1,3-Dichlorobenzene
1,3-Dichlorobenzene
CAS: 541-73-1
Molecular Formula: C6H4Cl2
1,3-Dichlorobenzene - Names and Identifiers
| Name | 1,3-Dichlorobenzene |
| Synonyms | NSC 8754 1.3-Dichlorobe Twochlorobenzene m-Dichlorobenzene m-Dichloro Benzene 1,3-Dichlorobenzene 2,6-Dichlorobenzene Benzene, m-dichloro- 1,3-Dichloro Benzene Benzene,1,3-dichloro- Meta Dichloro Benzene Benzene, M-dichloro- (8CI) |
| CAS | 541-73-1 |
| EINECS | 208-792-1 |
| InChIKey | ZPQOPVIELGIULI-UHFFFAOYSA-N |
1,3-Dichlorobenzene - Physico-chemical Properties
| Molecular Formula | C6H4Cl2 |
| Molar Mass | 147 |
| Density | 1.288 g/mL at 25 °C (lit.) |
| Melting Point | -25--22 °C (lit.) |
| Boling Point | 172-173 °C (lit.) |
| Flash Point | 146°F |
| Water Solubility | 0.0123 g/100 mL (25 ºC) |
| Solubility | Difficult to mix. |
| Vapor Presure | 5 mm Hg ( 38.8 °C) |
| Appearance | Liquid |
| Color | Clear colorless to slightly yellow |
| Odor | Pleasant odor |
| Merck | 14,3055 |
| BRN | 956618 |
| Storage Condition | 2-8°C |
| Stability | Stability Combustible. Incompatible with strong oxidizing agents, aluminium, aluminium alloys. Moisture-sensitive. |
| Refractive Index | n20/D 1.546(lit.) |
| Physical and Chemical Properties | Properties colorless liquid freezing point -24 ℃ refractive index 1.5457 solubility soluble in ethanol, ether, insoluble in water. |
| Use | Widely used in dyes, pharmaceuticals, pesticides and other industries intermediates |
1,3-Dichlorobenzene - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R39/23/24/25 - R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R11 - Highly Flammable |
| Safety Description | S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37 - Wear suitable protective clothing and gloves. S16 - Keep away from sources of ignition. S7 - Keep container tightly closed. |
| UN IDs | UN 3082 9/PG 3 |
| WGK Germany | 2 |
| RTECS | CZ4499000 |
| TSCA | Yes |
| HS Code | 29036990 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 orally in Rabbit: 580 mg/kg |
1,3-Dichlorobenzene - Upstream Downstream Industry
| Raw Materials | 1,3-Dinitrobenzene Chlorine Nitrobenzene |
| Downstream Products | 2,4-Difluoroaniline |
1,3-Dichlorobenzene - Nature
Open Data Verified Data
colorless liquid. Boiling point 172 °c. Freezing point -24 ℃, relative density 1. 288. Refractive index 5457. Soluble in ethanol, ether, insoluble in water.
Last Update：2024-01-02 23:10:35
1,3-Dichlorobenzene - Preparation Method
Open Data Verified Data
- M-Phenylenediamine and sulfuric acid, sodium nitrite by diazotization reaction, made of diazonium salt, then by chlorination.
- M-chloroaniline is produced by diazotization and chlorination.
- direct catalytic chlorination of M-dinitrobenzene.
Last Update：2022-01-01 10:40:35
1,3-Dichlorobenzene - Use
Open Data Verified Data
raw materials for organic synthesis.
Last Update：2022-01-01 10:40:34
1,3-Dichlorobenzene - Safety
Open Data Verified Data
see O-dichlorobenzene.
Last Update：2022-01-01 10:40:35
1,3-Dichlorobenzene - Reference Information
| freezing point | -24 ℃ |
| Henry's Law Constant | 2.14 at 20.00 °C (inert gas stripping, Hovorka and Dohnal, 1997) |
| LogP | 3.53 at 22℃ |
| (IARC) carcinogen classification | 3 (Vol. 73) 1999 |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Uses | o-dichlorobenzene is an important organic chemical raw material. It is the raw material of the insecticide trichloroinsecticidal ester in pesticides and is used to synthesize its intermediate 1-(3, 4-dichlorophenyl)-2,2, 2-trichloroethanol, and can also synthesize another important pesticide intermediate o-phenylenediamine. In addition, it is also used as a solvent for dye, medicine, resin, rubber and other operations, or as a rust remover, degreasing agent and so on. used in dye manufacturing, also used as organic synthesis intermediates and solvents widely used as intermediates in dyes, pharmaceuticals, pesticides and other industries m-dichlorobenzene is an important organic synthesis raw material, is the raw material of fungicides pyimazole, propiconazole and ethicyclazole, and is also the raw material of insecticide insecticide. Used in organic synthesis. The Friedel-Crafts reaction between m-dichlorobenzene and chloroacetyl chloride gives 2,4,ω-trichloroacetophenone, which is used as an intermediate of miconazole, a broad-spectrum antifungal drug. The chlorination reaction is carried out in the presence of ferric chloride or aluminum mercury, which mainly produces 1,2, 4-trichlorobenzene. In the presence of a catalyst, m-chlorophenol and resorcinol were hydrolyzed at 550-850°C. Using copper oxide as a catalyst, it reacts with concentrated ammonia at 150-200°C under pressure to form m-phenylenediamine. |
| production method | 1. m-phenylenediamine reacts with sulfuric acid and sodium nitrite through diazotization to prepare diazonium salt, which is then chlorinated. 2. m-chloroaniline is formed by diazotization and chlorination. 3. Direct catalytic chlorination with m-dinitrobenzene. There are several preparation methods. Chlorobenzene is used as raw material for further chlorination to obtain p-dichlorobenzene, o-dichlorobenzene and m-dichlorobenzene. The general separation method uses mixed dichlorobenzene for continuous distillation, the top of the tower distillates para-and meta-dichlorobenzene, frozen crystallization to precipitate p-dichlorobenzene, and the mother liquor is rectified to obtain meta-dichlorobenzene, the tower kettle is crude o-dichlorobenzene, and then flash distillation in the flash tower to produce o-dichlorobenzene. At present, the mixed dichlorobenzene adopts the adsorption separation method, using molecular sieve as the adsorbent, and the gas phase mixed dichlorobenzene enters the adsorption tower, which can selectively adsorb p-dichlorobenzene, and the absorbent is meta-and ortho-dichlorobenzene. After rectification, m-dichlorobenzene and o-dichlorobenzene were obtained respectively. The adsorption temperature is 180~200 ℃, and the adsorption pressure is normal pressure. m-phenylenediamine diazo method m-phenylenediamine is diazotized in the presence of sodium nitrite and sulfuric acid. The diazotization temperature is 0~5 ℃, and the diazonium solution is hydrolyzed in the presence of cuprous chloride to generate m-dichlorobenzene. The m-chloroaniline method uses m-chloroaniline as raw material, diazotization is carried out in the presence of sodium nitrite and hydrochloric acid, and the diazo solution is hydrolyzed in the presence of cuprous chloride to generate m-dichlorobenzene. Among the above preparation methods, the most suitable for industrialization and lower cost method is the adsorption separation method of mixed dichlorobenzene. There are already production units in China for production. the preparation of o-dichlorobenzene mainly includes the recovery of by-products of chlorobenzene and diazotization of o-chloroaniline. Chlorobenzene by-product recovery Dichlorobenzene is produced during the production of chlorobenzene. According to the actual demand, the chlorination process conditions can be changed to adjust the ratio of chlorobenzene to dichlorobenzene. According to the current process control conditions and production conditions of chlorobenzene production, the ratio of chlorobenzene to dichlorobenzene is 30 ~(35: 1). The industrial separation methods of o-dichlorobenzene and p-dichlorobenzene mainly include rectification and crystallization. O-chloroaniline diazotization method using o-chloroaniline as raw material, through diazotization and replacement reaction. Add o-chloroaniline and hydrochloric acid to the reaction pot, mix well below 25 ℃, cool to 0 ℃, drop sodium nitrite solution, control the temperature at 0~5 ℃, stop feeding when the potassium iodide starch indicator turns blue, and obtain diazonium salt solution. Then the diazonium salt solution is added into the hydrochloric acid solution of cuprous chloride at 0-5 ℃, stirred evenly, heated to 60-70 ℃ for 1h, cooled and let stand for stratification, the oil layer is repeatedly washed with 5% sodium hydroxide and water, dehydrated with anhydrous calcium chloride, fractionated, and collected the fraction at 177-183 ℃ to obtain the product o-dichlorobenzene. Chlorobenzene is used as raw material for further chlorination of chlorobenzene, and p-dichlorobenzene and o-dichlorobenzene can be obtained at the same time, and p-dichlorobenzene and o-dichlorobenzene can be obtained by fractionation. |
| category | flammable liquid |
| toxicity classification | poisoning |
| acute toxicity | abdominal cavity-mouse LD50: 1062 mg/kg |
| flammability hazard characteristics | Combustible in open flame; Combustion produces toxic chloride smoke; Reacts with oxidant and aluminum |
| storage and transportation characteristics | warehouse ventilation and low temperature drying; Store separately from oxidants and food additives |
| fire extinguishing agent | carbon dioxide, foam, sand, mist water. |
| spontaneous combustion temperature | >500°C |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:09
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Raw Materials for 1,3-Dichlorobenzene
Downstream Products for 1,3-Dichlorobenzene