Methyltriphenylphosphonium bromide

Base Information

• Chemical Name: Methyltriphenylphosphonium bromide
• CAS No.: 1779-49-3
• Deprecated CAS: 131507-02-3,27200-84-6,2069974-10-1,1233518-83-6,2413994-38-2,2640505-88-8
• Molecular Formula: C19H18P·Br
• Molecular Weight: 357.23
• Hs Code.: 29310095
• European Community (EC) Number: 217-218-9
• NSC Number: 102058,20740
• UNII: LW2UZ3E9EG
• DSSTox Substance ID: DTXSID30883580
• Wikipedia: Methyltriphenylphosphonium_bromide
• ChEMBL ID: CHEMBL54469
• Mol file: 1779-49-3.mol

Synonyms:methyltriphenylphosphonium ion;TPMP;triphenylmethylphosphonium;triphenylmethylphosphonium bromide;triphenylmethylphosphonium iodide, (14)C-labeled

Chemical Property of Methyltriphenylphosphonium bromide

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0.0000002 hPa
• Melting Point: 230-234 °C(lit.)
• Flash Point: >240°C
• PSA: 13.59000
• LogP: 0.61430
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: H2O: 0.1 g/mL, clear
• Water Solubility.: 400 g/L (25 ºC)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 356.03295
• Heavy Atom Count: 21
• Complexity: 235

Purity/Quality:

99% ^*data from raw suppliers

Methyltriphenylphosphonium Bromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 36/37-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Phosphorus Compounds
• Canonical SMILES: C[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-]
• General Description: Methyltriphenylphosphonium bromide is a phosphonium salt commonly used as a reagent in organic synthesis, particularly in Wittig reactions for the formation of alkenes from carbonyl compounds. In the context of the described research, it likely served as a precursor for generating ylides or as a reagent in key transformation steps, contributing to the ring expansion and stereocontrol strategies employed in the total synthesis of d,l-methynolide. Its role underscores its utility in constructing complex macrocyclic frameworks.

Technology Process of Methyltriphenylphosphonium bromide

There total 34 articles about Methyltriphenylphosphonium 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: 99.2%

methanol (67-56-1) + triphenylphosphine (603-35-0) → Methyltriphenylphosphonium bromide (1779-49-3)

Guidance literature:

With hydrogen bromide; at 110 ℃; for 8h;

Reference yield: 99.0%

methyl bromide (74-83-9) + triphenylphosphine (603-35-0) → Methyltriphenylphosphonium bromide (1779-49-3)

Guidance literature:

In benzene; at 20 ℃; for 4h;

DOI:10.1080/10426500701613030

Reference yield: 96.0%

triphenylphosphine (603-35-0) + trimethyl orthoformate (149-73-5) → Methyltriphenylphosphonium bromide (1779-49-3)

Guidance literature:

With ammonium bromide; at 110 ℃; for 4h; Sealed tube;

DOI:10.1016/j.tet.2020.131107

upstream raw materials:

methyl bromide

triphenylphosphine

diazomethane

triphenylphosphine hydrobromide

Downstream raw materials:

3β-hydroxy-10.13-dimethyl-17-methylene-gonene-(5)

cyclohexylidene-((E)-2-methylene-cyclohexyliden)-ethane

9-decen-1-yl acetate

1-Methylen-3,5-diphenylcyclohex-2-en

Refernces

Total synthesis of d,l-methynolide. Medium-ring sulfides by ylide ring expansion

10.1021/ja00204a015

The research focuses on the total synthesis of d,l-methynolide, the aglycon of the macrolide antibiotic methymycin, utilizing sulfur-mediated ring expansion technology. The purpose of this study was to develop a synthetic approach that relies on sequential 2,3-sigmatropic rearrangements of stabilized sulfonium ylides to build cyclic sulfides of varying ring sizes and to achieve remote stereocontrol through the predictable conformational properties of medium-sized ring intermediates and the stereoelectronic effect of sulfur α to ketone carbonyl. The successful route involved the ring expansion of sulfonium ylide to an eight-membered sulfide, followed by conversion to alcohol and reduction of the double bond to form the saturated analogue. Key chemicals used in the process included sulfonium ylides, sulfides, alcohols, and various reagents for protection, oxidation, and reduction steps, such as lithium ethyl boranolate (LiEt3BH), methyltriphenylphosphonium bromide, potassium tert-butoxide, and p-toluenesulfonylhydrazide, among others. The conclusions of the research detailed the successful synthesis of d,l-methynolide and a similar route to ClO-epi-methynolide, demonstrating the efficacy of the sulfur-based strategy for remote stereocontrol in complex macrocycle synthesis.