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

A12571 Hexamethylphosphorous triamide, 97%

CAS Number
1608-26-0
Synonyms
HMPT
Tris(dimethylamino)phosphine

Size Price ($) Quantity Availability
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

Chemical Properties

Formula
[(CH3)2N]3P
Formula Weight
163.21
Melting point
-44°
Boiling Point
162-164°
Flash Point
37°(98°F)
Density
0.898
Refractive Index
1.4650
Sensitivity
Air Sensitive
Solubility
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.

Literature References

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 Hazard and Precautionary Statements

Hazard Statements: H340-H350-H226

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

Precautionary Statements: 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.

Other References

Beilstein
906778
Hazard Class
3
Packing Group
III
Harmonized Tariff Code
2921.29
TSCA
Yes
RTECS
TH3390000

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