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

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

signalword

Danger

hcodes

hazcat

Eye Dam. 1 - Skin Corr. 1B

Supp Hazards

EUH014

storage_class_code

8A - Combustible, corrosive hazardous materials

WGK Germany

WGK 3

Flash Point F

235.4 °F - closed cup

Flash Point C

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Ethanol organosolv lignin-based rigid polyurethane foam reinforced with cellulose nanowhiskers
Li Y and Ragauskas AJ
Royal Society of Chemistry Advances, 2(8), 3347-3351 (2012)
Nontemplate-dependent polymerization processes: polyhydroxyalkanoate synthases as a paradigm
Stubbe J, et al.
Annual Review of Biochemistry, 74(22), 433-480 (2005)
Zafer Söyler et al.
ChemSusChem, 10(1), 182-188 (2016-11-23)
The transesterification of maize starch with olive oil or high oleic sunflower oil was studied under homogeneous conditions in the presence of 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as catalyst. Most importantly, this method used two renewable resources directly, without any pretreatment or derivatization...
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...
Angelov, C. M.; Dahl, O.
Tetrahedron Letters, 24, 1643-1643 (1983)

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