7779-78-4

Basic information

• Product Name: 4-METHYL-1-PHENYL-2-PENTANOL
• Synonyms: .alpha.-(2-methylpropyl)-Benzeneethanol;4-methyl-1-phenylpentan-2-ol;alpha-(2-methylpropyl)-benzeneethano;alpha-(2-methylpropyl)benzeneethanol;alpha-isobutyl-phenethylalcoho;Benzeneethanol, alpha-(2-methylpropyl)-;ISOBUTYL BENZYL CARBINOL;FEMA 2208
• CAS NO: 7779-78-4
• Molecular Formula: C₁₂H₁₈O
• Molecular Weight: 178.27
• EINECS: 231-939-6
• Mol File: 7779-78-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 123 °C / 11mmHg
• Flash Point: 110 °C
• Appearance: /
• Density: 0.95
• Vapor Pressure: 0.224mmHg at 25°C
• Refractive Index: 1.5030 to 1.5070
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-METHYL-1-PHENYL-2-PENTANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHYL-1-PHENYL-2-PENTANOL(7779-78-4)
• EPA Substance Registry System: 4-METHYL-1-PHENYL-2-PENTANOL(7779-78-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36-52/53
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: DA0513300
• Hazardous Substances Data: 7779-78-4(Hazardous Substances Data)

Usage

Description

4-METHYL-1-PHENYL-2-PENTANOL, also known as α-Isobutylphenethyl alcohol, is an organic compound with a green, floral, somewhat herbaceous odor and a buttery, oily, caramellic flavor. It can be synthesized by reacting isobutyl aldehyde with benzyl magnesium chloride.

Uses

Used in Flavor Industry:
4-METHYL-1-PHENYL-2-PENTANOL is used as a flavoring agent for its buttery, oily, caramellic flavor, adding depth and complexity to various food and beverage products.
Used in Fragrance Industry:
4-METHYL-1-PHENYL-2-PENTANOL is used as a fragrance ingredient for its green, floral, and herbaceous scent, contributing to the creation of various perfumes, colognes, and other scented products.
Used in Chemical Synthesis:
4-METHYL-1-PHENYL-2-PENTANOL can be used as a starting material or intermediate in the synthesis of other organic compounds, such as pharmaceuticals, agrochemicals, or specialty chemicals, due to its unique structure and functional groups.

Preparation

By reacting isobutyl aldehyde with benzyl magnesium chloride.

Biochem/physiol Actions

Taste at 10 ppm

Synthesis

4-Methyl-1-phenyl-2-pentanol is prepared from benzyl chloride to benzyl magnesium bromide, and then hydrolyzed with isovaleraldehyde after Grignard reaction.

InChI:InChI=1/C12H18O/c1-10(2)8-12(13)9-11-6-4-3-5-7-11/h3-7,10,12-13H,8-9H2,1-2H3

Upstream product

• 122-78-1 phenylacetaldehyde 
• 100-44-7 benzyl chloride 
• 590-86-3 isovaleraldehyde 
• 770-09-2 benzyltrimethylsilane 
• 5349-62-2 4-Methyl-1-phenyl-2-pentanone 
• 103-82-2 phenylacetic acid 
• 65473-82-7 2-isobutyl-3-phenyloxirane 
• 54624-34-9 (4-methylpent-1-en-1-yl)benzene 
• 66310-10-9 N-benzyl-2,4,6-triphenylpyridinium tetrafluoroborate 
• 100-46-9 benzylamine 

Relevant articles and documents

C-H Alkylation of Aldehydes by Merging TBADT Hydrogen Atom Transfer with Nickel Catalysis

Catalyst controlled site-selective C-H functionalization is a challenging but powerful tool in organic synthesis. Polarity-matched and sterically controlled hydrogen atom transfer (HAT) provides an excellent opportunity for site-selective functionalization. As such, the dual Ni/photoredox system was successfully employed to generate acyl radicals from aldehydes via selective formyl C-H activation and subsequently cross-coupled to generate ketones, a ubiquitous structural motif present in the vast majority of natural and bioactive molecules. However, only a handful of examples that are constrained to the use of aryl halides are developed. Given the wide availability of amines, we developed a cross-coupling reaction via C-N bond cleavage using the economic nickel and TBADT catalyst for the first time. A range of alkyl and aryl aldehydes were cross-coupled with benzylic and allylic pyridinium salts to afford ketones with a broad spectrum of functional group tolerance. High regioselectivity toward formyl C-H bonds even in the presence of α-methylene carbonyl or α-amino/oxy methylene was obtained.

Photocatalytic carbanion generation-benzylation of aliphatic aldehydes to secondary alcohols

We present a redox-neutral method for the photocatalytic generation of carbanions. Benzylic carboxylates are photooxidized by single electron transfer; immediate CO2 extrusion and reduction of the in situ formed radical yields a carbanion capable of reacting with aliphatic aldehydes as electrophiles giving the Grignard analogous reaction product.

Le benzyltrimethylsilane, un agent pratique de benzylation

In the presence of Bu4N(1+))*F(1-), benzyltrimethylsilane behaves as a convenient benzylation reagent.In the reaction with non conjugated aldehydes, pehenethylalcohols are obtained in satisfactory yields upon hydrolysis, while the formation of bibenzyl or ortho products are not observed.When the reaction occurs with α,β-unsaturated aldehydes and ketones, only 1,2-addition is observed even in the case of chalcone.