6-BROMOSACCHARINE

6-BROMOSACCHARINE Property

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

6-BROMOSACCHARINE Chemical Properties,Usage,Production

Synthesis

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