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A12571 Hexamethylphosphorous triamide, 97%

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

Stock No. Size Price ($) Quantity Availability
A12571-06 5g 47.10
A12571-09 10g 64.00
A12571-14 25g 138.00
A12571-18 50g 240.00
A12571-30 250g 924.00
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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
Storage & Sensitivity
Air Sensitive. Store under Nitrogen. May form a Precipitate. Ambient temperatures.
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: H226-H315-H319-H335-H351

Flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. Suspected of causing cancer.

Precautionary Statements: P201-P202-P210-P233-P240-P243-P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P308+P313-P332+P313-P337+P313-P362-P374-P380-P501c

Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Ground/bond container and receiving equipment. Take precautionary measures against static discharge. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or concerned: Get medical advice/attention. If skin irritation occurs: If eye irritation persists: Take off contaminated clothing and wash before reuse. Fight fire with normal precautions from a reasonable distance. Evacuate area. Dispose of contents/ container to an approved waste disposal plant

Other References

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

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