CAS 100-97-0|Hexamine|HMTA|methenamine|Hexamethylenetetramine|Methenamine|1,3,5,7-Tetraazatricyclo[3.3.1~13,7~]decane|1,3,5,7-tetraazatricyclo[3.3.1.1^{3,7}]decane|1,3,5,7-Tetraazatricyclo[3.3.1.13,...

General Information

Structure

Molecular Formula

C₆H₁₂N₄

Molecular Mass

140.18628

Exact Mass

140.1061964

Charge

InChI

InChI=1S/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H2

InChIKey

VKYKSIONXSXAKP-UHFFFAOYSA-N

Canonic Smiles

C1N2CN3CN1CN(C2)C3

Isomeric Smiles

N12CN3CN(C1)CN(C3)C2

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

Polarizability

15.701157

Polar Surface Area

12.96

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC Traditional name

methenamine formin

Synonyms

HexamineHMTAMethenamine1,3,5,7-Tetraazatricyclo[3.3.1~13,7~]decaneHexamethylenetetramine1,3,5,7-Tetraazatricyclo[3.3.1.13,7 ]decaneUrotropineMethenamine (Mandelamine)HEXAMETHYLENE TETRAMINE1,3,5,7-tetraazaadamantane, Formin, Aminoform乌洛托品1,3,5,7-Tetraazatricyclo[3.3.1.13,7]decane六胺Hexamethylenetetramine1,3,5,7-四氮杂三环[3.3.1.13,7]癸烷环六亚甲基四胺六亚甲基四胺1,3,5,7-TetraazaadamantaneHEXAMETHYLENETETRAMINE ACS REAGENT GRADE1,3,5,7-Tetraazatricyclo[3.3.1.1³,7 ]decaneHexamethylenetetramine, ACS六亚甲基四胺六亚甲基四胺, ACSHexamethylenamineXametrinVulkacit H 30DuirexolHexa BHexasanUritoneHMTFormamineHerax UTSSanceler HT-POUratrinePreparation AFNSC 26346UraminHeterinHAHeksa KAmmoformSanceler HTMethenamideSanceler HHexaformVulkacit HEkagom HMethenaminAntihydralAminoformNocceler HCystogenUrotropinS 4Hexa-Flo-PulverThixon 715BNocceler H-POAceto HMT1,3,5,7-TetraazatricyclodecaneHexaForminNSC 403347Urodeine

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

Names and Identifiers

Registration numbers

PubChem SID

2486472324895743248495931620402672486004624895429

Beilstein Number

MDL Number

CAS Number

EC Number

Unique Ingredient Identifier

J50OIX95QV

Wikipedia Title

Hexamethylenetetramine

PubChem CID

MeSH Name

CHEMBL

Merck Index

ATC CODE

Chemspider ID

CHEBI ID

KEGG ID

Registration numbers

Properties

Safety Information

Highly Flammable/Irritant/Hygroscopic

Hygroscopic

S:16-22-24-37

24-37

Pharmacology Properties

Others

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

MP Biomedicals

02151250

Reagent for preparation of amino acids.

02194050

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

Wikipedia

Hexamethylenetetramine

Sigma Aldrich

52710

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

398160

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

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

TRC

H294220

Used in the treatment of urinary track infection.

Molecule Details

References

PubChem Literature

From Data Sources

• Day, G.M., et al.: J. Physical Chem., 107, 10919 (2003)

• 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).

• For a review of applications in organic synthesis, see: Synthesis, 161 (1979).

• 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.

• 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).

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

methenamine formin

Synonyms

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

Registration numbers

PubChem SID

2486472324895743248495931620402672486004624895429

Beilstein Number

MDL Number

CAS Number

EC Number

Unique Ingredient Identifier

J50OIX95QV

Wikipedia Title

Hexamethylenetetramine

PubChem CID

MeSH Name

CHEMBL

Merck Index

ATC CODE

Chemspider ID

CHEBI ID

KEGG ID

Molecule Details

Reagent for preparation of amino acids.

02194050

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

Wikipedia

Hexamethylenetetramine

Sigma Aldrich

52710

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

398160

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

H11300

TRC

H294220

Used in the treatment of urinary track infection.

Bioactivity

PubChem BioAssay

Properties

Safety Information

Highly Flammable/Irritant/Hygroscopic

Hygroscopic

S:16-22-24-37

24-37

Pharmacology Properties

Others

References

PubChem Literature

From Data Sources

• Day, G.M., et al.: J. Physical Chem., 107, 10919 (2003)

• For a review of applications in organic synthesis, see: Synthesis, 161 (1979).

• 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.

Molecule

ID:75349