| Identification | More | [Name]
(CYANOMETHYL)TRIPHENYLPHOSPHONIUM CHLORIDE | [CAS]
4336-70-3 | [Synonyms]
(CYANOMETHYL)TRIPHENYLPHOSPHONIUM CHLORIDE
(cyanomethyl)triphenyl-phosphoniuchloride
Cyanomethyl triphenylphosphonium chloride, 98+%
Triphenyl(cyanomethyl)phosphonium·chloride | [EINECS(EC#)]
224-383-0 | [Molecular Formula]
C20H17ClNP | [MDL Number]
MFCD00031672 | [Molecular Weight]
337.78 | [MOL File]
4336-70-3.mol |
| Chemical Properties | Back Directory | [Appearance]
off-white crystalline powder | [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 Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
3276 | [WGK Germany ]
3 | [RTECS ]
TA2075000 | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29319090 |
| Hazard Information | Back Directory | [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 |
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