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| | Diethyl cyanomethylphosphonate Basic information |
| | Diethyl cyanomethylphosphonate Chemical Properties |
| Boiling point | 101-102 °C0.4 mm Hg(lit.) | | density | 1.095 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.434(lit.) | | Fp | >230 °F | | storage temp. | Inert atmosphere,2-8°C | | solubility | Chloroform (Soluble), Methanol (Slightly) | | form | Liquid | | Specific Gravity | 1.1261.095 | | color | Clear colorless to light yellow | | Water Solubility | Miscible with water, chloroform, terahydrofuran, ethyl acetate and methylene chloride. | | BRN | 1772981 | | InChI | InChI=1S/C6H12NO3P/c1-3-9-11(8,6-5-7)10-4-2/h3-4,6H2,1-2H3 | | InChIKey | KWMBADTWRIGGGG-UHFFFAOYSA-N | | SMILES | P(CC#N)(=O)(OCC)OCC | | CAS DataBase Reference | 2537-48-6(CAS DataBase Reference) | | NIST Chemistry Reference | Diethyl cyanomethylphosphonate(2537-48-6) |
| | Diethyl cyanomethylphosphonate Usage And Synthesis |
| Chemical Properties | clear colorless to light yellow liquid | | Uses | Wittig reagent. | | Uses | Diethyl cyanomethyl phosphonate is used as an intermediate in Horner-Emmons reaction for the synthesis of substituted nitriles and their amide and heterocyclic derivatives. It is known as a modified Wittig reagent used in the preparation of alpha, beta-unsaturated nitriles from ketones or aldehydes like 3-hydroxy-3-methylbutanal. It reacts with epoxides and nitrones to prepare cyano-substituted cyclopropanes and aziridines respectively. It is actively involved in the synthesis of alpha-arylated alkanenitriles via reaction with aryl iodides in presence of CuI. | | Biological Functions |
Diethyl cyanomethylphosphonate can be used to inhibit and/0r prevent the growth of undesirable algae, bacteria, fungi, yeast, and other microorganisms.
| | General Description | Diethyl cyanomethylphosphonate is a useful chemical and medical intermediate, which can be used as raw material to synthesize nitrogen-haloamine precursor AEP-ADCT containing triazine-phosphate group | | reaction suitability | reaction type: C-C Bond Formation | | Synthesis | The general procedure for the synthesis of diethyl cyanomethylphosphonate from chloroacetonitrile and triethyl phosphite is as follows: 677.5 g (4.0 mol) of triethyl phosphite is heated to 150 °C. At 150 °C, 152.4 g (2.0 mol) of chloroacetonitrile was slowly added dropwise, and the dropwise process lasted for 2 hours (during which the exhaust gas produced was chloroethane). After the dropwise addition was completed, the reaction mixture was continued to be stirred at 150 °C for 2 hours (until the gas escape stopped completely). Upon completion of the reaction, the mixture was distilled under reduced pressure using a small Vigreux fractionation column (height 10 cm). The fraction with a boiling range of 110-139 °C was collected at a reduced pressure of 1 mbar, which was the target product diethyl cyanomethyl phosphate. The product yield was 99% in chloroacetonitrile (based on GC area percentage). | | References | [1] Patent: WO2005/63780, 2005, A1. Location in patent: Page/Page column 13
[2] Heterocycles, 2014, vol. 89, # 2, p. 375 - 397
[3] Phosphorus, Sulfur and Silicon and Related Elements, 2000, vol. 159, p. 37 - 46
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 433 - 436
[5] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1982, p. 25 - 30 |
| | Diethyl cyanomethylphosphonate Preparation Products And Raw materials |
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