2-Chloro-2-methylpropanalN-Isopropylimine

Abstract

(R = i-Pr, R1 = R2 = Me, X = Cl) [63364-30-7] C7H14ClN (MW 147.64) InChI = 1S/C7H14ClN/c1-6(2)9-5-7(3,4)8/h5-6H,1-4H3 InChIKey = CTSTWNAEHYFLIY-UHFFFAOYSA-N (R = i-Pr, R1 = R2 = Me, X = Br) [30453-45-3] C7H14BrN (MW 192.12) InChI = 1S/C7H14BrN/c1-6(2)9-5-7(3,4)8/h5-6H,1-4H3 InChIKey = AAYTVJVNTIMIFH-UHFFFAOYSA-N (R = tert-Bu, R1 = R2 = Me, X = Cl) [56990-50-2] C8H16ClN (MW 161.67) InChI = 1S/C8H16ClN/c1-7(2,3)10-6-8(4,5)9/h6H,1-5H3 InChIKey = RERIQGHTEXIRON-UHFFFAOYSA-N (R = Cy, R1 = R2 = Me, X = Cl) [63364-31-8] C10H18ClN (MW 187.70) InChI = 1S/C10H18ClN/c1-10(2,11)8-12-9-6-4-3-5-7-9/h8-9H,3-7H2,1-2H3 InChIKey = SZAAPJXIDZNSPP-UHFFFAOYSA-N (R = Bn, R1 = R2 = Me, X = Cl) [63547-67-1] C11H14ClN (MW 195.68) InChI = 1S/C11H14ClN/c1-11(2,12)9-13-8-10-6-4-3-5-7-10/h3-7,9H,8H2,1-2H3 InChIKey = WBBUWSIIKAPEIW-UHFFFAOYSA-N (R = tert-Bu, R1 = Et, R2 = Me, X = Cl) [63364-32-9] C9H18ClN (MW 175.69) InChI = 1S/C9H18ClN/c1-6-9(5,10)7-11-8(2,3)4/h7H,6H2,1-5H3 InChIKey = WCNFZGSLHIDPSV-UHFFFAOYSA-N (R = tert-Bu, R1 = R2 = Et, X = Cl) [63364-33-0] C10H20ClN (MW 189.72) InChI = 1S/C10H20ClN/c1-6-10(11,7-2)8-12-9(3,4)5/h8H,6-7H2,1-5H3 InChIKey = SVAXRTBSABCFTM-UHFFFAOYSA-N (R = Cy, R1 = R2 = Et, X = Cl) [63364-34-1] C12H22ClN (MW 215.76) InChI = 1S/C12H22ClN/c1-3-12(13,4-2)10-14-11-8-6-5-7-9-11/h10-11H,3-9H2,1-2H3 InChIKey = TZYYYEKHNJULFO-UHFFFAOYSA-N (R = tert-Bu, R1R2 = (CH2)5, X = Cl) [63364-35-2] C11H20ClN (MW 201.73) InChI = 1S/C11H20ClN/c1-10(2,3)13-9-11(12)7-5-4-6-8-11/h9H,4-8H2,1-3H3 InChIKey = KDSZTWMGBIHNCY-UHFFFAOYSA-N (R = Cy, R1R2 = (CH2)5, X = Cl) [63364-36-3] C13H22ClN (MW 227.77) InChI = 1S/C13H22ClN/c14-13(9-5-2-6-10-13)11-15-12-7-3-1-4-8-12/h11-12H,1-10H2 InChIKey = LYGCYROOGGYSDA-UHFFFAOYSA-N (R = tert-Bu, R1 = Me, R2 = Ph, X = Cl) [63364-37-4] C13H18ClN (MW 223.73) InChI = 1S/C13H18ClN/c1-12(2,3)15-10-13(4,14)11-8-6-5-7-9-11/h5-10H,1-4H3 InChIKey = VTPOYALUTYOMFW-UHFFFAOYSA-N (synthesis of 1-aza-1,3-dienes,2 α-amino acetals,2, 3 allylic amines,4 α,β-unsaturated aldehydes,5 α-alkoxy aldimines,6, 7 α-tert-butyl aldimines,7 α-sulfenylated aldimines,8 1,4-diimines,9 α-cyano enamines,10 β-chloro amines,11 aromatic ketones,12 aziridines,13 2-imidazolidinethiones,14 2-imidazolidinones,15 α-aryl aldehydes,16 2-aza-1,3-dienes;17, 18 reductive dechlorination of α-halo aldehydes18) Alternate Name: N-isopropyl-α-chloroisobutyraldimine. Physical Data: 2-chloro-2-methylpropanal N-isopropylimine (R = i-Pr, R1 = R2 = Me, X = Cl): bp 47–49 °C/24 mmHg; 2-bromo-2-methylpropanal N-isopropylimine (R = i-Pr, R1 = R2 = Me, X = Br): bp 58–61 °C/14 mmHg; 2-chloro-2-methylpropanal N-tert-butylimine (R = tert-Bu, R1 = R2 = Me, X = Cl): bp 50–52°/30 mmHg. Solubility: sol most organic solvents; not compatible with aqueous acidic solutions; basic aqueous solutions cause a slow hydrolysis. Form Supplied in: 2-chloro-2-methylpropanal N-isopropyl- and N-tert-butylimines are commercially available as colorless liquids. Analysis of Reagent Purity: GC, 1H NMR. Preparative Methods: aldimines, which are easily accessible from aldehydes and primary amines and which may be prepared in situ, react smoothly with N‐Chlorosuccinimide in CCl4 at room temperature to give α-chloro aldimines (eq 1).2 Similarly, α-bromo7 and the labile α-iodo aldimines19 are accessible by reaction of aldimines with N‐Bromosuccinimide and N‐Iodosuccinimide, respectively (eq 2). Alternatively, the condensation of α-chloro and α-bromo aldehydes with primary amines in the presence of magnesium sulfate,18 Titanium(IV) Chloride,20 or Molecular Sieves28 as dehydrating agent affords the corresponding α-halo aldimines (eq 3). (1) (2) (3) Handling, Storage, and Precautions: α-chloro aldimines are relatively stable bifunctional reagents which are preferably kept in the refrigerator, well-protected from moisture. α-Bromo aldimines are more labile and only readily accessible with N-tert-butyl substituents. α-Iodo aldimines are best freshly prepared and used immediately. The use of α-halo imines in the presence of water is incompatible (except for a fast cyanation reaction; see below). Use in a fume hood.