Cyanomethylenetributylphosphorane

Base Information

• Chemical Name: Cyanomethylenetributylphosphorane
• CAS No.: 157141-27-0
• Molecular Formula: C14H28 N P
• Molecular Weight: 241.357
• Hs Code.: 2931499090
• European Community (EC) Number: 679-660-2
• DSSTox Substance ID: DTXSID90404992
• Nikkaji Number: J1.882.895B,J726.653G
• Mol file: 157141-27-0.mol

Synonyms:157141-27-0;Cyanomethylenetributylphosphorane;2-(Tributylphosphoranylidene)acetonitrile;(Tributylphosphoranylidene)acetonitrile;2-(tributyl-lambda5-phosphanylidene)acetonitrile;Acetonitrile, 2-(tributylphosphoranylidene)-;(cyanomethylene)tributylphosphorane;cyanomethylenetri-n-butylphosphorane;MFCD01321151;Acetonitrile, (tributylphosphoranylidene)-;2-tributylphosphoranylideneacetonitrile;2-(TRIBUTYL-??-PHOSPHANYLIDENE)ACETONITRILE;cyanomethylenetribuylphosphorane;SCHEMBL182256;cyanomethylene tributylphosphorane;cyanomethylenetributyl-phosphorane;Cyanomethylene)tributylphosphorane;DTXSID90404992;cyanomethylene tributyl phosphorane;OZMLUMPWPFZWTP-UHFFFAOYSA-N;(cyano-methylene)tributylphosphorane;(cyanomethylene)-tributylphosphorane;Cyanomethylene-(tributyl)phosphorane;cyanomethylene tri-n-butylphosphorane;cyanomethylene-tri-n-butylphosphorane;(tributylphosphoranyliden)acetonitrile;cyanomethylene tri-n-butyl phosphorane;AKOS015836097;(Tributyl phosphoranylidene)acetonitrile;2-(tributylphosphoranylidene) acetonitrile;SY025792;2-(tributyl-l5-phosphanylidene)acetonitrile;CS-0046100;(tributyl-lambda5-phosphanylidene)acetonitrile;(Tributyl-lambda5-phosphanylidene)-acetonitrile;{[Tri(but-1-yl)]phosphoranylidene}acetonitrile;A50071;EN300-316330;(Tributyl-lambda-5-phosphanylidene)-acetonitrile;A883521;J-009383

Chemical Property of Cyanomethylenetributylphosphorane

Chemical Property:

• Vapor Pressure: 9.38E-05mmHg at 25°C
• Refractive Index: 1.45
• Boiling Point: 339.1°Cat760mmHg
• Flash Point: 158.9°C
• PSA: 33.60000
• Density: 0.882g/cm³
• LogP: 4.73008
• Storage Temp.: Refrigerator
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 9
• Exact Mass: 241.195936895
• Heavy Atom Count: 16
• Complexity: 231

Purity/Quality:

97% ^*data from raw suppliers

2-(Tributylphosphoranylidene)acetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: F,Xn
• Statements: 10-23/24/25-67-65-48/20-38-11-63
• Safety Statements: 16-26-36/37/39-62-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCP(=CC#N)(CCCC)CCCC
• Uses: (Tributylphosphoranylidene)acetonitrile can be utilized as a reagent in the: Stereoselective synthesis of skytanthine and other O- and N-containing heterocycles by Mitsunobu intramolecular cycloalkylation.Wittig olefination of esters, lactones, N-Boc lactam, and cyclic imide to corresponding Wittig products.

Technology Process of Cyanomethylenetributylphosphorane

There total 3 articles about Cyanomethylenetributylphosphorane 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: 95.0%

(cyanomethyl)tributylphosphonium chloride (82358-61-0) → cyanomethylenetributyl-phosphorane (157141-27-0)

Guidance literature:

With n-butyllithium; In hexane; at 0 - 20 ℃; for 20h;

DOI:10.1248/cpb.53.1508

Reference yield:

tributylphosphine (998-40-3) → cyanomethylenetributyl-phosphorane (157141-27-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / nitromethane / 21 h / Ambient temperature

2: 91 percent / BuLi/hexane / tetrahydrofuran / 1 h / 0 °C

With n-butyllithium; hexane; In tetrahydrofuran; nitromethane;

DOI:10.1016/S0040-4039(00)73326-0

Reference yield:

tributylphosphine (998-40-3) → cyanomethylenetributyl-phosphorane (157141-27-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / nitromethane / 16 h / 20 °C

2: 95 percent / n-butyllithium / hexane / 20 h / 0 - 20 °C

With n-butyllithium; In nitromethane; hexane;

DOI:10.1248/cpb.53.1508

upstream raw materials:

(cyanomethyl)tributylphosphonium chloride

tributylphosphine

Refernces

A convenient method for the asymmetric synthesis of fluorinated α-amino acids from alcohols

10.1002/ejoc.201301718

The research focuses on the asymmetric synthesis of fluorinated α-amino acids from alcohols, highlighting a convenient method using Mitsunobu–Tsunoda alkylation of a chiral nucleophilic glycine equivalent. The experiments involve the reaction of a nickel(II) complex of glycine Schiff base with various fluorinated alcohols, utilizing (cyanomethylene)tributylphosphorane as the reagent. The study explores different solvents and conditions to optimize the reaction, with the aim of achieving high yields and excellent diastereoselectivity. The reactants include the nickel complex, the phosphorane reagent, and a range of fluorinated alcohols. The analyses used to characterize the products and monitor the reactions include NMR spectroscopy, infrared spectroscopy, high-resolution mass spectrometry, and chiral HPLC to determine enantiomeric excess. The research also discusses potential mechanisms for the formation of certain products and byproducts, and concludes with a general procedure for the synthesis and cleavage of the NiII complex to yield the desired fluorinated amino acids.