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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:
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

density

1.090  g/cm3

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

Signal Word

Danger

Hazard Statements

H290,H314,H317,H360D

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 2

Flash Point(F)

143.6 °F

Flash Point(C)

62 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

EU REACH SVHC Candidate List

CAS No.

EU REACH Annex XVII (Restriction List)

CAS No.

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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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