3-Iodothiophene

Base Information

• Chemical Name: 3-Iodothiophene
• CAS No.: 10486-61-0
• Molecular Formula: C4H3IS
• Molecular Weight: 210.038
• Hs Code.: 29349990
• European Community (EC) Number: 234-009-8
• DSSTox Substance ID: DTXSID60146791
• Nikkaji Number: J149.962I
• Wikidata: Q72484687
• Mol file: 10486-61-0.mol

Synonyms:3-Iodothiophene;10486-61-0;Thiophene, 3-iodo-;3-lodothiophene;EINECS 234-009-8;MFCD00037901;3-Iodothiophene, stab. with copper;3-iodo-thiophene;3-Thienyl Iodide;3-Iodothiophene #;3-Iodothiophene, >=97%;BIDD:GT0252;SCHEMBL150265;DTXSID60146791;BCP22807;BBL103104;STL556914;AKOS015853830;BCP9000129;CS-W004948;AS-17578;SY030129;AM20070697;FT-0615916;I0380;EN300-108555;A801079;J-001277

Chemical Property of 3-Iodothiophene

Chemical Property:

• Appearance/Colour: red brown liquid
• Melting Point: -13.4 °C
• Refractive Index: n20/D 1.657(lit.)
• Boiling Point: 195.211 °C at 760 mmHg
• Flash Point: 71.862 °C
• PSA: 28.24000
• Density: 2.08 g/cm³
• LogP: 2.35270
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 209.90002
• Heavy Atom Count: 6
• Complexity: 46.8

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Iodothiophene ^*data from reagent suppliers

Safty Information:

• Statements: 36/38
• Safety Statements: 26-36/37/39-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CSC=C1I
• Uses: 3-Iodothiophene was used in the synthesis of 3-thienylzinc iodide via reaction with zinc, followed by coupling with aryl halides. It was also used in the preparation of 3-(perfluorooctyl)thiophene, required for the synthesis of poly(3-perfluorooctylthiophene) conjugated polymer.

Technology Process of 3-Iodothiophene

There total 19 articles about 3-Iodothiophene 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-Bromothiophene (872-31-1) → 3-thienyl iodide (10486-61-0)

Guidance literature:

3-Bromothiophene; With n-butyllithium; In hexane; at -70 ℃; Inert atmosphere;

In tetrahydrofuran; hexane; at -70 - 0 ℃; Inert atmosphere;

With 1,2-Diiodoethane; In tetrahydrofuran; hexane; at -70 - 20 ℃; chemoselective reaction; Inert atmosphere;

DOI:10.1080/00397910902763904

Reference yield: 84.0%

2-Iodothiophene (3437-95-4,149762-92-5) + 3-Bromopyridine (626-55-1,163928-56-1) + 2-Ethylhexyl alcohol (104-76-7) → thiophene (188290-36-0,8014-23-1,25233-34-5) + 3-thienyl iodide (10486-61-0) + 3-bromo-4-((2-ethylhexyl)oxy)pyridine

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 25 ℃; for 20h; regioselective reaction; Inert atmosphere; Glovebox; Sealed tube;

DOI:10.1021/jacs.1c06481

Reference yield: 83.0%

potassium 3-thiophenetrifluoroborate → 3-thienyl iodide (10486-61-0)

Guidance literature:

With chloroamine-T; sodium iodide; In tetrahydrofuran; water; at 20 ℃; for 0.166667h;

DOI:10.1016/j.tetlet.2003.10.149

upstream raw materials:

3,4-diiodothiophene

2,3,4,5-tetraiodo-thiophene

2-Iodothiophene

3-Bromothiophene

Downstream raw materials:

3-(o-nitrophenyl)thiophene

3-[2-Methylene-cyclohex-(Z)-ylidenemethyl]-thiophene

3-[2-Methylene-cyclohex-(E)-ylidenemethyl]-thiophene

(4S,6S)-6-[2-(2,4-Dichloro-phenyl)-ethyl]-4-thiophen-3-yl-tetrahydro-pyran-2-one

Refernces

• 1、 Kabalka, George W.,Mereddy, Arjun R.. "A facile synthesis of aryl iodides via potassium aryltrifluoroborates". . p. 343 - 345. Retrieved 2004.
• 2、 Sonoda, Motohiro,Kinoshita, Shoko,Luu, Thanh,Fukuda, Hiroshi,Miki, Koji,Umeda, Rui,Tobe, Yoshito. "Selective metallation of 3-halothiophenes: Practical methods for the synthesis of 2-bromo-3-formylthiophene". . p. 3315 - 3323. Retrieved 2009.
• 3、 Nagarjuna,Yurt, Serkan,Jadhav, Kedar G.,Venkataraman. "Impact of pendant 1,2,3-triazole on the synthesis and properties of thiophene-based polymers". . p. 8045 - 8050. Retrieved 2010.
• 4、 Bhilare, Sachin V.,Deorukhkar, Amol R.,Darvatkar, Nitin B.,Salunkhe, Manikrao M.. "Regioselective iodination of arenes using iodine/NaBO3· 4H2O system in ionic liquid". . p. 2881 - 2888. Retrieved 2008.
• 5、 Thiebes, Christoph,Prakash, G. K. Surya,Petasis, Nicos A.,Olah, George A.. "Mild preparation of haloarenes by ipso-substitution of arylboronic acids with N-halosuccinimides". . p. 141 - 142. Retrieved 1998.
• 6、 Bandar, Jeffrey S.,Klaus, Danielle R.,Puleo, Thomas R.. "Nucleophilic C-H Etherification of Heteroarenes Enabled by Base-Catalyzed Halogen Transfer". supporting information. p. 12480 - 12486. Retrieved 2021/08/24.