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| | 4-(Trifluoromethoxy)benzyl bromide Basic information | | Uses |
| | 4-(Trifluoromethoxy)benzyl bromide Chemical Properties |
| Melting point | 22-24°C | | Boiling point | 82-84 °C10 mm Hg(lit.) | | density | 1.594 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.48(lit.) | | Fp | 202 °F | | storage temp. | Refrigerated. | | solubility | soluble in Chloroform, Methanol | | form | Liquid or Low Melting Solid | | Specific Gravity | 1.594 | | color | Clear faintly yellow | | Sensitive | Lachrymatory | | BRN | 2521451 | | InChI | InChI=1S/C8H6BrF3O/c9-5-6-1-3-7(4-2-6)13-8(10,11)12/h1-4H,5H2 | | InChIKey | JDNPUJCKXLOHOW-UHFFFAOYSA-N | | SMILES | C1(CBr)=CC=C(OC(F)(F)F)C=C1 | | CAS DataBase Reference | 50824-05-0(CAS DataBase Reference) |
| Hazard Codes | C | | Risk Statements | 34 | | Safety Statements | 26-27-28-36/37/39-45 | | RIDADR | UN 3265 8/PG 2 | | WGK Germany | 3 | | Hazard Note | Corrosive/Lachrymatory | | HazardClass | 8 | | PackingGroup | III | | HS Code | 29093090 | | Storage Class | 8A - Combustible corrosive hazardous materials | | Hazard Classifications | Eye Dam. 1
Skin Corr. 1B |
| | 4-(Trifluoromethoxy)benzyl bromide Usage And Synthesis |
| Uses | 4-Trifluoromethoxybenzyl Bromide is a useful synthetic intermediate. It is used to prepare (nitro)[(trifluoromethoxy)benzyloxy]dihydroimidazo[2,1-b][1,3]oxazines with antitubercular activities. It is also used to synthesize tetrahydronaphthalenols with anti-allergic activities. | | Chemical Properties | Colorless to light yellow liqui | | Uses | 4-(Trifluoromethoxy)benzyl bromide may be used in the synthesis of bioreductive drug, (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824). | | General Description | Polymerizations of 4-(trifluoromethoxy)benzyl bromide, via Friedel-Crafts polymerization using aluminum chloride as a catalyst has been reported. | | Synthesis | Synthesis of 1-(bromomethyl)-4-(trifluoromethoxy)benzene: Phosphorus tribromide (6 g, 22.2 mmol) was slowly added dropwise to a solution of (4-(trifluoromethoxy)phenyl)methanol (3.6 g, 18.8 mmol) in dichloromethane (60 mL) at 0-10 °C and stirred for 30 min. The reaction mixture was then continued to stir at room temperature for 3 hours. Upon completion of the reaction, the reaction was terminated by the addition of water (30 mL) and the mixture was washed sequentially with aqueous sodium bicarbonate (2 x 30 mL) and brine (30 mL). The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure to give 4-trifluoromethoxybenzyl bromide (3.5 g, 66% yield) as a yellow oil. | | References | [1] Patent: US2007/270434, 2007, A1. Location in patent: Page/Page column 17
[2] J. Gen. Chem. USSR (Engl. Transl.), 1965, vol. 35, p. 1631 - 1637
[3] Zhurnal Obshchei Khimii, 1965, vol. 35, p. 1628 - 1636
[4] Journal of Medicinal Chemistry, 2005, vol. 48, # 2, p. 556 - 568
[5] Organometallics, 2014, vol. 33, # 21, p. 5940 - 5943 |
| | 4-(Trifluoromethoxy)benzyl bromide Preparation Products And Raw materials |
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