4-Methyl-1-phenylpentan-2-one

Base Information

• Chemical Name: 4-Methyl-1-phenylpentan-2-one
• CAS No.: 5349-62-2
• Molecular Formula: C12H16O
• Molecular Weight: 176.258
• Hs Code.: 2914399090
• European Community (EC) Number: 226-316-0
• NSC Number: 1268
• UNII: 2Z1A62342T
• DSSTox Substance ID: DTXSID1063805
• Nikkaji Number: J217.917B
• Wikidata: Q27255819
• Metabolomics Workbench ID: 44960
• Mol file: 5349-62-2.mol

Synonyms:4-Methyl-1-phenylpentan-2-one;4-Methyl-1-phenyl-2-pentanone;5349-62-2;Benzyl isobutyl ketone;Isobutyl benzyl ketone;2-Pentanone, 4-methyl-1-phenyl-;spicy pentanone;FEMA No. 2740;UNII-2Z1A62342T;NSC 1268;NSC-1268;EINECS 226-316-0;2Z1A62342T;AI3-11065;4-methyl-1-phenyl-pentan-2-one;Isopropylphenylacetone;SCHEMBL106992;DTXSID1063805;DTYGTEGDVPAKDA-UHFFFAOYSA-;FEMA 2740;NSC1268;CHEBI:169560;MFCD00015639;AKOS010016656;CS-W022210;DS-3984;HY-W041470;FT-0658153;4-METHYL-1-PHENYL-2-PENTANONE [FHFI];4-Methyl-1-phenyl-2-pentanone, >=95%, FG;D71255;A829628;W-105731;Q27255819

Chemical Property of 4-Methyl-1-phenylpentan-2-one

Chemical Property:

• Vapor Pressure: 0.0198mmHg at 25°C
• Refractive Index: n20/D 1.498(lit.)
• Boiling Point: 252 °C at 760 mmHg
• Flash Point: 98.2 °C
• PSA: 17.07000
• Density: 0.948 g/cm³
• LogP: 2.84430
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 176.120115130
• Heavy Atom Count: 13
• Complexity: 155

Purity/Quality:

99% ^*data from raw suppliers

4-Methyl-1-phenyl-2-pentanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CC(=O)CC1=CC=CC=C1
• Description: 4-Methyl-l-phenyl-2-pentanone has a sweet, woody, spicy odor. At low levels, it has a sweet and tart, fruity flavor. Prepared by passing phenylacetic acid and isovaleric acid over Th02 catalyst at 450 - 470°C.
• Uses: Flavoring. 4-Methyl-1-phenyl-2-pentanone is a volatile flavor and fragrance agent used as a food additive, which gives rise to a woody odour and a sweet/fruity/spicy taste.

Technology Process of 4-Methyl-1-phenylpentan-2-one

There total 7 articles about 4-Methyl-1-phenylpentan-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

phenyldiazomethane (908094-04-2) + isovaleraldehyde (590-86-3) → 4-Methyl-1-phenyl-2-pentanone (5349-62-2)

Guidance literature:

With lithium bromide; In diethyl ether; at -5 - 0 ℃; protected from light;

DOI:10.1021/jo00171a056

Reference yield:

N-benzyl-2,4,6-triphenylpyridinium tetrafluoroborate (66310-10-9) + isovaleraldehyde (590-86-3) → 4-Methyl-1-phenyl-2-pentanone (5349-62-2)

Guidance literature:

N-benzyl-2,4,6-triphenylpyridinium tetrafluoroborate; With potassium phosphate; (1,2-dimethoxyethane)dichloronickel(II); tetrakis(tetrabutylammonium)decatungstate(VI); 4,4'-di-tert-butyl-2,2'-bipyridine; In acetonitrile; at 25 ℃; for 0.166667h; Inert atmosphere;

isovaleraldehyde; In acetonitrile; at 25 ℃; for 15h; regioselective reaction; Inert atmosphere; Irradiation;

DOI:10.1021/acs.orglett.1c01716

Reference yield:

benzylamine (100-46-9) → 4-Methyl-1-phenyl-2-pentanone (5349-62-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ethanol / 4 h / 100 °C

2.1: (1,2-dimethoxyethane)dichloronickel(II); tetrakis(tetrabutylammonium)decatungstate(VI); 4,4'-di-tert-butyl-2,2'-bipyridine; potassium phosphate / acetonitrile / 0.17 h / 25 °C / Inert atmosphere

2.2: 15 h / 25 °C / Inert atmosphere; Irradiation

With potassium phosphate; (1,2-dimethoxyethane)dichloronickel(II); tetrakis(tetrabutylammonium)decatungstate(VI); 4,4'-di-tert-butyl-2,2'-bipyridine; In ethanol; acetonitrile;

DOI:10.1021/acs.orglett.1c01716

upstream raw materials:

3-methylbutyric acid

phenylacetic acid

phenyldiazomethane

isovaleraldehyde

Downstream raw materials:

(4-methylpentyl)cyclohexane

1-cyclohexyl-4-methylpentan-2-ol

(S)-4-methyl-1-phenyl-2-pentanol

(±)-4-methyl-1-phenyl-2-pentanol

Refernces

• 1、 Loeschorn, Carol A.,Nakajima, Masayuki,McCloskey, Patrick J.,Anselme, Jean-Pierre. "Lithium Bromide Catalyzed Homologation of Aldehydes with Aryldiazomethanes". . p. 4407 - 4410. Retrieved 2007/10/02.