3280-08-8

Basic information

• Product Name: 2-Methyl-3-phenyl-2-butanol
• Synonyms: 2-Methyl-3-phenyl-2-butanol;α,α,β-Trimethylbenzeneethanol;α,α,β-Trimethylphenethyl alcohol
• CAS NO: 3280-08-8
• Molecular Formula: C₁₁H₁₆O
• Molecular Weight: 164.2441
• Mol File: 3280-08-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: 46°C
• Boiling Point: 251.73°C (rough estimate)
• Flash Point: 80°C
• Appearance: /
• Density: 0.9794
• Vapor Pressure: 0.24mmHg at 25°C
• Refractive Index: 1.5193
• CAS DataBase Reference: 2-Methyl-3-phenyl-2-butanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-3-phenyl-2-butanol(3280-08-8)
• EPA Substance Registry System: 2-Methyl-3-phenyl-2-butanol(3280-08-8)

Safety Data

• Hazardous Substances Data: 3280-08-8(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron, 49, p. 9535, 1993 DOI: 10.1016/S0040-4020(01)80223-4

InChI:InChI=1/C11H16O/c1-9(11(2,3)12)10-7-5-4-6-8-10/h4-9,12H,1-3H3

Upstream product

• 74-83-9 methyl bromide 
• 769-59-5 3-phenyl-butan-2-one 
• 3835-64-1 2,2-dimethyl-1-phenylpropan-1-ol 
• 21578-99-4 rac-α,β,β-trimethylstyrene oxide 
• 100-41-4 ethylbenzene 
• 769-57-3 α,β,β-trimethylstyrene 
• 100-42-5 styrene 
• 67-64-1 acetone 
• 98-85-1 1-Phenylethanol 
• 252031-74-6 tert-butyl 1-phenylethyl carbonate 
• 67-63-0 isopropyl alcohol 
• 672-65-1 (1-chloroethyl)benzene 
• 3674-77-9 2-methyl-2-phenyl-1,3-dioxolane 
• 2085-88-3 2-methyl-2-phenyloxirane 

Downstream Products

• 769-57-3 α,β,β-trimethylstyrene 
• 19643-76-6 (2-bromo-1,2-dimethyl-propyl)-benzene 
• 103859-05-8 (1,2-dimethyl-2-chloropropyl)benzene 
• 62837-59-6 1,2-dimethyl-1-phenyl-1-propanol 
• 98-86-2 acetophenone 
• 79889-30-8 C₁₉H₂₄O₂ 
• 22876-56-8 1,2-dimethyl-1-phenyl-propylamine 
• 53172-83-1 2-methyl-3-phenyl-1-butene 
• 17498-71-4 3-methyl-2-phenyl-1-butene 

Relevant articles and documents

Photocatalytic carbanion generation from C-H bonds-reductant free Barbier/Grignard-type reactions

We report a redox-neutral method for the generation of carbanions from benzylic C-H bonds in a photocatalytic Grignard-type reaction. The combination of photo- and hydrogen atom transfer (HAT) catalysis enables the abstraction of a benzylic hydrogen atom, generating a radical intermediate. This radical is reduced in situ by the organic photocatalyst to a carbanion, which is able to react with electrophiles such as aldehydes or ketones, yielding homobenzylic secondary and tertiary alcohols.

Generation of allylic and benzylic organolithium reagents from the corresponding ester, amide, carbonate, carbamate and urea derivatives

The reaction of different allylic and benzylic non-enolisable esters or amides (1), carbonates (4), carbamates (6, 7) and ureas (8) with an excess of lithium powder and a catalytic amount of naphthalene (10%) in the presence of an electrophile [(i)PrCHO, (t)BuCHO, PhCHO, Me2CO, Et2CO, (CH2)5CO, Ph2CO, Me3SiCl] in THF at different temperatures (-78, -30 or 0°C) leads, after hydrolysis with water to the corresponding allylated or benzylated products (2).

Reductive opening of 2-phenyl-1,3-dioxolanes by a naphthalene-catalysed lithiation: Synthetic applications

The reaction of 2-phenyl-1,3-dioxolanes 1a,b with an excess of lithium powder in the presence of a catalytic amount of naphthalene (4 mol %) in tetrahydrofuran at -40°C followed by successive reaction with an electrophile and final hydrolysis with water at the same temperature yields the corresponding monoprotected 1,2-diols 2aa-2bf. The same process but allowing to rise the temperature to 20°C before the hydrolysis affords alcohols 3aa-3bd. The use of 2,2-diphenyl-1,3-dioxolane 1d, under similar reaction conditions as for compounds 2, permits the isolation of 2,2-diphenylalcohols 11da-11dc, resulting from the reaction with two different electrophiles. A mechanistic rationalization for all processes is given.