DIMETHYLANILINE

DIMETHYLANILINE = DIMETHYLAMINOBENZENE = N,N-DIMETHYLBENZENEAMINE

CAS Number: 121-69-7 
EC-Number: 204-493-5
MDL number: MFCD00008304
Chemical formula: C8H11N

Dimethylaniline (DMA) is an organic chemical compound, a substituted derivative of aniline. 
Dimethylaniline consists of a tertiary amine, featuring dimethylamino group attached to a phenyl group. 
Dimethylaniline is colourless when pure, but commercial samples are often yellow. 
Dimethylaniline is an important precursor to dyes such as crystal violet.
Dimethylaniline is also written as DMA. 

Dimethylaniline, also known as dimethylaminobenzene or dimethylphenylamine, belongs to the class of organic compounds known as dialkylarylamines. 
Dimethylaniline is a tertiary amine that is aniline in which the amino hydrogens are replaced by two methyl groups. 
Dimethylaniline is a tertiary amine and a dimethylaniline. 
Dimethylaniline appears as a yellow to brown colored oily liquid with a fishlike odor. 

Dimethylaniline is less dense than water and insoluble in water. 
Dimethylaniline's flash point is 150 °F. 
Outside of the human body, Dimethylaniline has been detected, but not quantified in several different foods, such as common mushrooms, strawberries, feijoa, limes, and black-eyed pea.
Dimethylaniline belongs to the class of organic compounds known as dialkylarylamines. 
Dimethylaniline is a nearly quantitative yield of benzoic acid, N-methyl aniline and formaldehyde .

No information is available on the reproductive, developmental effects of N,N-dimethylaniline in humans.  
The chemical formula for dimethylaniline is C8H11N, and Dimethylaniline's molecular weight is 121.18 g/mol. 
Dimethylaniline occurs as a yellow oily liquid that is insoluble in water. 
The odor threshold for dimethylaniline is 0.013 parts per million (ppm). 
The vapor pressure for dimethylaniline is 0.52 mm Hg at 25 °C, and its log octanol/water partition coefficient (log K ow) is 2.31.

Dimethylaniline is a tertiary amine that is aniline in which the amino hydrogens are replaced by two methyl groups. 
Dimethylaniline is a tertiary amine and a dimethylaniline.
Dimethylaniline appears as a yellow to brown colored oily liquid with a fishlike odor. 
Less dense than water and insoluble in water. 
Dimethylaniline is a tertiary amine that is aniline in which the amino hydrogens are replaced by two methyl groups.

Dimethylaniline  (DMA, CAS No. 121-69-7) belongs to the N-dialkylaminoaromatics, a chemical class structurally alerting to DNA reactivity. 
Dimethylaniline (DMA) is an organic chemical compound, a substituted derivative of aniline. 
Dimethylaniline consists of a tertiary amine, featuring dimethylamino group attached to a phenyl group. 
Dimethylaniline is colourless when pure, but commercial samples are often yellow. 

Dimethylaniline molecule contains a total of 20 bonds.
Dimethylaniline is a yellow oily liquid, insoluble in water, soluble in ethanol, ether. 
Dimethylaniline (DMA) CAS NO. 121-69-7 also known as N,N-dimethylaniline, dimethylaminobenzene and. 
Dimethylaniline is a yellow oily liquid, insoluble in water, soluble in ethanol, ether. 

USES and APPLICATIONS of DIMETHYLANILINE:
-Dimethylaniline is a key precursor to commercially important triarylmethane dyes such as malachite green and crystal violet.
-Dimethylaniline serves as a promoter in the curing of polyester and vinyl ester resins.
-Dimethylaniline is also used as a precursor to other organic compounds. 
-A study of the in vitro metabolism of Dimethylaniline has confirmed N-demethylation and N-oxidation as metabolic pathways, and has also established ring hydroxylation as a metabolic route.

-Dimethylaniline's derivative 2,4-dimethylaniline is a recalcitrant degradant of the pesticide amitraz.
-Dimethylaniline was used to make dyes and as a solvent. 
-Dimethylaniline is used as an intermediate in the manufacture of dyes and other substances.  
-Dimethylaniline is used as an intermediate in the manufacture of vanillin, Michler's ketone, methyl violet, and other dyes and also as a solvent, an alkylating agent, and a stabilizer. 

-Dimethylaniline is a promoter used in the curing of polyester and vinyl ester resins. 
-Dimethylaniline can be used on its own with benzoyl peroxide (BPO) type catalysts or in combination with cobalt 6% promoters with methyl ethyl ketone (MEKP) type catalysts.  
-The purpose of Dimethylaniline  is to speed up the curing reaction of polyester and vinyl ester resins and allow them to cure at room temperature. 

-The Dimethylaniline helps the catalyst to start the chemical reaction between the resin and styrene monomer and form a cured solid.
-Dimethylaniline's applications may be industrial (dye and pesticide intermediates, polymerizing agents) and surgical (polymerization accelerations for the manufacture of bone cements and prosthetic devices), thus implying heterogeneous types of human exposure.

-Dimethylaniline is widely used in manufacturing as a solvent, an intermediate and reagent for
-Dimethylaniline is used in dyes, a rubber vulcanising agent and as a catalyst. 
-Dimethylaniline is used in Manufacture of Michler's ketone, as reagent for methanol, methyl furfural, hydrogen peroxide, nitrate, alcohol, formaldehyde.
-Dimethylaniline is used in the synthesis of vanillin, methyl violet, and Michler's ketone; also used as a hardener for plastic resins and a acid scavenger in the manufacture of semisynthetic penicillins and cephalosporins.

-Dimethylaniline was originally developed for use in conjunction with the manufacture of basic dyes, vanillin and Michler's ketone. 
-Dimethylaniline has a number of other varied uses, such as with MBTH in a colorimetric peroxidase determination. 
-Dimethylaniline is used as a reagent in a sensitive procedure using p-anisidene-N, N-dimethylaniline for the catalytic determination of micro-amounts of ferric and ferrous ions in as little as 10-7 mole.
-Dimethylaniline is used in various embedding resin systems such as SPI Chem Low Acid HPMA for Light Microscopy.

-Dimethylaniline is a yellowish to brownish oily liquid compound C6H5N(CH3)2 made by methylating aniline and used chiefly as an intermediate in dye manufacture.
-Dimethylaniline is used to make dyes and as a solvent.
-Dimethylaniline is mainly used as dye intermediates, solvents, stabilizers, analytical reagents. 
-Dimethylaniline is used as curing agent for epoxy resin, as intermediate for organic synthesis, used in the preparation of quatemary amine, dehydrogenation catalyst, preservative and neutralizing agent.

-Dimethylaniline is a tertiary amine used in the synthesis of several triarylmethane dyes, such as peacock green. 
-Dimethylaniline is also used in the synthesis of magnetic Gram stains for the detection of bacteria.
-Dimethylaniline is mainly used as dye intermediates, solvents, stabilizers, analytical reagents.
-Dimethylaniline is an important precursor to dyes such as crystal violet.

PREPARATION and REACTIONS of DIMETHYLANILINE:
Dimethylaniline was first reported in 1850 by the German chemist A. W. Hofmann, who prepared Dimethylaniline by heating aniline and iodomethane:
C6H5NH2 + 2 CH3I → C6H5N(CH3)2 + 2 HI
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, Dimethylaniline is also prepared using dimethyl ether as the methylating agent.
Dimethylaniline undergoes many of the reactions expected for an aniline, being weakly basic and reactive toward electrophiles. 
For example, Dimethylaniline is nitrated to produce tetryl, a derivative with four nitro groups which was once used as explosive. 

Dimethylaniline is lithiated with butyllithium. 
Methylating agents attack the amine to give the quaternary ammonium salt:
C6H5N(CH3)2 + (CH3O)2SO2 → C6H5N(CH3)3CH3OSO3

SUBSTITUENTS of DIMETHYLANILINE:
Aniline or substituted anilines
Dialkylarylamine
Benzenoid
Monocyclic benzene moiety
Organopnictogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

ALTERNATIVE PARENTS of DIMETHYLANILINE:
Aniline and substituted anilines 
Organopnictogen compounds 
Hydrocarbon derivatives 

PHYSICAL and CHEMICAL PROPERTIES of DIMETHYLANILINE:
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)[1]
Vapor pressure: 1 mmHg (20°C)[1]
Magnetic susceptibility (χ): -89.66·10−6 cm3/mol
Appearance Form: liquid

Color: light yellow
pH: 7,4 at 1,2 g/l at 20 °C
Melting point/freezing point Melting point/range: 1,5 - 2,5 °C - lit.
Initial boiling point and boiling range: 193 - 194 °C - lit.
Flash point: 75 °C - closed cup
Evaporation rate No data available
Flammability (solid, gas): No data available

Vapor pressure: 13 hPa at 70 °C 
Vapor density: 4,18 - (Air = 1.0)
Relative density: 0,956 g/cm³ at 25 °C
Water solubility: ca.1 g/l
Partition coefficient: n-octanol/water log Pow: 2,62
Autoignition temperature: No data available
Decomposition temperature: No data available
Viscosity Viscosity, kinematic: No data available
Viscosity, dynamic: 1,2 mPa.s at 30 °C

Water Solubility: 14.4 g/L    
logP: 2.05    
logP: 2.08    
logS: -0.92    
pKa (Strongest Basic): 5.02    
Physiological Charge: 0    
Hydrogen Acceptor Count: 1    
Hydrogen Donor Count: 0    
Polar Surface Area: 3.24 Ų    
Rotatable Bond Count: 1    
Refractivity: 40.49 m³·mol⁻¹    
Polarizability: 14.31 ų    
Number of Rings: 1

FIRST AID MEASURES of DIMETHYLANILINE:
-General advice:
Show this material safety data sheet to the doctor in attendance.

-If inhaled:
*After inhalation: 
fresh air. 
Immediately call in physician.  

-In case of skin contact:
Take off immediately all contaminated clothing. 
Rinse skin with water/ shower. 
Call a physician immediately.

-In case of eye contact:
*After eye contact: 
rinse out with plenty of water. 
Call in ophthalmologist. 
Remove contact lenses.

-If swallowed:
Give water to drink (two glasses at most). 
Seek medical advice immediately.

ACCIDENTAL RELEASE MEASURES of DIMETHYLANILINE:
-Personal precautions, protective equipment and emergency procedures:
Ensure adequate ventilation. 

-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains. 
Dispose of properly. 
Clean up affected area.

FIRE FIGHTING MEASURES of DIMETHYLANILINE:
-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 DIMETHYLANILINE:
-Control parameters:
*Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Safety glasses
*Skin protection:
Full contact:
Material: butyl-rubber
Minimum layer thickness: 0,7 mm
Break through time: 480 min

Splash contact:
Material: Latex gloves
Minimum layer thickness: 0,6 mm
Break through time: 60 min

*Body Protection:
protective clothing
-Control of environmental exposure:
Do not let product enter drains.

HANDLING and STORAGE of DIMETHYLANILINE:
-Precautions for safe handling:
*Hygiene measures:
Immediately change contaminated clothing. 
Wash hands and face after working with substance.

-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed. 
Keep in a well-ventilated place. 

STABILITY and REACTIVITY of DIMETHYLANILINE:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature) .

SYNONYMS
N,N-Dimethylbenzeneamine
Dimethylaminobenzene    
Dimethylphenylamine    
N,N-Dimethyl-N-phenylamine    
N,N-Dimethylbenzenamine    
N,N-Dimethylbenzeneamine    
N,N-Dimethylphenylamine    
N,N-(Dimethylamino)benzene    
N,N-Dimethyl-benzenamine    
N,N-Dimethylaniline sulfate (1:1)    
N,N-Dimethylaniline hydrochloride    
N,N-Dimethylaniline hydroiodide