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1608-26-0 - Hexamethylphosphorous triamide, 97% - HMPT - Tris(dimethylamino)phosphine - A12571 - Alfa Aesar

A12571 Hexamethylphosphorous triamide, 97%

Codice CAS
1608-26-0
Sinonimi
HMPT
Tris(dimethylamino)phosphine

Dimensioni Prezzo ($) Quantità Disponibilità
5g 45,70
10g 60,90
25g 131,00
50g 228,00
250g 879,00
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Hexamethylphosphorous triamide, 97%

MDL
MFCD00008301
EINECS
216-534-4

Proprietà chimiche

Formula
[(CH3)2N]3P
Peso formula
163.21
Punto di fusione
-44°
Punto di ebollizione
162-164°
Punto di infiammabilità
37°(98°F)
Densità
0.898
Indice di rifrazione
1.4650
Sensibilità
Air Sensitive
Solubilità
Miscible with water.

Applicazioni

Hexamethylphosphorous triamide is used as a reagent in organic synthesis as a phosphorylating agent. It is associated with carbon tetrachloride for the substitution of hydroxy groups with chlorides. It is involved in the preparation of epoxides and arene oxides from aldehydes and aryldialdehdyes respectively. It is used in the preparation of carbonates as well as reduction of ozonides.

Note

Air and moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents.

Letteratura

Reduces aromatic aldehydes to symmetrical epoxides in good yield: J. Am. Chem. Soc., 85, 1884 (1963). Both cis- and trans-isomers are formed. For list of examples, see: Org. Synth. Coll., 5, 358 (1973). Under suitable conditions, reaction of the intermediate with a second aldehyde can lead to mixed deoxybenzoins or diaryl enamines: Synthesis, 225 (1991).

Has also been used for a variety of other reductions including that of ozonolysis intermediates: Helv. Chim. Acta, 50, 2387 (1967), and of primary alkyl nitro compounds to nitriles: Synthesis, 36 (1979). Bromohydrins can be converted to alkenes, by reductive elimination from their triflate esters: J. Am. Chem. Soc., 102, 1433 (1980):

Reacts with BrCCl3 to give dichloromethylenephosphorane Cl2C=PPh3, which undergoes Wittig reaction with aldehydes to give 1,1-dichloroalkenes, giving better results than the CCl4/PPh3 combination: Tetrahedron Lett., 1237, 1239 (1977); Synthesis, 554 (1980). Similarly, with Br2CF2, the CF2 group can be transferred to both aldehydes and ketones: J. Fluorine Chem., 1, 123 (1971); Synth. Commun., 3, 197 (1973).

Ioannou, P. V.; Tsivgoulis, G. M. The reduction of p-arsanilic acid (p-aminophenylarsonic acid) to its arsonous acid or arsine oxide: A case study. Main Group Chem. 2015, 14 (3), 237-253.

Bhat, C.; Kumar, A. Synthesis of Allokainic Acid: A Review. Asian J. Org. Chem. 2015, 4 (2), 102-115.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H226-H340-H350

Flammable liquid and vapour. May cause genetic defects. May cause cancer.

Dichiarazioni precauzionali: P210-P201-P280-P303+P361+P353-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Obtain special instructions before use. 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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
906778
Classe di rischio
3
Gruppo di imballaggio
III
Codice tariffe armonizzato
2921.29
TSCA
Yes
RTECS
TH3390000

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