diethyl (chloromethyl)phosphonate

• ChemBase ID: 74916
• Molecular Formular: C5H12ClO3P
• Molecular Mass: 186.573741
• Monoisotopic Mass: 186.02125855
• SMILES: P(=O)(OCC)(OCC)CCl
• Canonical SMILES: ClCP(=O)(OCC)OCC
• InChI: InChI=1S/C5H12ClO3P/c1-3-8-10(7,5-6)9-4-2/h3-5H2,1-2H3
• InChIKey: MZBIWKMCTWJLPT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl (chloromethyl)phosphonate
• IUPAC Traditional name: diethyl chloromethylphosphonate
• Synonyms: Chloromethylphosphonic acid diethyl ester; NSC 67753; Diethyl chloromethylphosphonate; (Chloromethyl)phosphonic acid diethyl ester; Diethyl (chloromethyl)phosphonate; 氯甲基膦酸二乙酯

Database IDs

• CAS Number: 3167-63-3
• EC Number: 221-632-5
• MDL Number: MFCD00010189
• Beilstein Number: 1363361
• PubChem SID: 162039834; 24855986
• PubChem CID: 76633

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.5542176
• LogD (pH = 7.4): 1.5542176
• Log P: 1.5542176
• Molar Refractivity: 40.3508 cm^3
• Polarizability: 16.600437 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 109-110 °C/10 mmHg(lit.); 109-110°C/10mm
• Flash Point: 186.8 °F; 187 °F; 86 °C
• Density: 1.2; 1.2 g/mL at 25 °C(lit.)
• Refractive Index: 1.437; n20/D 1.437; n20/D 1.437(lit.)

Safety Information

• Storage Warning: Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (GC); 97%
• Grade: purum
• Linear Formula: ClCH2PO(OC2H5)2

DETAILS

Sigma Aldrich - 263613

Packaging
1 mL in glass bottle
Application
Reactant involved in:
• Subsequent alkylation after nucleophilic substitution1
• One-pot alkylation-boration of α-haloalkylphosphonates2
• Synthesis of cyclpentane and pyrrolidine derivatives via regioselective insertion reactions3
• Phosphorylation leading to P-containing cyclopropanes4
• Wadsworth-Emmons reactions5
• Ring expansion of zircnacycles via carbenoid insertion6

Sigma Aldrich - 25030

Caution
may discolor to brown on storage
Application
Reactant involved in:
• Subsequent alkylation after nucleophilic substitution1
• One-pot alkylation-boration of α-haloalkylphosphonates2
• Synthesis of cyclpentane and pyrrolidine derivatives via regioselective insertion reactions3
• Phosphorylation leading to P-containing cyclopropanes4
• Wadsworth-Emmons reactions5
• Ring expansion of zircnacycles via carbenoid insertion6