2-chloro-2H-1,3,2-benzodioxaphosphole

• ChemBase ID: 151282
• Molecular Formular: C6H4ClO2P
• Molecular Mass: 174.521521
• Monoisotopic Mass: 173.96374368
• SMILES: c1ccc2c(c1)OP(O2)Cl
• Canonical SMILES: ClP1Oc2c(O1)cccc2
• InChI: InChI=1S/C6H4ClO2P/c7-10-8-5-3-1-2-4-6(5)9-10/h1-4H
• InChIKey: YUJYEGDMJZHLMY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-chloro-2H-1,3,2-benzodioxaphosphole
• IUPAC Traditional name: 2-chloro-1,3,2-benzodioxaphosphole
• Synonyms: o-Phenylene chlorophosphite; Chloro(1,2-phenylenedioxy)phosphine; Cyclic o-phenylene phosphorochloridite; Phosphorochloridous acid orthophenylene ester; Pyrocatechol phosphoryl chloride; 2-Chloro-1,3,2-benzodioxaphosphole; o-Phenylene phosphorochloridite; o-Phenylene Phosphorochloridite; 2-Chloro-4,5-benzo-1,3,2-dioxaphospholane; 1,2-Phenylene Phosphorochloridite; Catechyl phosphorus chloride; 1,2-Phenylene phosphorochloridite; 2-氯-1,3,2-苯并二氧环磷烯; 1,2-亚苯基-次氯酸化膦

Database IDs

• CAS Number: 1641-40-3
• EC Number: 216-690-3
• MDL Number: MFCD00005853
• Beilstein Number: 135455
• PubChem SID: 24849564; 162245438
• PubChem CID: 74232

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.6654625
• LogD (pH = 7.4): 2.6654994
• Log P: 2.6655
• Molar Refractivity: 40.5633 cm^3
• Polarizability: 15.609493 Å^3
• Polar Surface Area: 18.46 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Colourless Liquid Which Solidifies at Low Te
• Melting Point: 29-31°C; 30-35 °C(lit.); ca 30°C
• Boiling Point: 73-75°C/7mm; 80 °C/20 mmHg(lit.); 80°C/9mm
• Flash Point: >110°C(230°F); 110 °C; 230 °F
• Density: 1.464; 1.466 g/mL at 25 °C(lit.)
• Refractive Index: 1.5720; n20/D 1.571(lit.)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 34
• Safety Statements: 20-23-26-36/37/39-45; 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C6H4ClO2P

DETAILS

Sigma Aldrich - 155764

Packaging
10 g in glass bottle
Application

• Catalyst in synthesis of bakkane sesquiterpenes1
• Reactant in reversible halogen-halogen ligand substitution at room temperature, and in irreversible halogen-O substitution at higher temperatures2
• Reactant in preparation of gold(I) trimethoxybenzonitrile phosphine isolated precatalysts3
• Reactant for preparation of pyrroles by TMSOTf-catalyzed Arbuzov reaction4
• Phosphorylation agent5
• Reactant for reparation of vinyl-substituted spirophosphoranes and vinylphosphonates via Markovnikov addition6

Toronto Research Chemicals - P320000

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)
• Primary or secondary alcohols can be converted to the iodides via the phosphite esters and subsequent reaction with iodine: J. Org. Chem., 32, 4160 (1967). Reagent for the reduction of sulfoxides to sulfides: Synthesis, 262 (1976). Reactive phosphitylating agent: Tetrahedron Lett., 30, 4219 (1989).