778761
(11S,12S)-9,10-Dihydro-9,10-ethanoanthracene-11,12-diamine
≥95.0% (HPLC)
Synonym(s):
(S,S)-11,12-Diamino-9,10-dihydro-9,10-ethanoanthracene
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About This Item
Empirical Formula (Hill Notation):
C16H16N2
CAS Number:
Molecular Weight:
236.31
UNSPSC Code:
12352116
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
8693351
InChI
1S/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-/m1/s1
SMILES string
N[C@H]1[C@H](N)[C@H]2c3ccccc3[C@@H]1c4ccccc24
InChI key
NWDYSRZJOLDMRE-QKPAOTATSA-N
assay
≥95.0% (HPLC), 95.0-105.0% (NT)
form
powder
optical purity
enantiomeric excess: ≥98.0%
Application
(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.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Storage Class
13 - Non Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Periphery-functionalized porous organic cages
Reiss PS, et al.
Chemistry?A European Journal , 22(46), 16547-16553 (2016)
A heterobimetallic Ga/Yb-Schiff base complex for catalytic asymmetric α-addition of isocyanides to aldehydes
Mihara H, et al.
Journal of the American Chemical Society, 131(24), 8384-8385 (2009)
A method for the synthesis of pyridine-based C2-symmetrical chiral nucleophilic organocatalysts via Pd-catalyzed coupling
Yaziciouglu EY and Tanyeli C
Tetrahedron Asymmetry, 23(24), 1694-1699 (2012)
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