Conditions | Yield |
---|---|
With magnesium In tetrahydrofuran; diethyl ether at 0℃; | |
With iodine; magnesium In tetrahydrofuran for 0.5h; Ambient temperature; | |
With magnesium In tetrahydrofuran |
Conditions | Yield |
---|---|
In tetrahydrofuran |
4-methyl-pent-3-en-2-one
vinyl magnesium bromide
3,5-dimethyl-hexa-1,4-dien-3-ol
Conditions | Yield |
---|---|
In tetrahydrofuran | 100% |
vinyl magnesium bromide
4-methoxy-benzaldehyde
1-(4-methoxylphenyl)-2-propen-1-ol
Conditions | Yield |
---|---|
In tetrahydrofuran; hexane at 0℃; for 2h; Inert atmosphere; | 100% |
In tetrahydrofuran at 0℃; for 4h; | 96% |
In tetrahydrofuran; diethyl ether at 0 - 20℃; | 95% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; | 100% |
In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | 98% |
In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | 92% |
Benzyloxymethyl-oxiran
vinyl magnesium bromide
1-(benzyloxy)-4-penten-2-ol
Conditions | Yield |
---|---|
With copper(l) iodide In tetrahydrofuran at -20℃; for 0.333333h; | 100% |
With copper(l) iodide In tetrahydrofuran at -78 - -40℃; | 95% |
With copper(l) iodide In tetrahydrofuran | 93% |
chloro-trimethyl-silane
vinyl magnesium bromide
(E)-3-Methoxy-2-(4-oxo-cyclopent-2-enyl)-acrylic acid methyl ester
(E)-3-Methoxy-2-((1R,2S)-4-trimethylsilanyloxy-2-vinyl-cyclopent-3-enyl)-acrylic acid methyl ester
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; chloro-trimethyl-silane; copper(l) iodide In tetrahydrofuran 1.) -75 deg C, 10 h; 2.) -75 deg C to -40 deg C; | 100% |
With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; copper(l) iodide In tetrahydrofuran at -78℃; | 0.62 g |
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether at 0 - 20℃; Inert atmosphere; | 100% |
85% | |
In tetrahydrofuran for 1h; | 82% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; Grignard reaction; | 100% |
Stage #1: hept-6-enal; vinyl magnesium bromide In tetrahydrofuran; diethyl ether at -78 - 20℃; Stage #2: With water; ammonium chloride In tetrahydrofuran; diethyl ether at 20℃; | 90% |
In tetrahydrofuran; diethyl ether for 3h; Ambient temperature; Yield given; | |
In tetrahydrofuran |
Conditions | Yield |
---|---|
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran for 0.0833333h; | 100% |
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran for 5h; further catalysts; | 73% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; zinc(II) chloride 1.) THF, RT, 20 min, 2.) RT, 1 h; Yield given. Multistep reaction; |
(-)-Verbenone
vinyl magnesium bromide
(1S,4R,5R)-4,6,6-trimethyl-4-vinylbicyclo[3.1.1]heptan-2-one
Conditions | Yield |
---|---|
With copper(l) iodide In tetrahydrofuran at -78℃; for 3h; | 100% |
With copper(l) iodide In tetrahydrofuran -50 deg C to room temp., 2 h; | 85% |
With copper(l) iodide In tetrahydrofuran Yield given; |
(E)-β-ionone
vinyl magnesium bromide
(1E)-1-(2,6,6-trimethylcyclohex-1-enyl)-3-methyl-1,4-pentadien-3-ol
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 20h; | 100% |
In tetrahydrofuran for 14h; Ambient temperature; | 94% |
5-methoxy-2-nitro-benzaldehyde
vinyl magnesium bromide
1-(5-Methoxy-2-nitro-phenyl)-prop-2-en-1-ol
Conditions | Yield |
---|---|
In tetrahydrofuran for 3.5h; | 100% |
In tetrahydrofuran at -70℃; | |
In tetrahydrofuran at -70℃; for 3.5h; | |
In tetrahydrofuran at -10 - 20℃; Inert atmosphere; |
2-amino-4'-methylbenzophenone
vinyl magnesium bromide
1-(2'-aminophenyl)-1-(4''-methylphenyl)prop-2-en-1-ol
Conditions | Yield |
---|---|
In tetrahydrofuran at 60℃; for 2h; | 100% |
benzyloxyacetoaldehyde
vinyl magnesium bromide
1-(benzyloxy)but-3-en-2-ol
Conditions | Yield |
---|---|
In tetrahydrofuran for 0.5h; Heating; | 100% |
In tetrahydrofuran at -78 - 20℃; Inert atmosphere; | 91% |
In tetrahydrofuran at 0℃; for 0.166667h; | 88% |
3-phenylpropionyltrimethylsilane
vinyl magnesium bromide
5-phenyl-3-(trimethylsilyl)-1-penten-3-ol
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether at 0℃; for 0.5h; | 100% |
Stage #1: vinyl magnesium bromide With cerium(III) chloride In tetrahydrofuran at -78℃; for 2h; Metallation; Stage #2: 3-phenylpropionyltrimethylsilane In tetrahydrofuran at -78℃; for 2h; Addition; | 98% |
3-isobutoxy-2-methyl-2-cyclohexen-1-one
vinyl magnesium bromide
2-methyl-3-vinyl-cyclohex-2-enone
Conditions | Yield |
---|---|
In tetrahydrofuran at 0℃; for 3h; | 100% |
In tetrahydrofuran at -78 - 20℃; | 49% |
4-(2',2'-Dimethyl-6'-methylidenecyclohexyl)butan-2-one
vinyl magnesium bromide
5-(6',6'-dimethyl-2'-methylenecyclohexyl)-3-hydroxy-3-methyl-pent-1-ene
Conditions | Yield |
---|---|
100% | |
In tetrahydrofuran 1.) room temp. 2 h 2.) overnight 3.) 3 hr reflux; | 75% |
In tetrahydrofuran for 3h; Heating; | 123 mg |
In tetrahydrofuran |
vinyl magnesium bromide
5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose
(4R,5S)-(+)-1-[4-[2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl]-2,2-dimethyl-1,3-dioxolan-5-yl]-(S)-propen-1-ol
Conditions | Yield |
---|---|
In tetrahydrofuran at -78 - 20℃; for 1h; | 100% |
In tetrahydrofuran at -78 - 20℃; for 1h; Grignard reaction; | 96% |
In tetrahydrofuran for 24h; Ambient temperature; | 79% |
vinyl magnesium bromide
9-Butoxy-bicyclo[3.2.2]non-6-en-2-one
9-Butoxy-2-vinyl-bicyclo[3.2.2]non-6-en-2-ol
Conditions | Yield |
---|---|
at 0℃; | 100% |
vinyl magnesium bromide
9-Butylsulfanyl-bicyclo[3.2.2]non-6-en-2-one
9-Butylsulfanyl-2-vinyl-bicyclo[3.2.2]non-6-en-2-ol
Conditions | Yield |
---|---|
at 0℃; | 100% |
vinyl magnesium bromide
9-Phenylsulfanyl-bicyclo[3.2.2]non-6-en-2-one
9-Phenylsulfanyl-2-vinyl-bicyclo[3.2.2]non-6-en-2-ol
Conditions | Yield |
---|---|
at 0℃; | 100% |
vinyl magnesium bromide
3β-t-butyldimethylsilyloxy-pregn-5-en-20-one
(20R,S)-20-vinylpregn-5-ene-3β,20-diol 3β-tert-butyldimethylsilyl ether
Conditions | Yield |
---|---|
100% |
vinyl magnesium bromide
syn-4-(tert-butyldimethylsilyloxy)cyclopentene oxide
(1RS,2SR,4RS)-4-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2-ethenylcyclopentanol
Conditions | Yield |
---|---|
Stage #1: vinyl magnesium bromide; syn-4-(tert-butyldimethylsilyloxy)cyclopentene oxide; copper(l) iodide In tetrahydrofuran at -30 - 0℃; for 2.75h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran | 100% |
copper(l) iodide In tetrahydrofuran -30 gradC for 15 min then 0 gradC for 2 h.; | 79% |
vinyl magnesium bromide
(3R,6S)-3,6-Dimethyl-1-oxo-3,6-dihydro-1H-1λ4-[1,2]thiazine-2-carboxylic acid benzyl ester
C16H21NO3S
Conditions | Yield |
---|---|
In tetrahydrofuran at -60℃; for 0.5h; | 100% |
vinyl magnesium bromide
benzyl 5-formyl-8-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate
5-(1-Hydroxy-allyl)-8-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid benzyl ester
Conditions | Yield |
---|---|
In tetrahydrofuran 1.) 0 deg C, 1 h, 2.) RT, 1 h; | 100% |
vinyl magnesium bromide
12c-ethenyl-4,8,12-trioxatricornan
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | 100% |
In tetrahydrofuran for 7h; | 68% |
vinyl magnesium bromide
Conditions | Yield |
---|---|
With copper(l) iodide; dimethylsulfide In tetrahydrofuran at -15℃; | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 23℃; for 18h; Inert atmosphere; | 100% |
In tetrahydrofuran; diethyl ether at -5 - 20℃; | 86% |
In tetrahydrofuran at -78℃; Grignard reaction; | 66% |
vinyl magnesium bromide
(3R)-3-hydroxy-β-ionone
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 20h; | 100% |
In tetrahydrofuran; toluene at -20℃; for 1.5h; Inert atmosphere; |
vinyl magnesium bromide
(R)-benzyl glycidol
(R)-1-benzyloxypent-4-en-2-ol
Conditions | Yield |
---|---|
Stage #1: (R)-benzyl glycidol With copper(l) iodide In tetrahydrofuran at -78℃; for 0.0833333h; Stage #2: vinyl magnesium bromide In tetrahydrofuran at 20 - 70℃; for 2h; | 100% |
Stage #1: (R)-benzyl glycidol With copper(l) iodide In tetrahydrofuran at 20℃; for 0.0833333h; Stage #2: vinyl magnesium bromide In tetrahydrofuran at -78 - 20℃; for 2h; | 100% |
Stage #1: (R)-benzyl glycidol With copper(l) iodide In tetrahydrofuran at -78 - 20℃; for 0.0833333h; Stage #2: vinyl magnesium bromide In tetrahydrofuran at -70 - 20℃; for 2h; | 100% |
vinyl magnesium bromide
Conditions | Yield |
---|---|
In tetrahydrofuran at -78℃; for 1h; | 100% |
IUPAC Name: Magnesium ethene bromide
Synonyms of Magnesium,bromoethenyl- (CAS NO.1826-67-1): Vinylmagnesium bromide ; Bromovinylmagnesium
Molecular Structure:
Molecular Formula: C2H3BrMg
Molecular Weight: 131.25
CAS NO: 1826-67-1
EINECS: 217-375-3
H bond acceptors: 0
H bond donors: 0
Freely Rotating Bonds: 1
Polar Surface Area: 0 Å2
Density: 0.981 g/mL at 25 °C
Flash Point: 1 °F
Storage temp: Refrigerator
Solubility: vigorous reaction
Water Solubility: vigorous reaction
Appearance: Clear light brown to brown solution
SMILES: Br[Mg]\C=C
InChI: InChI=1/C2H3.BrH.Mg/c1-2;;/h1H,2H2;1H;/q;;+1/p-1/rC2H3BrMg/c1-2-4-3/h2H,1H2
InChIKey: XHHHAXOHMKAOSL-ZAPIYNQUAR
Std. InChI: InChI=1S/C2H3.BrH.Mg/c1-2;;/h1H,2H2;1H;/q;;+1/p-1
Std. InChIKey: XHHHAXOHMKAOSL-UHFFFAOYSA-M
Product Categories of Magnesium,bromoethenyl- (CAS NO.1826-67-1): GRIGNARD REAGENTS;Classes of Metal Compounds;Grignard Reagents & Alkyl Metals;Mg (Magnesium) Compounds;Synthetic Organic Chemistry;Typical Metal Compounds;Alkenyl;Grignard Reagents;Organometallic Reagents
Safety Information of Magnesium,bromoethenyl- (CAS NO.1826-67-1):
Hazard Codes: F,C
Risk Statements: 11-19-34-14/15
R11: Highly flammable.
R14/15: Reacts violently with water, liberating extremely flammable gases
R19: May form explosive peroxides.
R34: Causes burns.
Safety Statements: 16-26-29-33-36/37/39-45-6-43
S16: Keep away from sources of ignition.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S29: Do not empty into drains.
S33: Take precautionary measures against static discharges.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S6: Keep under ... (inert gas to be specified by the manufacturer)
S43: In case of fire use ... (there follows the type of fire-fighting equipment to be used.)
RIDADR: UN3399 4.3/PG 2
WGK Germany: 1
F:1-3-10
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Will burn if involved in a fire. Water Reactive. Material will react with water and may release a flammable and/or toxic gas. Flammable liquid and vapor. May form explosive peroxides.
Extinguishing Media: Use approved class D extinguishing agents or smother with dry sand, clay, or sodium bicarbonate. DO Handling: Do not allow water to get into the container because of violent reaction. Use spark-proof tools and explosion proof equipment. Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Do not allow contact with water. Use only in a chemical fume hood.
Storage: Keep away from sources of ignition. Do not store in direct sunlight. Store in a tightly closed container. Store in a dry area. Flammables-area. Corrosives area. Water free area. Store under nitrogen. Store at room temperature.
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