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Sigma-Aldrich

Hexamethylenetetramine

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

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C6H12N4
Número CAS:
100-97-0
Peso molecular:
140.19
Beilstein:
2018
Número CE:
202-905-8
Número MDL:
MFCD00006895
Código UNSPSC:
12352100
ID de substância PubChem:
57648782
NACRES:
NA.21

Agency

USP/NF
reag. Ph. Eur.

pressão de vapor

<0.01 mmHg ( 20 °C)

grau

puriss. p.a.

Ensaio

≥99.5% (calc. to the dried substance)

forma

solid

temperatura de autoignição

770 °F

Impurezas

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

resíduo de ignição

≤0.01% (as SO4)

pH

8.5-9.5 (20 °C, 10%)

pf

280 °C (subl.) (lit.)

solubilidade

H2O: soluble

traços de ânion

chloride (Cl-): ≤20 mg/kg
sulfate (SO42-): ≤50 mg/kg

cadeia de caracteres SMILES

C1N2CN3CN1CN(C2)C3

InChI

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

chave InChI

VKYKSIONXSXAKP-UHFFFAOYSA-N

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Descrição geral

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

Aplicação

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.

Pictogramas

FlameExclamation mark
GHS02,GHS07

Palavra indicadora

Warning

Frases de perigo

H228,H317

Classificações de perigo

Flam. Sol. 2 - Skin Sens. 1B

Código de classe de armazenamento

4.1B - Flammable solid hazardous materials

Classe de risco de água (WGK)

WGK 1

Ponto de fulgor (°F)

482.0 °F - closed cup

Ponto de fulgor (°C)

250 °C - closed cup

Equipamento de proteção individual

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

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Certificados de análise (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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