Bardoxolone
- Product Name
- Bardoxolone
- CAS No.
- 890707-28-5
- Chemical Name
- Bardoxolone
- Synonyms
- 2-Amino-5-chloro-N,3-dimethylbenzamide;cas 890707-28-5 98%;Bardoxolone Powder C9h11cln2o;cas 890707-28-5 Coragen intermediate;cas 890707-28-5 98% Coragen intermediate;Benzamide, 2-amino-5-chloro-N,3-dimethyl-;2-Amino-5-chloro-N,3-dimethylbenzamide 98%;2-Amino-5-chloro-N,3-dimethylbenzamide, 95+%
- CBNumber
- CB72501263
- Molecular Formula
- C9H11ClN2O
- Formula Weight
- 198.65
- MOL File
- 890707-28-5.mol
Bardoxolone Property
- Melting point:
- 130-132 °C
- Boiling point:
- 308.8±42.0 °C(Predicted)
- Density
- 1.239
- vapor pressure
- 0-0Pa at 20-25℃
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
- pka
- 14.24±0.46(Predicted)
- form
- Solid
- color
- Off-White to Light Brown
- InChI
- InChI=1S/C9H11ClN2O/c1-5-3-6(10)4-7(8(5)11)9(13)12-2/h3-4H,11H2,1-2H3,(H,12,13)
- InChIKey
- WOBVZGBINMTNKL-UHFFFAOYSA-N
- SMILES
- C(NC)(=O)C1=CC(Cl)=CC(C)=C1N
- LogP
- 1.7 at 25℃
- Surface tension
- 67.8mN/m at 249.3mg/L and 20.4℃
Safety
- HS Code
- 29242990
N-Bromosuccinimide Price
- Product number
- FA159371
- Product name
- 2-Amino-5-chloro-N,3-dimethylbenzamide
- Packaging
- 1g
- Price
- $60
- Updated
- 2021/12/16
- Product number
- FA159371
- Product name
- 2-Amino-5-chloro-N,3-dimethylbenzamide
- Packaging
- 2g
- Price
- $90
- Updated
- 2021/12/16
- Product number
- FA159371
- Product name
- 2-Amino-5-chloro-N,3-dimethylbenzamide
- Packaging
- 5G
- Price
- $120
- Updated
- 2021/12/16
- Product number
- FA159371
- Product name
- 2-Amino-5-chloro-N,3-dimethylbenzamide
- Packaging
- 10g
- Price
- $180
- Updated
- 2021/12/16
- Product number
- FA159371
- Product name
- 2-Amino-5-chloro-N,3-dimethylbenzamide
- Packaging
- 25g
- Price
- $250
- Updated
- 2021/12/16
Bardoxolone Chemical Properties,Usage,Production
Chemical Properties
Off-white powder
Uses
Bardoxolone is a synthetic oleanane triterpenoid that exerts multifunctional activities in the control of cellular growth and differentiation. Bardoxolone is capable of activating the transcription factor peroxisome proliferator activator receptor-γ (PPARγ), its apoptotic effects in malignant cells have been shown to occur independently of PPARγ. Bardoxolone was developed as an potential drug for the improvement of hyperglycemia, proteinuria, glomerulus structure, serum creatine, which may in turn be beneficial to treat diabetic kidney diseases, cancer and thromboembolic events.
Synthesis
20776-67-4
74-89-5
890707-28-5
First, 15 g of toluene and 50 mL of dichloromethane were sequentially added to a 200 mL autoclave. Subsequently, 0.1 g of N-hydroxyphthalimide and 0.4 g of cobalt acetylacetonate were dissolved in the above mixed solvents and stirred thoroughly. After sealing the autoclave, the air in the autoclave was replaced with oxygen for 3 times, and then pressurized to 3 MPa. The temperature of the reaction system was raised to 30 °C and kept at this temperature for 1 hour. After the reaction was completed, the mixture was cooled to room temperature and filtered to obtain a solution containing benzoic acid. The above filtrate was transferred to a 1000 mL four-necked flask equipped with a thermometer, 100 mL of glacial acetic acid was added, stirred and protected by passing nitrogen gas. The reaction temperature was raised to 40 °C, and then 30 mL of chlorine gas was added dropwise at a rate of 10 mL/min, while the temperature of the reaction solution was controlled to be 30 °C by an oil bath for 3 hours to obtain a solution containing 3,5-dichlorobenzoic acid. To this solution, 3 g of dimethylmercury was added as a shielding agent, and after stirring for 5 minutes, 10 g of Format reagent was added and the reaction was carried out for 1 hour to obtain a solution containing 3-methyl-5-chlorobenzoic acid. Under the condition of an ice bath, the temperature of the solution was controlled to be 0°C, and 5 mL of 98% concentrated sulfuric acid was added to the above solution at a rate of 5 mL/min, followed by the slow addition of 20 mL of 1 mol/L nitric acid, and the temperature of the reaction was controlled to be at 40°C. After the reaction was carried out for 1 hour, a solution containing 2-nitro-3-methyl-5-chlorobenzoic acid was obtained. The above solution was transferred to another 1000 mL four-necked flask equipped with a thermometer and 1 g of zinc flakes and 40 mL of 0.1 mol/L NaOH solution were added. The reaction temperature was controlled to be 70°C via an oil bath and the reaction was stirred for 2 hours to obtain a solution containing 2-amino-3-methyl-5-chlorobenzoic acid. At the end of the reaction, 100 mL of dichloromethane, 40 mL of N,N'-diisopropylcarbodiimide and 5 mL of 1-hydroxybenzotriazole were added to the solution and stirred for 2 hours at room temperature. Then 40 mL of methylamine was added dropwise at a rate of 10 mL/min under ice-water bath conditions, and after the dropwise addition was completed, the reaction was kept for 2 hours to obtain a solution containing 2-amino-5-chloro-N,3-dimethylbenzamide. Finally, the reaction solution was extracted with 100 mL of deionized water and 100 mL of dichloromethane, and the organic phases were combined and purified by column chromatography (eluent was a mixture of petroleum ether:ethyl acetate=1:10) to obtain a solution of the target product, 2-amino-5-chloro-N,3-dimethylbenzamide. In this method, N-hydroxyphthalimide and cobalt acetylacetonate were used as catalysts to efficiently oxidize toluene to benzoic acid under mild conditions. Meanwhile, the use of N,N'-diisopropylcarbodiimide as a condensation agent and 1-hydroxybenzotriazole as a condensation activator avoided the use of phosgene gas, simplified the synthesis steps, and significantly increased the yield to 92.6%.
References
[1] Patent: CN105859574, 2016, A. Location in patent: Paragraph 0007
[2] Chinese Journal of Chemistry, 2012, vol. 30, # 8, p. 1748 - 1758
[3] Research on Chemical Intermediates, 2013, vol. 39, # 7, p. 3071 - 3088
[4] Journal of Heterocyclic Chemistry, 2016, vol. 53, # 4, p. 1036 - 1045
[5] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 17, p. 4968 - 4975
Bardoxolone Preparation Products And Raw materials
Raw materials
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View Lastest Price from Bardoxolone manufacturers
- Product
- 2-Amino-5-chloro-N,3-dimethylbenzamide 890707-28-5
- Price
- US $30.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- Ex 20 tons
- Release date
- 2022-09-16
- Product
- Bardoxolone 890707-28-5
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- kg/T
- Release date
- 2019-12-18