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890707-28-5

Basic Information
CAS No.: 890707-28-5
Name: Bardoxolone
Article Data: 26
Molecular Structure:
Molecular Structure of 890707-28-5 (Bardoxolone)
Formula: C9H11ClN2O
Molecular Weight: 198.652
Synonyms: 2-Amino-5-chloro-N,3-dimethylhenzamide
EINECS: 618-233-7
Density: 1.239g/cm3
Melting Point: 130-132 °C
Boiling Point: 308.8 °C at 760 mmHg
Flash Point: 140.5 °C
PSA: 58.61000
LogP: 2.74620
Synthetic route
79101-83-0

2-amino-3-methyl-5-chlorobenzoic acid methyl ester

74-89-5

methylamine

890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
In methanol at 65 - 68℃; for 5h; Temperature;98%
In methanol at 45℃; for 6h;97.2%
In ethylene glycol; acetonitrile at 0 - 70℃; for 17.5 - 23h; Product distribution / selectivity;84.8%

isopropyl 2-amino-5-chloro-3-methylbenzoate

74-89-5

methylamine

890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
In isopropyl alcohol at 60℃; for 7h;96.8%

2-amino-5-chloro-3-methylbenzoic acid ethyl ester

74-89-5

methylamine

890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
In methanol at 50℃; for 6h;95.4%
120374-68-7

6-chloro-8-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

74-89-5

methylamine

890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
With acetic acid In ethyl acetate at 35 - 45℃; for 0.333333h;95%
With acetic acid In ethyl acetate at 22 - 52℃; for 0.333333 - 2.75h; Product distribution / selectivity;93%
With acetic acid In water; acetonitrile at 25 - 30℃; for 2.5h; Product distribution / selectivity;87%
120374-68-7

6-chloro-8-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

593-51-1

methylamine hydrochloride

890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
With potassium hydrogencarbonate In acetonitrile at 25 - 30℃; for 3h; Solvent; Reagent/catalyst; Temperature;93.6%
Stage #1: methylamine hydrochloride With triethylamine In dichloromethane at 20℃; for 2h;
Stage #2: 6-chloro-8-methyl-1H-benzo[d][1,3]oxazine-2,4-dione With acetic acid In dichloromethane; ethyl acetate Reflux;
With potassium carbonate In ethanol at 25 - 80℃; for 5.5h; Reagent/catalyst; Temperature;
20776-67-4

2-amino-5-chloro-3-methylbenzoic acid

74-89-5

methylamine

890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
Stage #1: 2-amino-5-chloro-3-methylbenzoic acid With benzotriazol-1-ol; diisopropyl-carbodiimide In dichloromethane at 20℃; for 2h;
Stage #2: methylamine In dichloromethane at 0℃; for 2h; Temperature;
92.6%
Stage #1: 2-amino-5-chloro-3-methylbenzoic acid With thionyl chloride for 3h; Reflux;
Stage #2: methylamine In tetrahydrofuran; water at 20℃; Cooling with ice;
59.3%
Stage #1: 2-amino-5-chloro-3-methylbenzoic acid With thionyl chloride for 3h; Reflux;
Stage #2: methylamine In tetrahydrofuran; water at 20℃; for 12h; Cooling with ice;
59.3%
120374-68-7

6-chloro-8-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

74-89-5

methylamine

A

890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

B

6-chloro-3,8-dimethyl-2,4(1H,3H)-quinazolinedione

C

20776-67-4

2-amino-5-chloro-3-methylbenzoic acid

Conditions
ConditionsYield
With water; acetic acid In ethyl acetate at 48 - 52℃; for 1h; Product distribution / selectivity;A 87.3%
B 3.4%
C 1.7%
870997-57-2

N-methyl-3-methyl-2-aminobenzamide

890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
With hydrogenchloride; dihydrogen peroxide; acetic acid at 5 - 20℃;85%
Stage #1: N-methyl-3-methyl-2-aminobenzamide With hydrogenchloride In N,N-dimethyl-formamide at 10 - 30℃;
Stage #2: With sodium sulfite In water; N,N-dimethyl-formamide at 30 - 35℃; for 3.25h;
Stage #3: With sodium hydroxide; sodium sulfite In water; N,N-dimethyl-formamide at 10℃; for 0.25h; pH=2.2; Product distribution / selectivity;
72.7%
With N-chloro-succinimide In acetonitrile for 1h; Reflux;
With sulfuryl dichloride In dichloromethane at 0 - 30℃;
With thionyl chloride In acetonitrile at 40 - 50℃;
201230-82-2

carbon monoxide

146948-68-7

2-bromo-4-chloro-6-methylphenylamine

74-89-5

methylamine

890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
palladium diacetate; 1,4-di(diphenylphosphino)-butane In ethylene glycol at 25 - 110℃; under 2842.59 Torr; Inert atmosphere; Sealed tube;70%

2-amino-5-chloro-3-methylbenzoyl chloride

74-89-5

methylamine

890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
In dichloromethane
In dichloromethane
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  • 2-Amino-5-chloro-N,3-dimethylbenzamide

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Specification

The 2-Amino-3-methyl-N-methylbenzamide, with CAS registry number 890707-28-5, has the systematic name of 2-amino-5-chloro-N,3-dimethyl-benzamide. Besides this, it is also called benzamide, 2-amino-5-chloro-N,3-dimethyl-. And the chemical formula of this chemical is C9H11ClN2O.

Physical properties of 2-Amino-3-methyl-N-methylbenzamide: (1)ACD/LogP: 2.15; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.15; (4)ACD/LogD (pH 7.4): 2.15; (5)#H bond acceptors: 3; (6)#H bond donors: 3; (7)#Freely Rotating Bonds: 2; (8)Polar Surface Area: 55.12 Å2; (9)Index of Refraction: 1.586; (10)Molar Refractivity: 53.83 cm3; (11)Molar Volume: 160.2 cm3; (12)Polarizability: 21.34×10-24cm3; (13)Surface Tension: 47 dyne/cm; (14)Density: 1.239 g/cm3; (15)Flash Point: 140.5 °C; (16)Enthalpy of Vaporization: 54.95 kJ/mol; (17)Boiling Point: 308.8 °C at 760 mmHg; (18)Vapour Pressure: 0.000666 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: Cc1cc(cc(c1N)C(=O)NC)Cl
(2)InChI: InChI=1/C9H11ClN2O/c1-5-3-6(10)4-7(8(5)11)9(13)12-2/h3-4H,11H2,1-2H3,(H,12,13)
(3)InChIKey: WOBVZGBINMTNKL-UHFFFAOYAB
(4)Std. 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)
(5)Std. InChIKey: WOBVZGBINMTNKL-UHFFFAOYSA-N