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2550-26-7

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2550-26-7 Usage

Description

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.

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

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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.

De Puy,Breitbeil

, p. 2176 (1963)

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).

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.

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.

RADICAL REACTION OF ACETONYLTRIBUTYLSTANNANE WITH α-(PHENYLSELENO)CARBONYL COMPOUNDS: A NOVEL PROCEDURE FOR PREPARATION OF 1,4-DICARBONYL COMPOUNDS

Watanabe, Yoshihiko,Yoneda, Tetsuo,Ueno, Yoshio,Toru, Takeshi

, p. 6669 - 6672 (1990)

Radical reaction of acetonyltributylstannane 1 with α-(phenylseleno)carbonyl compounds 2 gave 1,4-dicarbonyl compounds in high yield.The SH2' mechanism via the stannyl enolate in equilibrium with acetonylstannane is postulated.

Cobalt-catalyzed Divergent Markovnikov and Anti-Markovnikov Hydroamination

Zhang, Xiang-Gui,He, Zi-Xin,Guo, Peng,Chen, Zheng,Ye, Ke-Yin

supporting information, p. 22 - 26 (2022/01/04)

Catalytic hydroamination of the readily available alkenes is among the most straightforward means to construct diverse alkyl amines. To this end, the facile access to both regioselectivity, i.e., Markovnikov or anti-Markovnikov hydroamination, with minimum reaction-parameter alternation, remains challenging. Herein, we report a cobalt-catalyzed highly selective and divergent Markovnikov and anti-Markovnikov hydroamination of alkenes, in which the switch of regioselectivity is achieved simply by the variation of the addition sequence of 9-BBN.

Heterogeneous Isomerization for Stereoselective Alkyne Hydrogenation to trans-Alkene Mediated by Frustrated Hydrogen Atoms

Zhang, Weijie,Qin, Ruixuan,Fu, Gang,Zheng, Nanfeng

supporting information, p. 15882 - 15890 (2021/10/02)

Stereoselective production of alkenes from the alkyne hydrogenation plays a crucial role in the chemical industry. However, for heterogeneous metal catalysts, the olefins in cis-configuration are usually dominant in the products due to the most important and common Horiuti-Polanyi mechanism involved over the metal surface. In this work, through combined theoretical and experimental investigations, we demonstrate a novel isomerization mechanism mediated by the frustrated hydrogen atoms via the H2 dissociation at the defect on solid surface, which can lead to the switch in selectivity from the cis-configuration to trans-configuration without overhydrogenation. The defective Rh2S3 with exposing facet of (110) exhibits outstanding performance as a heterogeneous metal catalyst for stereoselective production of trans-olefins. With the frustrated hydrogen atoms at spatially separated high-valence Rh sites, the isolated hydrogen mediated cis-to-trans isomerization of olefins can be effectively conducted and the overhydrogenation can be completely inhibited. Furthermore, the bifunctional Rh-S/Pd nanosheets have been synthesized through the surface modification of Pd nanosheets with rhodium and sulfide. With the selective semihydrogenation of alkynes into cis-olefins catalyzed by the small surface PdSx ensembles, the bifunctional Rh-S/Pd nanosheets exhibit excellent activity and stereoselectivity in the one-pot alkyne hydrogenation into trans-olefin, which surpasses the most reported homogeneous and heterogeneous catalysts.

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