615-57-6 Usage
Description
2,4-Dibromoaniline is an organic compound with the chemical formula C6H4Br2NH2, characterized by its beige powder appearance. It is a derivative of aniline, where two hydrogen atoms on the benzene ring are replaced by bromine atoms at the 2nd and 4th positions. 2,4-Dibromoaniline is known for its versatile chemical properties, making it a valuable intermediate in the synthesis of various organic compounds.
Uses
Used in the Preparation of Glycopeptides and Targeted Bifunctional Degraders:
2,4-Dibromoaniline is used as a key intermediate for the synthesis of glycopeptides and targeted bifunctional degraders. These biomolecules have significant applications in the pharmaceutical industry, particularly in the development of drugs targeting specific biological pathways.
Used in the Synthesis of Acetylenic Amine:
2,4-Dibromoaniline serves as a starting material to synthesize acetylenic amine by reacting with trimethylsilylacetylene. The resulting acetylenic amine is then used as a ligand to prepare the bis-amido complex of Ti(IV), which has potential applications in catalysis and material science.
Used in Pd-Catalyzed Ortho-Selective Cross-Coupling Reactions:
As a substrate in the Pd-catalyzed ortho-selective cross-coupling reactions of dihaloarenes with Grignard reagents, 2,4-Dibromoaniline plays a crucial role in the formation of new carbon-carbon bonds. This reaction is widely used in the synthesis of complex organic molecules, including pharmaceuticals and natural products.
Used in the Preparation of Dialkyl-Substituted Aminoaryl Sulfides:
2,4-Dibromoaniline is a reactant in the preparation of dialkyl-substituted aminoaryl sulfides using a Grignard reagent. These compounds have potential applications in the development of new materials and pharmaceuticals.
Used as a Starting Material for Synthesizing Substituted 2-Mercapto Benzimidazoles:
2,4-Dibromoaniline is also used as a starting material to synthesize substituted 2-mercapto benzimidazoles, which are important building blocks in the synthesis of various heterocyclic compounds with potential applications in pharmaceuticals, agrochemicals, and other industries.
Purification Methods
Crystallise the aniline from aqueous EtOH. The picrate has m 124o. [Beilstein 12 H 655, 12 I 326, 12 II 356, 12 III 1471, 12 IV 1532.]
Check Digit Verification of cas no
The CAS Registry Mumber 615-57-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 5 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 615-57:
(5*6)+(4*1)+(3*5)+(2*5)+(1*7)=66
66 % 10 = 6
So 615-57-6 is a valid CAS Registry Number.
InChI:InChI=1/C6H5Br2N/c7-4-1-2-6(9)5(8)3-4/h1-3H,9H2
615-57-6Relevant articles and documents
A Practical Procedure for Regioselective Bromination of Anilines
Takahashi, Yusuke,Seki, Masahiko
, p. 1828 - 1832 (2021/04/15)
A highly practical procedure for the preparation of bromoanilines by using copper-catalyzed oxidative bromination has been developed. Treatment of free anilines with readily available NaBr and Na 2S 2O 8in the presence of a catalytic amount of CuSO 4·5H 2O enabled regioselective bromination.
NOVEL TRICYCLIC COMPOUND AS IRAK4 INHIBITOR
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Paragraph 0046-0048, (2021/10/02)
The present invention relates to a pharmaceutical composition for preventing or treating autoimmune diseases or tumors, containing, as an active ingredient, a tricyclic compound represented by the following Chemical Formula 1 or a pharmaceutically acceptable salt thereof, and a health food composition for preventing or alleviating autoimmune diseases or tumors, containing the tricyclic compound as an active ingredient. The tricyclic compound represented by Chemical Formula 1 of the present invention has an excellent inhibitory activity against IRAK4, and thus can be usefully used for the prevention, treatment, or alleviation of autoimmune diseases or tumors.
Visible-light-promoted oxidative halogenation of (hetero)arenes
Jiang, Xuefeng,Li, Yiming,Lu, Lingling
supporting information, p. 5989 - 5994 (2020/10/18)
Organic halides are critical building blocks that participate in various cross-coupling reactions. Furthermore, they widely exist as natural products and artificial molecules in drugs with important physiological activities. Although halogenation has been well studied, to the best of our knowledge, studies focussing on sensitive systems (e.g.aryl amines) have not been reported. Herein, we describe a compatible oxidative halogenation of (hetero)arenes with air as the oxidant and halide ions as halide sources under ambient conditions (visible light, air, aqueous system, room temperature, and normal pressure). Moreover, this protocol is practically feasible for gram-scale synthesis, showing potential for industrial application.
