| Identification | More | [Name]
2-Amino-4-methylbenzonitrile | [CAS]
26830-96-6 | [Synonyms]
2-AMINO-4-METHYLBENZONITRILE
4-Methyl-2-aminobenzonitrile | [EINECS(EC#)]
248-020-0 | [Molecular Formula]
C8H8N2 | [MDL Number]
MFCD00173706 | [Molecular Weight]
132.16 | [MOL File]
26830-96-6.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powder | [Melting point ]
92-95 °C (lit.) | [Boiling point ]
150-152 °C(Press: 15 Torr) | [density ]
1.10±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
soluble in Methanol | [form ]
Powder | [pka]
1.94±0.10(Predicted) | [color ]
Light yellow to Yellow to Orange | [CAS DataBase Reference]
26830-96-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,T | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
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 .
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
3439 | [WGK Germany ]
3
| [Hazard Note ]
Toxic | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29269090 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powder | [Uses]
2-Amino-4-methylbenzonitrile was used in the synthesis of:
- 7-methyl-4-(phenylamino)quinazoline-2(1H)-selone
- racemic aminoquinolines, potential acetylcholinesterase (AChE) inhibitors
| [Synthesis]
a) Synthesis of 2-amino-4-methylbenzonitrile
4-Methyl-2-nitrobenzonitrile (4.9 g, 30 mmol) was mixed with 10% palladium-carbon catalyst (500 mg) in 1,4-dioxane (60 mL), and the reaction was stirred overnight under a hydrogen atmosphere (balloon pressurized). Upon completion of the reaction, the catalyst was removed by diatomaceous earth filtration and the filtrate was concentrated under reduced pressure to give the crude product. The crude product was further purified by fast column chromatography (eluent: dichloromethane) to afford 2-amino-4-methylbenzonitrile as a light yellow solid (3.3 g, 83% yield).
1H-NMR (300 MHz, CDCl3) δ 7.26 (d, J = 8.3 Hz, 1H), 6.56 (s, 1H), 6.55 (s, 1H), 4.32 (br s, 2H), 2.29 (s, 3H). | [References]
[1] Chemical Communications, 2011, vol. 47, # 31, p. 8808 - 8810
[2] Journal of the Chemical Society, Perkin Transactions 2, 2001, # 2, p. 214 - 228
[3] Patent: US5891909, 1999, A
[4] Patent: EP906091, 2006, B1. Location in patent: Page/Page column 46
[5] Journal fuer Praktische Chemie (Leipzig), 1889, vol. <2> 40, p. 12 |
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