diethyl (cyanomethyl)phosphonate

• ChemBase ID: 91244
• Molecular Formular: C6H12NO3P
• Molecular Mass: 177.138141
• Monoisotopic Mass: 177.05547988
• SMILES: P(=O)(CC#N)(OCC)OCC
• Canonical SMILES: CCOP(=O)(CC#N)OCC
• InChI: InChI=1S/C6H12NO3P/c1-3-9-11(8,6-5-7)10-4-2/h3-4,6H2,1-2H3
• InChIKey: KWMBADTWRIGGGG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl (cyanomethyl)phosphonate
• IUPAC Traditional name: diethyl cyanomethylphosphonate
• Synonyms: Diethyl phosphonoacetonitrile; (Diethylphosphono)acetonitrile; (Diethoxyphosphoryl)acetonitrile; Diethyl (cyanomethyl)phosphonate 98%; Cyanomethylphosphonic acid diethyl ester; Diethyl cyanomethylphosphonate; (Diethoxyphosphinyl)acetonitrile; Diethyl Cyanomethanephosphonate; O,O-Diethyl (Cyanomethyl)phosphonate; NSC 407826; Diethyl Cyanomethylphosphonate; P-(Cyanomethyl)phosphonic Acid Diethyl Ester; (Cyanomethyl)diethoxyphosphine Oxide; (Diethylphosphono)acetonitrile; DIETHYL CYANOMETHYL PHOSPHATE; diethyl (cyanomethyl)phosphonate; 氰甲基磷酸二乙酯; 二乙基氰甲基磷酸酯; 氰甲基膦酸二乙酯; 氰甲基膦酸二乙酯; 二乙基氰甲基磷酸酯

Database IDs

• CAS Number: 2537-48-6
• EC Number: 219-806-0
• MDL Number: MFCD00001893
• Beilstein Number: 1772981
• PubChem SID: 24894272; 162077948
• PubChem CID: 75676

CALCULATED PROPERTIES

• Acid pKa: 12.055647
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.17517574
• LogD (pH = 7.4): 0.17516631
• Log P: 0.17517588
• Molar Refractivity: 41.0751 cm^3
• Polarizability: 16.410683 Å^3
• Polar Surface Area: 59.32 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Tetrahydrofuran
• Apperance: Clear Oil
• Boiling Point: 101-102 °C/0.4 mmHg(lit.); 101-102°C/0.4mm; 132-135°C/1.2mm
• Flash Point: >110°C(230°F); 113 °C; 113°C; 235.4 °F
• Density: 1.094; 1.095; 1.095 g/mL at 25 °C(lit.)
• Refractive Index: 1.4330; n20/D 1.434; n20/D 1.434(lit.)

Safety Information

• Storage Warning: Corrosive/Irritant
• European Hazard Symbols: X; Irritant (Xi)
• UN Number: 1760; UN3278
• German water hazard class: 3
• Hazard Class: 6.1; 8
• Packing Group: 2; III
• Risk Statements: 20/21/22-36/38; 38
• Safety Statements: 26-28; 9-23-26-36/37
• TSCA Listed: 否
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315; H331-H302-H312-H315-H319
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1760 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (GC); 98%; 98+%
• Grade: purum
• Linear Formula: NCCH2PO(OC2H5)2

DETAILS

MP Biomedicals - 05206945

MP Biomedicals Rare Chemical collection

Sigma Aldrich - D91705

Packaging
10, 50 g in glass bottle

Sigma Aldrich - 28503

Other Notes
Horner-Wittig reagent1

Toronto Research Chemicals - D444165

Wittig reagent.

REFERENCES

• Laine, D., et al.: J. Med. Chem., 52, 5241 (2009)
• Nakao, A., et al.: Bioorg. Med. Chem. Lett., 19, 4607 (2009)
• Arakawa, Y., et al.: Chem. Pharm. Bull., 57, 167 (2009)
• The active methylene group can be monoalkylated under phase transfer conditions with alkyl iodides or allylic or benzylic bromides: Synthesis, 516 (1975). Use of alumina as base leads predominantly to the Knoevenagel product rather than the Wadsworth-Emmons: Tetrahedron, 41, 1259 (1985).
• Horner-Wadsworth-Emmons olefination converts carbonyl compounds to substituted acrylonitriles: J. Am. Chem. Soc., 83, 1733 (1961); J. Org. Chem., 30, 505 (1965). LiOH has been found to be an effective base for this reaction: Tetrahedron Lett., 44, 1333 (2003). See Appendix 1. See also 3-Coumaranone, A10202.