202-33-5

Basic information

• Product Name: benz(j)aceanthrylene
• Synonyms: benz(j)aceanthrylene;Benz[j]aceanthrylene (NB: Overall evaluation upgraded from 3 to 2B with supporting mechanistic and other relevant data)
• CAS NO: 202-33-5
• Molecular Formula: C₂₀H₁₂
• Molecular Weight: 252.32
• Product Categories: Aromatics;Mutagenesis Research Chemicals
• Mol File: 202-33-5.mol
• Article Data: 1

Chemical Properties

• Melting Point: 170-171 °C(Solv: hexane (110-54-3))
• Boiling Point: 330.49°C (rough estimate)
• Flash Point: 247.1 °C
• Appearance: /
• Density: 1.1549 (estimate)
• Vapor Pressure: 1.39E-09mmHg at 25°C
• Refractive Index: 1.8390 (estimate)
• CAS DataBase Reference: benz(j)aceanthrylene(CAS DataBase Reference)
• NIST Chemistry Reference: benz(j)aceanthrylene(202-33-5)
• EPA Substance Registry System: benz(j)aceanthrylene(202-33-5)

Safety Data

• Hazardous Substances Data: 202-33-5(Hazardous Substances Data)

Usage

Carcinogenicity

Highly significant carcinogenicity was found in one initiation–promotion study on mouse skin and after intraperitoneal administration to mice. Increases in tumor incidence and/or in the number of tumors per animal were observed in both cases.

InChI:InChI=1/C20H12/c1-2-7-16-13(4-1)8-10-17-18-11-9-14-5-3-6-15(20(14)18)12-19(16)17/h1-12H

Synthetic route

1-Hydroxy-1,2-dihydrobenzaceanthrylene (85319-68-2) → Benzaceanthrylene (202-33-5)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 0.75h; Heating;	62%

1,2-Dihydro-benzo[j]aceanthrylen-2-ol (88262-30-0) → Benzaceanthrylene (202-33-5)

Conditions	Yield
With aluminum oxide In benzene for 0.75h; Heating;

8-Oxo-8,9,10,11-tetrahydrobenzanthracene (5472-20-8) → Benzaceanthrylene (202-33-5)

Conditions

Yield

Multi-step reaction with 6 steps 1: 83 percent / zinc dust, iodine / benzene; diethyl ether / 1.) 15 min, reflux, 2.) 2h, reflux 2: 1.) p-TsOH, 2.) 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) / 1.) benzene, reflux, 2h, 2.) reflux, 4h 3: 88 percent / aq. KOH / methanol / 1 h / Heating 4: 88 percent / anhydrous HF / 15 h / Ambient temperature 5: 95 percent / Sodium borohydride / dimethylformamide / 6 h / Ambient temperature 6: 62 percent / p-TsOH / benzene / 0.75 h / Heating View Scheme

NSC-92828 (13728-56-8) → Benzaceanthrylene (202-33-5)

Conditions

Yield

Multi-step reaction with 7 steps 1: 70 percent / polyphosphoric acid / 3 h / 80 °C 2: 83 percent / zinc dust, iodine / benzene; diethyl ether / 1.) 15 min, reflux, 2.) 2h, reflux 3: 1.) p-TsOH, 2.) 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) / 1.) benzene, reflux, 2h, 2.) reflux, 4h 4: 88 percent / aq. KOH / methanol / 1 h / Heating 5: 88 percent / anhydrous HF / 15 h / Ambient temperature 6: 95 percent / Sodium borohydride / dimethylformamide / 6 h / Ambient temperature 7: 62 percent / p-TsOH / benzene / 0.75 h / Heating View Scheme

7-chloromethylbenz[a]anthracene (6325-54-8) → Benzaceanthrylene (202-33-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: 88 percent / dimethylsulfoxide / 2 h / 70 °C 2: 85 percent / KOH / ethane-1,2-diol; H2O / 24 h / Heating 3: anhydrous HF / 24 h / Ambient temperature 4: NaBH4 / tetrahydrofuran; methanol 5: Al2O3 / benzene / 0.75 h / Heating View Scheme

1-Oxo-1,2-dihydrobenzoaceanthrylene (13728-49-9) → Benzaceanthrylene (202-33-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / Sodium borohydride / dimethylformamide / 6 h / Ambient temperature 2: 62 percent / p-TsOH / benzene / 0.75 h / Heating View Scheme

7-(Cyanomethyl)benzanthracene (63018-69-9) → Benzaceanthrylene (202-33-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: 85 percent / KOH / ethane-1,2-diol; H2O / 24 h / Heating 2: anhydrous HF / 24 h / Ambient temperature 3: NaBH4 / tetrahydrofuran; methanol 4: Al2O3 / benzene / 0.75 h / Heating View Scheme

(7-Benzanthryl)acetic Acid (20316-12-5) → Benzaceanthrylene (202-33-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: anhydrous HF / 24 h / Ambient temperature 2: NaBH4 / tetrahydrofuran; methanol 3: Al2O3 / benzene / 0.75 h / Heating View Scheme

(8-Benzanthryl)acetic Acid (13728-58-0) → Benzaceanthrylene (202-33-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 88 percent / anhydrous HF / 15 h / Ambient temperature 2: 95 percent / Sodium borohydride / dimethylformamide / 6 h / Ambient temperature 3: 62 percent / p-TsOH / benzene / 0.75 h / Heating View Scheme

1H-Benzo[j]aceanthrylen-2-one (85319-69-3) → Benzaceanthrylene (202-33-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH4 / tetrahydrofuran; methanol 2: Al2O3 / benzene / 0.75 h / Heating View Scheme

Ethyl-1,2-benzanthracen-5-acetat (13728-60-4) → Benzaceanthrylene (202-33-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: 88 percent / aq. KOH / methanol / 1 h / Heating 2: 88 percent / anhydrous HF / 15 h / Ambient temperature 3: 95 percent / Sodium borohydride / dimethylformamide / 6 h / Ambient temperature 4: 62 percent / p-TsOH / benzene / 0.75 h / Heating View Scheme

(8-Hydroxy-8,9,10,11-tetrahydro-benzo[a]anthracen-8-yl)-acetic acid ethyl ester (85319-66-0) → Benzaceanthrylene (202-33-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) p-TsOH, 2.) 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) / 1.) benzene, reflux, 2h, 2.) reflux, 4h 2: 88 percent / aq. KOH / methanol / 1 h / Heating 3: 88 percent / anhydrous HF / 15 h / Ambient temperature 4: 95 percent / Sodium borohydride / dimethylformamide / 6 h / Ambient temperature 5: 62 percent / p-TsOH / benzene / 0.75 h / Heating View Scheme

Upstream product

• 85319-66-0 (8-Hydroxy-8,9,10,11-tetrahydro-benzo[a]anthracen-8-yl)-acetic acid ethyl ester 
• 13728-60-4 Ethyl-1,2-benzanthracen-5-acetat 
• 85319-69-3 1H-Benzo[j]aceanthrylen-2-one 
• 13728-58-0 (8-Benzanthryl)acetic Acid 
• 20316-12-5 (7-Benzanthryl)acetic Acid 
• 63018-69-9 7-(Cyanomethyl)benzanthracene 
• 13728-49-9 1-Oxo-1,2-dihydrobenzoaceanthrylene 
• 6325-54-8 7-chloromethylbenz[a]anthracene 
• 13728-56-8 NSC-92828 
• 5472-20-8 8-Oxo-8,9,10,11-tetrahydrobenzanthracene 
• 88262-30-0 1,2-Dihydro-benzo[j]aceanthrylen-2-ol 
• 85319-68-2 1-Hydroxy-1,2-dihydrobenzaceanthrylene 

Relevant articles and documents

Synthesis of a Series of Novel Polycyclic Aromatic Systems: Isomers of Benzanthracene Containing a Cyclopenta-Fused Ring

The four possible isomers of benzanthracene containing a cyclopenta-fused ring have been synthesized and characterized.These systems are of interest for structure-activity studies in bioactivation because of their predicted high level of activity.Formation of fused five-membered rings by intramolecular cyclodehydration, often difficult to accomplish, was found to be smoothly effected in anhydrous HF, provided the reactivity index (Nt) for the appropriate electrophilic addition was favorable.The dihydro polycyclic aromatic alcohols obtained from reduction of the c orresponding keto cyclodehydration products were best dehydrated to the desired PAH by activity grade I neutral alumina in refluxing benzene.This dehydration proceeds in high yield without the formation of isomeric or polymeric side products that occurred even under such mild acid catalysis as p-toluenesulfonic acid.