bis(propan-2-yl) (cyanomethyl)phosphonate

• ChemBase ID: 137234
• Molecular Formular: C8H16NO3P
• Molecular Mass: 205.191301
• Monoisotopic Mass: 205.08678001
• SMILES: CC(C)OP(=O)(CC#N)OC(C)C
• Canonical SMILES: CC(OP(=O)(CC#N)OC(C)C)C
• InChI: InChI=1S/C8H16NO3P/c1-7(2)11-13(10,6-5-9)12-8(3)4/h7-8H,6H2,1-4H3
• InChIKey: MQDIIJHQSUNBKA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(propan-2-yl) (cyanomethyl)phosphonate
• IUPAC Traditional name: diisopropyl cyanomethylphosphonate
• Synonyms: Diisopropyl (cyanomethyl)phosphonate; Cyanomethylphosphonic acid diisopropyl ester; Diisopropyl cyanomethylphosphonate; 二异丙基(氰甲基)膦酸酯; 氰甲基磷酸二异丙酯

Database IDs

• CAS Number: 21658-95-7
• EC Number: 244-511-9
• MDL Number: MFCD00009812
• Beilstein Number: 1946176
• PubChem SID: 24854808; 162231499
• PubChem CID: 88997

CALCULATED PROPERTIES

• Acid pKa: 12.055288
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.99616474
• LogD (pH = 7.4): 0.9961553
• Log P: 0.99616486
• Molar Refractivity: 49.9127 cm^3
• Polarizability: 20.051065 Å^3
• Polar Surface Area: 59.32 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 108-110 °C/0.08 mmHg(lit.); 108-110°C/0.08m
• Flash Point: >110°C(230°F); 113 °C; 235.4 °F
• Density: 1.039; 1.039 g/mL at 25 °C(lit.)
• Refractive Index: 1.4295; n20/D 1.428(lit.)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Toxic (T)
• UN Number: 2922; UN2927
• German water hazard class: 3
• Hazard Class: 6.1; 8
• Packing Group: 2; II
• Risk Statements: 23/24/25-34
• Safety Statements: 23-26-36/37/39-45; 26-27-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330-H314-H318; H301-H311-H314-H331
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P361-P405-P501A; P261-P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2922 8/PG 2

Product Information

• Purity: 97%
• Linear Formula: NCCH2P(O)[OCH(CH3)2]2

REFERENCES

• Precursor of substituted acrylonitriles by Horner-Wadsworth-Emmons olefination (see Appendix 1), giving a higher proportion of the (Z)-product than Diethyl cyanomethylphosphonate, A10218: Synth. Commun., 10, 509 (1980).