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| | 5-Chloro-2-fluorobenzyl bromide Basic information |
| Product Name: | 5-Chloro-2-fluorobenzyl bromide | | Synonyms: | 5-CHLORO-2-FLUOROBENZYL BROMIDE;alpha-Bromo-3-chloro-6-fluorotoluene;à-bromo-3-chloro-6-fluorotoluene;5-Chloro-2-fluoronitrobenzenebenzyl bromide;2-Fluoro-5-chlorobenzyl bromide;2-(Bromomethyl)-4-chloro-1-fluorobenzene;1-(Bromomethyl)-5-chloro-2-fluorobenzene;-bromo-3-chloro-6-fluorotoluene | | CAS: | 71916-91-1 | | MF: | C7H5BrClF | | MW: | 223.47 | | EINECS: | 670-703-0 | | Product Categories: | Fluorine series | | Mol File: | 71916-91-1.mol |  |
| | 5-Chloro-2-fluorobenzyl bromide Chemical Properties |
| Melting point | 45°/0.5mm | | Boiling point | 44-45°C 0,5mm | | density | 1.65 | | refractive index | 1.565 | | Fp | 44-45°C/0.5mm | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | form | clear liquid | | color | Colorless to Light yellow to Light orange | | Sensitive | Lachrymatory | | BRN | 637765 | | CAS DataBase Reference | 71916-91-1(CAS DataBase Reference) |
| Hazard Codes | C,Xn | | Risk Statements | 34-36/37/38-22 | | Safety Statements | 26-36/37/39-45 | | RIDADR | 3265 | | Hazard Note | Corrosive/Lachrymatory | | HazardClass | 8 | | PackingGroup | III | | HS Code | 29039990 |
| | 5-Chloro-2-fluorobenzyl bromide Usage And Synthesis |
| Uses | 2-(bromomethyl)-4-chloro-1-fluoro-Benzene is a useful reactant which has been used in the synthesis of potential cell cycle inhibitors in HepG2 cells. | | Synthesis | General procedure for the synthesis of 5-chloro-2-fluorobenzyl bromide from 5-chloro-2-fluorotoluene:
A: 5-Chloro-2-fluorotoluene (100 g, 692 mmol) was dissolved in ethyl acetate (300 ml) at 20 °C. To this solution N-bromosuccinimide (147.7 g, 830 mmol) and dibenzoyl peroxide (2 g, 8.25 mmol) were added sequentially. The reaction mixture was heated to 80 °C and stirred for 3 hours. Upon completion of the reaction, heptane (300 ml) was added and the mixture was cooled to 0 °C, at which time the succinimide precipitated. After filtration and washing with heptane, the residue was washed with water (1500 ml). The filtrate was concentrated to dryness under vacuum to give 162 g of the crude product 5-chloro-2-fluorobenzyl bromide. The crude product (141 g) was purified by vacuum distillation at 99 °C and 33 mbar to give the final 5-chloro-2-fluorobenzyl bromide (99 g, 75% yield). The purity of the product was analyzed by GC to be 87.1% (% area).1H-NMR (CDCl3) data: δ 4.44 (2H, d, CH2), 7.01 (1H, t, H3), 7.26 (1H, m, H4), 7.38 (1H, m, H6). | | References | [1] Journal of Heterocyclic Chemistry, 1997, vol. 34, # 1, p. 27 - 32
[2] Patent: WO2008/3460, 2008, A1. Location in patent: Page/Page column 23-24
[3] Patent: US2008/9619, 2008, A1. Location in patent: Page/Page column 11-12
[4] Journal of Medicinal Chemistry, 1991, vol. 34, # 10, p. 3098 - 3105
[5] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 19, p. 2903 - 2909 |
| | 5-Chloro-2-fluorobenzyl bromide Preparation Products And Raw materials |
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