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A17213 Hexamethylenetetramine, 99+%

CAS Number
100-97-0
Synonyms
Hexamine
Methenamine

Stock No. Size Price ($) Quantity Availability
A17213-30 250g 19.50
A17213-0B 1000g 34.60
A17213-0I 5000g 125.00
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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
Storage & Sensitivity
Hygroscopic. Ambient temperatures.
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-H500

Flammable solid. May cause an allergic skin reaction. May form combustible dust concentrations in air

Precautionary Statements: P210-P240-P241-P261-P272-P280-P302+P352-P333+P313-P363-P370+P378q-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Avoid breathing dust/fume/gas/mist/vapours/spray. Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. If skin irritation or rash occurs: Get medical advice/attention. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant

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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