tripropyl-1,3,5,2λ5,4λ5,6λ5-trioxatriphosphinane-2,4,6-trione

• ChemBase ID: 151814
• Molecular Formular: C9H21O6P3
• Molecular Mass: 318.180723
• Monoisotopic Mass: 318.05509828
• SMILES: CCCP1(=O)OP(=O)(OP(=O)(O1)CCC)CCC
• Canonical SMILES: CCCP1(=O)OP(=O)(CCC)OP(=O)(O1)CCC
• InChI: 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
• InChIKey: PAQZWJGSJMLPMG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tripropyl-1,3,5,2λ^5,4λ^5,6λ^5-trioxatriphosphinane-2,4,6-trione
• IUPAC Traditional name: tripropyl-1,3,5,2λ^5,4λ^5,6λ^5-trioxatriphosphinane-2,4,6-trione
• Synonyms: 1-Propanephosphonic acid cyclic anhydride; T3P; 1-Propylphosphonic acid cyclic anhydride; 2,4,6-Tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide; PPACA; T3P®; 1-Propanephosphonic anhydride solution; 2,4,6-Tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide solution; Propylphosphonic anhydride solution; 1-丙基磷酸环酐; 1-丙基磷酸环酐 溶液; 丙基磷酸三环酸酐 溶液; 1-丙基磷酸酐 溶液

Database IDs

• CAS Number: 68957-94-8
• EC Number: 422-210-5
• MDL Number: MFCD00006583
• Beilstein Number: 5079255
• PubChem SID: 24867005; 162245960; 24887900
• PubChem CID: 111923

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.910051
• LogD (pH = 7.4): 1.910051
• Log P: 1.910051
• Molar Refractivity: 68.3862 cm^3
• Polarizability: 28.764729 Å^3
• Polar Surface Area: 78.9 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 153°C; 65 °C; 77°C
• Flash Point: 143.6 °F; 24.8 °F; -3°C(26°F); -4 °C; 62 °C; 62°C(143°F)
• Density: 1.069 g/mL at 25 °C; 1.080; 1.090
• Refractive Index: 1.4190; 1.4505; n20/D 1.418

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C); Flammable (F); Toxic (T)
• UN Number: 2924; UN2924; UN3265
• German water hazard class: 1
• Hazard Class: 3; 8
• Packing Group: 3; II
• Risk Statements: 11-34-67; 61-20/21-34
• Safety Statements: 16-23-26-36/37/39-45; 16-26-36/37/39-45; 53-26-36/37/39-45; 53-45
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS05; GHS06; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H314-H336; H311-H332-H360-H314-H318-H227; H314-H360D
• GHS Precautionary statements: P201-P280-P305 + P351 + P338-P310; P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P210-P261-P280-P305 + P351 + P338-P310; P210-P303+P361+P353-P305+P351+P338-P361-P405-P501A
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US); Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2924 3/PG 3

Product Information

• Purity: 50+% soln. in DMF; 50+% soln. in ethyl acetate; 95+%
• Concentration: ~50% in DMF; ~50% in ethyl acetate; ≥50 wt. % in ethyl acetate
• Grade: technical
• Empirical Formula (Hill Notation): C9H21O6P3

DETAILS

Sigma Aldrich - 81801

Other Notes
Coupling reagent for peptide synthesis1,2; Preparation of other amides3; Synthesis of esters (depsipeptides)4
Packaging
25, 100 mL in glass bottle
Legal Information
T3P is a registered trademark of Archimica GmbH

Sigma Aldrich - 431303

Application
Activation of the carboxyl group for hydroxyamidation and peptide coupling. Used in peptide synthesis and in the one-pot conversion of carboxylic acids into hydroxamic acids.1,2
Packaging
10, 50, 100, 500 mL in glass bottle
Legal Information
T3P is a registered trademark of Archimica GmbH

Sigma Aldrich - 81799

Legal Information
T3P is a registered trademark of Archimica GmbH

REFERENCES

• Condensation agent in formation of amide and ester linkages. In peptide synthesis, gives high yields, low racemization, and minimization of side reactions without the need for additives, as well as easily removable (water soluble) by-products: Angew. Chem. Int. Ed., 19, 133 (1980). Also reported for formation of a Weinreb amide in high yield from the acid and N,O-dimethylhydroxylamine: Angew. Chem. Int. Ed., 36, 1191 (1997). Activating agent for epoxidation of alkenes, giving cis-stereoselectivity in reactions with allylic alcohols: Tetrahedron Lett., 35, 8125 (1994). For a brief reviews of the reagent, see: Synlett, 1369 (2000); 1328 (2007). For peptide reagents, see Appendix 6.
• T3P is a registered trademark of Clariant Group.
• T3P is a registered trademark of Archimica.
• For use in the synthesis of N-acyloxythiazole-2(3H)-thiones, see: Synlett, 371 (2000).