2,5-Dibromo-3-dodecylthiophene

Base Information

• Chemical Name: 2,5-Dibromo-3-dodecylthiophene
• CAS No.: 148256-63-7
• Molecular Formula: C16H26Br2S
• Molecular Weight: 410.25
• Hs Code.: 29339900
• DSSTox Substance ID: DTXSID10408038
• Nikkaji Number: J627.987B
• Wikidata: Q72464286
• Mol file: 148256-63-7.mol

Synonyms:2,5-Dibromo-3-dodecylthiophene;148256-63-7;Thiophene, 2,5-dibromo-3-dodecyl-;MFCD00274315;C16H26Br2S;2,5-Dibromo-3-laurylthiophene;BIDD:GT0375;SCHEMBL196435;DTXSID10408038;AKOS015898631;AC-4942;AC-4943;AM84447;CS-W011679;SB67016;2,5-bis(bromanyl)-3-dodecyl-thiophene;2,5-Dibromo-3-dodecylthiophene, 97%;AS-19034;SY037082;D4031;FT-0643420;A808748;J-507292;METHYL4-(4-ETHOXYPHENOXYCARBONYL)PHENYLCARBONATE

Chemical Property of 2,5-Dibromo-3-dodecylthiophene

Chemical Property:

• Vapor Pressure: 2.35E-05mmHg at 25°C
• Refractive Index: n20/D 1.53(lit.)
• Boiling Point: 407 °C at 760 mmHg
• Flash Point: 199.9 °C
• PSA: 28.24000
• Density: 1.326 g/cm³
• LogP: 7.73650
• Storage Temp.: 2-8°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: 9.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 11
• Exact Mass: 410.01015
• Heavy Atom Count: 19
• Complexity: 211

Purity/Quality:

99% ^*data from raw suppliers

2,5-Dibromo-3-dodecylthiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36:
• Hazard Codes: Xi:
• Statements: R36:
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCC1=C(SC(=C1)Br)Br
• Uses: 2,5-Dibromo-3-n-dodecylthiophene is used as an OLED intermediate, flavor and fragrance intermediate.

Technology Process of 2,5-Dibromo-3-dodecylthiophene

There total 4 articles about 2,5-Dibromo-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: 86.0%

3-dodecylthiophene (104934-52-3,104934-53-4) → 3-n-dodecyl-2,5-dibromothiophene (148256-63-7)

Guidance literature:

With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 40 ℃; for 3h;

DOI:10.1039/P29930000489

Reference yield:

1-dodecylbromide (143-15-7) → 3-n-dodecyl-2,5-dibromothiophene (148256-63-7)

Guidance literature:

Multi-step reaction with 2 steps

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

2: N-Bromosuccinimide / tetrahydrofuran / 0 °C

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

DOI:10.1002/pola.24174

Reference yield:

laurylmagnesium bromide (15890-72-9) → 3-n-dodecyl-2,5-dibromothiophene (148256-63-7)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 15 h / Reflux

2: N-Bromosuccinimide / tetrahydrofuran / 1 h / 0 - 5 °C

With N-Bromosuccinimide; In tetrahydrofuran;

DOI:10.1002/cjoc.201280021

upstream raw materials:

3-dodecylthiophene

1-dodecylbromide

laurylmagnesium bromide

Downstream raw materials:

1,4-bis((E)-2-(5-bromo-3-dodecylthiophen-2-yl)vinyl)benzene

C₂₃H₃₃BrOS

C₃₅H₅₈OS

Refernces

• 1、 Kim, Chul Young,Park, Jonggwang,Lee, Min Jung,Kwon, Soon-Ki,Kim, Jin Hak,Shin, Sung-Chul,Kim, Yun-Hi. "Poly(1,4-bis((E)-2-(3-dodecylthiophen-2-yl)vinyl)benzene) for solution processable organic thin film transistor". experimental part. p. 1659 - 1663. Retrieved 2012/08/14.
• 2、 Lee, Min-Jung,Kang, Moon Seong,Shin, Min-K.I.,Park, Jong-Won,Chung, Dae Sung,Park, Chan Eun,Kwon, Soon-K.I.,Kim, Yun-H.I.. "Synthesis and characterization of poly(1,4-bis((E)-2-(3dodecylthiophen-2- yl)vinyl)benzene) derivatives". experimental part. p. 3942 - 3949. Retrieved 2011/11/06.