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Sigma-Aldrich

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

95%

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Synonym(s):
Tetramethylethylene chlorophosphite
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.)

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

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1 of 4

This Item
391220362891249491
2-Chloro-1,3,2-dioxaphospholane 97%

391220

2-Chloro-1,3,2-dioxaphospholane

Diethylphosphoramidous dichloride 97%

362891

Diethylphosphoramidous dichloride

Tris(4-chlorophenyl)phosphine 95%

249491

Tris(4-chlorophenyl)phosphine

assay

95%

assay

97%

assay

97%

assay

95%

density

1.149 g/mL at 25 °C (lit.)

density

1.422 g/mL at 25 °C (lit.)

density

1.196 g/mL at 25 °C (lit.)

density

-

bp

81.5-82 °C/13 mmHg (lit.)

bp

62 °C/20 mmHg (lit.)

bp

179 °C (lit.)

bp

-

refractive index

n20/D 1.471 (lit.)

refractive index

n20/D 1.489 (lit.)

refractive index

n20/D 1.497 (lit.)

refractive index

-

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

signalword

Danger

hcodes

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

supp_hazards

Storage Class

8A - Combustible, corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


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Guo, Y.; Sulikowski, G. A.,
Journal of the American Chemical Society, 120, 1392-1392 (1998)
Kraft lignin-based rigid polyurethane foam
Li Y and Ragauskas AJ
J. Wood Chem. Technol., 32(3), 210-224 (2012)
Synthesis of complex carbohydrates and glycoconjugates: enzyme-based and programmable one-pot strategies.
K M Koeller et al.
Chemical reviews, 100(12), 4465-4494 (2001-12-26)
Characterization of CO2 precipitated Kraft lignin to promote its utilization
Nagy M, et al.
Green Chemistry, 12(1), 31-34 (2010)
Angelov, C. M.; Dahl, O.
Tetrahedron Letters, 24, 1643-1643 (1983)

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