(Triphenylphosphoranylidene)acetonitrile

Base Information

• Chemical Name: (Triphenylphosphoranylidene)acetonitrile
• CAS No.: 16640-68-9
• Molecular Formula: C20H16NP
• Molecular Weight: 301.327
• Hs Code.: 29319090
• European Community (EC) Number: 240-689-7
• NSC Number: 135204
• UNII: AP7LR5WB3X
• DSSTox Substance ID: DTXSID60168099
• Nikkaji Number: J1.700.350J,J82.530A
• Wikidata: Q83037606
• Mol file: 16640-68-9.mol

Synonyms:16640-68-9;(Triphenylphosphoranylidene)acetonitrile;2-(Triphenylphosphoranylidene)acetonitrile;(Cyanomethylene)triphenylphosphorane;2-(triphenyl-lambda5-phosphanylidene)acetonitrile;C20H16NP;Acetonitrile, (triphenylphosphoranylidene)-;Cyanomethylene triphenylphosphorane;EINECS 240-689-7;NSC-135204;Acetonitrile, 2-(triphenylphosphoranylidene)-;AP7LR5WB3X;2-(triphenyl-$l^{5}-phosphanylidene)acetonitrile;SCHEMBL377725;cyanomethylenetriphenylphosphorane;Triphenylphosphinideneacetonitrile;DTXSID60168099;(Cyanomethyl)triphenylphosphonium-;(Triphenylphosphoranyl)acetonitrile;Cyano(triphenylphosphonio)methanide;BCP22527;C20-H16-N-P;Cyanomethyltriphenylphosphonium ylide;STR07878;Phosphonium, (cyanomethyl)triphenyl-;triphenylphosphoranylideneacetonitrile;(triphenylphosphanylidene)acetonitrile;GEO-03962;MFCD00567633;NSC135204;triphenylphosphoranylidene acetonitrile;AKOS001584055;AKOS037795664;CS-W004790;NSC 135204;(triphenylphosphoranylidene) acetonitrile;2-(Triphenylphosphanylidene)acetonitrile;AM803298;T1958;(Triphenylphosphoranylidene)acetonitrile, 97%;EN300-175964;A882327;J-010276

Chemical Property of (Triphenylphosphoranylidene)acetonitrile

Chemical Property:

• Appearance/Colour: Off-white to light yellow crystalline powder
• Vapor Pressure: 7.8E-09mmHg at 25°C
• Melting Point: 189-195 °C(lit.)
• Refractive Index: 1.627
• Boiling Point: 465.3 °C at 760 mmHg
• Flash Point: 235.2 °C
• PSA: 33.60000
• Density: 1.16 g/cm³
• LogP: 3.30628
• Storage Temp.: Refrigerator
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 301.102036512
• Heavy Atom Count: 22
• Complexity: 387

Purity/Quality:

98%, ^*data from raw suppliers

(Triphenylphosphoran?ylidene)?acetonitrile ^*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

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)P(=CC#N)(C2=CC=CC=C2)C3=CC=CC=C3
• Uses: (Triphenylphosphoran?ylidene)?acetonitrile is a reactant in the synthesis of largazole analogues which displays potent cell growth inhibition and cytotoxicity. As well, is used in the synthesis of monoterpene derivatives against leukemia.

Technology Process of (Triphenylphosphoranylidene)acetonitrile

There total 16 articles about (Triphenylphosphoranylidene)acetonitrile 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: 98.0%

(cyanomethyl)triphenylphosphonium bromide (15898-47-2) → cyanomethylene triphenylphosphorane (16640-68-9)

Guidance literature:

With potassium hydroxide; In dichloromethane;

DOI:10.1021/ja065790c

Reference yield: 93.0%

(cyanomethyl)triphenylphosphonium chloride (4336-70-3) → cyanomethylene triphenylphosphorane (16640-68-9)

Guidance literature:

With sodium hydroxide; In water; at 25 ℃; for 0.583333h;

DOI:10.1021/acs.jpca.1c03246

Reference yield:

triphenylphosphine (603-35-0) + cyanomethyl bromide (590-17-0) → cyanomethylene triphenylphosphorane (16640-68-9)

Guidance literature:

In ethyl acetate; at 85 ℃;

upstream raw materials:

(cyanomethyl)triphenylphosphonium chloride

(cyanomethyl)triphenylphosphonium bromide

p-tolylcyanate

Methylenetriphenylphosphorane

Downstream raw materials:

2-triphenylphosphorylidene-3-oxo-3-phenylpropionitrile

3-Phenyl-2-propynonitrile

3-Cyano-3-(triphenyl-λ⁵-phosphanylidene)-propionic acid methyl ester

1-Cyan-2-oxo-4-phenyl-but-3-in-yliden-triphenyl-phosphoran

Refernces

The reactions of triphenylphosphine alkylenes with 3(2-thienyl)acrylonitriles

10.1080/10426500307778

The research investigates the reactions of triphenylphosphine alkylenes with 3(2-thienyl)acrylonitriles, aiming to explore the formation of various products under different reaction conditions and the influence of the substituents on the reaction outcomes. Key chemicals involved include ethyl 3-(2-thienyl)acrylocyanoacetate (1b), various ylides such as (methoxycarbonylmethylene)triphenylphosphorane (2a), (ethoxycarbonylmethylene)triphenylphosphorane (2b), (benzoylmethylene)triphenylphosphorane (2c), and (cyanomethylene)triphenylphosphorane (14). The study found that the initial Michael addition of ylides to the exocyclic methide carbon in 1b leads to diverse products depending on the nature of the ylide and reaction conditions. For instance, reactions with 2a and 2b in the presence of triethylamine yielded cyclopropane derivatives and new ylides, while the reaction with 2c in ethyl acetate containing benzoic acid produced a pyran derivative. The reaction of (cyanomethylene)triphenylphosphorane (14) with 1b resulted in a cyclopropane derivative, whereas with malonitrile 1a, it produced a ylide and a propene derivative. The research concludes that the substituents on the ylides and the reaction conditions significantly affect the reaction pathways and products, highlighting the versatility of these reactions in synthesizing complex organic compounds with potential biological activities.