ChemicalBook > CAS DataBase List > N,N-Dimethylaniline

N,N-Dimethylaniline

Product Name
N,N-Dimethylaniline
CAS No.
121-69-7
Chemical Name
N,N-Dimethylaniline
Synonyms
DMA;HLADM;RING6;D6S222E;nl63-10p;Xylidene;NSC 7195;NCI-C56428;N.N-Dimethylan;Dimethylanilin
CBNumber
CB6852937
Molecular Formula
C8H11N
Formula Weight
121.18
MOL File
121-69-7.mol
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N,N-Dimethylaniline Property

Melting point:
1.5-2.5 °C (lit.)
Boiling point:
193-194 °C (lit.)
Density 
0.956 g/mL at 25 °C (lit.)
vapor density 
3 (vs air)
vapor pressure 
2 mm Hg ( 25 °C)
refractive index 
n20/D 1.557(lit.)
Flash point:
158 °F
storage temp. 
Store below +30°C.
solubility 
1.2g/l
pka
5.15(at 25℃)
form 
Liquid
color 
Clear yellow
Relative polarity
0.179
PH
7.4 (1.2g/l, H2O, 20℃)
explosive limit
1.2-7%(V)
Water Solubility 
1 g/L (20 ºC)
Merck 
14,3234
BRN 
507140
Henry's Law Constant
4.98(x 10-6 atm?m3/mol) at 20 °C (approximate - calculated from water solubility and vapor pressure)
Exposure limits
NIOSH REL: TWA 5 ppm (25 mg/m3), STEL 10 ppm (50 mg/m3), IDLH 100 ppm; OSHA PEL: TWA 5 ppm; ACGIH TLV: TWA 5 ppm, STEL 10 ppm (adopted).
Stability:
Stable. Incompatible with strong oxidizing agents, strong acids, acid chlorides, acid anhydrides, chloroformates, halogens. Combustible.
InChIKey
JLTDJTHDQAWBAV-UHFFFAOYSA-N
CAS DataBase Reference
121-69-7(CAS DataBase Reference)
IARC
3 (Vol. 57) 1993
NIST Chemistry Reference
Benzenamine, N,N-dimethyl-(121-69-7)
EPA Substance Registry System
N,N-Dimethylaniline (121-69-7)
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Safety

Hazard Codes 
T,N
Risk Statements 
61-20/21-51/53-40-23/24/25
Safety Statements 
53-45-61-36/37-28A-28
RIDADR 
UN 2253 6.1/PG 2
WGK Germany 
3
RTECS 
BX4725000
8
Autoignition Temperature
370 °C DIN 51794
TSCA 
Yes
HS Code 
2921 42 00
HazardClass 
6.1
PackingGroup 
II
Hazardous Substances Data
121-69-7(Hazardous Substances Data)
Toxicity
LD50 orally in rats: 1.41 ml/kg (Smyth)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H227Combustible liquid

H301Toxic if swalloed

H311Toxic in contact with skin

H319Causes serious eye irritation

H331Toxic if inhaled

H336May cause drowsiness or dizziness

H341Suspected of causing genetic defects

H351Suspected of causing cancer

H370Causes damage to organs

H372Causes damage to organs through prolonged or repeated exposure

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P273Avoid release to the environment.

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

P311Call a POISON CENTER or doctor/physician.

P391Collect spillage. Hazardous to the aquatic environment

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P307+P311IF exposed: call a POISON CENTER or doctor/physician.

P370+P378In case of fire: Use … for extinction.

P405Store locked up.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.03060
Product name
N,N-Dimethylaniline
Purity
for synthesis
Packaging
100 mL
Price
$24.7
Updated
2021/03/22
Sigma-Aldrich
Product number
8.03060
Product name
N,N-Dimethylaniline
Purity
for synthesis
Packaging
500 mL
Price
$34.78
Updated
2021/03/22
Sigma-Aldrich
Product number
8.03060
Product name
N,N-Dimethylaniline
Purity
for synthesis
Packaging
1 L
Price
$47.17
Updated
2021/03/22
Sigma-Aldrich
Product number
407275
Product name
N,N-Dimethylaniline
Purity
purified by redistillation, ≥99.5%
Packaging
100ml
Price
$71.2
Updated
2021/03/22
Sigma-Aldrich
Product number
8.03060
Product name
N,N-Dimethylaniline
Purity
for synthesis
Packaging
2.5 L
Price
$76.96
Updated
2021/03/22
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N,N-Dimethylaniline Chemical Properties,Usage,Production

Chemical Properties

Straw to brown-colored oily liquid with a characteristic amine-like odor. Odor threshold concentration is 13 ppb (quoted, Amoore and Hautala, 1983).

Physical properties

Straw to brown-colored oily liquid with a characteristic amine-like odor. Odor threshold concentration is 13 ppb (quoted, Amoore and Hautala, 1983).

Uses

N,N-Dimethylaniline is used in production of dyestuffs, as a solvent, a reagent in methylation reactions, and a hardener in fiberglass reinforced resins.

Uses

Intermediate in the manufacture of dyes; solvent; rubber vulcanizing agent and stabilizer

Uses

Solvent; manufacture of vanillin, Michler's ketone, methyl violet and other dyes. As reagent for methanol, methyl furfural, H2O2, nitrate, alcohol, formaldehyde.

Definition

ChEBI: A tertiary amine that is aniline in which the amino hydrogens are replaced by two methyl groups.

Production Methods

N,N-Dimethylaniline is made by heating aniline, methyl alcohol and sulfuric acid under pressure, followed by hydrolysis of the sulfate formed with sodium hydroxide to the free base (Windholz et al 1983). United States production in 1975 was estimated at 4,600 metric tons (HSDB 1989).

General Description

A yellow to brown colored oily liquid with a fishlike odor. Less dense than water and insoluble in water. Flash point 150°F. Toxic by ingestion, inhalation, and skin absorption. Used to make dyes and as a solvent.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Explosive decomposition occurred when finely divided benzoyl peroxide was allowed to react with N,N-Dimethylaniline by breaking an ampoule containing 0.5 grams of dimethylaniline in an autoclave, NFPA 491M, 1991. This result may be expected with other peroxides and various oxidants.

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Health Hazard

Clinical signs of intoxication with N,N-dimethylaniline in man are headaches, cyanosis, dizziness, labored breathing, paralysis and convulsions (HSDB 1989). It is absorbed through the skin to produce a dangerous methemoglobinemia (Gosselin 1984). Treatment is similar to that of aniline with the object of managing methemoglobinemia.

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

Industrial uses

N,N-Dimethylaniline is used as chemical intermediate in the manufacturing of vanillin, Michler's ketone, and dyes such as Acid Red 2, Basic Green 4 and Basic Violet 1 (Northcott 1978). It is also used as a solvent and an activator for polyesters and as an alkylating agent (Beard and Noe 1981). It is used as an acid scavenger or accepter in the manufacture of beta-lactam antibiotics such as penicillin and cephalosporin (Nachtmann and Gstrein 1981).

Safety Profile

Suspected carcinogen with equivocal tumorigenic data. Human poison by ingestion. Moderately toxic by inhalation and skin contact. A skin irritant. Human systemic effects by ingestion: nausea or vomiting. Physiological action is similar to, but less toxic than, adne. A central nervous system depressant. Mutation data reported. Flammable liquid when exposed to heat, flame, or oxidizers. Explodes on contact with benzoyl peroxide or disopropyl peroxydicarbonate. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits htghly toxic fumes of adne and NOx. See also ANILINE.

Carcinogenicity

A 2-year corn oil gavage bioassay conducted by NTP in F344/N rats (0.3 or 30 mg/kg) and B6C3F1 mice (0, 15, or 30 mg/kg) for 103 weeks concluded that there was some evidence of carcinogenic activity for male F344/N rats as indicated by the increased incidences of sarcomas or osteosarcomas in the spleen; there was no evidence of carcinogenic activity in the female rats or male mice; there was equivocal evidence of carcinogenic activity for female mice as indicated by an increased incidence of squamous cell papillomas of the forestomach. Both rats and mice could have tolerated doses higher than those used in these studies.

Environmental Fate

Photolytic. A rate constant of 1.48 x 10-10 cm3/molecule?sec was reported for the reaction of N,N-dimethylaniline and OH radicals in air at room temperature (Atkinson et al., 1987).
Chemical/Physical. Products identified from the gas-phase reaction of ozone with N,Ndimethylaniline in synthetic air at 23 °C were: N-methylformanilide, formaldehyde, formic acid, hydrogen peroxide, and a nitrated salt having the formula: [C6H6NH(CH3)2]+NO3 - (Atkinson et al., 1987). Reacts with acids forming water-soluble salts.

Metabolism

Ν,Ν-Dimethylaniline undergoes N-demethylation, N-oxidation, and ring hydroxylation in animals. Urinary metabolites produced by dogs and rabbits injected with this compound included 4-aminophenol, 4-dimethylaminophenol, 2-aminophenol and N-methylaniline (Williams 1959; Kiese and Renner 1974). N-oxidation, N-demethylation and ring hydroxylation of Ν,Ν-dimethylaniline was demonstrated in vitro using liver microsomal preparations from pigs, rats, rabbits, chickens, and guinea pigs (Fish et al 1955; Zeigler and Pettit 1964, 1966; Abou-Donia and Menzel 1968). N-oxidation was also demonstrated using whole homogenate of human liver (Zeigler and Gold 1971; Rane 1974). Evidence has been obtained with rabbit liver microsomes for two pathways for Ν,Ν-dimethylaniline N-oxidation (Hlavica and Kehl 1977). One pathway involves cytochrome P-450 while the second makes use of flavin-containing monooxygenase. N,N-Dimethylaniline was also metabolized to formaldehyde in the nasal and respiratory mucosa of Fischer 344 rats (McNulty et al 1983). Alveolar type II cells from rabbit and rat lungs catalyzed the N-oxidation of this compound (Devereux and Fouts 1974; Ohmiya and Mehendale 1981). The microsomal preparation from rat seminal vesicles when fortified with arachidonic acid catalyzed the dealkylation of N,Ndimethylaniline (Sivarajah et al 1982).

Purification Methods

Primary and secondary amines (including aniline and monomethylaniline) can be removed by refluxing for 4-5hours with excess acetic anhydride, and then fractionally distilling. Crocker and Jones (J Chem Soc 1808 1959) used four volumes of acetic anhydride, then distilled off the greater part of it, and dissolved the residue in ice-cold dilute HCl. Non-basic materials were removed by ether extraction, then the dimethylaniline was liberated with ammonia, extracted with ether, dried, and distilled under reduced pressure. Metzler and Tobolsky (J Am Chem Soc 76 5178 1954) refluxed with only 10% (w/w) of acetic anhydride, then cooled and poured it into excess 20% HCl, which, after cooling, was extracted with diethyl ether. (The amine hydrochloride remains in the aqueous phase.) The HCl solution was cautiously made alkaline to phenolphthalein, and the amine layer was drawn off, dried over KOH and fractionally distilled under reduced pressure, under nitrogen. Suitable drying agents for dimethylaniline include NaOH, BaO, CaSO4, and CaH2. Other purification procedures include the formation of the picrate (m 163o from Me2CO or EtOH/H2O), prepared in *benzene solution and crystallised to constant melting point, then decomposed with warm 10% NaOH and extracted into ether: the extract was washed with water and distilled under reduced pressure. The oxalate salt has also been used for purification. The base has been fractionally crystallised by partial freezing and also from aqueous 80% EtOH then from absolute EtOH. It has been distilled from zinc dust, under nitrogen. [Beilstein 12 H 141, 12 I 151, 12 II 2, 12 III 245, 12 IV 243.]

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N,N-Dimethylaniline Suppliers

Wuhan hongde yuexin pharmaceutical technology co. LTD
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027-83855395- ;027-83855395-
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QQ2365031873
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wuhanfudechem23@163.com;wuhanfudechem23@163.com
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China
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Xiangshui Henryda Tech Chemical Co., Ltd.
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0512-63863327
Fax
+86-512-69233657
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sales@henryda-chem.com
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China
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Jinan Hui Feng Da chemical Co., LTD.
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0531-88691900- ;0531-89701765- ;0531-88691900-
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0531-89702765
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jnhuifengda@163.com;3148353978@qq.com;3388693927@qq.com
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Tianjin Zhongxin Chemtech Co., Ltd.
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022-66880623;022-89880623
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86(0)22-66880086
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sales@tjzxchem.com;sales@tjzxchem.com
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J & K SCIENTIFIC LTD.
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010-82848833- ;010-82848833-
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Meryer (Shanghai) Chemical Technology Co., Ltd.
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21-61259100-
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86-21-61259102
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Alfa Aesar
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400-610-6006; 021-67582000
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021-67582001/03/05
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saleschina@alfa-asia.com
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China
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TCI (Shanghai) Development Co., Ltd.
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021-67121386 / 800-988-0390
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021-67121385
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Sales-CN@TCIchemicals.com
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Beijing dtftchem Technology Co., Ltd.
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010-60275820-
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010-60270825
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Energy Chemical
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021-58436166
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sales8178@energy-chemical.com
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View Lastest Price from N,N-Dimethylaniline manufacturers

Xingtai Haoxun Import and Export Trade Co., Ltd.
Product
N,N-dimethylaniline 121-69-7
Price
US $150.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10tons
Release date
2020-07-15
Hebei Senko Biotechnology Co., Ltd.
Product
N,N-Dimethylaniline 121-69-7
Price
US $100.00/Kg/Bag
Min. Order
1KG
Purity
99%
Supply Ability
10 Tons
Release date
2021-07-21
Shijiazhuang Erche Biotechnology Co., Ltd
Product
N,N-Dimethylaniline 121-69-7
Price
US $10.00/KG
Min. Order
1KG
Purity
≥99%
Supply Ability
10000kg
Release date
2021-06-21

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