Description

5,5′-Dibromo-2,2′-bithiophene (CAS No. 4805-22-5) is a high-purity brominated bithiophene derivative with the molecular formula C₈H₄Br₂S₂. This compound is a valuable building block in organic synthesis, particularly in the development of conjugated polymers and small molecules for optoelectronic applications. Its IUPAC name, 2-bromo-5-(5-bromothiophen-2-yl)thiophene, reflects its symmetrical structure featuring two thiophene rings bridged at the 2- and 2′-positions, each substituted with a bromine atom at the 5-position. This configuration makes it an excellent precursor for cross-coupling reactions such as Suzuki, Stille, or Kumada couplings, enabling the construction of extended π-conjugated systems. The compound is supplied as a crystalline solid with guaranteed purity, ideal for researchers in materials science, organic electronics, and pharmaceutical chemistry. Proper handling under inert conditions is recommended due to its sensitivity to light and moisture.

Properties

• CAS Number: 4805-22-5
• Complexity: 147
• IUPAC Name: 2-bromo-5-(5-bromo-2-thienyl)thiophene
• InChI: InChI=1S/C8H4Br2S2/c9-7-3-1-5(11-7)6-2-4-8(10)12-6/h1-4H
• InChI Key: SXNCMLQAQIGJDO-UHFFFAOYSA-N
• Exact Mass: 323.81007
• Molecular Formula: C8H4Br2S2
• Molecular Weight: 324.1
• SMILES: C1=C(SC(=C1)Br)C2=CC=C(S2)Br
• Topological: 56.5
• Monoisotopic Mass: 321.81212
• Synonyms: 5,5′-dibromo-2,2′-bithiophene, 4805-22-5, 2,2′-bithiophene, 5,5′-dibromo-, DTXSID90348605, DTXCID80299677, 695-323-2, inchi=1/c8h4br2s2/c9-7-3-1-5(11-7)6-2-4-8(10)12-6/h1-4, 2-bromo-5-(5-bromothiophen-2-yl)thiophene, 5,5-Dibromo-2,2-Bithiophene, 5,5′-dibromo-2,2-bithiophene, MFCD00219110, Maybridge4_002009, AC-776/41252583, BIDD:GT0566, SCHEMBL197157, 5,5′-bis[2-bromothiophene], 5,5′-dibromo-2,2’bithiophene, 5,5-bithiophene, HMS1526L07, 5,5 -dibromo-2,2 -biothiophene, 5,5′-dibromo-[2,2′]bithiophene, ALBB-035379, CCG-46129, GEO-00946, 5,5′-Dibromo-2,2′-bithiophene, AKOS004906106, AC-4911, CS-W013945, DS-1285, SB66309, 5,5 inverted exclamation mark -Dibromo-2,2 inverted exclamation mark -bithiophene, 5,5′-Dibromo-2,2′-bithiophene, 99%, SY030283, 2-bromo-5-(5-bromo(2-thienyl))thiophene, DB-050483, D2755, ST50320146, F14925, EN300-1720936, SR-01000635846-1

Application

5,5′-Dibromo-2,2′-bithiophene is widely used as a monomer in the synthesis of conjugated polymers for organic semiconductors, OLEDs, and photovoltaic devices. Its bromine substituents facilitate efficient polymerization via metal-catalyzed cross-coupling reactions, yielding materials with tunable electronic properties. The compound also serves as a key intermediate in medicinal chemistry for the development of thiophene-based bioactive molecules. Researchers leverage its structural rigidity and electronic characteristics to design advanced materials with tailored optoelectronic performance.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H315 (33.3%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (33.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• H335 (33.3%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)
• Acute Tox. 4 (100%)
• Skin Irrit. 2 (33.3%)
• Eye Irrit. 2A (33.3%)
• Acute Tox. 4 (100%)
• STOT SE 3 (33.3%)

If you are interested or have any questions, please contact us at support@atomfair.com

Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.