2-chloro-1,3,2-dioxaphospholane

• ChemBase ID: 91087
• Molecular Formular: C2H4ClO2P
• Molecular Mass: 126.478721
• Monoisotopic Mass: 125.96374368
• SMILES: P1(OCCO1)Cl
• Canonical SMILES: ClP1OCCO1
• InChI: InChI=1S/C2H4ClO2P/c3-6-4-1-2-5-6/h1-2H2
• InChIKey: OLSFRDLMFAOSIA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-chloro-1,3,2-dioxaphospholane
• IUPAC Traditional name: 2-chloro-1,3,2-dioxaphospholane
• Synonyms: 2-Chloro-1,3,2-dioxaphospholane; Ethylene Phosphorochloridite; Phosphorochloridous Acid Cyclic Ethylene Ester; Cyclic Phosphorochloridite Ethylene Glycol; Cyclic O,O-Ethylene Phosphorochloridite; 2-Chloro-1,3,2-dioxaphospholane; Ethylene chlorophosphite; Ethylene chlorophosphite; Ethylene glycol chlorophosphite; 2-Chloro-1,3,2-dioxaphospholane; Cyclic ethylene chlorophosphite; Cyclic ethylene phosphorochloridite; 氯代亚磷酸亚乙酯; 环氯亚磷酸乙烯酯; 2-氯-1,3,2-二氧磷杂环戊烷

Database IDs

• CAS Number: 822-39-9
• EC Number: 212-499-4
• MDL Number: MFCD00014511
• Beilstein Number: 506179
• PubChem SID: 24864368; 24854703; 162077791
• PubChem CID: 69973

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.1709
• LogD (pH = 7.4): 1.1709
• Log P: 1.1709
• Molar Refractivity: 25.0971 cm^3
• Polarizability: 9.880773 Å^3
• Polar Surface Area: 18.46 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Apperance: Clear Colourless Oil
• Boiling Point: 46-47°C/15mm; 62 °C/20 mmHg(lit.); 62°C/20mm; 62°C/20mm
• Flash Point: 186.8 °F; 86 °C; 86°C(186°F)
• Density: 1.415; 1.422 g/mL at 25 °C(lit.)
• Refractive Index: 1.4910; n20/D 1.489(lit.); n20/D 1.491

Safety Information

• Storage Warning: Highly reactive cyclic phosphitylating reagent which; Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 3264; UN3265
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 14-34; 14-34-37
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H314-H318-H227; H314-H335
• GHS Precautionary statements: P210-P260-P303+P361+P353-P305+P351+P338-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 3264 8/PG 2
• Supplemental Hazard Statements: Reacts violently with water.
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (GC); 97%
• Grade: purum
• Empirical Formula (Hill Notation): C2H4ClO2P

DETAILS

Apollo Scientific Ltd - OR6550T

Highly reactive cyclic phosphitylating reagent which provides fast coupling rates, & hydrolytic cleavage that occurs more readily than with acyclic analogs.

Sigma Aldrich - 391220

Packaging
5 mL in glass bottle
Application
Phosphitylating agent used in the synthesis of phosphocholines1,2 and spirophosphoranes.3

Sigma Aldrich - 24478

Other Notes
Versatile cyclic chlorophosphite. It reacts with alcohols to the triester which can be oxidized or thionated 1,2; Derivatizing agent for analyzing carbohydrates by decoupled 31P spectroscopy3

Toronto Research Chemicals - C365500

Highly reactive cyclic phosphitylating reagent which provides fast coupling rates, and hydrolytic cleavage occurs more readily than with acyclic analogs.

REFERENCES

• Bannwarth,W. & Kung, E.: Tetrahedron Lett., 30, 4219 (1989)
• Peptide coupling reagent via the mixed anhydride; see Appendix 6: J. Am. Chem. Soc., 72, 5491 (1950).
• In conjunction with triethyl phosphite, dehydrates primary carboxamides to nitriles, which has been applied in peptide chemistry: J. Am. Chem. Soc., 88, 2025 (1966).
• Used in the coupling of arylamines with CS₂ to give diarylthioureas: Rev. Roum. Chim., 29, 329 (1984).