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
• Article Data: 4

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

General Description

(ALPHA-METHYLPHENACYL)TRIPHENYLPHOSPHONIUM BROMIDE, also known as Tris(4-methylphenyl)phosphine (TMP) bromide, is a chemical compound commonly used in organic synthesis as a powerful and selective deprotecting reagent. It is often used to remove the 4-methylphenyl (TMP) protecting group from alcohols and phenols. (ALPHA-METHYLPHENACYL)TRIPHENYLPHOSPHONIUM BROMIDE is a triphenylphosphonium salt with a bromide anion, which is highly stable and easy to handle. It is an important tool in the field of organic chemistry, particularly in the development of new synthetic methods and strategies for the preparation of complex molecules.

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

• 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 
• 1450-07-3 1-benzoylethylidenetriphenylphosphorane 

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.

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.