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344311

Sigma-Aldrich

2,5-Dimethyl-2,4-hexadiene

96%

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About This Item

Formule linéaire :
(CH3)2C=CHCH=C(CH3)2
Numéro CAS:
764-13-6
Poids moléculaire :
110.20
Numéro Beilstein :
1733342
Numéro CE :
212-115-5
Numéro MDL:
MFCD00008904
Code UNSPSC :
12352100
ID de substance PubChem :
24861242
Nomenclature NACRES :
NA.22

Densité de vapeur

3.8 (vs air)

Pression de vapeur

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

Pureté

96%

Forme

liquid

Température d'inflammation spontanée

559 °F

Indice de réfraction

n20/D 1.476 (lit.)

Point d'ébullition

132-134 °C (lit.)

Pf

11-14 °C (lit.)

Densité

0.773 g/mL at 25 °C (lit.)

Chaîne SMILES 

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

InChI

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

Clé InChI

DZPCYXCBXGQBRN-UHFFFAOYSA-N

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Description générale

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

Application

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

Pictogrammes

FlameExclamation mark
GHS02,GHS07

Mention d'avertissement

Warning

Mentions de danger

H226,H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

84.2 °F - closed cup

Point d'éclair (°C)

29 °C - closed cup

Équipement de protection individuelle

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

Certificats d'analyse (COA)

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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
Maki Ohashi et al.
Organic letters, 10(13), 2741-2743 (2008-06-10)
The synthesis of monoalkylated propanedinitriles was achieved upon photoirradiation of MeCN/H(2)O solutions containing propanedinitrile (1; malononitrile) and electron-rich alkenes in the presence of lithium carbonate and a catalytic amount of 9-cyanophenanthrene or redox-type photosensitizers (electron-mediating photosensitizers), through regioselective anti-Markovnikov photochemical
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)
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
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