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324124

Sigma-Aldrich

2-Chloro-1,3,2-benzodioxaphosphorin-4-one

95%

Synonym(s):

SalPCl, Salicyl chlorophosphite

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About This Item

Empirical Formula (Hill Notation):
C7H4ClO3P
CAS Number:
5381-99-7
Molecular Weight:
202.53
Beilstein:
1311951
MDL number:
MFCD00013353
UNSPSC Code:
12352005
PubChem Substance ID:
24859425
NACRES:
NA.22

Assay

95%

form

solid

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand

bp

127-128 °C/11 mmHg (lit.)

mp

36-40 °C (lit.)

functional group

phosphine

storage temp.

2-8°C

SMILES string

ClP1OC(=O)c2ccccc2O1

InChI

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

InChI key

BVOITXUNGDUXRW-UHFFFAOYSA-N

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Application

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.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Supplementary Hazards

EUH014

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

324124-BULK:
324124-25G:
324124-5G:
324124-VAR:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Buhr, C. A.; Matteucci, M. D.; Froehler, B. C.
Tetrahedron Letters, 40, 8969-8969 (1999)
Jacek Stawinski et al.
Accounts of chemical research, 35(11), 952-960 (2002-11-20)
The biological importance and practical significance of phosphate esters and their analogues have been the major driving forces for research in various areas of synthetic organic phosphorus chemistry. In this Account, the authors' studies on the development of a comprehensive
Byun, H.-S.; Erukulla, R. K.; Bittman, R.
The Journal of Organic Chemistry, 59, 6495-6495 (1994)
Jesse J Chen et al.
PloS one, 4(3), e4949-e4949 (2009-03-24)
Glycerol nucleic acid (GNA) has an acyclic phosphoglycerol backbone repeat-unit, but forms stable duplexes based on Watson-Crick base-pairing. Because of its structural simplicity, GNA is of particular interest with respect to the possibility of evolving functional polymers by in vitro

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