| Identification | More | [Name]
2-Methyl-3-nitro-benzeneacetic acid | [CAS]
23876-15-5 | [Synonyms]
2-METHYL-3-NITRO-BENZENEACETIC ACID
2-METHYL-3-NITROPHENYLACETIC ACID
(3-NITRO-O-TOLYL)ACETIC ACID
2-METHYL-3-NITROPHENYL ACETIC ACID (R4)
2-Methyl-3-nitrohenylacetic acid
Ropinirole Intermediate 1
(2-Methyl-3-nitro-phenyl)-acetic acid 98%
| [Molecular Formula]
C9H9NO4 | [MDL Number]
MFCD07782132 | [Molecular Weight]
195.17 | [MOL File]
23876-15-5.mol |
| Chemical Properties | Back Directory | [Melting point ]
132-136 °C | [Boiling point ]
377.6±27.0 °C(Predicted) | [density ]
1.346±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
soluble in Methanol | [form ]
Solid | [pka]
4.05±0.10(Predicted) | [color ]
White to Light yellow to Light orange | [InChI]
InChI=1S/C9H9NO4/c1-6-7(5-9(11)12)3-2-4-8(6)10(13)14/h2-4H,5H2,1H3,(H,11,12) | [InChIKey]
LWIOFILTAJJDLA-UHFFFAOYSA-N | [SMILES]
C1(CC(O)=O)=CC=CC([N+]([O-])=O)=C1C | [CAS DataBase Reference]
23876-15-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [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:Wear suitable protective clothing . | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HS Code ]
29163990 |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow solid | [Uses]
2-Methyl-3-nitrophenylacetic Acid is a pharmaceutical intermediate compound used in the preparation of ropinirole hydrochloride, an oral non-ergot alkaloid dopamine agonist used to treat the symptoms of Parkinson's disease and restless legs syndrome. | [Synthesis]
General procedure for the synthesis of 2-methyl-3-nitrophenylacetic acid from 2-methyl-3-nitrobenzonitrile: To a solution of 2-methyl-3-nitrophenylacetonitrile (500 mg, 2.8 mmol) in ethanol (30 mL) was added a 20% w/v aqueous KOH solution (30 mL). The reaction mixture was heated to reflux for 18 hours. After completion of the reaction, it was cooled to room temperature and extracted with dichloromethane (50 mL) to separate the aqueous layer. The aqueous layer was acidified to pH 2 with 2N HCl aqueous solution and subsequently extracted with ethyl acetate (50 mL) and dichloromethane (50 mL). The organic phases were combined, dried over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure to afford the light brown solid product 2-methyl-3-nitrophenylacetic acid (470 mg, 86% yield). The product was characterized by 1H NMR (400 MHz, CD3OD) with chemical shifts δ (ppm) of 7.66 (d, 1H), 7.50 (d, 1H), 7.34 (t, 1H), 3.79 (s, 2H), 2.37 (s, 3H). | [References]
[1] Journal of Medicinal Chemistry, 1985, vol. 28, # 10, p. 1533 - 1536
[2] Patent: US2005/267096, 2005, A1. Location in patent: Page/Page column 29
[3] Journal of the Chemical Society. Perkin transactions 1, 1969, vol. 14, p. 1935 - 1939
[4] Journal of the Chemical Society. Perkin transactions 1, 1969, vol. 14, p. 1935 - 1939
[5] Patent: WO2006/123356, 2006, A1. Location in patent: Page/Page column 22; 23 |
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