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Methylmagnesiumbromid
MeMgBr · Methyl magnesium bromide(in ethyl ether) · Magnesium, bromomethyl- · METHYLMAGNESIUM BROMIDE SOLUTION · bromomethyl-magnesiu · BROMOMETHYLMAGNESIUM · Methylbromomagnesium · Methylmagnesiumbromid
Identifikatoren & physikalische Daten
| CAS No. | 75-16-1 |
|---|---|
| Summenformel | CH3BrMg |
| Durchschnittliche Molmasse | 119,24 g/mol |
| SMILES | [Br-].[CH3-].[Mg+2] |
| InChIKey | AVFUHBJCUUTGCD-UHFFFAOYSA-M |
| PubChem CID | 6349 |
| EC No. | 200-844-1 |
| DTXSID | DTXSID7052496 |
| Lokaler Name | Methylmagnesiumbromid |
Chemische & physikalische Eigenschaften
| Polarare Oberfläche (TPSA) | 0 |
|---|---|
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 3 |
| Formalladung | 0 |
| Komplexität | 4,8 |
| Stoffklassen | Metals -> Metals, Organic Compounds |
| Löslichkeit | Soluble in ether and tetrahydrofuraninsoluble in hydrocarbonsReacts with water. |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| Physical Description | Methyl magnesium bromide in ethyl ether appears as a colorless cloudy solution in diethyl ether. Vapors heavier than air.Diethyl ether solution: Cloudy colorless liquid[CAMEO] In 1.4m toluene/tetrahydrofuran solution: Orange liquid[MSDSonline] |
| Other Experimental Properties | Moisture sensitive... May react violently with water. /Methyl magnesium bromide in ethyl ether/ |
| Siedepunkt | 78-80℃ |
| Dichte | 1.035 g/mL at 25 °C |
| Flammpunkt | 77 °F |
| Lagerbedingungen | water-free area |
| Aggregatzustand | Solution, may develop some turbidity precipitate |
| Farbe | Pale brown |
| BRN | 3535220 |
| InChI | InChI=1S/CH3.BrH.Mg/h1H3/q+1/p-1 |
| InChIKey | AVFUHBJCUUTGCD-UHFFFAOYSA-M |
| SMILES | [Mg](C)Br |
| CAS Datenbank | 75-16-1(CAS DataBase Reference) |
| EPA chemische Informationen | Magnesium, bromomethyl- (75-16-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH225 (39.7%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P223, P231+P232, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P335+P334, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P402+P404, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 73 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | REACH registered substance: Methylmagnesium bromide (EC: 200-844-1)Magnesium, bromomethyl-: Does not have an individual approval but may be used under an appropriate group standard |
| DOT-Kennzeichnung | Dangerous When Wet Flammable Liquid |
| Brandgefahren | Excerpt from ERG Guide 138 [Substances - Water-Reactive (Emitting Flammable Gases)]: |
| Brandpotenzial | SEE ETHERS. ...ETHERS...ARE...DANGEROUS FIRE HAZARDS. ...EASILY IGNITED & HAVE LOW FLASH POINTS. IT IS NECESSARY TO CONTROL SMOKING, OPEN FLAMES...HOT PLATES...WHERE LOW MOLECULAR WT ETHERS ARE APT TO REACH 1% CONCN OR MORE IN AIR. /ETHERS/FLAMMABLE, DANGEROUS FIRE...RISK |
| Gesundheitsgefahren | Excerpt from ERG Guide 138 [Substances - Water-Reactive (Emitting Flammable Gases)]: |
| Gefahrenübersicht | May have violent reaction with water[HSDB] A strong reducing agent that is highly flammableReacts with water evolving methaneMay form unstable peroxides on contact with air[CAMEO] Apart from their instability in air and their caustic basic properties, organomagnesium compounds and the precipitated inorganic magnesium salts produced during their use display no pronounced toxicity or side effects of environmental concern. [Ullmann] Reacts violently with waterMay form explosive peroxidesA corrosive substance that can cause injury to the skin, eyes, and respiratory tractInhalation may cause chemical pneumonitis and pulmonary edemaInhalation of high concentrations can cause CNS depression[MSDSonline] |
| Reaktive Gruppe | Ethers |
| Reactivity Alerts | Highly Flammable |
| Reactivity Profile | Organometallics, such as METHYL MAGNESIUM BROMIDE, are reactive with many other groups. Incompatible with acids and bases. Organometallics are good reducing agents and therefore incompatible with oxidizing agents. Often reactive with water to generate toxic or flammable gases. |
| DOT Hazard Classification | Methyl magnesium bromide, in ethyl etherUN1928Div 4.3 Dangerous when wet material (49 eCFR § 173.124)PG I: the degree of danger presented by the material is great |
| Air and Water Reactions | Highly flammable. The solution reacts with water or moisture in the air to form flammable methane gas. The heat from this reaction may be sufficient to ignite the produced methane. Unstable peroxides may form with exposure of the ether to air. This is a slow process. |
| Hazard Classes and Categories | Flam. Liq. 2 (39.7%) |
| Brandbekämpfung | Excerpt from ERG Guide 138 [Substances - Water-Reactive (Emitting Flammable Gases)]: |
| Erste Hilfe | Excerpt from ERG Guide 138 [Substances - Water-Reactive (Emitting Flammable Gases)]: |
| Firefighting Hazards | The solution /methyl magnesium bromide in ethyl ether/ reacts with water to give methane, a flammable gas. The heat of this reaction may be sufficient to ignite the methane. /Methyl magnesium bromide in ethyl ether/ |
| Brandbekämpfungsverfahren | If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use "alcohol" foam, dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Do not use water on material itself. /Methyl magnesium bromide in ethyl ether/Evacuation: If fire becomes uncontrollable or container is exposed to direct flame - consider evacuation of one-third (1/3) mile radius. /Methyl magnesium bromide in ethyl ether/ |
| Lagerbedingungen | ...MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMPOSE INTO TOXIC COMPONENTS...SHOULD BE STORED IN A COOL, WELL VENTILATED PLACE, OUT OF THE DIRECT RAYS OF THE SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD, AND SHOULD BE PERIODICALLY INSPECTED. INCOMPATIBLE MATERIALS SHOULD BE ISOLATED... /TOXIC HAZARDS/ |
| Freisetung ohne Brand | Excerpt from ERG Guide 138 [Substances - Water-Reactive (Emitting Flammable Gases)]: |
| Entsorgungsverfahren | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Preventive Measures | If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. Do not use water on material itself. /Methyl magnesium bromide in ethyl ether/Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Methyl magnesium bromide in ethyl ether/If material leaking (not on fire) consider evacuation from downwind area based on amount of material spilled, location and weather conditions. /Methyl magnesium bromide in ethyl ether/ |
| Isolation and Evacuation | Excerpt from ERG Guide 138 [Substances - Water-Reactive (Emitting Flammable Gases)]: |
| Protective Action Criteria (PAC) | 1.2 [mg/m3]13 [mg/m3]79 [mg/m3] |
| Personal Protective Equipment (PPE) | Excerpt from ERG Guide 138 [Substances - Water-Reactive (Emitting Flammable Gases)]:Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles. ... /Methyl magnesium bromide in ethyl ether/ |
| Unerwünschte Wirkungen | Dermatotoxin - Skin burns. |
| F | 1-3-10 |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1928 |
| Zollcode | 29319090 |
| RTECS-Nr. | OM3700000 |
| R-Sätze (R) | 12-14-19-22-34-66-67-52/53-10-65-63-48/20-14/15-11-37 |
| Gefahrensymbole | C,F+,F |
| Sicherheitshinweise (S) | 9-16-26-45-61-36/37/39-62-43-36/37-23 |
| Gefahrenklasse | 4.3Aquatic Chronic 3Eye Dam. 1Flam. Liq. 3Skin Corr. 1BSTOT SE 3Water-react 1 |
| Verpackungsgruppe | I |
| Lagerklasse | 4.3 - Hazardous materials which set free flammable gases upon contact with water |
| Gefahrstoffdaten | 75-16-1(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
Methylmagnesium bromide is widely used in organic synthesis.