694-83-7

Basic information

• Product Name: 1,2-Diaminocyclohexane
• Synonyms: DACH;1,2-CYCLOHEXANEDIAMINE;1,2-DIAMINOCYCLOHEXANE;(1R,2R)-(-)-1,2-CYCLOHEXANEDIAMINE;(1R,2R)-CYCLOHEXANE-1,2-DIAMINE;(1R)-TRANS-1,2-CYCLOHEXANEDIAMINE;(1R)-(-)-TRANS-1,2-DIAMINOCYCLOHEXANE;(1R)-TRANS-1,2-DIAMINOCYCLOHEXANE
• CAS NO: 694-83-7
• Molecular Formula: C₆H₁₄N₂
• Molecular Weight: 114.19
• EINECS: 211-776-7
• Mol File: 694-83-7.mol
• Article Data: 20

Chemical Properties

• Melting Point: 41-45 °C
• Boiling Point: 92-93 °C18 mm Hg(lit.)
• Flash Point: 169 °F
• Appearance: Clear/Liquid
• Density: 0.931 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.4 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.49(lit.)
• Storage Temp.: 2-8°C
• PKA: 10.76±0.70(Predicted)
• Water Solubility: miscible
• Sensitive: Air Sensitive
• BRN: 506142
• CAS DataBase Reference: 1,2-Diaminocyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Diaminocyclohexane(694-83-7)
• EPA Substance Registry System: 1,2-Diaminocyclohexane(694-83-7)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3259 8/PG 2
• WGK Germany: 3
• RTECS: GU8749500
• F: 34
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 694-83-7(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 694-83-7 differently. You can refer to the following data:
1. suzuki reaction
2. 1,2-Diaminocyclohexane was used in the synthesis of chiral ruthenium(IV)-oxo complexes & bicyclic pyrazine derivatives.
3. 1,2-Diaminocyclohexane was used in the synthesis of chiral ruthenium(IV)-oxo complexes.

General Description

1,2-Diaminocyclohexane undergoes non-templated reaction with homochiral as well as the racemic form of trans-1,2-diaminocyclohexane with terephthaldehyde to yield (3+3)-cyclocondensed molecular triangles. It acts as ligand and forms organotin complexes, having potential applications as metal-based antitumour drugs.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C6H14N2/c7-6(8)4-2-1-3-5-6/h1-5,7-8H2

Synthetic route

cyclohexane-1,2-epoxide (286-20-4) → 1,2-diaminocyclohexane (694-83-7)

Conditions	Yield
With palladium on activated charcoal; ammonia; hydrogen In water at 110 - 250℃; under 18751.9 Torr; Pressure; Temperature; Solvent; Reagent/catalyst; Autoclave;	95%

2-aminocyclohexanecarboxamide (34126-95-9) → 1,2-diaminocyclohexane (694-83-7)

Conditions	Yield
With potassium hypobromite und Erwaermen des Reaktionsprodukts mit Salzsaeure; es liefert die freie Base mit KOH;

cyclohexane-1,2-dicarboxylic acid dihydrazide (32003-11-5) → 1,2-diaminocyclohexane (694-83-7)

Conditions	Yield
beim Abbau nach Curtius; cis(?)-hexahydrophthalic acid dihydrazide;

1,2-diazidocyclohexane (26593-33-9) → 1,2-diaminocyclohexane (694-83-7)

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

N-(1-Ureido-ethyliden)-trans-2-chlor-cyclohexylamin → 1,2-diaminocyclohexane (694-83-7)

Conditions	Yield
With sodium hydroxide In ethylene glycol Heating;

cyclohexene (110-83-8) → 1,2-diaminocyclohexane (694-83-7)

Conditions	Yield
With lithium aluminium tetrahydride; 2; nitrogen(II) oxide 1) THF, 0 deg C, 120 min; 2) THF, -70 deg C, room temperature (overnight), reflux (1 h); Yield given. Multistep reaction;

O-Ethyl-N-(2-nitro-cyclohexyl)-hydroxylamine → 1,2-diaminocyclohexane (694-83-7)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol under 760 Torr; Ambient temperature; Yield given;

2,3-diphenyl-4a,5,6,7,8,8a-hexahydroquinoxaline (96058-39-8) + mineral acid → 1,2-diaminocyclohexane (694-83-7) + benzil (134-81-6)

1-nitrocyclohexene (2562-37-0) → 1,2-diaminocyclohexane (694-83-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaHCO3 / tetrahydrofuran / Ambient temperature 2: H2 / 10percent Pd/C / ethanol / 760 Torr / Ambient temperature View Scheme

2-amino-cyclohexanecarboxylic acid ethyl ester (64162-07-8) → 1,2-diaminocyclohexane (694-83-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 145 °C / im geschlossenen Rohr 2: potassium hypobromite / und Erwaermen des Reaktionsprodukts mit Salzsaeure; es liefert die freie Base mit KOH View Scheme

cyclohexene (110-83-8) + /PBNAI150--221/ → 1,2-diaminocyclohexane (694-83-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaN3, Fe2(SO4)3, FeSO4, aq. H2O2 / methanol 2: H2 / PtO2 / methanol View Scheme
Multi-step reaction with 2 steps 1: (i) Cl2, (ii) /BRN= 906737/ 2: aq. NaOH / ethane-1,2-diol / Heating View Scheme

tricarallylic acid (99-14-9) + platinum(II) chloride → 1,2-diaminocyclohexane (694-83-7)

Conditions	Yield
With silver nitrate In potassium hydroxide; water

1,2-diamino-benzene (95-54-5) → 1,2-diaminocyclohexane (694-83-7)

Conditions	Yield
With sodium tetrahydroborate; ammonia; hydrogen; 5% Rh/C In water at 125℃; under 52476.2 - 104192 Torr; for 3h; Product distribution / selectivity; Autoclave;
With hydrogen In tetrahydrofuran at 110℃; under 75007.5 Torr; for 3h; Autoclave;
With hydrogen In tetrahydrofuran at 130℃; under 37503.8 Torr; for 24h; Autoclave; Green chemistry; chemoselective reaction;

N,N'-bis(salicylidene)cyclohexane-1,2-diamine → salicylaldehyde (90-02-8) + 1,2-diaminocyclohexane (694-83-7)

Conditions	Yield
In chloroform-d1 for 1h; UV-irradiation;

1-(2-azidocyclohexyl)-2-(4-methoxyphenyl)diazene → 1,2-diaminocyclohexane (694-83-7)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 9h;	69 mg

phosphoric acid (86119-84-8, 7664-38-2) + zinc diacetate (557-34-6) + water (7732-18-5) + 1,2-diaminocyclohexane (694-83-7) → Zn3(PO4)2(PO3OH)(H2-1,2-diaminocyclohexane)*2H2O

Conditions	Yield
In water hydrothermal conditions, 180°C;	100%

zinc(II) nitrate (10196-18-6) + phosphoric acid (86119-84-8, 7664-38-2) + water (7732-18-5) + 1,2-diaminocyclohexane (694-83-7) → Zn3(PO4)2(PO3OH)(H2-1,2-diaminocyclohexane)*2H2O

Conditions	Yield
In water hydrothermal conditions, 180°C;	100%

boron phosphate + zinc diacetate (557-34-6) + water (7732-18-5) + 1,2-diaminocyclohexane (694-83-7) → Zn3(PO4)2(PO3OH)(H2-1,2-diaminocyclohexane)*2H2O

Conditions	Yield
In water hydrothermal conditions, molar ratio BPO4:Zn(OAc)2:diaminocyclohexane:water 2:1:2.5:117, , pH=8, 210°C; elem. anal.;	100%

1,2-diaminocyclohexane (694-83-7) + 3,5-dichlorosalicyclaldehyde (90-60-8) → N,N'-bis(3,5-dichlorosalicylidene)-1,2-cyclohexanediamine (413580-19-5)

Conditions	Yield
In ethanol at 60℃;	100%
In ethanol Reflux;

2-hydroxy-3-methyl-1-naphthaldehyde + 1,2-diaminocyclohexane (694-83-7) → C30H30N2O2

Conditions	Yield
In ethanol Reflux;	100%

3-ethyl-2-hydroxy-1-naphthaldehyde + 1,2-diaminocyclohexane (694-83-7) → C32H34N2O2

Conditions	Yield
In ethanol Reflux;	100%

D-tartaric acid (147-71-7) + 1,2-diaminocyclohexane (694-83-7) → (R,R)-1,2-diaminocyclohexane tartrate

Conditions	Yield
With acetic acid In water	99%

trans-{RuCl2(1,3-bis(diphenylphosphino)propane)2} (202289-10-9, 55669-28-8) + 1,2-diaminocyclohexane (694-83-7) → trans-Cl2Ru(1,3-bis(diphenylphosphino)propane)(C6H10(NH2)2) (1299494-45-3, 531498-67-6)

Conditions	Yield
In dichloromethane Ar; dropwise addn. of dichloromethane soln. of diamine to a stirred soln. of Ru complex in the same solvent within 5 min, stirring at room temp.for 10-30 min; filtration, concg. under reduced pressure, pptn. by addn. of diethyl ether, filtration, recrystn. of solid from dichloromethane-n-hexane; elem. anal.;	99%

di-tert-butyl dicarbonate (24424-99-5) + 1,2-diaminocyclohexane (694-83-7) → di-tert-butyl cyclohexane-1,2-diyldicarbamate (1350724-58-1)

Conditions	Yield
With iron oxide In ethanol at 20℃; for 0.25h; Green chemistry; chemoselective reaction;	99%
With 1,3-disulfonic acid imidazolium hydrogen sulfate In neat (no solvent) at 20℃; for 0.0166667h; Green chemistry; chemoselective reaction;	92%
With N-sulfonic acid poly(4-vinyl)pyridinium chloride In neat (no solvent) at 20℃; for 0.0333333h;	92%

1,2-diaminocyclohexane (694-83-7) + Benzoyl isothiocyanate (532-55-8) → CH bis-BTU

Conditions	Yield
In dichloromethane at 5℃; Inert atmosphere;	99%
In dichloromethane at 5 - 20℃; Inert atmosphere;	99%

tricyclo<4.3.1.1.3,8>undecan-4,5-dione (26775-76-8) + 1,2-diaminocyclohexane (694-83-7) → C17H24N2 (106913-34-2)

Conditions	Yield
In ethanol at 25℃; for 48h;	98%

phenyl (chloromethyl)(isothiocyanato)thiophosphinate (136398-79-3) + 1,2-diaminocyclohexane (694-83-7) → C14H20N3OPS2*ClH

Conditions	Yield
In chloroform at 20℃; for 24h;	98%

Homophthalic acid (89-51-0) + 1,2-diaminocyclohexane (694-83-7) → C15H16N2O (1225210-98-9)

Conditions	Yield
for 0.0833333h; Neat (no solvent); Microwave irradiation;	98%

acetic anhydride (108-24-7) + 1,2-diaminocyclohexane (694-83-7) → trans-1,2-diacetyldiaminocyclohexane

Conditions	Yield
With triethylamine at 65 - 80℃; for 6.5h; Temperature; Reagent/catalyst;	98%
In water at 65 - 80℃; for 3.5h; Solvent;	89%

2-hydroxy-3-methylcyclopent-2-en-1-one (80-71-7) + 1,2-diaminocyclohexane (694-83-7) → C12H18N2

Conditions	Yield
In ethanol at 80℃;	98%

1,2-diaminocyclohexane (694-83-7) + benzil (134-81-6) → 2,3-diphenyl-4a,5,6,7,8,8a-hexahydroquinoxaline (96058-39-8)

Conditions	Yield
With alumina supported sulfuric acid In ethanol at 30℃; for 1h;	97%
With potassium hydrogensulfate In ethanol at 20℃; for 0.25h;	95%
With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide In ethanol; water at 20℃; for 0.166667h;	95%

1,2-diaminocyclohexane (694-83-7) + benzoic acid anhydride (93-97-0) → N-(2-aminocyclohexyl)benzamide

Conditions	Yield
In dichloromethane at -78 - 20℃; for 20h; Inert atmosphere;	97%

1,2-diaminocyclohexane (694-83-7) + 1,2-bis(4-methoxyphenyl)-1,2-ethanedione (1226-42-2) → 2,3-di-(p-metoxifenil)-4a,5,6,7,8,8a-hexahidroquinoxalina

Conditions	Yield
With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide In neat (no solvent) at 80℃; for 0.166667h;	96%
In methanol for 1h; Condensation; Heating;

trans-dichlorobis((2-methoxyethyl)diphenylphosphine-O,P)ruthenium(II) (109011-62-3) + 1,2-diaminocyclohexane (694-83-7) → RuCl2((C6H5)2PCH2CH2OCH3)2(H2NC6H10NH2) (620945-35-9, 620949-90-8)

Conditions	Yield
In dichloromethane a soln. of the diamine ligand (10% excess) in CH2Cl2 was added dropwise under Ar to a stirred soln. of Ru-complex in CH2Cl2, the mixt. was stirred for approx. 45 min at room temp.; filtd., concd., Et2O was added, ppt. was filtd. off, dissolved in CH2Cl2, concd., n-hexane was added, ppt. was collected by filtn., washed with n-hexane and dried under vac.; elem. anal.;	96%

2-Hydroxy-4-methoxybenzaldehyde (673-22-3) + 1,2-diaminocyclohexane (694-83-7) → N,N'-bis(4-methoxysalicylidene)cyclohexane-1,2-diamine (1222393-15-8)

Conditions	Yield
In methanol at 20℃; for 0.166667h;	96%

2,7-dibromo-phenanthrene-9,10-dione (84405-44-7) + 1,2-diaminocyclohexane (694-83-7) → 2,7-dibromo-10,11,12,13-tetrahydrodibenzo[a,c]phenazine (1333212-91-1)

Conditions	Yield
Stage #1: 2,7-dibromo-phenanthrene-9,10-dione; rac-diaminocyclohexane In toluene for 1h; Inert atmosphere; Reflux; Dean-Stark; Stage #2: With manganese(IV) oxide In toluene at 84℃; Inert atmosphere;	96%
With toluene-4-sulfonic acid In ethanol Reflux;	49%

1H-indol-2-ylcarboxaldehyde (19005-93-7) + 1,2-diaminocyclohexane (694-83-7) → C24H24N4

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 20℃; for 3h;	96%

zinc(II) acetate dihydrate (5970-45-6) + 3-methoxy-2-hydroxybenzaldehyde (148-53-8) + 1,2-diaminocyclohexane (694-83-7) → [(R,R)-N,N’-bis(3-methoxysalicylidene)-1,2-cyclohexanediaminato]zinc(II)

Conditions	Yield
In ethanol at 20℃; for 24h;	96%

carbon dioxide (124-38-9) + 1,2-diaminocyclohexane (694-83-7) → (R*,R*)-N,N’-cyclohexa-1,2-diylurea (1123-97-3, 7237-97-0, 139121-98-5)

Conditions	Yield
at 180℃; under 75007.5 Torr; for 24h; Autoclave;	95.9%
With potassium hydroxide at 149.84℃; under 60006 Torr; for 10h; Autoclave;	74.2%

2-methoxy-3-methylbenzaldehyde (824-42-0) + 1,2-diaminocyclohexane (694-83-7) → 6,6 '-((1E,1'E)-(cyclohexane-1,2- diylbis(azanylylidene))bis(methanylylidene))bis(2-methylphenol)

Conditions	Yield
In ethanol for 2h; Reflux;	95.2%

1-acetyl-1H-indole-2,3-dione (574-17-4) + 1,2-diaminocyclohexane (694-83-7) → 3-(2-Acetamidophenyl)-4a,5,6,7,8,8a-hexahydro-2(1H)-chinoxazolinon (81965-12-0)

Conditions	Yield
In ethanol for 2h; Heating;	95%

dimedone (126-81-8) + 1,2-diaminocyclohexane (694-83-7) → MC08a

Conditions	Yield
In toluene for 3h; Heating / reflux;	95%

2,3-dicarboxypyrazine (89-01-0) + 1,2-diaminocyclohexane (694-83-7) → C12H12N4O (1225211-01-7)

Conditions	Yield
for 0.0666667h; Neat (no solvent); Microwave irradiation;	95%

succinic acid (110-15-6) + 1,2-diaminocyclohexane (694-83-7) → C10H14N2O (1259371-17-9)

Conditions	Yield
for 0.0666667h; Neat (no solvent); Microwave irradiation;	95%

1,2-diaminocyclohexane (694-83-7) → 1,2-diaminocyclohexane monohydrochloride

Conditions	Yield
With hydrogenchloride In diethyl ether for 2.33333h;	95%

Upstream product

• 34126-95-9 2-aminocyclohexanecarboxamide 
• 32003-11-5 cyclohexane-1,2-dicarboxylic acid dihydrazide 
• 26593-33-9 1,2-diazidocyclohexane 
• 110-83-8 cyclohexene 
• 96058-39-8 2,3-diphenyl-4a,5,6,7,8,8a-hexahydroquinoxaline 
• 2562-37-0 1-nitrocyclohexene 
• 64162-07-8 2-amino-cyclohexanecarboxylic acid ethyl ester 
• 99-14-9 tricarallylic acid 
• 10025-65-7 platinum(II) chloride 
• 95-54-5 1,2-diamino-benzene 
• 286-20-4 cyclohexane-1,2-epoxide 
• 286-18-0 7-azabicyclo[4.1.0]heptane 
• 492-99-9 1,2-cyclohexanedionedioxime 
• 2802-07-5 1,3-cyclohexanedionedioxime 

Downstream Products

• 13291-61-7 trans-1,2-Cyclohexanediaminetetraacetic acid 
• 96058-39-8 2,3-diphenyl-4a,5,6,7,8,8a-hexahydroquinoxaline 
• 1123-97-3 4,5,6,7-Tetrahydrobenzimidazolidin-2-one 
• 138937-34-5 2-benzyl-3a,4,5,6,7,7a-hexahydro-1H-benzimidazole 
• 53959-48-1 3-((Z)-2-oxo-dihydro-furan-3-ylidene)-octahydro-quinoxalin-2-one 
• 106303-76-8 N,N'-(cyclohexane-1,2-diyl)dibenzamide 
• 61796-63-2 N,N'-Bis-(10-undecenoyl)-cyclohexan-1,2-diamin 
• 53959-49-2 3-((Z)-5-methyl-2-oxo-dihydro-furan-3-ylidene)-octahydro-quinoxalin-2-one 
• 53959-50-5 3-((Z)-5-ethyl-2-oxo-dihydro-furan-3-ylidene)-octahydro-quinoxalin-2-one 
• 5769-37-9 1,2-Di-(2-acetyl-1-methylvinylamino)-cyclohexan 
• 72470-21-4 C₂₀H₃₂N₄ 
• 92036-75-4 (+/-)-trans-N,N'-diisopropylcyclohexane-1,2-diamine 
• 30086-64-7 (3aS,7aS)-hexahydro-1H-benzo[d]imidazole-2(3H)-thione 
• 30086-64-7 trans-2-thiohexahydrobenzimidazole 

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