(CYANOMETHYL)TRIPHENYLPHOSPHONIUM CHLORIDE Chemical Properties

Melting point:

268-270 °C

storage temp. 

Inert atmosphere,Room Temperature

form 

solid

color 

White to Almost white

Water Solubility 

very faint turbidity

Sensitive 

Hygroscopic

BRN 

6222047

InChIKey

ARPLQAMUUDIHIT-UHFFFAOYSA-M

CAS DataBase Reference

4336-70-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

37/39-26

RIDADR 

3276

WGK Germany 

3

RTECS 

TA2075000

HazardClass 

6.1

PackingGroup 

III

HS Code 

29319090

MSDS

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• Language:English Provider:ALFA

(CYANOMETHYL)TRIPHENYLPHOSPHONIUM CHLORIDE Usage And Synthesis

Chemical Properties

off-white crystalline powder

Uses

Reactant involved in:

• Condenation reactions
• Wittig reactions
• Synthesis of phosphonium-iodonium ylides
• Preparation of α,β-unsaturated esters, amides, and nitriles

reaction suitability

reaction type: C-C Bond Formation

Synthesis

The general procedure for the synthesis of cyanomethyltriphenylphosphonium chloride from chloroacetonitrile and triphenylphosphine was as follows: chloroacetonitrile (10 g, 0.132 mol) was added slowly and dropwise to a toluene solution (120 mL) of triphenylphosphine (23.5 g, 0.0895 mol), and the mixture was subsequently heated to reflux for 6 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, the solid product was collected by filtration and washed with ether (2 x 20 mL). The final cyanomethyltriphenylphosphonium chloride (15 g, 49.58% yield) was obtained as a white solid. The product was characterized by NMR hydrogen spectroscopy (400 MHz, DMSO): δ 8.02-7.97 (m, 3H), 7.90-7.79 (m, 12H), 5.94 (s, 1H), 5.90 (s, 1H); Liquid Chromatography-Mass Spectrometry (electrospray ionization, m/z): [M + H]+ = 301.7.

References

[1] European Journal of Medicinal Chemistry, 2013, vol. 68, p. 132 - 138
[2] Chemistry - A European Journal, 2013, vol. 19, # 7, p. 2442 - 2449
[3] Journal of Organic Chemistry, 1980, vol. 45, # 26, p. 5316 - 5319
[4] International Journal of Chemical Kinetics, 2006, vol. 38, # 8, p. 496 - 502
[5] Patent: WO2016/105485, 2016, A2. Location in patent: Paragraph 0158

(CYANOMETHYL)TRIPHENYLPHOSPHONIUM CHLORIDE(4336-70-3)Related Product Information

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