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778761

Sigma-Aldrich

(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:
138517-66-5
Molecular Weight:
236.31
Beilstein:
8693351
MDL number:
MFCD09038519
UNSPSC Code:
12352116
PubChem Substance ID:
329767993
NACRES:
NA.22

Assay

≥95.0% (HPLC)
95.0-105.0% (NT)

form

powder

optical purity

enantiomeric excess: ≥98.0%

SMILES string

N[C@H]1[C@H](N)[C@H]2c3ccccc3[C@@H]1c4ccccc24

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

InChI key

NWDYSRZJOLDMRE-QKPAOTATSA-N

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 Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

778761-VAR:
778761-250MG:
778761-BULK:
778761-1G:

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Certificates of Analysis (COA)

Lot/Batch Number
BCBD6944V
BCBD6944

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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)
Periphery-functionalized porous organic cages
Reiss PS, et al.
Chemistry?A European Journal , 22(46), 16547-16553 (2016)
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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