Description

4-Bromo-o-xylene (CAS No. 583-71-1) is a high-purity aromatic compound with the molecular formula C₈H₉Br. Also known as 4-bromo-1,2-dimethylbenzene, this halogenated derivative of o-xylene is a versatile intermediate in organic synthesis and pharmaceutical research. Its structure features a bromine substituent at the 4-position of a 1,2-dimethylbenzene ring, offering selective reactivity for electrophilic substitution and metal-catalyzed coupling reactions.

This compound is supplied as a clear to pale-yellow liquid or low-melting solid with a characteristic aromatic odor. It is soluble in organic solvents such as ethanol, ether, and chloroform but insoluble in water. Suitable for use in Grignard reactions, Suzuki couplings, and other cross-coupling methodologies, our 4-Bromo-o-xylene is rigorously tested for purity (typically ≥97% by GC) and is ideal for demanding applications in medicinal chemistry and material science.

Packaged under inert gas to ensure stability, this product is available in quantities ranging from grams to multi-kilogram scales. Technical data including ¹H/¹³C NMR spectra and GC-MS reports are provided upon request.

Properties

• CAS Number: 583-71-1
• Complexity: 90.6
• IUPAC Name: 4-bromo-1,2-dimethyl-benzene
• InChI: InChI=1S/C8H9Br/c1-6-3-4-8(9)5-7(6)2/h3-5H,1-2H3
• InChI Key: QOGHRLGTXVMRLM-UHFFFAOYSA-N
• Exact Mass: 183.98876
• Molecular Formula: C8H9Br
• Molecular Weight: 185.06
• SMILES: CC1=C(C=C(C=C1)Br)C
• Monoisotopic Mass: 183.98876
• Synonyms: 4-Bromo-o-xylene, Benzene, 4-bromo-1,2-dimethyl-, 1-Bromo-3,4-dimethylbenzene, 4-Bromo-1,2-xylene, o-Xylene, 4-bromo-, 4-Bromo-ortho-xylene, 4-bromo-o-xylol, AI3-07015, EINECS 209-518-3, BRN 2040354, DTXSID9074640, 4-05-00-00928 (Beilstein Handbook Reference), NSC 60147, DTXCID1042364, o-Xylene, 4-bromo-(6CI,7CI,8CI), 209-518-3, qoghrlgtxvmrlm-uhfffaoysa-n, 4-Bromo-1,2-dimethylbenzene, 583-71-1, 3,4-Dimethylbromobenzene, 3,4-Xylyl bromide, 3,4-Dimethylphenyl bromide, 4-Bromo-1,2-dimethyl-benzene, X45692CHP5, MFCD00000086, NSC-60147, 5-bromo-xylene, NSC60147, dimethyl-5-bromobenzene, SCHEMBL40336, SCHEMBL456479, UNII-X45692CHP5, 1-bromo-3,4-dimethyl-benzene, SCHEMBL1004013, SCHEMBL1004143, SCHEMBL1098930, SCHEMBL15063913, SCHEMBL19586330, STL268845, 4-Bromo-1,2-dimethylbenzene, 70%, AKOS005145661, AC-3176, DB-028266, B1346, NS00033917, ST50406329, EN300-64290, 3,4-Dimethylbromobenzene; 4-Bromo-1,2-dimethylbenzene;4-Bromo-o-xylene

Application

4-Bromo-o-xylene serves as a key building block in the synthesis of agrochemicals, pharmaceuticals, and liquid crystals. It is widely employed in palladium-catalyzed cross-coupling reactions (e.g., Suzuki-Miyaura) to construct biaryl systems. Researchers utilize this compound to introduce bromine-functionalized dimethylbenzene moieties into complex molecules for drug discovery programs. Additionally, it finds use in the development of organic semiconductors and ligand frameworks for catalysis.

Safety and Hazards

GHS Hazard Statements

• H302 (88%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (98%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (98%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (94%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
• H400 (82%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (88%)
• Skin Irrit. 2 (98%)
• Eye Irrit. 2 (98%)
• STOT SE 3 (94%)
• Aquatic Acute 1 (82%)

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