Benz[c]acridine

Base Information

• Chemical Name: Benz[c]acridine
• CAS No.: 225-51-4
• Molecular Formula: C17H11 N
• Molecular Weight: 229.281
• Hs Code.: 2933990090
• European Community (EC) Number: 205-930-2
• NSC Number: 89261
• UN Number: 3077
• UNII: BV4376Y90X
• DSSTox Substance ID: DTXSID9059759
• Nikkaji Number: J38.206J
• Wikidata: Q26840914
• ChEMBL ID: CHEMBL1724662
• Mol file: 225-51-4.mol

Synonyms:3,4-benzacridine;benz(c)acridine

Chemical Property of Benz[c]acridine

Chemical Property:

• Melting Point: 132°C
• Refractive Index: 1.5515 (estimate)
• Boiling Point: 446.2°Cat760mmHg
• PKA: 4.25±0.30(Predicted)
• Flash Point: 201.4°C
• PSA: 12.89000
• Density: 1.239g/cm³
• LogP: 4.54120
• Storage Temp.: 2-8°C
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 229.089149355
• Heavy Atom Count: 18
• Complexity: 300
• Transport DOT Label: Class 9

Purity/Quality:

99% ^*data from raw suppliers

Benz[c]acridine BCR ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Polycyclic Aromatic Hydrocarbons
• Canonical SMILES: C1=CC=C2C(=C1)C=CC3=CC4=CC=CC=C4N=C32
• Uses: Benzo(c)acridine is used for assays to detect receptor modulating potential in cells.

Technology Process of Benz[c]acridine

There total 39 articles about Benz[c]acridine 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: 98.0%

1-amino-naphthalene (134-32-7) + ortho-bromobenzaldehyde (6630-33-7) → benz[c]acridine (225-51-4,208851-55-2)

Guidance literature:

1-amino-naphthalene; With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium carbonate; In toluene; at 20 ℃; for 0.0833333h; Inert atmosphere;

ortho-bromobenzaldehyde; In toluene; at 80 ℃; for 12h; Inert atmosphere;

With aluminum (III) chloride; In toluene; at 80 ℃; for 12h;

DOI:10.1039/c5ob00755k

Reference yield: 97.0%

2-(naphthalen-1-ylamino)benzaldehyde → benz[c]acridine (225-51-4,208851-55-2)

Guidance literature:

With trifluoroacetic acid; at 80 ℃; for 12h; Inert atmosphere;

DOI:10.1021/jacs.8b11466

Reference yield: 95.0%

1-(benzo[c]acridin-12(7H)-yl)ethan-1-one → benz[c]acridine (225-51-4,208851-55-2)

Guidance literature:

With ammonium cerium (IV) nitrate; In acetone; at 40 ℃; for 5h; Inert atmosphere;

DOI:10.1021/acs.orglett.0c01775

upstream raw materials:

8,9,10,11-tetrahydrobenzoacridine

7,12-dihydro-benzo[c]acridine

1,2-dihydrobenzo[c]acridine

N-benzylidenenaphthalen-1-amine

Downstream raw materials:

7-benzyl-benz[c]acridine

(+/-)-Benzacridine 5,6-Oxide

7-benzyl-7,12-dihydro-benz[c]acridine

(+/-)-3α,4β-Dihydroxy-1β,2β-epoxy-1,2,3,4-tetrahydrobenzacridine

Refernces

• 1、 Li, Jie,Tan, Eric,Keller, Niklas,Chen, Yi-Hung,Zehetmaier, Peter M.,Jakowetz, Andreas C.,Bein, Thomas,Knochel, Paul. "Cobalt-Catalyzed Electrophilic Aminations with Anthranils: An Expedient Route to Condensed Quinolines". . p. 98 - 103. Retrieved 2019/01/08.
• 2、 -. "Nitrogen anthracene class compound and its synthetic method and application (by machine translation)". Paragraph 0107-0110. . Retrieved 2018/05/16.