2-Phenoxyaniline Chemical Properties

Melting point:

47-49 °C(lit.)

Boiling point:

170 °C18 mm Hg(lit.)

Density 

1.0936 (rough estimate)

refractive index 

1.5300 (estimate)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Slightly soluble in chloroform and methanol.

pka

3.78±0.10(Predicted)

form 

Crystalline Powder or Flakes

color 

Brown to gray

BRN 

777766

Stability:

Hygroscopic

CAS DataBase Reference

2688-84-8(CAS DataBase Reference)

NIST Chemistry Reference

2-Aminodiphenyl ether(2688-84-8)

EPA Substance Registry System

o-Phenoxyaniline (2688-84-8)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38-22

Safety Statements 

26-37/39-36/37/39-36

RIDADR 

2811

WGK Germany 

3

RTECS 

BY7940000

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29222990

Toxicity

LD50 ivn-mus: 212 mg/kg TXCYAC 8,347,77

MSDS

• Language:English Provider:2-Aminophenyl phenyl ether
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Phenoxyaniline Usage And Synthesis

Chemical Properties

Whitetolightyellowcrystalpowde

Uses

2-Phenoxyaniline serves as an antiinflammatory agent that inhibits preferentially COX-2 over COX-1. It is used in the preparation of sodium primary amide complex, 4-methyl-2-(2-phenoxyphenyl)azo-phenol and 2-acetoaminodiphenyl ether. Further, it is used to form complexes with beta-cyclodextrin.

Uses

2-Phenoxyaniline may be used in the preparation of sodium primary amide complex, 2-PhOC₆H₄NHNa·NMe[(CH₂)₂NMe₂]₂. It was used in the preparation of 2-acetoaminodiphenyl ether. It may be used in the preparation of 4-methyl-2-(2-phenoxyphenyl)azo-phenol.

General Description

2-Phenoxyaniline forms crystalline 2:1 (host-to-guest) inclusion complexes with β-cyclodextrin.

Safety Profile

Poison by intravenous route. When heated to decomposition it emits toxic vapors of NOx.

Synthesis

General procedure: all reactions were carried out under air atmosphere. Iodobenzene (1.0 mmol), o-aminophenol (1.0 mmol), CuI (0.1 mmol), 1-(α-aminobenzyl)-2-naphthol (0.2 mmol), and K2CO3 (2.0 equiv.) were dissolved in 3 mL of DMSO, and the reaction was carried out for 24 hr at 120 °C. The reaction process was monitored by gas chromatography (GC). Upon completion of the reaction, the catalyst was removed by filtration and the product was extracted with ethyl acetate (EtOAc). The organic layers were combined and dried with anhydrous MgSO4 for 12 hours. The solvent was removed by concentration under reduced pressure and the resulting crude product was purified by silica gel column chromatography with the eluent of petroleum ether/ethyl acetate (10:1, v/v) to afford the target compound 2-aminodiphenyl ether.

References

[1] Synthetic Communications, 2014, vol. 44, # 17, p. 2468 - 2477
[2] Tetrahedron Letters, 2014, vol. 55, # 51, p. 7082 - 7088

2-Phenoxyaniline(2688-84-8)Related Product Information

• Phenylhydrazine
• PHENYL VALERATE
• Dimethyl ether
• C8E3
• 4,4'-Oxydiphthalic anhydride
• Triclosan
• 4,4'-Oxydianiline
• Ethylbenzene
• Diphenyl ether
• 4-Nitro-2-phenoxyaniline
• NiMesulide EP IMpurity E
• N-(Methylsulfonyl)-4'-nitro-2'-phenoxyMethanesulfonanilide
• (2-PHENOXY)METHYLSULFONYLANILINE
• 2-(p-tolyloxy)aniline
• 2-AMINO-4,4'-DICHLORODIPHENYL ETHER
• 5-Chloro-2-(2-chlorophenoxy)aniline
• Diethyl ether
• Phenoxazine