3-BENZYLOXYANILINE

3-BENZYLOXYANILINE Property

Melting point:

63-67 °C (lit.)

Boiling point:

170 °C(Press: 3 Torr)

Density 

1.129±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Methanol

pka

4.17±0.10(Predicted)

form 

Solid

color 

Pale brown

InChI

InChI=1S/C13H13NO/c14-12-7-4-8-13(9-12)15-10-11-5-2-1-3-6-11/h1-9H,10,14H2

InChIKey

IGPFOKFDBICQMC-UHFFFAOYSA-N

SMILES

C1(N)=CC=CC(OCC2=CC=CC=C2)=C1

CAS DataBase Reference

1484-26-0(CAS DataBase Reference)

EPA Substance Registry System

3-(Benzyloxy)aniline (1484-26-0)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

2811

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29222990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3-BENZYLOXYANILINE Chemical Properties,Usage,Production

Chemical Properties

Beige to tan powder

Synthesis Reference(s)

Tetrahedron Letters, 23, p. 147, 1982 DOI: 10.1016/S0040-4039(00)86770-2

Synthesis

Using 1-(benzyloxy)-3-nitrobenzene as the starting material, the reaction was carried out using an experimental method similar to that of Example 59, in which ferrous acetate (II), nickel nitrate (II), or cobalt acetylacetonate (III) was chosen as the metal reducing agent. The experimental results are detailed in Table 11. The data of Examples 60 to 66 show that the reaction rate is significantly enhanced when metal compounds such as iron, nickel or cobalt salts and amine additives such as pyrrolidine are added to the catalytic reduction system of the present invention in the presence of a rhodium/carrier catalyst. Under this condition, functional groups such as benzyl ether, which are easy to reduce, are retained, and nitro is selectively reduced to amino, thereby increasing the yield of the target products 3-benzyloxyaniline and 3-aminophenol.

References

[1] Patent: EP1541582, 2005, A1. Location in patent: Page/Page column 45
[2] Patent: EP1541582, 2005, A1. Location in patent: Page/Page column 45
[3] Patent: EP1541582, 2005, A1. Location in patent: Page/Page column 45
[4] Patent: EP1541582, 2005, A1. Location in patent: Page/Page column 45
[5] Patent: EP1541582, 2005, A1. Location in patent: Page/Page column 45