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2,6-Dimethylaniline

2,6-Dimethylaniline structure

CAS No:
87-62-7
Formula:
C8H11N
Chemical Name:
2,6-Dimethylaniline
Synonyms:
Benzenamine,2,6-dimethyl-;2,6-Xylidine;2,6-Dimethylbenzenamine;2,6-Dimethylaniline;o-Xylidine;2-Amino-1,3-dimethylbenzene;2-Amino-1,3-xylene;2-Amino-m-xylene;1-Amino-2,6-dimethylbenzene;2,6-Xylylamine;2,6-Dimethylphenylamine;NSC 7098;2,6-Dimethylaminobenzene;1123533-24-3
Categories:
Organic Chemistry > Amides

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Description

clear yellow to red-brown liquid

2,6-Dimethylaniline Basic Attributes

Molecular Weight：

121.18

Exact Mass：

121.18

BRN：

636332

EC Number：

201-758-7

HScode：

29214910

Characteristics

PSA：

XLogP3：

1.84

Appearance：

Clear yellow to red-brown Liquid

Density：

0.9842 g/cm³ @ Temp: 20 °C

Melting Point：

11.2 °C

Boiling Point：

216 °C

Flash Point：

196 °F

Refractive Index：

1.559

Water Solubility：

H2O: 7.5 g/L (20 ºC)

Storage Conditions：

Refrigerator

Vapor Pressure：

<0.01 mm Hg ( 20 °C)

Vapor Density：

Relative vapour density (air = 1): 4.2

Toxicity：

Oral-Rat LD50: 840 mg/kg; Oral-Mouse LD50: 707 mg/kg

Flammability characteristics：

Open flame is flammable; works with oxidants; high heat decomposes toxic nitrogen oxide fumes

Explosive limit：

1.3-6.9%(V)

Odor：

Characteristic odor

Safety Information

Packing level：

Hazard category：

6.1

Transport codes：

UN 1711 6.1/PG 2

wgk germany：

hazard class code：

20/21/22-37/38-40-51/53

safety instructions：

23-25-36/37-61

RTECS Number：

ZE9275000

Marks：

Xn,N,T

Storage features：

Storehouse ventilated at low temperature and dry; stored separately from acids, oxidants, food additives

Stability/Shelf Life：

Stable under recommended storage conditions.

Precautionary statement(s)：

P261-P273-P280

Hazard Statements：

H302 + H312 + H332-H315-H335-H351-H411

Toxicity

Toxicity class：

moderately toxic

2,6-Dimethylaniline Use and Manufacturing

Methods of Manufacturing

The preparation methods are as follows. (1) Using m-xylene as raw material, it is obtained by nitrification of mixed acid and catalytic hydrogenation. The process is to cool m-xylene to 0～5℃, add the mixed acid after cooling (56.5% sulfuric acid, 28% nitric acid, 15.5% water), and keep the temperature at 17℃～25℃ for the first time. Finished, the second time was added at 17-25°C in 2h, the final drop temperature was 25-30°C, added within 1h, then stirred at 25-30°C for 30min, the nitrate was separated and washed with water, and then decompressed The crude product was obtained by distillation, and then the fraction of 78-85°C/666.5Pa was distilled and crystallized by cooling to obtain 2, 6-dimethylnitrobenzene. 2, 6-Dimethylnitrobenzene is reduced. In the past, iron powder and hydrochloric acid were used for the gradual reduction. Iron powder was gradually added to the solution of 2, 6-dimethylnitrobenzene and dilute hydrochloric acid, and then refluxed after addition. After cooling for 30 minutes, then add sodium carbonate to neutralize, add water to distill to obtain an oily solution, separate the layers, and dry the oil layer to obtain the product. Catalytic hydrogenation has been used instead of iron powder reduction. In the presence of a catalyst, 2, 6-dimethylnitrobenzene is used for catalytic hydrogenation to obtain a crude product, which is then processed to obtain a product. There are 2, 6-dimethylaniline and 2, 4-dimethylaniline produced by this method, and 2, 6-dimethylaniline accounts for a small share in the reaction process, which cannot meet the production requirements. The production of 2, 6-dimethylaniline by o-toluidine alkylation has become the focus of attention. (2) Alkylation method, that is, using o-toluidine and methanol as raw materials, in the presence of a catalyst, the reaction is carried out under a certain pressure. In this reaction, in addition to the main product 2, 6-dimethylaniline, there are many by-products, of which 2, 3-dimethylaniline and 2, 6-dimethylaniline have similar structures, similar physical properties, and boiling points The difference is small and the separation is more difficult. Generally, the alkylated reactants are first separated from other by-products such as o-toluidine and tricresidine to obtain 2, 3-dimethylaniline and 2, 6-dimethyl at a content of 98%. Aniline mixture, the mixture is used as the starting material (the content of 2, 3-dimethylaniline is 18%) through precision fractionation, the number of theoretical plates of the whole tower is more than 80, and the two components can be completely Separation gave 2, 6-dimethylaniline.

Uses

Bupivacaine (B689560) impurity.

Computed Properties

Molecular Weight:121.18
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:121.089149355
Monoisotopic Mass:121.089149355
Topological Polar Surface Area:26
Heavy Atom Count:9
Complexity:80.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

N-Methylaniline

m-Xylene

o-Toluidine

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