Category: 18791-79-2

Heterocyclics. XIII. Synthesis of substituted bromothiophenes was written by Fournari, Pierre;Guilard, Roger;Person, Maurice. And the article was included in Bulletin de la Societe Chimique de France in 1967.Category: bromides-buliding-blocks This article mentions the following:

Bromothiophenecarboxaldehydes of the general formula I are prepared and treated with aryl ketones to give compounds of the general formula II. Thus, 66 g. 2,3-dibromothiophene is treated with 0.273 mole BuLi and the organic Li compound obtained is treated with 30 g. HCONMe2 to give 13.5 g. 3-bromo-2-formylthiophene (III), b12 109-12°; thiosemicarbazone m. 246°; oxime m. 159°. Similarly prepared are (b.p./mm., m.p., m.p. thiosemicarbazone, and m.p. oxime given): I (R = R3 = H, R1 = CHO, R2 = Br), 118-20°/13, -, 221°, 104°; I (R = R1 = CHO, R2 = Br, R3 = H), 158-60°/13, 117-18°, -, -. I [R = R2 = R3 = H, R1 = CH(OEt)2] is treated with 0.13 mole BuLi and a solution of 12 g. Br is added to give 5 g. I (R = Br, R1 = CHO, R2 = R3 = H), m. 34° (hexane); thiosemicarbazone m. 235°, oxime m. 86°. Similarly prepared are the following I (R2 = H) (R, R1, R3, b.p./mm., m.p., m.p. thiosemicarbazone, and m.p. oxime given): H, CHO, Br, 114-16°/17-18, -, 180°, 91°; Br, CHO, Br, 122-35°/12-14, 45-6° (ligroine), 266°, 136°. The following I (R1 = H) are prepared according to known methods (R, R2, R3, b.p./mm., m.p., m.p. thiosemicarbazone, and m.p. oxime given): CHO, Br, H, -, 45-6°, 216°, 174°; CHO, H, Br, 112-14°/14, -, 173-4°, 152-4°. A mixture of 0.01 mole 0-HOC6H4Ac, 0.01 mole III, 1 ml. 5N NaOH, and 10 ml. EtOH is heated 2 hrs. at 60° to give 10% 0-hydroxyphenyl 2-(3-bromo-2-thienyl)vinyl ketone, m. 124°. Similarly prepared are the following II (R = R2 = H, R1 = Br) (Ar, m.p., and % yield given): 0-HOC6H4, 108°, 11; 2,5-HO(O2N)C6H3, 195°, 65. A mixture of 0.01 mole 5-bromo-2-acetylthiophene, 0.01 mole 2-formylthiophene, 3.2 ml. N NaOH, and 20 ml. EtOH is refrigerated 2 hrs. to give 20% II (R = R1 = R2 = H, Ar + 5-bromo-2-thienyl), m. 113°. Similarly prepared are the following II (R2 = H) (Ar, R, R1, m.p., and % yield given): 5-bromo-2-thienyl, H, Br, 135°, 33; 5-bromo-2-thienyl, Br, H, 144°, 40; 2-thienyl, Br, H, 100°, 60; 2-pyridyl, Br, H, 145°, 80; 2-pyridyl, H, Br, 136°, 70. 3-Bromo-2-cyanothiophene (m. 50°) and the following I are prepared according to the P. Reynaud-R. Delaby method for the preparation of 2-cyanothiophene (R, R1, R2, R3, b.p./mm., and m.p. given): CN, H, Br, H, -, 45° (ether-ligroine); CN, H, H, Br, 124°/34, -; Br, CN, H, H, 130°/22, -; H, CN, Br, H, -, 56 (ether-ligroine); H, CN, H, Br, -, 33° (aqueous alc.); Br, CN, H, Br, -, 76° (aqueous alc.). The bromocyanothiophenes (0.01 mole) are treated with 10 ml. H2O2 at 50° in the presence of 4 ml. 25% KOH to give 4-bromo-2-thiophenecarboxamide, m. 153-4°, and the following I (R, R1, R2, R3, and m.p. given): CONH2, H, H, Br, 164°; Br, CONH2, H, H, 142°; H, CONH2, Br, H, 146°; H, CONH2, H, Br, 146°; Br, CONH2, H, Br, 140-1°; CONH2, Br, H, H, 103°. 5-Bromo-3-formylthiophene (0.005 mole) is treated with 800 mg. KMnO4 to give 0.6 g. 5-bromo-3-thiophenecarboxylic acid, m. 139° (aqueous alc.). Similarly prepared are the following I (R, R1, R2, R3, and m.p. given): CO2H, Br, H, H, 197-8°; CO2H, H, Br, H, 123°; CO2H, H, H, Br, 142°; Br, CO2H, H, H, 180°; H, CO2H, Br, H, 159°; H, CO2H, H, Br, 139°; Br, CO2H, H, Br, 178°. N.M.R. data are given. In the experiment, the researchers used many compounds, for example, 5-Bromothiophene-3-carbaldehyde (cas: 18791-79-2Category: bromides-buliding-blocks).

5-Bromothiophene-3-carbaldehyde (cas: 18791-79-2) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Desulfonylative Coupling of Alkylsulfones with gem-Difluoroalkenes by Visible-Light Photoredox Catalysis was written by Nambo, Masakazu;Ghosh, Koushik;Yim, Jacky C.-H.;Tahara, Yasuyo;Inai, Naoto;Yanai, Takeshi;Crudden, Cathleen M.. And the article was included in ACS Catalysis in 2022.HPLC of Formula: 18791-79-2 This article mentions the following:

The desulfonylative radical addition of tertiary alkyl groups I [R¹ = 2-phenylethyl, 1,3-dioxolan-2-ylmethyl, prop-2-en-1-yl, etc. R² = Me, 3-chloropropyl, 2-(tert-butoxy)-2-oxoethyl, etc.; R¹ = R² = -(CH₂)₅-, -(CH₂)₂O(CH₂)₂-, 2,3-dihydro-1H-inden-2-ylidene; R³ = H, Me] to gem-difluoroalkenes F₂C=CHR⁴ (R⁴ = 4-(4-chlorophenyl)phenyl, naphthalen-2-yl, 1-benzothiophen-3-yl, etc.) by photoredox Ir-catalyst was described. This method exhibits broad substrate scope, affording structurally diverse (E)-fluoroalkene derivatives (R¹)(R²)R³CC(F)=CHR⁴ in a highly stereoselective manner. The resulting (E)-fluoroalkenes were converted into complex fused cyclic compounds e.g., II by intramol. cyclization reactions. Control experiments and theor. calculations are consistent with a single Ir catalyst playing the dual role of generating radical species from sulfones via single electron transfer and mediating Z/E isomerization via energy transfer. A subset of fluoroalkenes provided Z stereoisomers with <90% selectivity, but the same alkenes could also be obtained as E isomers (R¹)(R²)R³CC(F)=CHR⁴ (R¹ = 2-phenylethyl, R² = R³ = Me, R⁴ = m-OMe, m-Br, p-Me.) with high selectivity by taking advantage of a secondary Z to E photoisomerization. In the experiment, the researchers used many compounds, for example, 5-Bromothiophene-3-carbaldehyde (cas: 18791-79-2HPLC of Formula: 18791-79-2).

5-Bromothiophene-3-carbaldehyde (cas: 18791-79-2) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.HPLC of Formula: 18791-79-2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Studies of Substituents Impact on the Photophysical Properties of 8-Hydroxyquinoline Derivatives was written by Gao, Li-Bin;Kang, Wu-Kui;Yan, Shi-Hai;Yang, Chun-Peng. And the article was included in Heteroatom Chemistry in 2016.SDS of cas: 18791-79-2 This article mentions the following:

Five new 8-hydroxyquinoline derivatives L1-L5 were synthesized and characterized by different techniques, such as NMR, electrospray ionization mass spectra, elemental anal., UV-visible, and photoluminescence spectra. The structure of (E)-2-{2-[5-(phenylethynyl) thiophen-2-yl]ethenyl}quinolin-8-ol (L3) was confirmed by x-ray crystallog. In this structure, intermol. hydrogen bonds were found between OH hydrogen donors of one monomer and the oxygen atom of the next one. Photophys. studies show that different substitutes affect the absorption wavelength and emission color. In the experiment, the researchers used many compounds, for example, 5-Bromothiophene-3-carbaldehyde (cas: 18791-79-2SDS of cas: 18791-79-2).

5-Bromothiophene-3-carbaldehyde (cas: 18791-79-2) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. SDS of cas: 18791-79-2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary