(cyanomethyl)triphenylphosphanium chloride

• ChemBase ID: 74857
• Molecular Formular: C20H17ClNP
• Molecular Mass: 337.782441
• Monoisotopic Mass: 337.07871386
• SMILES: [P+](c1ccccc1)(c1ccccc1)(c1ccccc1)CC#N.[Cl-]
• Canonical SMILES: N#CC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Cl-]
• InChI: InChI=1S/C20H17NP.ClH/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;1H/q+1;/p-1
• InChIKey: ARPLQAMUUDIHIT-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: (cyanomethyl)triphenylphosphanium chloride
• IUPAC Traditional name: (cyanomethyl)triphenylphosphanium chloride
• Synonyms: NSC 92174; (Cyanomethyl)triphenylphosphonium chloride; (Cyanomethyl)triphenylphosphonium chloride; (氰甲基)三苯基氯化膦; (氰甲基)三苯基氯化磷鎓

Database IDs

• CAS Number: 4336-70-3
• EC Number: 224-383-0
• MDL Number: MFCD00031672
• Beilstein Number: 6222047
• PubChem SID: 162039775; 24870234
• PubChem CID: 197040

CALCULATED PROPERTIES

• Acid pKa: 7.5955844
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 3.952703
• LogD (pH = 7.4): 3.7425656
• Log P: 3.9561672
• Molar Refractivity: 92.3835 cm^3
• Polarizability: 36.063854 Å^3
• Polar Surface Area: 23.79 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 275 °C (dec.)(lit.); ca 270°C dec.

Safety Information

• Storage Warning: Hygroscopic; Toxic
• RTECS: TA2075000
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: UN3439
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: III
• Risk Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37; 26-37/39
• TSCA Listed: 否
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H319-H332-H335; H331-H302-H312-H315-H319-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95+%; 98%; 98+%
• Linear Formula: NCCH2P(C6H5)3Cl

DETAILS

Sigma Aldrich - 464937

Packaging
25 g in glass bottle
Application
Reactant involved in:
• Condenation reactions1,2
• Wittig reactions3,4,5
• Synthesis of phosphonium-iodonium ylides6
• Preparation of α,β-unsaturated esters, amides, and nitriles7

REFERENCES

• Forms a moderately stable crystalline ylide which reacts with aldehydes to give ɑ?-unsaturated nitriles, predominantly as their (Z)-isomers: Chem. Ber., 94, 578 (1961); J. Chem. Soc., 1266 (1961); Appendix 1.
• Further deprotonation of the phosphorane with sodium bis(trimethylsilyl)amide followed by C-alkylation generates a homologated phosphorane: Angew. Chem. Int. Ed., 26, 79 (1987).
• Reaction of the ylide with carboxylic acids in the presence of EDCI (1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, A10807) and DMAP, followed by ozonolysis of the resulting acylphosphoranes, provides a novel route to the homologous ɑ-keto esters: J. Org. Chem., 59, 4364 (1994):