Methenamine

Base Information Edit

Chemical Name:Methenamine
CAS No.:100-97-0
Deprecated CAS:11103-67-6,15978-33-3,56549-34-9,74734-16-0,91773-48-7,1556839-80-5,187285-07-0,56549-34-9,74734-16-0,91773-48-7
Molecular Formula:C6H12N4
Molecular Weight:140.188
Hs Code.:2933 69 40
European Community (EC) Number:202-905-8,246-528-7
ICSC Number:1228
NSC Number:757101,26346
UN Number:1328
UNII:J50OIX95QV
DSSTox Substance ID:DTXSID6020692
Nikkaji Number:J1.072.370A,J39.765B
Wikipedia:Hexamethylenetetramine
Wikidata:Q71969
NCI Thesaurus Code:C61841
RXCUI:6832
Metabolomics Workbench ID:43929
ChEMBL ID:CHEMBL1201270
Mol file:100-97-0.mol

Synonyms:Aminoform;Hexamethylenetetramine;Hexamine;Hexamine Silver;Methenamine;Methenamine Silver;Methenamine, Silver;Silver Methenamine;Silver, Hexamine;Silver, Methenamine;Urotropin

This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of Methenamine Edit

Chemical Property:

Appearance/Colour:white crystalline powder
Vapor Pressure:<0.01 mm Hg ( 20 °C)
Melting Point:280 °C (subl.)(lit.)
Refractive Index:1.4260 (estimate)
Boiling Point:252.704 °C at 760 mmHg
PKA:5.1(at 25℃)
Flash Point:103.945 °C
PSA：12.96000
Density:1.428 g/cm³
LogP:-1.26820
Storage Temp.:Store at RT.
Sensitive.:Hygroscopic
Solubility.:H2O: 1 M at 20 °C, clear, colorless
Water Solubility.:895 g/L (20 ºC)
XLogP3:0.3
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:0
Exact Mass:140.106196400
Heavy Atom Count:10
Complexity:84.8
Transport DOT Label:Flammable Solid

Purity/Quality:

Safty Information:

Pictogram(s): F,Xn
Hazard Codes:F,Xn,Xi
Statements: 11-42/43-43
Safety Statements: 16-22-24-37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

Chemical Classes:Nitrogen Compounds -> Amines, Aliphatic
Drug Classes:Antiinfective Agents
Canonical SMILES:C1N2CN3CN1CN(C2)C3
Recent ClinicalTrials:A Multidisciplinary, Multimodal Bundled Care Approach to Chronic Pelvic Pain
Inhalation Risk:Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.
Effects of Short Term Exposure:The substance is mildly irritating to the eyes and skin.
Effects of Long Term Exposure:Repeated or prolonged contact may cause skin sensitization. Repeated or prolonged inhalation may cause asthma.
Uses It can be used as the curing agent for resins and plastics, the vulcanization accelerator of rubber (accelerator H) and textiles shrink-proof agent. It can also be used for making antibacterial drug, explosives and so on. As medicine, after oral administration, it can be decomposed when coming across acidic urine to generate formaldehyde and exerts its antibacterial effect used for treating mild urinary tract infection; it can be externally used for treating ringworm, antiperspirants, and treatment of underarm odor. Its being mixed with caustic soda and sodium phenol can be used as the phosgene absorber of gas masks. It can be used as a kind of anti-microbial agents. It can be used as anti-shrinking textile finishing agent, bleaching agents of sodium chlorite and the buffer of waterproofing agents CR. Hexamethylenetetramine is mainly used as the curing agent of plastic and resin, the catalyst and foaming agent of aminoplast, rubber vulcanization accelerator (accelerator H), and the shrink-proof agents of textiles. Hexamethylenetetramine is the raw material for organic synthesis and can be used for the production of chloramphenicol in the pharmaceutical industry. Hexamethylenetetramine can be used as the disinfectant of urinary system with itself having no antibacterial effect and being effective in treating gram-negative bacteria. Its 20% solution can be used for the treatment of underarm odor, sweaty feet, tinea and so on. Its being mixed with caustic soda and sodium phenol can be used as the phosgene absorber of gas masks. It can also be used for the manufacture of pesticides. Hexamethylenetetramine can react with fuming nitric acid to obtain highly explosive cyclonite, briefly referred as RDX. Hexamethylenetetramine can be used as the reagent and chromatography reagents for determination of bismuth, indium, manganese, cobalt, thorium, platinum, producing magnesium, lithium, copper, uranium, beryllium, tellurium, bromide, and iodide. In the liver function tests, it can be used for formulating thymol turbidity, test and measurement of object such as bismuth, iron, manganese, cobalt, thorium, platinum and magnesium as well as the determination and identification of lithium, iron cyanide, iron bromide and iodide. It can also be used for the determination of copper, uranium, beryllium, tellurium etc. Moreover, it can be used as gas chromatography fixed solution (maximum usage temperature of 180 ℃ with the solvent being chloroform). Used in the treatment of urinary track infection. antibacterial, tuberculostatic Hexamethylenetetramine is a versatile reagent in organic synthesis. It is used in the Duff reaction, the Sommelet reaction, and in the Delepine reaction.
Production method It can be made from the condensation reaction of formaldehyde and ammonia. Place the formaldehyde solution in a reactor, put through the ammonia with condensation reaction being carried out in alkaline solution and the reaction temperature being maintained at 50-70 ℃; the material liquid was cooled and fed into the film vacuum evaporator and subject to evaporation at 60-80 ℃ to make its concentration be increased from 24% to 38%-42%. Then the reaction mixture was filtered and subjected to vacuum evaporation and crystallization, filtration drying to derive the hexamethylenetetramine product. Put the formaldehyde (37% aqueous solution) and excess amount of ammonia for 3 h at 38 ℃. After completion of reaction, the reaction mixture was further subject to clarification, filtration, membrane evaporation (pressure 9.806~9.866 kPa) for twice with concentrated liquid subjecting cooling and crystallization, filtration, and drying at 150 ℃ to obtain the products. It is obtained through the reaction between formaldehyde and the calculated amount of ammonia.
Description Hexamethylenetetramine is a hardener in epoxy resins of the bisphenol A type and can also be used as an anticorrosive agent. It is a sensitizing agent in ceramics workers.
Clinical Use A venerable drug used for the disinfection of acidic urine, methenamine is a low-molecular-weight polymer of ammonia and formaldehyde that reverts to its components under mildly acidic conditions. Formaldehyde is the active antimicrobial component. Methenamine is used for recurrent urinary tract infections. The drug is available in various dosage forms as well as various salts, including the hippurate and mandelate.

Technology Process of Methenamine

There total 63 articles about Methenamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

: 121-82-4,82030-42-0
Hexahydro-1,3,5-trinitro-1,3,5-triazine

: 100-97-0
hexamethylenetetramine

Guidance literature:: With borohydride exchange resin; nickel diacetate; In methanol; for 3h;
DOI:10.1039/b207885f

Reference yield: 98.0%

: C₁₇H₃₀B₂O₂

: 100-97-0
hexamethylenetetramine

Guidance literature:: With ammonium hydroxide; Fe(H)₂(1,2-bis(dimethylphosphino)ethane)₂; In tetrahydrofuran; at 20 - 60 ℃; for 36h; Reagent/catalyst; Schlenk technique; Glovebox; Inert atmosphere;
DOI:10.1021/jacs.5b06077