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| CAS No.: | 2688-84-8 |
|---|---|
| Name: | 2-Phenoxyaniline |
| Molecular Structure: | |
|
|
|
| Formula: | C12H11NO |
| Molecular Weight: | 185.225 |
| Synonyms: | Aniline,o-phenoxy- (6CI,7CI,8CI);2-Aminodiphenyl ether;2-Phenoxybenzenamine;2-Phenoxyphenylamine;NSC 39655;o-Aminodiphenyl ether;o-Aminophenyl phenyl ether;o-Phenoxyaniline; |
| EINECS: | 220-254-8 |
| Density: | 1.141 g/cm3 |
| Melting Point: | 47-49 °C(lit.) |
| Boiling Point: | 296.4 °C at 760 mmHg |
| Flash Point: | 131.8 °C |
| Appearance: | White to light yellow crystal powder |
| Hazard Symbols: |
 Xn, Xi
|
| Risk Codes: | 20/21/22-36/37/38-22 |
| Safety: | 26-37/39-36/37/39-36 |
| PSA: | 35.25000 |
| LogP: | 3.64230 |
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| Conditions | Yield |
|---|---|
| With hydrogen; palladium on activated charcoal In ethanol under 2844.3 Torr; for 6h; | 99% |
| With palladium 10% on activated carbon; hydrazine In ethanol; water at 70 - 80℃; for 1.5h; Large scale; | 99% |
| With palladium on activated charcoal; hydrogen In methanol at 20 - 50℃; for 0.5h; | 98% |
| Conditions | Yield |
|---|---|
| With copper; caesium carbonate at 140℃; for 3h; Inert atmosphere; | 93% |
| Conditions | Yield |
|---|---|
| With copper(l) iodide; 1-(dimethylamino-1-yl-pyridin-2-yl-methyl)naphthalen-2-ol; potassium carbonate In dimethyl sulfoxide at 120℃; for 24h; Ullmann Condensation; Green chemistry; | 91% |
| With sodium dodecyl-sulfate; potassium carbonate In water at 80℃; under 760.051 Torr; for 9h; Ullmann Condensation; Green chemistry; chemoselective reaction; | 79% |
| With copper; caesium carbonate In N,N-dimethyl acetamide at 140℃; |
| Conditions | Yield |
|---|---|
| With sodium dodecyl-sulfate; potassium carbonate In water at 80℃; under 760.051 Torr; for 9h; Ullmann Condensation; Green chemistry; chemoselective reaction; | 76% |
| Conditions | Yield |
|---|---|
| Stage #1: diphenylether With pyridine; trifluorormethanesulfonic acid; tetrabutylammonium tetrafluoroborate In acetonitrile at 25℃; Electrochemical reaction; Stage #2: With piperidine In acetonitrile at 80℃; for 12h; Electrochemical reaction; Overall yield = 92 %; | A 53% B 40% |
| With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 3,6‐di‐tert‐butyl‐9‐mesityl‐10‐phenylacridin‐10‐ium tetrafluoroborate; oxygen; ammonium carbamate In water; 1,2-dichloro-ethane at 23℃; for 24h; Irradiation; Overall yield = 62 %; regioselective reaction; |
- 62926-91-4
N-(2-chlorophenyl)-2,2,2-trifluoro-acetamide
- 108-95-2
phenol
A
- 311764-69-9
2,2,2-trifluoro-N-(2-phenoxyphenyl)acetamide
B
- 2688-84-8
2-phenoxyaniline
| Conditions | Yield |
|---|---|
| With copper(l) iodide; dimethylaminoacetic acid; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 27h; Ullmann reaction; | A 40% B 14% |
- 101-84-8
diphenylether
A
- 101-80-4
4,4'-oxydiphenylene diamine
B
- 139-59-3
4-phenoxyanilin
C
- 2688-84-8
2-phenoxyaniline
| Conditions | Yield |
|---|---|
| With O-(4-nitrobenzoyl)hydroxylammonium trifluoromethanesulfonate; iron(II) bromide; silver(I) triflimide In 2,2,2-trifluoroethanol; water at 30℃; for 2h; | A 19.8% B 19.8% C 39.5% |
| Conditions | Yield |
|---|---|
| (i) DMF, (ii) H2, Raney-Ni; Multistep reaction; |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 93 percent / KOH / 2.5 h / 110 - 120 °C 2: 58 percent / H2 / Pd/C / methanol / 12 h / 20 °C View Scheme |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 93 percent / KOH / 2.5 h / 110 - 120 °C 2: 58 percent / H2 / Pd/C / methanol / 12 h / 20 °C View Scheme | |
| Multi-step reaction with 2 steps 1.1: t-BuOK / tetrahydrofuran / 1 h 1.2: tetrahydrofuran 2.1: H2 / Raney Ni / tetrahydrofuran View Scheme |
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Chemistry
o-PHENOXYANILINE(2688-84-8) ( also named 2-Aminophenyl phenyl ether) is the chemical compound with the formula C12H11NO .Its molar weight is 185.22.
o-PHENOXYANILINE(2688-84-8) molecular Structure is
.
CAS Registry Number:2688-84-8
EINECS:220-254-8
Melting point:46-50 oC
Boiling point:170 oC (18 mmHg)
Flash point:113 oC
Uses
Toxicity Data With Reference
| 1. | ivn-mus LD50:212 mg/kg | TXCYAC Toxicology. 8 (1977),347. |
Consensus Reports
Safety Profile
Hazard symbols: Xn,Xi
Risk statements: 20/21/22-36/37/38-22
20/21/22: Harmful by inhalation, in contact with skin and if swallowed
36/37/38: Irritating to eyes, respiratory system and skin
Safety statements: 26-37/39-36/37/39-36
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
37/39: Wear suitable gloves and eye/face protection
36/37/39: Wear suitable protective clothing, gloves and eye/face protection
36: Wear suitable protective clothing
WGK Germany: 3
RTECS: BY7940000
Hazard Note: Irritant
HazardClass: 6.1
PackingGroup: III