4-Nitroindanone
- Product Name
- 4-Nitroindanone
- CAS No.
- 24623-25-4
- Chemical Name
- 4-Nitroindanone
- Synonyms
- 4-Nitroindanone;Einecs 246-367-2;4-Nitro-1-Indanone;4-Nitroindan-1-one;2,3-Dihydro-4-nitroinden-1-one;4-nitro-2,3-dihydroinden-1-one;2,3-Dihydro-4-nitro-1H-inden-1-one;4-nitro-2,3-dihydro-1H-inden-1-one;1H-Inden-1-one, 2,3-dihydro-4-nitro-;2-(2,5-dimethylphenoxy)-1-cyclohexanone
- CBNumber
- CB2901976
- Molecular Formula
- C9H7NO3
- Formula Weight
- 177.16
- MOL File
- 24623-25-4.mol
4-Nitroindanone Property
- Melting point:
- 104-105 °C
- Boiling point:
- 332.9±31.0 °C(Predicted)
- Density
- 1.396±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- Appearance
- Off white to brown Solid
- InChI
- InChI=1S/C9H7NO3/c11-9-5-4-6-7(9)2-1-3-8(6)10(12)13/h1-3H,4-5H2
- InChIKey
- QIIWEVWPOBNGLP-UHFFFAOYSA-N
- SMILES
- C1(=O)C2=C(C([N+]([O-])=O)=CC=C2)CC1
Safety
- HazardClass
- IRRITANT
- HS Code
- 2914790090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
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
- N587460
- Product name
- 4-Nitroindanone
- Packaging
- 250mg
- Price
- $75
- Updated
- 2021/12/16
- Product number
- N587460
- Product name
- 4-Nitroindanone
- Packaging
- 500mg
- Price
- $110
- Updated
- 2021/12/16
- Product number
- N587460
- Product name
- 4-Nitroindanone
- Packaging
- 1g
- Price
- $180
- Updated
- 2021/12/16
- Product number
- CS-B1085
- Product name
- 4-Nitro-indan-1-one
- Packaging
- 250mg
- Price
- $94
- Updated
- 2021/12/16
- Product number
- 054310
- Product name
- 4-Nitro-1-indanone
- Purity
- >95%
- Packaging
- 1g
- Price
- $208
- Updated
- 2021/12/16
4-Nitroindanone Chemical Properties,Usage,Production
Description
4-Nitroindanone (4-Nitro-1-indanone) is an important chemical reagent used as a raw material in organic synthesis for the preparation of other cyclic compounds. In biology, it can inhibit the cysteine protease thioredoxin reductase and also interacts with cardiac potassium channels and is cytotoxic to human erythrocytes. In a rat model of atrial fibrillation, 4-nitro-1-indanone was found to have antiarrhythmic properties.
Uses
4-Nitroindanone is a versatile building block, capable of undergoing microwave-assisted oxidation to form ninhydrins. 4-Nitroindanone also has pharmaceutical relevance, as its thiosemicarbazone derivative has anti-Trypanosoma cruzi properties.
Synthesis
83-33-0
24623-25-4
24623-24-3
General procedure for the synthesis of 4-nitro-1-indanone and 6-nitro-1-indanone from 1-indanone: To a well-stirred mixture of concentrated sulfuric acid (98%, 13.9 mL) and nitric acid (65%, 2.6 mL) at -10°C, a solution of nitromethane (1.1 mL) with 1-indanone (1.0 g, 7.6 mmol) was slowly added. The rate of addition was controlled so that the temperature increased from -10°C to -5°C in 30 minutes. Stirring of the reaction mixture was continued at this temperature for 15 minutes (tight control of temperature and reaction time is required). Upon completion of the reaction, the mixture was poured into ice water (200 mL) for hydrolysis and the resulting yellow precipitate was collected. The aqueous phase was extracted with dichloromethane (2 x 20 mL) and the organic phase was combined. The organic phase was washed sequentially with potassium bicarbonate solution (2 x 15 mL) and saturated brine (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by fast column chromatography using hexane-ethyl acetate (1:0.2) as eluent. Isolation afforded 4-nitro-1-indanone (compound 25, 0.94 g, 80% yield) with a melting point of 98-100 °C (literature value: 100-101 °C).1H NMR (CDCl3) δ ppm: 2.80 (m, 2H, CH2), 3.53 (m, 2H, CH2), 7.61 (m, 1H, H-Ar), 8.08 (d, J = 8.5 Hz, 1H, H-Ar), 8.47 (d, J = 8.3 Hz, 1H, H-Ar). Simultaneous isolation afforded 6-nitro-1-indanone (compound 26, 0.23 g, 20% yield) with a melting point of 73-74 °C (literature value: 72-73 °C).1H NMR (CDCl3) δ ppm: 2.83 (m, 2H, CH2), 3.28 (m, 2H, CH2), 7.61 (d, J = 8.5 Hz, 1H, H-Ar) 8.44 (dd, J = 2.2 Hz, J = 8.5 Hz, 1H, H-Ar), 8.56 (d, J = 2.2 Hz, 1H, H-Ar).
References
[1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 22, p. 6818 - 6826
[2] Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 399 - 408
[3] Polish Journal of Chemistry, 2008, vol. 82, # 11, p. 2133 - 2140
[4] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 12, p. 3337 - 3339
[5] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 4, p. 884 - 889
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View Lastest Price from 4-Nitroindanone manufacturers
- Product
- 4-Nitroindanone 24623-25-4
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 20 tons
- Release date
- 2025-07-24
- Product
- 4-Nitroindanone 24623-25-4
- Price
- US $0.00/KG
- Min. Order
- 1g
- Purity
- 98%minHPLC
- Supply Ability
- 50kgs/month
- Release date
- 2021-11-14
- Product
- 4-Nitroindanone 24623-25-4
- Price
- US $7.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 100KG
- Release date
- 2019-12-30