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Benzylacetone, also known as 4-phenyl-2-butanone, is a volatile aromatic ketone that serves as a fragrance compound. It is a clear colorless to pale yellowish liquid with a sweet-floral smell. Benzylacetone can be synthesized through the selective hydrogenation of benzylidene acetone, which is derived from benzaldehyde and acetone.

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  • 2550-26-7 Structure
  • Basic information

    1. Product Name: Benzylacetone
    2. Synonyms: METHYL PHENETHYL KETONE;METHYL 2-PHENYLETHYL KETONE;BENZYLACETONE;4-Phenylbutan-2-one;4-PHENYL-2-BUTANONE;1-Phenyl-3-butanone;2-Butanone, 4-phenyl-;4-Phenyl-2-butanoine
    3. CAS NO:2550-26-7
    4. Molecular Formula: C10H12O
    5. Molecular Weight: 148.2
    6. EINECS: 219-847-4
    7. Product Categories: Pharmaceutical Intermediates
    8. Mol File: 2550-26-7.mol
  • Chemical Properties

    1. Melting Point: -13°C
    2. Boiling Point: 235 °C(lit.)
    3. Flash Point: 209 °F
    4. Appearance: Clear colorless to pale yellow/Liquid
    5. Density: 0.989 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 0.0557mmHg at 25°C
    7. Refractive Index: n20/D 1.512(lit.)
    8. Storage Temp.: Store below +30°C.
    9. Solubility: Chloroform, Methanol
    10. Water Solubility: PRACTICALLY INSOLUBLE
    11. BRN: 1907123
    12. CAS DataBase Reference: Benzylacetone(CAS DataBase Reference)
    13. NIST Chemistry Reference: Benzylacetone(2550-26-7)
    14. EPA Substance Registry System: Benzylacetone(2550-26-7)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 38
    3. Safety Statements: 37-24/25
    4. WGK Germany: 1
    5. RTECS: EL9600000
    6. TSCA: Yes
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 2550-26-7(Hazardous Substances Data)

2550-26-7 Usage

Uses

Used in Floral Attraction:
Benzylacetone is used as an attractant compound in the flower Nicotiana attenuata, drawing pollinators to the plant and facilitating the process of pollination.
Used in Pest Control:
It is employed as an attractant for melon flies, helping in the management and control of these pests in agricultural settings.
Used in Soap Perfumery:
Benzylacetone is used as an odorant in the soap industry, adding a pleasant fragrance to the products and enhancing the sensory experience for consumers.
Used in Flavor and Fragrance Industry:
It has been identified as a volatile component of cocoa and is used in the preparation of 4-oxocyclohexanecarbaldehyde derivatives, which are important for creating various flavors and fragrances.
Used in Analytical Chemistry:
Benzylacetone may be used as an analytical standard for the determination of the analyte in volatile oils, agarwood extracts of Aquilaria malaccensis, yeast cell culture, and biological samples through various chromatography-based techniques. This application aids in the accurate identification and quantification of target compounds in these complex mixtures.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 38, p. 2097, 1990 DOI: 10.1248/cpb.38.2097Tetrahedron Letters, 25, p. 5467, 1984 DOI: 10.1016/S0040-4039(01)81600-2

Safety Profile

Moderately toxic by ingestion and intraperitoneal routes. An eye and severe skin irritant. Flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

Check Digit Verification of cas no

The CAS Registry Mumber 2550-26-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,5,5 and 0 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 2550-26:
(6*2)+(5*5)+(4*5)+(3*0)+(2*2)+(1*6)=67
67 % 10 = 7
So 2550-26-7 is a valid CAS Registry Number.
InChI:InChI=1/C10H12O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3

2550-26-7 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Alfa Aesar

  • (B22777)  4-Phenyl-2-butanone, 98%   

  • 2550-26-7

  • 250g

  • 586.0CNY

  • Detail
  • Alfa Aesar

  • (B22777)  4-Phenyl-2-butanone, 98%   

  • 2550-26-7

  • 1000g

  • 925.0CNY

  • Detail

2550-26-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-phenylbutan-2-one

1.2 Other means of identification

Product number -
Other names Phenethyl methyl ketone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2550-26-7 SDS

2550-26-7Relevant articles and documents

Hydrogenation of α,β-Unsaturated Carbonyl Compounds by Carbon monoxide and Water with Rh6(CO)16 Catalyst under Mild Conditions

Joh, Takashi,Fujiwara, Keisuke,Takahashi, Shigetoshi

, p. 978 - 980 (1993)

By controlling such factors as the concentration of water and amine, the carbon-carbon double bond of α,β-unsaturated carbonyl compounds could be selectively hydrogenated under mild water-gas shift reaction (WGSR) conditions using a Rh6(CO)16-Et3N catalys

Diastereoselective dl-Hydrocoupling of Benzalacetones by Electroreduction

Kise, Naoki,Kitagishi, Yasuo,Ueda, Nasuo

, p. 959 - 963 (2004)

Electroreduction of benzalacetones with an undivided cell in Et 4NOTs/acetonitrile gave cyclized dl-hydrodimers as mixtures of two diastereomers. The hydrodimerization proceeded stereoselectively to afford linear dl-hydrodimers, and the following cyclization led to two thermodynamically stable diasteromers of cyclopentanols.

Liquid-Phase Regioselective 1,4-Hydrogenation of Benzylidene Ketones on Rh/AIPO4 Catalysts

Cabello, J. A.,Campelo, J. M.,Garcia, A.,Luna, D.,Marinas, J. M.

, p. 1786 - 1790 (1986)

The liquid-phase catalytic hydrogenation of α,β-unsaturated carbonyl compounds, in the p-XC6H4CH=CHCOR form (E isomers; X = H, Me, MeO, Cl; R = Me, Et, n-Pr, i-Pr, n-Bu, t-Bu, n-Pe, Ph) was carried out by using a rhodium catalyst supported at 1 wt percent

Carbonyl regeneration from oximes and semicarbazones by trimethylchlorosilane-dimethylsulphoxide

Ghelfi,Grandi,Pagnoni

, p. 2279 - 2284 (1993)

Treatment of oximes and semicarbazones of saturated and α,β-unsaturated ketones and aldehydes with trimethylchlorosilane-dimethyl sulphoxide in dry acetonitrile affords the corresponding carbonyl compounds in excellent yields under mild conditions.

Enzyme-catalysed enantioselective oxidation of alcohols by air exploiting fast electrochemical nicotinamide cycling in electrode nanopores

Wan, Lei,Heath, Rachel S.,Siritanaratkul, Bhavin,Megarity, Clare F.,Sills, Adam J.,Thompson, Matthew P.,Turner, Nicholas J.,Armstrong, Fraser A.

, p. 4958 - 4963 (2019)

Enantioselective conversion of alcohols to ketones using air as the oxidant is achieved with high rates and efficiency using an indium tin oxide (ITO) electrode in which an alcohol dehydrogenase and a photosynthetic NADPH recycling enzyme are confined within nanopores. The massive catalytic enhancement arising from nanoconfinement is exploited in an air-driven electrochemical cell, which requires no complicating control features yet allows continuous monitoring of the reaction via the current that flows between anode (ITO: Organic chemistry) and cathode (Pt: O2 from air).

Carbonyl regeneration from p-toluensulfonhylhydrazones by trimethylchlorosilane-dimethylsulfoxide

Ghelfi,Grandi,Pagnoni

, p. 1845 - 1850 (1992)

Treatment of p-tosylhydrazones of saturated and α,β-unsaturated ketones and aldehydes with trimethylchlorosilane-dimethyl sulphoxide in dry acetonitrile affords the corresponding carbonyl compounds in excellent yields under mild conditions.

TRANSFER HYDROGENATION BETWEEN ALCOHOLS AND α,β UNSATURATED KETONES WITH RhH(PPh3)3 AS CATALYST. EVIDENCE FOR REGIOSPECIFICITY AND AN UNUSUAL RATE-LIMITING STEP

Beaupere, D.,Bauer, P.,Nadjo, L.,Uzan, R.

, p. C12 - C14 (1982)

In the hydrogen transfer between an alcohol and an α,β-unsaturated ketone with RhH(PPh3)4 as catalyst under mild conditions the breaking of the O-H bond is, unusually, the rate-determining step, and the hydroxylic hydrogen is selectively transferred to the α-carbon of the ketone.

Syntheses of water-soluble octahedral, truncated octahedral, and cubic Pt-Ni nanocrystals and their structure-activity study in model hydrogenation reactions

Wu, Yuen,Cai, Shuangfei,Wang, Dingsheng,He, Wei,Li, Yadong

, p. 8975 - 8981 (2012)

We developed a facile strategy to synthesize a series of water-soluble Pt, PtxNi1-x (0 xNi1-x nanocrystals were effectively controlled by choice of ratios between the Pt and Ni precursors. In a preliminary study to probe their structure-activity dependence, we found that the shapes, compositions, and capping agents strongly influence the catalyst performances in three model heterogeneous hydrogenation reactions.

Homo-coupling reactions of alkenyl- and arylfluorosilanes mediated by a copper(I) salt

Nishihara, Yasushi,Ikegashira, Kazutaka,Toriyama, Fumihiko,Mori, Atsunori,Hiyama, Tamejiro

, p. 985 - 990 (2000)

Homo-coupling reactions of an alkenyl- or arylsilane readily occur with a copper(I) salt in an aprotic polar solvent such as N, N-dimethylformamide or dimethyl sulfoxide under an aerobic condition to give the corresponding conjugated dienes or biaryls, respectively. Optimization of a copper salt and a solvent for the homo-coupling reaction is discussed. The formation of the organocopper intermediates is evidenced by trapping experiments with iodine and by a conjugate addition to methyl vinyl ketone.

Selective oxidation of alcohols with hydrogen peroxide catalyzed by tungstate ions (WO4=) supported on periodic mesoporous organosilica with imidazolium frameworks (PMO-IL)

Karimi, Babak,Rostami, Fatemeh Bakhshandeh,Khorasani, Mojtaba,Elhamifar, Dawood,Vali, Hojatollah

, p. 6114 - 6119 (2014)

Tungstate ions supported on the periodic mesoporous organosilica with ionic liquid frameworks (WO4=@PMO-IL) were found to be a recoverable catalyst system for the highly selective oxidation of various primary or secondary alcohols to the corresponding aldehydes or ketones by 30% H2O2as green oxidant under neutral aqueous reaction conditions. The catalyst can be also recovered and efficiently reused in seven subsequent reaction cycles without any remarkable decreasing in the catalyst activity and selectivity. Moreover, N2sorption analysis, transmission electron microscopy (TEM) images, and thermal gravimetric analysis (TGA) showed that the structure regularity and functional groups loaded of the catalyst were not affected during the reaction process.

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