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68957-94-8 - 1-Propylphosphonic acid cyclic anhydride, 50+% soln. in ethyl acetate - 1-Propanephosphonic acid cyclic anhydride - T3P - L11911 - Alfa Aesar

L11911 1-Propylphosphonic acid cyclic anhydride, 50+% soln. in ethyl acetate

CAS Number
68957-94-8
Synonyms
1-Propanephosphonic acid cyclic anhydride
T3P

Size Price ($) Quantity Availability
10g 34.30
50g 102.00
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1-Propylphosphonic acid cyclic anhydride, 50+% soln. in ethyl acetate

MDL
MFCD00006583
EINECS
422-210-5

Chemical Properties

Formula
C9H21O6P3
Formula Weight
318.19
Boiling Point
77°
Flash Point
-3°(26°F)
Density
1.080
Refractive Index
1.4190
Sensitivity
Moisture Sensitive
Solubility
Miscible with dichloromethane, dimethyl formamide, dioxane, terahydrofuran, polar and aprotic organic solvents.

Applications

1-Propylphosphonic acid cyclic anhydride is used in the synthesis of N-acyloxythiazole-2(3H)-thiones. It is also used to promote the synthesis of hydroxamic acids from carboxylic acids. Further, it is employed as an efficient promoter for the Lossen rearrangement to synthesis urea and carbamate derivatives.

Notes

Moisture sensitive. Incompatible withstrong oxidizing agents.

Literature References

T3P is a registered trademark of Clariant Group.

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.

Nand, B.; Khanna, G.; Chaudhary, A.; Lumb, A.; M Khurana, J. 1, 8-Diazabicyclo [5.4. 0] undec-7-ene (DBU): A Versatile Reagent in Organic Synthesis. Curr. Org. Chem. 2015, 19 (9), 790-812

Nagendra, G.; Madhu, C.; Vishwanatha, T. M.; Sureshbabu, V. V. An expedient route for the reduction of carboxylic acids to alcohols employing 1-propanephosphonic acid cyclic anhydride as acid activator. Tetrahedron Lett. 2012, 53 (38), 5059-5063.

GHS Hazard and Precautionary Statements

Hazard Statements: H225-H314-H336

Highly flammable liquid and vapour. Causes severe skin burns and eye damage. May cause drowsiness or dizziness.

Precautionary Statements: P210-P260-P261-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
5079255
Hazard Class
3
Packing Group
II
Harmonized Tariff Code
2934.99
TSCA
No

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