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Merck
CN

33233

Hexamethylenetetramine

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

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C6H12N4
CAS Number:
100-97-0
Molecular Weight:
140.19
NACRES:
NA.21
PubChem Substance ID:
57648782
UNSPSC Code:
12352100
EC Number:
202-905-8
MDL number:
MFCD00006895
Beilstein/REAXYS Number:
2018

Key Documents

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Product Name

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

InChI key

VKYKSIONXSXAKP-UHFFFAOYSA-N

InChI

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

SMILES string

C1N2CN3CN1CN(C2)C3

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

Quality Level

100

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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.

General description

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

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Warning

hcodes

H228,H317

Hazard Classifications

Flam. Sol. 2 - Skin Sens. 1B

Storage Class

4.1B - Flammable solid hazardous materials

wgk

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

Regulatory Information

危险化学品
易制爆化学品
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Certificates of Analysis (COA)

Lot/Batch Number
STBL3762
STBL1711
STBL1156
STBK8250
STBK2770

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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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