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Chemical Structure| 29568-33-0 Chemical Structure| 29568-33-0

Structure of 29568-33-0

Chemical Structure| 29568-33-0

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Product Details of [ 29568-33-0 ]

CAS No. :29568-33-0
Formula : C8H6Cl2O2
M.W : 205.04
SMILES Code : O=C(Cl)C1=CC(Cl)=CC=C1OC
MDL No. :MFCD03208980
InChI Key :JVLUMHRASWENRU-UHFFFAOYSA-N
Pubchem ID :12384176

Safety of [ 29568-33-0 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H314
Precautionary Statements:P264-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P403+P233-P501
Class:8
UN#:3265
Packing Group:

Application In Synthesis of [ 29568-33-0 ]

* 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 [ 29568-33-0 ]

[ 29568-33-0 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 3929-47-3 ]
  • [ 29568-33-0 ]
  • 5-chloro-2-methoxybenzoic acid 3-(3,4-dimethoxyphenyl)-1-propyl ester [ No CAS ]
  • 2
  • [ 30748-47-1 ]
  • [ 29568-33-0 ]
  • [ 1065640-14-3 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In tetrahydrofuran; at 50℃; for 18h; Example 40A N-(5-acetyl-4-methylthiazol-2-yl)-5-chloro-2-methoxybenzamide To a solution of <strong>[30748-47-1]5-acetyl-2-amino-4-methylthiazole</strong> (5.0 g, 32 mmol) in 50 mL of tetrahydrofuran was added triethylamine (13.4 mL, 96 mmol) followed by Example 18B (32 mmol) in 10 mL of tetrahydrofuran via cannula. The mixture was warmed to 50 C. and was allowed to stir for 18 hours. The mixture was cooled to ambient temperature quenched with 15 mL of NH4Cl and diluted with 15 mL of ethyl acetate. The layers were separated and the aqueous layer was extracted with three 10 mL portions of ethyl acetate. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was washed with ethyl acetate and the remaining solids were pure title compound. MS (DCI/NH3) m/z 325 (M+H)+.
With triethylamine; In tetrahydrofuran; at 50℃; for 18h; To a solution of <strong>[30748-47-1]5-acetyl-2-amino-4-methylthiazole</strong> (5.0 g, 32 mmol) in 50 mL of tetrahydrofuran was added triethylamine (13.4 mL, 96 mmol) followed by Example 205B (32 mmol) in 10 mL of tetrahydrofuran via cannula. The mixture was warmed to 50 0C and was allowed to stir for 18 hours. The mixture was cooled to ambient temperature quenched with 15 mL OfNH4Cl and diluted with 15 mL of ethyl acetate. The layers were separated and the aqueous layer was extracted with three 10 mL of portions of ethyl acetate. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was washed with ethyl acetate and the remaining solids were pure title compound. MS (DCI/NH3) m/z 325 (M+H)+
  • 3
  • [ 45865-42-7 ]
  • [ 29568-33-0 ]
  • [ 959792-98-4 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 0 - 20℃; for 12.0h; Example 48A N-(5-tert-butyl-4-methylthiazol-2-yl)-5-chloro-2-methoxybenzamide To a mixture of <strong>[45865-42-7]5-tert-butyl-4-methylthiazol-2-amine</strong> (500 mg, 2.94 mmol) and Example 18B (615 mg, 3 mmol) in anhydrous CH2Cl2 (50 mL) at 0 C. was added dropwise triethylamine (0.56 mL, 4 mmol) and the mixture was allowed to warm to ambient temperature for 12 h. The mixture was then washed with water, brine, dried with anhydrous MgSO4 and concentrated under reduced pressure. The residue was purified by chromatography (hexane-EtOAc 1:1) to afford 525 mg of the title compound. MS (DCI/NH3) m/z 339 (M+H)+.
  • 4
  • [ 35418-07-6 ]
  • [ 29568-33-0 ]
  • [ 61629-76-3 ]
  • 5
  • [ 35418-07-6 ]
  • [ 29568-33-0 ]
  • C18H18ClNO4 [ No CAS ]
  • 6
  • [ 55877-79-7 ]
  • [ 29568-33-0 ]
  • 7
  • [ 777-12-8 ]
  • [ 29568-33-0 ]
  • 5-chloro-2-methoxy-N-(6-(trifluoromethyl)benzo[d]thiazol-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃; for 48h; [0152] 5-Chloro-2-methoxybenzoic acid (535.0 mg, 2.864 mmol) was dissolved in DCM (15.0 mL), followed by the addition of catalytic amount of DMF (40 .iL) and oxalyl chloride (0.30 mL, 3.437 mmol) respectively. The reaction was allowed to stir at rt for 30 mm and concentrated in vacuo. The residue was re-dissolved in TIIF (10.0 mL), and Hunig?s base (0.50 mL, 2.864 mmol) and 6-(trifluoromethyl)benzo[d]thiazol-2-ammne (500.0 mg, 2.29 1 mmol) were added. The mixture was stirred at rt for 48 hours before it was filtered. The filter cake was washed with diethyl ether and DCM to give 5-chloro-2-methoxy-N-(6-(trifluoromethyl)benzo[d]thiazol-2- yl)benzamide (710.5 mg, 80percent yield). This compound (400.0 mg, 1.034 mmol) was then mixed with pyridinium chloride (4.000 g). The mixture was heated to 210 °C, stirred for 15 minutes and cooled down to rt. The resulting solid was suspended in water and filtered. The filter cake was washed with diethyl ether to give 5-chloro-2-hydroxy-N-(6-(trifluoromethyl)benzo[d]thiazol-2- yl)benzamide 31 (219.1 mg, 57percent yield). ?H NMR (300 MHz, DMSO-d6) 6 8.56 (d, J = 2.2 Hz, 1H), 7.93 (dd, J = 6.2, 4.0 Hz, 2H), 7.84 ?7.72 (m, 1H), 7.55 (dt, J = 8.8, 2.4 Hz, 1H), 7.10 (dd, J = 9.0, 2.0 Hz, 1H). MS (ESI) exact mass calculated for [M+H] (C15H9C1F3N2025) requires m/z 373.0, found m/z 372.7.
  • 8
  • [ 20358-06-9 ]
  • [ 29568-33-0 ]
  • 5-chloro-N-(4-fluorobenzo[d]thiazol-2-yl)-2-methoxybenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In tetrahydrofuran; at 20℃; for 48.0h; [0139] 5-chloro-2-methoxybenzoic acid (186.7 mg, 1.000 mmol) was dissolved in DCM (10.0 mL), followed by the addition of catalytic amount of DMF (20 .iL) and oxalyl chloride (0.10 mL, 1.200 mmol) respectively. The reaction was allowed to stir at rt for 30 mm, concentrated in vacuo, and the residue was then dissolved in THF (10.0 mL).To this flask, was added triethylamine (0.17 mL, 1.200 mmol) followed by <strong>[20358-06-9]4-fluorobenzo[d]thiazol-2-amine</strong> (134.6 mg, 0.800 mmol). The reaction was stirred at rt for 48 h before silica gel was added to quench the reaction. Solvent was evaporated and the resulting residue was purified via silica gel column chromatography to give 5-chloro-N-(4-fluorobenzo[d]thiazol-2-yl)-2-methoxybenzamide (101.1 mg, 38% yield). This amide (50.0 mg, 0.148 mmol) was mixed with pyridinium chloride (1.0 g). The mixture was heated to 200 C, stirred for 10 minutes and cooled down to rt. The resulting solid was suspended in water and filtered. The filter cake was washed with water, acetone and diethyl ether to yield 5-chloro-N-(4-fluorobenzo[d]thiazol-2-yl)-2-hydroxybenzamide 18 (15.0 mg, 31% yield). ?H NMR (300 MHz, DMSO-d6) 6 7.99 - 7.92 (m, 1H), 7.92 - 7.83 (m, 1H), 7.60-7.50 (m, 1H), 7.35 (h, J= 8.1, 7.5 Hz, 2H), 7.11 (d, J= 8.5 Hz, 1H). MS (ESI) exact mass calculated for [M+H] (C14H19C1FN2O2S) requires m/z 323.0, found m/z 322.9.
 

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