| Identification | More | [Name]
5-CARBOXYOXINDOLE | [CAS]
102359-00-2 | [Synonyms]
5-CARBOXYOXINDOLE
OXINDOLE-5-CARBOXYLIC ACID
RARECHEM AL BO 0983
2-Oxo-indoline-5-carboxylic acid
5-CARBOXY-2-OXINDOLE
5-Carboxyoxindole 97%
2-Oxindole-5-carboxylic acid | [Molecular Formula]
C9H7NO3 | [MDL Number]
MFCD03411961 | [Molecular Weight]
177.16 | [MOL File]
102359-00-2.mol |
| Chemical Properties | Back Directory | [Melting point ]
310-316°C | [Boiling point ]
459.8±45.0 °C(Predicted) | [density ]
1.433±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly, Heated) | [form ]
Solid | [pka]
4.19±0.20(Predicted) | [color ]
Off-White to Light Orange | [InChI]
InChI=1S/C9H7NO3/c11-8-4-6-3-5(9(12)13)1-2-7(6)10-8/h1-3H,4H2,(H,10,11)(H,12,13) | [InChIKey]
LLLKBUWXODIMEW-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=C(C(O)=O)C=C2)CC1=O | [CAS DataBase Reference]
102359-00-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302-H317 | [Precautionary statements ]
P280 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [Hazard Note ]
Irritant | [HS Code ]
2933790090 |
| Hazard Information | Back Directory | [Synthesis]
The general procedure for the synthesis of 2-oxoindoline-5-carboxylic acid from 5-chloroacetylindone was as follows (Example 13, from Table 3): 6.7 g of 2-hydroxyindole acid was slowly added to a stirred suspension of 30 mL of dichloroethane containing 23 g of aluminum chloride under ice bath conditions. Subsequently, 11.3 g of chloroacetyl chloride was slowly added dropwise, during which hydrogen chloride gas was released. The reaction mixture was stirred for 10 minutes and then gradually warmed to 40-50°C and maintained at this temperature for 1.5 hours. The progress of the reaction was monitored by thin layer chromatography (unfolding agent: ethyl acetate, stationary phase: silica gel) to confirm complete consumption of the raw materials. Upon completion of the reaction, the mixture was cooled to room temperature and carefully poured into ice water. The resulting precipitate was collected by vacuum filtration, washed with water and dried under vacuum to give 10.3 g (98% yield) of 5-chloroacetyl-2-hydroxyindole as an off-white solid. | [References]
[1] Patent: US6878733, 2005, B1. Location in patent: Page/Page column 220
[2] Patent: US6878733, 2005, B1. Location in patent: Page/Page column 172
[3] Patent: US6350754, 2002, B2. Location in patent: Page column 24
[4] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 3, p. 745 - 750
[5] Chemical and Pharmaceutical Bulletin, 1988, vol. 36, # 6, p. 2253 - 2258 |
|
|