene boronic acids. These tetrasubstituted vinylboronic acids served as versatile intermediates for the generation of tetrasubstituted olefins with retention of
Anion-dependent switching: dynamically controlling the conformation of hydrogen-bonded diphenylacetylenes.
Ian M Jones et al.
Angewandte Chemie (International ed. in English), 50(20), 4597-4600 (2011-04-16)
Ian M Jones et al.
Angewandte Chemie (International ed. in English), 50(52), 12569-12571 (2011-12-17)
The conformational equilibrium of a pH-dependent switch based on an intramolecularly H-bonded diphenylacetylene can be predictably biased by using electron-donating or -withdrawing groups. Furthermore, protonation of the electron-donating dimethylamino group converts it into an electron-withdrawing dimethylammonium cation with a concomitant
H Zhang et al.
Organic letters, 3(20), 3083-3086 (2001-09-28)
[reaction: see text] A variety of substituted beta- and gamma-carbolines have been prepared in good to excellent yields by the annulation of internal acetylenes by the tert-butylimines of N-substituted 3-iodoindole-2-carboxaldehydes and 2-haloindole-3-carboxaldehydes, respectively, in the presence of a palladium catalyst.
Dai Nishimura et al.
The Journal of organic chemistry, 73(7), 2496-2502 (2008-03-14)
Novel [2]rotaxanes bearing alpha-cyclodextrin (alpha-CD) derivatives and a diphenylacetylene axis molecule with trinitrobenzene as a bulky stopper have been prepared to investigate the relative rotary movement of a ring relative to an axis molecule and that of an axis molecule

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