4-Cyanobenzyl bromide CAS 17201-43-3
4-Cyanobenzyl bromide Basic informationUses Chemical Properties
| Product Name: | 4-Cyanobenzyl bromide |
| Synonyms: | 4-(bromomethyl)-benzonitril;4-(BROMOMETHYL)BENZONITRILE;4CNBB;4-CYANOBENZYL BROMIDE;Benzonitrile, 4-(bromomethyl)-;Benzonitrile, p-(bromomethyl)-;p-(Bromomethyl)benzonitrile;p-Tolunitrile, alpha-bromo- |
| CAS: | 17201-43-3 |
| MF: | C8H6BrN |
| MW: | 196.04 |
| EINECS: | 241-246-0 |
| Product Categories: | Aromatics;Miscellaneous;Aromatic Halides (substituted);Organics;Aromatics Compounds;Building Blocks;C8 to C9;Chemical Synthesis;Cyanides/Nitriles;Nitrogen Compounds;Organic Building Blocks |
| Mol File: | 17201-43-3.mol |
4-Cyanobenzyl bromide Chemical Properties
| Melting point | 115-117 °C(lit.) |
| Boiling point | 143 °C / 12mmHg |
| density | 1.5466 (rough estimate) |
| refractive index | 1.6550 (estimate) |
| storage temp. | Inert atmosphere,2-8°C |
| solubility | Chloroform (Slightly), Methanol (Slightly) |
| form | Liquid |
| color | Clear colorless to yellow |
| Water Solubility | Soluble in chloroform and methanol. Insoluble in water. |
| BRN | 636717 |
| InChI | InChI=1S/C8H6BrN/c9-5-7-1-3-8(6-10)4-2-7/h1-4H,5H2 |
| InChIKey | UMLFTCYAQPPZER-UHFFFAOYSA-N |
| SMILES | C(#N)C1=CC=C(CBr)C=C1 |
| CAS DataBase Reference | 17201-43-3(CAS DataBase Reference) |
| NIST Chemistry Reference | «ALPHA»-bromo-p-tolunitrile(17201-43-3) |
| EPA Substance Registry System | Benzonitrile, 4-(bromomethyl)- (17201-43-3) |
Safety Information
| Hazard Codes | C |
| Risk Statements | 34-42/43 |
| Safety Statements | 22-26-36/37/39-45-28A |
| RIDADR | UN 3261 8/PG 2 |
| WGK Germany | 3 |
| F | 10-19-21 |
| Hazard Note | Corrosive |
| TSCA | TSCA listed |
| HazardClass | 8 |
| PackingGroup | II |
| HS Code | 29269090 |
| Storage Class | 8A - Combustible corrosive hazardous materials |
| Hazard Classifications | Resp. Sens. 1 Skin Corr. 1B |
| Uses | 4-Cyanobenzyl bromide is an important intermediate for pharmaceutical production. It can be used for the synthesis of a series of piperidine-linked aromatic diimidazolines, which have been synthesized as conformationally restricted congeners of the anti-Pneumocystis carinii (PCP) drug, Pentamidine. |
| Chemical Properties | 4-Cyanobenzyl bromide (C8H6BrN, CAS registry No. 17201-43-3) is a white solid. Its melting point is 113-117°C, and flash point is 125.1°C. It is insoluble in water at 20°C. It is stable under normal temperatures and pressures. It should be stored at 0-5°C. |
| Chemical Properties | white to light yellow crystal powde |
| Uses | A benzyl halide as postemergence herbicides. |
| Uses | 4-(Bromomethyl)benzonitrile is used in the synthesis of ligands containing a chelating pyrazolyl-pyridine group with a pendant aromatic nitrile. It is also useful in the preparation of 4-[(2H-tetra-zol-2-yl)methyl]benzonitrile by reaction with 2H-tetrazole in the presence of potassium hydroxide. |
| Uses | 4-(Bromomethyl)benzonitrile may be used in the synthesis of ligands containing a chelating pyrazolyl-pyridine group with a pendant aromatic nitrile. |
| General Description | 4-(Bromomethyl)benzonitrile reacts with 2H-tetrazole in the presence of KOH to yield 4-[(2H-tetra-zol-2-yl)methyl]benzonitrile. |
| Synthesis | 874-89-5 17201-43-3 GENERAL METHOD: Hydroxymethyl (1 mmol) and potassium bromide (1.5 mmol, 0.18 g) were dissolved in ethanol (5 mL) and phosphorus pentoxide (1.5 mmol, 0.23 g) was added. The reaction mixture was stirred at room temperature until the reaction was complete (monitored by TLC or GC). After completion of the reaction, the mixture was filtered and the residue was washed with ethyl acetate (3 x 8 mL). The organic layers were combined, washed with water (10 mL) and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give the crude 4-cyanobenzyl bromide product. If further purification is required, column chromatography can be used. |
| References | [1] Tetrahedron Letters, 2016, vol. 57, # 2, p. 168 - 171 [2] Organic Letters, 2015, vol. 17, # 15, p. 3810 - 3813 [3] Advanced Synthesis and Catalysis, 2016, vol. 358, # 11, p. 1731 - 1735 [4] Patent: US6384080, 2002, B1 |
4-Cyanobenzyl bromide Preparation Products And Raw materials
| Raw materials | p-Tolunitrile-->4-(HYDROXYMETHYL)BENZONITRILE-->Benzoyl peroxide-->Phosphorus pentoxide-->Acetonitrile-->Potassium bromide |
| Preparation Products | TERT-BUTYL 4-(4-FORMYLBENZYL)PIPERAZINE-1-CARBOXYLATE-->4-Cyanobenzoic acid-->Letrozole-->4-(4-CYANOBENZYL)-1,2,4-TRIAZOLE-->(4-CYANOBENZYL)PHOSPHONIC ACID DIETHYL ESTER-->4-CYANOPHENYLACETONITRILE 97-->Ethyl 4-(bromomethyl)benzoate-->TERT-BUTYL 4-(BROMOMETHYL)BENZYLCARBAMATE-->(4-AMINOMETHYL-PHENYL)-METHANOL-->Bromoethane-->4-[1-Cyano-2-(4-cyanophenyl)ethyl]benzonitrile-->Thioacetic acid S-(4-cyano-benzyl) ester-->3-MORPHOLIN-4-YLMETHYL-BENZYLAMINE |
