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Key Documents

235237

Sigma-Aldrich

2-Chlorophenyl phosphorodichloridate

99%

Synonym(s):

2-Chlorophenyl dichlorophosphate

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About This Item

Linear Formula:
Cl2P(O)OC6H4Cl
CAS Number:
Molecular Weight:
245.43
Beilstein:
911009
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

99%

form

liquid

refractive index

n20/D 1.538 (lit.)

bp

135-137 °C/12 mmHg (lit.)

density

1.491 g/mL at 25 °C (lit.)

SMILES string

Clc1ccccc1OP(Cl)(Cl)=O

InChI

1S/C6H4Cl3O2P/c7-5-3-1-2-4-6(5)11-12(8,9)10/h1-4H

InChI key

VLDPXPPHXDGHEW-UHFFFAOYSA-N

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Application

2-Chlorophenyl phosphorodichloridate has been used in the preparation of:
  • mononucleotide building blocks
  • oligonucleotides and oligonucleotide phosphorothioates in solution

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

221.0 °F - closed cup

Flash Point(C)

105 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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A new approach to the synthesis of oligonucleotides and their phosphorothioate analogues in solution.
Reese CB and Song Q.
Bioorganic & Medicinal Chemistry Letters, 7(21), 2787-2792 (1997)
Dealkylation of nucleoside arylmethyl 2-chlorophenyl phosphates: the 2, 4-dinitrobenzyl protecting group.
Christadoulou C and Reese CB.
Tetrahedron Letters, 24(9), 951-954 (1983)
Stereoselective chain elongation at C-3 of cysteine through 2,3-dihydrothiazoles, without racemization. Preparation of 2-amino-5-hydroxy-3-mercaptoalkanoic acid derivatives
Andre Jeanguenat and Dieter Seebach
Journal of the Chemical Society. Perkin Transactions 1, 2291-2298 (1991)

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