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3-Chloro-p-toluidine is used in the preparation of 2-chloro-4-cyanotoluene by Sandmeyer reaction with cuprous cyanide.
3-Chloro-p-toluidine is primarily used as a valuable intermediate in the chemical industry rather than as a final commercial product.
3-Chloro-p-toluidine also serves as an intermediate in the synthesis of pesticides and agricultural chemicals.
CAS Number: 95-74-9
EC Number: 202-446-3
Molecular Formula: C₇H₈ClN
Molecular Weight: 141.60 g/mol
SYNONYMS:
3-Chloro-p-toluidine, 3-Chloro-4-methylaniline, 4-Amino-2-chlorotoluene, 2-Chloro-4-aminotoluene, 1-Amino-3-chloro-4-methylbenzene, 4-Methyl-3-chloroaniline, 3-Chloro-4-methyl-phenylamine, CPT, OCPT, 3-Chloro-p-methylaniline, 2-Chloro-4-aminotoluene, 4-Amino-2-chlorotoluene, 3-Chloro-4-methylaniline, 3-Chloro-4-methylaniline, 3-Chloro-p-toluidine, 4-Amino-2-chlorotoluene, Benzenamine,3-chloro-4-methyl-, p-Toluidine,3-chloro-, 3-Chloro-4-methylbenzenamine, 3-Chloro-p-toluidine, 3-Chloro-4-methylaniline, 4-Methyl-3-chloroaniline, 1-Amino-3-chloro-4-methylbenzene, 2-Chloro-4-aminotoluene, DRC 1347, 3-Chloro-4-methylphenylamine, NSC 96620, 4-Amino-2-chlorotoluene
3-Chloro-p-toluidine (C7H8ClN) is an organic halogenated aromatic amine.
3-Chloro-p-toluidine appears as a white to pale yellow solid at room temperature, often in the form of crystals or crystalline powder, and may exhibit a faint characteristic amine-like odor.
3-Chloro-p-toluidine contains a chlorinated benzene ring with a methyl and an amino functional group attached, which contributes to its reactivity and utility in synthetic chemistry.
3-Chloro-p-toluidine was first synthesized in the early 20th century during the expansion of aromatic amine research for dye and pharmaceutical development, though no single scientist or definitive date has been widely credited for its initial discovery.
3-Chloro-p-toluidine is typically prepared via nitration and subsequent reduction of chlorotoluene derivatives followed by selective halogenation steps under controlled conditions.
3-Chloro-p-toluidine serves as an important intermediate in the production of various agrochemicals, particularly herbicides and fungicides, and also finds application in the synthesis of pharmaceutical agents and dyes.
While not known to occur naturally in biological systems, 3-Chloro-p-toluidine can be industrially produced from commercially available chlorinated aromatic precursors.
Industrial preparation commonly involves multi-step organic synthesis routes starting from 3-chlorotoluene, using nitration, reduction, and sometimes acetylation-deacetylation techniques under acidic or basic conditions to yield the desired aniline derivative.
For safe storage, 3-Chloro-p-toluidine should be kept in a cool, dry, well-ventilated area, away from strong oxidizing or reducing agents.
3-Chloro-p-toluidine is a colorless or white crystalline solids or liquids, some have a mild fishy odor.
3-chloro-p-toluidine is a brown solid with a mild odor.
3-Chloro-p-toluidine is a monochloroaniline that is p-toluidine in which one of the hydrogens that is meta to the amino group is replaced by a chlorine.
3-Chloro-p-toluidine has a role as an avicide.
3-Chloro-p-toluidine is a chloroaniline and a member of monochlorobenzenes.
3-Chloro-p-toluidine derives from a p-toluidine.
3-Chloro-p-toluidine is an aromatic amine belonging to the chloroaniline family.
3-Chloro-p-toluidine consists of a benzene ring substituted with one amino group (-NH₂), one chlorine atom, and one methyl group.
Due to the presence of both amino and halogen substituents, 3-Chloro-p-toluidine is an important building block in numerous industrial organic synthesis processes.
USES and APPLICATIONS of 3-CHLORO-p-TOLUIDINE:
3-Chloro-p-toluidine is used in the preparation of 2-chloro-4-cyanotoluene by Sandmeyer reaction with cuprous cyanide.
3-Chloro-p-toluidine is primarily used as a valuable intermediate in the chemical industry rather than as a final commercial product.
One of 3-Chloro-p-toluidine's largest applications is in the manufacture of azo dyes and organic pigments, where the amino group can undergo diazotization followed by coupling reactions to generate highly colored compounds with excellent color strength and stability.
3-Chloro-p-toluidine also serves as an intermediate in the synthesis of pesticides and agricultural chemicals.
Various herbicides, avicides, and specialty crop-protection products have historically been prepared using derivatives of 3-Chloro-p-toluidine as key starting materials.
In pharmaceutical research, 3-Chloro-p-toluidine is employed as a building block for synthesizing heterocyclic compounds and biologically active molecules.
The aromatic amine functionality provides opportunities for preparing numerous substituted benzene derivatives used during medicinal chemistry development.
Within specialty chemical manufacturing, 3-Chloro-p-toluidine is used to produce antioxidants, rubber chemicals, corrosion inhibitors, and performance additives.
3-Chloro-p-toluidine also participates in the preparation of advanced intermediates for electronic chemicals, laboratory reagents, and custom organic synthesis.
3-Chloro-p-toluidine is commonly encountered as a synthetic intermediate in the manufacture of dyes, pigments, agricultural chemicals, and specialty organic compounds.
Researchers frequently use 3-Chloro-p-toluidine in synthetic organic chemistry because the amino group can easily be transformed into many different functional groups through well-established reaction pathways.
This versatility makes 3-Chloro-p-toluidine an attractive precursor for preparing more complex aromatic molecules with controlled substitution patterns.
3-Chloro-p-toluidine is used as a dye intermediate.
PROPERTIES and CHARACTERISTICS of 3-CHLORO-p-TOLUIDINE:
3-Chloro-p-toluidine is an aromatic primary amine possessing both nucleophilic and electrophilic reactive sites, making it an important intermediate in aromatic substitution reactions.
The amino group readily participates in diazotization, acylation, alkylation, condensation, and coupling reactions, while the chlorine substituent influences 3-Chloro-p-toluidine's electronic properties and regioselectivity during synthesis.
The presence of both methyl and chlorine substituents modifies its chemical reactivity compared with unsubstituted aniline, improving 3-Chloro-p-toluidine's usefulness as a precursor for more complex aromatic compounds.
3-Chloro-p-toluidine demonstrates relatively good thermal stability under normal processing conditions and can tolerate many industrial synthetic operations without significant decomposition.
Because of its aromatic structure, 3-Chloro-p-toluidine exhibits moderate hydrophobicity and dissolves much better in organic solvents than in water.
3-Chloro-p-toluidine is frequently selected when controlled halogen substitution is required during multi-step organic synthesis.
Commercial samples may gradually darken during storage because aromatic amines are susceptible to slow oxidation in the presence of oxygen and light.
For this reason, storage under tightly sealed containers protected from moisture and sunlight is generally recommended.
BENEFITS of 3-CHLORO-p-TOLUIDINE:
Important intermediate for numerous industrial syntheses.
High versatility in aromatic substitution chemistry.
Excellent precursor for azo dye and pigment production.
Useful starting material for pharmaceutical research.
Suitable for preparation of agricultural chemical intermediates.
Good thermal stability during industrial processing.
Reactive amino group allows numerous chemical transformations.
Chlorine substituent enhances synthetic selectivity.
Compatible with many common organic reaction conditions.
Valuable building block in specialty chemical manufacturing.
PHYSICAL and CHEMICAL PROPERTIES of 3-CHLORO-p-TOLUIDINE:
Appearance: Brown crystalline solid or brown solid
Odor: Mild aromatic amine odor
Molecular Formula: C₇H₈ClN
Molecular Weight: 141.60 g/mol
CAS Number: 95-74-9
EC Number: 202-446-3
Melting Point: Approximately 25°C
Boiling Point: 237–238°C
Density: Approximately 1.17 g/cm³ (25°C)
Refractive Index: n20/D approximately 1.584
Flash Point: Approximately 100°C (212°F)
Vapor Pressure: Low (approximately 5–9 Pa at 25°C)
Water Solubility: Slightly soluble (about 1 g/L at 20°C)
Solubility: Soluble in many organic solvents including ethanol, methanol, chloroform, ether, acetone and benzene
Physical State: Solid at room temperature, may liquefy near its melting point
Color: White to pale yellow when pure; commercial material may appear brown due to oxidation
pKa: Approximately 4.0
Log Kow: Moderate, indicating moderate lipophilicity
Stability: Stable under recommended storage conditions
Light Sensitivity: May slowly darken upon prolonged exposure to light
Air Sensitivity: May oxidize slowly when exposed to air
Volatility: Low
Combustibility: Combustible organic compound
Surface Tension: Low (typical aromatic amine behavior)
Viscosity: Not generally reported because it is normally handled as a solid or molten material
Chemical Family: Aromatic amine; monochloroaniline derivative
Chemical Name: 3-Chloro-p-toluidine
IUPAC Name: 3-Chloro-4-methylaniline
CAS Number: 95-74-9
EC Number: 202-446-3
Molecular Formula: C₇H₈ClN
Molecular Weight: 141.60 g/mol
CAS Number: 95-74-9
Formula: C₇H₈ClN
MDL Number: MFCD00007773
Molecular Weight: 141.6 g/mol
Boiling Pt: 244°C
Melting Pt: 26 °C
Density: 1,108 g/cm³ (20 °C)
Storage Temperature: Refrigerator
EINECS: 202-446-3
Linear Formula: ClC6H3(CH3)NH2
CAS Number: 95-74-9
Molecular Weight: 141.60
UNSPSC Code: 12352100
NACRES: NA.22
PubChem Substance ID: 24854163
EC Number: 202-446-3
Beilstein/REAXYS Number: 636511
MDL number: MFCD00007773
Assay: 98%
Form: solid
Physical state: solid
Color: No data available
Odor: No data available
Melting point/ range: 24 - 25 °C
Method: lit.
Boiling point/boiling range: 237 - 238 °C
Method: lit.
Flammability: No data available
Upper explosion limit / Upper flammability limit: No data available
Lower explosion limit / Lower flammability limit: No data available
Flash point: 100 °C
Method: closed cup
Autoignition temperature: No data available
Decomposition temperature: No data available
pH: No data available
Viscosity, dynamic: No data available
Viscosity, kinematic: No data available
Flow time: No data available
Water solubility: No data available
Partition coefficient: noctanol/water: No data available
Vapor pressure: No data available
Relative density: No data available
Density: 1,167 g/mL (25 °C)
Relative vapour density: No data available
Explosives: No data available
Oxidizing properties: No data available
Burning rate: No data available
Evaporation rate: No data available
Molecular weight: 141,60 g/mol
Molecular Formula / Molecular Weight: C7H8ClN = 141.60
Physical State (20 deg.C): Solid
Storage Temperature: Refrigerated (0-10°C)
Store Under Inert Gas: Store under inert gas
Condition to Avoid: Light Sensitive,Air Sensitive
CAS RN: 95-74-9
Reaxys Registry Number: 636511
PubChem Substance ID: 87565650
SDBS (AIST Spectral DB): 3867
MDL Number: MFCD00007773
Molecular Weight: 141.6
Exact Mass: 141.60
UN: 2239
ADR: 6.1,III
BRN: 636511
EC Number: 202-446-3
UNII: 32Y306W7BQ
NSC Number: 96620
UN Number: 2239
DSSTox ID: DTXSID0020286
HScode: 29214300
PSA: 26
XLogP3: 2.9
Appearance: 3-chloro-p-toluidine is a brown solid with a mild odor.
Density: 1.108 (NTP, 1992)
Melting Point: 26 °C
Boiling Point: 242-244 °C @ Press: 760 Torr
Flash Point: 212 °F
Refractive Index: 1.585
Water Solubility: H2O: 1 g/L (20 ºC)soluble in ethanol; slightly soluble in carbon tetrachloride
Storage Conditions: 2-8°C
Vapor Pressure: 4.08X10-2 mm Hg at 25 deg C (est)
Henrys Law Constant: Henry's Law constant = 1.99X10-6 atm-cu m/mol at 25 °C (est)
Dissociation Constants: pKa = 4.05 (conjugate acid)
Air and Water Reactions: May be sensitive to prolonged exposure to air and light. Insoluble in water.
Reactive Group: Aryl Halides
Autoignition Temperature: > /= 500 °C
FIRST AID MEASURES of 3-CHLORO-p-TOLUIDINE:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation:
Fresh air.
*In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.
*If swallowed:
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available
ACCIDENTAL RELEASE MEASURES of 3-CHLORO-p-TOLUIDINE:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up dry.
Dispose of properly.
Clean up affected area.
FIRE FIGHTING MEASURES of 3-CHLORO-p-TOLUIDINE:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2)
Foam
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.
EXPOSURE CONTROLS/PERSONAL PROTECTION of 3-CHLORO-p-TOLUIDINE:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection.
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A
-Control of environmental exposure:
Do not let product enter drains.
HANDLING and STORAGE of 3-CHLORO-p-TOLUIDINE:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.
STABILITY and REACTIVITY of 3-CHLORO-p-TOLUIDINE:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available
