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33233

Sigma-Aldrich

Hexamethylenetetramine

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

Synonym(s):
Urotropine, Methenamine, Hexamine, 1,3,5,7-Tetraazatricyclo[3.3.1.13,7]decane
Empirical Formula (Hill Notation):
C6H12N4
CAS Number:
Molecular Weight:
140.19
Beilstein:
2018
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

Quality Level

Agency/Method

USP/NF
reag. Ph. Eur.

vapor pressure

<0.01 mmHg ( 20 °C)

grade

puriss. p.a.

assay

≥99.5% (calc. to the dried substance)

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

Signal Word

Warning

Hazard Statements

Hazard Classifications

Flam. Sol. 2 - Skin Sens. 1B

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 1

Flash Point(F)

482.0 °F - closed cup

Flash Point(C)

250 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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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