Dibenzo[a,l]pyrene

Base Information

• Chemical Name: Dibenzo[a,l]pyrene
• CAS No.: 191-30-0
• Molecular Formula: C24H14
• Molecular Weight: 302.375
• Hs Code.: 2902909090
• European Community (EC) Number: 205-886-4
• NSC Number: 90324
• UN Number: 2811
• UNII: G3X629VE4A
• DSSTox Substance ID: DTXSID9059753
• Nikkaji Number: J5.879C
• Wikidata: Q26840756
• NCI Thesaurus Code: C1069
• Metabolomics Workbench ID: 55220
• Mol file: 191-30-0.mol

Synonyms:1,2,3,4-dibenzopyrene;1,2,9,10-dibenzopyrene;4,5,6,7-dibenzpyrene;Ba 51-090462;dibenzo(a,l)pyrene;dibenzo(def,p)chrysene

Chemical Property of Dibenzo[a,l]pyrene

Chemical Property:

• Vapor Pressure: 3.99E-15mmHg at 25°C
• Melting Point: 228.05°C
• Refractive Index: 1.9130 (estimate)
• Boiling Point: 630.6°C at 760 mmHg
• Flash Point: 349.8°C
• PSA: 0.00000
• Density: 1.28g/cm³
• LogP: 6.89040
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Very Slightly, Heated), Dichloromethane (Slightly, Heated)
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 302.109550447
• Heavy Atom Count: 24
• Complexity: 480
• Transport DOT Label: Poison

Purity/Quality:

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

Dibenzo[def,p]chrysene ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,T
• Statements: 40-67-36/37/38-45-41-52/53
• Safety Statements: 23-24/25-36/37-45-26-53-39-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Polycyclic Aromatic Hydrocarbons
• Canonical SMILES: C1=CC=C2C(=C1)C=C3C=CC4=C5C3=C2C6=CC=CC=C6C5=CC=C4
• Uses: An active metabolite from inhalation and dermal exposure to polycyclic aromatics hydrocarbons in hot mix asphalt paving workers. DBC is the most potent tumorigen that has been identified to date. Dib enzo[def,p]chrysene (DBC) is a carcinogen and should be handled with appropriate caution.

Technology Process of Dibenzo[a,l]pyrene

There total 13 articles about Dibenzo[a,l]pyrene 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: 88.0%

N-[2-(5,6-dihydro-4H-benz[de]anthracen-7-yl)benzylidene]aniline → Dibenzo[a,l]pyrene (191-30-0)

Guidance literature:

N-[2-(5,6-dihydro-4H-benz[de]anthracen-7-yl)benzylidene]aniline; With potassium hydroxide; In N,N-dimethyl-formamide; at 100 ℃; for 1h;

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene; for 0.5h; Heating;

DOI:10.1021/jo0303822

Reference yield: 75.0%

9-(2-methoxy-vinyl)-benzo[g]chrysene (1013933-57-7) → Dibenzo[a,l]pyrene (191-30-0)

Guidance literature:

With methanesulfonic acid; In dichloromethane; at 20 ℃; for 2.5h;

DOI:10.1021/ol7029323

Reference yield:

1,10-trimethylenephenanthrene (4389-09-7) → Dibenzo[a,l]pyrene (191-30-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 86 percent / Br₂ / CCl₄ / 2 h / Heating

2.1: 61 percent / CsF / Pd(PPh₃)4 / dimethylformamide / 24 h

3.1: 96 percent / molecular sieves 4 Angstroem / CH₂Cl₂ / 4 h

4.1: KOH / dimethylformamide / 1 h / 100 °C

4.2: 88 percent / DDQ / benzene / 0.5 h / Heating

With potassium hydroxide; 4 A molecular sieve; bromine; cesium fluoride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; 2.1: Suzuki coupling;

DOI:10.1021/jo0303822

upstream raw materials:

Pentahelicen-3-carbonsaeure-methylester

benz[a]anthracene

benzene

1-Phenylbenzanthracen

Downstream raw materials:

10-Formyl-dibenzopyren

Refernces

• 1、 Vingiello,F.A.,Zajac,W.W.. "-". . p. 2228 - 2230. Retrieved 1961.
• 2、 Xu, Daiwang,Duan, Yazhen,Blair, Ian A.,Penning, Trevor M.,Harvey, Ronald G.. "Synthesis of dibenzo[def,p]chrysene, its active metabolites, and their 13C-labeled analogues". supporting information; experimental part. p. 1059 - 1062. Retrieved 2009/04/06.
• 3、 Masuda,Kagawa. "A novel synthesis and carcinogenicity of Dibenzo(a,l)pyrene.". . p. 2736 - 2737. Retrieved 2007/10/06.