3-Dodecylthiophene

Base Information

• Chemical Name: 3-Dodecylthiophene
• CAS No.: 104934-52-3
• Molecular Formula: C16H28S
• Molecular Weight: 252.46
• Hs Code.: 29339900
• European Community (EC) Number: 641-152-3
• DSSTox Substance ID: DTXSID40369961
• Nikkaji Number: J256.499H
• Wikidata: Q72470440
• Mol file: 104934-52-3.mol

Synonyms:3-Dodecylthiophene;104934-52-3;104934-53-4;Thiophene, 3-dodecyl-;3-Dodecylthiophene-2-D;MFCD00130121;2122800-12-6;3-Laurylthiophene;C16H28S;3-dodecyl thiophene;3-dodecyl-thiophene;3-Dodecylthiophene, 97%;SCHEMBL79577;BIDD:GT0253;DTXSID40369961;RFKWIEFTBMACPZ-UHFFFAOYSA-N;BBL100452;GEO-01280;MFCD26958733;MFCD31699966;STL554246;AKOS005254617;CS-W004390;SB66696;AC-33675;AS-14539;SY011230;SY246287;D2016;FT-0616209;F14937;A801103;W-200077

Chemical Property of 3-Dodecylthiophene

Chemical Property:

• Appearance/Colour: clear colorless to yellow liquid
• Vapor Pressure: 0.000276mmHg at 25°C
• Melting Point: -0.15°C (estimate)
• Refractive Index: n20/D 1.488(lit.)
• Boiling Point: 332.8 °C at 760 mmHg
• Flash Point: 114.9 °C
• PSA: 28.24000
• Density: 0.912 g/cm³
• LogP: 6.21150
• Storage Temp.: 0-6°C
• XLogP3: 8.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 11
• Exact Mass: 252.19117207
• Heavy Atom Count: 17
• Complexity: 156

Purity/Quality:

99% ^*data from raw suppliers

3-Dodecylthiophene ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCCCCCCCCC1=CSC=C1
• Uses: 3-Dodecylthiophene is a reactant used to make semiconducting copolymers. Conducting polymer precursor.

Technology Process of 3-Dodecylthiophene

There total 7 articles about 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: 95.0%

3-Bromothiophene (872-31-1) + dodecylzinc(II) bromide (869589-06-0) → 3-dodecylthiophene (104934-52-3,104934-53-4)

Guidance literature:

With [1,1'-bis(diphenylphosphino)-ferrocene]palladium(II) chloride-dichlormethane complex; In N,N-dimethyl acetamide; at 80 ℃; for 12h;

Reference yield: 88.0%

3-Bromothiophene (872-31-1) + 1-dodecylbromide (143-15-7) → 3-dodecylthiophene (104934-52-3,104934-53-4)

Guidance literature:

1-dodecylbromide; With iodine; magnesium; In tetrahydrofuran; at 70 ℃; for 2h; Inert atmosphere;

3-Bromothiophene; With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In tetrahydrofuran; at 20 ℃;

Reference yield: 84.0%

3-Bromothiophene (872-31-1) + 1-Iodododecane (4292-19-7) → 3-dodecylthiophene (104934-52-3,104934-53-4)

Guidance literature:

With pyridine; manganese; Tri(p-tolyl)phosphine; trifluoroacetic acid; cobalt(II) bromide; In N,N-dimethyl acetamide; at 70 ℃; for 24h; Reagent/catalyst; Solvent; Schlenk technique; Inert atmosphere;

DOI:10.1002/ejoc.201500784

upstream raw materials:

3-Bromothiophene

laurylmagnesium bromide

1-dodecylbromide

5,5-dimethyl-2-(thiophen-3-yl)-1,3,2-dioxaborinane

Downstream raw materials:

5,5'-bis(trimethylstannyl)-4,4'-bis(dodecyl)-2,2'-bithiophene

C₅₈H₇₈O₆S₄

C₃₂H₄₄O₃S₂

C₆₄H₈₆O₆S₄

Refernces

• 1、 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.
• 2、 Wang, Chao,Nakano, Kyohei,Lee, Hsiao Fang,Chen, Yujiao,Hong, You-Lee,Nishiyama, Yusuke,Tajima, Keisuke. "Intermolecular Arrangement of Fullerene Acceptors Proximal to Semiconducting Polymers in Mixed Bulk Heterojunctions". . p. 7034 - 7039. Retrieved 2018.
• 3、 Delgado, Paula A.,Liu, David Y.,Kean, Zachary,Wagener, Kenneth B.. "Synthesis of poly(3-dodecyl-2,5-thienylene vinylene) by solid-state metathesis polycondensation". . p. 9529 - 9532. Retrieved 2011.
• 4、 Vangeneugden,Vanderzande,Salbeck,Van Hal,Janssen,Hummelen,Brabec,Shaheen,Sariciftci. "Synthesis and characterization of a poly(1,3-dithienylisothianaphthene) derivative for bulk heterojunction photovoltaic cells". . p. 11106 - 11113. Retrieved 2001.
• 5、 Shaik, Baji,Han, Jin-Hee,Song, Dong Jin,Kang, Hun-Min,Kim, Ye Beyeol,Park, Chan Eon,Lee, Sang-Gyeong. "Synthesis of donor-acceptor copolymer using benzoselenadiazole as acceptor for OTFT". . p. 4070 - 4076. Retrieved 2016.
• 6、 -. "C(SP3)-C(SP2) CROSS-COUPLING REACTION OF ORGANOZINC REAGENTS AND HETEROCYCLIC (PSEUDO)HALIDES". Paragraph 103; 104. . Retrieved 2018/02/28.