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Organic metal bromide salts

Organic compound that contains one or more bromide ions as well as an additional metal atom bonded by ionic bonds. Salts are products of acid-base reactions.
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Keyword Search:
1 – 15 of 32 results
1

3-Methoxyphenylmagnesium bromide, 1.0 M in 2-MeTHF

CAS: 36282-40-3 Molecular Formula: C7H7BrMgO Molecular Weight (g/mol): 211.34 MDL Number: MFCD00672002 InChI Key: AJKNYEHIJAMGHX-UHFFFAOYSA-M Synonym: 3-methoxyphenylmagnesium bromide,3-methoxyphenyl magnesium bromide,3-methoxyphenylmagnesium bromide solution,3-methoxyphenylmagnesiumbromide,3-methoxyphenylmagnesiumbromid,bromo 3-methoxyphenyl magnesium,3-methoxy phenylmagnesium bromide,3-methoxyphenyl-magnesium bromide,m-methoxyphenyl magnesium bromide,3-methoxylphenyl magnesium bromide,grignard reagent PubChem CID: 4605969 IUPAC Name: magnesium(2+) anisole bromide SMILES: COC1=CC=CC([Mg]Br)=C1

PubChem CID 4605969
CAS 36282-40-3
Molecular Weight (g/mol) 211.34
MDL Number MFCD00672002
SMILES COC1=CC=CC([Mg]Br)=C1
Synonym 3-methoxyphenylmagnesium bromide,3-methoxyphenyl magnesium bromide,3-methoxyphenylmagnesium bromide solution,3-methoxyphenylmagnesiumbromide,3-methoxyphenylmagnesiumbromid,bromo 3-methoxyphenyl magnesium,3-methoxy phenylmagnesium bromide,3-methoxyphenyl-magnesium bromide,m-methoxyphenyl magnesium bromide,3-methoxylphenyl magnesium bromide,grignard reagent
IUPAC Name magnesium(2+) anisole bromide
InChI Key AJKNYEHIJAMGHX-UHFFFAOYSA-M
Molecular Formula C7H7BrMgO
2

Benzylzinc bromide, 0.5M in THF, packaged under Argon in resealable ChemSeal™ bottles

CAS: 62673-31-8 Molecular Formula: C7H7BrZn Molecular Weight (g/mol): 236.417 MDL Number: MFCD00671803 InChI Key: WRSWIWOVJBYZAW-UHFFFAOYSA-M Synonym: benzylzinc bromide,benzyl bromo zinc,benzylzinc bromide solution,benzylzinc bromide, 0.50 m in thf,benzylzinc bromide 0.5 m in tetrahydrofuran,benzylzinc bromide solution, 0.5 m in thf,benzylzinc bromide, 0.5m in thf, packaged under argon in resealable chemseal bottles PubChem CID: 4443518 IUPAC Name: bromozinc(1+);methanidylbenzene SMILES: [CH2-]C1=CC=CC=C1.[Zn+]Br

PubChem CID 4443518
CAS 62673-31-8
Molecular Weight (g/mol) 236.417
MDL Number MFCD00671803
SMILES [CH2-]C1=CC=CC=C1.[Zn+]Br
Synonym benzylzinc bromide,benzyl bromo zinc,benzylzinc bromide solution,benzylzinc bromide, 0.50 m in thf,benzylzinc bromide 0.5 m in tetrahydrofuran,benzylzinc bromide solution, 0.5 m in thf,benzylzinc bromide, 0.5m in thf, packaged under argon in resealable chemseal bottles
IUPAC Name bromozinc(1+);methanidylbenzene
InChI Key WRSWIWOVJBYZAW-UHFFFAOYSA-M
Molecular Formula C7H7BrZn
3

4-(2-Tetrahydropyranyloxy)phenylmagnesium bromide, 0.5M in 2-MeTHF

CAS: 36637-44-2 Molecular Formula: C11H13BrMgO2 Molecular Weight (g/mol): 281.43 MDL Number: MFCD03427254 InChI Key: OHPUQUBYKZJOLY-UHFFFAOYNA-M Synonym: 4-2-tetrahydro-2h-pyranoxy phenylmagnesium bromide,ohpuqubykzjoly-uhfffaoysa-m,2-4-bromomagnesio phenoxy oxane,p-2-tetrahydropyranyloxy phenyl magnesium bromide,4-2-tetrahydro-3h-pyranoxy phenylmagnesium bromide,4-tetrahydropyran-2-yloxy phenyl magnesium bromide,4-2-tetrahydro-3-h-pyranoxy phenylmagnesium bromide,4-tetrahydro-2h-pyran-2-yloxy phenyl magnesium bromide,4-2-tetrahydro-2h-pyranoxy phenylmagnesium bromide solution,4-2-tetrahydropyranyloxy phenylmagnesium bromide, 0.5m in 2-methf,grignard reagent PubChem CID: 14519569 IUPAC Name: magnesium;2-(phenoxy)oxane;bromide SMILES: Br[Mg]C1=CC=C(OC2CCCCO2)C=C1

PubChem CID 14519569
CAS 36637-44-2
Molecular Weight (g/mol) 281.43
MDL Number MFCD03427254
SMILES Br[Mg]C1=CC=C(OC2CCCCO2)C=C1
Synonym 4-2-tetrahydro-2h-pyranoxy phenylmagnesium bromide,ohpuqubykzjoly-uhfffaoysa-m,2-4-bromomagnesio phenoxy oxane,p-2-tetrahydropyranyloxy phenyl magnesium bromide,4-2-tetrahydro-3h-pyranoxy phenylmagnesium bromide,4-tetrahydropyran-2-yloxy phenyl magnesium bromide,4-2-tetrahydro-3-h-pyranoxy phenylmagnesium bromide,4-tetrahydro-2h-pyran-2-yloxy phenyl magnesium bromide,4-2-tetrahydro-2h-pyranoxy phenylmagnesium bromide solution,4-2-tetrahydropyranyloxy phenylmagnesium bromide, 0.5m in 2-methf,grignard reagent
IUPAC Name magnesium;2-(phenoxy)oxane;bromide
InChI Key OHPUQUBYKZJOLY-UHFFFAOYNA-M
Molecular Formula C11H13BrMgO2
4

3-Cyanopropylzinc bromide, 0.5M in THF, packaged under Argon in resealable ChemSeal™ bottles

CAS: 135579-85-0 Molecular Formula: C4H6BrNZn Molecular Weight (g/mol): 213.38 MDL Number: MFCD00671975 InChI Key: HEHCQTGEYNYOSF-UHFFFAOYSA-M Synonym: 3-cyanopropylzinc bromide solution,3-cyanopropylzinc bromide,4-bromozincio butanenitrile,3-cyanopropylzinc bromide 0.5 m in tetrahydrofuran,3-cyanopropylzinc bromide solution, 0.5 m in thf,3-cyanopropylzinc bromide, 0.5m in thf, packaged under argon in resealable chemseal bottles PubChem CID: 4129356 IUPAC Name: bromozinc(1+);butanenitrile SMILES: [Zn+]Br.[CH2-]CCC#N

PubChem CID 4129356
CAS 135579-85-0
Molecular Weight (g/mol) 213.38
MDL Number MFCD00671975
SMILES [Zn+]Br.[CH2-]CCC#N
Synonym 3-cyanopropylzinc bromide solution,3-cyanopropylzinc bromide,4-bromozincio butanenitrile,3-cyanopropylzinc bromide 0.5 m in tetrahydrofuran,3-cyanopropylzinc bromide solution, 0.5 m in thf,3-cyanopropylzinc bromide, 0.5m in thf, packaged under argon in resealable chemseal bottles
IUPAC Name bromozinc(1+);butanenitrile
InChI Key HEHCQTGEYNYOSF-UHFFFAOYSA-M
Molecular Formula C4H6BrNZn
5

2-Thienylzinc bromide, 0.5M in THF, packaged under Argon in resealable ChemSeal™ bottles

CAS: 45438-80-0 Molecular Formula: C4H3BrSZn Molecular Weight (g/mol): 228.41 MDL Number: MFCD01317002 InChI Key: KRDONBTWAGIZME-UHFFFAOYSA-M Synonym: zinc 2h-thiophen-2-ide bromide,zinc 2+ ion thiophen-2-ide bromide PubChem CID: 4428324 IUPAC Name: bromozinc(1+);2H-thiophen-2-ide SMILES: [Zn+]Br.S1C=CC=[C-]1

PubChem CID 4428324
CAS 45438-80-0
Molecular Weight (g/mol) 228.41
MDL Number MFCD01317002
SMILES [Zn+]Br.S1C=CC=[C-]1
Synonym zinc 2h-thiophen-2-ide bromide,zinc 2+ ion thiophen-2-ide bromide
IUPAC Name bromozinc(1+);2H-thiophen-2-ide
InChI Key KRDONBTWAGIZME-UHFFFAOYSA-M
Molecular Formula C4H3BrSZn
6

4-Cyanophenylzinc bromide, 0.5M in THF, packaged under Argon in resealable ChemSeal™ bottles

CAS: 131379-14-1 Molecular Formula: C7H4BrNZn Molecular Weight (g/mol): 247.4 MDL Number: MFCD00671984 InChI Key: HEOMKTNNZDZMJZ-UHFFFAOYSA-M Synonym: zinc 2+ ion 4-cyanobenzen-1-ide bromide,zinc bromide 4-cyanobenzen-1-ide 1/1/1 PubChem CID: 54750729 IUPAC Name: zinc;benzonitrile;bromide SMILES: C1=CC(=CC=[C-]1)C#N.[Zn+2].[Br-]

PubChem CID 54750729
CAS 131379-14-1
Molecular Weight (g/mol) 247.4
MDL Number MFCD00671984
SMILES C1=CC(=CC=[C-]1)C#N.[Zn+2].[Br-]
Synonym zinc 2+ ion 4-cyanobenzen-1-ide bromide,zinc bromide 4-cyanobenzen-1-ide 1/1/1
IUPAC Name zinc;benzonitrile;bromide
InChI Key HEOMKTNNZDZMJZ-UHFFFAOYSA-M
Molecular Formula C7H4BrNZn
7

Phenylzinc bromide, 0.5M in THF, packaged under Argon in resealable ChemSeal™ bottles

CAS: 38111-44-3 Molecular Formula: C6H5BrZn Molecular Weight (g/mol): 222.39 MDL Number: MFCD01319861 InChI Key: HMFWJMIDCMEJHO-UHFFFAOYSA-M Synonym: phenylzinc bromide,zinc, bromophenyl,phenylzinc bromide solution,benzene,bromozinc 1+,phenylzinc bromide 0.5 m in tetrahydrofuran,phenylzinc bromide solution, 0.5 m in thf,phenylzinc bromide, 0.5m in thf, packaged under argon in resealable chemseal bottles PubChem CID: 16213817 IUPAC Name: zinc;benzene;bromide SMILES: [Zn++].[Br-].C1=CC=[C-]C=C1

PubChem CID 16213817
CAS 38111-44-3
Molecular Weight (g/mol) 222.39
MDL Number MFCD01319861
SMILES [Zn++].[Br-].C1=CC=[C-]C=C1
Synonym phenylzinc bromide,zinc, bromophenyl,phenylzinc bromide solution,benzene,bromozinc 1+,phenylzinc bromide 0.5 m in tetrahydrofuran,phenylzinc bromide solution, 0.5 m in thf,phenylzinc bromide, 0.5m in thf, packaged under argon in resealable chemseal bottles
IUPAC Name zinc;benzene;bromide
InChI Key HMFWJMIDCMEJHO-UHFFFAOYSA-M
Molecular Formula C6H5BrZn
8

3,5-Dimethylphenylmagnesium bromide, 0.5M in 2-MeTHF

CAS: 34696-73-6 Molecular Formula: C8H9BrMg Molecular Weight (g/mol): 209.37 MDL Number: MFCD01311497 InChI Key: XPXQQJMQESWIKM-UHFFFAOYSA-M Synonym: 3,5-dimethylphenylmagnesium bromide,xpxqqjmqeswikm-uhfffaoysa-m,3,5-dimethylphenyl magnesium bromide,3,5-dimethylphenylmagnesium bromide solution,3,5-dimethylphenylmagnesium bromide, 0.5m in 2-methf,3,5-dimethylphenylmagnesium bromide 0.5 m in tetrahydrofuran,3,5-dimethylphenylmagnesium bromide solution, 0.5 m in thf,grignard reagent PubChem CID: 10965748 IUPAC Name: magnesium;1,3-dimethylbenzene-5-ide;bromide SMILES: CC1=CC([Mg]Br)=CC(C)=C1

PubChem CID 10965748
CAS 34696-73-6
Molecular Weight (g/mol) 209.37
MDL Number MFCD01311497
SMILES CC1=CC([Mg]Br)=CC(C)=C1
Synonym 3,5-dimethylphenylmagnesium bromide,xpxqqjmqeswikm-uhfffaoysa-m,3,5-dimethylphenyl magnesium bromide,3,5-dimethylphenylmagnesium bromide solution,3,5-dimethylphenylmagnesium bromide, 0.5m in 2-methf,3,5-dimethylphenylmagnesium bromide 0.5 m in tetrahydrofuran,3,5-dimethylphenylmagnesium bromide solution, 0.5 m in thf,grignard reagent
IUPAC Name magnesium;1,3-dimethylbenzene-5-ide;bromide
InChI Key XPXQQJMQESWIKM-UHFFFAOYSA-M
Molecular Formula C8H9BrMg
9

2,4-Dimethylphenylmagnesium bromide, 0.5M in 2-MeTHF, Thermo Scientific™

CAS: 34589-46-3 Molecular Formula: C8H9BrMg Molecular Weight (g/mol): 209.37 MDL Number: MFCD01311493 InChI Key: HPGWKALAJLXSDH-UHFFFAOYSA-M Synonym: 2,4-dimethylphenylmagnesium bromide,2,4-dimethylphenylmagnesium bromide solution,hpgwkalajlxsdh-uhfffaoysa-m,2,4-dimethylphenylmagne-sium bromide,2,4-dimethylphenyl magnesium bromide,magnesium,1,3-dimethylbenzene-6-ide,bromide,2,4-dimethylphenylmagnesium bromide, 0.5m in 2-methf,2,4-dimethylphenylmagnesium bromide 0.5 m in tetrahydrofuran,2,4-dimethylphenylmagnesium bromide solution, 0.5 m in thf,grignard reagent PubChem CID: 13637491 IUPAC Name: magnesium;1,3-dimethylbenzene-6-ide;bromide SMILES: CC1=CC=C([Mg]Br)C(C)=C1

PubChem CID 13637491
CAS 34589-46-3
Molecular Weight (g/mol) 209.37
MDL Number MFCD01311493
SMILES CC1=CC=C([Mg]Br)C(C)=C1
Synonym 2,4-dimethylphenylmagnesium bromide,2,4-dimethylphenylmagnesium bromide solution,hpgwkalajlxsdh-uhfffaoysa-m,2,4-dimethylphenylmagne-sium bromide,2,4-dimethylphenyl magnesium bromide,magnesium,1,3-dimethylbenzene-6-ide,bromide,2,4-dimethylphenylmagnesium bromide, 0.5m in 2-methf,2,4-dimethylphenylmagnesium bromide 0.5 m in tetrahydrofuran,2,4-dimethylphenylmagnesium bromide solution, 0.5 m in thf,grignard reagent
IUPAC Name magnesium;1,3-dimethylbenzene-6-ide;bromide
InChI Key HPGWKALAJLXSDH-UHFFFAOYSA-M
Molecular Formula C8H9BrMg
10

Phenylmagnesium bromide, 3M in ether

CAS: 100-58-3 Molecular Formula: C6H5BrMg Molecular Weight (g/mol): 181.32 MDL Number: MFCD00000038 InChI Key: ANRQGKOBLBYXFM-UHFFFAOYSA-M Synonym: phenylmagnesium bromide,bromophenylmagnesium,magnesium, bromophenyl,phmgbr,phenylmagnesiumbromide,bromo phenyl magnesium,phenyl magnesium bromide,phenylmagnesium bromide solution, 3.0 m in diethyl ether,bromomagnesiobenzene,phenyhnagnesium bromide,grignard reagent PubChem CID: 66852 SMILES: Br[Mg]C1=CC=CC=C1

PubChem CID 66852
CAS 100-58-3
Molecular Weight (g/mol) 181.32
MDL Number MFCD00000038
SMILES Br[Mg]C1=CC=CC=C1
Synonym phenylmagnesium bromide,bromophenylmagnesium,magnesium, bromophenyl,phmgbr,phenylmagnesiumbromide,bromo phenyl magnesium,phenyl magnesium bromide,phenylmagnesium bromide solution, 3.0 m in diethyl ether,bromomagnesiobenzene,phenyhnagnesium bromide,grignard reagent
InChI Key ANRQGKOBLBYXFM-UHFFFAOYSA-M
Molecular Formula C6H5BrMg
11

Dibromo(1,5-cyclooctadiene)palladium(II), Pd 28.4%

CAS: 12145-47-0 Molecular Formula: C8H12Br2Pd Molecular Weight (g/mol): 374.41 MDL Number: MFCD00799635 InChI Key: MTEMVOIUTLIPJT-PHFPKPIQSA-L Synonym: dibromo 1,5-cyclooctadiene palladium ii,pdbr2 cod,dibromo 1,5-cyclooctadiene palladium,1,5-cyclooctadiene, z,z-; palladium ii bromide PubChem CID: 11187970 IUPAC Name: (1Z,5Z)-cycloocta-1,5-diene;dibromopalladium SMILES: Br[Pd+]Br.C1C\C=C/CC\C=C/1

PubChem CID 11187970
CAS 12145-47-0
Molecular Weight (g/mol) 374.41
MDL Number MFCD00799635
SMILES Br[Pd+]Br.C1C\C=C/CC\C=C/1
Synonym dibromo 1,5-cyclooctadiene palladium ii,pdbr2 cod,dibromo 1,5-cyclooctadiene palladium,1,5-cyclooctadiene, z,z-; palladium ii bromide
IUPAC Name (1Z,5Z)-cycloocta-1,5-diene;dibromopalladium
InChI Key MTEMVOIUTLIPJT-PHFPKPIQSA-L
Molecular Formula C8H12Br2Pd
12

4-Methoxyphenylmagnesium bromide, 0.5M in THF

CAS: 13139-86-1 Molecular Formula: C7H7BrMgO Molecular Weight (g/mol): 211.34 MDL Number: MFCD00013515 InChI Key: JKXAZEXIOPFJSC-UHFFFAOYSA-M Synonym: 4-methoxyphenylmagnesium bromide,4-methoxyphenylmagnesium bromide solution,bromo 4-methoxyphenyl magnesium,p-methoxyphenylmagnesium bromide,4-methoxyphenyl magnesium bromide,4-methoxyphenymagnesium bromide,4-methoxy phenylmagnesiumbromide,p-methoxyphenyl magnesium bromide,p-methoxyphenyl-magnesium bromide,4-methoxy-phenyl-magnesiumbromide,grignard reagent PubChem CID: 2734898 SMILES: COC1=CC=C([Mg]Br)C=C1

PubChem CID 2734898
CAS 13139-86-1
Molecular Weight (g/mol) 211.34
MDL Number MFCD00013515
SMILES COC1=CC=C([Mg]Br)C=C1
Synonym 4-methoxyphenylmagnesium bromide,4-methoxyphenylmagnesium bromide solution,bromo 4-methoxyphenyl magnesium,p-methoxyphenylmagnesium bromide,4-methoxyphenyl magnesium bromide,4-methoxyphenymagnesium bromide,4-methoxy phenylmagnesiumbromide,p-methoxyphenyl magnesium bromide,p-methoxyphenyl-magnesium bromide,4-methoxy-phenyl-magnesiumbromide,grignard reagent
InChI Key JKXAZEXIOPFJSC-UHFFFAOYSA-M
Molecular Formula C7H7BrMgO
13

1-Propynylmagnesium bromide, 0.5M solution in THF, AcroSeal™

CAS: 16466-97-0 Molecular Formula: C3H3BrMg Molecular Weight (g/mol): 143.27 MDL Number: MFCD00216588 InChI Key: YVJBCTFVENNIOV-UHFFFAOYSA-M Synonym: 1-propynylmagnesium bromide,1-propynyl magnesium bromide,bromo prop-1-yn-1-yl magnesium,1-propynylmagnesium bromide solution,propynylmagnesiumbromide,propynyl magnesium bromide,prop-1-ynylmagnesium bromide,prop-1-inyl magnesium bromide,prop-1-ynyl-magnesium bromide,propyn-1-yl magnesium bromide,grignard reagent PubChem CID: 3608069 IUPAC Name: magnesium;prop-1-yne;bromide SMILES: CC#C[Mg]Br

PubChem CID 3608069
CAS 16466-97-0
Molecular Weight (g/mol) 143.27
MDL Number MFCD00216588
SMILES CC#C[Mg]Br
Synonym 1-propynylmagnesium bromide,1-propynyl magnesium bromide,bromo prop-1-yn-1-yl magnesium,1-propynylmagnesium bromide solution,propynylmagnesiumbromide,propynyl magnesium bromide,prop-1-ynylmagnesium bromide,prop-1-inyl magnesium bromide,prop-1-ynyl-magnesium bromide,propyn-1-yl magnesium bromide,grignard reagent
IUPAC Name magnesium;prop-1-yne;bromide
InChI Key YVJBCTFVENNIOV-UHFFFAOYSA-M
Molecular Formula C3H3BrMg
14

p-Tolylmagnesium bromide, approx. 0.5M solution in diethyl ether, AcroSeal™

CAS: 4294-57-9 Molecular Formula: C7H7BrMg Molecular Weight (g/mol): 195.34 MDL Number: MFCD00000040 InChI Key: ZRJNGFJIBZKXTP-UHFFFAOYSA-M Synonym: p-tolylmagnesium bromide,magnesium, bromo 4-methylphenyl,4-methylphenylmagnesium bromide,bromo 4-methylphenyl magnesium,4-tolylmagnesium bromide,4-toluylmagnesium bromide,p-tolyl-magnesium bromide,4-tolyl magnesium bromide,4-methylphenylmagnesiumbromide,p-methylphenylmagnesium bromide,grignard reagent PubChem CID: 3644322 IUPAC Name: magnesium;methylbenzene;bromide SMILES: CC1=CC=C([Mg]Br)C=C1

PubChem CID 3644322
CAS 4294-57-9
Molecular Weight (g/mol) 195.34
MDL Number MFCD00000040
SMILES CC1=CC=C([Mg]Br)C=C1
Synonym p-tolylmagnesium bromide,magnesium, bromo 4-methylphenyl,4-methylphenylmagnesium bromide,bromo 4-methylphenyl magnesium,4-tolylmagnesium bromide,4-toluylmagnesium bromide,p-tolyl-magnesium bromide,4-tolyl magnesium bromide,4-methylphenylmagnesiumbromide,p-methylphenylmagnesium bromide,grignard reagent
IUPAC Name magnesium;methylbenzene;bromide
InChI Key ZRJNGFJIBZKXTP-UHFFFAOYSA-M
Molecular Formula C7H7BrMg
15

4-Methoxyphenylmagnesium bromide, 1M solution in THF, AcroSeal™

CAS: 13139-86-1 Molecular Formula: C7H7BrMgO Molecular Weight (g/mol): 211.34 MDL Number: MFCD00013515 InChI Key: JKXAZEXIOPFJSC-UHFFFAOYSA-M Synonym: 4-methoxyphenylmagnesium bromide,4-methoxyphenylmagnesium bromide solution,bromo 4-methoxyphenyl magnesium,p-methoxyphenylmagnesium bromide,4-methoxyphenyl magnesium bromide,4-methoxyphenymagnesium bromide,4-methoxy phenylmagnesiumbromide,p-methoxyphenyl magnesium bromide,p-methoxyphenyl-magnesium bromide,4-methoxy-phenyl-magnesiumbromide,grignard reagent PubChem CID: 2734898 IUPAC Name: magnesium;methoxybenzene;bromide SMILES: COC1=CC=C([Mg]Br)C=C1

PubChem CID 2734898
CAS 13139-86-1
Molecular Weight (g/mol) 211.34
MDL Number MFCD00013515
SMILES COC1=CC=C([Mg]Br)C=C1
Synonym 4-methoxyphenylmagnesium bromide,4-methoxyphenylmagnesium bromide solution,bromo 4-methoxyphenyl magnesium,p-methoxyphenylmagnesium bromide,4-methoxyphenyl magnesium bromide,4-methoxyphenymagnesium bromide,4-methoxy phenylmagnesiumbromide,p-methoxyphenyl magnesium bromide,p-methoxyphenyl-magnesium bromide,4-methoxy-phenyl-magnesiumbromide,grignard reagent
IUPAC Name magnesium;methoxybenzene;bromide
InChI Key JKXAZEXIOPFJSC-UHFFFAOYSA-M
Molecular Formula C7H7BrMgO