2-Bromo-3-octylthiophene

Base Information

• Chemical Name: 2-Bromo-3-octylthiophene
• CAS No.: 145543-83-5
• Molecular Formula: C12H19BrS
• Molecular Weight: 275.253
• Hs Code.: 29349990
• European Community (EC) Number: 878-374-7
• DSSTox Substance ID: DTXSID00444485
• Nikkaji Number: J524.419F
• Wikidata: Q72448878
• Mol file: 145543-83-5.mol

Synonyms:2-Bromo-3-octylthiophene;145543-83-5;Thiophene, 2-bromo-3-octyl-;2-bromo-3-octyl-thiophene;2-Bromo-3-n-octylthiophene;MFCD13193238;C12H19BrS;SCHEMBL1225175;DTXSID00444485;2-Bromo-3-octylthiophene, 97%;ISONQKSIWXLJOQ-UHFFFAOYSA-N;AKOS015898630;AC-4939;CS-W012325;DS-1914;SY036435;B3733;FT-0751412;A808387;J-508242

Chemical Property of 2-Bromo-3-octylthiophene

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.521
• Boiling Point: 307.088 °C at 760 mmHg
• Flash Point: 139.522 °C
• PSA: 28.24000
• Density: 1.213 g/cm³
• LogP: 5.41360
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 6.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 7
• Exact Mass: 274.03908
• Heavy Atom Count: 14
• Complexity: 138

Purity/Quality:

99% ^*data from raw suppliers

2-Bromo-3-octylthiophene ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC1=C(SC=C1)Br

Technology Process of 2-Bromo-3-octylthiophene

There total 6 articles about 2-Bromo-3-octylthiophene 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: 99.0%

3-octylthiophene (65016-62-8,104934-51-2) → 2-bromo-3-octylthiophene (145543-83-5)

Guidance literature:

With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20 ℃; Darkness;

Reference yield:

octylmagnesium bromide (17049-49-9) → 2-bromo-3-octylthiophene (145543-83-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 61 percent / Ni(dppp)Cl₂ / diethyl ether / 35 °C

2: 40 percent / Br₂ / acetic acid / 0.5 h / 0 °C

With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); bromine; In diethyl ether; acetic acid;

DOI:10.1021/jo00056a024

Reference yield:

1-bromo-octane (111-83-1) → 2-bromo-3-octylthiophene (145543-83-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Mg / diethyl ether

1.2: 73 percent / Ni(dppp)Cl₂ / diethyl ether / 24 h / Heating

2.1: 82 percent / NBS / acetic acid; CHCl₃

With N-Bromosuccinimide; magnesium; In diethyl ether; chloroform; acetic acid; 1.1: Metallation / 1.2: Alkylation / 2.1: Bromination;

DOI:10.1021/jo991359c

upstream raw materials:

3-octylthiophene

3-Bromothiophene

octylmagnesium bromide

1-bromo-octane

Downstream raw materials:

3,3″-dioctyl-2,2′:5′,2″-trithiophene

methyl 4-(3-octylthiophen-2-yl)benzoate

2-bromo-5-iodo-3-octylhiophene

C₆₀H₈₂N₂O₂S₂

Refernces

• 1、 Narayana, Yemineni S. L. V.,Baumgarten, Martin,Müllen, Klaus,Chandrasekar, Rajadurai. "Tuning the Solid State Emission of Thin Films/Microspheres Obtained from Alternating Oligo(3-octylthiophenes) and 2,6-Bis(pyrazole)pyridine Copolymers by Varying Conjugation Length and Eu3+/Tb3+ Metal Coordination". . p. 4801 - 4812. Retrieved 2015.
• 2、 Bras, Jerome,Pepin-Donat, Brigitte. "1H and13C NMR study of regioregular head-to-tail oligo(octylthiophene)s and poly(octylthiophene)". . p. 57 - 67. Retrieved 2001.
• 3、 Chang, Qing,Cheng, Xiaohong,Ding, Wei,Ma, Tao,Zhang, Lin. "Thiophene-benzothiadiazole based donor–acceptor–donor (D-A-D) bolaamphiphiles, self-assembly and photophysical properties". . . Retrieved 2021/11/03.
• 4、 -. "TRIPHENYLAMINE COMPOUNDS, POLYMERS MADE THEREFROM AND ELECTROCHROMIC DEVICE COMPRISING THE SAME". Paragraph 0196; 0199; 0204-0206. . Retrieved 2018/05/03.