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2,6-Dimethylaniline

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2,6-Dimethylaniline Basic information

Product Name:
2,6-Dimethylaniline
Synonyms:
  • 2,6-Xylidine, 2-Amino-m-xylene
  • 2,6-Dimethylaniline Solution, 100ppm
  • 2,6-two Methyl aniline
  • 2.6-DiMethylan
  • ai3-52358
  • Aniline, 2,6-dimethyl-
  • NCI-C56188
  • 2,6-Dimethylaniline (Lidocaine RCA)
CAS:
87-62-7
MF:
C8H11N
MW:
121.18
EINECS:
201-758-7
Product Categories:
  • Amines, Aromatics, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
  • Intermediates
  • Aromatic Amine
  • Building Blocks
  • C8
  • Chemical Synthesis
  • Nitrogen Compounds
  • Organic Building Blocks
  • Aniline
  • Anilines, Aromatic Amines and Nitro Compounds
  • Organics
  • Amines
  • Aromatics
  • Impurities
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
Mol File:
87-62-7.mol
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2,6-Dimethylaniline Chemical Properties

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.)
Flash point:
196 °F
storage temp. 
Refrigerator
solubility 
13g/l
form 
Liquid
pka
3.89(at 25℃)
color 
Clear yellow to red-brown
PH Range
12.5
PH
12.5 (100g/l, H2O, 20℃)
explosive limit
1.3-6.9%(V)
Water Solubility 
7.5 g/L (20 ºC)
Merck 
14,10084
BRN 
636332
CAS DataBase Reference
87-62-7(CAS DataBase Reference)
NIST Chemistry Reference
Benzenamine, 2,6-dimethyl-(87-62-7)
IARC
2B (Vol. 57) 1993
EPA Substance Registry System
2,6-Xylidine (87-62-7)
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Safety Information

Hazard Codes 
Xn,N,T
Risk Statements 
20/21/22-37/38-40-51/53
Safety Statements 
23-25-36/37-61
RIDADR 
UN 1711 6.1/PG 2
WGK Germany 
2
RTECS 
ZE9275000
8
Autoignition Temperature
490 °C
TSCA 
Yes
HazardClass 
6.1
PackingGroup 
II
HS Code 
29214910
Hazardous Substances Data
87-62-7(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 1290 mg/kg

MSDS

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2,6-Dimethylaniline Usage And Synthesis

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).

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

General Description

A liquid. Toxic by ingestion, inhalation and skin absorption. Slightly soluble in water. Used in pharmaceuticals, as dye intermediates and organic syntheses.

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

2,6-Dimethylaniline 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.

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.

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.

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.]

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