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33233 Sigma-Aldrich

Hexamethylenetetramine

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

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

  • CAS Number 100-97-0

  • Empirical Formula (Hill Notation) C6H12N4

  • Molecular Weight 140.19

  •  Beilstein/REAXYS Number 2018

  •  EC Number 202-905-8

  •  MDL number MFCD00006895

  •  PubChem Substance ID 57648782

  •  NACRES NA.21

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Properties

Related Categories Analytical Reagents, Analytical Reagents for General Use, Analytical/Chromatography, E-H, Puriss p.a., Puriss p.a. More...
Quality Level   100
grade   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

Description

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.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
UN1328 - class 4.1 - PG 3 - Hexamethylenetetramine
WGK Germany 
WGK 1
RTECS 
MN4725000
Flash Point(F) 
482.0 °F - closed cup
Flash Point(C) 
250 °C - closed cup

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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