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344311

Sigma-Aldrich

2,5-Dimethyl-2,4-hexadiene

96%

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About This Item

Linear Formula:
(CH3)2C=CHCH=C(CH3)2
CAS Number:
764-13-6
Molecular Weight:
110.20
Beilstein/REAXYS Number:
1733342
EC Number:
212-115-5
MDL number:
MFCD00008904
UNSPSC Code:
12352100
PubChem Substance ID:
24861242
NACRES:
NA.22

vapor density

3.8 (vs air)

vapor pressure

26.9 mmHg ( 37.7 °C)
7.2 mmHg ( 20 °C)

assay

96%

form

liquid

autoignition temp.

559 °F

refractive index

n20/D 1.476 (lit.)

bp

132-134 °C (lit.)

mp

11-14 °C (lit.)

density

0.773 g/mL at 25 °C (lit.)

SMILES string

C\C(C)=C/C=C(\C)C

InChI

1S/C8H14/c1-7(2)5-6-8(3)4/h5-6H,1-4H3

InChI key

DZPCYXCBXGQBRN-UHFFFAOYSA-N

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General description

2,5-Dimethyl-2,4-hexadiene is an electron-rich alkene.[1] It induces photodechlorination of 9,10-dichloroanthracene and its mechanism has been investigated.[2] Asymmetric cyclopropanation of 2,5-dimethyl-2,4-hexadiene with tert-butyl diazoacetate catalyzed by the new copper-bisoxazoline complex has been reported.[3] 2,5-Dimethyl-2,4-hexadiene has been investigated as a singlet oxygen acceptor in various solvents.[4] Mechanism of addition reaction of aromatic and aliphatic thiols with 2,5-dimethyl-2,4-hexadiene has been investigated.[5]

Application

2,5-Dimethyl-2,4-hexadiene may be used in the synthesis of (+)-trans-(1R,3R)-chrysanthemic acid methyl ester.[6]

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

84.2 °F - closed cup

flash_point_c

29 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCK9985
MKCF6208
MKCF0110
MKCD1294
MKBZ4095V

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Katsuhiro Suenobu et al.
Journal of the American Chemical Society, 126(23), 7271-7280 (2004-06-10)
The reaction pathway and the mechanism of asymmetric induction in the synthesis of (+)-trans-(1R,3R)-chrysanthemic acid methyl ester from methyl diazoacetate and 2,5-dimethyl-2,4-hexadiene in the presence of a C(1)-chiral salicylaldimine Cu(I) complex has been probed with the aid of hybrid density
Interactions of singlet oxygen with 2, 5-dimethyl-2, 4-hexadiene in polar ano non-polar solvents evidence for a vinylog ene-reaction.
Gollnick K and Griesbeck A.
Tetrahedron, 40(17), 3235-3250 (1984)
Makoto Itagaki et al.
The Journal of organic chemistry, 70(8), 3292-3295 (2005-04-13)
Some new bisoxazoline ligands with an aryl group at the 4-position and gem-dimethyl groups at the 5-position on the oxazoline ring were prepared from arylglycines. Remarkable enhancement of the trans-selectivity (trans/cis = 87/13) and the enantioselectivity (96% ee for the
J Saltiel et al.
Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 8(6), 856-867 (2009-06-06)
Photochemical formation of 9-chloroanthracene (MCA) from 9,10-dichloroanthracene (DCA) is observed in the presence of 2,5-dimethyl-2,4-hexadiene (DMH) in acetonitrile (AN). The mechanism of the reaction was investigated using kinetics, deuterium labeling, and quenching techniques. Contrary to conclusions in a recent publication
Organic sulfur compounds. VII. Some addition and co-oxidation reactions of thiols with 2, 5-dimethyl-2, 4-hexadiene.
Oswald AA, et al.
The Journal of Organic Chemistry, 27(7), 2439-2448 (1962)
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