| Identification | More | [Name]
2'-AMINOACETANILIDE | [CAS]
34801-09-7 | [Synonyms]
2'-AMINOACETANILIDE
2-AMINOACETANILIDE
O-AMINOACETANILIDE
Acetamide, N-(2-aminophenyl)-
Acetamide, N-(2-aminophenyl)-(9CI) | [Molecular Formula]
C8H10N2O | [MDL Number]
MFCD00210388 | [Molecular Weight]
150.18 | [MOL File]
34801-09-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
133-137 °C(lit.) | [Boiling point ]
271.72°C (rough estimate) | [density ]
1.1392 (rough estimate) | [refractive index ]
1.6180 (estimate) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [form ]
powder to crystalline | [pka]
14.73±0.70(Predicted) | [color ]
Light orange to Light red | [Water Solubility ]
107.5g/L(22 ºC) | [InChI]
1S/C8H10N2O/c1-6(11)10-8-5-3-2-4-7(8)9/h2-5H,9H2,1H3,(H,10,11) | [InChIKey]
MPXAYYWSDIKNTP-UHFFFAOYSA-N | [SMILES]
CC(=O)Nc1ccccc1N | [CAS DataBase Reference]
34801-09-7(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 | [HazardClass ]
IRRITANT | [HS Code ]
2924297099 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
White Powder | [Uses]
2′-Aminoacetanilide may be used in the preparation of:
- 2-Methylbenzimidazole.
- N-(2-(1,3-Dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)phenyl)-5-methylfuran-2-carboxamide, a potent cystic fibrosis transmembrane conductance regulator (CFTR) inhibitor.
- Azobenzothiazole dyes, N-[2-(6-nitrobenzothiazol-2-ylazo)phenyl]acetamide and N-[2-(benzothiazol-2-ylazo)phenyl]acetamide.
| [General Description]
2′-Aminoacetanilide (2-aminoacetanilide, o-aminoacetanilide) can be prepared by the catalytic hydrogenation of 2-nitroacetanilide using 10%Pd/C (palladium/carbon). | [Synthesis]
The general procedure for the synthesis of 2'-aminoacetanilide from 2-nitroacetanilide was as follows: first, 2-nitroacetanilide (1.0 g, 5.6 mmol) was dissolved in ethanol (EtOH) and the solution was purged with nitrogen to remove oxygen. Subsequently, palladium hydroxide (Pd(OH)2, 20% by weight, carbon carrier, 200 mg) was added to the solution as a catalyst. The reaction mixture was shaken under hydrogen (H2, 20 psi) atmosphere for 2 hours. Upon completion of the reaction, it was filtered through a 0.22 μm cellulose acetate membrane (Corning) to remove the catalyst. The filtrate was concentrated under vacuum to afford the white crystalline solid product 2'-aminoacetanilide (800 mg, 96% yield). The structure of the product was confirmed by 1H NMR (300 MHz, d6-DMSO) and LRMS (ES pos.): 1H NMR δ: 9.12 (s, 1H), 7.14 (dd, J = 7.8,1.3 Hz, 1H), 6.88 (dt, J = 7.6,1.5 Hz, 1H), 6.70 (dd, J = 8.0,1.3 Hz, 1H), 6.52 (dt, J = 7.5,1.4 Hz, 1H), 4.85 (br s, 2H), 2.03 (s, 3H); LRMS (ES pos.) m/z = 151 (M + 1). | [References]
[1] Journal of Organic Chemistry, 2008, vol. 73, # 23, p. 9235 - 9244
[2] Patent: US6667300, 2003, B2. Location in patent: Page column 98
[3] Chemistry - A European Journal, 2015, vol. 21, # 26, p. 9493 - 9504
[4] Russian Journal of Organic Chemistry, 1997, vol. 33, # 11, p. 1676 - 1677
[5] Russian Journal of Organic Chemistry, 1997, vol. 33, # 11, p. 1676 - 1677 |
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