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

A12571 Hexamethylphosphorous triamide, 97%

Numéro CAS
1608-26-0
Synonymes
HMPT
Tris(dimethylamino)phosphine

Dimensions Prix ($) Quantité Disponibilité
5g 46,14
10g 61,49
25g 131,84
50g 229,69
250g 887,86
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Hexamethylphosphorous triamide, 97%

MDL
MFCD00008301
EINECS
216-534-4

Propriétés chimiques

Formule
[(CH3)2N]3P
Poids formulaire
163.21
Point de fusion
-44°
Point d'ébullition
162-164°
Point d'éclair
37°(98°F)
Densité
0.898
Indice de réfraction
1.4650
Sensibilité
Air Sensitive
Solubilité
Miscible with water.

Applications

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.

Notes

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

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H340-H350-H226

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

Mentions de prudence: P210-P201-P280-P281-P240-P241-P303+P361+P353-P405-P403+P235-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. Use personal protective equipment as required. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. Store locked up. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
906778
Classe de danger
3
Groupe d'emballage
III
Code tarifaire harmonisé
2921.29
TSCA
Yes
RTECS
TH3390000

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