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

A12571 Hexamethylphosphorous triamide, 97%

CAS-Nummer
1608-26-0
Synonyme
HMPT
Tris(dimethylamino)phosphine

Größe Preis ($) Menge Verfügbarkeit
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

Chemische Eigenschaften

Formel
[(CH3)2N]3P
Molmasse
163.21
Schmelzpunkt
-44°
Siedepunkt
162-164°
Flammpunkt
37°(98°F)
Dichte
0.898
Brechungsindex
1.4650
Sensitivität
Air Sensitive
Löslichkeit
Miscible with water.

Anwendungen

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.

Bemerkungen

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

Literaturverweise

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.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H226-H340-H350

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

Sicherheitshinweise: P260-P201-P280a-P304+P340-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Obtain special instructions before use. Wear protective gloves and eye/face protection. 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.

Weitere Referenzen

Beilstein
906778
Gefahrenklasse
3
Verpackungsgruppe
III
Harmonized Tariff Code
2921.29
TSCA
Yes
RTECS
TH3390000

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