3-Chloro-4-methylaniline

3-Chloro-4-methylaniline Property

Melting point:

25 °C

Boiling point:

237-238 °C(lit.)

Density 

1.17

vapor pressure 

4.973-8.666Pa at 25℃

refractive index 

n20/D 1.584(lit.)

Flash point:

212 °F

storage temp. 

2-8°C

solubility 

Chloroform, Methanol (Slightly)

form 

powder to lump to clear liquid

pka

pK1: 4.05(+1) (25°C)

color 

White or Colorless to Light orange to Yellow

Specific Gravity

1.167

Water Solubility 

1 g/L (20 ºC)

BRN 

636511

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents, acid chlorides, acids, acid anhydrides, chloroformates, reducing agents.

LogP

2.27

CAS DataBase Reference

95-74-9(CAS DataBase Reference)

NIST Chemistry Reference

Benzenamine, 3-chloro-4-methyl-(95-74-9)

EPA Substance Registry System

3-Chloro-4-methylaniline (95-74-9)

Safety

Hazard Codes 

T,N,Xn

Risk Statements 

24/25-36/38-43-50/53-36/37/38-22

Safety Statements 

36/37/39-45-61-60-36/37-26

RIDADR 

UN 2239 6.1/PG 3

WGK Germany 

2

RTECS 

XU5111000

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29214300

Hazardous Substances Data

95-74-9(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

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

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

3-Chloro-4-methylaniline Chemical Properties,Usage,Production

Chemical Properties

brown solid

Chemical Properties

The chloromethylanilines are colorless or white crystalline solids or liquids, some have a mild fishy odor.

Uses

2-Chloro-4-aminotoluene has been used in the preparation of 2-chloro-4-cyanotoluene by Sandmeyer reaction with cuprous cyanide.

Definition

ChEBI: A monochloroaniline that is p-toluidine in which one of the hydrogens that is meta to the amino group is replaced by a chlorine.

General Description

Brown solid with a mild odor.

Air & Water Reactions

May be sensitive to prolonged exposure to air and light. Insoluble in water.

Reactivity Profile

3-Chloro-4-methylaniline may be sensitive to prolonged exposure to air and light. 3-Chloro-4-methylaniline may react with oxidizing agents. 3-Chloro-4-methylaniline is incompatible with acids, acid chlorides, acid anhydrides and chloroformates. 3-Chloro-4-methylaniline is also incompatible with reducing agents.

Fire Hazard

3-Chloro-4-methylaniline is combustible.

Safety Profile

Poison by ingestion, intravenous, and intraperitoneal routes. Mutation data reported. When heated to decomposition it emits toxic fumes of Cl and NOx. See also other chloro toluidme entries.

Synthesis

General procedure for the synthesis of 3-chloro-p-toluidine from 2-chloro-4-nitrotoluene: General method: Nitro compounds (1 eq.), hexafluoroisopropanol (HFIP, 10 eq.) and iron powder (5 eq.) were added to the reaction tube and mixed. Subsequently, a 2N aqueous hydrochloric acid solution was slowly added to the reaction mixture. The reaction mixture was stirred at room temperature for 30 minutes and then neutralized with saturated aqueous sodium bicarbonate (NaHCO3) solution. Next, it was extracted three times with saturated aqueous sodium bicarbonate solution. The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. Finally, the crude product was purified by silica gel column chromatography to obtain the target product 3-chloro-p-toluidine.

Potential Exposure

Most of the isomers are used in dyestuff manufacture. The 3-chloro-para isomer is used to kill birds. It is marketed as pelleted bait for control of bird populations.

Shipping

UN2239 Chlorotoluidines, solid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN3429 Chlorotoluidines, liquid, Hazard Class: 6.1; Labels: 6.1- Poisonous materials

Incompatibilities

Incompatible with oxidizers, strong acids; chloroformates, and acid anhydrides, isocyanates, aldehydes forming fire and explosive hazards.

References

[1] Journal of the American Chemical Society, 2017, vol. 139, # 47, p. 17089 - 17097
[2] Tetrahedron Letters, 2017, vol. 58, # 37, p. 3646 - 3649
[3] Chemische Berichte, 1884, vol. 17, p. 534
[4] Recueil des Travaux Chimiques des Pays-Bas, 1932, vol. 51, p. 98,109
[5] Chem. Zentralbl., 1910, vol. 81, # I, p. 260