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100-97-0 molecular structure
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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 and InChIs

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

Cite this record

CBID:75349 http://www.chembase.cn/molecule-75349.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1,3,5,7-tetraazatricyclo[3.3.1.1^{3,7}]decane
1,3,5,7-tetraazatricyclo[3.3.1.13,7]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[3.3.1.13,7 ]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
CAS Number
100-97-0
EC Number
202-905-8
MDL Number
MFCD00006895
Beilstein Number
2018
Merck Index
145966
PubChem SID
24895743
24849593
24895429
24860046
162040267
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

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) -0.14668383  LogD (pH = 7.4) 0.37930003 
Log P 0.39213386  Molar Refractivity 36.9954 cm3
Polarizability 15.701157 Å3 Polar Surface Area 12.96 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
1 M acetic acid: soluble0.5 M, clear, colorless expand Show data source
85.3 g/100 mL in water expand Show data source
H2O: soluble0.1 g/mL, clear expand Show data source
H2O: soluble1 M at 20 °C, clear, colorless expand Show data source
Methanol expand Show data source
Apperance
Off-White Solid expand Show data source
Solid expand Show data source
Melting Point
>280°C (dec.) expand Show data source
280 °C expand Show data source
280 °C (subl.)(lit.) expand Show data source
280°C expand Show data source
280(dec.)°C expand Show data source
280°C subl. expand Show data source
ca 280°C subl. expand Show data source
Boiling Point
280 °C (sublimes) expand Show data source
Flash Point
250 °C (open cup) expand Show data source
250 °C expand Show data source
250°C expand Show data source
250°C(482°F) expand Show data source
482 °F expand Show data source
Auto Ignition Point
410 °C (770 °F) expand Show data source
770 °F expand Show data source
Density
1.33 expand Show data source
1.33 g/cm3 at 20 °C expand Show data source
1.33 g/cm3 (at 20 °C) expand Show data source
Vapor Pressure
.0035 hPa at 20 °C expand Show data source
<0.01 mmHg ( 20 °C) expand Show data source
pH
8.5-9.5 (20 °C, 10%) expand Show data source
8.5-9.5 (25 °C, 1 M in H2O) expand Show data source
Storage Condition
0°C expand Show data source
0°C, Desiccate expand Show data source
Refrigerator expand Show data source
Storage Warning
Highly Flammable/Irritant/Hygroscopic expand Show data source
Hygroscopic expand Show data source
RTECS
MN4725000 expand Show data source
European Hazard Symbols
Flammable Flammable (F) expand Show data source
Irritant Irritant (Xi) expand Show data source
Harmful Harmful (Xn) expand Show data source
UN Number
1328 expand Show data source
UN1328 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
Hazard Class
4.1 expand Show data source
Packing Group
3 expand Show data source
III expand Show data source
Australian Hazchem
1Z expand Show data source
Risk Statements
11-43 expand Show data source
R:11-42/43 expand Show data source
Safety Statements
2-24-37 expand Show data source
24-37 expand Show data source
S:16-22-24-37 expand Show data source
EU Classification
F1 expand Show data source
EU Hazard Identification Number
4.1B expand Show data source
Emergency Response Guidebook(ERG) Number
133 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS02 expand Show data source
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
Main Hazard
Highly flammable, harmful expand Show data source
GHS Hazard statements
H228-H302-H317 expand Show data source
H228-H317 expand Show data source
GHS Precautionary statements
P210-P241-P261-P302+P352-P321-P501A expand Show data source
P210-P280 expand Show data source
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 expand Show data source
RID/ADR
UN 1328 4.1/PG 3 expand Show data source
Target
Others expand Show data source
Purity
≥99% expand Show data source
≥98.5% expand Show data source
≥99.0% expand Show data source
≥99.0% (T) expand Show data source
≥99.5% (calc. to the dried substance) expand Show data source
≥99.5% (T) expand Show data source
98% expand Show data source
99% expand Show data source
99+% expand Show data source
99-100.5% (calc. to the dried substance) expand Show data source
Grade
ACS expand Show data source
ACS reagent expand Show data source
JIS special grade expand Show data source
puriss. expand Show data source
puriss. p.a. expand Show data source
REAGENT expand Show data source
ReagentPlus® expand Show data source
SAJ first grade expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Suitability
complies for appearance of solution expand Show data source
Ignition Residue
<0.1% expand Show data source
≤0.01% (as SO4) expand Show data source
≤0.05% expand Show data source
≤0.1% expand Show data source
Impurities
<0.0005% Phosphorus (P) expand Show data source
<0.1% Insoluble matter expand Show data source
≤0.001% heavy metals (as Pb) expand Show data source
≤0.002% heavy metals (as Pb) expand Show data source
≤0.005% free formaldehyde expand Show data source
≤0.01% ammonium (NH4) expand Show data source
acidic and alkalic reac. substances, complies expand Show data source
residual solvents, in accordance expand Show data source
Cation Traces
Al: <0.0005% expand Show data source
Ca: <0.001% expand Show data source
Ca: ≤10 mg/kg expand Show data source
Cd: ≤5 mg/kg expand Show data source
Co: ≤5 mg/kg expand Show data source
Cr: ≤5 mg/kg expand Show data source
Cu: <0.0005% expand Show data source
Cu: ≤5 mg/kg expand Show data source
Fe: <0.0005% expand Show data source
Fe: ≤5 mg/kg expand Show data source
heavy metals (as Pb): ≤0.001% expand Show data source
K: <0.005% expand Show data source
K: ≤50 mg/kg expand Show data source
Mg: <0.0005% expand Show data source
Mg: ≤5 mg/kg expand Show data source
Mn: ≤5 mg/kg expand Show data source
Na: <0.01% expand Show data source
Na: ≤50 mg/kg expand Show data source
NH4+: <0.05% expand Show data source
NH4+: ≤100 mg/kg expand Show data source
Ni: ≤5 mg/kg expand Show data source
Pb: <0.001% expand Show data source
Pb: ≤5 mg/kg expand Show data source
Zn: <0.0005% expand Show data source
Zn: ≤5 mg/kg expand Show data source
Antion Traces
chloride (Cl-): <0.05% expand Show data source
chloride (Cl-): ≤100 mg/kg expand Show data source
chloride (Cl-): ≤20 mg/kg expand Show data source
chloride (Cl-): ≤50 mg/kg expand Show data source
sulfate (SO42-): ≤100 mg/kg expand Show data source
sulfate (SO42-): ≤50 mg/kg expand Show data source
sulfate (SO42-): 0.05% expand Show data source
Loss on Drying
≤2% loss on drying expand Show data source
≤2.0% loss on drying expand Show data source
Quality
meets analytical specification of Ph. Eur., BP expand Show data source
Empirical Formula (Hill Notation)
C6H12N4 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02194050 external link
ACS Reagent Grade
Purity: >99%
For amino acid preparation.
MP Biomedicals - 02151250 external link
Reagent for preparation of amino acids.
Sigma Aldrich - 52710 external link
Other Notes
A versatile reagent for the preparation of primary amines, aromatic formyl groups and N-heterocycles1
Sigma Aldrich - 398160 external link
Packaging
1 kg in poly bottle
250 g in poly bottle
5 g in glass bottle
Sigma Aldrich - H11300 external link
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
Toronto Research Chemicals - H294220 external link
Used in the treatment of urinary track infection.

REFERENCES

REFERENCES

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  • • 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.
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