cis-cyclohexane-1,2-diammonium sulfate
cis-cyclohexane-1,2-diamine
Conditions | Yield |
---|---|
With sodium hydroxide In water for 1.16667h; | 67% |
trans-1,2-cyclohexandiol
A
1,2,3,4,6,7,8,9-octahydrophenazine
B
2-aminocyclohexanol
C
cis-cyclohexane-1,2-diamine
Conditions | Yield |
---|---|
With dodecacarbonyl-triangulo-triruthenium; 4,5-bis((diisopropylphosphanyl)methyl)acridine; ammonia In tert-Amyl alcohol at 170℃; for 21h; Temperature; Inert atmosphere; Schlenk technique; Autoclave; | A 44.8% B n/a C 45.9% |
Conditions | Yield |
---|---|
With DL-tartaric acid In ethanol at 20℃; Reflux; Large scale; | 19.2% |
Conditions | Yield |
---|---|
With chloroform; tris-(2-chloro-ethyl)-amine at 40℃; Erhitzen des Reaktionsprodukts mit methanol.KOH bis auf 130grad; | |
With sodium azide; chloroform; sulfuric acid at 40℃; Erhitzen des Reaktionsprodukts mit methanol.KOH bis auf 130grad; |
cis-cyclohexane-1,2-dicarboxylic acid dihydrazide
cis-cyclohexane-1,2-diamine
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite Erhitzen des Reaktionsprodukts mit methanol.KOH bis auf 130grad; |
1,3-cyclohexanedionedioxime
A
cis-cyclohexane-1,2-diamine
trans-cyclohexane-1,3-diamine
Conditions | Yield |
---|---|
With acetic acid; platinum Hydrogenation; |
diethyl (1RS,2SR)-cyclohexane-1,2-diylbiscarbamate
cis-cyclohexane-1,2-diamine
Conditions | Yield |
---|---|
With hydrogenchloride at 120℃; |
(3aRS,7aSR)-octahydro-2H-benzimidazol-2-one
cis-cyclohexane-1,2-diamine
Conditions | Yield |
---|---|
With sulfuric acid at 105℃; |
(1R,2S)-1,2-diazidocyclohexane
cis-cyclohexane-1,2-diamine
Conditions | Yield |
---|---|
With hydrogen; platinum(IV) oxide In ethanol |
(3aR,7aS)-2-Ethoxy-3a,4,5,6,7,7a-hexahydro-1H-benzoimidazole
cis-cyclohexane-1,2-diamine
Conditions | Yield |
---|---|
With barium dihydroxide at 120℃; for 18h; Yield given; |
(1R,6S)-7-Aza-bicyclo[4.1.0]heptane-7-carboximidic acid ethyl ester
cis-cyclohexane-1,2-diamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / NaI / dimethylformamide / 48 h 2: Ba(OH)2 / 18 h / 120 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) N-bromosuccinimide, 2.) HCl, 3.) NaOH 2: 90 percent / NaI / dimethylformamide / 48 h 3: Ba(OH)2 / 18 h / 120 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 3,6,9-trioxaundecane 2: ethanol; nickel / 135 - 145 °C / 88260.9 - 91938.4 Torr / Hydrogenation 3: sulfuric acid / 105 °C View Scheme |
cis-cyclohexane-1,2-diamine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Py / 0 - 5 °C 2: NaN3 / dimethylformamide; H2O 3: H2 / PtO2 / ethanol View Scheme |
2-iodo-1-cyclohexanol
cis-cyclohexane-1,2-diamine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: NaN3 / ethanol / 24 h / Heating 2: Py / 0 - 5 °C 3: NaN3 / dimethylformamide; H2O 4: H2 / PtO2 / ethanol View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: NaN3, NH4Cl / aq. ethanol / 24 h / Heating 2: Py / 0 - 5 °C 3: NaN3 / dimethylformamide; H2O 4: H2 / PtO2 / ethanol View Scheme | |
Multi-step reaction with 5 steps 1: aq. HI / 0 °C 2: NaN3 / ethanol / 24 h / Heating 3: Py / 0 - 5 °C 4: NaN3 / dimethylformamide; H2O 5: H2 / PtO2 / ethanol View Scheme |
cis-cyclohexane-1,2-diamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaN3 / dimethylformamide; H2O 2: H2 / PtO2 / ethanol View Scheme |
1,2-diaminocyclohexane
A
(1R,2R)-1,2-diaminocyclohexane
B
cis-cyclohexane-1,2-diamine
C
(S,S)-1,2-diaminocyclohexane
Conditions | Yield |
---|---|
separation by salt formation with (+)-L-tartaric acid; | A 2.0 g B n/a C 0.9 g |
(2S,4S)-xylaric acid
1,2-diaminocyclohexane
B
cis-cyclohexane-1,2-diamine
Conditions | Yield |
---|---|
In methanol at 80℃; for 3h; | A 177.3 g B n/a |
2-aminocyclohexanol
A
(1R,2R)-1,2-diaminocyclohexane
B
cis-cyclohexane-1,2-diamine
Conditions | Yield |
---|---|
Stage #1: 2-aminocyclohexanol In ethanol for 1h; Stage #2: With ammonia; hydrogen In ethanol at 160℃; under 3000.3 - 11251.1 Torr; for 16h; Pressure; Reagent/catalyst; Solvent; Temperature; Overall yield = 98 %; |
cis-cyclohexane-1,2-diamine
acetic anhydride
cis-1,2-diacetamidocyclohexane
Conditions | Yield |
---|---|
In chloroform for 1h; | 100% |
Conditions | Yield |
---|---|
In methanol at 20℃; | 100% |
cis-cyclohexane-1,2-diamine
methyltrioxorhenium(VII)
Conditions | Yield |
---|---|
In toluene equimolar organic ligand added to Re-compound in toluene at room temp.; filtrated; washed with n-hexane; elem. anal.; | 100% |
cis-cyclohexane-1,2-diamine
Conditions | Yield |
---|---|
In toluene for 1h; Reflux; | 98% |
cis-cyclohexane-1,2-diamine
Conditions | Yield |
---|---|
In 1-methyl-pyrrolidin-2-one at 150 - 170℃; for 3.5h; Microwave irradiation; | 98% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran for 24h; Inert atmosphere; Reflux; regioselective reaction; | 97% |
Conditions | Yield |
---|---|
In ethanol at 75℃; for 14h; Inert atmosphere; | 97% |
cis-cyclohexane-1,2-diamine
p-toluenesulfonyl chloride
cis-N,N'-bis-(p-toluenesulfonyl)-1,2-diaminocyclohexane
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; for 15h; | 96% |
bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]
cis-cyclohexane-1,2-diamine
Conditions | Yield |
---|---|
In dichloromethane for 0.5h; | 96% |
cis-cyclohexane-1,2-diamine
Conditions | Yield |
---|---|
In diethylamine at 25℃; for 5h; | 96% |
carbon suboxide
cis-cyclohexane-1,2-diamine
2,6-Diaza-cis-bicyclo<5.4.0>undecan-3,5-dione
Conditions | Yield |
---|---|
In chloroform for 1h; Ambient temperature; | 95% |
cis-cyclohexane-1,2-diamine
3,3'-<<1,1'-binaphthalene>-2,2'-diylbis(oxy-2,1-ethanediyloxy-2,1-ethanediyloxy)>bis<2-hydroxybenzaldehyde>
Conditions | Yield |
---|---|
With barium triflate In tetrahydrofuran refluxing (30 min); solvent evapn., dissoln. (CH2Cl2), washing (water, aq. Na2SO4), evapn., flash column chromy. (MeOH/CH2Cl2 3/97), pptn. (CH2Cl2/cyclohexane); elem. anal.; | 95% |
cis-cyclohexane-1,2-diamine
cis-1,2-dinitrocyclohexane
Conditions | Yield |
---|---|
With water; fluorine In dichloromethane; acetonitrile at 20℃; for 0.5h; Inert atmosphere; Flow reactor; | 95% |
Conditions | Yield |
---|---|
With triethylamine for 48h; Ambient temperature; | 94% |
Conditions | Yield |
---|---|
In ethanol for 2h; Inert atmosphere; Reflux; | 94% |
1-adamantylisothiocyanate
cis-cyclohexane-1,2-diamine
B
N,N'-bis(tricyclo[3.3.1.1(3,7)]dec-1-yl)thiourea
Conditions | Yield |
---|---|
In tetrahydrofuran for 18h; Reflux; Inert atmosphere; | A 93% B 4% |
cis-cyclohexane-1,2-diamine
Conditions | Yield |
---|---|
In methanol at 20℃; for 2h; | 93% |
3-Bromopropionic acid
Cyclohexyl isocyanide
phenylglyoxal hydrate
cis-cyclohexane-1,2-diamine
Conditions | Yield |
---|---|
Stage #1: phenylglyoxal hydrate; cis-cyclohexane-1,2-diamine In methanol at 20℃; for 0.166667h; Ugi Condensation; Stage #2: 3-Bromopropionic acid; Cyclohexyl isocyanide In methanol for 24h; diastereoselective reaction; | 93% |
cis-cyclohexane-1,2-diamine
Conditions | Yield |
---|---|
In ethanol at 20℃; for 24h; | 92% |
cis-cyclohexane-1,2-diamine
Conditions | Yield |
---|---|
In ethanol Heating; | 92% |
cis-cyclohexane-1,2-diamine
Conditions | Yield |
---|---|
In 1-methyl-pyrrolidin-2-one at 150 - 170℃; for 3.5h; Microwave irradiation; | 92% |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 24h; | 91% |
Conditions | Yield |
---|---|
In methanol at 20℃; for 2h; | 91% |
Conditions | Yield |
---|---|
Stage #1: undec-10-enoyl chloride; cis-cyclohexane-1,2-diamine In 1,4-dioxane at 0 - 20℃; Stage #2: With boron trifluoride diethyl etherate In 1,4-dioxane at 130℃; | 90% |
diallylcarbonate
cis-cyclohexane-1,2-diamine
allyl ((1R,2S)-2-aminocyclohexyl)carbamate
Conditions | Yield |
---|---|
With Novozyme 435 In toluene at 20℃; for 96h; Enzymatic reaction; | 90% |
With candida antarctica novozyme-435 In toluene at 20℃; for 96h; Enzymatic reaction; | 90% |
cis-cyclohexane-1,2-diamine
salicylaldehyde
(1R,2S)-cis-N,N'-bis(salicylidene)-1,2-cyclohexanediamine
Conditions | Yield |
---|---|
In ethanol | 89% |
cis-cyclohexane-1,2-diamine
3,3'-<<1,1'-binaphthalene>-2,2'-diylbis(oxy-2,1-ethanediyloxy-2,1-ethanediyloxy-2,1-ethanediyloxy)>bis<2-hydroxybenzaldehyde>
Conditions | Yield |
---|---|
With barium triflate In tetrahydrofuran refluxing (30 min); solvent evapn., dissoln. (CH2Cl2), washing (water, aq. Na2SO4), evapn., flash column chromy. (MeOH/CH2Cl2 3/97), pptn. (CH2Cl2/cyclohexane); elem. anal.; | 89% |
cis-cyclohexane-1,2-diamine
2-(3-formyl-2-hydroxyphenoxy)-N-<4-(n-octyloxy)phenyl>acetamide
Conditions | Yield |
---|---|
With H2O In methanol under Ar; the aldehyde and the amine were refluxed in methanol for 1 h, UO2(OAc)2 in methanol was added, refluxed for 1 h; cooled, filtered, washed with methanol; elem. anal.; | 89% |
Conditions | Yield |
---|---|
Stage #1: cis-cyclohexane-1,2-diamine; octadec-9-enoyl chloride In 1,4-dioxane at 0 - 20℃; Stage #2: With boron trifluoride diethyl etherate In 1,4-dioxane at 130℃; | 89% |
cis-cyclohexane-1,2-diamine
formic acid ethyl ester
(1R,2S)-N1,N2- dimethylcyclohexane-1,2-diamine
Conditions | Yield |
---|---|
Stage #1: cis-cyclohexane-1,2-diamine; formic acid ethyl ester Reflux; Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; Reflux; Stage #3: With water; sodium hydroxide In tetrahydrofuran | 89% |
Molecular Structure of cis-1,2-Diaminocyclohexane (CAS No.1436-59-5):
Molecular Formula: C6H14N2
Molecular Weight: 114.19
CAS No: 1436-59-5
XLogP3-AA: -0.3
H-Bond Donor: 2
H-Bond Acceptor: 2
Rotatable Bond Count: 0
Exact Mass: 114.115698
MonoIsotopic Mass: 114.115698
Topological Polar Surface Area: 52
Heavy Atom Count: 8
Formal Charge: 0
Complexity: 62.9
Isotope Atom Count: 0
Defined Atom StereoCenter Count: 0
Undefined Atom StereoCenter Count: 2
Defined Bond StereoCenter Count: 0
Undefined Bond StereoCenter Count: 0
Covalently-Bonded Unit Count: 1
Index of Refraction: 1.483
Molar Refractivity: 34.77 cm3
Molar Volume: 121.5 cm3
Surface Tension: 37 dyne/cm
Density: 0.939 g/cm3
Flash Point: 75 °C
Enthalpy of Vaporization: 42.98 kJ/mol
Boiling Point: 193.6 °C at 760 mmHg
Vapour Pressure: 0.46 mmHg at 25°C
Chemical Properties Clear colorless liquid
IUPAC Name: Cyclohexane-1,2-diamine
Canonical SMILES: C1CCC(C(C1)N)N
InChI: InChI=1S/C6H14N2/c7-5-3-1-2-4-6(5)8/h5-6H,1-4,7-8H2
InChIKey: SSJXIUAHEKJCMH-UHFFFAOYSA-N
Hazard Codes: C
Risk Statements: 34
R34:Causes burns.
Safety Statements: 26-36/37/39-45
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2735 8/PG 2
WGK Germany: 3
F: 10-34
HazardClass: 8
PackingGroup: II
cis-1,2-Diaminocyclohexane (CAS No.1436-59-5), it also can be called 1,2-Cyclohexanediamine ; Cyclohexane-1,2-diamine ; 1,2-Diaminocyclohexane, mixture of cis and trans .
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