580-13-2 Usage
Description
2-Bromonaphthalene is an organic compound with the chemical formula C10H6Br, featuring a naphthalene ring with a bromine atom attached at the 2nd position. It is a white or pale yellow powder and is known for its chemical and physical properties that make it suitable for various applications.
Uses
Used in Pharmaceutical Industry:
2-Bromonaphthalene is used as a raw material for the preparation of biaryls through the Suzuki cross-coupling reaction, which is a significant method in the synthesis of various pharmaceutical compounds. The versatility of this reaction allows for the creation of a wide range of biaryl-based drugs with potential therapeutic applications.
Used in Dye Industry:
In the dye industry, 2-bromonaphthalene plays a vital role in the preparation of dyes. Its unique chemical structure contributes to the development of dyes with specific color properties and stability, making it an essential component in the formulation of various dye products.
Used in Research and Development:
2-Bromonaphthalene is also utilized in research to study potential tumorigenicity. Its chemical properties and interactions with biological systems provide valuable insights into the development of cancer and the design of new cancer therapeutics.
General Description:
The reaction of 2-bromonaphthalene with cuprous cyanide in N-methylpyrrolidone has been investigated, providing insights into its chemical reactivity and potential applications. Additionally, the nanosecond time-resolved resonance Raman spectra of the T1→Tn transition of 2-bromonaphthalene in methanol solvent has been studied, further enhancing our understanding of its properties and behavior in different environments.
Synthesis Reference(s)
The Journal of Organic Chemistry, 32, p. 1607, 1967 DOI: 10.1021/jo01280a069Tetrahedron Letters, 26, p. 5939, 1985 DOI: 10.1016/S0040-4039(00)98266-2
Purification Methods
Purify 2-bromonaphthalene by fractional elution from a chromatographic column of activated alumina. Crystallise it from EtOH. [Beilstein 5 IV 1667.]
Check Digit Verification of cas no
The CAS Registry Mumber 580-13-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,8 and 0 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 580-13:
(5*5)+(4*8)+(3*0)+(2*1)+(1*3)=62
62 % 10 = 2
So 580-13-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H7Br/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H
580-13-2Relevant articles and documents
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Newman,Wise
, p. 2847 (1941)
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Fisher,Clark
, p. 251 (1939)
Direct bromodeboronation of arylboronic acids with CuBr2 in water
Tang, Yan-Ling,Xia, Xian-Song,Gao, Jin-Chun,Li, Min-Xin,Mao, Ze-Wei
supporting information, (2021/01/05)
An efficient and practical method has been developed for the preparation of aryl bromides via the direct bromodeboronation of arylboronic acids with CuBr2 in water. This strategy provides several advantages, such as being ligand-free, base-free, high yielding, and functional group tolerant.
Acceptorless Dehydrogenation of Hydrocarbons by Noble-Metal-Free Hybrid Catalyst System
Fuse, Hiromu,Kojima, Masahiro,Mitsunuma, Harunobu,Kanai, Motomu
supporting information, p. 2042 - 2045 (2018/04/16)
A hybrid catalysis that comprises an acridinium photoredox catalyst, a thiophosphate organocatalyst, and a nickel catalyst-enabled acceptorless dehydrogenation of hydrocarbons is reported. The cationic nickel complex played a critical role in the reactivity. This is the first example of acceptorless dehydrogenation of hydrocarbons by base metal catalysis under mild reaction conditions of visible light irradiation at room temperature.
A mild and ligand-free Ni-catalyzed silylation via C-OMe cleavage
Zarate, Cayetana,Nakajima, Masaki,Martin, Ruben
, p. 1191 - 1197 (2017/05/16)
Metal-catalyzed transformations that forge carbon-heteroatom bonds are of central importance in organic synthesis. Despite the formidable potential of aryl methyl ethers as coupling partners, the scarcity of metal-catalyzed C-heteroatom bond formations via C-OMe cleavage is striking, with isolated precedents requiring specialized, yet expensive, ligands, high temperatures, and π-extended backbones. We report an unprecedented catalytic ipso-silylation of aryl methyl ethers under mild conditions and without recourse to external ligands. The method is distinguished by its wide scope, which includes the use of benzyl methyl ethers, vinyl methyl ethers, and unbiased anisóle derivatives, thus representing a significant step forward for designing new C-heteroatom bond formations via C-OMe scission. Applications of this transformation in orthogonal silylation techniques as well as in further derivatizations are also described. Preliminary mechanistic experiments suggest the intermediacy of Ni(0)-ate complexes, leaving some doubt that a canonical catalytic cycle consisting of an initial oxidative addition of the C-OMe bond to Ni(0) species comes into play.
