METHYL 4-(TRIPHENYLPHOSPHONIO)CROTONATE BROMIDE

Base Information

• Chemical Name: METHYL 4-(TRIPHENYLPHOSPHONIO)CROTONATE BROMIDE
• CAS No.: 2181-98-8
• Molecular Formula: Br*C₂₃H₂₂O₂P
• Molecular Weight: 441.304
• European Community (EC) Number: 218-557-5
• Mol file: 2181-98-8.mol

Synonyms:(3-Carboxyallyl)triphenylphosphoniumbromide, methyl ester (6CI,7CI); Phosphonium, (3-carboxyallyl)triphenyl-,bromide, methyl ester (8CI); Phosphonium,(4-methoxy-4-oxo-2-butenyl)triphenyl-, bromide (9CI);(3-Carbomethoxy-2-propenyl)triphenylphosphonium bromide;[3-(Methoxycarbonyl)-2-propenyl]triphenylphosphonium bromide

Chemical Property of METHYL 4-(TRIPHENYLPHOSPHONIO)CROTONATE BROMIDE

Chemical Property:

• Melting Point: 175°C (dec.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 39.89000
• Density: g/cm³
• LogP: 0.71370
• Sensitive.: Hygroscopic
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 440.05408
• Heavy Atom Count: 27
• Complexity: 409

Purity/Quality:

99% ^*data from raw suppliers

Methyl4-(triphenylphosphonio)crotonateBromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: R36/37/38:Irritating to eyes, respiratory system and skin.
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C=CC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-]
• Isomeric SMILES: COC(=O)/C=C/C[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-]
• Uses: Methyl 4-(triphenylphosphonio)crotonate Bromide was used in the stereospecific synthesis of (+)-oxybiotin.

Technology Process of METHYL 4-(TRIPHENYLPHOSPHONIO)CROTONATE BROMIDE

There total 5 articles about METHYL 4-(TRIPHENYLPHOSPHONIO)CROTONATE BROMIDE 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: 56.0%

methyl-4-bromo-2-butenoate (1117-71-1,56699-18-4,6000-00-6) + triphenylphosphine (603-35-0) → <3-carbomethoxy-propen-(2)-yl-(1)>-triphenylphosphoniumbromide (2181-98-8,72967-11-4)

Guidance literature:

In toluene; at 20 ℃; for 48h; Inert atmosphere;

DOI:10.1021/acs.orglett.8b00028

Reference yield: 20.0%

methyl 4-chloro-2-butenoate (15320-72-6) + triphenylphosphine (603-35-0) → <3-carbomethoxy-propen-(2)-yl-(1)>-triphenylphosphoniumbromide (2181-98-8,72967-11-4)

Guidance literature:

In N,N-dimethyl-formamide; at 70 ℃; for 1h;

Reference yield:

methyl 4-chloro-2-butenoate (15320-72-6) + triphenylphosphine hydrobromide (6399-81-1) → <3-carbomethoxy-propen-(2)-yl-(1)>-triphenylphosphoniumbromide (2181-98-8,72967-11-4)

Guidance literature:

In N,N-dimethyl-formamide; at 70 ℃; for 1h; Yield given;

upstream raw materials:

methyl 4-bromocrotonate

triphenylphosphine

methyl 4-chloro-2-butenoate

triphenylphosphine hydrobromide

Downstream raw materials:

Benzoic acid (3R,4R,5S)-5-((1E,3E)-4-methoxycarbonyl-buta-1,3-dienyl)-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-3-yl ester

Refernces

• 1、 Hercouet, A.,Corre, M. Le. "COMMUNICATION. Utilisation du Bromhydrate de Triphenylphosphine pour la Synthese de Sels d'Alkyltriphenylphosphonium". . p. 111 - 114. Retrieved 2007/10/02.