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235229

Sigma-Aldrich

Methyl dichlorophosphite

technical grade

Synonym(s):

Methyl phosphorodichloridite

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About This Item

Linear Formula:
CH3OPCl2
CAS Number:
3279-26-3
Molecular Weight:
132.91
Beilstein:
1697452
EC Number:
221-915-3
MDL number:
MFCD00000524
UNSPSC Code:
12352100
PubChem Substance ID:
24854089
NACRES:
NA.22

grade

technical grade

Quality Level

100

form

liquid

refractive index

n20/D 1.474 (lit.)

bp

93-95 °C (lit.)

mp

−91 °C (lit.)

density

1.376 g/mL at 20 °C (lit.)

SMILES string

COP(Cl)Cl

InChI

1S/CH3Cl2OP/c1-4-5(2)3/h1H3

InChI key

HCSDJECSMANTCX-UHFFFAOYSA-N

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Application

Methyl dichlorophosphite has been employed in the preparation of:
  • phosphonamidate- and phosphonate-linked phosphonopeptides
  • 2-(2-iodophenyl)ethyl methyl phosphite derivative of an alcohol
  • deoxyoligonucleotides on a polymer support
  • cis- and trans-2-oxo-2-propionyl-1,3,2-oxazaphosphorinane
  • phosphorodichloridothioates
  • oxazaphosphorinanes

accessory

Product No.
Description
Pricing

Signal Word

Danger

Hazard Statements

H226 - H314 - H335

Hazard Classifications

Flam. Liq. 3 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH014

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

77.0 °F - closed cup

Flash Point(C)

25 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Synthesis and enantioselective aldol reaction of a chiral 2-oxo-2-propionyl-1, 3, 2-oxazaphosphorinane.
Gordon NJ and Evans Jr SA.
The Journal of Organic Chemistry, 58(20), 5295-5297 (1993)
Synthesis of deoxyoligonucleotides on a polymer support.
Matteucci MD and Caruthers MH.
Journal of the American Chemical Society, 103(11), 3181-3191 (1981)
Nanyan Fu et al.
Journal of peptide science : an official publication of the European Peptide Society, 12(4), 303-309 (2005-10-26)
A direct method for the preparation of phosphonamidate- and phosphonate-linked phosphonopeptides has been developed. Using this method, both phosphonopeptides were prepared in acceptable yields directly from simple and commercially available chemicals in one-pot reactions of benzyl carbamate, aldehydes, and methyl
Liming Zhang et al.
Journal of the American Chemical Society, 126(41), 13190-13191 (2004-10-14)
A highly efficient, two-step sequence method for the deoxygenation of hydroxyl groups has been developed. The method involves the preparation of the 2-(2-iodophenyl)ethyl methyl phosphite derivative of an alcohol using methyl dichlorophosphite and 2-(2-iodophenyl)ethanol. Treatment of the phosphite intermediate with
Synthetic Communications, 22, 289-289 (1992)
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