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ChemicalBook--->CAS DataBase List--->62473-92-1

62473-92-1

62473-92-1 Structure

62473-92-1 Structure
IdentificationBack Directory
[Name]

6-BROMOSACCHARINE
[CAS]

62473-92-1
[Synonyms]

6-bromosaccharin
6-BROMOSACCHARINE
RARECHEM AM UH V180
6-Bromo-1,2-benzisothiazol-3-one 1,1-dioxide
6-Bromobenzo[d]isothiazol-3(2H)-one 1,1-dioxide
6-bromo-1,2-benzisothiazol-3(2H)-one 1,1-dioxide
1,2-Benzisothiazol-3(2H)-one, 6-bromo-, 1,1-dioxide
[Molecular Formula]

C7H4BrNO3S
[MDL Number]

MFCD03789731
[MOL File]

62473-92-1.mol
[Molecular Weight]

262.08
Chemical PropertiesBack Directory
[density ]

1.958±0.06 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,Room Temperature
[pka]

1.15±0.30(Predicted)
[Appearance]

White to light yellow Solid
[InChI]

InChI=1S/C7H4BrNO3S/c8-4-1-2-5-6(3-4)13(11,12)9-7(5)10/h1-3H,(H,9,10)
[InChIKey]

CNDPIUXFHSMKMG-UHFFFAOYSA-N
[SMILES]

S1(=O)(=O)C2=C(C=CC(Br)=C2)C(=O)N1
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H302-H335-H319
[Precautionary statements ]

P264-P270-P301+P312-P330-P501-P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
Spectrum DetailBack Directory
[Spectrum Detail]

6-BROMOSACCHARINE(62473-92-1)1HNMR
Hazard InformationBack Directory
[Synthesis]

Methyl 2-amino-4-bromobenzoate

135484-83-2

6-BROMOSACCHARINE

62473-92-1

Methyl 2-amino-4-bromobenzoate (4.5 g, 20 mmol) was stirred in 20% hydrochloric acid (30 mL) until completely dissolved. The solution was cooled to 0 °C, the reaction temperature was controlled not to exceed 5 °C, and a solution of sodium nitrite (1.4 g, 0.020 mol) in water (20 mL) was added dropwise. The mixture was stirred at 0°C for 45 min. Meanwhile, sulfur dioxide was passed into a mixture of acetic acid (50 mL) and water (5 mL) to saturation at 0 °C, followed by the addition of copper (I) chloride (2.0 g, 0.020 mol). The mixture was cooled to 0 °C and the diazonium salt solution was added dropwise over 30 min with vigorous stirring. The reaction mixture was stirred at 0 °C for 1 h. After stirring, the mixture was slowly warmed to room temperature and stirring was continued for 2 h. The mixture was then cooled to room temperature. The mixture was poured into ice water (250 mL) and extracted with EtOAc (3 x 50 mL). The organic phase was washed with saturated NaHCO3 solution and dried over anhydrous Na2SO4. The solvent was concentrated under reduced pressure to give an oily residue, which was dissolved in tetrahydrofuran (40 mL) and cooled to 0 °C. Cold (0°C) 28% ammonium hydroxide solution (40 mL) was added in batches and the reaction temperature was controlled to be below 10°C. The mixture was warmed to room temperature and stirred for 1 hour. The solvent was removed under reduced pressure and the residue was dissolved in saturated aqueous sodium bicarbonate solution (40 mL) and washed with ether (50 mL). The aqueous layer was acidified to pH 1 with concentrated hydrochloric acid, the precipitate was collected by filtration and dried under vacuum to give 6-bromo-1,1-dioxo-1,2-dihydro-1λ6-benzo[d]isothiazol-3-one (500 mg, 10% yield).1H NMR (400 MHz, DMSO) δ 8.44 (d, J=1.5, 1H), 8.04 (dd, J=8.1,1.5, 1H), 7.81 (d, J=8.1,1.5, 1H), 7.81 (d, J=8.1,1.5, 1.1.5, 1.1.5, 1H). 1H), 7.81 (d, J=8.0,1H).

[References]

[1] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 4, p. 949 - 961
[2] Patent: US2008/9524, 2008, A1. Location in patent: Page/Page column 410
[3] Patent: US2015/231142, 2015, A1. Location in patent: Paragraph 1267
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