Dibenzo(A,I)pyrene

Base Information

• Chemical Name: Dibenzo(A,I)pyrene
• CAS No.: 189-55-9
• Molecular Formula: C24H14
• Molecular Weight: 302.375
• Hs Code.: 2902909090
• European Community (EC) Number: 205-877-5
• NSC Number: 87521
• UN Number: 3077
• UNII: 7FMI112D18
• DSSTox Substance ID: DTXSID9059751
• Nikkaji Number: J2.970J
• Wikidata: Q26841007
• NCI Thesaurus Code: C44371
• Mol file: 189-55-9.mol

Synonyms:3,4-9,10-dibenzopyrene;benzo(rst)pentaphene;dibenzo(a,i)pyrene

Chemical Property of Dibenzo(A,I)pyrene

Chemical Property:

• Vapor Pressure: 1.12E-11mmHg at 25°C
• Melting Point: 281.5°C
• Refractive Index: 1.912
• Boiling Point: 552.3 °C at 760 mmHg
• Flash Point: 282 °C
• PSA: 0.00000
• Density: 1.313 g/cm³
• LogP: 6.89040
• Storage Temp.: 2-8°C
• XLogP3: 7.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 302.109550447
• Heavy Atom Count: 24
• Complexity: 436
• Transport DOT Label: Class 9

Purity/Quality:

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

Dibenzo[a,i]pyrene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Polycyclic Aromatic Hydrocarbons
• Canonical SMILES: C1=CC=C2C3=C4C(=CC2=C1)C=CC5=CC6=CC=CC=C6C(=C54)C=C3
• Uses: Dibenzo[a,i]pyrene is a polycyclic aromatic hydrocarbon (PAH) with potent carcinogenic activity. Dibenzo[a,i]pyrene was shown to induce DNA adduction, tumorigenicity as well as Ki-ras oncogene mutations in strain A/J mouse lung. Dibenzo[a,i]pyrene has been shown to be present in cigarette smoke condensate and in automobile exhaust gas in small quantities.

Technology Process of Dibenzo(A,I)pyrene

There total 14 articles about Dibenzo(A,I)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: 85.0%

1,2,6,7-tetrahydro-3,4:9,10-dibenzopyrene (89382-27-4) → dibenzo[a,i]pyrene (189-55-9)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene; for 4h; Heating;

DOI:10.1021/jo970181w

Reference yield: 43.0%

2,2'-(naphthalene-1,4-diyl)dibenzaldehyde (285571-20-2) → dibenzo[a,i]pyrene (189-55-9)

Guidance literature:

With trifluorormethanesulfonic acid; trimethyleneglycol; In 1,2-dichloro-ethane; Heating;

DOI:10.1021/jo9918044

Reference yield:

benzopentaphene-5,8-dione (3302-52-1) → dibenzo[a,i]pyrene (189-55-9)

Guidance literature:

With sodium chloride; zinc(II) chloride; zinc; at 210 - 280 ℃;

upstream raw materials:

benzopentaphene-5,8-dione

2,13-dithia<3.3>(1,3)naphthalenophanee

C₂₄H₂₈O₂

anti-<2,2>-cisoid-(1,3)-naphathalenophane-1,11-diene

Downstream raw materials:

5,8-diacetoxy-benzo[rst]pentaphene

5-Formyl-8-methyl-3,4:9,10-dibenzo-pyren

5-Methyl-3,4,9,10-dibenzpyren

benzo[rst]pentaphene-5-carbaldehyde

Refernces

• 1、 Uenseren,E.,Fieser,L.F.. "-". . p. 1386 - 1389. Retrieved 1962.
• 2、 Zhang, Fang-Jie,Cortez, Cecilia,Harvey, Ronald G.. "New synthetic approaches to polycyclic aromatic hydrocarbons and their carcinogenic oxidized metabolites: Derivatives of benzo[s]picene, benzo[rst]pentaphene, and dibenzo[b,def]chrysene". . p. 3952 - 3960. Retrieved 2007/10/03.
• 3、 Harvey, Ronald G.,Pataki, John,Cortez, Cecilia,Raddo, Pasquale Di,Yang, ChengXi. "A New General Synthesis of Polycyclic Aromatic Compounds Based on Enamine Chemistry". . p. 1210 - 1217. Retrieved 2007/10/02.