1,3,5,7-tetraazatricyclo[3.3.1.1^{3,7}]decane

• ChemBase ID: 75349
• Molecular Formular: C6H12N4
• Molecular Mass: 140.18628
• Monoisotopic Mass: 140.1061964
• SMILES: N12CN3CN(C1)CN(C3)C2
• Canonical SMILES: C1N2CN3CN1CN(C2)C3
• InChI: InChI=1S/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H2
• InChIKey: VKYKSIONXSXAKP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3,5,7-tetraazatricyclo[3.3.1.1^{3,7}]decane; 1,3,5,7-tetraazatricyclo[3.3.1.1^3,^7]decane
• IUPAC Traditional name: methenamine; formin
• Synonyms: Hexamine; Methenamine; HMTA; 1,3,5,7-Tetraazatricyclo[3.3.1~13,7~]decane; Hexamethylenetetramine; HEXAMETHYLENE TETRAMINE; 1,3,5,7-Tetraazatricyclo[3.3.1.13,7]decane; Hexamethylenetetramine, ACS; 1,3,5,7-Tetraazaadamantane; 1,3,5,7-Tetraazatricyclodecane; Aceto HMT; Aminoform; Ammoform; Antihydral; Cystogen; Duirexol; Ekagom H; Formamine; Formin; HA; HMT; Heksa K; Herax UTS; Heterin; Hexa; Hexa B; Hexa-Flo-Pulver; Hexaform; Hexamethylenamine; Hexasan; Methenamide; Methenamin; NSC 26346; NSC 403347; Nocceler H; Nocceler H-PO; Preparation AF; S 4; Sanceler H; Sanceler HT; Sanceler HT-PO; Thixon 715B; Uramin; Uratrine; Uritone; Urodeine; Urotropin; Vulkacit H; Vulkacit H 30; Xametrin; 1,3,5,7-Tetraazatricyclo[3.3.1.13,7 ]decane; Urotropine; 1,3,5,7-Tetraazatricyclo[3.3.1.1^3,7 ]decane; HEXAMETHYLENETETRAMINE ACS REAGENT GRADE; Hexamethylenetetramine; 1,3,5,7-tetraazaadamantane, Formin, Aminoform; Methenamine (Mandelamine); 六亚甲基四胺; 六亚甲基四胺, ACS; 1,3,5,7-四氮杂三环[3.3.1.13,7]癸烷; 六亚甲基四胺; 六胺; 环六亚甲基四胺; 乌洛托品

Database IDs

• CAS Number: 100-97-0
• EC Number: 202-905-8
• MDL Number: MFCD00006895
• Beilstein Number: 2018
• Merck Index: 145966
• PubChem SID: 24860046; 24895429; 162040267; 24895743; 24849593; 24864723
• PubChem CID: 4101
• CHEBI ID: 6824
• ATC CODE: J01XX05
• CHEMBL: 1201270
• Chemspider ID: 3959
• KEGG ID: D00393
• MeSH Name: Methenamine
• Unique Ingredient Identifier: J50OIX95QV
• Wikipedia Title: Hexamethylenetetramine

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -0.14668383
• LogD (pH = 7.4): 0.37930003
• Log P: 0.39213386
• Molar Refractivity: 36.9954 cm^3
• Polarizability: 15.701157 Å^3
• Polar Surface Area: 12.96 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 1 M acetic acid: soluble0.5 M, clear, colorless; 85.3 g/100 mL in water; H2O: soluble0.1 g/mL, clear; H2O: soluble1 M at 20 °C, clear, colorless; Methanol
• Apperance: Off-White Solid; Solid
• Melting Point: >280°C (dec.); 280 °C; 280 °C (subl.)(lit.); 280°C; 280(dec.)°C; 280°C subl.; ca 280°C subl.
• Boiling Point: 280 °C (sublimes)
• Flash Point: 250 °C (open cup); 250 °C; 250°C; 250°C(482°F); 482 °F
• Auto Ignition Point: 410 °C (770 °F); 770 °F
• Density: 1.33; 1.33 g/cm^3 at 20 °C; 1.33 g/cm3 (at 20 °C)
• Vapor Pressure: .0035 hPa at 20 °C; <0.01 mmHg ( 20 °C)
• pH: 8.5-9.5 (20 °C, 10%); 8.5-9.5 (25 °C, 1 M in H2O)

Safety Information

• Storage Condition: 0°C; 0°C, Desiccate; Refrigerator
• Storage Warning: Highly Flammable/Irritant/Hygroscopic; Hygroscopic
• RTECS: MN4725000
• European Hazard Symbols: Flammable (F); Irritant (Xi); Harmful (Xn)
• UN Number: 1328; UN1328
• German water hazard class: 1
• Hazard Class: 4.1
• Packing Group: 3; III
• Australian Hazchem: 1Z
• Risk Statements: 11-43; R:11-42/43
• Safety Statements: 2-24-37; 24-37; S:16-22-24-37
• EU Classification: F1
• EU Hazard Identification Number: 4.1B
• Emergency Response Guidebook(ERG) Number: 133
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• Main Hazard: Highly flammable, harmful
• GHS Hazard statements: H228-H302-H317; H228-H317
• GHS Precautionary statements: P210-P241-P261-P302+P352-P321-P501A; P210-P280
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1328 4.1/PG 3

Pharmacology Properties

• Target: Others

Product Information

• Purity: ≥99%; ≥98.5%; ≥99.0%; ≥99.0% (T); ≥99.5% (calc. to the dried substance); ≥99.5% (T); 98%; 99%; 99+%; 99-100.5% (calc. to the dried substance)
• Grade: ACS; ACS reagent; JIS special grade; puriss.; puriss. p.a.; REAGENT; ReagentPlus®; SAJ first grade
• Salt Data: Free Base
• Suitability: complies for appearance of solution
• Ignition Residue: <0.1%; ≤0.01% (as SO4); ≤0.05%; ≤0.1%
• Impurities: <0.0005% Phosphorus (P); <0.1% Insoluble matter; ≤0.001% heavy metals (as Pb); ≤0.002% heavy metals (as Pb); ≤0.005% free formaldehyde; ≤0.01% ammonium (NH4); acidic and alkalic reac. substances, complies; residual solvents, in accordance
• Cation Traces: Al: <0.0005%; Ca: <0.001%; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: <0.0005%; Cu: ≤5 mg/kg; Fe: <0.0005%; Fe: ≤5 mg/kg; heavy metals (as Pb): ≤0.001%; K: <0.005%; K: ≤50 mg/kg; Mg: <0.0005%; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: <0.01%; Na: ≤50 mg/kg; NH4+: <0.05%; NH4+: ≤100 mg/kg; Ni: ≤5 mg/kg; Pb: <0.001%; Pb: ≤5 mg/kg; Zn: <0.0005%; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): <0.05%; chloride (Cl-): ≤100 mg/kg; chloride (Cl-): ≤20 mg/kg; chloride (Cl-): ≤50 mg/kg; sulfate (SO42-): ≤100 mg/kg; sulfate (SO42-): ≤50 mg/kg; sulfate (SO42-): 0.05%
• Loss on Drying: ≤2% loss on drying; ≤2.0% loss on drying
• Quality: meets analytical specification of Ph. Eur., BP
• Empirical Formula (Hill Notation): C6H12N4

DETAILS

MP Biomedicals - 02194050

ACS Reagent Grade
Purity: >99%
For amino acid preparation.

MP Biomedicals - 02151250

Reagent for preparation of amino acids.

Sigma Aldrich - H11300

Packaging
1 kg in poly bottle
4 kg packaged in open-head steel drums; 25 g, 500 g, 1 kg packaged in poly bottles
25, 500 g in poly bottle
4 kg in steel drum
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 52710

Other Notes
A versatile reagent for the preparation of primary amines, aromatic formyl groups and N-heterocycles1

Sigma Aldrich - 398160

Packaging
1 kg in poly bottle
250 g in poly bottle
5 g in glass bottle

Toronto Research Chemicals - H294220

Used in the treatment of urinary track infection.

REFERENCES

• Day, G.M., et al.: J. Physical Chem., 107, 10919 (2003)
• For a review of applications in organic synthesis, see: Synthesis, 161 (1979).
• Benzylic halides form quaternary salts with hexamine which undergo oxidation during hydrolysis to give aldehydes (Sommelet reaction): Org. React., 8, 197 (1954); Org. Synth. Coll., 3, 811 (1955); 4, 690, 918 (1963). Benzylamines can also be converted to benzaldehydes; see e.g.: Org. Synth. Coll., 5, 668 (1973).
• The reaction can also be carried out to give the primary amine on hydrolysis (Delepine reaction). For conversion of allylic halides to amines, see, e.g.: Org. Synth. Coll., 5, 121 (1973); 9, 666 (1998).
• Formylation of arylamines and phenols in the presence of acid to give aldehydes (Duff reaction) generally gives low yields: J. Chem. Soc., 547 (1941); Org. Synth. Coll., 4, 866 (1963). In TFA, formylation of aromatic hydrocarbons occurs in good yield with para-selectivity: J. Org. Chem., 37, 3972 (1972). Careful control of reaction conditions enables 4-substituted phenols in TFA to be converted to either 2-formyl or 2,6-diformyl derivatives: Synthesis, 1029 (1998).
• Can be used as a Mannich reagent, e.g. for the ɑ-methylenation of ketones: Synth. Commun., 26, 1775 (1996). For example with reaction scheme, see Propiophenone, A15140.