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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)
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
T Tanaka et al.
Nucleic acids research, 10(10), 3249-3260 (1982-05-25)
A simple procedure is described for synthesis of oligonucleotides by phosphate chemistry. Chains can be constructed rapidly with minimal equipment (a syringe and reagent bottles). The method is illustrated by synthesis of d-TGCAGGTT. Pertinent supporting data on the effect of
Synthetic Communications, 22, 289-289 (1992)
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
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