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| | Ethylmagnesium bromide Basic information |
| | Ethylmagnesium bromide Chemical Properties |
| Melting point | -116.3°C | | Boiling point | 34.6°C | | density | 1.02 g/mL at 25 °C | | Fp | <−30 °F | | storage temp. | water-free area | | solubility | Miscible in alcohols, ketones, esters, ethers, hydrocarbons. | | form | Solution | | color | Pale yellow to brown | | Water Solubility | Reacts with water. | | Sensitive | Air & Moisture Sensitive | | BRN | 3587203 | | Exposure limits | ACGIH: TWA 400 ppm; STEL 500 ppm
OSHA: TWA 400 ppm(1200 mg/m3)
NIOSH: IDLH 1900 ppm | | InChI | InChI=1S/C2H5.BrH.Mg/c1-2;;/h1H2,2H3;1H;/q;;+1/p-1 | | InChIKey | TWTWFMUQSOFTRN-UHFFFAOYSA-M | | SMILES | C(C)[Mg]Br | | CAS DataBase Reference | 925-90-6(CAS DataBase Reference) | | EPA Substance Registry System | Magnesium, bromoethyl- (925-90-6) |
| Hazard Codes | F+,C,F | | Risk Statements | 12-14/15-19-22-34-66-67-40-11-14-37 | | Safety Statements | 16-26-36/37/39-43-45-7/8-27-9 | | RIDADR | UN 3399 4.3/PG 1 | | WGK Germany | 1 | | RTECS | LU5950000 | | F | 1-3-10 | | TSCA | TSCA listed | | HazardClass | 4.3 | | PackingGroup | I | | HS Code | 29319090 | | Storage Class | 4.3 - Hazardous materials which set free flammable gases upon contact with water | | Hazard Classifications | Acute Tox. 4 Oral
Eye Dam. 1
Flam. Liq. 2
Skin Corr. 1B
STOT SE 3
Water-react 1 |
| | Ethylmagnesium bromide Usage And Synthesis |
| Chemical Properties | Ethylmagnesium bromide is generally sold as a dark brown solution and can be dissolved in diethyl ether, butyl ether, isopropyl ether, THF and anisole. | | Uses | Ethylmagnesium Bromide is a useful reagent in preparation of zirconium complexes having two phenoxy-imine chelate ligands for olefin polymerization. | | Preparation | Ethylmagnesium bromide is commercially available, usually as a solution in diethyl ether or tetrahydrofuran. It may be prepared in the normal manner of Grignard reagents — by reacting bromoethane with magnesium in diethyl ether:
EtBr + Mg → EtMgBr | | Application | Ethylmagnesium bromide is a Grignard reagent widely used in organic chemical synthesis. It can be employed in the following chemical reactions:
(1) The cleavage effect on pentafluorophenylphosphine bonds and sulphur bonds: Reactions between tri(pentafluorophenyl)phosphine and bis(pentafluorophenyl)sulphide with ethylmagnesium bromide yield products indicating the pentafluorophenyl group detaches from both phosphorus and sulphur[1].
(2) Reaction with unsaturated organotin compounds to form saturated compounds: Its reaction with tri-n-butylstannylacetylene in diethyl ether removes ethane, ethylene, acetylene, and ethylacetylene, yielding ethyl tri-n-butylstannyl and bis-1,2-tri-n-butylstannyl ethane[2].
(3) Facilitating selective transformation of cyclopropyl groups: In the case of the tetrahydrofuran-protected racemic diethyl malonate 1, selective conversion of the cyclopropyl group is achieved via a reductive cyclopropanation reaction using ethylmagnesium bromide in the presence of tetrahydrofuran. This ultimately enables the isolation of the ethoxycarbonyl group from diethyl malonate[3]. | | Reactions | Ethylmagnesium bromide reacts with water to produce ethane.
CH3CH2MgBr+H2O→CH3-CH3+Mg(OH)Br
Reaction of ethylmagnesium bromide with ethyl acetate in the presence of styrene and titanium(IV) isopropoxide as a catalyst leads to (Z)-1-methyl-2-phenylcyclopropanol in 42% yield. | | General Description | Ethylmagnesium bromide, an organomagnesium compound, is commonly known as Grignard reagent. It is a powerful carbon nucleophile mainly used for C-C bond formation. Ethylmagnesium bromide solution (3.0 M in diethyl ether) can be used for copper(I)-catalyzed allylic substitution reaction.
Grignard reagents are organometallic compounds discovered by a French chemist, Victor Grignard in 1900. These compounds can be obtained as a formula “RMgX” by the reaction of halogenated hydrocarbons with magnesium metal in anhydrous solvents such as diethyl ether,1) and have been widely used in organic synthesis. | | Hazard | Flammable, dangerous fire risk. | | reaction suitability | reaction type: Grignard Reaction | | References | [1] STEPHEN A. SICREE Christ T. Cleavage of pentafluorophenyl-phosphorus and -sulfur bonds by ethylmagnesium bromide[J]. Journal of Fluorine Chemistry, 1992, 59 2: Pages 269-273. https://doi.org/10.1016/S0022-1139(00)82419-7.
[2] A. N. NESMEYANOV I. S S A E BORISOV. ChemInform Abstract: REACTIONS OF ETHYLMAGNESIUM BROMIDE WITH SOME UNSATURATED ORGANOTIN COMPOUNDS[J]. ChemInform, 1976, 7 4. https://doi.org/10.1002/chin.197604258.
[3] ANDREI V. BEKISH Oleg G K. Differentiation between the ethoxycarbonyl groups in diethyl malate via their titanium-catalyzed reductive cyclopropanation with ethylmagnesium bromide and subsequent site-selective three-carbon ring cleavage[J]. Tetrahedron Letters, 2005, 46 41: Pages 6975-6978. https://doi.org/10.1016/j.tetlet.2005.08.076. |
| | Ethylmagnesium bromide Preparation Products And Raw materials |
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