3,5-Bis(2-cyanoprop-2-yl)toluene CAS 120511-72-0
3,5-Bis(2-cyanoprop-2-yl)toluene Basic information
| Product Name: | 3,5-Bis(2-cyanoprop-2-yl)toluene |
| Synonyms: | PENTAMETHYL-1,3-BENZENEDIACETONITRILE;2,2'-(5-METHYL-1,3-PHENYLENE)DI(2-METHYLPROPANENITRILE);2,2'-(5-methyl-1,3-phenylene)di(2-methylpropionitrile);3,5-Bis (2-cyanoisopropyl ) toluene;2,2’-(5-Methyl-1,3-phenylene)-di(2-methylpropiononitrile;2,2-(5-Methyl-1,3-Phenylene)-Bis-(2-Methyl-Propionitrile);3,5-Bis(2-Cyanoisopropyl)Toluene(ForAnastrozole);2,2-(5-methyl-1,3-phenylene)di(2-methylpropiononitrile (intermediate of anastrozole) |
| CAS: | 120511-72-0 |
| MF: | C15H18N2 |
| MW: | 226.32 |
| EINECS: | 1806241-263-5 |
| Product Categories: | Intermediate of Anastrozole;INTERMEDIATESOFANASTROZOLE;Anastrozole;Nitriles;(intermediate of anastrozole);Aromatics;Anastrazole;Inhibitors;Intermediates & Fine Chemicals;Isotope Labelled Compounds;Pharmaceuticals |
| Mol File: | 120511-72-0.mol |
3,5-Bis(2-cyanoprop-2-yl)toluene Chemical Properties
| Melting point | 127-130°C |
| Boiling point | 339.1±32.0 °C(Predicted) |
| density | 1.002±0.06 g/cm3(Predicted) |
| storage temp. | Sealed in dry,Room Temperature |
| solubility | Chloroform (Sparingly), Methanol (Slightly) |
| form | Solid |
| color | White to Off-White |
| Major Application | pharmaceutical (small molecule) |
| InChI | InChI=1S/C15H18N2/c1-11-6-12(14(2,3)9-16)8-13(7-11)15(4,5)10-17/h6-8H,1-5H3 |
| InChIKey | SJECEXNMZXMXNE-UHFFFAOYSA-N |
| SMILES | C1(=CC(C)=CC(C(C)(C)C#N)=C1)C(C)(C)C#N |
| CAS DataBase Reference | 120511-72-0(CAS DataBase Reference) |
Safety Information
| WGK Germany | WGK 3 |
| HS Code | 2926900005 |
| Storage Class | 11 - Combustible Solids |
| Chemical Properties | 3,5-Bis(2-cyanoprop-2-yl)toluene is White Solid |
| Uses | 3,5-Bis(2-cyanoprop-2-yl)toluene is a labelled intermediate in the synthesis of Anastrozole, an aromatase inhibitor. Used as an antineoplastic. |
| Uses | α,α,α’,α’-Tetramethyl-5-methyl-1,3-benzenediacetonitrile (Anastrozole EP Impurity H) is an intermediate in the synthesis of Anastrozole (A637425), an aromatase inhibitor. Used as an antineoplastic. |
| Uses | An intermediate in the synthesis of Anastrozole (A637425), an aromatase inhibitor. Used as an antineoplastic. |
| Synthesis | 120511-74-2 74-88-4 120511-72-0 General procedure for the synthesis of 5,α,α,α,α',α'-pentamethyl-1,3-benzenediacetonitrile from 2,2'-(5-methyl-1,3-phenylene)bisacetonitrile and iodomethane: A mixture of 3,5-bis(cyano-methyl)toluene (800 g, 4.70 mol), methyl iodide (2,935.2 g, 20.68 mol) and dimethylformamide (11.20 L) was was cooled to 0°C to 5°C. A dispersion of 60% sodium hydride in mineral oil (864.2 g, 36.0 mol) was added in batches over 1 to 1.5 hours. Subsequently, the reaction mixture was gradually warmed to room temperature and stirred continuously for 2 to 2.5 hours. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding agent was hexane: ethyl acetate = 7.5:2.5). After confirming the completion of the reaction, ethyl acetate was added to quench the excess sodium hydride. The reaction mixture was diluted with water and extracted with dichloromethane (3 x 5 L). The organic phase was combined and washed with brine (5 L). The organic phase was decolorized with activated charcoal for 1 h at room temperature and subsequently concentrated to dryness under reduced pressure at 40°C to 45°C. The resulting residue was dissolved in carbon tetrachloride (2400 mL) at 70°C to 75°C and gradually cooled to 10°C to 15°C with stirring for 1 hour. The solution was further cooled to -5°C to 0°C and stirring was continued for 3 hours. Finally, the stirred suspension was filtered, the filter cake was washed with pre-cooled carbon tetrachloride (500 mL) and dried under vacuum at 40 °C to 45 °C to give 3,5-bis(1-cyano-1-methylethyl)toluene (748.0 g, 70.3% yield). |
| References | [1] Organic and Biomolecular Chemistry, 2007, vol. 5, # 18, p. 2940 - 2952 [2] Patent: WO2006/836, 2006, A1. Location in patent: Page/Page column 2; 9-10; 14; Figure 2 [3] Patent: US2006/189670, 2006, A1. Location in patent: Page/Page column 5-7 [4] Patent: WO2007/39913, 2007, A1. Location in patent: Page/Page column 13-14 [5] Patent: US2008/207915, 2008, A1. Location in patent: Page/Page column 5 |
3,5-Bis(2-cyanoprop-2-yl)toluene Preparation Products And Raw materials
| Raw materials | potassium 2-cyano-2-methylpropanoate-->3,5-Dibromotoluene-->2-[3-(2-cyanopropan-2-yl)-5-(1,2,4-triazol-4-ylmethyl)phenyl]-2-methyl-propaneni-->2-cyano-2-methylpropanoic acid-->3,5-DIIODOTOLUENE-->3,5-Bis(2-cyanoprop-2-yl)benzyl bromide-->Anastrozole-->1,2,4-Triazolylsodium-->Methyl p-toluenesulfonate-->Iodomethane-->5-Methyl-1,3-benzenediacetonitrile |
