(2-bromo-5-chloropyridin-3-yl)methanol
- Product Name
- (2-bromo-5-chloropyridin-3-yl)methanol
- CAS No.
- 1227585-65-0
- Chemical Name
- (2-bromo-5-chloropyridin-3-yl)methanol
- Synonyms
- (2-bromo-5-chloro-3-pyridinyl)methanol;EOS-60900;Atozepam impurity 17;Atogepant Impurity 26;(2-Bromo-5-chloro-3-pyridyl)methanol;(2-bromo-5-chloropyridin-3-yl)methanol
- CBNumber
- CB33042325
- Molecular Formula
- C6H5BrClNO
- Formula Weight
- 222.47
- MOL File
- 1227585-65-0.mol
(2-bromo-5-chloropyridin-3-yl)methanol Property
- Boiling point:
- 318.4±37.0 °C(Predicted)
- Density
- 1.785±0.06 g/cm3(Predicted)
- storage temp.
- under inert gas (nitrogen or Argon) at 2-8°C
- pka
- 12.59±0.10(Predicted)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H332Harmful if inhaled
H335May cause respiratory irritation
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P310Immediately call a POISON CENTER or doctor/physician.
N-Bromosuccinimide Price
- Product number
- B821115
- Product name
- (2-Bromo-5-chloropyridin-3-yl)methanol
- Packaging
- 2.5g
- Price
- $2250
- Updated
- 2021/12/16
- Product number
- A103428
- Product name
- (2-Bromo-5-chloropyridin-3-yl)methanol
- Purity
- 98%
- Packaging
- 100mg
- Price
- $87
- Updated
- 2021/12/16
- Product number
- A103428
- Product name
- (2-Bromo-5-chloropyridin-3-yl)methanol
- Purity
- 98%
- Packaging
- 250mg
- Price
- $145
- Updated
- 2021/12/16
- Product number
- 30423
- Product name
- (2-Bromo-5-chloropyridin-3-yl)methanol
- Purity
- 95%
- Packaging
- 500mg
- Price
- $154
- Updated
- 2021/12/16
- Product number
- CM248348
- Product name
- (2-Bromo-5-chloropyridin-3-yl)methanol
- Purity
- 98%
- Packaging
- 1g
- Price
- $281
- Updated
- 2021/12/16
(2-bromo-5-chloropyridin-3-yl)methanol Chemical Properties,Usage,Production
Uses
(2-Bromo-5-chloropyridin-3-yl)methanol is used in preparation of Spiro[indene-pyrrolopyridine] compounds as AM2 receptor inhibitors.
Synthesis
137628-17-2
1227585-65-0
General procedure for the synthesis of (2-bromo-5-chloropyridin-3-yl)methanol from 2,3-dibromo-5-chloropyridine: To a solution of 2,3-dibromo-5-chloropyridine (60 g, 221 mmol) in tetrahydrofuran (THF, 500 mL) was slowly added a THF solution of isopropylmagnesium chloride lithium chloride (1.3 M, 185 mL) at -40 °C. The reaction temperature was maintained at -40 °C and after stirring for 30 min, N,N-dimethylformamide (DMF, 50 mL) was added. The reaction mixture was gradually warmed to room temperature and stirring was continued for 30 min. The reaction was quenched with 1N hydrochloric acid (400 mL) and methyl tert-butyl ether (MTBE, 200 mL) was added. The organic layer was separated and washed twice with 5% aqueous sodium bicarbonate (200 mL). The solvent was removed by concentration under reduced pressure at 50 °C. The resulting aldehyde intermediate solid was dissolved in methanol (400 mL) and cooled to 5°C in an ice bath. Sodium borohydride (NaBH4, 3.6 g) was added slowly over 30 min, controlling the reaction temperature not to exceed room temperature. Stirring was continued for 30 minutes and then water (125 mL) was added. The reaction mixture was concentrated under reduced pressure to approximately 150 mL, with solids precipitating during the process. The suspension was stirred vigorously for 1 hour at room temperature and the solids were collected by filtration. The wet filter cake was dried in a vacuum oven at 60 °C overnight to afford the target product (2-bromo-5-chloropyridin-3-yl)methanol (45.6 g, 93% yield) as a white solid. The product was structurally confirmed by 1H NMR (CDCl3, 400 MHz) and 13C NMR (CDCl3, 100 MHz).
References
[1] Patent: US2016/130273, 2016, A1. Location in patent: Paragraph 0234; 0235
[2] Patent: WO2013/138413, 2013, A1
[3] Patent: WO2013/169348, 2013, A1
[4] Angewandte Chemie - International Edition, 2014, vol. 53, # 32, p. 8375 - 8378
[5] Angew. Chem., 2014, vol. 126, # 32, p. 8515 - 8518,4
(2-bromo-5-chloropyridin-3-yl)methanol Preparation Products And Raw materials
Raw materials
Preparation Products
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