5-Naphthalen-1-YL-benzo[1,3]dioxole

Base Information

• Chemical Name: 5-Naphthalen-1-YL-benzo[1,3]dioxole
• CAS No.: 594823-69-5
• Molecular Formula: C₁₇H₁₂O₂
• Molecular Weight: 248.281
• DSSTox Substance ID: DTXSID90581590
• Nikkaji Number: J1.761.214J
• Mol file: 594823-69-5.mol

Synonyms:594823-69-5;5-NAPHTHALEN-1-YL-BENZO[1,3]DIOXOLE;5-naphthalen-1-yl-1,3-benzodioxole;5-(Naphthalen-1-yl)benzo[d][1,3]dioxole;SCHEMBL2992287;DTXSID90581590;5-(naphthalen-1-yl)-2H-1,3-benzodioxole

Chemical Property of 5-Naphthalen-1-YL-benzo[1,3]dioxole

Chemical Property:

• Boiling Point: 396.2±42.0 °C(Predicted)
• PSA: 18.46000
• Density: 1.241±0.06 g/cm3(Predicted)
• LogP: 4.23550
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 248.083729621
• Heavy Atom Count: 19
• Complexity: 316

Purity/Quality:

99% ^*data from raw suppliers

5-NAPHTHALEN-1-YL-BENZO[1,3]DIOXOLE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1OC2=C(O1)C=C(C=C2)C3=CC=CC4=CC=CC=C43

Technology Process of 5-Naphthalen-1-YL-benzo[1,3]dioxole

There total 5 articles about 5-Naphthalen-1-YL-benzo[1,3]dioxole 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: 95.0%

5-chloro-1,3-benzodioxole (7228-38-8) + C12H13OS(1-)*Na(1+) → 1-(3,4-methylenedioxyphenyl)naphthalene (594823-69-5)

Guidance literature:

With η³-1-tert-butylindenyl palladium chloride dimer; In toluene; at 70 ℃; for 4h; Inert atmosphere; Glovebox; Sealed tube;

DOI:10.1021/acs.orglett.6b02330

Reference yield: 93.0%

1-Bromonaphthalene (90-11-9) + 12-benzo[1,3]dioxol-5-yl-6-tert-butyl-5,6,7,12-tetrahydro-6-aza-12-bisma-dibenzo[a,d]cyclooctene → 1-(3,4-methylenedioxyphenyl)naphthalene (594823-69-5)

Guidance literature:

With 1-methyl-pyrrolidin-2-one; tetrakis(triphenylphosphine) palladium⁽⁰⁾; at 80 ℃; for 3h;

DOI:10.1002/anie.200250205

Reference yield: 80.0%

N,N,N-trimethyl-1-naphthalenaminium trifluoromethanesulfonate (1351445-39-0) + 3,4-(methylenedioxy)-benzeneboronic acid (94839-07-3) → 1-(3,4-methylenedioxyphenyl)naphthalene (594823-69-5)

Guidance literature:

With SIPr-PdCl₂-Py; cesium fluoride; In tetrahydrofuran; at 80 ℃; for 8h; Schlenk technique; Inert atmosphere;

DOI:10.1016/j.tet.2021.132431

upstream raw materials:

1-Bromonaphthalene

1,3-dihydroisobenzofuran-5-yl trifluoromethanesulfonate

1-naphthylmagnesiumbromide

5-chloro-1,3-benzodioxole

Refernces

• 1、 Melvin, Patrick R.,Hazari, Nilay,Beromi, Megan Mohadjer,Shah, Hemali P.,Williams, Michael J.. "Pd-Catalyzed Suzuki-Miyaura and Hiyama-Denmark Couplings of Aryl Sulfamates". supporting information. p. 5784 - 5787. Retrieved 2016/11/29.
• 2、 Gavryushin, Andrei,Kofink, Christiane,Manolikakes, Georg,Knochel, Paul. "Efficient cross-coupling of functionalized arylzinc halides catalyzed by a nickel chloride-diethyl phosphite system". . p. 4871 - 4874. Retrieved 2007/10/03.