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Merck

33233

Sigma-Aldrich

Hexamethylentetramin

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

Synonym(e):

1,3,5,7-Tetraazatricyclo[3.3.1.13,7]decan, Hexamin, Methenamin, Urotropin

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About This Item

Empirische Formel (Hill-System):
C6H12N4
CAS-Nummer:
Molekulargewicht:
140.19
Beilstein:
2018
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352100
PubChem Substanz-ID:
NACRES:
NA.21

Agentur

USP/NF
reag. Ph. Eur.

Dampfdruck

<0.01 mmHg ( 20 °C)

Qualität

puriss. p.a.

Assay

≥99.5% (calc. to the dried substance)

Form

solid

Selbstzündungstemp.

770 °F

Verunreinigungen

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

Glührückstand

≤0.01% (as SO4)

pH-Wert

8.5-9.5 (20 °C, 10%)

mp (Schmelzpunkt)

280 °C (subl.) (lit.)

Löslichkeit

H2O: soluble

Anionenspuren

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

InChIKey

VKYKSIONXSXAKP-UHFFFAOYSA-N

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Allgemeine Beschreibung

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

Anwendung

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.

Piktogramme

FlameExclamation mark

Signalwort

Warning

H-Sätze

Gefahreneinstufungen

Flam. Sol. 2 - Skin Sens. 1B

Lagerklassenschlüssel

4.1B - Flammable solid hazardous materials

WGK

WGK 1

Flammpunkt (°F)

482.0 °F - closed cup

Flammpunkt (°C)

250 °C - closed cup

Persönliche Schutzausrüstung

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


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Formylation of aromatic compounds with hexamethylenetetramine and trifluoroacetic acid.
Smith WE.
The Journal of Organic Chemistry, 37(24), 3972-3973 (1972)
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)
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)
Jianguo Hu et al.
Talanta, 93, 345-349 (2012-04-10)
A green, one-step method for synthesis of graphene-Au nanoparticles (graphene-AuNPs) was introduced in this article, using an environmentally benign hexamethylenetetramine (HMTA) as reducing and stabilizing agent. HMTA slowly was hydrolyzed to generate aldehyde ammonia to reduce graphene oxides (GO) and
Ann Pontén et al.
Contact dermatitis, 68(1), 50-53 (2012-10-06)
The currently used patch test concentration for formaldehyde is 1.0% (wt/vol) in water. However, clinical experience and previous studies suggest that 1.0% might be insufficient for detecting an optimized number of clinically relevant cases of contact allergy to formaldehyde. To

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