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100-97-0 - Hexamethylenetetramine, 99+% - Hexamine - Methenamine - A17213 - Alfa Aesar

A17213 Hexamethylenetetramine, 99+%

Numéro de CAS
100-97-0
Synonymes
Hexamine
Methenamine

Conditionnement Prix ($) Quantité Disponibilité
250g 18,70
1000g 33,10
5000g 119,00
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Hexamethylenetetramine, 99+%

MDL
MFCD00006895
EINECS
202-905-8

Propriétés chimiques

Formule
C6H12N4
Poids moleculaire
140.19
Point de fusion
ca 280° subl.
Point d'éclair
250°(482°F)
Densité
1.33
Sensibilité
Hygroscopic
Solubilité
Soluble in water, ethanol, chloroform and acetone.

Applications

Hexamethylenetetramine is used as a formylation agent in the synthesis and as a precipitating agent. It is also used in the production of phenolic resins and its moulding compounds, which finds application as binders in fire proof materials, brake and clutch linings. It is involved in the preparation of 5-tert-butyl-2-hydroxy-isophthalaldehyde. It is useful for the treatment of urinary tract infection. Further, it is used in the Duff reaction, Sommelet reaction and in the Delepine reaction.

Notes

Hygroscopic. Incompatible with strong oxidizing agents and strong acids. Avoid conditions like flames, sparks and moisture.

Références bibliographiques

For a review of applications in organic synthesis, see: Synthesis, 161 (1979).

Benzylic halides form quaternary salts with hexamine which undergo oxidation during hydrolysis to give aldehydes (Sommelet reaction): Org. React., 8, 197 (1954); Org. Synth. Coll., 3, 811 (1955); 4, 690, 918 (1963). Benzylamines can also be converted to benzaldehydes; see e.g.: Org. Synth. Coll., 5, 668 (1973).

The reaction can also be carried out to give the primary amine on hydrolysis (Delepine reaction). For conversion of allylic halides to amines, see, e.g.: Org. Synth. Coll., 5, 121 (1973); 9, 666 (1998).

Formylation of arylamines and phenols in the presence of acid to give aldehydes (Duff reaction) generally gives low yields: J. Chem. Soc., 547 (1941); Org. Synth. Coll., 4, 866 (1963). In TFA, formylation of aromatic hydrocarbons occurs in good yield with para-selectivity: J. Org. Chem., 37, 3972 (1972). Careful control of reaction conditions enables 4-substituted phenols in TFA to be converted to either 2-formyl or 2,6-diformyl derivatives: Synthesis, 1029 (1998).

Can be used as a Mannich reagent, e.g. for the ɑ-methylenation of ketones: Synth. Commun., 26, 1775 (1996). For example with reaction scheme, see Propiophenone, A15140.

Opasanont, B.; Van, K. T.; Kuba, A. G.; Choudhury, K. R.; Baxter, J. B. Adherent and Conformal Zn(S,O,OH) Thin Films by Rapid Chemical Bath Deposition with Hexamethylenetetramine Additive. ACS Appl. Mater. Interfaces 2015, 7 (21), 11516-11525.

Durá, G.; Carrión, M. C.; Jalón, F. A.; Manzano, B. R.; Rodri?guez, A. M.; Mereiter, K. Robust 2D Coordination Networks from a Two-Step Assembly Process with Predesigned Silver Cyclic Dimers and Hexamethylenetetramine. Cryst. Growth Des. 2015, 15 (7), 3321-3331.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H228-H317

Flammable solid. May cause an allergic skin reaction.

Mentions de prudence: 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.

Autres références

Merck
14,5966
Beilstein
2018
Classe de danger
4.1
Groupe d'emballage
III
Code tarifaire harmonisé
2933.69
TSCA
Yes
RTECS
MN4725000

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