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431303
Propylphosphonic anhydride solution
≥50 wt. % in ethyl acetate
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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100 MG
CN¥2,281.89
1 G
CN¥3,229.83
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100 MG
CN¥2,281.89
1 G
CN¥3,229.83
About This Item
Empirical Formula (Hill Notation):
C9H21O6P3
CAS Number:
Molecular Weight:
318.18
Beilstein:
5079255
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
form
liquid
Quality Level
concentration
≥50 wt. % in ethyl acetate
refractive index
n20/D 1.418
bp
65 °C
density
1.069 g/mL at 25 °C
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 (T3P) is a reactive n-propyl phosphonic acid cyclic anhydride.[1] It is a mild and low toxic coupling agent used in peptide synthesis.[2] T3P also acts as a promoter and water scavenger in the Friedländer annulation reaction.[3] 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.[1] 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.[4][1]
Application
Propylphosphonic anhydride (T3P) can be used:
- As an acid-amine coupling reagent for the synthesis of 3-(trifluoromethyl)-1H-pyrazole-5-carboxamides which are potent activators of pyruvate kinase M2 (PKM2).[5]
- In the synthesis of substituted benzofurans as potent DNA gyraseB inhibitors of Mycobacterium tuberculosis.[6]
- As a catalyst in the synthesis of benzothiazoles, benzoxazoles, and benzimidazoles under microwave irradiation.[7]
- As a catalyst in the conversion of ketoximes to amides and aldoximes to nitriles via Beckmann rearrangement.[8]
- As a reagent in the one-pot conversion of aromatic, heteroaromatic, and aliphatic aldehydes to nitriles.[9]
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.[10]
- Microwave-assissted Fischer indolization of arylhydrazines.[11]
- As acid activating agent for the direct synthesis of acid azides from carboxylic acids.[12]
- One-pot synthesis of coumarins.[2]
- Microwave-mediated synthesis of carbocyclic and heterocyclic fused quinolones.[3]
- One-pot synthesis of 1,2,4-oxadiazoles, 1,3,4-oxadiazoles, and 1,3,4-thiadiazoles from carboxylic acids.[1]
- Activation of the carboxyl group for hydroxyamidation and peptide coupling and in the one-pot conversion of carboxylic acids into hydroxamic acids.[13][14]
Legal Information
T3P is a registered trademark of Archimica GmbH
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Product No.
Description
Pricing
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Dam. 1 - Flam. Liq. 2 - Met. Corr. 1 - Skin Corr. 1B - Skin Sens. 1 - STOT SE 3
Target Organs
Central nervous system
Storage Class Code
3 - Flammable liquids
WGK
WGK 1
Flash Point(F)
24.8 °F - closed cup
Flash Point(C)
-4 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
监管及禁止进口产品
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A microwave-assisted, propylphosphonic anhydride (T3P?) mediated one-pot Fischer indole synthesis.
Desroses M, et al.
Tetrahedron Letters, 52(34), 4417-4420 (2011)
T3P: A convenient and useful reagent in organic synthesis
Garcia Ariel LL, et al.
Synlett, 2007(08), 1328-1329 (2007)
An efficient catalytic method for the Beckmann rearrangement of ketoximes to amides and aldoximes to nitriles mediated by propylphosphonic anhydride (T3P)
Augustine JK, et al.
Tetrahedron Letters, 52(10), 1074-1077 (2011)
Glauder, J.
Spec. Chem., 24(3), 30-30 (2004)
Design, synthesis, biological evaluation of substituted benzofurans as DNA gyraseB inhibitors of Mycobacterium tuberculosis
Renuka J, et al.
Bioorganic & Medicinal Chemistry, 22(17), 4924-4934 (2014)
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