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(11S,12S)-9,10-Dihydro-9,10-ethanoanthracene-11,12-diamine

(11S,12S)-9,10-Dihydro-9,10-ethanoanthracene-11,12-diamine

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Catalog Number

ACM138517665

Product Name

CAS

138517-66-5

Product Overview
Usage

Synonyms

(S,S)-11,12-Diamino-9,10-dihydro-9,10-ethanoanthracene

IUPAC Name

(15S,16S)-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-15,16-diamine

Molecular Weight

236.31

Molecular Formula

C16H16N2

Canonical SMILES

C1=CC=C2C3C(C(C(C2=C1)C4=CC=CC=C34)N)N

InChI

NWDYSRZJOLDMRE-CKUJCDMFSA-N

InChI Key

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-/m0/s1

Boiling Point

396.72ºC at 760 mmHg

Melting Point

152.5-153.9 °C

Flash Point

231.6ºC

Purity

98%

Density

1.195g/cm³

Appearance

Off-white powder

Complexity

273

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

Exact Mass

236.13100

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Isomeric SMILES

C1=CC=C2C3[C@@H]([C@H](C(C2=C1)C4=CC=CC=C34)N)N

Monoisotopic Mass

236.131g/mol

Topological Polar Surface Area

52A^2

Application

The purpose of (11S,12S)-9,10-Dihydro-9,10-ethanoanthracene-11,12-diamine, a chiral diamine, is to serve as a versatile reactant in various chemical syntheses. It is utilized in the synthesis of pyridine-based C2-symmetrical chiral organocatalysts through a palladium-catalyzed coupling with 2-bromo-4-(alkylamino)pyridine. Additionally, it plays a crucial role in preparing porous organic imine cages via cycloimination with triformylbenzene. Furthermore, this compound is instrumental in forming a Ga/Yb-Schiff base complex, acting as a catalyst for the asymmetric synthesis of 5-amino-2-(hydroxyalkyl)oxazoles, which involves the enantioselective α-addition of α-isocyano amides to aldehydes.

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CAS
Size
Purity
Price
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138517-66-5
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98%
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