2-Phenoxyaniline

Product Name2-Phenoxyaniline
CAS2688-84-8
MFC12H11NO
MW185.22
EINECS220-254-8
MOL File2688-84-8.mol

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
InChI	1S/C12H11NO/c13-11-8-4-5-9-12(11)14-10-6-2-1-3-7-10/h1-9H,13H2
InChIKey	NMFFUUFPJJOWHK-UHFFFAOYSA-N
SMILES	Nc1ccccc1Oc2ccccc2
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	TSCA listed
HazardClass	6.1
PackingGroup	III
HS Code	29222990
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Dermal Acute Tox. 4 Inhalation Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3
Toxicity	LD50 ivn-mus: 212 mg/kg TXCYAC 8,347,77

MSDS

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

Usage And Synthesis

Chemical Properties

Whitetolightyellowcrystalpowde

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.

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.

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

591-50-4

95-55-6

2688-84-8

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

Chemical Properties

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MSDS

Usage And Synthesis

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