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4-(Oxazol-5-yl)aniline

4-(Oxazol-5-yl)aniline structure

CAS No:
1008-95-3
Formula:
C9H8N2O
Chemical Name:
4-(Oxazol-5-yl)aniline
Synonyms:
Benzenamine,4-(5-oxazolyl)-;Oxazole,5-(p-aminophenyl)-;4-(5-Oxazolyl)benzenamine;4-(1,3-Oxazol-5-yl)aniline;4-(1,3-Oxazol-5-yl)phenylamine;5-(4-Aminophenyl)oxazole;4-(Oxazol-5-yl)phenylamine;4-(Oxazol-5-yl)aniline
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

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4-(Oxazol-5-yl)aniline Basic Attributes

Molecular Weight：

160.176

Exact Mass：

160.17

DSSTox ID：

DTXSID30333712

HScode：

2934999090

Characteristics

PSA：

XLogP3：

1.3

Density：

1.204±0.06 g/cm3(Predicted)

Melting Point：

151-152 °C

Boiling Point：

318.7±17.0 °C(Predicted)

Flash Point：

146.5ºC

Refractive Index：

1.599

Safety Information

Hazard category：

IRRITANT

hazard class code：

R36/37/38

safety instructions：

26-36/37/39

Marks：

Xi,Xn

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

4-(Oxazol-5-yl)aniline Use and Manufacturing

To a solution of 5-(4-nitro-phenyl)-oxazole (500mg, 2.6mmol) in ethanol (10ml) was added tin (620mg, 5.2mmol), followed by dropwise addition of concentrated hydrochloric acid (ImI) and then the reaction was stirred at room temperature for 2hr. The reaction mixture was filtered and the filtrate evaporated to dryness. The resultant residue was diluted with water (10ml), basified with saturated bicarbonate solution, then extracted with ethyl acetate. The organic layer was separated, washed with water, dried and concentrated to dryness to yield 4-oxazol-5-yl-phenylamine (380mg, 90percent) as solid.To a solution of 5-(4-nitro-phenyl)-oxazole (500mg, 2.6mmol) in ethanol (10ml) was added tin (620mg, 5.2mmol), followed by dropwise addition of concentrated hydrochloric acid (ImI) and then the reaction was stirred at room temperature for 2hr. The reaction mixture was filtered and the filtrate evaporated to dryness. The resultant residue was diluted with water (10ml), basified with saturated bicarbonate solution, then extracted with ethyl acetate. The organic layer was separated, washed with water, dried and concentrated to dryness to yield 4-oxazol-5-yl-phenylamine (380mg, 90percent) as solid.[00516] To a solution of 5-(4-nitrophenyl)oxazole (400 mg, 2.10 mmol) in EtOH (5 mL) was added Fe (62 mg, l lmmol) and HCl (2ml, 6N) at 0 °C. The reaction was stirred at 0 °C for 1 h and then at 25 °C for 16 h. The solution was diluted with DCM (20 mL) and neutralized with NaHC03 to pH 7 (10 mL x 2), dried (Na2S04), filtered and concentrated in vacuo, the crude product was purified by chromatography (silica, ethyl acetate/petroleum ether =1/1) to afford 4-(oxazol-5-yl)benzenamine (300 mg, 1.87 mmol, 89percent) as a yellow solid. ESI-MS (EI+, m/z): 161.2 [M+H]+.

Computed Properties

Molecular Weight:160.17
XLogP3:1.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:160.063662883
Monoisotopic Mass:160.063662883
Topological Polar Surface Area:52
Heavy Atom Count:12
Complexity:144
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes