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392413

Sigma-Aldrich

2,3-Dibenzyl-1,3-butadiene

99%

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About This Item

Linear Formula:
[C6H5CH2C(=CH2)-]2
CAS Number:
62640-74-8
Molecular Weight:
234.34
MDL number:
MFCD00191986
UNSPSC Code:
12352100
PubChem Substance ID:
24864452

assay

99%

mp

86-88 °C (dec.) (lit.)

storage temp.

2-8°C

SMILES string

C=C(Cc1ccccc1)C(=C)Cc2ccccc2

InChI

1S/C18H18/c1-15(13-17-9-5-3-6-10-17)16(2)14-18-11-7-4-8-12-18/h3-12H,1-2,13-14H2

InChI key

FNCJMHZWHWRYEO-UHFFFAOYSA-N

General description

2,3-Dibenzyl-1,3-butadiene is a disubstituted-1,3-butadiene. It participates in the synthesis of 2,3-dibenzyl-1,3-butadiene. It participates in the synthesis of η3:η1-allylalkoxynickel complex.[1]

Application

2,3-Dibenzyl-1,3-butadiene may be used in the cycloaddition reaction with donor-stabilized silylene and 1,2-diketones to form the corresponding cycloaddition products.[2] It may be used to form cyclopentenones by dienyl-Pauson-Khand reaction with suitable alkynes.[3]

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Carc. 2 - 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
04130HZ

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Bis [N, N'-diisopropylbenzamidinato (-)] silicon (II): Cycloaddition Reactions with Organic 1, 3-Dienes and 1, 2-Diketones.
Laskowski N, et al.
Organometallics, 33(21), 6141-6148 (2014)
The Diene Effect: The Design, Development, and Mechanistic Investigation of Metal-Catalyzed Diene-yne, Diene-ene, and Diene-allene [2+ 2+ 1] Cycloaddition Reactions.
Croatt MP and Wender PA.
European Journal of Organic Chemistry, 2010(1), 19-32 (2010)
Sensuke Ogoshi et al.
Journal of the American Chemical Society, 128(21), 7077-7086 (2006-05-25)
The reversible oxidative cyclization of dienes and aldehydes with nickel(0) proceeded to give eta(3):eta(1)-allylalkoxynickel complexes. The treatment of these complexes with carbon monoxide led to the formation of the corresponding lactone and/or the regeneration of a butadiene and an aldehyde

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