85924-68-1

Basic information

• Product Name: Benzenemethanol, a-3-butenyl-a-methyl-
• CAS NO: 85924-68-1
• Molecular Formula: C12H16O
• Molecular Weight: 176.258
• Mol File: 85924-68-1.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: Benzenemethanol, a-3-butenyl-a-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanol, a-3-butenyl-a-methyl-(85924-68-1)
• EPA Substance Registry System: Benzenemethanol, a-3-butenyl-a-methyl-(85924-68-1)

Safety Data

• Hazardous Substances Data: 85924-68-1(Hazardous Substances Data)

Upstream product

• 109-49-9 5-Hexen-2-one 
• 7051-34-5 cyclopropylcarbinyl bromide 
• 98-86-2 acetophenone 
• 100-58-3 phenylmagnesium bromide 
• 75-62-7 Bromotrichloromethane 
• 1293965-65-7 3-(1-methyl-1-phenylpent-4-en-1-oxy)-5-(4-methoxyphenyl)-4-methylthiazole-2(3H)-thione 
• 5911-08-0 chloro(cyclopropyl)methane 
• 5162-44-7 1-bromo-4-butene 

Downstream Products

• 1293965-65-7 3-(1-methyl-1-phenylpent-4-en-1-oxy)-5-(4-methoxyphenyl)-4-methylthiazole-2(3H)-thione 
• 1293965-62-4 2-((1-methyl-1-phenylpent-4-en-2-yl)sulfanyl)-5-(4-methoxyphenyl)-4-methylthiazole N-oxide 
• 1619258-76-2 1-methyl-3-(2-phenylhex-5-en-2-yl)indole 
• 1619258-78-4 butyl(2-phenylhex-5-en-2-yl)sulfide 
• 1353653-28-7 C₁₆H₂₀O₃ 
• 1353653-24-3 C₁₆H₂₂O₂ 
• 1353653-27-6 C₁₄H₁₈O₂ 
• 1353653-32-3 C₁₄H₁₈O 
• 1353653-31-2 C₁₄H₁₈O 

Relevant articles and documents

Organocatalytic synthesis of polysubstituted tetrahydrofurans from alkenes

A novel, organocatalytic and environmentally friendly protocol for the synthesis of polysubstituted tetrahydrofurans from trivial starting materials has been described. By employing 2,2,2-trifluoroacetophenone-mediated oxidation, which utilizes H2O2 as a green oxidant, we introduce a sustainable procedure that embraces the principles of green chemistry for the production of substituted tetrahydrofurans in high to excellent yields and tolerates a wide range of substitution patterns.

Tertiary alkoxyl radicals from 3-alkoxythiazole-2(3H)-thiones

This study deals with the synthesis of tert-O-alkyl thiohydroxamates and their use as tert-alkoxyl radical precursors. tert-Alkoxyl radicals were applied in mechanistic studies to determine rate constants of (i) p-chlorocumyloxyl radical addition to bicyclo[2.2.1]heptene (k=1×107 M -1 s-1), (ii) 2-phenylhex-5-en-2-oxyl radical 5-exo-trig-cyclization (kcis=3×109 s-1, ktrans=1×109 s-1), and (iii) 2-methyl-5-phenylpent-2-oxyl to 2-hydroxy-2-methyl-5-phenylpent-5-yl radical isomerization (1,5-H-atom shift; k=0.4-1.5×108 s-1). The reactions pose key steps in synthesis of 2,2,5-substituted tetrahydrofurans and 2-bromo-3-alkoxybicyclo[2.2.1]heptanes. Stereoselectivity in 5-exo-trig cyclization (2,5-cis) and intermolecular addition (exo/endo>99:1), originates from torsional strain in transition structures of alkoxyl radical reactions.

Easy selective generation of (lithiomethyl)cyclopropane or homoallyllithium by a chlorine-lithium exchange

The reaction of (chloromethyl)cyclopropane 5 with lithium and a catalytic amount of DTBB (5 mol %) in the presence of different carbonyl compounds [Et2CO, n-Pr2CO, (c-C3H5)2CO, (CH2)5CO, PhCOMe, t-BuCHO, i-PrCHO, PhCHO] as electrophiles in THF at -78 °C leads, after hydrolysis with water, to the corresponding cyclopropyl alcohols 6. However, when the same starting material is lithiated using naphthalene as the arene catalyst in ether at 0 °C and then reacts with the same series of electrophiles, the final hydrolysis with water yields the corresponding unsaturated alcohols 7.