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

Description

2-Chloro-4H-1,3,2-benzodioxaphosphorin-4-one is a reactive cyclic phosphitylating reagent known for its fast coupling rates and hydrolytic cleavage, making it a valuable compound in various chemical reactions and synthesis processes.

Uses

Used in Pharmaceutical Industry:
2-Chloro-4H-1,3,2-benzodioxaphosphorin-4-one is used as a reagent for the phosphorylation and phosphitylation of alcohols, which is crucial in the synthesis of nucleotides and nucleoside triphosphates. These compounds play a vital role in the development of pharmaceuticals, particularly in the creation of new drugs and therapies.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-Chloro-4H-1,3,2-benzodioxaphosphorin-4-one is utilized for the formation of H-phosphonates. These compounds are essential building blocks in the synthesis of various organic and inorganic molecules, contributing to the advancement of materials science and the development of new chemical products.
Used in Research and Development:
2-Chloro-4H-1,3,2-benzodioxaphosphorin-4-one is also employed in research and development settings, where its unique properties and reactivity are harnessed to explore new chemical reactions and mechanisms. This contributes to the expansion of scientific knowledge and the discovery of innovative applications in various industries.

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

Upstream product

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

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 
• 207448-92-8 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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