2,5-Dibromothiophene-3-carbaldehyde

Base Information

• Chemical Name: 2,5-Dibromothiophene-3-carbaldehyde
• CAS No.: 1193-69-7
• Molecular Formula: C5H2Br2OS
• Molecular Weight: 269.944
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID20356031
• Nikkaji Number: J149.313B
• Wikidata: Q82135161
• Mol file: 1193-69-7.mol

Synonyms:2,5-dibromothiophene-3-carbaldehyde;1193-69-7;2,5-Dibromothiophene-3-carboxaldehyde;2,5-dibromo-3-formylthiophene;2,5-Dibromo-3-thiophenecarbaldehyde;3-Thiophenecarboxaldehyde, 2,5-dibromo-;SCHEMBL96226;AMY7254;DTXSID20356031;GBJBDOWMZMXKCD-UHFFFAOYSA-N;BAA19369;AKOS013400090;2,5-Dibromothiophene-3-carboxaldehyde, 97%;EN300-307596;Z1190318840

Chemical Property of 2,5-Dibromothiophene-3-carbaldehyde

Chemical Property:

• Melting Point: 47-52°C
• Boiling Point: 136 °C(Press: 26 Torr)
• Flash Point: >110℃
• PSA: 45.31000
• Density: 2.195±0.06 g/cm3(Predicted)
• LogP: 3.08560
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 269.81726
• Heavy Atom Count: 9
• Complexity: 120

Purity/Quality:

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

2,5-Dibromothiophene-3-carbaldehyde ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25-36
• Safety Statements: 26-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(SC(=C1C=O)Br)Br

Technology Process of 2,5-Dibromothiophene-3-carbaldehyde

There total 7 articles about 2,5-Dibromothiophene-3-carbaldehyde 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: 91.72%

3-thiophene carboxaldehyde (498-62-4) → 2,5-dibromo thiophene-3-carboxaldehyde (1193-69-7)

Guidance literature:

With hydrogen bromide; bromine; In diethyl ether; water; at 50 ℃; Cooling with ice;

DOI:10.1002/chem.201201437

Reference yield: 91.2%

(2,5-dibromothiophen-3-yl)methanol (161490-95-5) → 2,5-dibromo thiophene-3-carboxaldehyde (1193-69-7)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1039/c9tc05704h

Reference yield:

2,5-dibromo-3-methylthiophene (13191-36-1) → 2,5-dibromo thiophene-3-carboxaldehyde (1193-69-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / Br₂, azobisisobutyronitril (AIBN) / CCl₄ / 5 h / Heating

2: 1.) Na₂CO₃, 2.) aq. HCl / 1.) EtOH, water, reflux, 12 h, 2.) EtOH, ether, reflux, 1 h

With hydrogenchloride; 2,2'-azobis(isobutyronitrile); bromine; sodium carbonate; In tetrachloromethane;

upstream raw materials:

3-thiophene carboxaldehyde

2,5-dibromo-3-dibromomethylthiophene

2,5-dibromo-3-methylthiophene

3-Methylthiophene

Downstream raw materials:

5-bromo-3-thiophenecarbaldehyde

(E)-3-(2,5-dibromothiophen-3-yl) acrylic acid

Refernces

• 1、 Algi, Fatih,Cihaner, Atilla. "A novel terthienyl based polymer electrochrome with peripheral BODIPY". . p. 3469 - 3475. Retrieved 2012.
• 2、 Chen, Lixia,Shen, Ping,Zhang, Zhi-Guo,Li, Yongfang. "Side-chain engineering of benzodithiophene-thiophene copolymers with conjugated side chains containing the electron-withdrawing ethylrhodanine group". . p. 12005 - 12015. Retrieved 2015.
• 3、 Van Beek, Rick,Zoombelt, Arjan P.,Jenneskens, Leonardas W.,Van Walree, Cornelis A.,De Mello Donega, Celso,Veldman, Dirk,Janssen, Rene A. J.. "Side chain mediated electronic contact between a tetrahydro-4H-thiopyran-4- ylidene-appended polythiophene and CdTe quantum dots". . p. 8075 - 8083. Retrieved 2006.
• 4、 Lehnherr, Dan,Waterloo, Andreas R.,Goetz, Katelyn P.,Payne, Marcia M.,Hampel, Frank,Anthony, John E.,Jurchescu, Oana D.,Tykwinski, Rik R.. "Isomerically pure syn-anthradithiophenes: Synthesis, properties, and FET performance". . p. 3660 - 3663. Retrieved 2012.
• 5、 Lee, Kwang-Hoi,Morino, Kazuhide,Sudo, Atsushi,Endo, Takeshi. "Preparation and properties of a novel polythiophene, poly[(3- hexyliminomethyl)thiophene] with a high regioregularity". . p. 1190 - 1194. Retrieved 2011.
• 6、 Kuo, Cheng-Yu,Huang, Yu-Chen,Hsiow, Chuen-Yo,Yang, Yu-Wen,Huang, Ching-I,Rwei, Syang-Peng,Wang, Hsing-Lin,Wang, Leeyih. "Effect of side-chain architecture on the optical and crystalline properties of two-dimensional polythiophenes". . p. 5985 - 5997. Retrieved 2013.
• 7、 Sambathkumar,Varathan,Subramanian,Somanathan. "Design of medium band gap random terpolymers containing fluorene linked diketopyrrolopyrrole and thiophene co-monomers: An experimental and theoretical study". supporting information. p. 1377 - 1386. Retrieved 2016/02/19.