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Propylphosphonic anhydride

CAS No.
68957-94-8
Chemical Name:
Propylphosphonic anhydride
Synonyms
T3P;1-PROPANEPHOSPHONIC ANHYDRIDE;PPACA;1-PROPANEPHOSPHONIC ACID CYCLIC ANHYDRIDE;PROPANE PHOSPHONIC ACID ANHYDRIDE;1-PROPYLPHOSPHONIC ACID CYCLIC ANHYDRIDE;2,4,6-Tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide;PPAA;Propylphosphonic acid anhydride;T3P/Propanephosphonic acid cyclic anhydride
CBNumber:
CB8462554
Molecular Formula:
C9H21O6P3
Molecular Weight:
318.18
MDL Number:
MFCD00006583
MOL File:
68957-94-8.mol
MSDS File:
SDS
Last updated:2023-05-15 10:43:35

Propylphosphonic anhydride Properties

Boiling point 65 °C
Density 1.069 g/mL at 25 °C
vapor pressure 0Pa at 25℃
refractive index n20/D 1.418
Flash point 25 °F
storage temp. Flammables area
solubility Miscible with dioxane, terahydrofuran, dimethyl formamide, polar and aprotic organic solvents.
form Solution
color Clear yellow to brownish
Water Solubility 9.6g/L at 25℃
Sensitive Moisture Sensitive
BRN 5079255
Exposure limits ACGIH: TWA 20 ppm (Skin)
OSHA: TWA 40 ppm(70 mg/m3)
NIOSH: IDLH 137 ppm(25 mg/m3); TWA 20 ppm(34 mg/m3)
Stability Moisture Sensitive
LogP 0 at 25℃
CAS DataBase Reference 68957-94-8(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII I6EGD8839N

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
GHS02,GHS05,GHS07
Signal word  Danger
Hazard statements  H225-H290-H314-H336
Precautionary statements  P210-P233-P234-P280-P303+P361+P353-P305+P351+P338
Hazard Codes  T,C,F
Risk Statements  61-20/21-34-67-66-11
Safety Statements  53-26-36/37/39-45-33-16
RIDADR  UN 2924 3/PG 3
WGK Germany  1
21
TSCA  Yes
HazardClass  8
PackingGroup  II
HS Code  29319019
NFPA 704
3
3 0

Propylphosphonic anhydride Chemical Properties,Uses,Production

Reaction

  1. TP3 is an exceptional reagent for amide/peptide bond formation. The product is very easy to use and combines excellent reaction selectivity, low epimerization, high yields and high product purities.
  2. Conversions of acids and amides to nitriles under mild conditions.
  3. Synthesis of urea and carbamate derivatives.
  4. Formation of thioacids from N-protected amino acids and peptides. 
Reactions of 68957-94-8_1
Reactions of 68957-94-8_2

Chemical Properties

Clear light yellow solution

Uses

Propylphosphonic anhydride may be used in the following studies:

  • As coupling agent for the synthesis of bispyridine-based ligands, which are used as bridging linkers in multinuclear platinum anticancer drugs.
  • Microwave-assissted Fischer indolization of arylhydrazines.
  • As acid activating agent for the direct synthesis of acid azides from carboxylic acids.
  • One-pot synthesis of coumarins.
  • Microwave-mediated synthesis of carbocyclic and heterocyclic fused quinolones.
  • One-pot synthesis of 1,2,4-oxadiazoles, 1,3,4-oxadiazoles, and 1,3,4-thiadiazoles from carboxylic acids.
  • Activation of the carboxyl group for hydroxyamidation and peptide coupling and in the one-pot conversion of carboxylic acids into hydroxamic acids.

Uses

It is employed as an efficient promoter for the Lossen rearrangement to synthesis urea and carbamate derivatives.

General Description

Propylphosphonic anhydride (T3P) is a reactive n-propyl phosphonic acid cyclic anhydride. It is a mild and low toxic coupling agent used in peptide synthesis. T3P also acts as a promoter and water scavenger in the Friedl?nder annulation reaction. It participates in the conversion of carboxylic acids and amides into nitriles, formation of Weinreb amides, ester synthesis, dehydrations, oxidation of alcohols, isonitrile synthesis, synthesis of alkenes from alcohols and C-C coupling reactions. T3P delivers outstanding advantages over traditional reagents, such as broad functional group tolerance, low epimerization, and water-soluble by-products and hence gives high purity and yield of the product.

Flammability and Explosibility

Not classified

1-Propylphosphonic acid cyclic anhydride, 50+% w/w soln. in dichloroMethane 1-Propylphosphonic acid cyclic anhydride, 50 wt.% solution in ethyl acetate 1-Propylphosphonic anhydride solution, 50 wt. % in DMF 1-Propylphosphonic anhydride solution, 50 wt. % in ethyl acetate 2,4,6-tripropyl-1,3,5,2λ5,4λ5,6λ5-trioxatriphosphinane 2,4,6-trioxide 2,4,6-Tripropyl-1,3,5,2,4,6-trioxotriphosphorinane-2,4,6-trioxide (50% solution in Ethyl aceta 1-Propanephosphonic anhydride, in 50% DMF solution≥ 95% 2,4,6-Tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide solution 2,4,6-TRIPROPYL-1,3,5,2,4,6-TRIOXATRIPHOSPHORINE-2,4,6-TRIOXIDE 2,4,6-Tripropyl-1,3,5-trioxa-2,4,6-triphosphacyclohexane 2,4,6-trioxide 2,4,6-Tripropyl-2,4,6-triphospha-1,3,5-trioxacyclohexane 2,4,6-trioxide 1,3,5,2,4,6-trioxatriphosphorinane 1-Propanephosphonic acid cyclic anhydride 50% ethyl acetate n-Propylphosphonic acid anhydride Propylphosphonic acid cyclic anhydride Propylphosphonic Anhydride Solution, 50% in Ethyl Acetate Propylphosphonic anhydride solution technical, ~50% in DMF 1-Propanephosphonic acid cyclic anhydride, 50 wt.% solution in dimethylformamide, AcroSeal 1-Propanephosphonic acid cyclic anhydride, 50 wt.% solution in ethyl acetate, AcroSeal propyl phoshonic anhydride t3p (50% solution in etoac) Propylphosphonic Anhydride Solution, 50wt.% in Ethyl Acetate 1-Propanephosphonic acid cyclic anhydride, 50 wt.% sol. in ethyl acetate 50ML 1-Propanephosphonic Acid Anhydride (Cyclic Trimer) 2,4,6-Tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide 1,3,5,2,4,6-trioxatriphosphorinane,2,4,6-tripropyl-,2,4,6-trioxide propanephosphonicacidanhydride(t3p) propylphosphonicanhydridesolution PROPYLPHOSPHONIC ACID ANHYDRIDE CYCLIC TRIMER PROPYLPHOSPHONIC ANHYDRIDE TRIS-N-PROPAN-PHOSPHONIC ACID ANHYDRIDE Propylphosphonic anhydride solution technical,50% ethyl acetate 1-PROPANEPHOSPHONIC ACID ANHYDRIDE CYCLIC TRIMER 1-PROPYLPHOSPHONIC CYCLIC ANHYDRIDE 1-Propanephosphonic acid cyclic anhydride~(rgT3P~2,4,6-Tripropyl-2,4,6-trioxo-1,3,5,2,4,6-trioxatriphosphorinane 2,4,6-tripropyl-1,3,5-trioxa-2,4,6-triphosphorinane-2,4,6-trioxide Propanephosphonic acid cyclic anhydride (T3P) PROPYLPHOSPHONIC ANHYDRIDE SOLUTION, ~50 % IN DMF PROPANEPHOSPHONIC ANHYDRIDE 50 % IN ETH& 1-Propanephosphonic acid cyclic anhydride, 50 wt.% sol. in ethyl acetate 1-propanephosphonic anhydride solution 1-PROPYLPHOSPHONIC ACID CYCLIC ANHYDRIDE: 50% SOLUTION IN DMF TRIS-N-PROPAN-PHOSPHONIC ACID ANHYDRIDE: (50% IN DMF) Propylphosphonic Acid Anhydride (Cyclic Trimer) (48% in N,N-Dimethylformamide, ca. 1.6mol/L) Propylphosphonic Acid Anhydride (Cyclic Trimer) (50% in Ethyl Acetate, ca. 1.7mol/L) tripropyl-1,3,5,2λ,4λ,6λ-trioxatriphosphinane-2,4,6-trione 1-Propylphosphonic acid cyclic anhydride, 50+% soln. in DMF 2,4,6-tri-n-propyl-2,4,6-trioxo-1,3,5,2,4,6-trioxatriphosphorinane 1-Propanephosphonic anhydride solution, 2,4,6-Tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide solution 1-Propanephosphonic acid cyclic anhydride, 50 WT.% solution in dimethylformamide 1-PROPANEPHOSPHONIC ACID CYCLIC ANHYDRID E, 50 WT. % SOLUTION IN ETHYL ACETATE PROPYLPHOSPHONIC ANHYDRIDE SOLUTION, ~50 % IN ETHYL ACET. 1-Propylphosphonicacidcyclicanhydride,50+%soln.inethylacetate Propylphosphonic anhydride solution (50 wt.% in DMF) 4-[(R)-3-aminopiperidin-1-yl]-2-({6-[(R)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxo-1,2,3,6-tetrahydropyrimidin-1-yl}methyl)benzonitrile, 4-((R)-3-aminopiperidin-1-yl)-2-((6-((R)-3-aminopiperidin-1-yl)-3-methyl-2,4-oxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile Propylphosphonic anhydride 50% in EA Propylphosphonic anhydride 50% in DMF 2,4,6-Tri-n-propyl-2,4,6-trioxo-1,3,5,2,4,6-trioxatriphosphorinane (Propylphosphonic acid anhydride 50% solution in N,N-dimethylformamide) T3P 2,4,6-Tripropyl-2,4,6-trioxo-1,3,5,2,4,6-trioxatriphosphorinane T3P (Propylphosphonic acid anhydride 50% solution in ethyl acetate)