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| | 3,5-Bis(2-cyanoprop-2-yl)benzyl bromide Basic information |
| Product Name: | 3,5-Bis(2-cyanoprop-2-yl)benzyl bromide | | Synonyms: | 5-(BROMOMETHYL)-A,A,A,A-TETRAMETHYL-1,3-BENZENEDIACETONITRILE;5-BROMOMETHYL-A,A,A',A'-TETRAMETHYL-1,3-BENZENEDIACETONITRILE;5-(BROMOMETHYL)-ALPHA,ALPHA,ALPHA,ALPHA-TETRAMETHYL-1,3-BENZENEDIACETONITRILE;1,3-Benzenediacetonitrile, 5-(bromomethyl)-α,α,α',α'-tetramethyl-;Anastrozole EP Impurity C;2-2'-[5-(Bromomethyl)benzene-1,3- diyl]bis(2-methylpropanenitrile);3,5-Bis(1-cyano-1-methylethyl)benzyl Bromide;Anastrozole USP Related Compound D | | CAS: | 120511-84-4 | | MF: | C15H17BrN2 | | MW: | 305.21 | | EINECS: | 601-717-7 | | Product Categories: | Methyl Halides;Phenyls & Phenyl-Het;Anastrazole;Aromatics;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;Anastrozole;Intermediate of Anastrozole | | Mol File: | 120511-84-4.mol |  |
| | 3,5-Bis(2-cyanoprop-2-yl)benzyl bromide Chemical Properties |
| Melting point | 98-100°C | | Boiling point | 380.0±37.0 °C(Predicted) | | density | 1.276±0.06 g/cm3(Predicted) | | storage temp. | Inert atmosphere,2-8°C | | solubility | Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | | form | Solid | | color | White to Off-White | | InChI | InChI=1S/C15H17BrN2/c1-14(2,9-17)12-5-11(8-16)6-13(7-12)15(3,4)10-18/h5-7H,8H2,1-4H3 | | InChIKey | IHXHGCDOJLOZML-UHFFFAOYSA-N | | SMILES | C1(C(C)(C)C#N)=CC(CBr)=CC(C(C)(C)C#N)=C1 | | CAS DataBase Reference | 120511-84-4(CAS DataBase Reference) |
| | 3,5-Bis(2-cyanoprop-2-yl)benzyl bromide Usage And Synthesis |
| Chemical Properties | Off-White Solid | | Uses | α,α,α’,α’-Tetramethyl-5-bromomethyl-1,3-benzenediacetonitrile (Anastrozole EP Impurity C) is an impurity of Anastrozole (A637425) (impurity D). | | Synthesis | Using 5,α,α,α',α'-pentamethyl-1,3-benzenediacetonitrile as raw material, 3,5-bis(1-cyano-1-methylethyl)toluene (600 g, 2.65 mol) was obtained after step III. The product was mixed with N-bromosuccinimide (519 g, 2.916 mol) and benzoyl peroxide (17 g, 0.053 mol) in carbon tetrachloride (4.5 L) and the reaction was carried out at reflux for 2 to 2.5 hours. After completion of the reaction, the reaction mixture was cooled and filtered. The filtrate was concentrated to dryness at 40°C to 45°C. The resulting solid was dissolved in 2-propanol (2L) at 75°C to 80°C, followed by slow cooling to 10°C to 15°C and stirring at this temperature for 1 hour. The reaction mixture was further cooled to -5 °C to 0 °C and stirring was continued for 2 h, after which it was filtered and the filter cake was washed with pre-cooled 2-propanol (200 ml). The filter cake was subsequently washed with hexane and blotted dry. Finally, the filter cake was dried under vacuum at 40 °C to 45 °C to afford the target product 3,5-bis(1-cyano-1-methylethyl)benzyl bromide (700.2 g, 87.0% yield). | | References | [1] Patent: US2006/189670, 2006, A1. Location in patent: Page/Page column 5; 7
[2] Patent: US2006/35950, 2006, A1. Location in patent: Page/Page column 3; 11
[3] Patent: CN103554041, 2016, B. Location in patent: Paragraph 0014-0016
[4] Patent: US2009/221837, 2009, A1. Location in patent: Page/Page column 4
[5] Patent: WO2007/39913, 2007, A1. Location in patent: Page/Page column 14 |
| | 3,5-Bis(2-cyanoprop-2-yl)benzyl bromide Preparation Products And Raw materials |
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