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33233

Sigma-Aldrich

Hexamethylenetetramine

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

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Synonym(s):
1,3,5,7-Tetraazatricyclo[3.3.1.13,7]decane, Hexamine, Methenamine, Urotropine
Empirical Formula (Hill Notation):
C6H12N4
CAS Number:
100-97-0
Molecular Weight:
140.19
Beilstein:
2018
EC Number:
202-905-8
MDL number:
MFCD00006895
PubChem Substance ID:
57648782
NACRES:
NA.21

Agency

USP/NF
reag. Ph. Eur.

Quality Level

100

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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This Item
398160H11300797979
Hexamethylenetetramine puriss. p.a., reag. Ph. Eur., &#8805;99.5% (calc. to the dried substance)

Sigma-Aldrich

33233

Hexamethylenetetramine

Hexamethylenetetramine ACS reagent, &#8805;99.0%

Sigma-Aldrich

398160

Hexamethylenetetramine

Hexamethylenetetramine ReagentPlus&#174;, 99%

Sigma-Aldrich

H11300

Hexamethylenetetramine

Hexamethylenetetramine anhydrous, free-flowing, Redi-Dri&#8482;, ACS reagent, &#8805;99.0%

Sigma-Aldrich

797979

Hexamethylenetetramine

assay

≥99.5% (calc. to the dried substance)

assay

≥99.0%

assay

99%

assay

≥99.0%

form

solid

form

solid

form

-

form

powder

impurities

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

impurities

-

impurities

-

impurities

-

mp

280 °C (subl.) (lit.)

mp

280 °C (subl.) (lit.)

mp

280 °C (subl.) (lit.)

mp

280 °C (subl.) (lit.)

solubility

H2O: soluble

solubility

water: soluble

solubility

H2O: soluble

solubility

H2O: soluble

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
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H228 - H317

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

Certificates of Analysis (COA)

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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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