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Merck

33233

Sigma-Aldrich

Hexamethylenetetramine

puriss. p.a., reag. Ph. Eur., ≥99.5% (calc. to the dried substance)

Sinónimos:

1,3,5,7-Tetraazatricyclo[3.3.1.13,7]decane, Hexamine, Methenamine, Urotropine

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About This Item

Fórmula empírica (notación de Hill):
C6H12N4
Número de CAS:
Peso molecular:
140.19
Beilstein/REAXYS Number:
2018
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.21

agency

USP/NF
reag. Ph. Eur.

vapor pressure

<0.01 mmHg ( 20 °C)

grade

puriss. p.a.

assay

≥99.5% (calc. to the dried substance)

form

solid

autoignition temp.

770 °F

impurities

≤0.001% heavy metals (as Pb)
≤0.01% ammonium (NH4)

ign. residue

≤0.01% (as SO4)

pH

8.5-9.5 (20 °C, 10%)

mp

280 °C (subl.) (lit.)

solubility

H2O: soluble

anion traces

chloride (Cl-): ≤20 mg/kg
sulfate (SO42-): ≤50 mg/kg

SMILES string

C1N2CN3CN1CN(C2)C3

InChI

1S/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H2

InChI key

VKYKSIONXSXAKP-UHFFFAOYSA-N

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General description

Hexamethylenetetramine is a hexamine. It participates in Duff reaction for the synthesis of o-hydroxybenzaldehyde derivatives.

Application

Hexamethylenetetramine may be used as reagent in the synthesis of 3 and 5-aldehydo salicylic acid, and 2-hydroxy naphthaldehyde, via reaction with salicylic acid and β-naphthol respectively, followed by the treatment with HCl (hydrolysis). It may be used for the synthesis of phenolic aldehydes. It may be used as formylating reagent for the synthesis of various aldehydes.
It has been used for the preparation of ceria nanoparticles, via precipitation method.

pictograms

FlameExclamation mark

signalword

Warning

hcodes

Hazard Classifications

Flam. Sol. 2 - Skin Sens. 1B

Storage Class

4.1B - Flammable solid hazardous materials

wgk_germany

WGK 1

flash_point_f

482.0 °F - closed cup

flash_point_c

250 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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96. A new general method for the preparation of o-hydroxyaldehydes from phenols and hexamethylenetetramine.
Duff JC.
Journal of the Chemical Society, 547-550 (1941)
Formylation of aromatic compounds with hexamethylenetetramine and trifluoroacetic acid.
Smith WE.
The Journal of Organic Chemistry, 37(24), 3972-3973 (1972)
Degradation mitigation in polymer electrolyte membranes using cerium oxide as a regenerative free-radical scavenger.
Trogadas P, et al.
Electrochemical and Solid-State Letters, 11(7), B113-B116 (2008)
Vincent Consonni et al.
ACS nano, 8(5), 4761-4770 (2014-04-12)
Controlling the polarity of ZnO nanowires in addition to the uniformity of their structural morphology in terms of position, vertical alignment, length, diameter, and period is still a technological and fundamental challenge for real-world device integration. In order to tackle
Hong Yu et al.
Nanoscale, 6(18), 10556-10561 (2014-08-15)
Ternary metal oxides have been receiving wide attention in electrochemical energy storage due to their rich redox reactions and tuneable conductivity. We present a simple solution-based method to prepare a 3D interconnected porous network of ternary metal oxide (CoMoO₄ and

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