2-Bromo-3-dodecylthiophene

Base Information

• Chemical Name: 2-Bromo-3-dodecylthiophene
• CAS No.: 139100-06-4
• Molecular Formula: C16H27BrS
• Molecular Weight: 331.36
• Hs Code.: 29349990
• European Community (EC) Number: 624-934-9
• DSSTox Substance ID: DTXSID60439776
• Nikkaji Number: J524.420J
• Wikidata: Q72455226
• Mol file: 139100-06-4.mol

Synonyms:2-BROMO-3-DODECYLTHIOPHENE;139100-06-4;Thiophene, 2-bromo-3-dodecyl-;2-bromo-3-dodecyl-thiophene;MFCD10000891;C16H27BrS;2-Bromo-3-laurylthiophene;SCHEMBL198675;2-bromanyl-3-dodecyl-thiophene;DTXSID60439776;IMILVTHOOISGRW-UHFFFAOYSA-N;2-Bromo-3-dodecylthiophene, 95%;AKOS015898611;AS-2037;CS-W009854;FD14060;SY037089;B3691;FT-0743918;A807483;J-508215

Chemical Property of 2-Bromo-3-dodecylthiophene

Chemical Property:

• Vapor Pressure: 2.35E-05mmHg at 25°C
• Refractive Index: n20/D 1.509
• Boiling Point: 370.5 °C at 760 mmHg
• Flash Point: 177.9 °C
• PSA: 28.24000
• Density: 1.13 g/cm³
• LogP: 6.97400
• Storage Temp.: 2-8°C
• XLogP3: 8.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 11
• Exact Mass: 330.10168
• Heavy Atom Count: 18
• Complexity: 184

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCC1=C(SC=C1)Br
• Uses: 2-Bromo-3-dodecylthiophene is used in the synthesis of a poly(octathiophene) based copolymer, which is an organic semiconductor that may be used in thin film transistor.

Technology Process of 2-Bromo-3-dodecylthiophene

There total 4 articles about 2-Bromo-3-dodecylthiophene 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: 97.0%

3-dodecylthiophene (104934-52-3,104934-53-4) → 2-bromo-3-dodecylthiophene (139100-06-4)

Guidance literature:

With N-Bromosuccinimide;

DOI:10.1002/pola.24641

Reference yield:

laurylmagnesium bromide (15890-72-9) → 2-bromo-3-dodecylthiophene (139100-06-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / Ni(dppp)Cl₂ / diethyl ether / 35 °C

2: 41 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-dodecylbromide (143-15-7) → 2-bromo-3-dodecylthiophene (139100-06-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); magnesium / tetrahydrofuran

2: N-Bromosuccinimide / N,N-dimethyl-formamide

With N-Bromosuccinimide; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); magnesium; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1039/c5ra23805f

upstream raw materials:

3-dodecylthiophene

laurylmagnesium bromide

1-dodecylbromide

Downstream raw materials:

3,3?-didodecyl-2,2′;5′,2″;5″,2?-quaterthiophene

C₂₃H₃₄OS

5,5'''-dibromo-3,3'''-bis(dodecyl)-2,2':5',2'':5'',2'''-quarterthiophene

2-(3-dodecylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Refernces

• 1、 Kim, Heung Gyu,Kim, Min,Clement, J. Arul,Lee, Jaewon,Shin, Jisoo,Hwang, Hyeongjin,Sin, Dong Hun,Cho, Kilwon. "Energy Level Engineering of Donor Polymers via Inductive and Resonance Effects for Polymer Solar Cells: Effects of Cyano and Alkoxy Substituents". . p. 6858 - 6868. Retrieved 2015.
• 2、 Sonar, Prashant,Williams, Evan L.,Singh, Samarendra P.,Dodabalapur, Ananth. "Thiophene-benzothiadiazole-thiophene (D-A-D) based polymers: Effect of donor/acceptor moieties adjacent to D-A-D segment on photophysical and photovoltaic properties". . p. 10532 - 10541. Retrieved 2011.
• 3、 Lim, Dae-Hee,Kim, Yeon-Ju,Kim, Yeong-A,Hwang, Kyoungtae,Park, Jong-Jin,Kim, Dong-Yu. "Structural Insight into Aggregation and Orientation of TPD-Based Conjugated Polymers for Efficient Charge-Transporting Properties". . p. 4629 - 4638. Retrieved 2019/05/08.
• 4、 -. "Chemical synthesis and application research of cyanogroup containing functional material for modifying perovskite layer in perovskite solar cell". Paragraph 0022; 0025; 0026. . Retrieved 2017/05/23.