Dibenz(a,j)acridine-3,4-diol, 3,4-dihydro-, trans-

Base Information

• Chemical Name: Dibenz(a,j)acridine-3,4-diol, 3,4-dihydro-, trans-
• CAS No.: 105467-65-0
• Molecular Formula: C₂₁H₁₅NO₂
• Molecular Weight: 313.356
• Hs Code.: 2933990090
• UNII: Z4B6F08KXO
• DSSTox Substance ID: DTXSID10909550,DTXSID301030192
• Nikkaji Number: J346.636A
• Wikidata: Q27896570
• Mol file: 105467-65-0.mol

Synonyms:105467-65-0;Dibenz(a,j)acridine-3,4-diol, 3,4-dihydro-, trans-;Z4B6F08KXO;117066-30-5;trans-3,4-Dihydroxy-3,4-dihydrodibenz(a,j)acridine;3,4-Dihydrodibenz(a,j)acridine-3,4-diol, trans-(+/-)-;(7S,8S)-13-azapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1,3(12),4(9),5,10,13,15,17,19,21-decaene-7,8-diol;CCRIS 3290;trans-Dibenz(a,j)acridine-3,4-dihydrodiol;trans-3,4-Dihydro-dibenz(a,j)acridine-3,4-diol;trans-3,4-Dihydro-3,4-dihydroxydibenz(a,j)acridine;3,4-dihydrodibenzo[a,j]acridine-3,4-diol;UNII-Z4B6F08KXO;117019-81-5;NIOSH/HN1854000;NIOSH/HN1857000;DTXSID10909550;trans-(+-)-3,4-Dihydroxy-3,4-dihydrodibenz(a,j)acridine;Dibenz(a,j)acridine-3,4-diol, 3,4-dihydro-, (3S-trans)-;DTXSID301030192;HN18540000;HN18570000;(E)-(+-)-3,4-Dihydrodibenz(a,j)acridine-3,4-diol;Q27896570;trans-(+/-)-3,4-dihydrodibenz(a,j)acridine-3,4-diol;(+-)-trans-3,4-Dihydroxy-3,4-dihydrodibenz(a,j)acridine;Dibenz(a,j)acridine-3,4-diol, 3,4-dihydro-, (E)-(+-)-;Dibenz(a,j)acridine-3,4-diol, 3,4-dihydro-, trans-(+-)-;TRANS-(+/-)-3,4-DIHYDROXY-3,4-DIHYDRODIBENZ[A,J]ACRIDINE;TRANS-3,4-DIHYDRODIBENZ(A,J)ACRIDINE-3,4-DIOL, (+/-)-;DIBENZ(A,J)ACRIDINE-3,4-DIOL, 3,4-DIHYDRO-, (3R,4R)-REL-

Chemical Property of Dibenz(a,j)acridine-3,4-diol, 3,4-dihydro-, trans-

Chemical Property:

• Vapor Pressure: 4.41E-16mmHg at 25°C
• Melting Point: 287-293 °C (decomp)(Solv: ethyl acetate (141-78-6))
• Boiling Point: 617°Cat760mmHg
• PKA: 12.95±0.40(Predicted)
• Flash Point: 326.9°C
• PSA: 53.35000
• Density: 1.43g/cm³
• LogP: 3.96230
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 313.110278721
• Heavy Atom Count: 24
• Complexity: 506

Purity/Quality:

DIBENZ(A,J)ACRIDINE-3,4-DIOL, 3,4-DIHYDRO-, TRANS- 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC3=NC4=C(C=C32)C5=C(C=C4)C(C(C=C5)O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C=CC3=NC4=C(C=C32)C5=C(C=C4)[C@@H]([C@H](C=C5)O)O

Technology Process of Dibenz(a,j)acridine-3,4-diol, 3,4-dihydro-, trans-

There total 12 articles about Dibenz(a,j)acridine-3,4-diol, 3,4-dihydro-, trans- 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: 76.0%

trans-3,4-diacetoxy-3,4-dihydrodibenzacridine (106589-54-2,117141-82-9) → trans-3,4-dihydro-3,4-dihydroxydibenzacridine (105467-65-0,117066-30-5)

Guidance literature:

With ammonia; In tetrahydrofuran; methanol; for 1.5h;

DOI:10.1021/jo00382a017

Reference yield:

1-dimethylaminomethyl-naphthalen-2-ol (5419-02-3) → trans-3,4-dihydro-3,4-dihydroxydibenzacridine (105467-65-0,117066-30-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 0.5 g / 0.5 h / 260 - 280 °C

2: 83 percent / 10percent Pd/C / various solvent(s) / 8 h / 190 °C

3: 1.) Na, NH₃ liq., 2.) AcOH / 1.) THF, 18 h, 2.) 100 deg C to 125 deg C, 18 h

4: 1.) t-BuONa, 2.) DDQ / 1.) t-BuOH, reflux, 15 h, 2.) dioxane, reflux, 15 h

5: 29 mg / I₂ / benzene / 12 h / Heating

6: 5percent aq. NaOH / tetrahydrofuran; methanol / 8 h / Ambient temperature

7: pyridine

8: 1.) AIBN, dibromantin, 2.) Li₂CO₃, LiF / 1.) CCl₄, reflux, 30 min, 2.) HMPA, 100 deg C, 3 h

9: 76 percent / NH₃ / methanol; tetrahydrofuran / 1.5 h

With pyridine; sodium hydroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 2,2'-azobis(isobutyronitrile); ammonia; iodine; sodium; lithium carbonate; acetic acid; lithium fluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium t-butanolate; palladium on activated charcoal; In tetrahydrofuran; methanol; benzene;

DOI:10.1021/jo00382a017

Reference yield:

6-amino-1,2,3,4-tetrahydronaphthalene (2217-43-8) → trans-3,4-dihydro-3,4-dihydroxydibenzacridine (105467-65-0,117066-30-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 0.5 g / 0.5 h / 260 - 280 °C

2: 83 percent / 10percent Pd/C / various solvent(s) / 8 h / 190 °C

3: 1.) Na, NH₃ liq., 2.) AcOH / 1.) THF, 18 h, 2.) 100 deg C to 125 deg C, 18 h

4: 1.) t-BuONa, 2.) DDQ / 1.) t-BuOH, reflux, 15 h, 2.) dioxane, reflux, 15 h

5: 29 mg / I₂ / benzene / 12 h / Heating

6: 5percent aq. NaOH / tetrahydrofuran; methanol / 8 h / Ambient temperature

7: pyridine

8: 1.) AIBN, dibromantin, 2.) Li₂CO₃, LiF / 1.) CCl₄, reflux, 30 min, 2.) HMPA, 100 deg C, 3 h

9: 76 percent / NH₃ / methanol; tetrahydrofuran / 1.5 h

With pyridine; sodium hydroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 2,2'-azobis(isobutyronitrile); ammonia; iodine; sodium; lithium carbonate; acetic acid; lithium fluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium t-butanolate; palladium on activated charcoal; In tetrahydrofuran; methanol; benzene;

DOI:10.1021/jo00382a017

upstream raw materials:

trans-3,4-diacetoxy-3,4-dihydrodibenzacridine

1-dimethylaminomethyl-naphthalen-2-ol

dibenz[a,j]acridine

6-amino-1,2,3,4-tetrahydronaphthalene

Downstream raw materials:

trans-3,4-dihydroxy-1,2,3,4-tetrahydrodibenzacridine

trans-3,4-dihydroxy-anti-1,2-epoxy-1,2,3,4-tetrahydrodibenz[a,j]acridine