5857-68-1

Basic information

• Product Name: 2-(tert-Butyl)-3,3-dimethyl-1-butene
• Synonyms: 2-(tert-Butyl)-3,3-dimethyl-1-butene
• CAS NO: 5857-68-1
• Molecular Formula: C₁₀H₂₀
• Molecular Weight: 140.27
• Mol File: 5857-68-1.mol

Chemical Properties

• Boiling Point: 146.1°C at 760 mmHg
• Flash Point: 28.3°C
• Appearance: /
• Density: 0.743g/cm³
• Vapor Pressure: 5.96mmHg at 25°C
• Refractive Index: 1.421
• CAS DataBase Reference: 2-(tert-Butyl)-3,3-dimethyl-1-butene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(tert-Butyl)-3,3-dimethyl-1-butene(5857-68-1)
• EPA Substance Registry System: 2-(tert-Butyl)-3,3-dimethyl-1-butene(5857-68-1)

Safety Data

• Hazardous Substances Data: 5857-68-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H20/c1-8(9(2,3)4)10(5,6)7/h1H2,2-7H3

Upstream product

• 815-24-7 Di-t-butyl ketone 
• 59983-62-9 Li{(CH₂)(CH₂)P(C₆H₅)2} 

Downstream Products

• 563-79-1 2,3-Dimethyl-2-butene 
• 558-37-2 tert-butylethylene 
• 563-78-0 2,3-Dimethyl-1-butene 
• 115-11-7 isobutene 
• 50-00-0 formaldehyd 
• 815-24-7 Di-t-butyl ketone 
• 7499-68-5 Di-tert.-butyl-essigsaeure-amid 
• 41785-81-3 2-tert-Butyl-3,3-dimethylbutanoic acid 
• 41979-14-0 2,2-di-tert-butyloxirane 
• 16747-45-8 2,2,3,4,4-pentamethylpentane 
• 692-47-7 (Z)-2,2,5,5-tetramethyl-3-hexene 
• 692-48-8 (E)-2,2,5,5-tetramethylhex-3-ene 
• 79802-53-2 1,1-dimethyl-2-(1,1-dimethylethyl)cyclobutane 
• 79802-54-3 2,2,3,4,4-pentamethyl-3-(hydroxymethyl)pentane 

Relevant articles and documents

Formation of carbenoid intermediates in the reaction of ditertiobutyl ketone with low-valent titanium reagents

Treatment of tBu2CO with TiCl4 and Li(Hg) in THF gave the hydrocarbon tBu2CH2 as the major product (40% yield); 60% of the total quantity of tBu2CH2 was lib

Reactions of aliphatic ketones R2CO (R = Me, Et, iPr, and tBu) with the MCl4/Li(Hg) system (M = U or Ti): Mechanistic analogies between the McMurry, Wittig, and Clemmensen reactions

Analysis of the products of the reactions of ketones R2CO (R = Me, Et, iPr, tBu) with the MCl4/Li(Hg) system (M = U, Ti) at 20°C revealed significant differences. For R = Me, the reaction proceeded exclusively (M = U) or preferentially (M = Ti) via a metallopinacol intermediate resulting from dimerization of ketyl radicals. Pinacol was liberated by hydrolysis, and tetramethylethylene was obtained after further reduction at 65°C. For R = iPr, formation of iPr2C=CiPr2 as the only coupling product, the nonproduction of this alkene by reduction of the uranium pinacolate [U]-OCR2CR2O-[U] (R = iPr) at 20°C, and the instability of the corresponding titanium pinacolate towards rupture of the pinacolic C-C bond indicated that reductive coupling of iPr2CO did not proceed by dimerization of ketyl radicals. Formation of 2,4-dimethyl-2-pentene was in favor of a carbenoid intermediate resulting from deoxygenative reduction of the ketyl. These results revealed that for sterically hindered ketones, McMurry reactions can be viewed as Wittig-like olefination reactions. For R = tBu, no coupling product was obtained and the alkane tBu2CH2 was the major product. The involvement of the carbenoid species [M]=CtBu2 was confirmed by its trapping with H2O, leading to tBu2CH2, and with the aldehydes RCHO, giving the cross-coupling products tBu2C=C(R)H (R = Me, tBu). Therefore, in the case of severely congested ketones, McMurry reactions present strong similarities to the Clemmensen reduction of ketones, owing to the involvement in both reactions of carbenoid species which exhibit similar reactivity. Wiley-VCH Verlag GmbH, 2001.

Reactivity of phosphonium diylids with aldehydes and ketones

Non-stabilized and semi-stabilized phosphonium diylids of the type (C6H5)2P(CHR)(CHLiR) (5) show a greater nucleophilic reactivity toward carbonyl compounds than the corresponding monoylids (C6H5)2P(CHR)(CH2R) (8).Thus diylid 5a reacts readily at room temperature with sterically hindered ketones such as fenchone or di-t-butylketone.However, the residual negative charge in the intermediate adduct 13 slows the decomposition to Wittig products and is probably responsible for the observed changes (generally enhancement) in the E-selectivity in the case of non-stabilized as well as semi-stabilized ylids.