49598-54-1

Basic information

• Product Name: dodecane, 2,2-dimethyl-
• Synonyms: 2,2-Dimethyldodecane
• CAS NO: 49598-54-1
• Molecular Formula: C₁₄H₃₀
• Molecular Weight: 198.388
• Mol File: 49598-54-1.mol

Chemical Properties

• Boiling Point: 239.089°C at 760 mmHg
• Flash Point: 95.404°C
• Density: 0.764g/cm³
• Vapor Pressure: 0.063mmHg at 25°C
• Refractive Index: 1.428
• CAS DataBase Reference: dodecane, 2,2-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: dodecane, 2,2-dimethyl-(49598-54-1)
• EPA Substance Registry System: dodecane, 2,2-dimethyl-(49598-54-1)

Safety Data

• Hazardous Substances Data: 49598-54-1(Hazardous Substances Data)

Upstream product

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Relevant articles and documents

Copper-catalyzed alkyl-alkyl cross-coupling reactions using hydrocarbon additives: Efficiency of catalyst and roles of additives

Cross-coupling of alkyl halides with alkyl Grignard reagents proceeds with extremely high TONs of up to 1230000 using a Cu/unsaturated hydrocarbon catalytic system. Alkyl fluorides, chlorides, bromides, and tosylates are all suitable electrophiles, and a TOF as high as 31200 h-1 was attained using an alkyl iodide. Side reactions of this catalytic system, i.e., reduction, dehydrohalogenation (elimination), and the homocoupling of alkyl halides, occur in the absence of additives. It appears that the reaction involves the β-hydrogen elimination of alkylcopper intermediates, giving rise to olefins and Cu-H species, and that this process triggers both side reactions and the degradation of the Cu catalyst. The formed Cu-H promotes the reduction of alkyl halides to give alkanes and Cu-X or the generation of Cu(0), probably by disproportionation, which can oxidatively add to alkyl halides to yield olefins and, in some cases, homocoupling products. Unsaturated hydrocarbon additives such as 1,3-butadiene and phenylpropyne play important roles in achieving highly efficient cross-coupling by suppressing β-hydrogen elimination, which inhibits both the degradation of the Cu catalyst and undesirable side reactions.

Copper-catalyzed cross-coupling reaction of Grignard reagents with primary-alkyl halides: Remarkable effect of 1-phenylpropyne

(Chemical Equation Presented) A general get-together: The Cu-catalyzed cross-coupling reaction of primary-alkyl halides with primary-, secondary-, and tertiary-alkyl and phenyl Grignard reagents proceeds efficiently in THF under reflux in the presence of 1-phenylpropyne (see scheme). The reaction is also applicable to alkyl mesylates (OMs) and tosylates (OTs). The reactivities of alkyl-X with a Grignard reagent increase in the order X = Cl F OMs OTs Br.