Skip to Content
Merck
All Photos(5)

Key Documents

View All Documentation

447536

Sigma-Aldrich

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

95%

Synonym(s):

Tetramethylethylene chlorophosphite

Sign Into View Organizational & Contract Pricing
All Photos(5)

About This Item

Empirical Formula (Hill Notation):
C6H12ClO2P
CAS Number:
14812-59-0
Molecular Weight:
182.59
MDL number:
MFCD00274239
UNSPSC Code:
12352005
PubChem Substance ID:
24868346
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.)

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.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Supplementary Hazards

EUH014

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000409133
0000409117
0000404938
0000404937
0000368006

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Nontemplate-dependent polymerization processes: polyhydroxyalkanoate synthases as a paradigm
Stubbe J, et al.
Annual Review of Biochemistry, 74(22), 433-480 (2005)
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
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
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)
Guo, Y.; Sulikowski, G. A.,
Journal of the American Chemical Society, 120, 1392-1392 (1998)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service