cis-1,2-Diaminocyclohexane
Description References- Product Name
- cis-1,2-Diaminocyclohexane
- CAS No.
- 1436-59-5
- Chemical Name
- cis-1,2-Diaminocyclohexane
- Synonyms
- cis<;(2-aminocyclohexyl)amine;cis-1,2-Cyclohexandiamine;CIS-1,2-CYCLOHEXANEDIAMINE;CIS-1,2-DIAMINOCYCLOHEXANE;meso-1,2-Cyclohexanediamine;cis-Cyclohexane-1,2-diamine;1,2-DIAMINOCYCLOHEXANE, cis;1,2-Cyclohexanediamine, cis-;(R)(S)-1,2-Diaminocyclohexane
- CBNumber
- CB9412187
- Molecular Formula
- C6H14N2
- Formula Weight
- 114.19
- MOL File
- 1436-59-5.mol
cis-1,2-Diaminocyclohexane Property
- 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
- 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
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H314Causes severe skin burns and eye damage
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P363Wash contaminated clothing before reuse.
P405Store locked up.
N-Bromosuccinimide Price
- Product number
- C1463
- Product name
- cis-1,2-Cyclohexanediamine
- Purity
- >97.0%(GC)(T)
- Packaging
- 5g
- Price
- $72
- Updated
- 2025/07/31
- Product number
- C1463
- Product name
- cis-1,2-Cyclohexanediamine
- Purity
- >97.0%(GC)(T)
- Packaging
- 25g
- Price
- $210
- Updated
- 2025/07/31
- Product number
- D416224
- Product name
- cis-1,2-Diaminocyclohexane
- Packaging
- 100mg
- Price
- $45
- Updated
- 2021/12/16
- Product number
- D416224
- Product name
- cis-1,2-Diaminocyclohexane
- Packaging
- 500mg
- Price
- $55
- Updated
- 2021/12/16
- Product number
- CHM0014089
- Product name
- CIS-1, 2-DIAMINO CYCLOHEXANE
- Purity
- 95.00%
- Packaging
- 1G
- Price
- $686.54
- Updated
- 2021/12/16
cis-1,2-Diaminocyclohexane Chemical Properties,Usage,Production
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®ion=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
286-18-0
1121-22-8
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
cis-1,2-Diaminocyclohexane Preparation Products And Raw materials
Raw materials
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View Lastest Price from cis-1,2-Diaminocyclohexane manufacturers
- Product
- cis-1,2-Diaminocyclohexane 1436-59-5
- Price
- US $31.00-274.00/g
- Min. Order
- 5g
- Purity
- 0.98
- Supply Ability
- 25kg
- Release date
- 2023-12-11
- Product
- cis-1,2-Diaminocyclohexane 1436-59-5
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-07-11
- Product
- cis-1,2-Diaminocyclohexane 1436-59-5
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-07-09