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81801

Sigma-Aldrich

Propylphosphonic anhydride solution

technical, ~50% in DMF

Synonym(s):

1-Propanephosphonic anhydride solution, 2,4,6-Tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide solution, PPACA, T3P®

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About This Item

Empirical Formula (Hill Notation):
C9H21O6P3
CAS Number:
68957-94-8
Molecular Weight:
318.18
Beilstein/REAXYS Number:
5079255
MDL number:
MFCD00006583
UNSPSC Code:
12352100
PubChem Substance ID:
57652890
NACRES:
NA.22

grade

technical

Quality Level

100

form

solution

concentration

~50% in DMF

SMILES string

CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1

InChI

1S/C9H21O6P3/c1-4-7-16(10)13-17(11,8-5-2)15-18(12,14-16)9-6-3/h4-9H2,1-3H3

InChI key

PAQZWJGSJMLPMG-UHFFFAOYSA-N

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General description

Propylphosphonic anhydride is a highly reactive cyclic anhydride that is commonly used as a coupling agent and water scavenger.

Application

Coupling reagent for peptide synthesis; Preparation of other amides; Synthesis of esters (depsipeptides)

Features and Benefits

Some of its unique features include:
  • Broad functional group tolerance
  • Low epimerization tendency
  • By-products are water-soluble
  • High yield and purity


Legal Information

T3P is a registered trademark of Archimica GmbH

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Danger

Hazard Classifications

Eye Dam. 1 - Met. Corr. 1 - Repr. 1B - Skin Corr. 1B - Skin Sens. 1

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 2

flash_point_f

143.6 °F

flash_point_c

62 °C

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF3569
BCCD2461
BCCC3125
BCBW0155
BCBT8688

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H. Kessler et al.
Liebigs Ann. Chem., 1-1 (1986)
H. Wissmann
Phosph. Sulfur Relat. Elem., 30, 645-645 (1986)
M. Feigel
Journal of the American Chemical Society, 108, 181-181 (1986)
H. Wissmann et al.
Angewandte Chemie (International Edition in English), 92, 129-129 (1980)
Propylphosphonic anhydride (T3P?): an efficient reagent for the one-pot synthesis of 1, 2, 4-oxadiazoles, 1, 3, 4-oxadiazoles, and 1, 3, 4-thiadiazoles.
Augustine JK, et al.
Tetrahedron, 65(48), 9989-9996 (2009)

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