CAS 68737-65-5 (1R,2R)-(-)-N,N'-Dimethylcyclohexane-1,2-diamine

Synonyms

1,2-Cyclohexanediamine, N1,N2-dimethyl-, (1R,2R)-rel-; trans(+/-)-N,N'-Dimethylcyclohexane-1,2-diamine; trans-n,n'-dimethyl-cyclohexane-1, 2-diamine; RP20778; TRANS-N,N'-BISMETHYL-1,2-CYCLOHEXANE DIAMINE; RP20781; 1,2-Cyclohexanediamine,N1,N2-dimethyl-, (1R,2R)-; (1R,2R)-(-)-1,2-Bis(methylamino)cyclohexane; D2946; J-524978;

IUPAC Name

(1R,2R)-1-N,2-N-dimethylcyclohexane-1,2-diamine;

Molecular Weight

142.246g/mol

Molecular Formula

C8H18N2;

Canonical SMILES

CNC1CCCCC1NC;

InChI

InChI=1S/C8H18N2/c1-9-7-5-3-4-6-8(7)10-2/h7-10H,3-6H2,1-2H3/t7-,8-/m1/s1;

InChI Key

JRHPOFJADXHYBR-HTQZYQBOSA-N;

Storage

0-6°C

Complexity

81.3

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

EC Number

614-082-6

Exact Mass

142.147g/mol

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Monoisotopic Mass

142.147g/mol

Rotatable Bond Count

Topological Polar Surface Area

24.1A^2

Application

(1R,2R)-(-)-N,N'-Dimethylcyclohexane-1,2-diamine, a white to light yellow crystalline powder, serves as a versatile compound utilized in various complex chemical syntheses. As a ligand, it facilitates the synthesis of 4H-benzo[f]imidazo[1,4]diazepin-6-one through a multi-component Ullmann coupling reaction. Additionally, it plays a pivotal role in one of the key synthetic stages for crafting tricyclic γ-secretase modulators. Furthermore, this compound is instrumental in the preparation of chiral fluorous diamino-diol proligands, which are essential in forming zirconium metal complexes that function as catalysts in 1-hexene polymerization. Being an N,N'-dimethylated derivative of enantiopure 1,2-diaminocyclohexane, (1R,2R)-(-)-N,N'-Dimethylcyclohexane-1,2-diamine can also be synthesized via the hydrolysis of (R3a,R7a)-1,3-(dimethyl)-2-phenyl-2,3,3a,4,5,6,7,7a-octahydro-1H-1,3,2-benzodiazaphosphole 2-oxide with HCl-methanol.

March 15, 2025

Essential Ligand for Advanced Synthesis

Using (1R,2R)-(-)-N,N'-Dimethylcyclohexane-1,2-diamine from Alfa Chemistry significantly enhanced our research. The product's purity facilitated its role as a ligand in advanced multi-component reactions. Excellent performance in catalyst synthesis too.