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348945

Sigma-Aldrich

cis,cis-Mucononitrile

98%

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About This Item

Linear Formula:
NCCH=CHCH=CHCN
CAS Number:
1557-59-1
Molecular Weight:
104.11
MDL number:
MFCD00075424
UNSPSC Code:
12352100
PubChem Substance ID:
24861482
NACRES:
NA.22

assay

98%

mp

128-131 °C (lit.)

functional group

nitrile

SMILES string

[H]\C(C#N)=C([H])\C([H])=C(\[H])C#N

InChI

1S/C6H4N2/c7-5-3-1-2-4-6-8/h1-4H/b3-1-,4-2-

InChI key

QLQYLCRMTTXKHS-CCAGOZQPSA-N

General description

cis,cis-Mucononitrile (Z,Z-2,4-hexadienedinitrile) can be prepared by the copper-catalyzed oxidation of o-phenylenediamine. 13C MAS NMR spectra of cis,cis-mucononitrile oriented in liquid-crystalline media has been studied. Pt-catalyzed addition of diethylphosphine to cis,cis-mucononitrile yields the new diphosphine, Et2PCH(CN)CH(CH2CH2CN)PEt2.

Application

cis,cis-Mucononitrile may be used in chemical synthesis.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - 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
13816MR

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Copper-catalyzed oxidation of o-phenylenediamines to cis, cis-mucononitriles.
Kajimoto T, et al.
The Journal of Organic Chemistry, 41(8), 1389-1393 (1976)
Regiochemistry of platinum-catalyzed hydrophosphination of a diene. Formation of the chiral diphosphine Et2PCH (CN) CH (CH2CH2CN) PEt2 via monophosphine intermediates.
Kovacik I, et al.
Organometallics, 25(2), 536-539 (2006)
13C MAS NMR Spectra of cis, cis-Mucononitrile in Liquid-Crystalline Media and in the Solid State. Orientation of the Carbon Chemical-Shift Tensors.
Ramanathan KV, et al.
Journal of Magnetic Resonance, 123(2), 196-200 (1996)

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