1,3-Dichlorbenzol
MDCB · M-DICHLOROBENZENE · Benzene, m-dichloro- · meta-dichlorobenzene · 1.3-Dichlorobe · 1,3-Dichlorbenzol · 1,3-dichlorbenzene · Metadichlorobenzene

Identifikatoren & physikalische Daten
| CAS No. | 541-73-1 |
|---|---|
| Summenformel | C6H4Cl2 |
| Durchschnittliche Molmasse | 147 g/mol |
| Monoisotopische Masse | 145,96900549 g/mol |
| SMILES | Clc1cccc(Cl)c1 |
| InChIKey | ZPQOPVIELGIULI-UHFFFAOYSA-N |
| PubChem CID | 10943 |
| ChEMBL | CHEMBL45235 |
| ChEBI | CHEBI:36693 |
| EC No. | 208-792-1 |
| DTXSID | DTXSID6022056 |
| Lokaler Name | 1,3-Dichlorbenzol |
Chemische & physikalische Eigenschaften
| XLogP | 3,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 0 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 0 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 8 |
| Formalladung | 0 |
| Komplexität | 64,9 |
| Stoffklassen | Flammable agents - 2nd degreeVolatile Organic Compound (VOC) (Volatile Organic Compound (VOC)/Semi-Volatile Organic Compound (SVOC)) |
| Solvents | Solvents -> Chlorinated Aromatics |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| Pestizide | Pesticide -> EPA IRIS |
| LogP (Verteilungskoeffizient) | log Kow = 3.533.44 |
| Dichte | 1.2884 at 68 °F (USCG, 1999) - Denser than waterwill sink1.2884 at 20 °C/4 °CRelative density (water = 1): 1.2881.2884 @ 20°C1.288 g/mL at 25 °C (lit.) |
| Viscosity | 1.044 mPa.s at 25 °C |
| Color/Form | Colorless liquid |
| Löslichkeit | less than 1 mg/mL at 70 °F (NTP, 1992)Sol in ethanol, ethervery soluble in acetoneIn water, 125 mg/L at 25 °CSolubility in water: noneDifficult to mix.0.0123 g/100 mL (25 ºC) |
| Flammpunkt | 146 °F (NTP, 1992)63 °C |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Siedepunkt | 343 °F at 760 mmHg (NTP, 1992)173 °C173 °C @760 [mm Hg]172-173 °C (lit.) |
| Schmelzpunkt | -25--22 °C (lit.) |
| Dampfdruck | 5 mm Hg ( 38.8 °C) |
| Brechungsindex | n20/D 1.546(lit.) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless to slightly yellow |
| Geruch | Pleasant odor |
| Merck | 14,3055 |
| BRN | 956618 |
| Henry-Konstante | 2.14 at 20.00 °C (inert gas stripping, Hovorka and Dohnal, 1997) |
| Dielektrizitätskonstante | 5.0 |
| Stabilität | Stability Combustible. Incompatible with strong oxidizing agents, aluminium, aluminium alloys. Moisture-sensitive. |
| InChI | 1S/C6H4Cl2/c7-5-2-1-3-6(8)4-5/h1-4H |
| InChIKey | ZPQOPVIELGIULI-UHFFFAOYSA-N |
| SMILES | Clc1cccc(Cl)c1 |
| LogP (Verteilungskoeffizient) | 3.53 at 22℃ |
| CAS Datenbank | 541-73-1(CAS DataBase Reference) |
| NIST chemische Informationen | Benzene, 1,3-dichloro-(541-73-1) |
| EPA chemische Informationen | m-Dichlorobenzene (541-73-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302: Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P319, P321, P330, P332+P317, P333+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | Chemical: Benzene, 1,3-dichloro-Hazard Traits - Endocrine ToxicityHepatotoxicity and Digestive System ToxicityNephrotoxicity and Other Toxicity to the Urinary SystemStatus: Active Update: 13-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/180761,3-Dichlorobenzene: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| Weitere Sicherheitsinformationen | IMAP assessments - Benzene, 1,3-dichloro-: Human health tier I assessment |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | Special Hazards of Combustion Products: Irritating vapors including hydrogen chloride are produced. (USCG, 1999)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 63 °C explosive vapour/air mixtures may be formed. |
| Brandpotenzial | Combustiblem-Dichlorobenzene is ignitable only with difficulty. |
| Gesundheitsgefahren | INHALATION: Causes headache, drousiness, unsteadiness. Irritating to mucous membranes. EYES: Severe irritation. SKIN: Severe irritation. INGESTION: Irritation of gastric mucosa, nausea, vomiting, diarrhea, abdominal cramps and cyanosis. (USCG, 1999) |
| Gefahrenübersicht | An eye, nose, and throat irritant[HSDB] Severely irritating to eyes and skin |
Anwendungen & Verwendung
Verwenden
1,3-Dichlorobenzene is used in organic synthesis that can synthesize fungicides imazalil, propiconazole, epiconazole, and insecticides insectaphos. It is also used in the synthesis of 1,2-diaminobenzene, in addition, it is also used as a solvent in the fields of dyes, medicine, resin, rubber and so on.
Verwenden
1,3-Dichlorobenzene is used in medicine, and dyes. And it is also used to study the effect of solvent vapor pressure on the vertical nanowire of C60 molecules1. 1,3-Dichlorobenzene, a chlorinated aromatic hydrocarbon, can be detected in environmental samples using an advanced Fourier transform infrared spectroscopy-attenuated total reflectance (FTIR-ATR) sensor.
Herstellung & Synthese
synthetische
1,3-Dichlorobenzene is prepared from o-chloroaniline through diazotization and displacement reaction. Add o-chloroaniline and hydrochloric acid into the reaction pot, mix evenly below 25°C, cool to 0°C, drop in sodium nitrite solution, control the temperature at 0-5°C, stop adding when the potassium iodide starch indicator turns blue, and obtain diazonium salt solution. Then add the diazonium salt solution into the hydrochloric acid solution of cuprous chloride at 0~5℃, stir well, heat up to 60~70℃ and react for 1h, after cooling, let stand for stratification, and use 5% sodium hydroxide for the oil layer. Repeated washing with water, dehydration with anhydrous calcium chloride, fractional distillation, and collection of fractions at 177-183 °C to obtain the product 1,3-dichlorobenzene.