| Identification | More | [Name]
5-Methyl-2-[(2-nitrophenyl)amino]thiophene-3-carbonitrile | [CAS]
138564-59-7 | [Synonyms]
2-(2'-NITROANILINE)-3-CYANO-5-METHYL THIOPHENE
2-(2-NITROANILINO)-5-METHYL-3-THIOPHENECARBONITRILE
3-CYANO-5-METHYL-2-(2-NITROANILINO)THIOPHENE
2-(2-Nitro Anilino)-5-Methyl Thiophene-3-Carbonitrile
2-(2'-NITROPHENYLAMINE)-3-CYANO-5-METHYLTHIOFURAN
5-methyl-2-((2-nitrophenyl)amino)-3-thiophenecarbonitrile
5-METHYL-2-[(2-NITROPHENYL)AMINO]THIOPHENE-3-CARBONITRILE
2-(2-NITROANILINO)-5-METHYL THIOPHENE-3-CARBONITRILE 98.0+%
2-(NITROANILINO)-5-METHYLTHIOPHENE-3-CARBONITRILE | [EINECS(EC#)]
421-300-1 | [Molecular Formula]
C12H9N3O2S | [MDL Number]
MFCD06408054 | [Molecular Weight]
259.28 | [MOL File]
138564-59-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
109.0 to 115.0 °C | [Boiling point ]
425.4±45.0 °C(Predicted) | [density ]
1.39±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
Chloroform (Slightly), DMSO (Slightly) | [form ]
neat | [pka]
-3.24±0.50(Predicted) | [color ]
Light yellow to Amber to Dark green | [BRN ]
7485862 | [Major Application]
pharmaceutical small molecule | [InChI]
InChI=1S/C12H9N3O2S/c1-8-6-9(7-13)12(18-8)14-10-4-2-3-5-11(10)15(16)17/h2-6,14H,1H3 | [InChIKey]
NPXUFPFFHANGDL-UHFFFAOYSA-N | [SMILES]
C1(NC2=CC=CC=C2[N+]([O-])=O)SC(C)=CC=1C#N | [CAS DataBase Reference]
138564-59-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
N | [Risk Statements ]
22-50/53 | [Safety Statements ]
22-60-61 | [RIDADR ]
UN 3077 9 / PGIII | [WGK Germany ]
WGK 3 | [HazardClass ]
9 | [PackingGroup ]
III | [HS Code ]
2934990002 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Aquatic Acute 1
Aquatic Chronic 1 |
| Hazard Information | Back Directory | [Chemical Properties]
Red Solid | [Uses]
5-Methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile is an impurity of Olanzapine (O253750). Olanzapine impurity A (EP). | [Synthesis]
A solution of 1-fluoro-2-nitrobenzene (34.5 g, 244 mmol) and 2-amino-3-cyano-5-methylthiophene (33.1 g, 240 mmol) in anhydrous THF (160 mL) was added slowly and dropwise to a vigorously stirred anhydrous tetrahydrofuran (THF, 100 mL) suspension of sodium hydride (NaH, 13.5 g, 60% dispersed in mineral oil, 336 mmol), cooled in an ice bath, and under nitrogen protection. mmol) in a solution of anhydrous THF (160 mL). After dropwise addition, the reaction mixture was stirred at room temperature for 10 hours. Subsequently, additional sodium hydride (NaH, 1.53 g, 95%, 72 mmol) was slowly added to the reaction mixture and stirring was continued for 8 hours at room temperature. Upon completion of the reaction, the mixture was poured into crushed ice and the pH was adjusted to 8 with saturated ammonium chloride (NH4Cl) solution. the precipitate was collected by filtration and dried to give the crude product. The crude product was purified by silica gel column chromatography (eluent: 10% ethyl acetate/hexane) to afford 2-(2-nitroanilino)-3-cyano-5-methylthiophene (47.9 g, 77% yield) as a dark solid. Thin layer chromatography (TLC) Rf value was 0.62 (25% ethyl acetate/hexane). The melting point is 105-107°C. Nuclear magnetic resonance hydrogen spectrum (1H NMR, CDCl3): δ 2.47 (d, J = 1.0 Hz, 3H, CH3), 6.78 (q, J = 1.0 Hz, 1H, Ar-H), 6.95 (ddd, J = 1.0, 7.0, 8.5 Hz, 1H, Ph-H), 7.18 (dd, J = 1.0, 8.5 Hz, 1H, Ph-H) , 7.50 (dd, J = 1.5, 7.0, 8.5 Hz, 1H, Ph-H), 8.24 (dd, J = 1.5, 8.5 Hz, 1H, Ph-H), 9.61 (s, 1H, NH). Mass spectrum (MS, ESI): m/z 258 ([M-H]? , 100%). | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 7, p. 1953 - 1956
[2] Patent: US2010/266711, 2010, A1. Location in patent: Page/Page column 14
[3] Patent: WO2008/50341, 2008, A2. Location in patent: Page/Page column 33
[4] Patent: WO2004/94390, 2004, A1. Location in patent: Page 13-14
[5] Russian Journal of Bioorganic Chemistry, 2005, vol. 31, # 4, p. 378 - 382 |
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