diethyl chlorophosphonite

• ChemBase ID: 104913
• Molecular Formular: C4H10ClO2P
• Molecular Mass: 156.547761
• Monoisotopic Mass: 156.01069387
• SMILES: CCOP(Cl)OCC
• Canonical SMILES: CCOP(OCC)Cl
• InChI: InChI=1S/C4H10ClO2P/c1-3-6-8(5)7-4-2/h3-4H2,1-2H3
• InChIKey: TXHWYSOQHNMOOU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl chlorophosphonite
• IUPAC Traditional name: ethyl phosphorochloridite
• Synonyms: Diethyl chlorophosphonite; Diethyl phosphorochloridite; Diethyl chlorophosphite; Ethyl phosphorochloridite; DIETHYL CHLOROPHOSPHITE; 二乙基氯代磷酸酯; 氯亚磷酸二乙酯; 二乙基亚磷酰氯; 氯代亚磷酸二乙酯

Database IDs

• CAS Number: 589-57-1
• EC Number: 209-652-2
• MDL Number: MFCD00009074
• Beilstein Number: 1098392
• Merck Index: 143841
• PubChem SID: 162093074; 24859281; 24894269
• PubChem CID: 68530

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.0337
• LogD (pH = 7.4): 2.0337
• Log P: 2.0337
• Molar Refractivity: 36.5633 cm^3
• Polarizability: 14.173006 Å^3
• Polar Surface Area: 18.46 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 153-155 °C(lit.); 153-155°C; 56-57.5 °C/30 mmHg(lit.); 56-57.5°C @ 30 mm Hg
• Flash Point: 1 °C; 1.1°C; 25°C(77°F); 33.8 °F
• Density: 1.082; 1.082 g/ml; 1.089 g/mL at 20 °C(lit.)
• Refractive Index: 1.4375; n20/D 1.434(lit.); n20/D 1.437

Safety Information

• Storage Condition: 2-8°C
• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C); Flammable (F)
• UN Number: 2924; UN2920
• German water hazard class: 3
• Hazard Class: 3; 8
• Packing Group: 2; II
• Australian Hazchem: 3WE
• Risk Statements: 10-14-34; 11-14-34-37; R:11-14-34
• Safety Statements: 26-36/37/39-45; 7/8-16-26-36/37/39-45; S:16-27/28-30-36/37/39-45
• EU Classification: FC
• EU Hazard Identification Number: 8A
• Emergency Response Guidebook(ERG) Number: 132
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H314-H335; H314-H318-H226
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P210-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 2924 3/PG 2
• Supplemental Hazard Statements: Reacts violently with water.
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (GC); 95%; 97%
• Grade: technical
• Linear Formula: (C2H5O)2PCl

DETAILS

MP Biomedicals - 02157685

(Ethyl phosphorochloridite)

Sigma Aldrich - D91659

Packaging
5, 25, 100 g in glass bottle

REFERENCES

• Reacts readily with nucleophiles, e.g. amines, alcohols or organometallic species, with the introduction of a phosphorus substituent. The phosphorylation of OH groups has been brought about by treatment with the reagent followed by oxidation of the P(III) product to P(V) with, e.g. iodine: Synth. Commun., 12, 821 (1982); Synthesis, 572 (1986). The chlorophosphite has the advantage of greater reactivity over one-step phosphorylation reagents, e.g. Diphenyl phosphorochloridate, A13546.
• Reagent for peptide coupling: J. Am. Chem. Soc., 74, 5304, 5309 (1952); see Appendix 6. Also useful, in the presence of TMS-OTf, in glycosidic couplings: Tetrahedron Lett., 33, 6123 (1992).
• In the presence of N-ethyldiisopropylamine, reduces both aryl and alkyl nitro compounds to amines: J. Org. Chem., 63, 393 (1998). The reagent also effects dehydration of aldoximes to nitriles, deoxygenation of N-oxides and sulfoxides, and conversion of epoxides to chlorohydrins can also be effected: J. Org. Chem., 67, 711 (2002).