5381-99-7

Basic information

• Product Name: 2-CHLORO-4H-1,3,2-BENZODIOXAPHOSPHORIN-4-ONE
• Synonyms: 2-CHLORO-1,3,2-BENZODIOXAPHOSPHORIN-4-ONE;2-CHLORO-4H-1,2,3-BENZODIOXAPHOSPHORIN-4-ONE;2-CHLORO-4H-1,3,2-BENZODIOXAPHOSPHORIN-4-ONE;VAN BOOM'S REAGENT;SALICYLCHLOROPHOSPHITE;ChloroHbenzodioxaphosphorinone;2-Chloro-4H-1,2,3-benzodioxaphosphorin-4-one 90%;2-CHLORO-4H-1,3,2-BENZODIOXAPHOSPHORIN-4-ONE 97%
• CAS NO: 5381-99-7
• Molecular Formula: C₇H₄ClO₃P
• Molecular Weight: 202.53
• Product Categories: Phospholipids - 13C & 2H;Biochemistry;Nucleosides, Nucleotides & Related Reagents;Phosphorylating and Phosphorothioating Agents;Phosphorylation;Protecting Agents, Phosphorylating Agents & Condensing Agents;Synthetic Organic Chemistry;Phosphorylating and Phosphitylating Agents
• Mol File: 5381-99-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 36-40 °C(lit.)
• Boiling Point: 127-128 °C11 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /solid
• Density: g/cm³
• Vapor Pressure: 0.0142mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: Soluble in acetonitrile, dichloromethane, tetrahydrofuron and di
• Stability: Water Sensitive
• BRN: 1311951
• CAS DataBase Reference: 2-CHLORO-4H-1,3,2-BENZODIOXAPHOSPHORIN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-4H-1,3,2-BENZODIOXAPHOSPHORIN-4-ONE(5381-99-7)
• EPA Substance Registry System: 2-CHLORO-4H-1,3,2-BENZODIOXAPHOSPHORIN-4-ONE(5381-99-7)

Safety Data

• Hazard Codes: C
• Statements: 14-34-37
• Safety Statements: 26-36/37/39-43-45
• RIDADR: UN 3261 8/PG 1
• WGK Germany: 3
• F: 3-10
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 5381-99-7(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline Solid

Uses

Different sources of media describe the Uses of 5381-99-7 differently. You can refer to the following data:
1. 2-Chloro-4H-1,3,2-benzodioxaphosphorin-4-one is a reagent used in phosphorylation and phosphitylation of alcohols and in the formation of H-phosphonates. It is also reactive cyclic phosphitylating reagent involved in fast coupling rates and hydrolytic cleavage more readily compare to that of a acyclic analog.
2. 2-Chloro-1,3,2-benzodioxaphosphorin-4-one is used as a reagent: In the phosphorylation and phosphitylation of alcohols. In the formation of H-phosphonates which are commonly utilized in the synthesis of nucleotides. To synthesize nucleoside triphosphates by treating with acyl protected nucleoside.

InChI:InChI=1/C7H4ClO3P/c8-12-10-6-4-2-1-3-5(6)7(9)11-12/h1-4H

Upstream product

• 127-09-3 sodium acetate 
• 69-72-7 salicylic acid 
• 7719-12-2 phosphorus trichloride 

Downstream Products

• 117779-58-5 2-((2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-benzo[1,3,2]dioxaphosphinin-4-one 
• 91303-31-0 C₃₄H₃₇O₈P 
• 140383-33-1 2-pentafluorophenoxy-4-oxo-5,6-benzo-1,3,2-dioxaphosphorinane 
• 110945-45-4 C₅₀H₄₄NO₁₃P 
• 207448-94-0 acetic acid 4-acetoxy-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5-(4-oxo-4H-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-tetrahydro-furan-3-yl ester 
• 207448-92-8 C₃₀H₂₃N₂O₁₁P 

Relevant articles and documents

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Synthesis and Biological Activity of 3,4,-Tri-О-Acetyl-N-Acetylglucosamine and Tetraacetylglucopyranose Conjugated with Alkyl Phosphates

Abstract: Conjugates of 3,4,6-tri-О-acetyl-N-acetylglucosamine and tetraacetyl glucopyranose with alkyl phosphates were synthesized. The dependence of their antibacterial and antituberculosis activities on the length of the alkyl substituent at the phosphate group was found. The conjugates with a decyl substituent exhibited in vitro the highest antituberculosis activity against Mycobacterium tuberculosis H37Rv (MIC 3?μg/mL) but the weakest effect towards Streptococcus aureus and Bacillus cereus (≤MIC 125 μg/mL). Vice versa, the conjugates with a cetyl substituent demonstrated the highest antibacterial activity in vitro towards S. aureus and B. cereus (MIC 16 μg/mL) but showed the lowest antituberculosis activity (MIC 12 μg/mL) among the compounds under study.

Preparation of a protected phosphoramidon precursor via an H-Phosphonate coupling strategy

The preparation of a phosphoramidon precursor is described using a phosphorus(III) coupling protocol.

One-pot synthesis of phosphonic acid diesters

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