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Merck

324124

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

95%, solid

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
NACRES:
NA.22
PubChem Substance ID:
24859425
UNSPSC Code:
12352005
MDL number:
MFCD00013353
Beilstein/REAXYS Number:
1311951

Key Documents

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Product Name

2-Chloro-1,3,2-benzodioxaphosphorin-4-one, 95%

InChI

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

SMILES string

ClP1OC(=O)c2ccccc2O1

InChI key

BVOITXUNGDUXRW-UHFFFAOYSA-N

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

Quality Level

200

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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

signalword

Danger

hcodes

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

supp_hazards

EUH014

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000519547
0000519550
0000519550
0000519547
0000493340

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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)
Nucleoside Triphosphates-From Synthesis to Biochemical Characterization
Hollenstein M, et al.
Journal of Visualized Experiments, (86) (2014)
Cyclotriphosphate: A brief history, recent developments, and perspectives in synthesis
Bezold D, et al.
Chemistry?A European Journal , 26(11), 2298-2308 (2020)
Buhr, C. A.; Matteucci, M. D.; Froehler, B. C.
Tetrahedron Letters, 40, 8969-8969 (1999)
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