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398160 Sigma-Aldrich

Hexamethylenetetramine

ACS reagent, ≥99.0%

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

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Properties

Related Categories Building Blocks, Chemical Synthesis, Nitrogen Compounds, Organic Building Blocks, Polyamines More...
grade   ACS reagent
vapor pressure   <0.01 mmHg ( 20 °C)
assay   ≥99.0%
autoignition temp.   770 °F
ign. residue   ≤0.1%
loss   ≤2.0% loss on drying
mp   280 °C (subl.)(lit.)
cation traces   heavy metals (as Pb): ≤0.001%

Description

Packaging

1 kg in poly bottle

250 g in poly bottle

5 g in glass bottle

Price and Availability

Suggested Laboratory Gloves


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Hexamethylenetetramine

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

Hexamethylenetetramine

meets analytical specification of Ph. Eur., BP, 99-100.5% (calc. to the dried substance)

Hexamethylenetetramine

analytical reference material

Hexamethylenetetramine

ReagentPlus®, 99%

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
Risk Statements (Europe) 
Safety Statements (Europe) 
24-37
RIDADR 
UN 1328 4.1 / PGIII
WGK Germany 
1
RTECS 
MN4725000
Flash Point(F) 
482 °F
Flash Point(C) 
250 °C

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

Determination of Water Content in Hexamethylenetetramine Using Karl Fischer Titration

Nitrogen compounds, acid amides and weakly basic amines (heterocyclenes) give no problems. They can be titrated according to the standard procedures. Strongly basic amines alter the pH value and must...
Keywords: Titrations

Peer-Reviewed Papers

References

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Positive patch test reactions in older individuals: retrospective analysis from the North American Contact Dermatitis Group, 1994-2008. Warshaw EM, Raju SI, Fowler JF, et al. J. Am. Acad. Dermatol. 66(2), 229-40, (2012)

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Non-fragrance allergens in specific cosmetic products. Travassos AR, Claes L, Boey L, et al. Contact Dermatitis 65(5), 276-85, (2011)

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Methenamine hippurate for preventing urinary tract infections. Lee BS, Bhuta T, Simpson JM, et al. Cochrane Database Syst. Rev. 10, CD003265, (2012)

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Patch testing with 2.0% (0.60 mg/cm 2) formaldehyde instead of 1.0% (0.30 mg/cm 2) detects significantly more contact allergy. Pontén A, Aalto-Korte K, Agner T, et al. Contact Dermatitis 68(1), 50-3, (2013)

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Occupational contact dermatitis in painters: an analysis of patch test data from the Danish Contact Dermatitis Group. Mose AP, Lundov MD, Zachariae C, et al. Contact Dermatitis 67(5), 293-7, (2012)

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Quaternary ammonium-functionalized silica sorbents for the solid-phase extraction of aromatic amines under normal phase conditions. Vidal L, Robin O, Parshintsev J, et al. J. Chromatogr. A 1285, 7-14, (2013)

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Supramolecular polymorphism of the 1:1 molecular salt (adamantane-1-carboxylate-3,5,7-tricarboxylic acid)·(hexamethylenetetraminium). A "failed" crystal engineering attempt. Lemmerer A, Bernstein J, and Spackman MA Chem. Commun. (Camb.) 48(13), 1883-5, (2012)

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Use of antibiotics in nursing homes--surveillance with different methods. Eriksen HM, Sæther AR, Viktil KK, et al. Tidsskr. Nor. Laegeforen. 133(19), 2052-6, (2013)

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[Compare three methods to detect the Pneumocystis carinii in the bronchoalveolar wash sample of AIDS patients]. Zhang L, Li XW, Shen B, et al. Zhonghua Bing Li Xue Za Zhi 40(7), 482-4, (2011)

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[Hiprex in favour again?]. Norberg B Lakartidningen. 108(22-23), 1255, (2011)

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Methenamine hippurate for preventing urinary tract infections. Lee B, Bhuta T, Craig J, et al. Cochrane Database Syst. Rev. (1), CD003265, (2002)

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Spectrophotometric determination of drugs with iodine. Karuna T, et al. J. Sci. Ind. Res. 65(10), 808, (2006)

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Hexamethylenetetramine: a review. Dreyfors JM, Jones SB, and Sayed Y Am. Ind. Hyg. Assoc. J. 50(11), 579-85, (1989)

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One-step synthesis of graphene-AuNPs by HMTA and the electrocatalytical application for O2 and H2O2. Hu J, Li F, Wang K, et al. Talanta 93, 345-9, (2012)

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Cutaneous delayed-type hypersensitivity in patients with atopic dermatitis: reactivity to topical preservatives. Shaughnessy CN, Malajian D, and Belsito DV J. Am. Acad. Dermatol. 70(1), 102-7, (2014)

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Black tattoo inks are a source of problematic substances such as dibutyl phthalate. Lehner K, Santarelli F, Vasold R, et al. Contact Dermatitis 65(4), 231-8, (2011)

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Improving the Detection of Fungi in Eosinophilic Mucin: Seeing What We Could Not See Before Guo, C., et al. Otolaryngol. Head Neck Surg. 147(5), 943-9, (2012)

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Formaldehyde and hexamethylenetetramine as food additives: chemical interactions and toxicology. Restani P, Restelli AR, and Galli CL Food Addit. Contam. 9(5), 597-605, (1992)

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Prevention of urinary tract infections in nursing homes: lack of evidence-based prescription? Bergman J, Schjøtt J, and Blix HS BMC Geriatr. 11, 69, (2011)

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The methenamine misunderstanding in the therapy of phosgene poisoning. Diller WF Arch. Toxicol. 46(3-4), 199-206, (1980)

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Patch testing with formaldehyde and formaldehyde-releasers: multicentre study in Spain (2005-2009). Latorre N, Borrego L, Fernández-Redondo V, et al. Contact Dermatitis 65(5), 286-92, (2011)

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Towards high-performance, low-cost quartz sensors with high-density, well-separated, vertically aligned ZnO nanowires by low-temperature, seed-less, single-step, double-sided growth. Orsini A, Medaglia PG, Scarpellini D, et al. Nanotechnology 24(35), 355503, (2013)

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Drug therapy reviews: methenamine mandelate and methenamine hippurate. Gleckman R, Alvarez S, Joubert DW, et al. Am. J. Hosp. Pharm. 36(11), 1509-12, (1979)

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Heterogeneous degradation of precipitated hexamine from wastewater by catalytic function of silicotungstic acid in the presence of H2O2 and H2O2/Fe2+. Taghdiri M, Saadatjou N, Zamani N, et al. J. Hazard. Mater. 246-247, 206-12, (2013)

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A robust metal-organic framework constructed from alkoxo-bridged binuclear nodes and hexamethylenetetramine spacers: crystal structure and sorption studies. Ilyes E, Florea M, Madalan AM, et al. Inorg. Chem. 51(15), 7954-6, (2012)

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Attempts to counteract phosgene-induced acute lung injury by instant high-dose aerosol exposure to hexamethylenetetramine, cysteine or glutathione. Pauluhn J and Hai CX Inhal. Toxicol. 23(1), 58-64, (2011)

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The first metal-organic framework containing an unprecedented in situ-generated C-substituted hexamethylenetetramine ligand. Deng ZP, Huo LH, Xu H, et al. Dalton Trans. 40(6), 1224-6, (2011)

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Early multimodality treatment of intracranial abscesses. Pendleton C, Jallo GI, and Quiñones-Hinojosa A World Neurosurg. 78(6), 712-4, (2012)

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Allergic contact dermatitis of the vulva. O'Gorman SM and Torgerson RR Dermatitis 24(2), 64-72, (2013)

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Urinary tract analgesics for the treatment of patients with acute cystitis: where is the clinical evidence? Pergialiotis V, Arnos P, Mavros MN, et al. Expert Rev. Anti. Infect. Ther. 10(8), 875-9, (2012)

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Ultra-sensitive complex as phosphorescence probe for the determination of trace protein. Liu JM, Jiang SL, Cui ML, et al. Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 102, 1-6, (2013)

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Is quaternium-15 a formaldehyde releaser? Correlation between positive patch test reactions to formaldehyde and quaternium-15. Odhav A and Belsito DV Dermatitis 23(1), 39-43, (2012)

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Eradication of Helicobacter pylori. Can methenamine, an antimicrobial designed to be effective at an acidic pH, meet this challenge? Paranjape SG, Turankar AV, and Sontakke SD Med. Hypotheses 80(4), 507, (2013)

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Follow-up of the monitored levels of preservative sensitivity in Europe: overview of the years 2001-2008. Svedman C, Andersen KE, Brandão FM, et al. Contact Dermatitis 67(5), 312-4, (2012)

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Brain abscesses: past and present. de Divitiis O and de Divitiis E World Neurosurg. 78(6), 607-9, (2012)

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What have I learned from my neurosurgical "great-grandfather". van Dellen JR World Neurosurg. 78(6), 605-6, (2012)

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Contact sensitization to quaternium-15 acting as a warning sign for curare allergy. Osdoit S, Guillet MH, and Guillet G Contact Dermatitis 65(2), 120-2, (2011)

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Methenamine hippurate for preventing urinary tract infections. Lee BB, Simpson JM, Craig JC, et al. Cochrane Database Syst. Rev. (4), CD003265, (2007)

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Merck 14,5966

Beil. 26,IV,1680

Fieser 1,427 / Fieser 2,208 / Fieser 4,243 / Fieser 9,234

Aldrich MSDS 1, 1026:B / Corp MSDS 1 (1), 1852:B / FT-IR 1 (1), 378:B / FT-NMR 1 (1), 596:B / IR-Spectra (2), 201:A / IR-Spectra (3), 224:D / NMR-Reference 2 (1), 332:D / RegBook 1 (1), 401:D / Sax 6, 1522 / Sigma FT-IR 1 (1), 666:A / Structure Index 1, 58:A:1 / Vapor Phase 3, 471:D

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