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3-Chloro-4-methylaniline

Product Name3-Chloro-4-methylaniline
CAS95-74-9
MFC7H8ClN
MW141.6
EINECS202-446-3
MOL File95-74-9.mol

Chemical Properties

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
Henry's Law Constant	4.9×10⁰ mol/(m³Pa) at 25℃, HSDB (2015)
Stability	Stable. Combustible. Incompatible with strong oxidizing agents, acid chlorides, acids, acid anhydrides, chloroformates, reducing agents.
InChI	1S/C7H8ClN/c1-5-2-3-6(9)4-7(5)8/h2-4H,9H2,1H3
InChIKey	RQKFYFNZSHWXAW-UHFFFAOYSA-N
SMILES	Cc1ccc(N)cc1Cl
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 Information

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	TSCA listed
HazardClass	6.1
PackingGroup	III
HS Code	29214300
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 3 Dermal Acute Tox. 3 Oral Aquatic Acute 1 Aquatic Chronic 1 Eye Irrit. 2 Skin Irrit. 2 Skin Sens. 1
Hazardous Substances Data	95-74-9(Hazardous Substances Data)

MSDS

Provider	Language
3-Amino-2-chlorotoluene	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Chemical Properties

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

Chemical Properties

brown solid

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

121-86-8

95-74-9

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

3-Chloro-4-methylaniline

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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