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447536

Sigma-Aldrich

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

95%

Synonym(s):

Tetramethylethylene chlorophosphite

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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

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Certificates of Analysis (COA)

Lot/Batch Number
BGBC5233V
BGBC4277V
BGBC4314V
BGBC4061V
BGBC4060V

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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
One-pot synthesis of 2-deoxy-β-oligosaccharides
Pongdee R, et al.
Organic Letters, 3(22), 3523-3525 (2001)
Weisheng Yang et al.
International journal of biological macromolecules, 166, 1312-1319 (2020-11-09)
Most phenolic resins are synthesized with non-renewable petroleum-based phenol and formaldehyde, which have adverse effects on the environment and human health. To achieve green and sustainable production of phenolic resins, it is important to replace non-renewable toxic phenol and formaldehyde.
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Global Trade Item Number

SKUGTIN
447536-5G4061832288628
447536-1G4061838119834

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