Benzo(a)pyrene diol epoxide

Base Information

• Chemical Name: Benzo(a)pyrene diol epoxide
• CAS No.: 55097-80-8
• Molecular Formula: C20H14O3
• Molecular Weight: 302.32
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID9036779
• Nikkaji Number: J282.916I
• Wikidata: Q26840771
• NCI Thesaurus Code: C196
• Metabolomics Workbench ID: 54193
• ChEMBL ID: CHEMBL1743211
• Mol file: 55097-80-8.mol

Synonyms:7,8-BaP-9,10-Diol Epoxide;7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide;7,8-Dihydroxy-9,10-Epoxy-7,8,9,10-Tetrahydrobenzo(a)pyrene;Anti BaPDE;Anti-BaPDE;Benzo(a)pyrene 7,8-Dihydrodiol 9,10-Epoxide;Benzo(a)pyrene-7,8-diol 9,10-Epoxide;BPDE

Chemical Property of Benzo(a)pyrene diol epoxide

Chemical Property:

• Vapor Pressure: 5.73E-15mmHg at 25°C
• Melting Point: 229.7oC
• Boiling Point: 594.2°C at 760 mmHg
• PKA: 13.50±0.40(Predicted)
• Flash Point: 313.2°C
• PSA: 52.99000
• Density: 1.569
• LogP: 3.43180
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 302.094294304
• Heavy Atom Count: 23
• Complexity: 507

Purity/Quality:

99% ^*data from raw suppliers

7,8,8a,9a-Tetrahydrobenzo[1,12]tetrapheno-[10,11-b]oxirene-7,8-diol 95+% ^*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=CC2=C3C(=C1)C=CC4=C3C(=CC5=C4C6C(O6)C(C5O)O)C=C2

Technology Process of Benzo(a)pyrene diol epoxide

There total 24 articles about Benzo(a)pyrene diol epoxide 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:

C21H13ClO4 → (+/-)-r-7,t-8-Dihydroxy-t-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (63323-30-8,55097-80-8,58917-67-2,58917-91-2,60268-85-1,60268-86-2,63323-29-5,63323-31-9,63357-09-5,64397-28-0,64912-49-8,64912-50-1,82111-22-6,111137-80-5,91327-01-4)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 0 - 20 ℃; for 2h; Yield given;

DOI:10.1021/ja00147a031

Reference yield:

1-bromopyrene (1714-29-0) → (+/-)-r-7,t-8-Dihydroxy-t-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (63323-30-8,55097-80-8,58917-67-2,58917-91-2,60268-85-1,60268-86-2,63323-29-5,63323-31-9,63357-09-5,64397-28-0,64912-49-8,64912-50-1,82111-22-6,111137-80-5,91327-01-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) n-BuLi, 2.) B(OMe)3, 3.) H₂O₂, 4.) t-BuNH₂, 5.) Et₃N

2: n-BuLi / tetrahydrofuran / 5 h / -78 - 20 °C

3: H₂ / PtO₂ / tetrahydrofuran / 4 h / 735.5 Torr / Ambient temperature

4: 1.) BF₃*OEt₂, NaI / 1.) CH₃CN, from 0 deg C to RT, 2 h, 2.) CH₂Cl₂, reflux, 3 h

5: BCl₃ / CH₂Cl₂ / 0.5 h / -20 °C

6: 4 M aq.NaOH / tetrahydrofuran / 2 h / 0 - 20 °C

With sodium hydroxide; n-butyllithium; Trimethyl borate; boron trifluoride diethyl etherate; hydrogen; dihydrogen peroxide; boron trichloride; tert-butylamine; triethylamine; sodium iodide; platinum(IV) oxide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00147a031

Reference yield:

Toluene-4-sulfonic acid 2-bromo-pyren-1-yl ester (172533-57-2) → (+/-)-r-7,t-8-Dihydroxy-t-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (63323-30-8,55097-80-8,58917-67-2,58917-91-2,60268-85-1,60268-86-2,63323-29-5,63323-31-9,63357-09-5,64397-28-0,64912-49-8,64912-50-1,82111-22-6,111137-80-5,91327-01-4)

Guidance literature:

Multi-step reaction with 5 steps

1: n-BuLi / tetrahydrofuran / 5 h / -78 - 20 °C

2: H₂ / PtO₂ / tetrahydrofuran / 4 h / 735.5 Torr / Ambient temperature

3: 1.) BF₃*OEt₂, NaI / 1.) CH₃CN, from 0 deg C to RT, 2 h, 2.) CH₂Cl₂, reflux, 3 h

4: BCl₃ / CH₂Cl₂ / 0.5 h / -20 °C

5: 4 M aq.NaOH / tetrahydrofuran / 2 h / 0 - 20 °C

With sodium hydroxide; n-butyllithium; boron trifluoride diethyl etherate; hydrogen; boron trichloride; sodium iodide; platinum(IV) oxide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00147a031

upstream raw materials:

(-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene

1-bromopyrene

Toluene-4-sulfonic acid 2-bromo-pyren-1-yl ester

(((2-bromo-1,3-phenylene)bis(oxy))bis(methylene))dibenzene

Downstream raw materials:

(S)-2-[((S)-1-{(S)-2-Amino-3-[1-(7,8,9-trihydroxy-7,8,9,10-tetrahydro-benzo[def]chrysen-10-yl)-1H-imidazol-4-yl]-propionyl}-pyrrolidine-2-carbonyl)-amino]-3-(4-hydroxy-phenyl)-propionic acid

(S)-2-[((S)-1-{(S)-2-Amino-3-[3-(7,8,9-trihydroxy-7,8,9,10-tetrahydro-benzo[def]chrysen-10-yl)-3H-imidazol-4-yl]-propionyl}-pyrrolidine-2-carbonyl)-amino]-3-(4-hydroxy-phenyl)-propionic acid

7,8,9,10-tetrahydroxy-7,8,9,10-tetrahydrobenzopyrene

7,8,9,10-tetrahydroxytetrahydrobenzo[a]pyrene

Refernces

• 1、 Koreeda, Masato,Gopalaswamy, Ramesh. "Regio- and stereocontrolled synthesis of the bay-region anti-diol epoxide metabolites of the potent carcinogens benzo[a]pyrene and 7,12-dimethylbenz[a]anthracene". . p. 10595 - 10596. Retrieved 2007/10/02.
• 2、 Yagi,Thakker,Hernandez,Koreeda,Jerina. "Synthesis and reactions of the highly mutagenic 7,8 diol 9,10 epoxides of the carcinogen benzo[a]pyrene". . p. 1604 - 1611. Retrieved 2007/10/11.