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| ImageSize1 = 180px
| ImageSize1 = 180px
| ImageFile2 = Cyclohexylamine-3D-balls.png
| ImageFile2 = Cyclohexylamine-3D-balls.png
| IUPACName = Cyclohexanamine
| PIN = Cyclohexanamine
| OtherNames = Aminocyclohexane<br>Aminohexahydrobenzene<br>Hexahydroaniline<br/>Hexahydrobenzenamine
| OtherNames = Aminocyclohexane<br>Aminohexahydrobenzene<br>Hexahydroaniline<br/>Hexahydrobenzenamine
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
Line 31: Line 31:
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 15773
| ChEBI = 15773
| ChEMBL = 1794762
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C00571
| KEGG = C00571
| 3DMet = B00135
}}
}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
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| Odor = strong, fishy, [[amine]] odor
| Odor = strong, fishy, [[amine]] odor
| Density = 0.8647 g/cm<sup>3</sup>
| Density = 0.8647 g/cm<sup>3</sup>
| MeltingPtC = -17.7
| MeltingPtC = −17.7
| MeltingPt_notes =
| MeltingPt_notes =
| BoilingPtC = 134.5
| BoilingPtC = 134.5
| BoilingPt_notes =
| BoilingPt_notes =
| Solubility = Miscible
| Solubility = Miscible
| SolubleOther = very soluble in [[ethanol]], [[oil]] <br> miscible in [[ether]]s, [[acetone]], [[ester]]s, [[alcohol]], [[ketone]]s
| SolubleOther = very soluble in [[ethanol]], [[oil]] <br> miscible in [[ether]]s, [[acetone]], [[ester]]s, [[Alcohol (chemistry)|alcohol]], [[ketone]]s
| pKa = 10.64<ref>H. K. Hall, ''J. Am. Chem. Soc.'' (1957) '''79''' 5441.</ref>
| pKa = 10.64<ref>H. K. Hall, ''J. Am. Chem. Soc.'' (1957) '''79''' 5441.</ref>
| RefractIndex = 1.4565
| RefractIndex = 1.4565
| VaporPressure = 11 mmHg (20° C)<ref name=NIOSH>{{PGCH|0168}}</ref>
| VaporPressure = 11 mmHg (20°C)<ref name=NIOSH>{{PGCH|0168}}</ref>
}}
}}
|Section7={{Chembox Hazards
|Section7={{Chembox Hazards
| EUClass =
| MainHazards =
| MainHazards =
| NFPA-H = 3
| NFPA-H = 3
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| NFPA-R = 0
| NFPA-R = 0
| NFPA-S =
| NFPA-S =
| GHSPictograms = {{GHS02}}{{GHS05}}{{GHS07}}{{GHS08}}
| RPhrases =
| GHSSignalWord = Danger
| SPhrases = {{S36}} {{S37}} {{S39}}
| HPhrases = {{H-phrases|226|302|312|314|361}}
| RSPhrases = {{R21}} {{R23}} {{R25}} {{R36}} {{R37}} {{R38}} {{R41}}
| PPhrases = {{P-phrases|201|202|210|233|240|241|242|243|260|264|270|280|281|301+312|301+330+331|302+352|303+361+353|304+340|305+351+338|308+313|310|312|321|322|330|363|370+378|403+235|405|501}}
| FlashPtC = 28.6
| FlashPtC = 28.6
| AutoignitionPtC = 293
| AutoignitionPtC = 293
| ExploLimits = 1.5%-9.4%<ref name=NIOSH/>
| ExploLimits = 1.5–9.4%<ref name=NIOSH/>
| LD50 = 156 mg/kg (rat, oral)
| LD50 = 156 mg/kg (rat, oral)
| PEL = none<ref name=NIOSH/>
| PEL = none<ref name=NIOSH/>
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}}
}}


'''Cyclohexylamine''' is an [[organic compound]], belonging to the [[aliphatic]] [[amine]] class. It is a colorless liquid, although like many amines, samples are often colored due to contaminants. It has a fishy odor and is miscible with water. Like other amines, it is a [[weak base]], compared to [[strong base]]s such as [[NaOH]], but it is a stronger base than its [[aromatic]] analog, [[aniline]].
'''Cyclohexylamine''' is an [[organic compound]], belonging to the [[aliphatic]] [[amine]] class. It is a colorless liquid, although, like many amines, samples are often colored due to contaminants. It has a fishy odor and is miscible with water. Like other amines, it is a [[weak base]], compared to [[strong base]]s such as [[NaOH]], but it is a stronger base than its [[aromatic]] analog, [[aniline]].


It is a useful intermediate in the production of many other organic compounds.
It is a useful intermediate in the production of many other organic compounds (e.g. [[cyclamate]])
It is a metabolite of [[cyclamate]].


==Preparation==
==Preparation==
Cyclohexylamine is produced by two routes, the main one being hydrogenation of [[aniline]] using cobalt or nickel catalysts:<ref name=Ullmann>Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. {{DOI|10.1002/14356007.a02_001}}</ref>
Cyclohexylamine is produced by two routes, the main one being the complete hydrogenation of [[aniline]] using some cobalt- or nickel-based catalysts:<ref name=Ullmann>{{Ullmann|first1=Karsten|last1=Eller|first2=Erhard|last2=Henkes|first3=Roland|last3=Rossbacher|first4=Hartmut|last4=Höke|title=Amines, Aliphatic|year=2005|doi=10.1002/14356007.a02_001}}</ref>
:C<sub>6</sub>H<sub>5</sub>NH<sub>2</sub> + 3 H<sub>2</sub> → C<sub>6</sub>H<sub>11</sub>NH<sub>2</sub>
[[File:Cyclohexylamine synthesis.png|250px|thumb|center|<center>Cyclohexylamine catalytical synthesis from [[aniline]] hydrogenation upon high pressure and temperature.<center>]]

It is also prepared by [[amine alkylation|alkylation]] of ammonia using [[cyclohexanol]].
It is also prepared by [[amine alkylation|alkylation]] of ammonia using [[cyclohexanol]].


==Applications==
==Applications==
Cyclohexylamine is used as an intermediate in synthesis of other organic compounds. It is the precursor to [[sulfenamide]]-based reagents used as [[accelerator (chemistry)|accelerators]] for [[vulcanization]]. It is a building block for pharmaceuticals (e.g., [[mucolytic]]s, [[analgesic]]s, and [[bronchodilator]]s). The amine itself is an effective [[corrosion inhibitor]]. Some [[sweeteners]] are derived from this amine, notably [[cyclamate]]. The herbicide [[hexazinone]] is derived from cyclohexylamine.<ref name=Ullmann/>
Cyclohexylamine is used as an intermediate in synthesis of other organic compounds. It is the precursor to [[sulfenamide]]-based reagents used as [[accelerator (chemistry)|accelerators]] for [[vulcanization]]. The amine itself is an effective [[corrosion inhibitor]]. It has been used as a flushing aid in the [[printing ink]] industry.<ref name="Apps">

[[Hexylcaine]] is another usage of [[Cy]]NH<sub>2</sub>.

⚫
==Toxicity==
⚫
LD<sub>50</sub> (rat; p.o.) = 0.71 ml/kg<ref>''The Merck Index, 10th Ed.'' (1983) p.392, Rahway: Merck & Co.</ref>

==Safety==
It is flammable, with [[flash point]] at 28.6&nbsp;°C. It is toxic by both ingestion and inhalation; the inhalation itself may be fatal. It readily absorbs through skin, which it irritates. It is corrosive. Cyclohexylamine is listed as an [[List of Extremely Hazardous Substances|extremely hazardous substance]] as defined by Section 302 of the U.S. [[Emergency Planning and Community Right-to-Know Act]]. It has been used as a flushing aid in the [[printing ink]] industry.<ref name="Apps">
{{Cite book
{{Cite book
| last = Apps
| last = Apps
| first = E. A.
| first = E. A.
| authorlink =
| coauthors =
| title = Printing Ink Technology
| title = Printing Ink Technology
| publisher = Leonard Hill <nowiki>[Books]</nowiki> Limited
| publisher = Leonard Hill <nowiki>[Books]</nowiki> Limited
Line 101: Line 91:
| location = London
| location = London
| pages = ix
| pages = ix
| url =https://archive.org/details/printinginktechn00apps
| url =
| url-access = registration
| doi =
}}
| id =
| isbn = }}
</ref>
</ref>
===Drugs List===
It is a building block for pharmaceuticals (e.g., [[mucolytic]]s, [[analgesic]]s, and [[bronchodilator]]s). Most of the drugs in the following list fall into the arena of sulfonamide hypoglycemics though:
#[[Acetohexamide]]
#[[Amesergide]]
#[[Bromhexine]]
#[[Brovanexine]]
#[[CGP-11112]] (not actually made from CyNH2 but CyN containing).
#[[Cilostazol]]
#[[Clorexolone]]
#[[Cyclamate]]
#[[Enpromate]]
#[[Esaprazole]]
#[[Glibenclamide]]
#[[Glicaramide]]
#[[Gliquidone]]
#[[Glipizide]]
#[[Glisindamide]]
#[[Glisolamide]]
#[[Glycyclamide]]
#[[Glyhexamide]]
#[[Hexazinone]]
#[[Hexylcaine]]
#[[Hydroxyhexamide]]
#[[lomustine]]
#[[Metahexamide]]
#[[Timegadine]]
#[[Thiohexamide]]
#[[U-37883A]]

⚫
==Toxicity==
⚫
Cyclohexylamine has a low acute toxicity with LD<sub>50</sub> (rat; p.o.) = 0.71 ml/kg<ref>''The Merck Index, 10th Ed.'' (1983) p.392, Rahway: Merck & Co.</ref> Like other amines, it is corrosive.


In regards to occupational exposures, the [[National Institute for Occupational Safety and Health]] has suggested workers not be exposed to a [[recommended exposure limit]] of over 10 ppm (40&nbsp;mg/m<sup>3</sup>) over an eight-hour workshift.<ref name=NIOSH/>
Cyclohexylamine is listed as an [[List of Extremely Hazardous Substances|extremely hazardous substance]] as defined by Section 302 of the U.S. [[Emergency Planning and Community Right-to-Know Act]]. The [[National Institute for Occupational Safety and Health]] has suggested workers not be exposed to a [[recommended exposure limit]] of over 10 ppm (40&nbsp;mg/m<sup>3</sup>) over an eight-hour workshift.<ref name=NIOSH/>


==References==
==References==
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[[Category:Amines]]
[[Category:Amines]]
[[Category:Cyclohexyl compounds]]

Latest revision as of 08:30, 9 June 2024

Cyclohexylamine[1]
Names
Preferred IUPAC name
Cyclohexanamine
Other names
Aminocyclohexane
Aminohexahydrobenzene
Hexahydroaniline
Hexahydrobenzenamine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.300 Edit this at Wikidata
EC Number
  • 203-629-0
KEGG
RTECS number
  • GX0700000
UNII
  • InChI=1S/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2 checkY
    Key: PAFZNILMFXTMIY-UHFFFAOYSA-N checkY
  • InChI=1/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2
    Key: PAFZNILMFXTMIY-UHFFFAOYAP
  • NC1CCCCC1
Properties
C6H13N
Molar mass 99.17
Appearance clear to yellowish liquid
Odor strong, fishy, amine odor
Density 0.8647 g/cm3
Melting point −17.7 °C (0.1 °F; 255.5 K)
Boiling point 134.5 °C (274.1 °F; 407.6 K)
Miscible
Solubility very soluble in ethanol, oil
miscible in ethers, acetone, esters, alcohol, ketones
Vapor pressure 11 mmHg (20°C)[2]
Acidity (pKa) 10.64[3]
1.4565
Hazards
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazard
Danger
H226, H302, H312, H314, H361
P201, P202, P210, P233, P240, P241, P242, P243, P260, P264, P270, P280, P281, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P322, P330, P363, P370+P378, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
3
0
Flash point 28.6 °C (83.5 °F; 301.8 K)
293 °C (559 °F; 566 K)
Explosive limits 1.5–9.4%[2]
Lethal dose or concentration (LD, LC):
156 mg/kg (rat, oral)
NIOSH (US health exposure limits):
PEL (Permissible)
 none[2]
REL (Recommended)
 TWA 10 ppm (40 mg/m3)[2]
IDLH (Immediate danger)
 N.D.[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Cyclohexylamine is an organic compound, belonging to the aliphatic amine class. It is a colorless liquid, although, like many amines, samples are often colored due to contaminants. It has a fishy odor and is miscible with water. Like other amines, it is a weak base, compared to strong bases such as NaOH, but it is a stronger base than its aromatic analog, aniline.

It is a useful intermediate in the production of many other organic compounds (e.g. cyclamate)

Preparation

[edit]

Cyclohexylamine is produced by two routes, the main one being the complete hydrogenation of aniline using some cobalt- or nickel-based catalysts:[4]

C6H5NH2 + 3 H2 → C6H11NH2

It is also prepared by alkylation of ammonia using cyclohexanol.

Applications

[edit]

Cyclohexylamine is used as an intermediate in synthesis of other organic compounds. It is the precursor to sulfenamide-based reagents used as accelerators for vulcanization. The amine itself is an effective corrosion inhibitor. It has been used as a flushing aid in the printing ink industry.[5]

Drugs List

[edit]

It is a building block for pharmaceuticals (e.g., mucolytics, analgesics, and bronchodilators). Most of the drugs in the following list fall into the arena of sulfonamide hypoglycemics though:

  1. Acetohexamide
  2. Amesergide
  3. Bromhexine
  4. Brovanexine
  5. CGP-11112 (not actually made from CyNH2 but CyN containing).
  6. Cilostazol
  7. Clorexolone
  8. Cyclamate
  9. Enpromate
  10. Esaprazole
  11. Glibenclamide
  12. Glicaramide
  13. Gliquidone
  14. Glipizide
  15. Glisindamide
  16. Glisolamide
  17. Glycyclamide
  18. Glyhexamide
  19. Hexazinone
  20. Hexylcaine
  21. Hydroxyhexamide
  22. lomustine
  23. Metahexamide
  24. Timegadine
  25. Thiohexamide
  26. U-37883A

Toxicity

[edit]

Cyclohexylamine has a low acute toxicity with LD50 (rat; p.o.) = 0.71 ml/kg[6] Like other amines, it is corrosive.

Cyclohexylamine is listed as an extremely hazardous substance as defined by Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act. The National Institute for Occupational Safety and Health has suggested workers not be exposed to a recommended exposure limit of over 10 ppm (40 mg/m3) over an eight-hour workshift.[2]

References

[edit]
  1. ^ Merck Index, 11th Edition, 2735.
  2. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0168". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ H. K. Hall, J. Am. Chem. Soc. (1957) 79 5441.
  4. ^ Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (2005). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001. ISBN 978-3527306732.
  5. ^ Apps, E. A. (1958). Printing Ink Technology. London: Leonard Hill [Books] Limited. pp. ix.
  6. ^ The Merck Index, 10th Ed. (1983) p.392, Rahway: Merck & Co.
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