Trans-1,2-Diaminocyclohexane: Difference between revisions

*trans*-1,2-Diaminocyclohexane
Names
	IUPAC name (±)-trans-1,2-Cyclohexanediamine
	Other names 1,2-Diaminocyclohexane; chxn
Identifiers
CAS Number	1121-22-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	420572 ;
ECHA InfoCard	100.127.756
PubChem CID	479307;
UNII	37EKL250EE ;
	InChI InChI=1S/C6H14N2/c7-5-3-1-2-4-6(5)8/h5-6H,1-4,7-8H2/t5-,6-/m0/s1 Key: SSJXIUAHEKJCMH-WDSKDSINSA-N ; InChI=1/C6H14N2/c7-5-3-1-2-4-6(5)8/h5-6H,1-4,7-8H2/t5-,6-/m0/s1 Key: SSJXIUAHEKJCMH-WDSKDSINBK;
	SMILES N[C@H]1CCCC[C@@H]1N;
Properties
Chemical formula	C6H14N2
Molar mass	114.192 g·mol−1
Appearance	Colorless liquid
Density	0.951 g/cm3
Melting point	14 to 15 °C (57 to 59 °F; 287 to 288 K)
Boiling point	79 to 81 °C (174 to 178 °F; 352 to 354 K) 15 mmHg
Hazards
Flash point	69 °C; 156 °F; 342 K
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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trans-1,2-Diaminocyclohexane is an organic compound with the formula C₆H₁₀(NH₂)₂. This diamine is a building block for C₂-symmetric ligands that are useful in asymmetric catalysis.^[1]

A mixture of all three stereoisomers of 1,2-diaminocyclohexane is produced by the hydrogenation of o-phenylenediamine. It is also side product in hydrogenation of adiponitrile. The racemic trans isomer (1:1 mixture of (1R,2R)-1,2-diaminocyclohexane and (1S,2S)-1,2-diaminocyclohexane) can be separated into the two enantiomers using enantiomerically pure tartaric acid as the resolving agent.^[2]

Oxaliplatin, a complex of R,R-diaminocyclohexane, is an important anticancer drug.

Derived ligands

Representative ligands prepared from (1R,2R)- or (1S,2S)-1,2-diaminocyclohexane are diaminocyclohexanetetraacetic acid (CyDTAH₄), Trost ligand, and the salen analogue used in the Jacobsen epoxidation.

References

^ Kouklovsky, Cyrille; Langlois, Yves (2003). "(1S,2S)-1,2-Diaminocyclohexane". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn00145. ISBN 0471936235.
^ Jay F. Larrow and Eric N. Jacobsen (2004). "(R,R)-N,N'-Bis(3,5-Di-tert-Butylsalicylidene)-1,2-Cyclohexanediamino Manganese(III) Chloride, A Highly Enantioselective Epoxidation Catalyst". Organic Syntheses; Collected Volumes, vol. 10, p. 96.

[1] Kouklovsky, Cyrille; Langlois, Yves (2003). "(1S,2S)-1,2-Diaminocyclohexane". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn00145. ISBN 0471936235.

[2] Jay F. Larrow and Eric N. Jacobsen (2004). "(R,R)-N,N'-Bis(3,5-Di-tert-Butylsalicylidene)-1,2-Cyclohexanediamino Manganese(III) Chloride, A Highly Enantioselective Epoxidation Catalyst". Organic Syntheses; Collected Volumes, vol. 10, p. 96.

[1]

[2]

@@ Line 1: / Line 1: @@
+{{Redirect|Dach}}
 {{DISPLAYTITLE:''trans''-1,2-Diaminocyclohexane}}
 {{chembox
+| Verifiedfields = changed
 | Watchedfields = changed
-| verifiedrevid = 401640469
+| verifiedrevid = 470612200
 |Name=''trans''-1,2-Diaminocyclohexane
 |ImageFile=Trans-1,2-Diaminocyclohexane Structural Formulae V.1.svg
@@ Line 9: / Line 11: @@
 |OtherNames= 1,2-Diaminocyclohexane;  chxn
 |Section1= {{Chembox Identifiers
-|  ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
 | ChemSpiderID = 420572
 | InChI = 1/C6H14N2/c7-5-3-1-2-4-6(5)8/h5-6H,1-4,7-8H2/t5-,6-/m0/s1
@@ Line 17: / Line 19: @@
 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChIKey = SSJXIUAHEKJCMH-WDSKDSINSA-N
+| CASNo_Ref = {{cascite|correct|CAS}}
 | CASNo=1121-22-8
+| UNII_Ref = {{fdacite|correct|FDA}}
-|  PubChem = 479307
+| UNII = 37EKL250EE
-|  SMILES = N[C@H]1CCCC[C@@H]1N
+| PubChem = 479307
+| SMILES = N[C@H]1CCCC[C@@H]1N
 }}
 |Section2= {{Chembox Properties
-|  C=6|H=14|N=2
+| C=6|H=14|N=2
-|  Appearance=Colorless liquid
+| Appearance=Colorless liquid
-|  Density=0.951 g/cm<sup>3</sup>
+| Density=0.951 g/cm<sup>3</sup>
-|  MeltingPtC = 14
+| MeltingPtC = 14 to 15
+| BoilingPtC = 79 to 81
-|  MeltingPtCH = 15
+| BoilingPt_notes = 15 mmHg
-|  BoilingPtC = 79
+| Solubility=
-|  BoilingPtCH = 81
+ }}
-|  Boiling_notes = 15 mm Hg
-|  Solubility=
-  }}
 |Section3= {{Chembox Hazards
-|  MainHazards=
+| MainHazards=
-|  FlashPtF = 156
+| FlashPtF = 156
-|  AutoignitionPtC =
+| AutoignitionPtC =
-  }}
+ }}
 }}
-'''''trans''-1,2-Diaminocyclohexane''' is an [[organic compound]] with the [[chemical formula|formula]] C<sub>6</sub>H<sub>10</sub>(NH<sub>2</sub>)<sub>2</sub>.  This [[diamine]] is a building block for [[Chirality (chemistry)|chiral]] [[ligand]]s that are useful in asymmetric catalysis.<ref>Cyrille Kouklovsky, Yves Langlois "(1S,2S)-1,2-Diaminocyclohexane1" in ''[[Encyclopedia of Reagents for Organic Synthesis]]'', 2003; John Wiley & Sons. {{doi|10.1002/047084289X.rn00145}}</ref>
+'''''trans''-1,2-Diaminocyclohexane''' is an [[organic compound]] with the [[chemical formula|formula]] C<sub>6</sub>H<sub>10</sub>(NH<sub>2</sub>)<sub>2</sub>. This [[diamine]] is a building block for [[C2-Symmetric ligands|''C''<sub>2</sub>-symmetric ligand]]s that are useful in [[asymmetric catalysis]].<ref>{{cite book|doi=10.1002/047084289X.rn00145|chapter=(1S,2S)-1,2-Diaminocyclohexane|title=Encyclopedia of Reagents for Organic Synthesis|year=2003|last1=Kouklovsky|first1=Cyrille|last2=Langlois|first2=Yves|isbn=0471936235}}</ref>
-A mixture of ''cis''- and ''trans''-1,2-diaminocyclohexane is produced by the [[hydrogenation]] of [[O-Phenylenediamine|''o''-phenylenediamine]].  The racemic ''trans'' isomer [1:1 mixture of (1''R'',2''R'')-1,2-diaminocyclohexane and (1''S'',2''S'')-1,2-diaminocyclohexane] can be separated into the two enantiomers using enantiomerically pure [[tartaric acid]] as the resolving agent.<ref>{{OrgSynth | author = Jay F. Larrow and Eric N. Jacobsen | title = (R,R)-N,N'-Bis(3,5-Di-tert-Butylsalicylidene)-1,2-Cyclohexanediamino Manganese(III) Chloride, A Highly Enantioselective Epoxidation Catalyst | collvol = 10 | collvolpages = 96| year = 2004 | prep = V75P0001}}</ref>
+A mixture of all three [[stereoisomer]]s of [[1,2-diaminocyclohexane]] is produced by the [[hydrogenation]] of [[O-Phenylenediamine|''o''-phenylenediamine]]. It is also side product in hydrogenation of [[adiponitrile]].  The racemic ''trans'' isomer (1:1 mixture of (1''R'',2''R'')-1,2-diaminocyclohexane and (1''S'',2''S'')-1,2-diaminocyclohexane) can be separated into the two enantiomers using enantiomerically pure [[tartaric acid]] as the resolving agent.<ref>{{OrgSynth | author = Jay F. Larrow and Eric N. Jacobsen | title = (''R'',''R'')-''N'',''N''{{'}}-Bis(3,5-Di-tert-Butylsalicylidene)-1,2-Cyclohexanediamino Manganese(III) Chloride, A Highly Enantioselective Epoxidation Catalyst | collvol = 10 | collvolpages = 96| year = 2004 | prep = V75P0001}}</ref>
+[[File:Oxaliplatin-2D-skeletal.svg|thumb|left|204px|[[Oxaliplatin]], a complex of R,R-diaminocyclohexane, is an important anticancer drug.]]
 ==Derived ligands==
@@ Line 49: / Line 54: @@
 {{reflist}}
-{{DEFAULTSORT:Diaminocyclohexane, trans-1,2-}}
+{{DEFAULTSORT:Diaminocyclohexane, trans-1, 2-}}
-[[Category:Polyamines]]
+[[Category:Diamines]]
 [[Category:Chelating agents]]
+[[Category:Cyclohexanes]]