4-BUTOXYANILINE

4-BUTOXYANILINE Property

Melting point:

130-132 °C

Boiling point:

148-149 °C13 mm Hg(lit.)

Density 

0.992 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.538(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

clear liquid

pka

5.23±0.10(Predicted)

color 

Colorless to Brown

Specific Gravity

approximate 1

BRN 

2084421

CAS DataBase Reference

4344-55-2(CAS DataBase Reference)

NIST Chemistry Reference

Benzenamine, 4-butoxy-(4344-55-2)

EPA Substance Registry System

Benzenamine, 4-butoxy- (4344-55-2)

Safety

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-28-36/37/39-45

RIDADR 

2810

WGK Germany 

3

RTECS 

BW9420000

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29214200

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.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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

4-BUTOXYANILINE Chemical Properties,Usage,Production

Chemical Properties

CLEAR DARK BROWN LIQUID

Uses

4-Butoxyaniline was used in the preparation of:

• bis-4-butoxyphenyl-4,4′-(2,2′-bipyridyl)carbamide
• 1-(4-butoxyphenyl)-3-(6-methyl-3-oxo-2-phenyl-2,3-dihydropyridazin-4-yl)urea

General Description

4-Butoxyaniline undergoes low-pressure hydrogenation in the presence of rhodium on alumina to yield 4-butoxycyclohexylamine.

Synthesis

GENERAL METHOD: 1-butoxy-4-nitrobenzene (0.0270 mol) was dissolved in 70 mL of ethanol. Tin chloride (0.119 mol) was dissolved in 30 mL of ethanol and added dropwise to the reaction system. The reaction was stirred continuously at 80 °C for 2 hours. Upon completion of the reaction, the crude product was extracted twice with a solvent mixture of ethyl acetate/water (1:1, v/v) and 60 g of potassium carbonate was added to the aqueous phase to neutralize the acidic by-products. The organic phases were combined and the solvent was removed by evaporation under reduced pressure to give the yellow oily product 4-butoxyaniline. Yields ranged from 65% to 85%. For 4-butoxyaniline (3a), the 1H-NMR (DMSO-d6) data were as follows: δ 6.64 (d, 2H), 6.52 (d, 2H), 4.56 (s, 2H), 3.58 (t, 2H), 1.75 (m, 2H), 1.39 (m, 2H), 0.99 (t, 3H). The yield of 4-butoxyaniline under this experimental condition was 65%.

References

[1] Science China Chemistry, 2011, vol. 54, # 11, p. 1726 - 1734
[2] Molecules, 2017, vol. 22, # 8,
[3] Molecular Crystals and Liquid Crystals, 2009, vol. 510, p. 250 - 258
[4] Synthetic Communications, 1981, vol. 11, # 11, p. 925 - 930
[5] Journal of the American Chemical Society, 1922, vol. 44, p. 1744