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1,3-Dichlorobenzene

1,3-Dichlorobenzene structure

CAS No:
541-73-1
Formula:
C6H4Cl2
Chemical Name:
1,3-Dichlorobenzene
Synonyms:
Benzene,1,3-dichloro-;Benzene,m-dichloro-;1,3-Dichlorobenzene;m-Dichlorobenzene;m-Phenylene dichloride;m-Dichlorobenzol;2,6-Dichlorobenzene;NSC 8754;2,4-Dichlorobenzene
Categories:
Agrochemicals > Pesticide Intermediates

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Description

colourless liquid There are three isomeric forms of dichlorobenzene (DCB): m-DCB is a flammable liquid and vapor.

1,3-Dichlorobenzene Basic Attributes

Molecular Weight：

147

Exact Mass：

147.00

BRN：

956618

EC Number：

208-792-1

HScode：

29036990

Characteristics

PSA：

XLogP3：

3.53

Appearance：

Clear colorless to slightly yellow Liquid

Density：

1.2884 g/cm³ @ Temp: 20 °C

Melting Point：

-24.8 °C

Boiling Point：

173 °C

Flash Point：

146 °F

Refractive Index：

1.549

Water Solubility：

H2O: 0.0123 g/100 mL (25 ºC)

Storage Conditions：

0-6°C

Vapor Pressure：

5 mm Hg ( 38.8 °C)

Vapor Density：

5.08

Toxicity：

Peritoneal-mouse LD50: 1062 mg/kg

Flammability characteristics：

Combustible in case of open flame; burning produces toxic chloride fumes; reacts with oxidants and aluminum

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

UN 3082 9/PG 3

wgk germany：

hazard class code：

22-51/53-39/23/24/25-23/24/25-11

safety instructions：

61-45-36/37-16-7

RTECS Number：

CZ4499000

Marks：

Xn,N,T,F

Storage features：

Treasury is ventilated at low temperature and dry; stored separately from oxidants and food additives

Stability/Shelf Life：

Stability Combustible. Incompatible with strong oxidizing agents, aluminium, aluminium alloys. Moisture-sensitive.

Precautionary statement(s)：

P273

Hazard Statements：

H302-H411

Toxicity

Toxicity class：

moderately toxic

1,3-Dichlorobenzene Use and Manufacturing

Methods of Manufacturing

The preparation of o-dichlorobenzene mainly includes by-product recovery of chlorobenzene and diazotization of o-chloroaniline. Dichlorobenzene is produced in the production process of chlorobenzene by-product recovery. The chlorination process conditions can be changed according to the actual demand, and the production ratio of chlorobenzene and dichlorobenzene can be adjusted. According to the current process control conditions and production situation of chlorobenzene production, the ratio of chlorobenzene and dichlorobenzene is 30～(35:1). The industrial separation of o-dichlorobenzene and p-dichlorobenzene mainly includes rectification and crystallization. The o-chloroaniline diazotization method uses o-chloroaniline as a raw material and is prepared by diazotization and displacement reaction. Add o-chloroaniline and hydrochloric acid into the reaction pot, mix well below 25°C, cool to 0°C, drop in sodium nitrite solution, control the temperature at 0～5°C, stop feeding when the potassium iodide starch indicator turns blue, get Diazonium salt solution. Then add the diazonium salt solution to the hydrochloric acid solution of cuprous chloride at 0～5℃, stir well, heat up to 60～70℃ and react for 1h. After cooling, let it stand for layering. Use 5% sodium hydroxide for the oil layer. Repeated washing with water, dehydration with anhydrous calcium chloride, fractional distillation, collecting 177～183℃ distillate, then the product o-dichlorobenzene is obtained. Chlorobenzene as a raw material is further chlorinated with chlorobenzene as a raw material, and p-dichlorobenzene and o-dichlorobenzene can be obtained at the same time, and then p-dichlorobenzene and o-dichlorobenzene can be obtained by fractional distillation.

Uses

Used in organic synthesis. Friedel-Crafts reaction between m-dichlorobenzene and chloroacetyl chloride yields 2,4,ω-trichloroacetophenone, which is used as an intermediate for the broad-spectrum antifungal drug miconazole. In the presence of ferric chloride or aluminum mercury, the chlorination reaction mainly produces 1,2,4-trichlorobenzene. In the presence of a catalyst, it is hydrolyzed at 550-850°C to generate m-chlorophenol and resorcinol. Using copper oxide as a catalyst, it reacts with concentrated ammonia at 150-200°C under pressure to produce m-phenylenediamine.

Computed Properties

Molecular Weight:147.00
XLogP3:3.5
Exact Mass:145.9690055
Monoisotopic Mass:145.9690055
Heavy Atom Count:8
Complexity:64.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Calcium chloride

Chlorobenzene

Sodium nitrite

Potassium iodide

Cuprous chloride

1,2-Dichlorobenzene

Downstream Products

1,4-Dichlorobenzene

2′,4′-Dichloroacetophenone

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