5398-04-9

Basic information

• Product Name: 2-(4-methylphenyl)butan-2-ol
• CAS NO: 5398-04-9
• Molecular Formula: C₁₁H₁₆O
• Molecular Weight: 164.2441
• Mol File: 5398-04-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 220.1°C at 760 mmHg
• Flash Point: 104.8°C
• Density: 0.966g/cm³
• Vapor Pressure: 0.0667mmHg at 25°C
• Refractive Index: 1.512
• CAS DataBase Reference: 2-(4-methylphenyl)butan-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-methylphenyl)butan-2-ol(5398-04-9)
• EPA Substance Registry System: 2-(4-methylphenyl)butan-2-ol(5398-04-9)

Safety Data

• Hazardous Substances Data: 5398-04-9(Hazardous Substances Data)

Usage

General Description

2-(4-methylphenyl)butan-2-ol, also known as p-methylphenyl-2-butanol, is a chemical compound with the formula C11H16O. It is a colorless liquid that is slightly soluble in water and is commonly used as a fragrance ingredient in perfumes and personal care products. 2-(4-methylphenyl)butan-2-ol is derived from the benzene ring and contains a butanol group, making it both aromatic and aliphatic in nature. It has a sweet, floral odor and is often used to add a sense of warmth and richness to fragrances. The compound is also used in the synthesis of pharmaceuticals and other organic compounds due to its unique chemical structure. Additionally, 2-(4-methylphenyl)butan-2-ol can act as a chiral ligand in catalytic asymmetric synthesis.

Upstream product

• 4294-57-9 para-methylphenylmagnesium bromide 
• 78-93-3 butanone 
• 925-90-6 ethylmagnesium bromide 
• 122-00-9 para-methylacetophenone 
• 1595-16-0 1-sec-butyl-4-methylbenzene 
• 155006-09-0 1-(1-chloro-1-methyl-propyl)-4-methyl-benzene 
• 10467-10-4 ethylmagnesium iodide 

Downstream Products

• 81676-11-1 α,β,p-trimethylstyrene 
• 155006-09-0 1-(1-chloro-1-methyl-propyl)-4-methyl-benzene 
• 59970-06-8 (Z)-1-(but-2-en-2-yl)-4-methylbenzene 
• 34815-65-1 (E)-1-(but-2-en-2-yl)-4-methylbenzene 
• 847057-41-4 2-(4-methylphenyl)-2-butoxyl radical 

Relevant articles and documents

Harnessing the Power of the Asymmetric Grignard Synthesis of Tertiary Alcohols: Ligand Development and Improved Scope Exemplified by One-Step Gossonorol Synthesis

A series of N-substituted cyclohexyldiaminophenolic ligands for the asymmetric Grignard synthesis of tertiary alcohols is reported. The 2,5-dimethylpyrrole-decorated ligand led to improved enantioselectivities and broadened the scope of the methodology. As an exemplar, we report an unprecedented highly selective one-step synthesis of gossonorol in 93% ee, also constituting the shortest formal syntheses of natural products boivinianin B and yingzhaosu C.

Vilsmeier-Haack reaction of tertiary alcohols: Formation of functionalised pyridines and naphthyridines

Vilsmeier-Haack reaction of 2-arylpropan-2-ols proceeds with multiple iminoalkylations leading to the formation of conjugated iminium salts which on ammonium acetate-induced cyclisation afford 4-arylnicotinaldehydes in good yields. Tertiary alcohols derived from aliphatic or alicyclic ketones by the addition of methyl Grignard are converted into substituted pyridines and naphthyridines by the action of Vilsmeier's reagent in N,N-dimethylformamide followed by nucleophile-assisted cyclisation in the presence of ammonium acetate.

Studies on the Regioselectivities in the Oxidation of Simple Alkyl Aromatic Hydrocarbons by Molecular Oxygen

The products of the autoxidation of various simple alkyl aromatic hydrocarbons were reduced by LiAlH4, and the alcohols formed were determined by gas chromatography.In the cases of 2-phenylbutane, 3-phenylpentane, and 2-p-tolylbutane a considerable fragmentation of the intermediate tertiary alkoxy radicals was proved.On the basis of the analytical results relative reaction rates of the various C-H bonds in the hydrocarbons studied were calculated.It is shown that the attack at C-H bonds which are not activated by the aromatic nucleus cannot be neglected and may be of great importance for the kinetics of the oxidation of alkyl aromatic hydrocarbons.