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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 Registry Number 2018

  •  EC Number 202-905-8

  •  MDL number MFCD00006895

  •  PubChem Substance ID 24860046

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

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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

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

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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 B, Bhuta T, Craig J, et al. Cochrane Database Syst. Rev. (1), CD003265, (2002)

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

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

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

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

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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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