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Sigma-Aldrich

Esametilentetrammina

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

Sinonimo/i:

1,3,5,7-tetraazatriciclo[3.3.1.13,7]decano, Esamina, Metenamina, Urotropina

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About This Item

Formula empirica (notazione di Hill):
C6H12N4
Numero CAS:
100-97-0
Peso molecolare:
140.19
Beilstein:
2018
Numero CE:
202-905-8
Numero MDL:
MFCD00006895
Codice UNSPSC:
12352100
ID PubChem:
57648782
NACRES:
NA.21

agenzia

USP/NF
reag. Ph. Eur.

Tensione di vapore

<0.01 mmHg ( 20 °C)

Grado

puriss. p.a.

Saggio

≥99.5% (calc. to the dried substance)

Forma fisica

solid

Temp. autoaccensione

770 °F

Impurezze

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

Residuo alla calcinazione

≤0.01% (as SO4)

pH

8.5-9.5 (20 °C, 10%)

Punto di fusione

280 °C (subl.) (lit.)

Solubilità

H2O: soluble

Anioni in tracce

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

Stringa SMILE

C1N2CN3CN1CN(C2)C3

InChI

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

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Descrizione generale

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

Applicazioni

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.

Pittogrammi

FlameExclamation mark
GHS02,GHS07

Avvertenze

Warning

Indicazioni di pericolo

H228,H317

Classi di pericolo

Flam. Sol. 2 - Skin Sens. 1B

Codice della classe di stoccaggio

4.1B - Flammable solid hazardous materials

Classe di pericolosità dell'acqua (WGK)

WGK 1

Punto d’infiammabilità (°F)

482.0 °F - closed cup

Punto d’infiammabilità (°C)

250 °C - closed cup

Dispositivi di protezione individuale

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

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Certificati d'analisi (COA)

Lot/Batch Number
STBK8250
STBK2770
STBK1832
STBJ9032
STBJ5915

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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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