3,4-dichloro-1-bromobenzene
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Product Description
3,4-Dichlorobromobenzene is a colorless to pale-yellow liquid that solidifies below 24 °C, bearing a bromine at position 1 and chlorines at positions 3 and 4 of the benzene ring; it is immiscible with water yet readily dissolves in ethanol, dichloromethane and other common organic solvents. Industrially it is manufactured in 90 % yield by Fe-catalyzed bromination of o-dichlorobenzene at 20–45 °C, giving 98.5 % purity that is pushed to ≥ 99.5 % through multistage crystallisation that removes the 6–7 % of its 2,3-dichloro isomer formed concomitantly.
Other Information
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Spectral Data Available: NMR (¹H, ¹³C), IR (FTIR, ATR-IR), Raman, and Mass Spectrometry (GC-MS) data are accessible via PubChem.
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Patent & Literature Presence: The compound is mentioned in patent documents and scientific literature (e.g., in Nature Synthesis), indicating its relevance in research and development.
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Synonyms: Numerous synonyms exist, including 1-Bromo-3,4-dichlorobenzene, 3,4-Dichlorobromobenzene, and 1,2-Dichloro-4-bromobenzene.
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Regulatory Listing: Registered under the EU's REACH regulation (Status: Active).
Synthesis and Production
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Industrial Synthesis Method: Typically manufactured via the Fe-catalyzed bromination of o-dichlorobenzene at 20–45 °C.
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Yield & Purity: The process yields approximately 90% of the target product with an initial purity of about 98.5%.
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Byproduct: The reaction produces approximately 6–7% of the 2,3-dichlorobromobenzene isomer as a byproduct.
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Purification: Final purity can be increased to ≥ 99.5% through multi-stage crystallization techniques.
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Regulatory Status: Listed as ACTIVE in the U.S. EPA Toxic Substances Control Act (TSCA) inventory.
Uses and Applications
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Agrochemical Intermediate: A key building block for synthesizing several herbicides, including:
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Propanil (Stam F-34): A selective herbicide for rice paddies.
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Linuron, Chlorbufam, and Metoxuron: Various broad-spectrum herbicides.
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Pharmaceutical Intermediate: Its differentiated reactivity (Br vs. Cl) makes it a valuable "molecular scaffold" in drug discovery. It is used in modern coupling reactions like Suzuki coupling and Buchwald–Hartwig amination to construct complex drug molecules.
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Advanced Material Precursor: Serves as a basic unit in the development of OLED (Organic Light-Emitting Diode) and liquid crystal materials. The halogen atoms help fine-tune the electronic properties, molecular alignment, and luminescent performance of the materials.
Chemical and Physical Properties
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Chemical Identifiers:
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CAS Number: 18282-59-2
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EC Number: 242-160-6
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UNII: XE64D7GD53
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DSSTox ID: DTXSID2066353
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Molecular Formula: C₆H₃BrCl₂
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IUPAC Name: 4-bromo-1,2-dichlorobenzene
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Physical Description: A colorless to pale-yellow liquid at room temperature, which solidifies below 24 °C.
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Solubility: Immiscible with water. Readily soluble in common organic solvents such as ethanol and dichloromethane.
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Computed Physical/Chemical Properties:
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Molecular Weight: 225.89 g/mol
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XLogP3: 4.1 (Indicates high hydrophobicity)
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Hydrogen Bond Donor/Acceptor Count: 0
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Rotatable Bond Count: 0
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Topological Polar Surface Area: 0 Ų
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Complexity: 97.1
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Structural Feature: A benzene ring substituted with bromine at position 1 and chlorines at positions 3 and 4 (or 1,2-dichloro-4-bromo). The bromine atom is more reactive than the chlorines under typical transition-metal catalysis conditions, allowing for selective, stepwise functionalization.
Safety and Handling
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GHS Hazard Classification (Aggregated from ECHA notifications):
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Hazard Statements:
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H302: Harmful if swallowed.
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H315: Causes skin irritation.
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H319: Causes serious eye irritation.
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H335: May cause respiratory irritation.
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Signal Word: Warning
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Pictogram: GHS07 (Exclamation Mark) - Irritant
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Precautionary Measures: Operations should be conducted in a fume hood or with adequate ventilation. Personnel must wear appropriate gloves, eye protection (goggles), and other protective clothing.
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Storage: Store in a tightly sealed container, protected from light. Keep away from oxidizers and heat sources.