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

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

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 
• 122-04-3 4-nitro-benzoyl chloride 
• 107-14-2 chloroacetonitrile 
• 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 
• 75-36-5 acetyl chloride 
• 100-07-2 4-methoxy-benzoyl chloride 

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.

COMPOUNDS, COMPOSITIONS AND METHODS OF INCREASING CFTR ACTIVITY

The present disclosure features compounds such as those having the Formulae (I) and (II), which can increase cystic fibrosis transmembrane conductance regulator (CFTR) activity as measured in human bronchial epithelial (hBE) cells. The present disclosure also features methods of treating a condition associated with decreased CFTR activity or a condition associated with a dysfunction of proteostasis comprising administering to a subject an effective amount of a disclosed compound, such as a compound of Formula (I) or (II).

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.

COMPOUNDS, COMPOSITIONS, AND METHODS FOR INCREASING CFTR ACTIVITY

The present disclosure is directed to disclosed compounds that increase cystic fibrosis transmembrane conductance regulator (CFTR) activity as measured in human bronchial epithelial (hBE) cells.

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.

Demonic axe-like conjugated alkynes in combating microbes

A new series of disubstituted alkynes was obtained by microwave induced internal splitting of the corresponding β-oxo- alkylidenetriphenylphosphoranes. The antimicrobial potential of these conjugated alkynes and phosphoranes was assayed in vitro against three Gram-positive bacteria (Staphylococcus aureus, Bacillus subtilis, Staphylococcus epidermidis), three Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae) and five fungal strains (Aspergillus niger, Candida albicans, Aspergillus flavus, Candida rugosa, Saccharomyces cerevisiae). The 3-pyridylalkyne derivatives viz., 3-(6-chloropyridin-3-yl)propynenitrile (6a), 3-(2-chloropyridin-3-yl)propynenitrile (6b), ethyl 3-(6-chloropyridin-3-yl) propiolate (6c), iso-propyl 3-(6-chloropyridin-3-yl)propiolate (6d) and 3-(2,6-dichloro-5-fluoropyridin-3-yl)propynenitrile (6e) were found to be highly potent towards all tested microorganisms except E. coli.

A modular synthesis of teraryl-based α-helix mimetics, part 1: Synthesis of core fragments with two electronically differentiated leaving groups

Teraryl-based α-helix mimetics have proven to be useful compounds for the inhibition of protein-protein interactions (PPI). We have developed a modular and flexible approach for the synthesis of teraryl-based α-helix mimetics. Central to our strategy is the use of a benzene core unit featuring two leaving groups of differentiated reactivity in the Pd-catalyzed cross-coupling used for terphenyl assembly. With the halogen/diazonium route and the halogen/triflate route, two strategies have successfully been established. The synthesis of core building blocks with aliphatic (Ala, Val, Leu, Ile), aromatic (Phe), polar (Cys, Lys), hydrophilic (Ser, Gln), and acidic (Glu) amino acid side chains are reported. Turn on: Teraryl-based α-helix mimetics can be effectively produced by sequential Suzuki coupling of a central core fragment featuring electronically differentiated leaving groups with aryl boronic pinacol esters (see scheme; dppf=1,1′-bis(diphenylphosphino) ferrocene, DME=dimethoxyethane, Pin=pinacol, Tf=trifluoromethanesulfonyl). With a set of only 2×18 building blocks, all permutations of α-helix mimetics can be produced. Copyright

Synthesis, thermal reactivity, and kinetics of stabilized phosphorus ylides, part 2: [(Arylcarbamoyl) (cyano)-methylene] triphenylphos-phoranes and their thiocarbamoyl analogues

A series of five cyano(arylcarbamoyl) phosphorus ylides 2 and five cyano-(arylthiocarbamoyl) phosphorus ylides 3 are prepared and fully characterized. Pyrolytic reaction products of a representative example of each type obtained by flash vacuum pyrolysis technique show that they undergo thermal extrusion of Ph3PO or Ph3PS. Kinetic study of the gas-phase pyrolysis of each ylide by static method shows that these reactions are unimolecular and first order with no significant substituent effect, but the thiocarbamoyl ylides 3 react 40-65 times more rapidly than their carbamoyl analogues 2.

Aza-Wittig reaction of fluoroalkylated N-vinylic phosphazenes with carbonyl compounds. Usefulness of 2-azadienes for the preparation of fluoroalkyl pyridine derivatives

A method for the preparation of 3-fluoroalkyl substituted 2-aza-butadienes 6 by aza-Wittig reaction of 3-fluoroalkyl-N-vinylic phosphazenes 4 and aldehydes 5 is reported. [4+2] Cycloaddition reaction of these heterodienes 6 with enamines 9 gives fluoroalkyl substituted pyridine 15, 16, 24-27 and isoquinoline 12-14, 20 derivatives.

Synthesis of chlorophyll-a homologs by Wittig and Knoevenagel reactions with methyl pyropheophorbide-d

The formyl group at the 3-position of methyl pyropheophorbide-d reacted with phosphorous ylides and activated methylene compounds to give efficiently the corresponding 3-(2-substituted ethenyl)chlorins compounds as a product of Wittig and Knoevenagel reactions. The trans-isomers of the synthetic chlorins, methyl 32-substituted pyropheophorbide-a had visible bands absorbing longer wavelengths than the cis-isomers and the 32-unsubstituted chlorin, methyl pyropheophorbide-a. 32,32-Disubstitution strongly affected the absorption bands compared with the bands of the 32-monosubstituted chlorins. The absorption, fluorescence and circular dichroism spectra were dependent upon the 3-substituents conjugated with the chlorin chromophore.