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| | 2-Chloro-5-pyridineacetonitrile Basic information |
| Product Name: | 2-Chloro-5-pyridineacetonitrile | | Synonyms: | 2-CHLORO-5-PYRIDINEACETONITRILE;2-(6-CHLORO-3-PYRIDINYL)ACETONITRILE;2-CHLORO-5-(CYANOMETHYL)PYRIDINE;2-CHLOROPYRIDINE-5-ACETONITRILE;(6-CHLORO-PYRIDIN-3-YL)-ACETONITRILE;2-(6-chloropyridin-3-yl)acetonitrile;2-Chloro-5-pyridinea;6-Chloro-3-(cyanomethyl)pyridine | | CAS: | 39891-09-3 | | MF: | C7H5ClN2 | | MW: | 152.58 | | EINECS: | | | Product Categories: | Pyridines;Pyridine | | Mol File: | 39891-09-3.mol |  |
| | 2-Chloro-5-pyridineacetonitrile Chemical Properties |
| Melting point | 49-54°C | | Boiling point | 182 °C(Press: 1 Torr) | | density | 1.262±0.06 g/cm3(Predicted) | | Fp | >110℃ | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | pka | -1.02±0.10(Predicted) | | form | solid | | Appearance | Brown to reddish brown Solid | | InChI | InChI=1S/C7H5ClN2/c8-7-2-1-6(3-4-9)5-10-7/h1-2,5H,3H2 | | InChIKey | BLGUCBUETMYJTB-UHFFFAOYSA-N | | SMILES | C1=NC(Cl)=CC=C1CC#N | | CAS DataBase Reference | 39891-09-3(CAS DataBase Reference) |
| Hazard Codes | Xi,T,Xn | | Risk Statements | 22-37/38-41 | | Safety Statements | 26-39 | | RIDADR | UN 3439 6.1 / PGIII | | WGK Germany | 3 | | HazardClass | IRRITANT, TOXIC | | HS Code | 2933399990 | | Storage Class | 6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | | Hazard Classifications | Acute Tox. 3 Oral
Eye Dam. 1
Skin Irrit. 2
STOT SE 3 |
| | 2-Chloro-5-pyridineacetonitrile Usage And Synthesis |
| Uses | 2-Chloro-5-cyanomethylpyridine | | Synthesis | General procedure for the synthesis of 2-chloro-5-pyridylacetonitrile from 2-chloro-5-chloromethylpyridine and sodium cyanide:
Step 1. Synthesis of (6-chloropyridin-3-yl)acetonitrile. To a stirred solution of 2-chloro-5-chloromethylpyridine (25 g, 0.154 mol) in ethanol (40 mL) was slowly added an aqueous solution of sodium cyanide (8.17 g, 0.167 mol) (18 mL) at 0 °C. The reaction mixture was heated to reflux for 2 hours, followed by continued stirring at room temperature for 18 hours. Upon completion of the reaction, the solvent was removed by vacuum evaporation and the residue was dissolved in water and extracted with dichloromethane (500 mL). The organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography with the eluent being a 70/30 dichloromethane/hexane solvent mixture to give 20 g (85% yield) of brown oily product. The product was solidified by standing and ESI-MS m/z 153 (MH+). | | References | [1] Patent: WO2010/130708, 2010, A1. Location in patent: Page/Page column 105
[2] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 7, p. 2168 - 2173
[3] Patent: WO2013/13817, 2013, A1. Location in patent: Page/Page column 111
[4] Patent: WO2013/13815, 2013, A1. Location in patent: Page/Page column 221
[5] Patent: US2013/29961, 2013, A1. Location in patent: Paragraph 0705 |
| | 2-Chloro-5-pyridineacetonitrile Preparation Products And Raw materials |
| Raw materials | sodium:cyanide-->2-Chloro-5-(chloromethyl)pyridine-->Sodium cyanide-->POTASSIUM CYANIDE | | Preparation Products | BIPY531, 2,2'-([2,2'-Bipyridine]-5,5'-diyl)diacetonitrile-->Cyclobutanecarbonitrile, 1-[6-[5-(methylamino)-2-pyrazinyl]-3-pyridinyl]--->Cyclobutanecarbonitrile, 1-[6-(2-amino-5-pyrimidinyl)-3-pyridinyl]--->Pyridine, 2-chloro-5-[1-[5-(3-pyridinyl)-1,2,4-oxadiazol-3-yl]cyclobutyl]--->Cyclobutanecarbonitrile, 1-[6-(5-amino-2-pyrazinyl)-3-pyridinyl]--->1-(6-Chloropyridin-3-yl)cyclobutanecarbonitrile-->(6-tert-Butoxycarbonylamino-pyridin-3-yl)-acetic acid |
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