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

A17213 Hexamethylenetetramine, 99+%

Codice CAS
100-97-0
Sinonimi
Hexamine
Methenamine

Dimensioni Prezzo ($) Quantità Disponibilità
250g 18,70
1000g 33,10
5000g 119,00
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Hexamethylenetetramine, 99+%

MDL
MFCD00006895
EINECS
202-905-8

Proprietà chimiche

Formula
C6H12N4
Peso formula
140.19
Punto di fusione
ca 280° subl.
Punto di infiammabilità
250°(482°F)
Densità
1.33
Sensibilità
Hygroscopic
Solubilità
Soluble in water, ethanol, chloroform and acetone.

Applicazioni

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.

Note

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

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H228-H317

Flammable solid. May cause an allergic skin reaction.

Dichiarazioni precauzionali: P210-P261-P280a-P240-P241-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Merck
14,5966
Beilstein
2018
Classe di rischio
4.1
Gruppo di imballaggio
III
Codice tariffe armonizzato
2933.69
TSCA
Yes
RTECS
MN4725000

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