| Identification | More | [Name]
2,6-Dimethylaniline | [CAS]
87-62-7 | [Synonyms]
1-Amino-2,6-dimethylbenzene
2,6-DIMETHYLANILINE
2,6-XYLIDINE
2-AMINO-1,3-DIMETHYLBENZENE
2-AMINO-M-XYLENE
AKOS BBS-00003564
DIMETHYLANILINE,2,6-
LABOTEST-BB LTBB000551
TIMTEC-BB SBB008136
VIC-M-XYLIDINE
xylylamine
2,6-dimethyl-anilin
2,6-dimethyl-benzenamin
2,6-Dimethylbenzenamine
2,6-dimethyl-Benzenamine
2,6-Dimethylbenzeneamine
2,6-dimethylphenylamine
2,6-Dimethyl-phenylamine
2,6-DMA
2,6-Xyildine | [EINECS(EC#)]
201-758-7 | [Molecular Formula]
C8H11N | [MDL Number]
MFCD00007747 | [Molecular Weight]
121.18 | [MOL File]
87-62-7.mol |
| Chemical Properties | Back Directory | [Appearance]
clear yellow to red-brown liquid | [Melting point ]
10-12 °C(lit.)
| [Boiling point ]
216 °C | [density ]
0.984 g/mL at 25 °C(lit.)
| [vapor pressure ]
<0.01 mm Hg ( 20 °C)
| [refractive index ]
n20/D 1.560(lit.)
| [Fp ]
196 °F
| [storage temp. ]
Store below +30°C. | [solubility ]
13g/l | [form ]
Liquid | [pka]
3.89(at 25℃) | [color ]
Clear yellow to red-brown | [PH]
12.5 (100g/l, H2O, 20℃) | [PH Range]
12.5 | [explosive limit]
1.3-6.9%(V) | [Water Solubility ]
7.5 g/L (20 ºC) | [Detection Methods]
HPLC,NMR | [Merck ]
14,10084 | [BRN ]
636332 | [Stability:]
Air Sensitive, Hygroscopic | [LogP]
1.840 | [CAS DataBase Reference]
87-62-7(CAS DataBase Reference) | [IARC]
2B (Vol. 57) 1993 | [NIST Chemistry Reference]
Benzenamine, 2,6-dimethyl-(87-62-7) | [EPA Substance Registry System]
87-62-7(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,N,T | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R37/38:Irritating to respiratory system and skin .
R40:Limited evidence of a carcinogenic effect.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S25:Avoid contact with eyes .
S36/37:Wear suitable protective clothing and gloves .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
UN 1711 6.1/PG 2
| [WGK Germany ]
2
| [RTECS ]
ZE9275000
| [F ]
8 | [Autoignition Temperature]
490 °C | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29214910 | [Safety Profile]
Suspected carcinogen.
Moderately toxic by ingestion. Mutation data
reported. Questionable carcinogen with
experimental carcinogenic data. When
heated to decomposition it emits toxic
fumes of NOx. See also other xylidme
entries. | [Hazardous Substances Data]
87-62-7(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 1290 mg/kg |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
o-Toluidine-->N-Methylaniline-->m-Xylene-->2,6-Dimethylphenol-->2,4-Dimethyl aniline-->2,6-Dimethyl-1-nitrobenzene-->CYCLOXYDIM | [Preparation Products]
Alachlor-->Metalaxyl-->Tetramethylbenzidine-->2,6-Dimethylbenzyl alcohol-->2',6'-DIMETHYLACETANILIDE-->N-(2,6-DIMETHYLPHENYLCARBAMOYLMETHYL)IMINODIACETIC ACID-->Benalaxyl-->Oxadixyl-->Ropivacaine-->Bupivacaine-->1-(2,6-DIMETHYLPHENYL)PIPERAZINE-->Metazachlor-->PILSICAINIDE-->Nefiracetam-->(2,6-DIMETHYL-PHENYL)-HYDRAZINE-->(±)-N-(2,6-dimethylphenyl)-2-(ethylpropylamino)butyramide monohydrochloride-->2-Chloro-N-(2,6-dimethylphenyl)acetamide-->Benzenamine, N-butyl-2,6-dimethyl--->2-(2,6-DIMETHYLPHENYL)ETHANOL-->Acid Orange 134-->3-[[4-[[6-[(4-Aminobenzoyl)amino]-1-hydroxy-3-sulfo-2-naphtyl]azo]-3,5-dimethylphenyl]azo]-1,5-naphthalenedisulfonic acid trisodium salt |
| Hazard Information | Back Directory | [General Description]
A liquid. Toxic by ingestion, inhalation and skin absorption. Slightly soluble in water. Used in pharmaceuticals, as dye intermediates and organic syntheses. | [Reactivity Profile]
2,6-XYLIDINE(87-62-7) reacts with strong oxidizing agents [Handling Chemicals Safely 1980 p. 964]. Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides. | [Air & Water Reactions]
Slightly soluble in water. | [Health Hazard]
May be fatal if inhaled, swallowed or absorbed through skin. Vapor or mist irritating to the eyes, mucous membranes and upper respiratory tract; causes skin irritation. Absorption into body leads to the formation of methemoglobin which, in sufficient concentration, may cause cyanosis. Onset may be delayed 2-4 hours or longer. Exposure can cause nausea, dizziness, headache, damage to the eyes, and blood effects. | [Fire Hazard]
Special Hazards of Combustion Products: Container explosion may occur under fire conditions. Emits toxic fumes under fire conditions. | [Chemical Properties]
clear yellow to red-brown liquid | [Uses]
Bupivacaine (B689560) impurity. | [Definition]
ChEBI: A primary arylamine that is aniline in which the hydrogens at the 2- and 6-positions are replaced by methyl groups. It is used in the production of some anasthetics and other chemicals. It is a drug metabolite of lidocaine (local anasthetic). | [Preparation]
2,6-Dimethylaninile is prepared by nitration of xylene and reduction, followed by removal of the 2,4-isomer by formation of the acetate salt, removal of the 2,5-isomer by formation of the hydrochloride salt, and recovery of the 2,6-isomer by sublimation (US National Library of Medicine, 1992a).
2,6-Dimethylaniline is produced by one company each in Japan, Switzerland and the USA and by three companies in Germany (Chemical Information Servces, 1991). | [Synthesis Reference(s)]
Journal of the American Chemical Society, 92, p. 7464, 1970 DOI: 10.1021/ja00728a038
The Journal of Organic Chemistry, 37, p. 3570, 1972 | [Purification Methods]
Convert vic-xylidine to a derivative (see below) which, after recrystallisation, is decomposed with alkali to give the free base. Dry it over KOH and fractionally distil. The acetyl derivative has m 177o, the benzoyl derivative has m 168o, and the picrate has m 180o. [Beilstein 12 H 1107, 12 IV 2521.] |
|
|