539834-16-7

Basic information

• Product Name: (1S,2S,4S,5S)-2,5-BIS(3,5-DI-TERT-BUTYL-2-HYDROXYBENZYLIDENEAMINO)BICYCLO[2.2.1]HEPTANE
• Synonyms: 2,2'-[(1S,2S,4S,5S)-BICYCLO[2.2.1]HEPTANE-2,5-DIYLBIS(NITRILOMETHYL)]BIS(4,6-DI-TERT-BUTYLPHENOL);(1S,2S,4S,5S)-2,5-BIS(3,5-DI-TERT-BUTYL-2-HYDROXYBENZYLIDENEAMINO)BICYCLO[2.2.1]HEPTANE;2,2'-[(1S,2S,4S,5S)-Bicyclo[2.2.1]heptane-2,5-diylbis(nitrilomethylidyne)]bis[4,6-bis(1,1-dimethylethyl)phenol];2'-[(1S
• CAS NO: 539834-16-7
• Molecular Formula: C37H54N2O2
• Molecular Weight: 558.84
• Product Categories: Asymmetric Synthesis;Synthetic Organic Chemistry
• Mol File: 539834-16-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 254 °C
• Boiling Point: 625.103°C at 760 mmHg
• Flash Point: 429.158°C
• Appearance: /
• Density: 1.058g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.559
• PKA: 13.33±0.40(Predicted)
• CAS DataBase Reference: (1S,2S,4S,5S)-2,5-BIS(3,5-DI-TERT-BUTYL-2-HYDROXYBENZYLIDENEAMINO)BICYCLO[2.2.1]HEPTANE(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,4S,5S)-2,5-BIS(3,5-DI-TERT-BUTYL-2-HYDROXYBENZYLIDENEAMINO)BICYCLO[2.2.1]HEPTANE(539834-16-7)
• EPA Substance Registry System: (1S,2S,4S,5S)-2,5-BIS(3,5-DI-TERT-BUTYL-2-HYDROXYBENZYLIDENEAMINO)BICYCLO[2.2.1]HEPTANE(539834-16-7)

Safety Data

• Hazardous Substances Data: 539834-16-7(Hazardous Substances Data)

Usage

Uses

(1S,2S,4S,5S)-2,5-Bis(3,5-di-tert-butyl-2-hydroxybenzylideneamino)bicyclo[2.2.1]heptane is a ligand used in the preparation of chromium-based catalysts for the asymmetric Nozaki-Hiyama-Kishi addition of aldehydes and allyl and vinyl halides.

InChI:InChI=1/C37H54N2O2/c1-34(2,3)26-14-24(32(40)28(18-26)36(7,8)9)20-38-30-16-23-13-22(30)17-31(23)39-21-25-15-27(35(4,5)6)19-29(33(25)41)37(10,11)12/h14-15,18-23,30-31,40-41H,13,16-17H2,1-12H3/b38-20+,39-21+

Upstream product

• 37942-07-7 3,5-di-tert-butyl-2-hydroxybenzaldehyde 
• 698353-43-4 (1R,2R,4R,5R)-2,5-diaminobicyclo[2.2.1]heptane 
• 135094-36-9 (1R,2S,4R,5S)-exo,exo-bicyclo[2.2.1]heptane-2,5-diol 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 141737-16-8 rac-bicyclo[2.2.1]heptane-2,5-dione dioxime 
• 171065-84-2 2,5-diaminobicyclo[2.2.1]heptane 
• 698353-39-8 (1R,2R,4R,5R)-2,5-bis[(4-methylphenyl)sulfonylamido]bicyclo[2.2.1]heptane 
• 145092-77-9 (1R,4R)-bicyclo[2.2.1]heptane-2,5-dione 
• 698353-42-3 (1S,2S,4S,5S)-2,5-diamino-bicyclo[2.2.1]heptane 
• 5888-36-8 (1S,2R,4S,5R)-2,5-dihydroxybicyclo[2.2.1]heptane 
• 145092-68-8 (S,S)-bicyclo<2.2.1>heptane-2,5-dione 
• 698353-40-1 (1S,2S,4S,5S)-2,5-bis[(4-methylphenyl)sulfonylamido]bicyclo[2.2.1]heptane 
• 698353-37-6 endo,endo-2,5-diaminobicyclo[2.2.1]heptane 

Relevant articles and documents

Enantioselective Synthesis of DIANANE, a Novel C2-Symmetric Chiral Diamine for Asymmetric Catalysis

DIANANE (endo,endo-2,5-diaminonorbornane) is a novel chiral C 2-symmetric diamine, based on the rigid bicyclo[2.2.1]heptane scaffold. Schiff-base ligands derived from DIANANE have already found use in asymmetric catalysis, e.g., in the highly e