3-Bromtoluol
1-BROMO-3-METHYLBENZENE · META-BROMOTOLUENE · 3-Methylbromobenzene · 3-BromotoL · 3-Bromtoluol · 3-Bromotolune · 3-bromo-toluen · 5-Bromotoluene
Identifikatoren & physikalische Daten
| CAS No. | 591-17-3 |
|---|---|
| Summenformel | C7H7Br |
| Durchschnittliche Molmasse | 171,03 g/mol |
| Monoisotopische Masse | 169,97311232 g/mol |
| SMILES | Cc1cccc(Br)c1 |
| InChIKey | WJIFKOVZNJTSGO-UHFFFAOYSA-N |
| PubChem CID | 11560 |
| ChEMBL | CHEMBL1538200 |
| EC No. | 209-702-3 |
| DTXSID | DTXSID3024659 |
| Lokaler Name | 3-Bromtoluol |
Chemische & physikalische Eigenschaften
| XLogP | 3,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 0 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 0 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 8 |
| Formalladung | 0 |
| Komplexität | 70,8 |
| Solvents | Solvents -> Brominated Solvents |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| LogP (Verteilungskoeffizient) | log Kow = 3.41 |
| Dichte | 1.41 at 68 °F (NTP, 1992) - Denser than waterwill sink1.4099 at 20 °C/4 °C1.41 g/mL at 25 °C(lit.) |
| Color/Form | LIQUID |
| Löslichkeit | less than 1 mg/mL at 68 °F (NTP, 1992)Sol in chloroformSoluble in ethanol and acetone, miscible in etherWater solubility = 51.3 mg/l0.05g/linsoluble |
| Flammpunkt | 140 °F (NTP, 1992)60 °C |
| Siedepunkt | 362.7 °F at 760 mmHg (NTP, 1992)183.7 °C at 760 mm Hg183.7 °C(lit.) |
| Schmelzpunkt | -40 °F (NTP, 1992)-39.8 °C-40 °C |
| Dampfdruck | 1 mmHg at 58.6 °F (NTP, 1992)1.53 [mmHg]Vapor pressure = 0.145 kPa (1.09 mm Hg) at 25 °C2.04 hPa ( 25 °C) |
| Brechungsindex | Index of refraction: 1.5510 at 20 °C/Dn20/D 1.552(lit.) |
| Heat of Vaporization | 10,537.1 gcal/gmole |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Liquid |
| Wichte | 1.410 |
| Farbe | Clear colorless to light yellow |
| Merck | 14,1439 |
| BRN | 1903633 |
| Henry-Konstante | 1.5×10-3 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Dielektrizitätskonstante | 5.3600000000000003 |
| InChI | 1S/C7H7Br/c1-6-3-2-4-7(8)5-6/h2-5H,1H3 |
| InChIKey | WJIFKOVZNJTSGO-UHFFFAOYSA-N |
| SMILES | Cc1cccc(Br)c1 |
| CAS Datenbank | 591-17-3(CAS DataBase Reference) |
| NIST chemische Informationen | Benzene, 1-bromo-3-methyl-(591-17-3) |
| EPA chemische Informationen | m-Bromotoluene (591-17-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH226 (84%): Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 50 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Benzene, 1-bromo-3-methyl-3-Bromotoluene: Does not have an individual approval but may be used under an appropriate group standard |
| DOT-Kennzeichnung | Flammable Liquid Poison |
| Brandgefahren | This chemical is combustible. (NTP, 1992) |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to this compound include eye and skin irritation. |
| Gefahrenübersicht | Irritant[HSDB] An irritantInhalation of high concentrations can cause CNS depression[MSDSonline]The major hazards encountered in the use and handling of 3-bromotoluene stem from its toxicologic properties. Exposure to 3-bromotoluene may occur through inhalation or dermal contact at sites where the substance is manufactured, used as a solvent, or used as a chemical intermediate. This substance has the potential to cause respiratory irritation and CNS depression. Entry into contaminated areas warrants the wearing of a full-face mask, self-contained breathing apparatus which provides eye protection. This substance is normally stable, even under fire conditionsrequiring moderate heating before ignition will occur. Normal procedures may be used to fight a 3-bromotoluene fireusing water to blanket the fire. Before transporting 3-bromotoluene, the regulatory requirements of the DOT must be consulted. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance. |
| Reaktive Gruppe | Aryl Halides |
| Reactivity Alerts |
Anwendungen & Verwendung
Verwenden
3-Bromotoluene was used in the precise determination of bromine isotope ratio in organic compounds by MC-ICPMS ( Multicollector-Inductively Coupled Plasma Mass Spectrometer). It undergoes palladium-catalyzed cyanation reaction in the presence of K4[Fe(CN)6] as the cyanide surrogate. It also undergoes palladium-catalyzed reaction with alkynyltriarylborates to yield trisubstituted alkenylboranes.
Herstellung & Synthese
synthetische
Synthesis of 3-Bromotoluene: It is derived from 3-bromo-4-aminotoluene by diazotization and reduction. The mixture of 95% ethanol, concentrated sulfuric acid and 3-bromo-4-aminotoluene was stirred and cooled to 10°C, and sodium nitrite solution was added to keep the reaction temperature not exceeding 10°C. After adding, continue stirring for 20min. Add the copper powder washed with ether, heat carefully, stop heating after the reaction starts, nitrogen will be released violently, and acetaldehyde will be formed. Then steam distillation is carried out until no oily substance evaporates. Separate the organic phase from the distillate and wash with 10% sodium hydroxide, water, concentrated sulfuric acid, and 5% sodium carbonate solution in sequence. Dry with anhydrous calcium chloride, filter, distill, collect 180-183 ℃ (99.75kPa) fractions to obtain colorless pure 3-bromotoluene with a yield of over 50%.