(3-Trimethylsilyl-2-propynyl)triphenylphosphonium bromide

Base Information

• Chemical Name: (3-Trimethylsilyl-2-propynyl)triphenylphosphonium bromide
• CAS No.: 42134-49-6
• Molecular Formula: C24H26BrPSi
• Molecular Weight: 453.434
• Hs Code.: 2931900090
• European Community (EC) Number: 625-526-3
• DSSTox Substance ID: DTXSID40369082
• Mol file: 42134-49-6.mol

Synonyms:42134-49-6;(3-Trimethylsilyl-2-propynyl)triphenylphosphonium bromide;Triphenyl(3-(trimethylsilyl)prop-2-yn-1-yl)phosphonium bromide;triphenyl(3-trimethylsilylprop-2-ynyl)phosphanium;bromide;SCHEMBL512714;DTXSID40369082;MFCD00012029;AKOS015833049;CS-0119968;FT-0639763;T1498;T72455;triphenyl(3-(trimethylsilyl)prop-2-ynyl)phosphonium bromide;Triphenyl(3-(trimethylsilyl)prop-2-yn-1-yl)phosphoniumbromide;triphenyl[3-(trimethylsilyl)prop-2-yn-1-yl]phosphanium bromide

Chemical Property of (3-Trimethylsilyl-2-propynyl)triphenylphosphonium bromide

Chemical Property:

• Appearance/Colour: beige to brownish crystalline powder
• Melting Point: 166-167 °C (dec.)(lit.)
• PSA: 13.59000
• LogP: 1.86530
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 452.07248
• Heavy Atom Count: 27
• Complexity: 442

Purity/Quality:

98%,99%, ^*data from raw suppliers

(3-Trimethylsilyl-2-propynyl)triphenylphosphonium Bromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)C#CC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-]
• Uses: (3-Trimethylsilyl-2-propynyl)triphenylphosphonium Bromide has been used in the synthesis of olefinic peptides that exhibit renin inhibitor activity against both hog kidney renin and human amniotic renin.

Technology Process of (3-Trimethylsilyl-2-propynyl)triphenylphosphonium bromide

There total 3 articles about (3-Trimethylsilyl-2-propynyl)triphenylphosphonium 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: 72.0%

3-bromo-1-(trimethylsilyl)-1-propyne (38002-45-8) + triphenylphosphine (603-35-0) → (3-trimethylsilyl-2-propynyl)triphenylphosphonium bromide (42134-49-6)

Guidance literature:

In o-xylene; at 0 - 25 ℃; Inert atmosphere;

DOI:10.1002/ejoc.200801184

Reference yield:

3-trimethylsilyl-2-propyn-1-ol (5272-36-6) → (3-trimethylsilyl-2-propynyl)triphenylphosphonium bromide (42134-49-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 30 percent / Br₂, triphenylphosphine / dimethylformamide / 18 h / Ambient temperature

2: 70 percent / benzene / 18 h / Ambient temperature

With bromine; triphenylphosphine; In N,N-dimethyl-formamide; benzene;

Reference yield:

(3-methoxy-1-propyn-1-yl)trimethylsilane (43019-55-2) → (3-trimethylsilyl-2-propynyl)triphenylphosphonium bromide (42134-49-6)

Guidance literature:

Multi-step reaction with 2 steps

1: BBr₃

With boron tribromide;

upstream raw materials:

3-bromo-1-(trimethylsilyl)-1-propyne

triphenylphosphine

3-trimethylsilyl-2-propyn-1-ol

(3-methoxy-1-propyn-1-yl)trimethylsilane

Downstream raw materials:

triphenyl(3-(trimethylsilyl)prop-2-yn-1-ylidene)-λ5-phosphane

C₁₈H₂₂Si

Refernces

• 1、 -. "PIPERIDINE DERIVATIVES AS LIVER X RECEPTOR β AGONISTS, COMPOSITIONS, AND THEIR USE". Page/Page column 76; 77. . Retrieved 2018/04/27.
• 2、 Hann, Michael M.,Sammes, Peter G.,Kennewell, Peter D.,Taylor, John B.. "On the Double Bond Isostere of the Peptide Bond: Preparation of an Enkephalin Analogue". . p. 307 - 314. Retrieved 2007/10/02.