Conditions | Yield |
---|---|
With magnesium In tetrahydrofuran at 40℃; for 0.25h; Inert atmosphere; Flow reactor; | 100% |
With magnesium In tetrahydrofuran | |
With magnesium In diethyl ether at 19.9℃; Rate constant; various concentrations of aryl halide; |
2-amino-5-chlorobenzonitrile
A
(2-amino-5-chlorophenyl)-phenyl-methane-imine
B
phenylmagnesium bromide
Conditions | Yield |
---|---|
A 92% B n/a |
Conditions | Yield |
---|---|
With magnesium In tetrahydrofuran | A 24% B n/a |
Conditions | Yield |
---|---|
In tetrahydrofuran; toluene |
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether |
Conditions | Yield |
---|---|
In tetrahydrofuran |
Conditions | Yield |
---|---|
With ammonium chloride |
Conditions | Yield |
---|---|
With biphenyl; ethylmagnesium bromide; phenylmagnesium bromide In o-xylene |
Conditions | Yield |
---|---|
With hydrogenchloride; iodine In magnesium |
Conditions | Yield |
---|---|
With magnesium |
bromobenzene
1-methyl-3-fluoro-5,7-dichloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one
B
phenylmagnesium bromide
Conditions | Yield |
---|---|
With HF In tetrahydrofuran |
Conditions | Yield |
---|---|
With magnesium In diethyl ether | A 17 g (34%) B n/a |
Conditions | Yield |
---|---|
In tetrahydrofuran | |
In tetrahydrofuran for 1.5h; Inert atmosphere; Reflux; | |
With iodine In tetrahydrofuran for 2h; Inert atmosphere; Reflux; | |
With iodine In tetrahydrofuran for 1h; Grignard Reaction; Heating / reflux; |
Conditions | Yield |
---|---|
With diethyl ether |
Conditions | Yield |
---|---|
With diethyl ether untersucht wurde die Geschwindigkeit; |
Conditions | Yield |
---|---|
With 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone at -20℃; Product distribution / selectivity; | 100% |
With iron(III) chloride; 1,2-dichloro-ethane In tetrahydrofuran at 0℃; for 0.0833333h; Ionic liquid; Inert atmosphere; | 100% |
With 1,2-bisperfluorotolyl-3,3,4,4,5,5-hexafluorocyclopentene In tetrahydrofuran at 25℃; for 1h; Reagent/catalyst; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
nickel(II) In tetrahydrofuran for 18h; Product distribution; other catalyst, other solvents; other Grignard compounds and alkyl or vinyl halides; | 100% |
With CpNi[1-(ethoxycarbonyl)methyl-3-(3,5-dimethylbenzyl)benzimidazolin-2-ylidene]Br In tetrahydrofuran at 25℃; for 3h; Kumada Cross-Coupling; Inert atmosphere; Schlenk technique; | 97% |
With Pd/Al(OH)3 In toluene at 140℃; for 36h; Kumada Cross-Coupling; Inert atmosphere; | 94% |
phenylmagnesium bromide
Conditions | Yield |
---|---|
In diethyl ether for 4h; Ambient temperature; | 100% |
phenylmagnesium bromide
Conditions | Yield |
---|---|
In diethyl ether for 4h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran at 0℃; | 100% |
Stage #1: benzoyl chloride With 1-methyl-pyrrolidin-2-one In toluene at 0℃; for 0.5h; Stage #2: phenylmagnesium bromide In tetrahydrofuran; toluene at -10 - 0℃; for 4.25h; chemoselective reaction; | 89% |
In 2-methyltetrahydrofuran at 25℃; for 1h; Solvent; Concentration; Flow reactor; Green chemistry; | 85% |
3-phenylbutanoyl chloride
phenylmagnesium bromide
1,3-diphenylbutane-1-one
Conditions | Yield |
---|---|
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran at 0℃; | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran | 100% |
methyl 3,3-dimethylglutarate
phenylmagnesium bromide
3,3-dimethy-5,5-diphenyl-5-hydroxypentanoic acid lactone
Conditions | Yield |
---|---|
In tetrahydrofuran 2 h; reflux, 2,5 h; | 100% |
phenylmagnesium bromide
methyl (S)-N-(tert-butoxycarbonyl)indoline-2-carboxylate
(S)-tert-butyl 2-(hydroxydiphenylmethyl)indoline-1-carboxylate
Conditions | Yield |
---|---|
In diethyl ether at 0℃; Inert atmosphere; Reflux; | 100% |
In tetrahydrofuran; diethyl ether at 0 - 20℃; for 7h; | 25% |
In diethyl ether at 0℃; |
phenylmagnesium bromide
(4-Methoxy-phenyl)-(4-phenyl-phthalazin-1-yl)-methanone
(4-Methoxy-phenyl)-phenyl-(4-phenyl-phthalazin-1-yl)-methanol
Conditions | Yield |
---|---|
In tetrahydrofuran for 1h; Ambient temperature; | 100% |
phenylmagnesium bromide
(2R,9S)-2,9-diphenyl-1-aza-4-oxabicyclo[4.3.0]nonane
(2S,6R,1'R)-N-2'-hydroxy-1'-phenylethyl-2,6-diphenylpiperidine
Conditions | Yield |
---|---|
In tetrahydrofuran at 0℃; for 72h; | 100% |
Conditions | Yield |
---|---|
With [1,3-bis(2,6-diisopropylphenyl)-imidazolium][Ni(PPh3)Cl3] In tetrahydrofuran at 30℃; for 1h; Kumada Cross-Coupling; Schlenk technique; Inert atmosphere; | 100% |
With C70H40Cl2F68N2O6Pd2 In tetrahydrofuran at 100℃; for 0.0166667h; Kumada coupling reaction; Microwave irradiation; | 96% |
With C17H36ClN6NiP2(1+)*Cl(1-) In tetrahydrofuran for 6h; Reagent/catalyst; Kumada Cross-Coupling; Inert atmosphere; | 96% |
3-(3-bromophenyl)-N-methoxy-N-methylpropanamide
phenylmagnesium bromide
3-(3-bromophenyl)-1-phenyl-propan-1-one
Conditions | Yield |
---|---|
In tetrahydrofuran at -78 - 0℃; for 2h; | 100% |
(R)-tert-butyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate
phenylmagnesium bromide
(R)-tert-butyl 3-benzoylpiperidine-1-carboxylate
Conditions | Yield |
---|---|
Stage #1: (R)-tert-butyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate; phenylmagnesium bromide In tetrahydrofuran at -10 - 20℃; for 1.25h; Stage #2: With hydrogenchloride In tetrahydrofuran; water for 0.333333h; Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water | 100% |
Stage #1: (R)-tert-butyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate; phenylmagnesium bromide In tetrahydrofuran at -10 - 20℃; for 1.25h; Stage #2: With hydrogenchloride; water In tetrahydrofuran for 0.333333h; | 100% |
Stage #1: (R)-tert-butyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate; phenylmagnesium bromide In tetrahydrofuran at -10 - 20℃; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water |
Conditions | Yield |
---|---|
Stage #1: 3-cyanobromobenzene; phenylmagnesium bromide In tetrahydrofuran at 20 - 60℃; for 4h; Stage #2: With methanol In tetrahydrofuran at 0℃; | 100% |
Stage #1: 3-cyanobromobenzene; phenylmagnesium bromide In tetrahydrofuran at 20 - 60℃; for 4h; Stage #2: With methanol In tetrahydrofuran at 0℃; |
Conditions | Yield |
---|---|
With hydrogenchloride; ammonium chloride In tetrahydrofuran | 100% |
Stage #1: 4-butanolide; phenylmagnesium bromide In tetrahydrofuran; diethyl ether at -78 - 20℃; Inert atmosphere; Stage #2: With water; ammonium chloride In tetrahydrofuran; diethyl ether at 10℃; Cooling with ice; | |
In tetrahydrofuran Grignard reaction; Reflux; |
3-Ethoxycyclohex-2-en-1-one
phenylmagnesium bromide
3-phenylcyclohex-2-enone
Conditions | Yield |
---|---|
Stage #1: 3-Ethoxycyclohex-2-en-1-one; phenylmagnesium bromide In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: With hydrogenchloride; water In tetrahydrofuran | 100% |
Stage #1: 3-Ethoxycyclohex-2-en-1-one; phenylmagnesium bromide In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: With hydrogenchloride; water In tetrahydrofuran | 100% |
Stage #1: 3-Ethoxycyclohex-2-en-1-one; phenylmagnesium bromide In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; | 100% |
Conditions | Yield |
---|---|
Stage #1: 2-fluoropyridine; phenylmagnesium bromide; bis(acetylacetonate)nickel(II); ((2-hydroxymethyl)phenyl)diphenylphosphine In diethyl ether for 0.5h; Stage #2: With methanol In diethyl ether Product distribution / selectivity; | 100% |
Stage #1: 2-fluoropyridine; phenylmagnesium bromide; 1-[2-(diphenylphosphino)phenyl]ethanol; bis(acetylacetonate)nickel(II) In diethyl ether for 2h; Stage #2: With methanol In diethyl ether Product distribution / selectivity; | 96% |
2-bromo-3,5-bis(methoxymethoxy)-6-phenylbenzaldehyde
phenylmagnesium bromide
1-[2-bromo-3,5-bis(methoxymethoxy)-6-phenylphenyl]-1-phenylmethanol
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether at 0℃; for 2h; | 100% |
N-(2-Diethylaminoethyl)-4'-(1-oxo-2-phenylbutyl)methanesulfonanilide
phenylmagnesium bromide
N-(2-Diethylaminoethyl)-4'-(1-hydroxy-1,2-diphenylbutyl)methanesulfonanilide
Conditions | Yield |
---|---|
With hydrogenchloride; ammonium chloride In diethyl ether; water | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 5h; | 100% |
Conditions | Yield |
---|---|
In diethyl ether; toluene Ar-atmosphere; stirring (1 h); filtering, evapn. (vac.), extg. (CH2Cl2), filtering, evapn., washing (pentane); | 100% |
In tetrahydrofuran |
phenylmagnesium bromide
(Z)-3-Trimethylstannanyl-hept-2-enal
1-phenyl-3-trimethylstannyl-hept-2-ene-1-al
Conditions | Yield |
---|---|
In diethyl ether Ar-atmosphere; slight excess PhMgBr, refluxing for 12 h; addn. of satd. aq. NH4Cl, extn. of aq. layer (Et2O), drying (MgSO4), solvent removal; isomer mixt. not sepd., detd. by (119)Sn-NMR spectroscopy; | 100% |
1-(4-fluorophenyl)-1H-indazole-5-carbaldehyde
phenylmagnesium bromide
(1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methanol
Conditions | Yield |
---|---|
Stage #1: 1-(4-fluorophenyl)-1H-indazol-5-carboxaldehyde; phenylmagnesium bromide In tetrahydrofuran at 0℃; for 1h; Stage #2: With water; ammonium chloride In tetrahydrofuran | 100% |
Stage #1: 1-(4-fluorophenyl)-1H-indazol-5-carboxaldehyde; phenylmagnesium bromide In tetrahydrofuran at 0℃; for 1h; Stage #2: With water; ammonium chloride In tetrahydrofuran | 100% |
5-formyl-N,N-dimethyl-1H-indole-1-carboxamide
phenylmagnesium bromide
5-(hydroxy(phenyl)methyl)-N,N-dimethyl-1H-indole-1-carboxamide
Conditions | Yield |
---|---|
Stage #1: 5-formyl-N,N-dimethyl-1H-indole-1-carboxamide; phenylmagnesium bromide In tetrahydrofuran; diethyl ether at -78 - 20℃; for 2h; Stage #2: With water; ammonium chloride In tetrahydrofuran; diethyl ether | 100% |
In tetrahydrofuran | 100% |
trifluoromethanesulfonic acid 1-bromonaphthalen-2-yl ester
phenylmagnesium bromide
1-bromo-2-phenylnaphthalene
Conditions | Yield |
---|---|
Stage #1: trifluoromethanesulfonic acid 1-bromonaphthalen-2-yl ester With 1,3-bis-(diphenylphosphino)propane; lithium bromide; tris-(dibenzylideneacetone)dipalladium(0) In diethyl ether at 20℃; for 0.0833333h; Stage #2: phenylmagnesium bromide In diethyl ether at 0 - 20℃; for 7h; | 100% |
With dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II); lithium bromide In diethyl ether at 0℃; for 18h; Inert atmosphere; | |
With bis(diphenylphosphino)propanepalladium(II) dichloride; lithium bromide In diethyl ether for 1h; Inert atmosphere; Cooling with ice; | 17 g |
(3E,4aR,10aR)-3-benzylidene-4a-ethyl-7-hydroxy-3,4,4a,9,10,10a-hexahydro-1H-phenanthren-2-one
phenylmagnesium bromide
(2S,3E,4aR,10aR)-3-benzylidene-4a-ethyl-2-phenyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-2,7-diol
Conditions | Yield |
---|---|
Stage #1: phenylmagnesium bromide With cerium(III) chloride In tetrahydrofuran at -78℃; for 1.5h; Stage #2: (3E,4aR,10aR)-3-benzylidene-4a-ethyl-7-hydroxy-3,4,4a,9,10,10a-hexahydro-1H-phenanthren-2-one In tetrahydrofuran at -40℃; for 2h; Stage #3: With water; acetic acid In tetrahydrofuran | 100% |
Stage #1: phenylmagnesium bromide With cerium(III) chloride In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere; Stage #2: (3E,4aR,10aR)-3-benzylidene-4a-ethyl-7-hydroxy-3,4,4a,9,10,10a-hexahydro-1H-phenanthren-2-one In tetrahydrofuran at -70 - -40℃; for 2.5h; Inert atmosphere; | 96% |
phenylmagnesium bromide
(2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide
(2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-1-hydroxy-5-phenylpyrrolidine
Conditions | Yield |
---|---|
In tetrahydrofuran at 0℃; for 3h; | 100% |
3,6-di(piperidin-1-yl)-9H-xanthen-9-one
phenylmagnesium bromide
C29H31N2O(1+)*Cl(1-)
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; | 100% |
Molecular Formula: C6H5BrMg
Molecular Weight: 181.31
EINECS: 202-867-2
Flash point: -11 ºC
Water solubility: reacts
Density: 1.134 g/mL at 25 °C
Storage temp: water-free area
Sensitive: Air & Moisture Sensitive
IUPAC Name: magnesium benzene bromide
Appearance: Clear light brown to brown solution when properly
Synonyms: Phenylmagnesium bromide ; Phenyl magnesium bromide(in ethyl ether) ; Bromophenyl-magnesiu ; Phenylmagnesiumbromidesolution ; Bromophenylmagnesium ; Phenylmagnesium bromide, 3.0m solution i n diethyl ether ; Phenylmagnesium bromide solution, ~1 m i n thf ; Phenylmagnesium bromide sol., ~3 m in di ethyl ether
Following is the molecular structure of Phenyl magnesium bromide (100-58-3):
Preparation of Phenyl magnesium bromide (100-58-3):
Phenylmagnesium bromide is commercially available as solutions of diethyl ether or THF. It may be prepared in the laboratory by treating bromobenzene with magnesium metal, usually in the form of ribbon. A small amount of iodine may be used to activate the magnesium to initiate the reaction.
Polar solvents, such as ether or THF, are required to solvate (complex) the magnesium(II) center. The solvent must be aprotic since alcohols and water react with phenylmagnesium bromide to give benzene. Carbonyl-containing solvents such as acetone and ethyl acetate are incompatible with the reagent.
Reacts with chlorine to form an explosive product. When heated to decomposition it emits toxic fumes of Br−.
Safety Information of Phenyl magnesium bromide (100-58-3):
Hazard Codes: F+,C,F
F: Highly Flammable F+: Extremely Flammable C: Corrosive
Risk Statements: 12-14-22-34-19-11
12: Extremely Flammable
14: Reacts violently with water
22: Harmful if swallowed
34: Causes burns
19: May form explosive peroxides
11: Highly Flammable
Safety Statements: 16-26-36/37/39-45-33-29-7/8-6A-43B
16: Keep away from sources of ignition - No smoking
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 36/37/39: Wear suitable protective clothing, gloves and eye/face protection
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
33: Take precautionary measures against static discharges
29: Do not empty into drains
7/8: Keep container tightly closed and dry
6: Keep under ... (inert gas to be specified by the manufacturer)
43: In case of fire, use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add - Never use water)
RIDADR: UN 3399 4.3/PG 1
WGK Germany: 1
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