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N,N-DIMETHYLANILINE

N,N-Dimethylaniline is an organic chemical compound, a substituted derivative of aniline.
N,N-Dimethylaniline acts as a nucleophilic catalyst, participating in reactions such as acylation, alkylation, and condensation.
N,N-Dimethylaniline is primarily used in the production of dyes, pigments, pharmaceuticals, agrochemicals, and polymerization accelerators.

CAS Number: 121-69-7
EC Number: 204-493-5
Molecular Formula: C8H11N
Molecular Weight: 121.18 g/mol

Synonyms: 6126-96-1, NSC-3462, 2-ethyl-n,n-dimethylaniline, O-ETHYL-N,N-DIMETHYLANILINE, NSC3462, 2YMC6NX8EA, N,N-dimethyl(ethyl)aniline, SCHEMBL709848, SCHEMBL2534567, SCHEMBL3810569, SCHEMBL5685139, SCHEMBL7186300, SCHEMBL9899788, 2-Ethyl-N,N-dimethylbenzenamine, CHEMBL1902738, SCHEMBL27606308, Aniline, o-ethyl-N,N-dimethyl-, DTXSID60976757, Benzenamine, 2-ethyl-N,N-dimethyl-, NCGC00188125-01

N,N-Dimethylaniline is a tertiary aromatic amine formed by substitution of two methyl groups on the nitrogen atom of aniline.
N,N-Dimethylaniline is typically a colorless to pale yellow oily liquid with a characteristic amine-like odor and may gradually darken when exposed to air due to oxidation.

N,N-Dimethylaniline has the molecular formula C8H11N and contains a dimethylamino group directly attached to a benzene ring.
This structure strongly activates the aromatic ring toward electrophilic substitution reactions, making it an important intermediate in organic synthesis.

N,N-Dimethylaniline is primarily used in the production of dyes, pigments, pharmaceuticals, agrochemicals, and polymerization accelerators.
In industrial applications, N,N-Dimethylaniline functions as a catalyst component in peroxide-cured resin systems and as a key precursor in colorant manufacturing.

Because it is an aromatic amine, N,N-Dimethylaniline can be toxic through inhalation, ingestion, or skin absorption, and appropriate industrial hygiene measures are required during handling.

N,N-Dimethylaniline acts as a precursor to triarylmethane dyes such as crystal violet and malachite green.
N,N-Dimethylaniline is also used in the synthesis of vanillin, methyl violet, and Michler's ketone.

Further, N,N-Dimethylaniline is used as a hardener for plastic resins and an acid scavenger in the manufacture of semisynthetic penicillins and cephalosporins.
In addition to this, N,N-Dimethylaniline is used as a promoter in the curing of polyester and vinyl ester resins.

N,N-Dimethylaniline is an organic chemical compound, a substituted derivative of aniline.
N,N-Dimethylaniline is a tertiary amine, featuring a dimethylamino group attached to a phenyl group.

This oily liquid is colourless when pure, but commercial samples are often yellow.
N,N-Dimethylaniline is an important precursor to dyes such as crystal violet.

N,N-Dimethylaniline is a chemical compound that functions as a catalyst in various chemical reactions.
N,N-Dimethylaniline acts as a nucleophilic catalyst, participating in reactions such as acylation, alkylation, and condensation.

The mechanism of action involves the formation of a complex with the substrate, leading to the activation of specific functional groups and facilitating the desired chemical transformation.
N,N-Dimethylaniline is for its ability to promote reactions under mild conditions, making it useful in the synthesis of organic compounds.

N,N-Dimethylaniline plays a role in facilitating the formation of new chemical bonds and promoting the rearrangement of molecular structures.
N,N-Dimethylaniline's mechanism of action involves the interaction with specific reaction intermediates, leading to the acceleration of the desired chemical processes.

Applications of N,N-Dimethylaniline:
N,N-Dimethylaniline is a key precursor to commercially important triarylmethane dyes such as malachite green and crystal violet.
N,N-Dimethylaniline serves as a promoter in the curing of polyester and vinyl ester resins.

N,N-Dimethylaniline is also used as a precursor to other organic compounds.
A study of the in vitro metabolism of N,N-Dimethylaniline using guinea pig and rabbit preparations and GLC techniques has confirmed N-demethylation and N-oxidation as metabolic pathways, and has also established ring hydroxylation as a metabolic route.[11]

N,N-Dimethylaniline is a tertiary amine used in the synthesis of several triarylmethane dyes like malachite green.
N,N-Dimethylaniline is also used in the synthesis of a magnetic gram stain for the detection of bacteria.

Dye and Pigment Manufacturing:
N,N-Dimethylaniline is widely used as an intermediate in the synthesis of azo dyes, triarylmethane dyes, and other colorants for textiles, inks, and plastics.

Polymerization Accelerator:
N,N-Dimethylaniline functions as a curing accelerator in peroxide-initiated polymer systems, especially in polyester resins and acrylic formulations.

Pharmaceutical Intermediates:
N,N-Dimethylaniline serves as a building block in the synthesis of various active pharmaceutical intermediates.

Agrochemical Production:
N,N-Dimethylaniline is used in the preparation of certain pesticides and crop protection chemicals.

Organic Synthesis:
Due to its strong electron-donating dimethylamino group, N,N-Dimethylaniline is employed in electrophilic substitution reactions and as a precursor in advanced organic synthesis.

Rubber and Chemical Processing:
N,N-Dimethylaniline participates in the production of specialty chemicals and rubber additives.

From an industrial chemistry perspective, N,N-Dimethylaniline's high reactivity toward electrophilic aromatic substitution makes it a valuable precursor in large-scale fine chemical manufacturing.

Preparation of N,N-Dimethylaniline:

N,N-Dimethylaniline was first reported in 1850 by the German chemist A. W. Hofmann, who prepared it by heating aniline and iodomethane:
C6H5NH2 + 2 CH3I → C6H5N(CH3)2 + 2 HI

N,N-Dimethylaniline is produced industrially by alkylation of aniline with methanol in the presence of an acid catalyst:
C6H5NH2 + 2 CH3OH → C6H5N(CH3)2 + 2 H2O

Similarly, N,N-Dimethylaniline is also prepared using dimethyl ether as the methylating agent.

Reactions of N,N-Dimethylaniline:
N,N-Dimethylaniline undergoes many of the reactions expected for an aniline, being weakly basic and reactive toward electrophiles.

N,N-Dimethylaniline is nitrated to produce tetryl, a derivative with four nitro groups which was once used as explosive.
In acidic solution, the initial nitration gives 3-nitroN,N-Dimethylaniline.
N,N-Dimethylaniline reacts with butyllithium to give the 2-lithio derivative.

Electrophilic methylating agents like dimethyl sulfate attack the amine to give the quaternary ammonium salt:
C6H5N(CH3)2 +(CH3O)2SO2 → C6H5N(CH3)3CH3OSO3

Diethylaniline and N,N-Dimethylaniline are both used as acid-absorbing bases.

Stability and Reactivity of N,N-Dimethylaniline:

Chemical Stability:
Stable under normal temperatures when stored in tightly closed containers.
May discolor on exposure to air and light due to oxidation.

Reactivity:
Reacts with strong oxidizing agents and strong acids.
Participates readily in electrophilic substitution reactions.

Conditions to Avoid:
Heat.
Ignition sources.
Prolonged air exposure.
Direct sunlight.

Incompatible Materials:
Strong oxidizers.
Strong acids.

Acid chlorides.
Nitrating agents.

Hazardous Decomposition Products:
Combustion may produce carbon oxides (CO, CO₂).
Nitrogen oxides (NOx) may also be released.

Hazardous Polymerization:
Does not occur.

Handling and Storage of N,N-Dimethylaniline:

Handling:
Use in well-ventilated areas.
Avoid inhalation of vapors.

Avoid skin contact.
Prevent formation of mists.
Use grounding during transfer.

Storage:
Store in a cool, dry, well-ventilated area away from heat and oxidizing agents.
Keep container tightly closed.
Protect from light.

First Aid Measures of N,N-Dimethylaniline:

Inhalation:
Move to fresh air immediately.
Seek medical attention if symptoms persist.

Skin Contact:
Remove contaminated clothing.
Wash skin thoroughly with soap and water.

Eye Contact:
Rinse cautiously with water for several minutes.
Seek medical attention.

Ingestion:
Do not induce vomiting.
Obtain medical attention immediately.

Firefighting Measures of N,N-Dimethylaniline:

Suitable Extinguishing Media:
Foam.
Dry chemical.
Carbon dioxide (CO₂).
Water spray.

Specific Hazards:
Flammable liquid.
Vapors may form explosive mixtures with air.
Combustion releases toxic fumes.

Protective Equipment:
Firefighters should wear self-contained breathing apparatus.

Accidental Release Measures of N,N-Dimethylaniline:

Personal Precautions:
Evacuate area.
Use appropriate protective equipment.
Eliminate ignition sources.

Environmental Precautions:
Prevent entry into drains and waterways.

Cleanup:
Absorb with inert material such as sand or vermiculite.
Place in suitable containers for disposal.

Exposure Controls / Personal Protection of N,N-Dimethylaniline:

Engineering Controls:
Use local exhaust ventilation.
Use closed systems where possible.

Personal Protective Equipment:
Wear chemical-resistant gloves.
Wear protective clothing.

Wear safety goggles or face shield.
Use respiratory protection if ventilation is inadequate.

Identifiers of N,N-Dimethylaniline:
CAS: 121-69-7
IUPAC Name: N,N-Dimethylaniline
Molecular Formula: C8H11N
InChI Key: JLTDJTHDQAWBAV-UHFFFAOYSA-N
SMILES: CN(C)C1=CC=CC=C1
Molecular Weight (g/mol): 121.18

Product Number: D0665
Purity / Analysis Method : >99.0%(GC)(T)
Molecular Formula / Molecular Weight: C8H11N = 121.18
Physical State (20 deg.C): Liquid
Storage Temperature : Room Temperature (Recommended in a cool and dark place, <15°C)
Store Under Inert Gas: Store under inert gas
Condition to Avoid: Air Sensitive
CAS RN: 121-69-7
Reaxys Registry Number: 507140
PubChem Substance ID: 87567306
SDBS (AIST Spectral DB): 1852
Merck Index (14): 3234
MDL Number: MFCD00008304

Linear Formula: C6H5N(CH3)2
CAS Number: 121-69-7
Molecular Weight: 121.18
UNSPSC Code: 12352100
NACRES: NA.22
PubChem Substance ID: 57651326
EC Number: 204-493-5
Beilstein/REAXYS Number: 507140
MDL number: MFCD00008304
Assay: 99%
Bp: 193-194 °C (lit.)

CAS number: 121-69-7
EC index number: 612-016-00-0
EC number: 204-493-5
Hill Formula: C₈H₁₁N
Chemical formula: C₆H₅N(CH₃)₂
Molar Mass: 121.18 g/mol
HS Code: 2921 42 00

CAS Number: 121-69-7
ChEBI: CHEBI:16269
ChEMBL: ChEMBL371654
ChemSpider: 924
ECHA InfoCard: 100.004.085
KEGG: C02846
PubChem CID: 949
UNII: 7426719369
CompTox Dashboard (EPA): DTXSID2020507
InChI: InChI=1S/C8H11N/c1-9(2)8-6-4-3-5-7-8/h3-7H,1-2H3
Key: JLTDJTHDQAWBAV-UHFFFAOYSA-N
SMILES: CN(C)c1ccccc1

Properties of N,N-Dimethylaniline:
Chemical formula: C8H11N
Molar mass: 121.183 g·mol−1
Appearance: Colorless liquid
Odor: amine-like
Density: 0.956 g/mL
Melting point: 2 °C (36 °F; 275 K)
Boiling point: 194 °C (381 °F; 467 K)
Solubility in water: 2% (20°C)
Vapor pressure: 1 mmHg (20°C)
Magnetic susceptibility (χ): −89.66·10−6 cm3/mol

Melting Point: 2 °C
Boiling Point: 194 °C
Flash point: 73 °C
Specific Gravity (20/20): 0.96
Refractive Index: 1.56
Solubility in water: Insoluble
Solubility (miscible with): Chloroform, Acetone, Ether, Alcohol

InChI key: JLTDJTHDQAWBAV-UHFFFAOYSA-N
InChI: 1S/C8H11N/c1-9(2)8-6-4-3-5-7-8/h3-7H,1-2H3
SMILES string: CN(C)c1ccccc1
product line: ReagentPlus®
assay: 99%
Quality Level: 200
dilution: (for general lab use)
refractive index: n20/D 1.557 (lit.)
pH: 7.4 (20 °C, 1.2 g/L)
bp: 193-194 °C (lit.)
mp: 1.5-2.5 °C (lit.)
density: 0.956 g/mL at 25 °C (lit.)
application(s): microbiology
functional group: amine

Boiling point: 192 - 195 °C (1013 hPa)
Density: 0.96 g/cm3 (20 °C)
Explosion limit: 1.2 - 7 %(V)
Flash point: 75 °C
Ignition temperature: 370 °C DIN 51794
Melting Point: 2.5 °C
pH value: 7.4 (1.2 g/l, H₂O, 20 °C)
Vapor pressure: 0.53 hPa (20 °C)
Solubility: 1.2 g/l

Specifications of N,N-Dimethylaniline:
Assay (GC, area%): ≥ 99.0 % (a/a)
Density (d 20 °C/ 4 °C): 0.955 - 0.957
Identity (IR): passes test

Appearance: Colorless to Light orange to Yellow clear liquid
Purity(GC): min. 99.0 %
Purity(Nonaqueous Titration): min. 99.0 %
NMR: confirm to structure

Appearance (Color): Clear pale yellow to yellow
Assay (GC): ≥98.5%
Form: Liquid
Refractive Index: 1.5555-1.5595 @ 20?C

Names of N,N-Dimethylaniline:

Preferred IUPAC name:
N,N-Dimethylaniline

Other names:
DMA
Dimethylaminobenzene
N,N-Dimethylbenzeneamine
N,N-Dimethylphenylamine