cis-1,2-Diaminocyclohexane Chemical Properties

Melting point:

8°C

Boiling point:

92-93 °C/18 mmHg (lit.)

Density 

0.952 g/mL at 25 °C (lit.)

vapor pressure 

0.4 mm Hg ( 20 °C)

refractive index 

n20/D 1.493(lit.)

Flash point:

161 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

Water Solubility 

Completely miscible in water

form 

Low Melting Solid

pka

9.93(at 20℃)

color 

Brown

InChI

InChI=1/C6H14N2/c7-5-3-1-2-4-6(5)8/h5-6H,1-4,7-8H2/t5-,6+

InChIKey

SSJXIUAHEKJCMH-OLQVQODUSA-N

SMILES

[C@@H]1(N)CCCC[C@@H]1N |&1:0,6,r|

CAS DataBase Reference

1436-59-5(CAS DataBase Reference)

NIST Chemistry Reference

cis-1,2-Cyclohexanediamine(1436-59-5)

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-36/37/39-45

RIDADR 

UN 2735 8/PG 2

WGK Germany 

3

F 

10-34

HazardClass 

8

PackingGroup 

II

HS Code 

29213000

MSDS

• Language:English Provider:SigmaAldrich

cis-1,2-Diaminocyclohexane Usage And Synthesis

Description

cis-1, 2-Diaminocyclohexane is a cyclohexane derivative. It can be used for the synthesis of platinum complexes with high antitumor activity. It can also be used for the preparation of multidentate ligands for uranyl and transition metal complexation. Moreover, it can also be used as the base for the manufacturing of titanium salalen catalyst. Its derivative also has the potential to be manufactured into a potent factor Xa inhibitor. 

References

Khokhar, Abdul R., et al. "Chemical and Biological Studies on a Series of Novel (trans-(1R,2R)-, trans-(1S,2S)-, and cis-1,2-Diaminocyclohexane)platinum(IV) Carboxylate Complexes." Journal of Medicinal Chemistry 40.1(1997):112.
Mauldin, S. K., et al. "High-performance liquid chromatographic separation of platinum complexes containing the cis-1,2-diaminocyclohexane carrier ligand. " Analytical Biochemistry157.1 (1986):129-43.
Berkessel, A, et al. "Titanium salalen catalysts based on cis-1,2-diaminocyclohexane: enantioselective epoxidation of terminal non-conjugated olefins with H2O2. " Angewandte Chemie 52.32(2013):8467-71.
Yoshikawa, K, et al. "Design, synthesis, and SAR of cis-1,2-diaminocyclohexane derivatives as potent factor Xa inhibitors. Part I: exploration of 5-6 fused rings as alternative S1 moieties. " Bioorganic & Medicinal Chemistry 17.24(2009):8221.
http://www.sigmaaldrich.com/catalog/product/aldrich/307467?lang=en&region=US

Chemical Properties

Clear colorless liquid

Uses

cis-1,2-Diaminocyclohexane was used in the synthesis of platinum complexes that have high antitumor activity.It was also used in the synthesis of multidentate ligands for uranyl and transition metal complexation.

General Description

cis-1,2-Diaminocyclohexane perturbed the spectrum of free pyrroloquinoline quinone (PQQ), a covalently linked form of which is the carbonyl cofactor of lysyl oxidase and also induced similar changes in the spectrum of lysyl oxidase.

Synthesis

General procedure for the synthesis of trans-1,2-cyclohexanediamine from epoxycyclohexane (CAS:286-18-0): 1. Epoxycyclohexane (39.2 g, 0.4 mol) and 30% ammonia (1.0 mol) were added to a reaction flask and stirred at room temperature for 1.5 h until the solution was clarified and the reaction was complete. 2. The reaction mixture was cooled to room temperature under reduced pressure to obtain a white solid. Add 35g of water to dissolve, cool to 0°C, slowly add 50% aqueous sulfuric acid solution, control the temperature not to exceed 30°C. 3. Stir the reaction mixture, reduce pressure and gradually heat to 80°C to remove water, the system gradually viscous curing stop stirring, continue to vacuum for 4 hours. 4. Remove the solid crushed, continue to raise the temperature to 120 ° C vacuum drying 12 hours, Karl Fischer titration showed water content of 0.22%. 5. In another reaction flask, add sodium hydroxide solution, raise the temperature to 40°C, add the above solid powder in batches, and control the temperature not to exceed 50°C. 6. After completion of the addition, raise the temperature to 60°C, stirring until complete clarification, the reaction was completed and the pH was 9-10. 7. Extracted with 1,2-dichloroethane and distilled to obtain aziridine 27.2 g, GC purity 99.6%, two-step yield 70%. 8. 30% ammonia (0.48 mol) and inorganic boric acid (3.5 g, 56 mmol) were added to aziridine (27.2 g, 0.28 mol) and the reaction was heated to 90-95°C overnight. 9. Upon completion of the reaction, trans-1,2-cyclohexanediamine was obtained by distillation under reduced pressure and solidified by cooling to 28.1 g of white solid with 99.7% GC purity and 88% yield, no cis-isomer was detected, and HNMR was in agreement with literature data.

Purification Methods

Dry the diamine over solid KOH and distil it in a vacuum. It is a strong base, keep away from CO2, store in the dark under N2. [Beilstein 13 IV 1.]

References

[1] Bulletin de la Societe Chimique de France, 1956, p. 382,387,1827
[2] Patent: CN106631815, 2017, A. Location in patent: Paragraph 0013; 0014; 0015

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