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2-Phenoxyaniline

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Name

2-Phenoxyaniline

EINECS 220-254-8
CAS No. 2688-84-8 Density 1.141 g/cm3
PSA 35.25000 LogP 3.64230
Solubility N/A Melting Point 47-49 °C(lit.)
Formula C12H11NO Boiling Point 296.4 °C at 760 mmHg
Molecular Weight 185.225 Flash Point 131.8 °C
Transport Information N/A Appearance White to light yellow crystal powder
Safety 26-37/39-36/37/39-36 Risk Codes 20/21/22-36/37/38-22
Molecular Structure Molecular Structure of 2688-84-8 (2-Phenoxyaniline) Hazard Symbols HarmfulXn,IrritantXi
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;

Article Data 51

2-Phenoxyaniline Synthetic route

2216-12-8

1-nitro-2-phenoxy-benzene

2688-84-8

2-phenoxyaniline

Conditions
ConditionsYield
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%
273-53-0

benzoxazole

591-50-4

iodobenzene

2688-84-8

2-phenoxyaniline

Conditions
ConditionsYield
With copper; caesium carbonate at 140℃; for 3h; Inert atmosphere;93%
591-50-4

iodobenzene

95-55-6

2-amino-phenol

2688-84-8

2-phenoxyaniline

Conditions
ConditionsYield
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℃;
108-86-1

bromobenzene

95-55-6

2-amino-phenol

2688-84-8

2-phenoxyaniline

Conditions
ConditionsYield
With sodium dodecyl-sulfate; potassium carbonate In water at 80℃; under 760.051 Torr; for 9h; Ullmann Condensation; Green chemistry; chemoselective reaction;76%
101-84-8

diphenylether

A

139-59-3

4-phenoxyanilin

B

2688-84-8

2-phenoxyaniline

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
88-73-3

2-Chloronitrobenzene

108-95-2

phenol

2688-84-8

2-phenoxyaniline

Conditions
ConditionsYield
(i) DMF, (ii) H2, Raney-Ni; Multistep reaction;
88-73-3

2-Chloronitrobenzene

potassium-salt of salicylaldehyde

potassium-salt of salicylaldehyde

2688-84-8

2-phenoxyaniline

Conditions
ConditionsYield
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
108-95-2

phenol

pentacarbonyl(3-cyclohex-1-enyl-1-ethoxy-2-propyn-1-ylidene)tungsten

pentacarbonyl(3-cyclohex-1-enyl-1-ethoxy-2-propyn-1-ylidene)tungsten

2688-84-8

2-phenoxyaniline

Conditions
ConditionsYield
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

2-Phenoxyaniline Chemical Properties

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

2-Phenoxyaniline Uses

o-PHENOXYANILINE(2688-84-8) is mainly used as dye intermediates.

2-Phenoxyaniline Toxicity Data With Reference

1.   

ivn-mus LD50:212 mg/kg

   TXCYAC    Toxicology. 8 (1977),347.

2-Phenoxyaniline Consensus Reports

Reported in EPA TSCA Inventory.

2-Phenoxyaniline 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

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