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Chemical Structure| 24239-18-7

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Product Details of [ 24239-18-7 ]

CAS No. :24239-18-7
Formula : C14H10BrNS
M.W : 304.21
SMILES Code : BrCC1=CC=C(C2=NC3=CC=CC=C3S2)C=C1
MDL No. :MFCD16171064

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Application In Synthesis of [ 24239-18-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 24239-18-7 ]

[ 24239-18-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 16112-21-3 ]
  • [ 24239-18-7 ]
YieldReaction ConditionsOperation in experiment
94% With N-Bromosuccinimide; In tetrachloromethane; for 4h;Reflux; 2.71 g 2-p-Tolylbenzothiazole (12 mmol) and 2.14 g N-bromosuccinimide (NBS) (12 mmol) were dissolved in 50 ml of CCl4. The solution was heated under reflux for 4 h. The precipitated succinimide was filtered, and the solvent was evaporated from the solution. The remaining gray oil was recrystallized from ethanol. The obtained white crystalline powder was dried in vacuum (3.43 g, 94%). m.p. 132-133 C refPreviewPlaceHolder[27]. 1H NMR (300 MHz, CDCl3): δppm 8.08-8.13 (d, 3H), 7.92-7.99 (d, 1H), 7.53-7.76 (m, 3H), 7.42-7.50 (t, 1H), 4.55-4.62 (s, 2H). MS(M+): 302.9717 Anal. Calc. for C14H10BrNS: C, 55.45%; H, 3.30%; N, 4.62%. Found: C, 55.38%; H, 3.40%; N, 4.57%.
94% With N-Bromosuccinimide; In tetrachloromethane; for 4h;Reflux; 2-p-Tolylbenzothiazole (2.71 g, 12 mmol) and N-bromosuccinimide (NBS) (2.14 g, 12 mmol) were dissolved in 50 mL of CCl4. The solution was refluxed for 4 h. The precipitated succinimide was filtered, and the solvent was evaporated from the solution. The remaining gray oil was recrystallized from ethanol. The obtained white crystalline powder was dried in vacuum (3.43 g, yield 94%). Mp: 132-133 C. 1H NMR (CDCl3) δ 7.928-8.132 (m, 8H, Ar-H), 4.550-4.622 (s, 2H, -CH2-).
59% With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; (1) 2-(4-Bromomethylphenyl)-1,3-benzothiazole: Refluxed for 1 hour was 150 ml of a carbon tetrachloride solution which contained 10 g of <strong>[16112-21-3]2-(4-methylphenyl)-1,3-benzothiazole</strong>, 8.0 g of N-bromosuccinimide (NBS) and 0.2 g of benzoyl peroxide. After allowing the reaction mixture to cool down, the insoluble material was filtered off and the filtrate was concentrated under reduced pressure. The residue was recrystallized from ethanol to give 8.0 g of colorless crystals having a melting point of 128-130 C. (yield: 59%). IR νmaxKBr cm-1: 1475, 1220, 965, 755, 600.
With N-Bromosuccinimide;dibenzoyl peroxide; In tetrachloromethane; cyclohexane; Synthesis of 4-(benzothiazol-2-yl) bromomethylbenzene To a solution of 45 g (0.2 mol) of 4-(benzothiazol-2-yl) toluene in 1000 ml of dry carbon tetrachloride were added 35.6 g (0.2 mol) of N-bromosuccinimide and a catalytic amount of benzoyl peroxide. The mixture was refluxed for 12 hours, and then allowed to cool down to room temperature. The precipitated succinimide was filtered off and the filtrate evaporated to dryness in vacuo, whereupon 55 g of crude crystals were obtained. Recrystallization from 1500 ml of cyclohexane gave 41 g of purified 4-(benzothiazol-2-yl) bromomethylbenzene as colorless flakes.
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 9h;Reflux; <strong>[16112-21-3]2-(p-tolyl)benzothiazole</strong>(3.4 g, 15. 0 mmol), NBS (2.7 g, 15.0 mmol) and catalytic amount of benzoylperoxide (36 mg, 1 mol%) were dissolved in CCl4 (50 mL). The mixture washeated to reflux for 9 hours. The reaction was quenched by Na2SO3solution and extracted by CCl4 twice. Collected organic layers werewashed by brine, dried over Na2SO4 and concentrated togive the crude, which was recrystallized from hot EtOH to give the light purplesolid. NMR showed mono-brominated and dibrominated products were in a molarratio of 6:1. (3.2 g, 70% yield)LC-MS (ESI): [M+1]+ = 304.00, tR= 3.50 min. 1H NMR (400 MHz, CDCl3)δ 8.10-8.04 (m, 3H), 7.92-7.88 (m, 1H), 7.53-7.47 (m, 3H), 7.43-7.35 (m, 1H),4.52 (s, 1H).
8 g With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 12h;Reflux; Inert atmosphere; Schlenk technique; A mixture of compound 1 (9 g, 40 mmol), NBS (7.12 g, 40 mmol), and azodiisobutyronitrile (0.65 g) was refluxed in anhydrous CCl4 for 12 h. The mixture was cooled to room temperature, concentrated in vacuo, and the residue crystallized from cyclohexane yielding 8 g 1b as white solid.
With N-Bromosuccinimide; In tetrachloromethane; The solution of 1a (4.5 g, 15 mmol) in anhydrous CHCl3 (50 mL) was added dropwise to a solution (40 mL anhydrous CHCl3) of hexamethylenetetramine (2.1 g, 15 mmol). The mixture was refluxed for 5 h with vigorous stirring. The resulting precipitate was washed several times with deionized water and added to a mixture of ethanol and concentrated HCl (4:1, 100 mL). The resulting solution was kept stirring at 70 oC for 12 h and then allowed to stand at room temperature overnight. An HCl salt was obtained by filtration, washed with 10% KHCO3 (50 mL) and extracted into CHCl3 (50 mL). The organic layer was dried over anhydrous MgSO4. The solvent was removed in vacuo to give the primary amine 1b as a yellow solid (3.06 g, 85%). A mixture of 1b (1.8 g, 7.5 mmol) and paraformaldehyde (0.6 g, 19.5 mmol) in 20 mL CH2Cl2 was stirred for 5 h and treated dropwise with 2.25 mL (31 mmol) of SOCl2. After 1.5 h, the solvent and unreacted SOCl2 were removed under vacuum to give the product 1c. The generated solid was added to the THF solution of [(μ-LiS)2Fe2(CO)6], freshly prepared by the reaction of super hydride LiEt3BH (1 mol L-1 solution in THF, 8 mL) and [(μ-S)2-{Fe(CO)3}2] (2) (1.38 g, 4 mmol in 30 mL THF). The mixture was stirred for 2 h at -78 oC and then 1 h at room temperature. The solvent was removed on a rotary evaporator. The crude product was purified by column chromatography (silica, 10% dichloromethane in hexane as eluent) to give complex 4 (1.77 g, 72%) as a red solid.

  • 2
  • [ 16112-21-3 ]
  • [ 24239-18-7 ]
  • C14H9Br2NS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 9h;Reflux; <strong>[16112-21-3]2-(p-tolyl)benzothiazole</strong> (3.4 g, 15.0 mmol), NBS (2.7 g, 15.0 mmol) and catalytic amount of benzoyl peroxide (36 mg, 1 mol %) were dissolved in CCl4 (50 mL). The mixture was heated to reflux for 9 hours. The reaction was quenched by Na2SO3 solution and extracted by CCl4 twice. Collected organic layers were washed by brine, dried over Na2SO4 and concentrated to give the crude, which was recrystallized from hot EtOH to give the light purple solid. NMR showed mono-brominated and dibrominated products were in a molar ratio of 6:1. (3.2 g, 70% yield) LC-MS (ESI): [M+1]+=304.00, tR=3.50 min. 1H NMR (400 MHz, CDCl3) δ 8.10-8.04 (m, 3H), 7.92-7.88 (m, 1H), 7.53-7.47 (m, 3H), 7.43-7.35 (m, 1H), 4.52 (s, 1H).
 

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