Azepane

Azepane is the organic compound with the formula (CH2)6NH. It is a colorless liquid. A cyclic secondary amine, it is a precursor to several drugs and pesticides. It is produced by partial hydrogenolysis of hexamethylene diamine.[2]

Azepane
Skeletal formula of azepane
Ball-and-stick model of the azepane molecule
Names
Preferred IUPAC name
Azepane
Other names
  • Hexahydroazepine
  • Hexamethyleneimine
  • Homopiperidine
  • Perhydroazepine
  • HMI
  • azacycloheptane
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.524
UNII
  • InChI=1S/C6H13N/c1-2-4-6-7-5-3-1/h7H,1-6H2 checkY
    Key: ZSIQJIWKELUFRJ-UHFFFAOYSA-N checkY
  • InChI=1/C6H13N/c1-2-4-6-7-5-3-1/h7H,1-6H2
    Key: ZSIQJIWKELUFRJ-UHFFFAOYAF
  • C1CCCNCC1
Properties
C6H13N
Molar mass 99.177 g·mol−1
Appearance colorless liquid
Density 0.88 g/cm3[1]
Melting point −37 °C (−35 °F; 236 K)
Boiling point 138 °C (280 °F; 411 K)[1] (749 mmHg)
Hazards
Flash point 30 °C (86 °F; 303 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Like many amines, it reacts with carbon dioxide.[3]

Azepane-containing drugs
  1. AK-1 [330461-64-8]
  2. Amicibone
  3. Bazedoxifene
  4. Bacmecillinam (KW 1100)
  5. Brazergoline
  6. BRN 1322519 [4082-37-5][4]
  7. Buzepide (Fenpipramide homolog).
  8. Cetiedil
  9. Gimantan
  10. Glidazamide
  11. Glisoxepide
  12. Glypinamide
  13. Hexacaine
  14. Mecillinam
  15. Molinate
  16. MR-16728 (cetiedil analogue)
  17. Nabazenil
  18. PD-157667
  19. PD-158143
  20. PD-151307
  21. Pincainide
  22. Prozapine
  23. Setastine
  24. Tolazamide
  25. UCL 1608 Fb: [371172-30-4] Oxalate Salt: [371172-31-5]

See also

References
  1. "Hexamethyleneimine".
  2. Karsten Eller; Erhard Henkes; Roland Rossbacher; Hartmut Höke (2005). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001. ISBN 3527306730.
  3. Sanz-Pérez, E. S.; Arencibia, A.; Sanz, R.; Calleja, G. (2016). "New developments on carbon dioxide capture using amine-impregnated silicas". Adsorption. 22 (4): 366–375. doi:10.1007/s10450-015-9740-2. S2CID 100692983.
  4. Barron, D. I.; Hall, G. H.; Natoff, I. L.; Ridley, H. F.; Spickett, R. G. W.; Vallance, D. K. (1965). "Compounds Affecting the Central Nervous System. III. Substituted 1,1-Diaryl-t-aminopropanols and Related Compounds". Journal of Medicinal Chemistry. 8 (6): 836-841. doi:10.1021/jm00330a023.
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