cis-1,2-Diaminocyclohexane supplier

Name
cis-1,2-Diaminocyclohexane
EINECS 205-754-6
CAS No. 1436-59-5
Article Data30
CAS DataBase
Density 0.939 g/cm³
Solubility Completely miscible in water
Melting Point 8 °C
Formula C₆H₁₄N₂
Boiling Point 193.643 °C at 760 mmHg
Molecular Weight 114.191
Flash Point 75 °C
Transport Information UN 2735 8/PG 2
Appearance Clear colorless liquid
Safety 26-36/37/39-45
Risk Codes 34
Molecular Structure
Hazard Symbols C
Synonyms 1,2-Cyclohexanediamine,cis- (8CI);(R)(S)-1,2-Diaminocyclohexane;cis-(1S,2R)-1,2-Diaminocyclohexane;cis-1,2-Cyclohexanediamine;cis-1,2-Diaminocyclohexane;meso-1,2-Cyclohexanediamine;meso-1,2-Diaminocyclohexane;
PSA 52.04000
LogP 1.61560

Synthetic route

: 65433-80-9
cis-cyclohexane-1,2-diammonium sulfate

: 1436-59-5
cis-cyclohexane-1,2-diamine

Conditions

Conditions	Yield
With sodium hydroxide In water for 1.16667h;	67%

: 1460-57-7
trans-1,2-cyclohexandiol

A: 4006-50-2
1,2,3,4,6,7,8,9-octahydrophenazine

B: 6850-38-0
2-aminocyclohexanol

C: 1436-59-5
cis-cyclohexane-1,2-diamine

Conditions

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%

...Expand

: 694-83-7
1,2-diaminocyclohexane

: 1436-59-5
cis-cyclohexane-1,2-diamine

Conditions

Conditions	Yield
With DL-tartaric acid In ethanol at 20℃; Reflux; Large scale;	19.2%

: 610-09-3
(1R,2S)-cyclohexane-1,2-dicarboxylic acid

: 1436-59-5
cis-cyclohexane-1,2-diamine

Conditions

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;

: 18886-70-9
cis-cyclohexane-1,2-dicarboxylic acid dihydrazide

: 1436-59-5
cis-cyclohexane-1,2-diamine

Conditions

Conditions	Yield
With hydrogenchloride; sodium nitrite Erhitzen des Reaktionsprodukts mit methanol.KOH bis auf 130grad;

: 2802-07-5
1,3-cyclohexanedionedioxime

A: 1436-59-5
cis-cyclohexane-1,2-diamine

: 3385-21-5, 26772-34-9, 26883-70-5, 115092-57-4
trans-cyclohexane-1,3-diamine

Conditions

Conditions	Yield
With acetic acid; platinum Hydrogenation;

: 75730-13-1, 86694-16-8, 116836-89-6
diethyl (1RS,2SR)-cyclohexane-1,2-diylbiscarbamate

: 1436-59-5
cis-cyclohexane-1,2-diamine

Conditions

Conditions	Yield
With hydrogenchloride at 120℃;

: 875923-28-7
(3aRS,7aSR)-octahydro-2H-benzimidazol-2-one

: 1436-59-5
cis-cyclohexane-1,2-diamine

Conditions

Conditions	Yield
With sulfuric acid at 105℃;

: 10027-79-9
(1R,2S)-1,2-diazidocyclohexane

: 1436-59-5
cis-cyclohexane-1,2-diamine

Conditions

Conditions	Yield
With hydrogen; platinum(IV) oxide In ethanol

: 85782-28-1, 95647-96-4
(3aR,7aS)-2-Ethoxy-3a,4,5,6,7,7a-hexahydro-1H-benzoimidazole

: 1436-59-5
cis-cyclohexane-1,2-diamine

Conditions

Conditions	Yield
With barium dihydroxide at 120℃; for 18h; Yield given;

: 85782-31-6
(1R,6S)-7-Aza-bicyclo[4.1.0]heptane-7-carboximidic acid ethyl ester

: 1436-59-5
cis-cyclohexane-1,2-diamine

Conditions

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

: 110-83-8
cyclohexene

palladium black: palladium black

: 1436-59-5
cis-cyclohexane-1,2-diamine

Conditions

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

: 822-87-7
2-Chlorocyclohexanone

: 1436-59-5
cis-cyclohexane-1,2-diamine

Conditions

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

: trans-2-azido-1-cyclohexanol

: 1436-59-5
cis-cyclohexane-1,2-diamine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Py / 0 - 5 °C 2: NaN3 / dimethylformamide; H2O 3: H2 / PtO2 / ethanol View Scheme

: 10039-14-2, 28141-32-4, 105230-11-3, 116051-21-9, 122673-84-1, 122673-91-0
2-iodo-1-cyclohexanol

: 1436-59-5
cis-cyclohexane-1,2-diamine

Conditions

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

: 286-20-4
cyclohexane-1,2-epoxide

: 1436-59-5
cis-cyclohexane-1,2-diamine

Conditions

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

: trans-2-Azido-cyclohexyl-methan-sulfonat

: 1436-59-5
cis-cyclohexane-1,2-diamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaN3 / dimethylformamide; H2O 2: H2 / PtO2 / ethanol View Scheme

: 694-83-7
1,2-diaminocyclohexane

A: 20439-47-8
(1R,2R)-1,2-diaminocyclohexane

B: 1436-59-5
cis-cyclohexane-1,2-diamine

C: 21436-03-3
(S,S)-1,2-diaminocyclohexane

Conditions

Conditions	Yield
separation by salt formation with (+)-L-tartaric acid;	A 2.0 g B n/a C 0.9 g

...Expand

: 488-31-3, 608-54-8, 608-55-9, 6703-05-5, 10158-64-2, 20869-04-9, 33012-62-3
(2S,4S)-xylaric acid

: 694-83-7
1,2-diaminocyclohexane

A: (1S,2S)-cyclohexane-1,2-diamine (2S,4S)-xylaric acid salt

B: 1436-59-5
cis-cyclohexane-1,2-diamine

Conditions

Conditions	Yield
In methanol at 80℃; for 3h;	A 177.3 g B n/a

...Expand

: 6850-38-0
2-aminocyclohexanol

A: 20439-47-8
(1R,2R)-1,2-diaminocyclohexane

B: 1436-59-5
cis-cyclohexane-1,2-diamine

Conditions

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 %;

: 1436-59-5
cis-cyclohexane-1,2-diamine

: 108-24-7
acetic anhydride

: 70924-77-5
cis-1,2-diacetamidocyclohexane

Conditions

Conditions	Yield
In chloroform for 1h;	100%

: 1436-59-5
cis-cyclohexane-1,2-diamine

: 18209-14-8
N-methylmitomycin A

: C22H29N5O4

Conditions

Conditions	Yield
In methanol at 20℃;	100%

: 1436-59-5
cis-cyclohexane-1,2-diamine

: 70197-13-6
methyltrioxorhenium(VII)

: methyltrioxorhenium(VII)/cis-1,2-diaminocyclohexane adduct

Conditions

Conditions	Yield
In toluene equimolar organic ligand added to Re-compound in toluene at room temp.; filtrated; washed with n-hexane; elem. anal.;	100%

: 1436-59-5
cis-cyclohexane-1,2-diamine

: N-tert-butoxy(benzoylformylimidoyl bromide)

: cis-3-phenyl-4a,5,6,7,8,8a-hexahydroquinoxalin-2(1H)-one O-(tert-butyl)oxime

Conditions

Conditions	Yield
In toluene for 1h; Reflux;	98%

: 1436-59-5
cis-cyclohexane-1,2-diamine

: 7-chloro-5-(3-methylanilino)pyrido[3,4-d]pyridazin-4(3H)-one

: 7-[(2-aminocyclohexyl)amino]-5-(3-methylanilino)pyrido[3,4-d]pyridazin-4(3H)-one

Conditions

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 150 - 170℃; for 3.5h; Microwave irradiation;	98%

: 700-16-3
Pentafluoropyridine

: 1436-59-5
cis-cyclohexane-1,2-diamine

: cis-N,N’’-bis(2,3,5,6-tetrafluoropyridin-4-yl)cyclohexane-1,2-diamine

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran for 24h; Inert atmosphere; Reflux; regioselective reaction;	97%

: 1436-59-5
cis-cyclohexane-1,2-diamine

: 1761-61-1
5-bromosalicyclaldehyde

: N,N'-bis(5-bromosalicylaldehyde)cyclohexanediimine

Conditions

Conditions	Yield
In ethanol at 75℃; for 14h; Inert atmosphere;	97%

: 1436-59-5
cis-cyclohexane-1,2-diamine

: 98-59-9
p-toluenesulfonyl chloride

: 786712-01-4
cis-N,N'-bis-(p-toluenesulfonyl)-1,2-diaminocyclohexane

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 15h;	96%

: 12354-84-6, 12354-85-7
bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]

: 1436-59-5
cis-cyclohexane-1,2-diamine

: [(η5-C5Me5)Ir(cis-1,2-diaminocyclohexane)Cl]Cl

Conditions

Conditions	Yield
In dichloromethane for 0.5h;	96%

: 1436-59-5
cis-cyclohexane-1,2-diamine

: (E)-N-(tert-butyl)-2-oxo-2-phenylacetimidoyl cyanide

: (cis)-N-(tert-butyl)-3-phenyl-4a,5,6,7,8,8a-hexahydroquinoxalin-2-amine

Conditions

Conditions	Yield
In diethylamine at 25℃; for 5h;	96%

: 504-64-3
carbon suboxide

: 1436-59-5
cis-cyclohexane-1,2-diamine

: 135039-13-3
2,6-Diaza-cis-bicyclo<5.4.0>undecan-3,5-dione

Conditions

Conditions	Yield
In chloroform for 1h; Ambient temperature;	95%

: 1436-59-5
cis-cyclohexane-1,2-diamine

: uranyl(VI) acetate dihydrate

: 152523-69-8
3,3'-<<1,1'-binaphthalene>-2,2'-diylbis(oxy-2,1-ethanediyloxy-2,1-ethanediyloxy)>bis<2-hydroxybenzaldehyde>

: {cis-4,5,7,8,16a,17,18,19,20,20a,29,30,32,33-tetradecahydro-10,14:23,27-dimethenobenzo{Z}dinaphtho{2,1-h:1',2'-j}{1,4,7,12,15,18,25,28}hexaoxadiazacyclotetratriacontine-45,46-diolato(2-)-N(16),N(21),O(45),O(46)}dioxouranium * water

Conditions

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%

...Expand

: 1436-59-5
cis-cyclohexane-1,2-diamine

: 1363198-59-7
cis-1,2-dinitrocyclohexane

Conditions

Conditions	Yield
With water; fluorine In dichloromethane; acetonitrile at 20℃; for 0.5h; Inert atmosphere; Flow reactor;	95%

: 1436-59-5
cis-cyclohexane-1,2-diamine

: 7472-70-0
N,N'-bis(4-methylphenyl)ethanediimidoyl dichloride

: cis-

Conditions

Conditions	Yield
With triethylamine for 48h; Ambient temperature;	94%

: 619-22-7
3-(dimethylamino)benzaldehyde

: 1436-59-5
cis-cyclohexane-1,2-diamine

: 2,2’-[cis-1,2-diaminocyclohexanediylbis(nitrilomethylidyne)]bis(5-dimethylamino)phenol

Conditions

Conditions	Yield
In ethanol for 2h; Inert atmosphere; Reflux;	94%

: 4411-26-1
1-adamantylisothiocyanate

: 1436-59-5
cis-cyclohexane-1,2-diamine

: N,N''-(1R,2S)-1,2-cyclohexanediylbis(N'-tricyclo[3.3.1.1(3,7)]dec-1-yl)thiourea

B: 25348-94-1
N,N'-bis(tricyclo[3.3.1.1(3,7)]dec-1-yl)thiourea

Conditions

Conditions	Yield
In tetrahydrofuran for 18h; Reflux; Inert atmosphere;	A 93% B 4%

...Expand

: copper(II) perchlorate hexahydrate

: 1436-59-5
cis-cyclohexane-1,2-diamine

: [Cu(cis-1,2-diaminocyclohexane)2(ClO4)2]

Conditions

Conditions	Yield
In methanol at 20℃; for 2h;	93%

: 590-92-1
3-Bromopropionic acid

: 931-53-3
Cyclohexyl isocyanide

: 1074-12-0
phenylglyoxal hydrate

: 1436-59-5
cis-cyclohexane-1,2-diamine

: (3aR*,5aS*,9aR*)-N-cyclohexyl-1-oxo-4-phenyl -1,2,3,3a,5a,6,7,8,9,9a-decahydropyrrolo[1,2-a]quinoxaline-3a-carboxamide

Conditions

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%

...Expand

: 1436-59-5
cis-cyclohexane-1,2-diamine

: (S)-2,2'-dihydroxy-1,1'-binaphthyl-3-carbaldehyde

: (-)-(S,S)-cis-diaminocyclohexane-BINOL-salen

Conditions

Conditions	Yield
In ethanol at 20℃; for 24h;	92%

: (-)-(S)-1,1'-binaphthalene-3-carboxyaldehyde

: 1436-59-5
cis-cyclohexane-1,2-diamine

: (-)-(S,S)-cis-diaminocyclohexane-BINOL-salen

Conditions

Conditions	Yield
In ethanol Heating;	92%

: 1436-59-5
cis-cyclohexane-1,2-diamine

: 6-chloro-8-(3-methylanilino)-3,4-dihydro-2,7-naphthyridin-1(2H)-one

: 6-[(2-aminocyclohexyl)amino]-8-(3-methylanilino)-3,4-dihydro-2,7-naphthyridin-1(2H)-one

Conditions

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 150 - 170℃; for 3.5h; Microwave irradiation;	92%

: 33904-04-0
4-isothiocyanato-1,2-dimethoxybenzene

: 1436-59-5
cis-cyclohexane-1,2-diamine

: C15H23N3O2S

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 24h;	91%

: zinc perchlorate

: 1436-59-5
cis-cyclohexane-1,2-diamine

: [Zn(cis-1,2-diaminocyclohexane)2(ClO4)2]

Conditions

Conditions	Yield
In methanol at 20℃; for 2h;	91%

: 38460-95-6
undec-10-enoyl chloride

: 1436-59-5
cis-cyclohexane-1,2-diamine

: 1148010-92-7
C17H30N2

Conditions

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%

: 15022-08-9
diallylcarbonate

: 1436-59-5
cis-cyclohexane-1,2-diamine

: 1261082-38-5
allyl ((1R,2S)-2-aminocyclohexyl)carbamate

Conditions

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%

: 1436-59-5
cis-cyclohexane-1,2-diamine

: 90-02-8
salicylaldehyde

: 41013-27-8
(1R,2S)-cis-N,N'-bis(salicylidene)-1,2-cyclohexanediamine

Conditions

Conditions	Yield
In ethanol	89%

: 1436-59-5
cis-cyclohexane-1,2-diamine

: uranyl(VI) acetate dihydrate

: 152523-70-1
3,3'-<<1,1'-binaphthalene>-2,2'-diylbis(oxy-2,1-ethanediyloxy-2,1-ethanediyloxy-2,1-ethanediyloxy)>bis<2-hydroxybenzaldehyde>

: {cis-4,5,7,8,10,11,19a,20,21,22,23,23a,32,33,35,36,38,39-octadecahydro-13,17:26,30-dimethenobenzo{f1}dinaphtho{2,1-k:1',2'-m}{1,4,7,10,15,18,21,24,31,34}octaoxadiazacyclotetracontine-51,52-diolato(2-)-N(19),N(24),O(51),O(52)}dioxouranium

Conditions

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%

...Expand

: 1436-59-5
cis-cyclohexane-1,2-diamine

: uranyl(VI) acetate dihydrate

: 154824-43-8
2-(3-formyl-2-hydroxyphenoxy)-N-<4-(n-octyloxy)phenyl>acetamide

: aqua{(2,2'-(1,2-cyclohexanediylbis(nitrilomethylidyne(2-hydroxy-3,1-phenylene)oxy))bis(N-(4-(n-octyloxy)phenyl)acetamidato))(2-)-N,N',O,O'}dioxouranium trihydrate

Conditions

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%

...Expand

: 1436-59-5
cis-cyclohexane-1,2-diamine

: 7378-94-1
octadec-9-enoyl chloride

: 1148010-93-8
C24H44N2

Conditions

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%

: 1436-59-5
cis-cyclohexane-1,2-diamine

: 109-94-4
formic acid ethyl ester

: 75599-23-4
(1R,2S)-N1,N2- dimethylcyclohexane-1,2-diamine

Conditions

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%

cis-1,2-Diaminocyclohexane Chemical Properties

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

cis-1,2-Diaminocyclohexane Safety Profile

Hazard Codes: Corrosive 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 Specification

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 .

Product Name

cis-1,2-Diaminocyclohexane

Synthetic route

cis-1,2-Diaminocyclohexane Chemical Properties

cis-1,2-Diaminocyclohexane Safety Profile

cis-1,2-Diaminocyclohexane Specification

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