Trans ‐ N 1 , N 2 ‐Dimethyl‐1,2‐Cyclohexanediamine

Abstract

(±): [67579-81-1] C8H18N2 (MW 142.1) (R,R): [68737-65-5] C8H18N2 (MW 142.1) (S,S): [87583-89-9] C8H18N2 (MW 142.1) InChI = 1S/C8H18N2/c1-9-7-5-3-4-6-8(7)10-2/h7-10H,3-6H2,1-2H3/t7-,8-/m1/s1 InChIKey = JRHPOFJADXHYBR-HTQZYQBOSA-N (used as a ligand in a variety of metal-catalyzed coupling reactions and as a chiral auxiliary in diastereoselective reactions) Physical data: specific gravity (20/20) 0.91, refractive index 1.47. (R,R): [α]d20 −149 (c 1.55, CH2Cl2).1a Solubility: soluble in common organic solvents. Analysis of Reagent Purity: 1H NMR (400 MHz, CDCl3) δ 2.37 (s, 6H, 2 × NMe), 2.12–2.04 (m, 2H, 2 × NCH), 2.02–1.97 (m, 2H, NCHCH2), 1.75–1.64 (m, 2H, NCHCH2), 1.27–1.13 (m, 2H, CH2), 1.01–0.84 (m, 2H, CH2). Form Supplied in: colorless to light yellow or orange clear liquid. Purification Method: can be purified by vacuum distillation (bp 83 °C/13 mmHg). Preparative Methods: racemic N1,N2-dimethyl-1,2-cyclohexanediamine (1) can be prepared by the methylation of 1,2-cyclohexanediamine.1a,b Enantiomerically pure (R,R)-(2) and (S,S)-N1,N2-dimethyl-1,2-cyclohexanediamine (3) can be prepared in three steps from commercially available racemic 1,2-diaminocyclohexane via kinetic resolution using either (+)- or (–)-tartaric acid (eq 1).1c–e (1) Handling, Storage, and Precautions: hygroscopic liquid; handle under fume hood under nitrogen using proper PPE.