4336-70-3

Basic information

• Product Name: (CYANOMETHYL)TRIPHENYLPHOSPHONIUM CHLORIDE
• Synonyms: (CYANOMETHYL)TRIPHENYLPHOSPHONIUM CHLORIDE;(cyanomethyl)triphenyl-phosphoniuchloride;Cyanomethyl triphenylphosphonium chloride, 98+%;Triphenyl(cyanomethyl)phosphonium·chloride;Cyanomethyl triphenylphosphonium chloride,97%;NSC 92174;(Cyanomethyl)triphenylphosphonium chloride 98%;2-(chlorotriphenyl-l5-phosphanyl)acetonitrile
• CAS NO: 4336-70-3
• Molecular Formula: C₂₀H₁₇NP*Cl
• Molecular Weight: 337.78
• EINECS: 224-383-0
• Product Categories: Phosphonium Compounds;Synthetic Organic Chemistry;Wittig & Horner-Emmons Reaction;Wittig Reaction;C-C Bond Formation;Olefination;Wittig Reagents
• Mol File: 4336-70-3.mol
• Article Data: 15

Chemical Properties

• Melting Point: 268-270 °C
• Appearance: /solid
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: very faint turbidity
• Sensitive: Hygroscopic
• BRN: 6222047
• CAS DataBase Reference: (CYANOMETHYL)TRIPHENYLPHOSPHONIUM CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (CYANOMETHYL)TRIPHENYLPHOSPHONIUM CHLORIDE(4336-70-3)
• EPA Substance Registry System: (CYANOMETHYL)TRIPHENYLPHOSPHONIUM CHLORIDE(4336-70-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 37/39-26
• RIDADR: 3276
• WGK Germany: 3
• RTECS: TA2075000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 4336-70-3(Hazardous Substances Data)

Usage

Description

(Cyanomethyl)triphenylphosphonium chloride is a chemical compound with the formula (CNCH2)P(C6H5)3Cl. It is an off-white crystalline powder that serves as a versatile reagent in organic synthesis, particularly in the formation of phosphonium-iodonium ylides.

Uses

Used in Organic Synthesis:
(Cyanomethyl)triphenylphosphonium chloride is used as a reagent for the preparation of phosphonium-iodonium ylides, which are key intermediates in various organic reactions. These ylides are valuable for their ability to participate in a range of chemical transformations, including the synthesis of complex organic molecules.
Used in Condensation Reactions:
In the field of organic chemistry, (cyanomethyl)triphenylphosphonium chloride is utilized as a catalyst in condensation reactions. Its role in these reactions facilitates the formation of new carbon-carbon or carbon-heteroatom bonds, which are essential for constructing complex molecular structures.
Used in Wittig Reactions:
(CYANOMETHYL)TRIPHENYLPHOSPHONIUM CHLORIDE is also employed as a reactant in Wittig reactions, which are widely used for the synthesis of alkenes from aldehydes or ketones. The phosphonium-iodonium ylides generated from (cyanomethyl)triphenylphosphonium chloride play a crucial role in the formation of the desired alkene products.
Used in the Preparation of α,β-Unsaturated Esters, Amides, and Nitriles:
(Cyanomethyl)triphenylphosphonium chloride is used as a reactant in the synthesis of α,β-unsaturated esters, amides, and nitriles. These compounds are important building blocks in the preparation of various pharmaceuticals, agrochemicals, and other specialty chemicals.

InChI:InChI=1/C20H17NP/c21-16-17-22(18-10-4-1-5-11-18,19-12-6-2-7-13-19)20-14-8-3-9-15-20/h1-15H,17H2/q+1

Upstream product

• 545-06-2 trichloroacetonitrile 
• 603-35-0 triphenylphosphine 
• 1120-06-5 decan-2-ol 
• 541-41-3 chloroformic acid ethyl ester 
• 16640-68-9 cyanomethylene triphenylphosphorane 
• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 
• 100-07-2 4-methoxy-benzoyl chloride 
• 122-04-3 4-nitro-benzoyl chloride 
• 107-14-2 chloroacetonitrile 
• 75-36-5 acetyl chloride 
• 354-32-5 trifluoracetyl chloride 
• 422-59-3 2,2,3,3,3-pentafluoropropionyl chloride 
• 375-16-6 heptafluorobutyryl chloride 
• 16331-46-7 4-ethoxybenzoylchloride 

Downstream Products

• 16640-68-9 cyanomethylene triphenylphosphorane 
• 15935-50-9 2-[5-cyano-3-methyl-5-(triphenyl-λ⁵-phosphanylidene)-penta-1,3-dienyl]-3-ethyl-5-methoxy-benzothiazolium; iodide 
• 37400-63-8 2-[5-cyano-3-methyl-5-(triphenyl-λ⁵-phosphanylidene)-penta-1,3-dienyl]-3-ethyl-5-methoxy-benzoselenazolium; iodide 
• 16380-44-2 2-[3-cyano-3-(triphenyl-λ⁵-phosphanylidene)-propenyl]-3-ethyl-benzothiazolium; chloride 
• 16380-47-5 2-[3-cyano-3-(triphenyl-λ⁵-phosphanylidene)-propenyl]-3-ethyl-benzoselenazolium; chloride 
• 15992-66-2 2-[5-cyano-3-methyl-5-(triphenyl-λ⁵-phosphanylidene)-penta-1,3-dienyl]-3-ethyl-benzothiazolium; iodide 
• 15935-47-4 2-[5-cyano-3-ethyl-5-(triphenyl-λ⁵-phosphanylidene)-penta-1,3-dienyl]-3-ethyl-benzothiazolium; iodide 
• 16380-45-3 2-[3-cyano-3-(triphenyl-λ⁵-phosphanylidene)-propenyl]-3-ethyl-5-methoxy-benzothiazolium; iodide 
• 16380-48-6 2-[3-cyano-3-(triphenyl-λ⁵-phosphanylidene)-propenyl]-3-ethyl-5-methoxy-benzoselenazolium; iodide 
• 15935-48-5 2-[5-cyano-3-methyl-5-(triphenyl-λ⁵-phosphanylidene)-penta-1,3-dienyl]-3-ethyl-5,6-dimethyl-benzothiazolium; iodide 
• 16380-46-4 2-[3-cyano-3-(triphenyl-λ⁵-phosphanylidene)-propenyl]-3-ethyl-naphtho[2,1-d]thiazolium; iodide 
• 15935-49-6 2-[5-cyano-3-ethyl-5-(triphenyl-λ⁵-phosphanylidene)-penta-1,3-dienyl]-3-ethyl-5,6-dimethyl-benzothiazolium; iodide 
• 15935-51-0 2-[5-cyano-3-ethyl-5-(triphenyl-λ⁵-phosphanylidene)-penta-1,3-dienyl]-3-ethyl-5-methoxy-benzothiazolium; iodide 
• 15960-91-5 2-[5-cyano-3-ethyl-5-(triphenyl-λ⁵-phosphanylidene)-penta-1,3-dienyl]-3-ethyl-5-methoxy-benzoselenazolium; iodide 

Relevant articles and documents

A Triazolotriazine-Based Dual GSK-3β/CK-1δ Ligand as a Potential Neuroprotective Agent Presenting Two Different Mechanisms of Enzymatic Inhibition

Glycogen synthase kinase 3β (GSK-3β) and casein kinase 1δ (CK-1δ) are emerging targets for the treatment of neuroinflammatory disorders, including Parkinson's disease. An inhibitor able to target these two kinases was developed by docking-based design. Compound 12, 3-(7-amino-5-(cyclohexylamino)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-2-yl)-2-cyanoacrylamide, showed combined inhibitory activity against GSK-3β and CK-1δ [IC50(GSK-3β)=0.17 μm; IC50(CK-1δ)=0.68 μm]. In particular, classical ATP competition was observed against CK-1δ, and a co-crystal of compound 12 inside GSK-3β confirmed a covalent interaction between the cyanoacrylamide warhead and Cys199, which could help in the development of more potent covalent inhibitors of GSK-3β. Preliminary studies on in vitro models of Parkinson's disease revealed that compound 12 is not cytotoxic and shows neuroprotective activity. These results encourage further investigations to validate GSK-3β/CK-1δ inhibition as a possible new strategy to treat neuroinflammatory/degenerative diseases.

METHODS OF TREATING PULMONARY DISEASES AND DISORDERS

The present disclosure features disclosed method of treating disorders such as COPD, bronchitis and/or asthma using disclosed compounds, optionally together with one or more additional active agents. Contemplated methods include administrating orally or by inhalation to a patient one or more disclosed compounds.

Synthesis and antimicrobial activity of N-aryl-4-(cyano/alkoxycarbonyl)-5-(pyridin-3-yl)-1H/3H-1,2,3-triazole derivatives

A convenient synthesis of a new series of N-aryl-5-(pyridin-3-yl)-1H/3H-1,2,3-triazole-4-carbonitriles and alkyl N-aryl-5-(pyridin-3-yl)-1H/3H-1,2,3-triazole-4-carboxylic acid esters is reported. The newly synthesized 5-(pyridin-3-yl)-1,2,3-triazole derivatives are evaluated for their antibacterial and antifungal activity. Some of these triazole derivatives have exhibited moderate antimicrobial activity.