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121-69-7

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Identification

Name
N,N-Dimethylaniline
CAS
121-69-7
Synonyms
acetdimethylamide
ACETIC ACID DIMETHYLAMIDE
ACETYL DIMETHYLAMINE
AKOS BBS-00004263
AKOS BBS-00004374
AMINODIMETHYLBENZENE
DIMETHYL ACETAMIDE
DIMETHYLAMINOBENZENE
DIMETHYLPHENYLAMINE
DMA
DMAC
LABOTEST-BB LT00782487
N-ACETYLDIMETHYLAMINE
N,N-DIMETHYLACETAMIDE
N,N-DIMETHYLACETATE
u-5954
Aniline, N,N-dimethyl-
Benzenamine,N,N-dimethyl-
Dimethylanilin
Dimethylaniline,N-N-dimethylphenylamine
EINECS(EC#)
204-493-5
Molecular Formula
C8H11N
MDL Number
MFCD00008304
Molecular Weight
121.18
MOL File
121-69-7.mol

Chemical Properties

Appearance
liquid
Melting point 
1.5-2.5 °C (lit.)
mp 
1.5-2.5 °C(lit.)

Boiling point 
193-194 °C (lit.)
bp 
193-194 °C(lit.)

density 
0.956 g/mL at 20 °C
vapor density 
3 (vs air)

vapor pressure 
2 mm Hg ( 25 °C)

refractive index 
n20/D 1.557(lit.)

Fp 
158 °F

storage temp. 
0-6°C
solubility 
1.2g/l
pka
5.15(at 25℃)
form 
Liquid
color 
Clear yellow
PH
7.4 (1.2g/l, H2O, 20℃)
Stability:
Stable. Incompatible with strong oxidizing agents, strong acids, acid chlorides, acid anhydrides, chloroformates, halogens. Combustible.
Relative polarity
0.179
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).
InChIKey
JLTDJTHDQAWBAV-UHFFFAOYSA-N
CAS DataBase Reference
121-69-7(CAS DataBase Reference)
NIST Chemistry Reference
Benzenamine, N,N-dimethyl-(121-69-7)
IARC
3 (Vol. 57) 1993
EPA Substance Registry System
121-69-7(EPA Substance)

Safety Data

Hazard Codes 
T,N
Risk Statements 
R61:May cause harm to the unborn child.
R20/21:Harmful by inhalation and in contact with skin .
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R40:Limited evidence of a carcinogenic effect.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
Safety Statements 
S53:Avoid exposure-obtain special instruction before use .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S36/37:Wear suitable protective clothing and gloves .
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
RIDADR 
UN 2253 6.1/PG 2

WGK Germany 
3

RTECS 
BX4725000


8
Autoignition Temperature
370 °C DIN 51794
TSCA 
Yes
HazardClass 
6.1
PackingGroup 
II
HS Code 
29214200
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.
Hazardous Substances Data
121-69-7(Hazardous Substances Data)
Toxicity
LD50 orally in rats: 1.41 ml/kg (Smyth)

Raw materials And Preparation Products

Hazard Information

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.
Reactivity Profile
Explosive decomposition occurred when finely divided benzoyl peroxide was allowed to react with N,N-DIMETHYLANILINE(121-69-7) 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.
Air & Water Reactions
Insoluble in water.
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.
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.
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
Solvent; manufacture of vanillin, Michler's ketone, methyl violet and other dyes. As reagent for methanol, methyl furfural, H2O2, nitrate, alcohol, formaldehyde.
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
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).
Definition
ChEBI: A tertiary amine that is aniline in which the amino hydrogens are replaced by two methyl groups.
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).
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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