3114-70-3

Basic information

• Product Name: 1,4-CYCLOHEXANEDIAMINE
• Synonyms: 1,4-cyclohexylenediamine;hexahydro-1,4-phenylenediamine;1,4-DIAMINOCYCLOHEXANE;1,4-CYCLOHEXANEDIAMINE;1,4-DIAMINECYCLOHEXANE;cyclohexane-1,4-diamine;CIS OR TRANS OR MIXTURE-1,4-DIAMINECYCLOHEXANE;1,4-Diaminocyclohexan
• CAS NO: 3114-70-3
• Molecular Formula: C₆H₁₄N₂
• Molecular Weight: 114.19
• EINECS: 221-483-6
• Product Categories: amino acid
• Mol File: 3114-70-3.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 199.4 °C at 760 mmHg
• Flash Point: 80 °C
• Appearance: /
• Density: 0.939 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• PKA: 10.78±0.70(Predicted)
• CAS DataBase Reference: 1,4-CYCLOHEXANEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-CYCLOHEXANEDIAMINE(3114-70-3)
• EPA Substance Registry System: 1,4-CYCLOHEXANEDIAMINE(3114-70-3)

Safety Data

• Statements: 22-34
• Safety Statements: 23-26-36/37/39-45
• RIDADR: 2735
• RTECS: GU8750500
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 3114-70-3(Hazardous Substances Data)

Usage

Uses

1,4-cyclohexanediamine be used as organic intermediates and epoxy curing agents.

InChI:InChI=1/C6H14N2/c7-5-1-2-6(8)4-3-5/h5-6H,1-4,7-8H2

Synthetic route

1,4-Cyclohexanedione (637-88-7) → trans-1,4-diaminocyclohexane (3114-70-3)

Conditions	Yield
With Co-doped zirconium dioxide; ammonia; hydrogen; N-butylamine In methanol at 99.84℃; for 10h; Autoclave; chemoselective reaction;	90%
With (S)-1-phenyl-ethylamine; pyridoxal 5'-phosphate; pQR1108 In aq. phosphate buffer; dimethyl sulfoxide at 30℃; for 18h; pH=8; Enzymatic reaction;
With amine transaminase-200; isopropylamine Enzymatic reaction;

1,4-Cyclohexanediol (556-48-9) → trans-1,4-diaminocyclohexane (3114-70-3) + p-hydroxycyclohexylamine (6850-65-3)

Conditions	Yield
With ammonia; hydrogen; Co/Fe catalyst at 165 - 195℃; under 101260 Torr; Contact time 20000 - 40000 g.s/mol;	A 51% B 6%

1,4-Cyclohexanediol (556-48-9) → trans-1,4-diaminocyclohexane (3114-70-3) + p-hydroxycyclohexylamine (6850-65-3) + N-Cyclohexyl-cyclohexane-1,4-diamine + cyclohexylamine (108-91-8) + 4-(4-amino-cyclohexylamino)-cyclohexanol + N-(4-amino-cyclohexyl)-1,4-cyclo-hexanediamine

Conditions	Yield
With supercritical ammonia; cobalt catalyst-iron

hydrogenchloride (7647-01-0) + acetic acid (64-19-7) + 4-nitro-aniline (100-01-6) + colloidal platinum → trans-1,4-diaminocyclohexane (3114-70-3) + cyclohexylamine (108-91-8) + N-cyclohexyl-cyclohexanamine (101-83-7)

Conditions	Yield
at 65 - 70℃; Hydrogenation;

ethanol (64-17-5) + cyclohexane-1,4-dione dioxime (10220-83-4, 6212-72-2, 6133-84-2) + sodium → trans-1,4-diaminocyclohexane (3114-70-3)

(cis-4-benzyloxycarbonylaminocyclohexyl)-carbamic acid benzyl ester (509142-45-4) → trans-1,4-diaminocyclohexane (3114-70-3)

Conditions	Yield
With hydrogen; 5%-palladium/activated carbon In methanol at 20℃; for 60h;

1,4-Cyclohexanediol (556-48-9) → trans-1,4-diaminocyclohexane (3114-70-3)

Conditions	Yield
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In tert-Amyl alcohol at 140℃; under 12001.2 Torr; for 20h; Inert atmosphere; Autoclave; chemoselective reaction;	71 %Chromat.
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In tert-Amyl alcohol at 140℃; for 20h; Inert atmosphere; Cooling;

1,4-Cyclohexanedione (637-88-7) → cis-4-aminocyclohexanol + trans-1,4-diaminocyclohexane (3114-70-3) + 1,4-Cyclohexanediol (556-48-9)

Conditions	Yield
Stage #1: 1,4-Cyclohexanedione With keto reductases from Lactobacillus kefir; isopropyl alcohol In aq. phosphate buffer at 30℃; pH=7; Enzymatic reaction; Stage #2: With amine transaminase-200; isopropylamine stereoselective reaction;	A n/a B n/a C n/a

1,4-Cyclohexanedione (637-88-7) → cis-4-aminocyclohexanol + trans-1,4-diaminocyclohexane (3114-70-3)

Conditions	Yield
With amine transaminase-200; keto reductases from Lactobacillus kefir; isopropylamine In aq. phosphate buffer at 30℃; for 48h; pH=7.5; Enzymatic reaction; stereoselective reaction;	A n/a B n/a

1,4-phenylenediamine (106-50-3) → trans-1,4-diaminocyclohexane (3114-70-3)

Conditions	Yield
With hydrogen In tetrahydrofuran at 130℃; under 37503.8 Torr; for 2.5h; Catalytic behavior; Reagent/catalyst; Temperature; Pressure; Autoclave; Green chemistry; chemoselective reaction;	70.5 %Chromat.

carbonic acid dimethyl ester (616-38-6) + 1,4-phenylenediamine (106-50-3) → trans-1,4-diaminocyclohexane (3114-70-3) + C8H16N2O2

Conditions	Yield
With hydrogen; sodium carbonate at 160℃; under 62256.2 Torr; for 2h; Autoclave;	A 30 %Chromat. B 20 %Chromat.

[1,3]-dioxolan-2-one (96-49-1) + 1,4-phenylenediamine (106-50-3) → trans-1,4-diaminocyclohexane (3114-70-3) + C9H18N2O3

Conditions	Yield
With hydrogen; sodium carbonate at 160℃; under 62256.2 Torr; for 2h; Autoclave;	A 16 %Chromat. B 74 %Chromat.

trans-1,4-diaminocyclohexane (3114-70-3) → 1,4-cyclohexyl di-isocyanate (19207-18-2)

Conditions	Yield
With carbon dioxide; triethylamine; trichlorophosphate In dichloromethane	99%

formic acid (64-18-6) + trans-1,4-diaminocyclohexane (3114-70-3) → N-(4-formamidocyclohexyl)formamide (35197-79-6)

Conditions	Yield
In toluene at 120℃; for 16h; Inert atmosphere;	99%

trans-1,4-diaminocyclohexane (3114-70-3) + acrylonitrile (107-13-1) → N,N'-bis(2-cyanoethyl)cyclohexane-1,4-diamine (1142-40-1)

Conditions	Yield
at 80 - 100℃; for 3h;	95%
Stage #1: trans-1,4-diaminocyclohexane at 80℃; Stage #2: acrylonitrile at 80 - 100℃; for 3h;	92.8%

trans-1,4-diaminocyclohexane (3114-70-3) + (4-bromophenyl)-[2-chloro-9-(tetrahydro-pyran-2-yl)-9H-purin-6-yl]amine → N2-(4-aminocyclohexyl)-N6-(4-bromophenyl)-9-(tetrahydropyran-2-yl)-9H-purine-2,6-diamine

Conditions	Yield
In ethylene glycol at 160℃; for 4h; Inert atmosphere; Sealed tube;	94%

trans-1,4-diaminocyclohexane (3114-70-3) + (2-chloro-9-cyclopentyl-9H-purin-6-yl)-[4-(2-oxa-6-aza-spiro[3.3]hept-6-yl)-phenyl]-amine → N2-(4-amino-cyclohexyl)-9-cyclopentyl-N6-[4-(2-oxa-6-aza-spiro[3.3]hept-6-yl)-phenyl]-9H-purine-2,6-diamine

Conditions	Yield
In ethylene glycol at 160℃; for 4h; Inert atmosphere; Sealed tube;	94%

trans-1,4-diaminocyclohexane (3114-70-3) + (2-chloro-9-cyclopentyl-9H-purin-6-yl)-(6-morpholin-4-yl-pyridin-3-yl)-amine → N2-(4-amino-cyclohexyl)-9-cyclopentyl-N6-(6-morpholin-4-yl-pyridin-3-yl)-9H-purine-2,6-diamine

Conditions	Yield
In ethylene glycol at 160℃; for 4h; Inert atmosphere; Sealed tube;	94%

trans-1,4-diaminocyclohexane (3114-70-3) + 1,3-di(tert-butyloxycarbonyl)-2-(trifluoromethylsulfonyl)guanidine (207857-15-6) → C17H32N4O4

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 24h;	94%

trans-1,4-diaminocyclohexane (3114-70-3) + 2-chloro-6-((3-iodobenzyl)amino)-9-cyclopentylpurine (240820-01-3) → 2-[trans-(4-aminocyclohexyl)amino]-6-(3-iodobenzylamino)-9-cyclopentylpurine

Conditions	Yield
at 140℃; for 18h;	92%

trans-1,4-diaminocyclohexane (3114-70-3) + (2-chloro-9-cyclopentyl-9H-purin-6-yl)-(4-pyrrolidin-1-yl-phenyl)amine → N2-(4-amino-cyclohexyl)-9-cyclopentyl-N6-(4-pyrrolidin-1-yl-phenyl)-9H-purine-2,6-diamine

Conditions	Yield
In ethylene glycol at 160℃; for 4h; Inert atmosphere; Sealed tube;	92%

trans-1,4-diaminocyclohexane (3114-70-3) + (2-chloro-9-cyclopentyl-9H-purin-6-yl)-(4-morpholin-4-ylmethyl-phenyl)-amine → N2-(4-amino-cyclohexyl)-9-cyclopentyl-N6-(4-morpholin-4-ylmethyl-phenyl)-9H-purine-2,6-diamine

Conditions	Yield
In ethylene glycol at 160℃; for 4h; Inert atmosphere; Sealed tube;	92%

trans-1,4-diaminocyclohexane (3114-70-3) + acetaldehyde (75-07-0) + phosphonic acid diethyl ester (762-04-9) → C18H40N2O6P2

Conditions	Yield
With triethylamine In n-heptan1ol at 70℃; for 8h; Mannich Aminomethylation;	90.1%

trans-1,4-diaminocyclohexane (3114-70-3) + 2-(chloroselenyl)-5-fluorobenzoyl chloride (1381782-04-2) → C20H16F2N2O2Se2 (1381781-91-4)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	89%

trans-1,4-diaminocyclohexane (3114-70-3) + 7,7-dimethyl-2,3-bis(5-carboxythiophen-2-yl)-5,6-bis(trifluoromethyl)-2,5-norbornadiene (365220-36-6) → polymer, Mn 42700, Mw/Mn 5.77 by GPC; monomer(s): 7,7-dimethyl-2,3-bis(5-carboxythiophen-2-yl)-5,6-bis(trifluoromethyl)-2,5-norbornadiene; 1,4-diaminocyclohexane

Conditions	Yield
With diphenylphosphoranyl azide; triethylamine In N,N-dimethyl-formamide at 20℃; for 48h;	88%

vanadyl(IV) sulfate dihydrate + trans-1,4-diaminocyclohexane (3114-70-3) + water (7732-18-5) + germanium dioxide → C6H10(NH3)2(2+)*Ge2V4O12(OH)2(2-)*2H2O=[C6H10(NH3)2][Ge2V4O12(OH)2]*2H2O

Conditions	Yield
With HF In water High Pressure; GeO2, VOSO4*4H2O, 1,4-diaminocyclohexane, HF, H2O placed into autoclave;heated at 170°C for 7 ds; initial pH was 10, final pH - 9.5; filtered; washed (H2O);	88%

trans-1,4-diaminocyclohexane (3114-70-3) + [4-(4-benzylpiperazin-1-yl)phenyl](2-chloro-9-cyclopentyl-9H-purin-6-yl)amine → N2-(4-aminocyclohexyl)-N6-[4-(4-benzylpiperazin-1-yl)phenyl]-9-cyclopentyl-9H-purine-2,6-diamine

Conditions	Yield
In ethylene glycol at 160℃; for 4h; Inert atmosphere; Sealed tube;	88%

trans-1,4-diaminocyclohexane (3114-70-3) + 4-(pyridin-4-yl)benzaldehyde (99163-12-9) → C30H28N4

Conditions	Yield
In acetonitrile at 20℃; for 4h; Reflux;	85%

trans-1,4-diaminocyclohexane (3114-70-3) + 4-bromophenyl-(2-chloro-9-isopropyl-9H-purin-6-yl)amine (945895-34-1) → N2-(4-amino-cyclohexyl)-N6-(4-bromophenyl)-9-isopropyl-9H-purine-2,6-diamine

Conditions	Yield
In ethylene glycol at 160℃; for 4h; Inert atmosphere; Sealed tube;	85%

trans-1,4-diaminocyclohexane (3114-70-3) + (2-chloro-9-cyclopentyl-9H-purin-6-yl)-(4-chlorophenyl)amine → N2-(4-aminocyclohexyl)-N6-(4-chlorophenyl)-9-cyclopentyl-9H-purine-2,6-diamine

Conditions	Yield
In ethylene glycol at 160℃; for 4h; Inert atmosphere; Sealed tube;	84%

trans-1,4-diaminocyclohexane (3114-70-3) + 1-chloro-2,4-dinitro-benzene (97-00-7) → N,N'-bis(2,4-dinitrophenyl)cyclohexane-1,4-diamine

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 24h;	84%

trans-1,4-diaminocyclohexane (3114-70-3) + propionyl chloride (79-03-8) → N,N'-bis(propanoyl)-1,4-cyclohexanediamine

Conditions	Yield
With dmap In dichloromethane at 10 - 20℃; for 6h;	83.8%

4,7-dichloroquinoline (86-98-6) + trans-1,4-diaminocyclohexane (3114-70-3) → cis-N-(7-chloro-quinolin-4-yl)-cyclohexyl-1,4-diamine (289628-25-7)

Conditions	Yield
at 110℃; for 18h;	82%
Stage #1: 4,7-dichloroquinoline; trans-1,4-diaminocyclohexane at 110℃; for 18h; Inert atmosphere; Stage #2: With sodium hydroxide In water at 20℃;	82%

trans-1,4-diaminocyclohexane (3114-70-3) + (9-benzyl-2-chloro-9H-purin-6-yl)-(4-bromophenyl)amine (125802-46-2) → N2-(4-aminocyclohexyl)-9-benzyl-N6-(4-bromophenyl)-9H-purine-2,6-diamine

Conditions	Yield
In ethylene glycol at 160℃; for 4h; Inert atmosphere; Sealed tube;	82%

trans-1,4-diaminocyclohexane (3114-70-3) + (2-chloro-9-cyclopentyl-9H-purin-6-yl)-[4-(4-ethyl-piperazin-1-yl)-phenyl]-amine → N2-(4-aminocyclohexyl)-9-cyclopentyl-N6-[4-(4-ethylpiperazin-1-yl)phenyl]-9H-purine-2,6-diamine

Conditions	Yield
In ethylene glycol at 160℃; for 4h; Inert atmosphere; Sealed tube;	82%

vanadia + As2O5*3H2O + trans-1,4-diaminocyclohexane (3114-70-3) + hydrogen fluoride (7664-39-3) → [1,4-diaminocyclohexane(+2H)]0.5[(VO)(HAsO4)F]

Conditions	Yield
In water; butan-1-ol High Pressure; V2O3 and As2O5 were dissolved in mixt. of H2O and butanol; HF was added;diaminocyclohexane was added in order to fix pH 1.5; stirred; sealed in pressure vessel; heated at 170°C for 5 d; slowly cooled to room temp.; elem. anal.;	80%

trans-1,4-diaminocyclohexane (3114-70-3) + O-α-D-glucopyranosyl-(1-4)-D-glucono-1,5-lactone (5965-65-1, 42776-28-3, 52762-22-8) → 6-maltobionamidocyclohexyl amine (1488347-19-8)

Conditions	Yield
In N,N-dimethyl-formamide at 0 - 20℃; for 12h; Inert atmosphere;	79.5%

trans-1,4-diaminocyclohexane (3114-70-3) + 4-(bromophenyl)(2-chloro-9-cyclopentyl-9H-purin-6-yl)amine → N2-(4-aminocyclohexyl)-N6-(4-bromophenyl)-9-cyclopentyl-9H-purine-2,6-diamine

Conditions	Yield
In ethylene glycol at 160℃; for 4h; Inert atmosphere; Sealed tube;	79%

trans-1,4-diaminocyclohexane (3114-70-3) + lactobionolactone (5965-65-1, 42776-28-3, 52762-22-8) → 6-lactobionamido cyclohexylamine (1488333-49-8)

Conditions	Yield
In N,N-dimethyl-formamide at 0 - 20℃; for 12h; Inert atmosphere;	78.7%

(dimethylglyoxime)2(H2O)CoMe + dichloromethane (75-09-2) + trans-1,4-diaminocyclohexane (3114-70-3) → [(cobalt(III)(methyl)(dimethylglyoxime(-H))2)2(1,6-diaminohexane)]*1.5CH2Cl2

Conditions	Yield
In methanol soln. of Co complex (0.31 mmol) added to soln. of C6H4(NH2)2 (0.15 mmol), filtered, H2O added, solvent. evapd. partially, ppt. filtered, dissolved in CH2Cl2; crystd. by slow diffusion in n-heptane; elem. anal.;	77%

trans-1,4-diaminocyclohexane (3114-70-3) + 1-oxa-3,6-dithiacycloheptane (1376771-60-6) → 3,3'-(cyclohexane-1,4-diyl)di-1,5,3-dithiazepane

Conditions	Yield
With samarium(III) chloride hexahydrate In ethanol; chloroform at 20℃; for 3.5h; Inert atmosphere;	77%

Upstream product

• 616-38-6 carbonic acid dimethyl ester 
• 106-50-3 1,4-phenylenediamine 
• 96-49-1 [1,3]-dioxolan-2-one 
• 637-88-7 1,4-Cyclohexanedione 
• 509142-45-4 (cis-4-benzyloxycarbonylaminocyclohexyl)-carbamic acid benzyl ester 
• 556-48-9 1,4-Cyclohexanediol 
• 64-17-5 ethanol 
• 10220-83-4 cyclohexane-1,4-dione dioxime 
• 7647-01-0 hydrogenchloride 
• 64-19-7 acetic acid 
• 100-01-6 4-nitro-aniline 

Downstream Products

• 17577-11-6 trans-1,2-diaminocyclohexane-N,N,N',N'-tetraacetic acid 
• 97159-36-9 1,4-bis-(morpholine-4-sulfonylamino)-cyclohexane 
• 1488347-19-8 6-maltobionamidocyclohexyl amine 
• 1488347-20-1 6-maltobionamidocyclohexyl methacrylamide 
• 1488333-49-8 6-lactobionamido cyclohexylamine 
• 1488333-50-1 6-lactobionamidocyclohexyl methacrylamide 
• 1548175-10-5 N-(4-aminocyclohexyl)-5H-dibenz[b,f]azepine-5-carboxamide 
• 1452561-26-0 N₂-[4-((1H-benzo[d]imidazol-2-yl)amino)cyclohexyl]pyridine-2,3-diamine 
• 1452561-25-9 N¹-(1H-benzo[d]imidazol-2-yl)-N⁴-(3-nitropyridin-2-yl)cyclohexane-1,4-diamine 
• 1421112-24-4 N¹-(3-nitropyridin-2-yl)cyclohexane-1,4-diamine 
• 1445768-08-0 C₁₄H₁₇ClF₃N₃O 
• 1445768-07-9 C₁₃H₁₇Cl₂N₃O 
• 1155100-77-8 C₁₄H₂₁N₃O 
• 1155633-86-5 C₁₄H₂₁N₃O 

Relevant articles and documents

Ru/g-C3N4as an efficient catalyst for selective hydrogenation of aromatic diamines to alicyclic diamines

A series of Ru/g-C3N4materials with highly dispersed Ru were firstly prepared by an ultrasonic impregnation method using carbon nitride as a support. The catalysts were characterized by various techniques including BET and elemental analysis, ICP-AES, XPS, XRD, CO2-TPD and TEM. The results demonstrated that Ru/g-C3N4materials with a mesoporous structure and highly dispersed Ru were successfully prepared. The chemo-selective hydrogenation ofp-phenylenediamine (PPDA) to 1,4-cyclohexanediamine (CHDA) over Ru/g-C3N4as a model reaction was investigated in detail. PPDA conversion of 100% with a CHDA selectivity of more than 86% could be achieved under mild conditions. It can be inferred that the carbon nitride support possessed abundant basic sites and the Ru/g-C3N4-Tcatalysts provided suitable basicity for the aromatic ring hydrogenation. Compared to the N-free Ru/C catalyst, the involvement of nitrogen species in Ru/g-C3N4remarkably improved the catalytic performance. In addition, the recyclability of the catalyst demonstrated that the aggregation of Ru nanoparticles was responsible for the decrease of the catalytic activity. Furthermore, this strategy also could be expanded to the selective hydrogenation of other aromatic diamines to alicyclic diamines.

One-pot Synthesis of 4-Aminocyclohexanol Isomers by Combining a Keto Reductase and an Amine Transaminase

The efficient multifunctionalization by one-pot or cascade catalytic systems has developed as an important research field, but is often challenging due to incompatibilities or cross-reactivities of the catalysts leading to side product formation. Herein we report the stereoselective preparation of cis- and trans-4-aminocyclohexanol from the potentially bio-based precursor 1,4-cyclohexanedione. We identified regio- and stereoselective enzymes catalyzing reduction and transamination of the diketone, which can be performed in a one-pot sequential or cascade mode. For this, we identified regioselective keto reductases for the selective mono reduction of the diketone to give 4-hydroxycyclohexanone. The system is modular and by choosing stereocomplementary amine transaminases, both cis- and trans-4-aminocyclohexanol were synthesized with good to excellent diastereomeric ratios. Furthermore, we identified an amine transaminase that produces cis-1,4-cyclohexanediamine with diastereomeric ratios >98 : 2. These examples highlight that the high selectivity of enzymes enable short and stereoselective cascade multifunctionalizations to generate high-value building blocks from renewable starting materials. Introduction.

Ruthenium-Na2CO3-catalyzed one-pot synthesis of ring-hydrogenated carbamates from aromatic amines and organic carbonates under H2

A facile and efficient one-pot procedure for the synthesis of ring hydrogenated carbamates from aromatic amine and alkylene carbonate under H2 gas pressure has been developed using a heterogeneous catalyst system comprising ruthenium and alkali metal carbonates. The effects of temperature, H2 pressure, catalyst (types of loaded metal and their supports), molar ratio of substrate/catalyst, and solvent were also investigated. Among the alkali metal carbonates, the sodium carbonate was found as best promoter for nucleophilic attack and ring-opening (NARO) reaction and thus increased the yield of ring hydrogenated carbamate up to 88% when using Ru/C as ring hydrogenation (RH) catalyst. This catalyst system could be reused at least five times without signi?cant loss of activity, which makes this process cost-effective and eco-friendly.