Diethyl cyanomethylphosphonate CAS 2537-48-6
Introduction：Basic information about Diethyl cyanomethylphosphonate CAS 2537-48-6, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Diethyl cyanomethylphosphonate Basic information
| Product Name: | Diethyl cyanomethylphosphonate |
| Synonyms: | (Cyanomethyl)diethoxyphosphine oxide;2-(Diethylphosphonyl)acetonitrile;Diethyl cyanomethanephosphonate;Phosphonic acid, (cyanomethyl)-, diethyl ester;Cyanomethylphosphonic acid diethyl ester~Diethyl phosphonoacetonitrile;Diethylcyanomethylphosphonate,98+%;Diethyl (cyanomethyl)phosphonate 98%;LABOTEST-BB LT00233137 |
| CAS: | 2537-48-6 |
| MF: | C6H12NO3P |
| MW: | 177.14 |
| EINECS: | 219-806-0 |
| Product Categories: | Pyridines;Wittig Reagents;Phosphorus compounds;Horner-Emmons Reaction;Synthetic Organic Chemistry;Wittig & Horner-Emmons Reaction;2537-48-6 |
| Mol File: | 2537-48-6.mol |
Diethyl cyanomethylphosphonate Chemical Properties
| Boiling point | 101-102 °C0.4 mm Hg(lit.) |
| density | 1.095 g/mL at 25 °C(lit.) |
| refractive index | n |
| 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) |
Safety Information
| Hazard Codes | Xi,Xn,C |
| Risk Statements | 38-36/37/38-20/21/22-34-36/38 |
| Safety Statements | 26-28-36/37/39-23-45-27-36/37-9 |
| RIDADR | UN 1760 8/PG 2 |
| WGK Germany | 3 |
| Hazard Note | Irritant |
| HazardClass | 6.1 |
| PackingGroup | III |
| HS Code | 29310095 |
| Storage Class | 10 - Combustible liquids |
| 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 | 107-14-2 122-52-1 2537-48-6 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
| Raw materials | Chloroacetonitrile-->Triethyl phosphite |
| Preparation Products | 2-Aminoquinoline-->1-BENZOFURAN-3-YLACETONITRILE-->2-(2,3-DIHYDRO-1BENZENESULFONYL-PYRROLO[2,3-B]PYRIDIN-3-YL)ETHANAMINE-->4-FLUOROCINNAMONITRILE-->2-(2,3-DIHYDRO-1-BENZENESULFONYL-PYRROLO[2,3-B]PYRIDIN-3-YL)ACETONITRILE-->3-(cyanomethylene)cyclobutane-1-carbonitrile-->(Z)-3-(1H-indol-3-yl)acrylonitrile-->Phosphonic acid, (1-cyano-3-hydroxypropyl)-, diethyl ester (9CI)-->2-(1-benzylpiperidin-4-ylidene)acetonitrile-->3-CYCLOPENTYLACRYLONITRILE |
