138517-66-5

Basic information

• Product Name: (11S,12S)-9,10-DIHYDRO-9,10-ETHANOANTHRACENE-11,12-DIAMINE
• Synonyms: (11S,12S)-9,10-DIHYDRO-9,10-ETHANOANTHRACENE-11,12-DIAMINE;(S,S)-11,12-Diamino-9,10-dihydro-9,10-ethanoanthracene;(11S,12S)-9,10-Dihydro-9,10-ethanoanthracene-11,12-diamine >=95.0% (HPLC)
• CAS NO: 138517-66-5
• Molecular Formula: C₁₆H₁₆N₂
• Molecular Weight: 236.31164
• Product Categories: Asymmetric Synthesis;Synthetic Organic Chemistry
• Mol File: 138517-66-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 158 °C
• Boiling Point: 396.72°C at 760 mmHg
• Flash Point: 231.6°C
• Appearance: /
• Density: 1.195g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 20 ° (C=1, MeOH)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 9.38±0.40(Predicted)
• BRN: 8693351
• CAS DataBase Reference: (11S,12S)-9,10-DIHYDRO-9,10-ETHANOANTHRACENE-11,12-DIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (11S,12S)-9,10-DIHYDRO-9,10-ETHANOANTHRACENE-11,12-DIAMINE(138517-66-5)
• EPA Substance Registry System: (11S,12S)-9,10-DIHYDRO-9,10-ETHANOANTHRACENE-11,12-DIAMINE(138517-66-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 138517-66-5(Hazardous Substances Data)

Usage

Uses

(11S,12S)-9,10-Dihydro-9,10-ethanoanthracene-11,12-diamine is a chiral diamine, which can be used as a reactant: To synthesize pyridine based C2-symmetrical chiral organocatalysts via palladium catalyzed coupling reaction with 2-bromo-4-(alkylamino)pyridine. To prepare porous organic imine cages by cycloimination reaction with triformylbenzene. To synthesize Ga/Yb-Schiff base complex, which is utilized as a catalyst for the asymmetric synthesis of 5-amino-2-(hydroxyalkyl)oxazoles by enantioselective α-addition of α-isocyano amides to aldehydes.

InChI:InChI=1/C16H16N2/c17-15-13-9-5-1-2-6-10(9)14(16(15)18)12-8-4-3-7-11(12)13/h1-8,13-16H,17-18H2/t13?,14?,15-,16-/m0/s1

Upstream product

• 143668-69-3 C₁₈H₁₂N₂O₂ 
• 120-12-7 anthracene 

Downstream Products

• 1259130-37-4 C₃₀H₂₈N₂O₄ 
• 138517-65-4 (+)-11(S),12(S)-bis-<2'-(diphenylphosphino)benzamido>-9,10-dihydro9,10-ethanoanthracene 

Relevant articles and documents

Total Synthesis of (-)-Bacchopetiolone via an Asymmetric Hydroxylative Phenol Dearomatization/[4+2]-Dimerization Cascade Promoted by a Novel Salen-Type Chiral Iodane

The first total and biomimetic synthesis of the natural bis(sesquiterpene) (-)-bacchopetiolone (revised structure) was completed through a highly diastereoselective hydroxylative phenol dearomatization/[4+2]-dimerization cascade conversion of (+)-curcuphe

A modular approach for ligand design for asymmetric allylic alkylations via enantioselective palladium-catalyzed ionizations

A new class of ligands for asymmetric transition metal catalysis based on 2-(diphenylphosphino)benzoic acid was used in a mechanistically-defined palladium-catalyzed reaction in which enantiodifferentiation was the result of selective ionization of substr