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

A17213 Hexamethylenetetramine, 99+%

CAS Number
100-97-0
Synonyms
Hexamine
Methenamine

Size Price ($) Quantity Availability
250g 16.83
1000g 32.96
5000g 114.91
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Hexamethylenetetramine, 99+%

MDL
MFCD00006895
EINECS
202-905-8

Chemical Properties

Formula
C6H12N4
Formula Weight
140.19
Melting point
ca 280° subl.
Flash Point
250°(482°F)
Density
1.33
Sensitivity
Hygroscopic
Solubility
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.

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H228-H317

Flammable solid. May cause an allergic skin reaction.

Precautionary Statements: P210-P261-P280-P240-P241-P363-P321-P333+P313-P302+P352-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Wash contaminated clothing before reuse. Specific treatment (see label). If skin irritation or rash occurs: Get medical advice/attention. IF ON SKIN: Wash with plenty of soap and water. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,5966
Beilstein
2018
Hazard Class
4.1
Packing Group
III
Harmonized Tariff Code
2933.69
TSCA
Yes
RTECS
MN4725000

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