2689-63-6

Basic information

• Product Name: (ALPHA-METHYLPHENACYL)TRIPHENYLPHOSPHONIUM BROMIDE
• Synonyms: (ALPHA-METHYLPHENACYL)TRIPHENYLPHOSPHONIUM BROMIDE;alpha-(Triphenylphosphonio)propiophenone bromide;(1-methyl-2-oxo-2-phenylethyl)triphenylphosphonium bromide;(1-benzoylethyl)triphenylphosphonium bromide;(à-methylphenacyl)triphenylphosphonium bromide;2-(triphenylphosphonio)propiophenone bromide;α-Methylphenacyl)TriphenylphosphoniumBromide;2-(TRIPHENYLPHOSPHONIO)PROPIOPHENONE BROMIDE, 98+%
• CAS NO: 2689-63-6
• Molecular Formula: Br*C₂₇H₂₄OP
• Molecular Weight: 475.36
• EINECS: 220-255-3
• Mol File: 2689-63-6.mol

Chemical Properties

• Melting Point: 244-246°C
• Appearance: /
• Sensitive: Hygroscopic
• BRN: 4116852
• CAS DataBase Reference: (ALPHA-METHYLPHENACYL)TRIPHENYLPHOSPHONIUM BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (ALPHA-METHYLPHENACYL)TRIPHENYLPHOSPHONIUM BROMIDE(2689-63-6)
• EPA Substance Registry System: (ALPHA-METHYLPHENACYL)TRIPHENYLPHOSPHONIUM BROMIDE(2689-63-6)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 2689-63-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(ALPHA-METHYLPHENACYL)TRIPHENYLPHOSPHONIUM BROMIDE is used as a deprotecting reagent for selectively removing the 4-methylphenyl (TMP) protecting group from alcohols and phenols. This selective removal is crucial in the synthesis of complex organic molecules, where protecting groups are employed to shield functional groups from unwanted reactions during the synthesis process.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (ALPHA-METHYLPHENACYL)TRIPHENYLPHOSPHONIUM BROMIDE is used as a synthetic tool to facilitate the preparation of drug candidates. Its ability to selectively remove TMP protecting groups allows chemists to control the reactivity of specific functional groups, enabling the synthesis of complex molecules with precise structural features that are often required for biological activity.
Used in Academic Research:
(ALPHA-METHYLPHENACYL)TRIPHENYLPHOSPHONIUM BROMIDE is utilized in academic research as a reagent for exploring new synthetic pathways and methodologies. Its unique properties make it an attractive candidate for studying the mechanisms of deprotection and the development of novel strategies for the synthesis of complex organic compounds.
Used in Chemical Manufacturing:
In the chemical manufacturing industry, (ALPHA-METHYLPHENACYL)TRIPHENYLPHOSPHONIUM BROMIDE is employed as a key intermediate in the production of various specialty chemicals and materials. Its stability and reactivity make it suitable for large-scale processes, where the controlled removal of protecting groups is necessary for the synthesis of high-value products.

InChI:InChI=1/C27H24OP.BrH/c1-22(27(28)23-14-6-2-7-15-23)29(24-16-8-3-9-17-24,25-18-10-4-11-19-25)26-20-12-5-13-21-26;/h2-22H,1H3;1H/q+1;/p-1

Upstream product

• 93-55-0 1-phenyl-propan-1-one 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 603-35-0 triphenylphosphine 

Downstream Products

• 1450-07-3 1-benzoylethylidenetriphenylphosphorane 
• 1139768-51-6 2-methyl-1,4-diphenyl-3-buta-2,3-dien-1-one 
• 100518-51-2 1-phenyl-2-methyl-2,3-pentadien-1-one 

Relevant articles and documents

Fe-Catalyzed Cycloisomerization of Aryl Allenyl Ketones: Access to 3-Arylidene-indan-1-ones

A cycloisomerization of aryl allenyl ketones to 3-arylidene-indan-1-ones using a cationic Fe-complex as a catalyst is reported. The catalyst opens a synthetically interesting reaction pathway to this surprisingly underrepresented class of indanones that are not accessible using alternative catalytic systems.

Rasta Resin-TBD-Catalyzed γ-Selective Morita-Baylis-Hillman Reactions of α,γ-Disubstituted Allenones

Rasta resin-TBD (RR-TBD) was found to be an efficient organocatalyst for γ-selective Morita-Baylis-Hillman reactions between α,γ-disubstituted allenones and aryl aldehydes. In these reactions the heterogeneous nature of RR-TBD greatly facilitated product isolation since the catalyst could be separated simply by filtration.

Synthesis of C-glycosyl isoxazoles and branched-chain enuloses from 2,3-O-isopropylidene-D-glyceraldehyde

The synthesis of 5-glycosyl isoxazoles with 3-alkyl-, 3-aryl, 3,4-dialkyl, 3-aryl-4-alkyl or 3-alkyl-4-bromo substituents is reported. Deoxyenuloses were obtained from reaction of 2,3-O-isopropylidene-D-glyceraldehyde and several phosphorus ylides, which contain a carbonyl group, by a Wittig reaction. C-glycosyl α,β-unsaturated ketones were obtained, with the polyhydroxylate chain lengthened by two or three carbon atoms. In the second phase the ketones were transformed into the corresponding C-glycosyl α,β-unsaturated ketoximes, leading to the C-glycosyl isoxazoles, which were converted into the title compounds via removal of the isopropylidene group of suitably protected carbohydrates. The solubility of the synthetized C-glycosyl isoxazoles were modified by free hydroxyl groups in such a way that their behaviour against certain viruses and their potential antiviral activity could be studied.

Julia-Colonna asymmetric epoxidation reactions under non-aqueous conditions: Rapid, highly regio- and stereo-selective transformations using a cheap, recyclable catalyst

The asymmetric oxidation of some enones (Table 1), selected dienones 3-5, and a trienone 13 is accomplished using poly-L-leucine or poly-D-leucine and urea hydrogen peroxide under non-aqueous conditions. One of the resultant epoxy ketones 6 has been converted into the δ-lactones 19 and 22.