14255-23-3

Basic information

• Product Name: 2,4-dimethylhex-2-ene
• Synonyms: 2,4-Dimethyl-2-hexene; 2,4-Dimethylhex-2-ene; 2-hexene, 2,4-dimethyl-
• CAS NO: 14255-23-3
• Molecular Formula: C₈H₁₆
• Molecular Weight: 112.2126
• Mol File: 14255-23-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 110.6°C at 760 mmHg
• Flash Point: 6.1°C
• Density: 0.726g/cm³
• Vapor Pressure: 27.7mmHg at 25°C
• Refractive Index: 1.418
• CAS DataBase Reference: 2,4-dimethylhex-2-ene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-dimethylhex-2-ene(14255-23-3)
• EPA Substance Registry System: 2,4-dimethylhex-2-ene(14255-23-3)

Safety Data

• Hazardous Substances Data: 14255-23-3(Hazardous Substances Data)

Usage

General Description

2,4-dimethylhex-2-ene is a chemical compound with the molecular formula C8H16. It is a colorless liquid with a fruity odor, and is classified as an alkene due to its double bond between two carbon atoms. 2,4-dimethylhex-2-ene is commonly used in the production of synthetic flavors and fragrances, and can also be found as a component in industrial solvents and cleaning products. It is also used as a starting material in the synthesis of various organic compounds. The chemical is considered to have low toxicity and is not known to be a carcinogen, mutagen, or reproductive toxin. However, prolonged exposure to high concentrations of 2,4-dimethylhex-2-ene may cause irritation to the respiratory system and skin.

Upstream product

• 96-17-3 2-Methylbutyraldehyde 
• 16666-80-1 triphenylphosphonio-1-methylethanide 
• 18641-70-8 2,4-Dimethyl-3-pentanone 
• 13432-25-2 2,4-dimethyl-hexan-3-ol 
• 513-37-1 2-methylprop-1-enyl chloride 
• 101749-61-5 tri-sec-butylindium 

Relevant articles and documents

Stereochemistry in the ene reactions of singlet oxygen and triazolinediones with allylic alcohols. A mechanistic comparison

The ene reaction of singlet oxygen with (Z)-4-methylpent-3-en-2-ol- 2,5,5,5-d4 (1-OH-d4) in nonpolar solvents exhibits a 90% threo diastereoselectivity in the adduct derived from the major syn perepoxide intermediate, but also a moderate threo diastereoselectivity in the adduct derived from the minor anti perepoxide. Photooxygenation of 2,4-dimethylpent- 3-en-2-ol (2) exhibits a significant solvent dependence in the syn/anti methyl stereoselectivity, with nonpolar solvents promoting syn methyl reactivity, while polar solvents promote anti methyl reactivity. These results are in agreement with a steering effect between hydroxyl and singlet oxygen in the rate-determining step of the reaction. N-Phenyltriazolinedione addition to the chiral allylic alcohol 4-methylpent-3-en-2-ol (1-OH) is highly threo diastereoselective in nonpolar solvents, with a solvent dependent variation in the threo/erythro ene products. On the other hand, the nonfunctionalized chiral alkene 2,4-dimethyl-2-hexene (1-Et) exhibits poor diastereoselectivity. Reaction of PTAD with 1-OH-d4 in nonpolar solvents, exhibits a significant threo diastereoselectivity from the syn aziridinium imide intermediate, and a moderate threo diastereoselectivity from the anti intermediate. These results are consonant with a steering effect between the hydroxyl and the electrophile, as proposed in the case of singlet oxygen addition to allylic alcohols 1-OH and 2. In contrast to the analogous 1O2 ene reaction, a solvent independent ratio syn/anti ~50/50 was found in the addition of MTAD to 2. The intermolecular kinetic isotope effect in the reaction of 2 with MTAD (k(H)/k(D) = 1.15 ± 0.02), is consistent with formation of the intermediate in fast step, indicative that the steering effect during the formation of aziridium imide is not important in the reaction kinetics. This energetic profile is in contrast to triazolinedione addition to the secondary allylic alcohol 1-OH, where the high threo selectivity and the slight inverse kinetic isotope effect of k(H)/k(D) = 0.98 ± 0.02 are consonant with the formation of the intermediate in the rate- determining step. An explanation for the increased reactivity of the syn methyl in the addition of MTAD to 2 (~50%) is offered.