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

Base Information

• Chemical Name: (11S,12S)-9,10-Dihydro-9,10-ethanoanthracene-11,12-diamine
• CAS No.: 138517-66-5
• Molecular Formula: C16H16N2
• Molecular Weight: 236.316
• Hs Code.: 2921590090
• European Community (EC) Number: 677-198-6
• DSSTox Substance ID: DTXSID90467628
• Nikkaji Number: J1.492.553H,J2.743.692G
• Wikidata: Q82294667
• Mol file: 138517-66-5.mol

Synonyms:138517-66-5;(11S,12S)-9,10-Dihydro-9,10-ethanoanthracene-11,12-diamine;9,10-Ethanoanthracene-11,12-diamine, 9,10-dihydro-, (11S,12S)-;(15S,16S)-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-15,16-diamine;D3445;SCHEMBL2481267;DTXSID90467628;MFCD09038519;MFCD09038520;AKOS027252925;CS-W010315;AS-71349;T70246;J-007152;(11S,12S)-9,10-Dihydro-9,10-ethanoanthracene-11,12-diamine, AldrichCPR;(11R,12R)-9,10-Dihydro-9,10-ethanoanthracene-11,12-diamine, >=95.0% (HPLC);(15S,16S)-tetracyclo[6.6.2.0(2),?.0?,(1)?]hexadeca-2(7),3,5,9(14),10,12-hexaene-15,16-diamine;(15S,16S)-tetracyclo[6.6.2.0?,?.0?,??]hexadeca-2(7),3,5,9(14),10,12-hexaene-15,16-diamine

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

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 158 °C
• Refractive Index: 20 ° (C=1, MeOH)
• Boiling Point: 396.72°C at 760 mmHg
• PKA: 9.38±0.40(Predicted)
• Flash Point: 231.6°C
• PSA: 52.04000
• Density: 1.195g/cm³
• LogP: 3.33260
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 236.131348519
• Heavy Atom Count: 18
• Complexity: 273

Purity/Quality:

98%,99%, ^*data from raw suppliers

(11S,12S)-9,10-Dihydro-9,10-ethanoanthracene-11,12-diamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C3C(C(C(C2=C1)C4=CC=CC=C34)N)N
• Isomeric SMILES: C1=CC=C2C3[C@@H]([C@H](C(C2=C1)C4=CC=CC=C34)N)N
• 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.

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

There total 9 articles about (11S,12S)-9,10-Dihydro-9,10-ethanoanthracene-11,12-diamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(11S,12S)-11,12-diamino-9,10-dihydro-9,10-ethanoanthracene (R)-mandelate monoammonium salt → (9R,10R,11S,12S)-9,10-dihydro-9,10-ethanoanthracene-11,12-diamine (138517-66-5)

Guidance literature:

With sodium hydroxide; In dichloromethane; water; at 20 - 25 ℃; for 1h; enantioselective reaction;

DOI:10.1021/acs.orglett.6b00224

Reference yield: 59.0%

C18H12N2O2 (143668-69-3) → (S,S)-trans-9,10-dihydro-9,10-ethanoanthracene-11,12-diamine (138517-66-5)

Guidance literature:

With hydrogenchloride; In dichloromethane; at 20 ℃; for 21h;

DOI:10.1016/S0957-4166(00)00331-1

Reference yield:

(11S,12S)-11,12-diamino-9,10-dihydro-9,10-ethanoanthracene (S)-mandelate monoammonium salt → (9R,10R,11S,12S)-9,10-dihydro-9,10-ethanoanthracene-11,12-diamine (138517-66-5)

Guidance literature:

With sodium hydroxide; In dichloromethane; water; at 20 - 25 ℃; for 1h;

DOI:10.1021/acs.orglett.6b00224

upstream raw materials:

anthracene

C₁₈H₁₂N₂O₂

Downstream raw materials:

C₃₀H₂₈N₂O₄