(-)-Benzotetramisole - CAS 950194-37-3

(-)-Benzotetramisole is a chiral thiourea catalyst that has emerged as an efficient class of organocatalysts due to their unique dual hydrogen-bonding capacity.

Catalog Number

950194-37-3

CAS

950194-37-3

IUPAC Name

(2S)-2-phenyl-1,2-dihydroimidazo[2,1-b][1,3]benzothiazole

Synonyms

(-)-BTM

Molecular Weight

252.33

Molecular Formula

C15H12N2S

Product Information

Canonical SMILES

C12=N[C@@H](C3=CC=CC=C3)CN1C4=CC=CC=C4S2

InChI

InChI=1S/C15H12N2S/c1-2-6-11(7-3-1)12-10-17-13-8-4-5-9-14(13)18-15(17)16-12/h1-9,12H,10H2/t12-/m1/s1

InChI Key

YGCWPCVAVSIFLO-GFCCVEGCSA-N

Purity

>98.0%(GC)

MDL

MFCD15072149

Storage

Inert atmosphere. Keep cold.

Boiling Point

428.075ºC at 760 mmHg

Density

1.328g/cm3

Reference Reading

1.Origin of enantioselectivity in benzotetramisole-catalyzed dynamic kinetic resolution of azlactones.

Liu P1, Yang X, Birman VB, Houk KN. Org Lett. 2012 Jul 6;14(13):3288-91. doi: 10.1021/ol301243f. Epub 2012 Jun 11.

Density functional theory (DFT) calculations were performed to investigate the origins of enantioselectivity in benzotetramisole (BTM)-catalyzed dynamic kinetic resolution of azlactones. The transition states of the fast-reacting enantiomer are stabilized by electrostatic interactions between the amide carbonyl group and the acetate anion bound to the nucleophile. The chiral BTM catalyst confines the conformation of the α-carbon and the facial selectivity of the nucleophilic attack to promote such electrostatic attractions.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass