2-Bromo-5-(naphthalen-1-yl)thiophene

Base Information

• Chemical Name: 2-Bromo-5-(naphthalen-1-yl)thiophene
• CAS No.: 148875-82-5
• Molecular Formula: C14H9 Br S
• Molecular Weight: 289.195
• DSSTox Substance ID: DTXSID80698489
• Nikkaji Number: J2.245.767E
• Wikidata: Q82628722
• Mol file: 148875-82-5.mol

Synonyms:148875-82-5;2-BROMO-5-NAPHTHALEN-1-YL-THIOPHENE;2-bromo-5-(naphthalen-1-yl)thiophene;2-bromo-5-naphthalen-1-ylthiophene;2-Bromo-5-(1-naphthyl)thiophene;DTXSID80698489

Chemical Property of 2-Bromo-5-(naphthalen-1-yl)thiophene

Chemical Property:

• Boiling Point: 363.4±27.0 °C(Predicted)
• PSA: 28.24000
• Density: 1.486±0.06 g/cm3(Predicted)
• LogP: 5.33080
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 287.96083
• Heavy Atom Count: 16
• Complexity: 243

Purity/Quality:

98%min ^*data from raw suppliers

2-BROMO-5-NAPHTHALEN-1-YL-THIOPHENE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC=C2C3=CC=C(S3)Br

Technology Process of 2-Bromo-5-(naphthalen-1-yl)thiophene

There total 6 articles about 2-Bromo-5-(naphthalen-1-yl)thiophene 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: 92.0%

trimethyl-(5-naphthalen-1-ylthiophen-2-yl)-silane (1273574-05-2) → 2-bromo-5-naphthalen-1-yl-thiophene (148875-82-5)

Guidance literature:

With N-Bromosuccinimide; In tetrahydrofuran; at 25 ℃; for 16h; Inert atmosphere;

DOI:10.1039/c0cc04302h

Reference yield:

2-bromothiophene (1003-09-4) + 1-Iodonaphthalene (90-14-2) → 2-bromo-5-naphthalen-1-yl-thiophene (148875-82-5)

Guidance literature:

With potassium fluoride; silver nitrate; PdCl₂(PPh)3; In dimethyl sulfoxide; at 100 ℃; for 8h;

DOI:10.1021/ol052063y

Reference yield:

1,8-diiodonaphthalene (1730-04-7) → 2-bromo-5-naphthalen-1-yl-thiophene (148875-82-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) Mg / <1,3-bis(diphenylphosphino)propane>nickel(II) chloride / 1) ether, 2) ether, reflux, 6 h

2: N-bromosuccinimide, AcOH / CHCl₃ / 0.5 h / Ambient temperature

With N-Bromosuccinimide; magnesium; acetic acid; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In chloroform;

DOI:10.1016/S0040-4020(01)90226-1

upstream raw materials:

1-(2-thienyl)naphthalene

2-bromothiophene

1-Iodonaphthalene

1,8-diiodonaphthalene

Refernces

• 1、 Kobayashi, Kei,Sugie, Atsushi,Takahashi, Masabumi,Masui, Kentaro,Mori, Atsunori. "Palladium-catalyzed coupling reactions of bromothiophenes at the C-H bond adjacent to the sulfur atom with a new activator system, AgNO3/KF". . p. 5083 - 5085. Retrieved 2007/10/03.
• 2、 Kuroda,Nakayama,Hoshino,Furusho. "Synthesis and properties of naphthalenes carrying two cofacially oriented α-oligothiophene units at the peri positions". . p. 7553 - 7556. Retrieved 2007/10/02.