5-broMo-3-fluorobenzene-1,2-diol
- Product Name
- 5-broMo-3-fluorobenzene-1,2-diol
- CAS No.
- 876861-29-9
- Chemical Name
- 5-broMo-3-fluorobenzene-1,2-diol
- Synonyms
- 1,10-Phenanthroline-5,8-dione;5-broMo-3-fluorobenzene-1,2-diol;1,2-Benzenediol, 5-bromo-3-fluoro-
- CBNumber
- CB62595423
- Molecular Formula
- C6H4BrFO2
- Formula Weight
- 207
- MOL File
- 876861-29-9.mol
5-broMo-3-fluorobenzene-1,2-diol Property
- Boiling point:
- 263.2±35.0 °C(Predicted)
- Density
- 1.940±0.06 g/cm3(Predicted)
- storage temp.
- Inert atmosphere,Room Temperature
- pka
- 7.84±0.15(Predicted)
- Appearance
- White to off-white Solid
Safety
- HS Code
- 2908190090
N-Bromosuccinimide Price
- Product number
- B688745
- Product name
- 5-Bromo-3-fluorobenzene-1,2-diol
- Packaging
- 100mg
- Price
- $85
- Updated
- 2021/12/16
- Product number
- B688745
- Product name
- 5-Bromo-3-fluorobenzene-1,2-diol
- Packaging
- 5g
- Price
- $1375
- Updated
- 2021/12/16
- Product number
- CS-0060186
- Product name
- 5-Bromo-3-fluorobenzene-1,2-diol
- Packaging
- 5g
- Price
- $750
- Updated
- 2021/12/16
- Product number
- 096614
- Product name
- 5-Bromo-3-fluorobenzene-1,2-diol
- Purity
- 95+%
- Packaging
- 1g
- Price
- $924
- Updated
- 2021/12/16
- Product number
- PC201341
- Product name
- 5-Bromo-3-fluorobenzene-1,2-diol
- Purity
- 95+%
- Packaging
- 100mg
- Price
- $89
- Updated
- 2021/12/16
5-broMo-3-fluorobenzene-1,2-diol Chemical Properties,Usage,Production
Uses
5-Bromo-3-fluorobenzene-1,2-diol is used as a reagent in the synthesis of N-(hydroxy(pyrrolidinyl)propanyl)pyrrolidinecarboxamide derivatives as glucosylceramide synthase inhibitors.5-Bromo-3-fluorobenzene-1,2-diol is also used in the preparation of 5,5-disubstituted-2-iminopyrrolidine derivatives as thrombin receptor antagonists.
Synthesis
251300-28-4
876861-29-9
General procedure for the synthesis of 5-bromo-3-fluoro-2-hydroxybenzene-1,2-diol from 5-bromo-3-fluoro-2-hydroxybenzaldehyde: Water was added slowly and dropwise to a solution of 5-bromo-3-fluoro-2-hydroxybenzaldehyde (40 g, 183 mmol) in tetrahydrofuran (THF, 260 mL). Sodium hydroxide (NaOH) solution (0.05N, 720 mL, 37 mmol) was added at 0 °C, followed by 30% hydrogen peroxide (H2O2) solution (90 mL). The reaction mixture was stirred at room temperature for 2 hours, then a second portion of 30% hydrogen peroxide (90 mL) was added. After continued stirring for 4 hours, the mixture was cooled to 0°C and washed with cold water. The pH was adjusted to 10-11 by adding sodium hydroxide solution (2N, 112 mL) and stirring was continued for 0.5 h. The reaction was subsequently quenched with concentrated hydrochloric acid (HCl). The pH was adjusted to 2-3 with hydrochloric acid at 0 °C. The reaction mixture was extracted with dichloromethane (250 mL x 3), the organic phases were combined and washed with brine (300 mL x 2), dried over anhydrous sodium sulfate (Na2SO4), and concentrated to give 5-bromo-3-fluorobenzene-1,2-diol (37 g, 98% yield) as a yellow oil. lc-MS (m/z): 205 [ M-H]-.
References
[1] Patent: WO2015/42397, 2015, A1. Location in patent: Paragraph 000236
[2] Patent: EP1780192, 2007, A1. Location in patent: Page/Page column 11
[3] Patent: WO2017/176960, 2017, A1. Location in patent: Paragraph 00730
[4] Patent: WO2015/65937, 2015, A1. Location in patent: Paragraph 000213
[5] Patent: WO2016/145153, 2016, A1. Location in patent: Paragraph 000179
5-broMo-3-fluorobenzene-1,2-diol Preparation Products And Raw materials
Raw materials
Preparation Products
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