2-Chloro-5-Iodobenzotrifluoride: Properties & Lab Use FAQ
2-Chloro-5-Iodobenzotrifluoride: Properties & Lab Use FAQ
2-Chloro-5-iodobenzotrifluoride is a halogenated aromatic building block bearing three distinct reactive handles — a chloro group, an iodo group, and a trifluoromethyl substituent — making it a versatile intermediate for cross-coupling reactions, agrochemical synthesis, and pharmaceutical research.
- Chemical Name
- 2-Chloro-5-iodobenzotrifluoride
- CAS Number
- 179944-38-8
- Molecular Formula
- C7H3ClF3I
- Molecular Weight
- 322.45 g/mol
- Key Functional Groups
- Aryl chloride, aryl iodide, trifluoromethyl (CF3)
- Primary Applications
- Cross-coupling reactions (Suzuki, Sonogashira, Buchwald-Hartwig), medicinal and agrochemical synthesis
- Aladdin SKU
- C133091
Chemical Identity and Structure
2-Chloro-5-iodobenzotrifluoride (CAS 179944-38-8, SKU C133091) is an aromatic compound in which a benzene ring carries a chloro substituent at the 2-position, an iodo substituent at the 5-position, and a trifluoromethyl (CF3) group at the 1-position. Its molecular formula is C7H3ClF3I with a molecular weight of approximately 322.45 g/mol.
The coexistence of three electronegative substituents — Cl, I, and CF3 — renders the ring electron-poor, which influences regioselectivity in nucleophilic and metal-catalyzed reactions. The trifluoromethyl group is strongly electron-withdrawing by induction and is metabolically stable, a property highly valued in drug design and agrochemistry.
Reactivity and Synthetic Applications
The aryl iodide functionality in 2-Chloro-5-iodobenzotrifluoride is highly reactive toward transition-metal-catalyzed cross-coupling reactions. Because C–I bonds are weaker and more easily oxidatively added than C–Cl bonds, the iodo position undergoes preferential reactivity in palladium- and copper-catalyzed transformations such as Suzuki-Miyaura, Sonogashira, Negishi, and Buchwald-Hartwig couplings under mild conditions.
The remaining aryl chloride can subsequently serve as a second handle for orthogonal coupling steps or nucleophilic aromatic substitution (SNAr), enabling sequential derivatization of the scaffold. This chemoselectivity makes the compound a valuable bifunctional building block for multi-step synthesis of complex fluorinated targets, including pharmaceutical candidates, agrochemical intermediates, and materials science precursors.
Handling, Storage, and Safety
As with most halogenated aromatic compounds, 2-Chloro-5-iodobenzotrifluoride should be handled with appropriate personal protective equipment including nitrile gloves, safety glasses, and a laboratory coat. Operations generating vapor or aerosol should be conducted in a well-ventilated fume hood.
The compound should be stored in a tightly sealed container at room temperature (15–25 °C), protected from light and moisture to prevent degradation or hydrolysis of sensitive bonds. Compatibility with standard laboratory storage conditions for halogenated aromatics is expected; however, users should always consult the product-specific Safety Data Sheet (SDS) available from Aladdin Scientific before use.
Note: Specific GHS hazard classifications, flash point, and LD50 values should be verified against the current SDS for SKU C133091.
Purity, Quality, and Analytical Characterization
Aladdin Scientific supplies 2-Chloro-5-iodobenzotrifluoride (C133091) as a research-grade reagent. Purity is typically verified by gas chromatography (GC) or high-performance liquid chromatography (HPLC). Structural confirmation is achieved through 1H NMR, 19F NMR, and mass spectrometry.
For the most current purity specifications, lot-specific certificates of analysis (CoA) are available upon request or via the Aladdin Scientific product page. Researchers requiring higher purity grades for sensitive assays should contact Aladdin's technical support team to discuss available options.
Ordering and Availability
2-Chloro-5-iodobenzotrifluoride is catalogued at Aladdin Scientific under SKU C133091. It is available in standard pack sizes suitable for research-scale use. To place an order, visit the product page on the Aladdin Scientific website, or contact your regional sales representative.
For bulk quantities, custom pack sizes, or pricing inquiries, please reach out to Aladdin's sales or procurement team directly. Volume pricing may be available for larger orders. Certificate of Analysis documents can be requested for any specific lot to support GMP-adjacent documentation requirements.
Frequently asked questions
What makes the iodo group in 2-Chloro-5-iodobenzotrifluoride more reactive than the chloro group in cross-coupling reactions?
The C–I bond has lower bond dissociation energy compared to the C–Cl bond, making oxidative addition to palladium(0) or other transition-metal catalysts significantly faster at the iodo position. This kinetic preference allows chemists to selectively functionalize the aryl iodide site first while leaving the aryl chloride intact for a subsequent orthogonal transformation.
How should I store 2-Chloro-5-iodobenzotrifluoride (C133091) to maintain stability?
Store the compound in a tightly sealed container at room temperature (15–25 °C), away from light and moisture. Halogenated aromatics bearing iodo substituents can undergo slow decomposition upon prolonged exposure to light or air; refrigerated storage may extend shelf life for long-term stock. Always consult the product SDS for specific storage requirements before handling.
In which types of reactions is 2-Chloro-5-iodobenzotrifluoride commonly used as a building block?
This compound is widely used in palladium-catalyzed cross-coupling reactions including Suzuki-Miyaura (with arylboronic acids), Sonogashira (with terminal alkynes), Negishi (with organozinc reagents), and Buchwald-Hartwig amination (with amines). Its electron-withdrawing CF3 group and dual halide handles also make it useful in nucleophilic aromatic substitution and as an intermediate in the synthesis of fluorinated pharmaceuticals and agrochemicals.
What analytical methods confirm the identity and purity of C133091?
Identity is typically confirmed by 1H NMR, 19F NMR, and mass spectrometry, which together verify the regiochemistry of the three substituents and the molecular mass. Purity is routinely assessed by GC or HPLC. A lot-specific Certificate of Analysis (CoA) detailing these results is available from Aladdin Scientific upon request.
Can 2-Chloro-5-iodobenzotrifluoride be used in both Pd- and Cu-catalyzed reactions?
Yes. The aryl iodide moiety is reactive under both palladium-catalyzed and copper-catalyzed conditions. For example, it can participate in copper-catalyzed Ullmann-type couplings and Chan-Lam reactions at the C–I bond, in addition to the well-established palladium-catalyzed cross-couplings. The choice of metal catalyst and conditions determines which halide reacts preferentially.
References
- Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (General reference for aryl halide reactivity and cross-coupling reactions.)
- Johansson Seechurn, C. C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Palladium-Catalyzed Cross-Coupling: A Historical Contextual Perspective to the 2010 Nobel Prize. Angew. Chem. Int. Ed. 2012, 51, 5062–5085. doi:10.1002/anie.201107017
- Aladdin Scientific. Product Page: 2-Chloro-5-iodobenzotrifluoride, SKU C133091. https://www.aladdin-e.com (accessed 2024).
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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