447536

Sigma-Aldrich

2-Chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane

95%

Empirical Formula (Hill Notation):
C6H12ClO2P
CAS Number:
Molecular Weight:
182.59
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

assay

95%

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

refractive index

n20/D 1.471 (lit.)

bp

81.5-82 °C/13 mmHg (lit.)

density

1.149 g/mL at 25 °C (lit.)

functional group

phosphine

SMILES string

CC1(C)OP(Cl)OC1(C)C

InChI

1S/C6H12ClO2P/c1-5(2)6(3,4)9-10(7)8-5/h1-4H3

InChI key

WGPCXYWWBFBNSS-UHFFFAOYSA-N

Application

2-Chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane (TMDP) can be used:
  • As a reagent for the phosphitylation of alcohols and heteroatomic nucleophiles, resulting in the formation of useful glycosyl donors and ligands.
  • As a phosphitylation reagent to derivatize lignin samples for 31P NMR analysis.

Packaging

1, 5 g in glass bottle

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Supp Hazards

EUH014

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 3265 8 / PGII

WGK Germany

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

One-pot synthesis of 2-deoxy-β-oligosaccharides
Pongdee R, et al.
Organic Letters, 3(22), 3523-3525 (2001)
Angelov, C. M.; Dahl, O.
Tetrahedron Letters, 24, 1643-1643 (1983)
Lucía Penín et al.
Molecules (Basel, Switzerland), 25(2) (2020-01-24)
Eucalyptus nitens wood samples were subjected to consecutive stages of hydrothermal processing for hemicellulose solubilization and delignification with an ionic liquid, i.e., either 1-butyl-3-methylimidazolium hydrogen sulfate or triethylammonium hydrogen sulfate. Delignification experiments were carried out a 170 C for 10-50...
Kraft lignin-based rigid polyurethane foam
Li Y and Ragauskas AJ
J. Wood Chem. Technol., 32(3), 210-224 (2012)
Guo, Y.; Sulikowski, G. A.,
Journal of the American Chemical Society, 120, 1392-1392 (1998)

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