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42655

Sigma-Aldrich

1,6-Diphenoxy-2,4-hexadiyne

≥98.0%

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About This Item

Empirical Formula (Hill Notation):
C18H14O2
CAS Number:
30980-37-1
Molecular Weight:
262.30
Beilstein/REAXYS Number:
1979094
MDL number:
MFCD00041712
UNSPSC Code:
12352100
PubChem Substance ID:
57650124
NACRES:
NA.22

assay

≥98.0%

form

solid

SMILES string

C(Oc1ccccc1)C#CC#CCOc2ccccc2

InChI

1S/C18H14O2/c1(9-15-19-17-11-5-3-6-12-17)2-10-16-20-18-13-7-4-8-14-18/h3-8,11-14H,15-16H2

Inchi Key

ZBTRFBNXAKJTBI-UHFFFAOYSA-N

General description

1,6-Diphenoxy-2,4-hexadiyne (dimerized phenyl propargyl ether, DPPE) is a disubstituted diacetylene. It is reported to be synthesized by the oxidative coupling of phenyl propargyl ether. Its structural and spectroscopic properties have been analyzed using vibrational spectroscopy and quantum-chemical calculations. It is reported to form an organic hydrogen getter in combination with 5% Pd-CaCO3. The two crystalline forms of 1,6-diphenoxy-2,4-hexadiyne have been studied.

Application

1,6-Diphenoxy-2,4-hexadiyne may be used to synthesize the trinuclear derivative with an edge bridging ynenyl ligand on reacting with [Ru3(μ-H)(μ3-η2-apyr)(CO)9] (Hapyr=2-aminopyrimidine).

Pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
349671/1
346582/1

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M M Tauber et al.
Applied and environmental microbiology, 66(4), 1634-1638 (2000-04-01)
Rhodococcus rhodochrous NCIMB 11216 produced nitrile hydratase (320 nkat mg of protein(-1)) and amidase activity (38.4 nkat mg of protein(-1)) when grown on a medium containing propionitrile. These enzymes were able to hydrolyze nitrile groups of both granular polyacrylonitriles (PAN)
η3-Edge-Bridging versus η3-Face-Capping Coordination of a Conjugated Ynenyl Ligand on a Triruthenium Cluster Core.
Cabeza JA, et al.
Organometallics, 23(24), 5849-5855 (2004)
Vibrational and theoretical study of selected diacetylenes.
Roman M and Baranska M.
Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 115, 493-503 (2013)
Organic hydrogen getters.
Courtney RL and Harrah LA.
J. Mater. Sci., 12(1), 175-186 (1977)
Two forms of 1,6-diphenoxy-2, 4-hexadiyne and the hydrogenated analog, 1,6-diphenoxyhexane.
Morosin B and Harrah L.
Acta Crystallographica Section B, Structural Crystallography and Crystal Chemistry, 33(6), 1760-1764 (1977)
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