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Safety Information

33233

Sigma-Aldrich

Hexamethylenetetramine

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

Synonym(s):

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

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100 EA
CN¥200.07

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About This Item

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

CN¥200.07

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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%)

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General description

Hexamethylenetetramine is a hexamine. It participates in Duff reaction for the synthesis of o-hydroxybenzaldehyde derivatives.[1]

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).[2] It may be used for the synthesis of phenolic aldehydes.[2] It may be used as formylating reagent for the synthesis of various aldehydes.[1]
It has been used for the preparation of ceria nanoparticles, via precipitation method.[3]

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

Regulatory Information

易制爆化学品
危险化学品

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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)
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
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
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