5''-Bromo-2,2':5',2''-terthiophene-5-carboxaldehyde

Base Information

• Chemical Name: 5''-Bromo-2,2':5',2''-terthiophene-5-carboxaldehyde
• CAS No.: 161726-69-8
• Molecular Formula: C13H7BrOS3
• Molecular Weight: 355.3
• Hs Code.: 29309090
• DSSTox Substance ID: DTXSID00565806
• Nikkaji Number: J2.159.486E
• Wikidata: Q82451085
• Mol file: 161726-69-8.mol

Synonyms:161726-69-8;5''-Bromo-2,2':5',2''-terthiophene-5-carboxaldehyde;5''-bromo-[2,2':5',2''-terthiophene]-5-carbaldehyde;5''-Bromo-2,2'-5',2''-terthiophene-5-carboxaldehyde;5-[5-(5-BROMOTHIOPHEN-2-YL)THIOPHEN-2-YL]THIOPHENE-2-CARBALDEHYDE;GEO-00572;5''-Bromo-2,2:5',2''-terthiophene-5-carboxaldehyde;[2,2':5',2''-Terthiophene]-5-carboxaldehyde, 5''-bromo-;5/'/'-BROMO-2,2/':5/',2/'/'-TERTHIOPHENE-5-CARBOXALDEHYDE;DSYKMLTVEGWLFR-UHFFFAOYSA-N;5-Bromo-5''-formyl-2,2':5',2''-terthiophene;SCHEMBL50461;Bromoterthiophenecarboxaldehyde;DTXSID00565806;MFCD02093442;AKOS015835945;AS-2717;N-CBZ-4-PIPERIDINEPROPIONICACID;SB66785;B2058;CS-0111052;T70371;A883064;W-200147;5'-(5-bromothiophen-2-yl)-[2,2'-bithiophene]-5-carbaldehyde;3~5~-Bromo[1~2~,2~2~:2~5~,3~2~-terthiophene]-1~5~-carbaldehyde;5-[5-(5-bromothiophen-2-yl)thiophen-2-yl]thiophene-2-carbaldehyde, >94.0%(GC)

Chemical Property of 5''-Bromo-2,2':5',2''-terthiophene-5-carboxaldehyde

Chemical Property:

• Melting Point: 164 °C
• Boiling Point: 460.0±45.0 °C(Predicted)
• PSA: 101.79000
• Density: 1.642±0.06 g/cm3(Predicted)
• LogP: 5.78010
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 353.88424
• Heavy Atom Count: 18
• Complexity: 315

Purity/Quality:

98% ^*data from raw suppliers

5''''-Bromo-[2,2'':5'',2''''-terthiophene]-5-carbaldehyde ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(SC(=C1)C2=CC=C(S2)C3=CC=C(S3)Br)C=O
• Uses: 5''''-Bromo-[2,2'':5'',2''''-terthiophene]-5-carbaldehyde is a reagent used in the preparation of aldehyde-capped thiophene oligomers. It is also used in the preparation of organic dyes incorporating carbazole or dendritic iodocarbazole unit to enhance the performance of dye-sensitized solar cells.

Technology Process of 5''-Bromo-2,2':5',2''-terthiophene-5-carboxaldehyde

There total 3 articles about 5''-Bromo-2,2':5',2''-terthiophene-5-carboxaldehyde 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%

2,2':5',2''-terthiophene-5-carboxaldehyde (7342-41-8) → 5″-bromo-2,2′:5′,2″-terthiophene-5-carboxaldehyde (161726-69-8)

Guidance literature:

With N-Bromosuccinimide; In dichloromethane; acetic acid; for 24h; Ambient temperature;

DOI:10.1016/0040-4020(95)00038-A

Reference yield: 76.0%

5-bromo-2,2':5',2''-terthiophene (94581-95-0) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 5″-bromo-2,2′:5′,2″-terthiophene-5-carboxaldehyde (161726-69-8)

Guidance literature:

With trichlorophosphate; In dichloromethane; at 20 - 70 ℃; for 14h; Solvent; Cooling with ice;

DOI:10.1039/d0tc02168g

Reference yield:

2,2':5',2''-terthiophene (1081-34-1) → 5″-bromo-2,2′:5′,2″-terthiophene-5-carboxaldehyde (161726-69-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / POCl₃ / 1,2-dichloro-ethane / 4 h / 60 °C

2: 89 percent / Br₂, NaHCO₃ / CHCl₃ / 4 h / Heating

With bromine; sodium hydrogencarbonate; trichlorophosphate; In chloroform; 1,2-dichloro-ethane;

DOI:10.1016/0040-4039(94)02347-E

upstream raw materials:

2,2':5',2''-terthiophene-5-carboxaldehyde

2,2':5',2''-terthiophene

5-bromo-2,2':5',2''-terthiophene

N,N-dimethyl-formamide

Downstream raw materials:

MP₃T-CHO

2-cyano-3-{5-{4-[N,N-bis(4-(2-ethylhexyloxy)phenyl)amino]phenyl}-2,2':5',2''-terthienyl-5''-yl}acrylic acid

5-{4-[N,N-bis(4-(2-ethylhexyloxy)phenyl)amino]phenyl}-2,2':5',2''-terthiophene-5''-carbaldehyde

C₄₄H₂₇NO₂S₆

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