1-(3-Bromophenyl)-2,5-dimethylpyrrole is an N-aryl-2,5-dimethylpyrrole derivative in which a pyrrole ring is directly bonded to a 3-bromophenyl group, and the specific combination of an electron-rich pyrrole core, two methyl substituents at C2 and C5 for steric shielding, and a meta-bromine handle creates a uniquely configured scaffold for constructing sterically demanding, functionalized small molecules in drug discovery and materials chemistry.
1-(3-Bromophenyl)-2,5-dimethylpyrrole (CAS 127257-87-8) is an organic compound belonging to the pyrrole family — a five-membered heteroaromatic ring containing one nitrogen atom. The molecular formula is C₁₂H₁₂BrN with a molecular weight of 250.13–250.14 g/mol, and the compound is typically supplied at a purity of ≥95% as a light brown solid. The IUPAC name is 1-(3-bromophenyl)-2,5-dimethylpyrrole, and the MDL number is MFCD04308119.
1-(3-Bromophenyl)-2,5-dimethylpyrrole is a versatile building block in medicinal chemistry. The pyrrole scaffold is widely recognized in drug discovery — it exists in many natural products, drug molecules and pesticides, and the biological relevance of pyrrole derivatives spans antiviral, antibacterial, antifungal, anticancer and anti-inflammatory activities. The presence of a bromine atom on the meta-position of the phenyl ring and two methyl groups on the pyrrole ring makes 1-(3-Bromophenyl)-2,5-dimethylpyrrole uniquely suited for fragment-based drug discovery, where the methyl groups provide steric shielding while the meta‑bromine serves as an orthogonal handle for Suzuki, Buchwald-Hartwig, and other cross‑coupling reactions.
In materials science, 1-(3-Bromophenyl)-2,5-dimethylpyrrole has been investigated for its electronic properties. The electron-rich nature of the pyrrole ring may enable charge transport, and the rigid, conjugated framework makes it a candidate monomer for constructing extended π‑systems relevant to organic light‑emitting diodes (OLEDs) and organic photovoltaics (OPVs).
Product Parameters
Parameter
Specification
CAS Number
127257-87-8
Molecular Formula
C₁₂H₁₂BrN
Molecular Weight
250.13–250.14 g/mol
Purity
≥95% as standard; 98% available upon request
Appearance
Light brown solid
Canonical SMILES
CC1=CC=C(N1C2=CC(=CC=C2)Br)C
Storage Condition
Long-term storage: cool, dry place
DOT/IATA Transport
Not hazardous material
GHS Signal Word
Warning
Solubility
Soluble in organic solvents (EtOAc, DCM, THF, DMF)
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Both research/pharma grade(≥98%)and high-purity impurity grade(≥99%)available to meet diverse customer needs.
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Each batch undergoes:
● Gas chromatography (GC) – purity ≥97.0%
● Non‑aqueous titration – purity ≥97.0%
● Refractive index – confirmatory analysis
● ¹H NMR – structural verification
● Appearance – colorless to light yellow to light orange clear liquid
A comprehensive COA, MSDS (with full GHS information), and certificate of origin accompany every shipment.
Frequently Asked Questions (FAQ)
Q1:Why is the meta‑bromine substituent significant for this compound?
A: The meta‑bromine substituent serves as a versatile synthetic handle for transition‑metal‑catalyzed cross‑coupling reactions (Suzuki, Heck, Sonogashira, Buchwald‑Hartwig). This allows medicinal chemists to rapidly introduce diverse aryl, alkynyl, or amino groups at the meta‑position of the phenyl ring, enabling efficient structure–activity relationship (SAR) studies.
Q2: Is the compound soluble in common organic solvents?
A: Yes. The compound is likely soluble in organic solvents such as ethyl acetate, dichloromethane, THF, and DMF due to its aromatic nature.
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