1,3-Dihydro-3,3-dimethyl-2H-indol-2-one
- Product Name
- 1,3-Dihydro-3,3-dimethyl-2H-indol-2-one
- CAS No.
- 19155-24-9
- Chemical Name
- 1,3-Dihydro-3,3-dimethyl-2H-indol-2-one
- Synonyms
- 3,3-DiMethyloxindole;Oxindole, 3,3-diMethyl-;3,3-DIMETHYLINDOLIN-2-ONE;3,3-dimethyl-2-indolinone;3,3-dimethyl-3H-indol-2-ol;2-Indolinone, 3,3-diMethyl-;3,3-dimethyl-1H-indol-2-one;3,3-DIMETHYL-1,3-DIHYDRO-INDOL-2-ONE;3,3-diMethyl-2,3-dihydro-1H-indol-2-one;3,3-dimethyl-1,3-dihydro-2H-indol-2-one
- CBNumber
- CB72308789
- Molecular Formula
- C10H11NO
- Formula Weight
- 161.2
- MOL File
- 19155-24-9.mol
1,3-Dihydro-3,3-dimethyl-2H-indol-2-one Property
- Melting point:
- 154.3°C
- Boiling point:
- 287.51°C (rough estimate)
- Density
- 1.078
- refractive index
- 1.5200 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- form
- solid
- pka
- 14.85±0.40(Predicted)
- color
- Yellow
- InChI
- InChI=1S/C10H11NO/c1-10(2)7-5-3-4-6-8(7)11-9(10)12/h3-6H,1-2H3,(H,11,12)
- InChIKey
- KEZHRKOVLKUYCQ-UHFFFAOYSA-N
- SMILES
- N1C2=C(C=CC=C2)C(C)(C)C1=O
Safety
- HS Code
- 2933998090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- D476405
- Product name
- 3,3-Dimethyloxindole
- Packaging
- 500mg
- Price
- $160
- Updated
- 2021/12/16
- Product number
- W4107
- Product name
- 3,3-Dimethylindolin-2-one
- Packaging
- 1g
- Price
- $184
- Updated
- 2021/12/16
- Product number
- FD127080
- Product name
- 3,3-Dimethyl-1,3-dihydro-2H-indol-2-one
- Packaging
- 1g
- Price
- $255
- Updated
- 2021/12/16
- Product number
- FD127080
- Product name
- 3,3-Dimethyl-1,3-dihydro-2H-indol-2-one
- Packaging
- 250mg
- Price
- $85
- Updated
- 2021/12/16
- Product number
- OR964406
- Product name
- 3,3-Dimethylindolin-2-one
- Purity
- 97%
- Packaging
- 1g
- Price
- $145
- Updated
- 2021/12/16
1,3-Dihydro-3,3-dimethyl-2H-indol-2-one Chemical Properties,Usage,Production
Uses
3,3-Dimethyloxindole is used as an isoquinolin-1-amine based ROCK-I inhibitors. Also used in the preparation of a P2Y1 antagonists as effacacious antiplatelet agents.
Synthesis Reference(s)
Tetrahedron, 48, p. 7297, 1992 DOI: 10.1016/S0040-4020(01)88268-5
Synthesis
59-48-3
74-88-4
19155-24-9
To a solution of 2-indolone (5 g, 37.55 mmol) and lithium chloride (5.6 g, 131.4 mmol) in tetrahydrofuran (100 mL) was added n-butyllithium (2.5 M, 30 mL) dropwise at -78 °C. The reaction mixture was stirred at -78 °C for 20 min, followed by the addition of iodomethane (4.8 mL, 75.1 mmol). The reaction system was warmed to 25 °C and stirred overnight. Upon completion of the reaction, the reaction was quenched with saturated aqueous ammonium chloride solution (100 mL) and extracted with ethyl acetate (100 mL x 3). The organic phases were combined, washed sequentially with water (100 mL) and saturated saline (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (petroleum ether/ethyl acetate, 8:1, v/v) to afford 1,2-dihydro-3,3-dimethyl-2-oxo-3H-indole as a white solid (2.92 g, 48.3% yield). Mass spectrum (ESI, positive ion mode) m/z: 162 [M+H]+; NMR hydrogen spectrum (CDCl3) δ (ppm): 9.23 (s, 1H), 7.21-7.18 (m, 2H), 7.04 (t, 1H), 6.96 (d, 1H), 1.41 (s, 6H).
References
[1] Patent: WO2014/89324, 2014, A1. Location in patent: Paragraph 0202
[2] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 18, p. 4929 - 4931
[3] Patent: US2007/72897, 2007, A1. Location in patent: Page/Page column 66
[4] Journal of Medicinal Chemistry, 2016, vol. 59, # 1, p. 419 - 430
[5] ChemMedChem, 2016, vol. 11, # 5, p. 497 - 508
1,3-Dihydro-3,3-dimethyl-2H-indol-2-one Preparation Products And Raw materials
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View Lastest Price from 1,3-Dihydro-3,3-dimethyl-2H-indol-2-one manufacturers
- Product
- 1,3-Dihydro-3,3-dimethyl-2H-indol-2-one 19155-24-9
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- 1Ton
- Release date
- 2022-10-13
- Product
- 1,3-Dihydro-3,3-dimethyl-2H-indol-2-one 19155-24-9
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 200kg
- Release date
- 2020-01-02