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Chemical Structure| 374554-41-3 Chemical Structure| 374554-41-3

Structure of 374554-41-3

Chemical Structure| 374554-41-3

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Product Details of [ 374554-41-3 ]

CAS No. :374554-41-3
Formula : C7H3BrClFO
M.W : 237.45
SMILES Code : O=C(Cl)C1=CC=CC(Br)=C1F
MDL No. :MFCD09864687

Safety of [ 374554-41-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P280-P305+P351+P338
Class:8
UN#:3265
Packing Group:

Application In Synthesis of [ 374554-41-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 374554-41-3 ]

[ 374554-41-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 161957-56-8 ]
  • [ 374554-41-3 ]
YieldReaction ConditionsOperation in experiment
N,N-dimethyl-formamide; In oxalyl dichloride; dichloromethane; REFERENCE EXAMPLE 24 To a solution of <strong>[161957-56-8]3-bromo-2-fluorobenzoic acid</strong> (2.3 g) in dichloromethane (20 ml) were added in turn oxalyl chloride (1.83 ml) and a catalytic amount of N,N-dimethylformamide (2 drops) at ambient temperature. After stirring at ambient temperature for an hour, the reaction mixture was evaporated in vacuo to give 3-bromo-2-fluorobenzoyl chloride.
With thionyl chloride; for 2h;Heating / reflux; Example A.5; a) Preparation of intermediate (15); A mixture of 3-bromo-2-fluoro-benzoic acid (22 mmol) and thionyl chloride (20 mL) was stirred and refluxed for 2 hours. The reaction mixture was concentrated in vacuo, and co-evaporated twice with toluene (40 mL), yielding intermediate (15), which was used as such in the next step.
With thionyl chloride; In dichloromethane; for 6h;Reflux; To a stirred solution of <strong>[161957-56-8]3-bromo-2-fluorobenzoic acid</strong> (24.3 g, 111 mmol) in CH2Cl2 (100 mL) was added SOCl2 (12.2 mL, 166 mmol). The mixture was stirred under reflux for 6 h until the solution is colorless. CH2Cl2 was removed under vacuum. Then the residue was dissolved in ethyl acetate (200 mL) and then added dropwise to NH3H2O (80 mL). The organic layer was washed with H2O (50 mL*2), brine and dried over Na2SO4, filtered and concentrated to give 23.8 g of the title compound as a white solid (98% yield).
With thionyl chloride; In dichloromethane; for 6h;Reflux; Example 20 3-Bromo-2-fluorobenzamide To a stirred solution of <strong>[161957-56-8]3-bromo-2-fluorobenzoic acid</strong> (24.3 g, 111 mmol) in CH2Cl2 (100 mL) was added SOCl2 (12.2 mL, 166 mmol). The mixture was stirred under reflux for 6 h until the solution is colorless. CH2Cl2 was removed under vacuum, the residue was dissolved in ethyl acetate (200 mL), then was added dropwise to NH3H2O (80 mL). The organic layer was wash with H2O (50 mL*2), brine and dried Na2SO4, filtered and concentrated to give 23.8 g of the title compound as a white solid (98% yield).
With thionyl chloride;N,N-dimethyl-formamide; at 85℃; for 3h; Example 7; 9-(pyrrolidin-1-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine dihydrochloride; (1) N-benzyl-3-bromo-2-fluoro-N-(2-hydroxyethyl)benzamide; A solution of <strong>[161957-56-8]3-bromo-2-fluorobenzoic acid</strong> (10.0 g, 45.9 mmol) and N,N-dimethylformamide (0.100 ml) in thionylchloride (10 ml) was stirred for 3 hr at 85C, and the solvent was evaporated under reduced pressure. The residue was added to a solution of N-benzylethanolamine (6.94 g, 45.8 mmol) and triethylamine (9.60 ml, 68.9 mmol) in tetrahydrofuran (140 ml) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the desired product (11.5 g, 68.9%) as an oil. 1H-NMR (CDCl3) δ; 1.58 (0.3H, t, J = 6.0 Hz), 2.71 (0.7H, t, J = 5.1 Hz), 3.27-3.31 (0.6H, m), 3.57-3.68 (2H, m), 3.78-3.83 (1.4H, m), 4.50 (1.4H, s), 4.90 (0.6H, s), 7.04-7.14 (2H, m), 7.28-7.40 (5H, m), 7.56-7.62 (1H, m).
With thionyl chloride; In dichloromethane; for 6h;Reflux; Example 17 3-Bromo-2-fhiorobenzamideTo a stirred solution of <strong>[161957-56-8]3-bromo-2-fluorobenzoic acid</strong> (24.3 g, 111 mmol) in CH2Cl2 (100 mL) was added SOCl2 (12.2 mL, 166 mmol). The mixture was stirred under reflux for 6 h until the solution is colorless. CH2Cl2 was removed under vacuum. Then the residue was dissolved in ethyl acetate (200 mL) and then added dropwise to NH3H2O (80 mL). The organic layer was washed with H2O (50 mL x 2), brine and dried over Na2SOzI, filtered and concentrated to give 23.8 g of the title compound as a white solid (98% yield).
With thionyl chloride;Reflux; General procedure: A mixture of benzoic acid 8 (10 mmol) in sulfinyl dichloride (SOCl2, 20-50 mmol) was stirred under reflux condition for 3-8 h, and then the solvent was removed under reduced pressure to afford crude chlorides 9. Ammonium thiocyanate (15 mmol) and PEG-400 (0.18 g) were added to the solution of benzoyl chloride 9 (10 mmol) in dichloromethane (25 mL). The mixture was stirred at room temperature for 1 h. Then the precipitate was filtered off, the filtrate containing compounds 10 was collected to be used in next step directly.
With thionyl chloride; triethylamine; In tetrahydrofuran; for 1h; To a solution of <strong>[161957-56-8]3-bromo-2-fluorobenzoic acid</strong> (3.77 g, 17.2 mmol) in dry tetrahydrofuran (200 ml) was added triethylamine (4.77 ml, 34.4 mmol) and thionyl chloride (1.69 ml, 21.5 mmol). The reaction mixture was stirred for 1 h and then quenched with ammonia in methanol (10 ml, saturated). After an additional hour of stirring the mixture was evaporated and the crude product was purified by flash column chromatography (ethyl acetate/isooctane 1:1) to give the title compund (1.76 g). MS m/z (rel. intensity, 70 eV) 219 (M+, 26), 217 (M+, 26), 203 (62), 201 (70), 94 (bp).
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 25℃; for 2h;Inert atmosphere; Synthesis of (3b) To a solution of <strong>[161957-56-8]3-bromo-2-fluorobenzoic acid</strong> (3a) (2.5 g, 11.42 mmol) in DCM (10 mL) were added DMF (83.44 mg, 1.14 mmol, 87.83 uL) and oxalyl dichloride (2.90 g, 22.83 mmol, 2.00 mL) at 0 C. under N2. After addition, the mixture was stirred at 25 C. under N2 for 2 hrs. The reaction mixture was concentrated under reduced pressure to give 3-bromo-2-fluorobenzoyl chloride (3b) which was used directly in the next step.
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 4h; A suspension of 3-bromo-2-fiuorobenzoic acid (1 g, 4.6 mmol) in DC (15 mL) at 0 C was treated with oxaiyl chloride (474 mI_, 5.5 mmol) dropwise over 2 minutes. DMF (2 drops) was added and the reaction mixture was stirred at room temperature for 4 h. Solvent was removed under reduced pressure to give crude 3-bromo-2-fluorobenzoyl chloride, which was used immediately without further purification.

  • 2
  • [ 206551-41-9 ]
  • [ 374554-41-3 ]
 

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