(1S,2S)-(+)-1,2-Diaminocyclohexane

Base Information

• Chemical Name: (1S,2S)-(+)-1,2-Diaminocyclohexane
• CAS No.: 21436-03-3
• Molecular Formula: C6H14N2
• Molecular Weight: 114.191
• Hs Code.: 29213000
• European Community (EC) Number: 606-765-2
• UNII: D2V3LYG9F0
• Nikkaji Number: J253.124K
• Wikipedia: Trans-1,2-Diaminocyclohexane
• Wikidata: Q161459
• Mol file: 21436-03-3.mol

Synonyms:1,2-cyclohexanediamine;1,2-cyclohexanediamine, (1R,2R)-;1,2-cyclohexanediamine, (1R-trans)-;1,2-cyclohexanediamine, (1S,2S)-;1,2-cyclohexanediamine, (1S-trans)-;1,2-cyclohexanediamine, (cis)-isomer;1,2-cyclohexanediamine, (trans)-(R)-isomer;1,2-cyclohexanediamine, (trans)-(S)-isomer;1,2-cyclohexanediamine, (trans)-isomer;1,2-DACH;1,2-diaminocyclohexane;1,2-diaminocyclohexane, (+)-;1,2-diaminocyclohexane, (-)-;1,2-diaminocyclohexane, cis-;1,2-diaminocyclohexane, trans-;cyclohexane-1,2-diamine;dach;meso-1,2-diaminocyclohexane;trans-1,2-cyclohexanediamine;trans-1,2-diaminocyclohexane

Chemical Property of (1S,2S)-(+)-1,2-Diaminocyclohexane

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Melting Point: 40-43 °C(lit.)
• Refractive Index: 1.4886
• Boiling Point: 193.6 °C at 760 mmHg
• PKA: 10.76±0.70(Predicted)
• Flash Point: 75 °C
• PSA: 52.04000
• Density: 0.939 g/cm³
• LogP: 1.61560
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Water Solubility.: soluble
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 114.115698455
• Heavy Atom Count: 8
• Complexity: 62.9

Purity/Quality:

99% ^*data from raw suppliers

(1S,2S)-(+)-1,2-Diaminocyclohexane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Cyclic
• Canonical SMILES: C1CCC(C(C1)N)N
• Isomeric SMILES: C1CC[C@@H]([C@H](C1)N)N
• Uses: suzuki reaction For synthesis of optically active products Versatile ligand for the formation of metal complexes. Used in the synthesis of chiral tropocoronands which have potential utility in asymmetric catalysis.

Technology Process of (1S,2S)-(+)-1,2-Diaminocyclohexane

There total 42 articles about (1S,2S)-(+)-1,2-Diaminocyclohexane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

N-benzyl-N-(2-nitro-cyclohexyl)-hydroxylamine → trans-1,2-Diaminocyclohexane (1121-22-8,1436-59-5,20439-47-8,21436-03-3,41013-43-8,694-83-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1016/S0040-4039(01)01746-4

Reference yield: 48.0%

trans-1,2-Diaminocyclohexane (1121-22-8,1436-59-5,20439-47-8,21436-03-3,41013-43-8,694-83-7) + malonic acid dimethyl ester (108-59-8) → (1R,2R)-1,2-diaminocyclohexane (20439-47-8) + (S,S)-1,2-diaminocyclohexane (21436-03-3) + N-[(1R,2R)-2-(2-Methoxycarbonyl-acetylamino)-cyclohexyl]-malonamic acid methyl ester (186144-56-9) + N-((1R,2R)-2-Amino-cyclohexyl)-malonamic acid methyl ester

Guidance literature:

With Candida antarctica lipase on acrylic resin; In 1,4-dioxane; at 20 ℃;

DOI:10.1021/ol0516216

Reference yield:

trans-1,2-Diaminocyclohexane (1121-22-8,1436-59-5,20439-47-8,21436-03-3,41013-43-8,694-83-7) → (1R,2R)-1,2-diaminocyclohexane (20439-47-8) + (S,S)-1,2-diaminocyclohexane (21436-03-3)

Guidance literature:

trans-1,2-Diaminocyclohexane; With L-Tartaric acid; acetic acid; In methanol; water; for 24h; Heating;

With hydrogenchloride; In acetone; for 25h; Heating;

With sodium hydroxide;

DOI:10.1016/S0957-4166(03)00586-X

upstream raw materials:

trans-1,2-Diaminocyclohexane

rac-diaminocyclohexane

malonic acid dimethyl ester

((1S,2S)-2-Azido-cyclohexyl)-((R)-1-phenyl-ethyl)-amine

Downstream raw materials:

(1R,2R)-1,2-diaminocyclohexane

trans-1,2-Cyclohexanediaminetetraacetic acid

trans-N,N,N′,N′-tetramethylcyclohexane-1,2-diamine

(R)-trans-N,N'-dipyridoxylidene-1,2-cyclohexanediamine

Refernces

• 1、 Seidl, Vera,Sternberg, Michelle,Heinemann, Frank W.,Schmiele, Martin,Unruh, Tobias,Wasserscheid, Peter,Meyer, Karsten. "Thermochemical and Structural Studies of New Chiral and Achiral Long Alkyl Chain Functionalized Imidazolinium Ionic Liquids". . p. 6276 - 6288. Retrieved 2021/10/20.
• 2、 Hashemi, Majid,Hadjmohammadi, Mohammad Reza. "Using enantioselective dispersive liquid–liquid microextraction for the microseparation of trans-cyclohexane-1,2-diamine enantiomers". . p. 454 - 459. Retrieved 2017/03/23.