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| | (Cyanomethyl)triphenylphosphonium chloride Basic information |
| | (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 | | 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 | | SMILES | [Cl-].N#CC[P+](c1ccccc1)(c2ccccc2)c3ccccc3 | | CAS DataBase Reference | 4336-70-3(CAS DataBase Reference) |
| 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 | | Storage Class | 11 - Combustible Solids |
| | (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 Preparation Products And Raw materials |
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