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Chemical Structure| 33924-45-7 Chemical Structure| 33924-45-7

Structure of 33924-45-7

Chemical Structure| 33924-45-7

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Product Details of [ 33924-45-7 ]

CAS No. :33924-45-7
Formula : C7H5Br2Cl
M.W : 284.38
SMILES Code : ClC1=CC=C(CBr)C(Br)=C1
MDL No. :MFCD12024978

Safety of [ 33924-45-7 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:3265
Packing Group:

Application In Synthesis of [ 33924-45-7 ]

* 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 [ 33924-45-7 ]

[ 33924-45-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 27139-97-5 ]
  • [ 33924-45-7 ]
YieldReaction ConditionsOperation in experiment
83% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 24h;Reflux; Take a 500 ml double-necked round bottom bottle and place it in a stirrer and a reflux tube. After drying, it is filled with nitrogen. First, add compound A-3 (20.548 g, 1.0 equivalent) and NBS (N-bromosuccinimide). , 19.5778 g, 1.1 eq.), and AIBN (azobisisobutyronitrile, 0.821 g, 0.5 molpercent), followed by the addition of carbon tetrachloride (250 ml) and stirred for 10 minutes, finally heated to reflux and reacted After 24 hours; after the temperature was warmed, water (200 ml) was added, followed by extraction with ethyl acetate (3×200 ml), and the obtained extract was sequentially dried over magnesium sulfate, filtered and dried. Purification (ethyl acetate / hexanes, 1/10) afforded Intermediate 1-3 (23.604 g, yield 83percent).
80% With bromine; at 190℃; for 3h;Irradiation; In a three-necked round-bottom 500 ml flask equipped with a reflux condenser, thermometer, dropping funnel with pressure-equalizing, and magnetic stirring bar, 41.3 ml (128 g, 0.80 mmol) of bromine were added dropwise to 164 g (0.80 mol) of <strong>[27139-97-5]2-bromo-4-chlorotoluene</strong> under exposure to 500 W lamp for 3 h at 19O0C. The resulting mixture was cooled to room temperature. Fractional distillation gave a colorless liquid, b.p. 1 1 1-1 15C/7 mm Hg. Yield 182 g (80%).Anal. calc. for C7H5Br2Cl: C, 29.56; H, 1.77. Found: C, 29.76; H, 1.89.1H NMR (CDCl3): delta 7.44 (d, J= 1.7 Hz, IH, 2-H), 7.36 (dd, J= 6.0 Hz, J= 1.7 Hz, IH, 4-H), 7.18 (d, J= 6.0 Hz, IH, 5-H), 4.69 (s, 2H, CH2).
75% With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 90℃; for 24h; (b) into a 500mL three-neck bottle add 50g of compound 3, 50g of NBS (i.e. N-bromosuccinimide), 0.3g of BetaRho0 (i.e. dibenzoyl peroxide) and 300mL of carbon tetrachloride, the external temperature is raised at 90 C and the reaction is carried out for 24h (at this time, TLC showed complete reaction); pour the reaction solution into 500mL of ice water, adjust the pH at 10 with 2N (equivalent concentration) sodium hydroxide solution, layered extraction, combined organic phase, wash once with 5% sodium bicarbonate (mass concentration, the same below) solution, dry and then spin dry, separated by column chromatography and then obtained 52 g of compound 4 (yield is 75%)
75% With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 90℃; for 24h; (b) 50 g of compound 3, 50 g of NBS (ie N-bromosuccinimide), 0.3 g of BPO (ie dibenzoyl peroxide) and 300 mL of carbon tetrachloride were added to a 500 mL three-necked flask, and the external temperature was raised to At 90 C, the reaction was carried out for 24 h (at this time, TLC showed complete reaction);Pour the reaction solution into 500 mL of ice water, adjust the pH to 10 with 2N (equivalent concentration) sodium hydroxide solution, extract the layers, combine the organic phases, and wash with 5% sodium bicarbonate (mass concentration, the same below) solution. After drying, it was spin-dried, and column chromatography was carried out to obtain 52 g of Compound 4 (yield: 75%) (the nuclear magnetic spectrum of Compound 4 is shown in Fig. 3, and the specific resolution is: 1H NMR (400 MHz, CDCl3) delta (ppm): 7.58 ( d, J = 2.0 Hz, 1H), 7.38 (d, J = 4.0 Hz, 1H), 7.28 (d, J = 4.0 Hz, 1H), 4.55 (s, 1H))
64% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 4h;Heating / reflux; 2-Bromo-4-chlorobenzylbromide (5b). To the bromoderivative (6.71 g, 32.68 mmol) (4) dissolved in CCl4 were added N-bromosuccinimide (NBS) (5.82 g, 32.68 mmol), a,a'-azoisobutyronitrile (AIBN) (107.2 mg, 0.65 mmol) and after heating at reflux for 4 hours, the reaction mix- ture was cooled and filtered on Gooch. The filtrate was washed with aqueous sodium thiosulphate solution and then the organic phase was anhydrified on anhydrous sodium sulphate and the solvent evapo- rated. The crude reaction product was purified by flash chromatogra- phy, using n-hexane as the eluent. 6.00 g of product (5b) are thus obtained as a colourless oil with a yield of 64%. ¹H NMR (CDCIs) 8 7.58 (d, 1H, J = 1.75 Hz), 7.38 (d, 1H, J = 8.51 Hz), 7.28 (m, 1H), 4.55 (s, 2H); MS m/z 284 (M+), 205 (100), 169,124, 89; Anal. (C7H5Br2CI) C, H, N compliant with the expected structure.
182 g (80%) With bromine; 2-Bromo-4-chlorobenzyl bromide In a three-necked round-bottom 500 ml flask equipped with a reflux condenser, thermometer, dropping funnel with pressure-equalizing, and magnetic stirring bar, 41.3 ml (128 g, 0.80 mmol) of bromine were added dropwise to 164 g (0.80 mol) of <strong>[27139-97-5]2-bromo-4-chlorotoluene</strong> under exposure to 500 W lamp for 3 h at 190 C. The resulting mixture was cooled to room temperature. Fractional distillation gave a colorless liquid, b.p. 111-115 C./7 mm Hg. Yield 182 g (80%). Anal. calc. for C7H5Br2Cl: C, 29.56; H, 1.77. Found: C, 29.76; H, 1.89. 1H NMR (CDCl3): delta 7.44 (d, J=1.7 Hz, 1H, 2-H), 7.36 (dd, J=6.0 Hz, J=1.7 Hz, 1H, 4-H), 7.18 (d, J=6.0 Hz, 1H, 5-H), 4.69 (s, 2H, CH2).
With N-Bromosuccinimide; 1) Preparation of 4-[3-(2-bromo-4-chlorobenzyl)-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrile 109.2Compound 109.2 was prepared as described for example 1.2, by reacting compound 1.1, instead of 2-bromobenzyl bromide, with 2-bromo-1-bromomethyl-4-chlorobenzene (prepared by N-bromosuccinimide bromination from <strong>[27139-97-5]2-bromo-4-chloro-1-methylbenzene</strong>; 1H NMR: 7.82, d, 1H; 7.65, s, 1H, 7.5, d, 1H, 4.72, s, 2H). 4-[3-(2-Bromo-4-chlorobenzyl)-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrile was obtained. (Molecular weight 498.99 (C20H14BrClF3N3O2); retention time Rt=2.30 min. [B]; MS (ESI): 541.04 (MH++CH3CN).

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  • [ 33924-45-7 ]
  • [ 52927-98-7 ]
 

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