5-BroMo-6-chloropicolinonitrile
Application- Product Name
- 5-BroMo-6-chloropicolinonitrile
- CAS No.
- 1256823-65-0
- Chemical Name
- 5-BroMo-6-chloropicolinonitrile
- Synonyms
- 5-BroMo-6-chloropicolinonitrile;5-bromo-6-chloropyridine-2-carbonitrile;2-Pyridinecarbonitrile, 5-bromo-6-chloro-
- CBNumber
- CB22732439
- Molecular Formula
- C6H2BrClN2
- Formula Weight
- 217.45
- MOL File
- 1256823-65-0.mol
5-BroMo-6-chloropicolinonitrile Property
- Boiling point:
- 284.8±35.0 °C(Predicted)
- Density
- 1.85±0.1 g/cm3(Predicted)
- storage temp.
- under inert gas (nitrogen or Argon) at 2-8°C
- pka
- -6.54±0.10(Predicted)
- Appearance
- Off-white to light brown Solid
- InChI
- InChI=1S/C6H2BrClN2/c7-5-2-1-4(3-9)10-6(5)8/h1-2H
- InChIKey
- GKCQPDVYUJLEIJ-UHFFFAOYSA-N
- SMILES
- C1(C#N)=NC(Cl)=C(Br)C=C1
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
- 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.
N-Bromosuccinimide Price
- Product number
- B821198
- Product name
- 5-Bromo-6-chloropicolinonitrile
- Packaging
- 10mg
- Price
- $45
- Updated
- 2021/12/16
- Product number
- 4052AQ
- Product name
- 5-Bromo-6-Chloropicolinonitrile
- Packaging
- 1g
- Price
- $422
- Updated
- 2021/12/16
- Product number
- A233615
- Product name
- 5-Bromo-6-chloropicolinonitrile
- Purity
- 97%
- Packaging
- 100mg
- Price
- $72
- Updated
- 2021/12/16
- Product number
- A233615
- Product name
- 5-Bromo-6-chloropicolinonitrile
- Purity
- 97%
- Packaging
- 250mg
- Price
- $72
- Updated
- 2021/12/16
- Product number
- A233615
- Product name
- 5-Bromo-6-chloropicolinonitrile
- Purity
- 97%
- Packaging
- 1g
- Price
- $185
- Updated
- 2021/12/16
5-BroMo-6-chloropicolinonitrile Chemical Properties,Usage,Production
Application
5-Bromo-6-chloropicolinonitrile can be used as a pharmaceutical synthesis intermediate, and can be used in laboratory research and development as well as in chemical and pharmaceutical synthesis processes.
Synthesis
7677-24-9
1373126-39-6
1256823-65-0
Step 2. Synthesis of 5-bromo-6-chloropyridine-2-carbonitrile (C28): Trimethylmethylsilyl cyanide (19 mL, 0.15 mol) was slowly added with stirring to a solution of acetonitrile (400 mL) containing 3-bromo-2-chloropyridine 1-oxide (C27) (31.6 g, 0.152 mol) and triethylamine (63.4 mL, 0.46 mol). . The reaction mixture was heated to 50°C and maintained for 2 hours. Subsequently cooled to room temperature, trimethylmethylsilyl cyanide (19 mL) was added again and the reaction mixture was continued to be heated at 50°C for 1.5 hours. Finally, a third portion of trimethylsilyl cyanide (28.5 mL, 0.23 mol) was added and the reaction mixture was heated to reflux for 3 days. After completion of the reaction, the reaction mixture was diluted with dichloromethane (2 L), washed sequentially with saturated aqueous sodium bicarbonate (800 mL) and water (1 L), and the organic phase was dried with magnesium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography (elution gradient: 20% to 25% ethyl acetate/heptane) afforded 5-bromo-6-chloro-2-pyridinecarbonitrile as a yellow solid in 14.92 g (68.6 mmol, 45%) yield. The reaction was carried out using the acylating agent dimethylcarbamoyl chloride: a solution of dimethylcarbamoyl chloride (12.9 mL, 0.14 mol) in dichloromethane (23 mL) was slowly added dropwise to a stirred solution of 3-bromo-2-chloropyridine 1-oxide (C27) (11.23 g, 53.9 mmol) and trimethylsilyl cyanide (17.5 mL, 0.14 mol) in in a solution of dichloromethane (200 mL). The reaction mixture was heated and refluxed for 3 days, and after completion of the reaction, it was diluted with dichloromethane (450 mL), washed sequentially with saturated aqueous sodium bicarbonate (2×200 mL) and water (200 mL), and the organic phase was dried with magnesium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography (elution gradient: 15% to 20% ethyl acetate/heptane) afforded 5-bromo-6-chloropyridine-2-carbonitrile as an off-white solid containing dimethylcarbamoyl cyanide (12.73 g, 100%) as impurity.
References
[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 8, p. 2906 - 2911
[2] Patent: US2012/252758, 2012, A1. Location in patent: Page/Page column 28
5-BroMo-6-chloropicolinonitrile Preparation Products And Raw materials
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