13291-18-4

Basic information

• Product Name: ISOPROPENYLMAGNESIUM BROMIDE
• Synonyms: Isopropenylmagnesium bromide, 0.5 M solution in THF, HySeal;Isopropenylmagnesium bromide 1M solution in tetrahydrofuran;ISOPROPENYLMAGNESIUM BROMIDE;isopropenylmagnesium bromide solution;ISOPROPENYLMAGNESIUM BROMIDE SOLUTION, ~ 0.5 M IN THF;ISOPROPENYLMAGNESIUM BROMIDE, 0.5M SOLUT ION IN TETRAHYDROFURAN;ISOPROPENYLMAGNESIUM BROMIDE in ETHYL ETHER;ISOPROPENYLMAGNESIUM BROMIDE in TETRAHYDROFURAN
• CAS NO: 13291-18-4
• Molecular Formula: C₃H₅BrMg
• Molecular Weight: 145.28
• Product Categories: Grignard Reagent;Alkenyl;Grignard Reagents;Organometallic Reagents
• Mol File: 13291-18-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 102-104 °C
• Boiling Point: 67 °C
• Flash Point: −36 °F
• Appearance: White to yellow to orange/Crystalline Powder
• Density: 0.94 g/mL at 20 °C
• Storage Temp.: 2-8°C
• BRN: 3587297
• CAS DataBase Reference: ISOPROPENYLMAGNESIUM BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ISOPROPENYLMAGNESIUM BROMIDE(13291-18-4)
• EPA Substance Registry System: ISOPROPENYLMAGNESIUM BROMIDE(13291-18-4)

Safety Data

• Hazard Codes: F,C
• Statements: 11-14/15-34-40-37-19-14
• Safety Statements: 26-30-36/37/39-43-45-7/8-16
• RIDADR: UN 3399 4.3/PG 1
• WGK Germany: 1
• F: 1-3-10-34
• Hazardous Substances Data: 13291-18-4(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 13291-18-4 differently. You can refer to the following data:
1. Grignard reagent in greener solvent, 2-methyltetrahydrofuran (2-MeTHF)2-Methyltetrahydrofuran (2-MeTHF): A Biomass-Derived Solvent with Broad Application in Organic Chemistry
2. Isopropenylmagnesium bromide (iPrMgBr) solution (0.5 M in THF) has been used in the Grignard reaction, a key step the in preparation of zofenoprilat and (S)-(?)-phosphonotrixin. It can also be used for the regioselective ring opening of an optically active epoxy alcohol in the total synthesis of (+)-desepoxyasperdiol.

General Description

This product, 1.0 M in 2-methyltetrahydrofuran aligns with Safer Solvents and Auxiliaries, Use of Renewable Feedstocks and Inherently Safer Chemistry for Accident Prevention.

InChI:InChI=1/C3H5.BrH.Mg/c1-3-2;;/h1H2,2H3;1H;/q;;+1/p-1/rC3H5BrMg/c1-3(2)5-4/h1H2,2H3

Synthetic route

2-bromoprop-1-ene (557-93-7) → isopropenylmagnesium bromide (13291-18-4)

Conditions	Yield
With magnesium In tetrahydrofuran at -78℃;
With magnesium In tetrahydrofuran for 0.5h; Heating;
With magnesium In tetrahydrofuran
With magnesium In monoethylene glycol diethyl ether

isopropenylmagnesium bromide (13291-18-4) + oxalic acid diethyl ester (95-92-1) → ethyl 3-methyl-2-oxobut-3-enoate (50331-71-0)

Conditions	Yield
In tetrahydrofuran; diethyl ether at -70℃; for 0.333333h;	100%
In tetrahydrofuran; diethyl ether at -60℃;	87%
In tetrahydrofuran; diethyl ether at -78℃; for 1.83333h; Inert atmosphere;	80%
In tetrahydrofuran; diethyl ether at -80℃;	3.75 g
In tetrahydrofuran; diethyl ether at -78℃;

isopropenylmagnesium bromide (13291-18-4) + (S)-tritylglycidol (129940-50-7) → (S)-4-methyl-1-(trityloxy)pent-4-en-2-ol (206660-79-9)

Conditions	Yield
With copper(l) iodide In tetrahydrofuran at -40 - -30℃; for 1h;	100%
Stage #1: isopropenylmagnesium bromide With copper(l) iodide In tetrahydrofuran at -78℃; for 0.5h; Stage #2: (S)-tritylglycidol In tetrahydrofuran at -40℃; for 2h; Further stages.;	100%
With copper(l) iodide In tetrahydrofuran at -30℃; for 1h; Ring cleavage; Grignard reaction;	99%
With copper(l) iodide In tetrahydrofuran at -30℃; for 1h;	99%

isopropenylmagnesium bromide (13291-18-4) + 1,2:5,6-dianhydro-3,4-O-methylethylidene-L-iditol (63699-97-8) → (1S)-1-{(4R,5R)-5-[(1S)-1-hydroxy-3-methyl-3-butenyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-3-methyl-3-buten-1-ol (387392-14-5)

Conditions	Yield
Stage #1: isopropenylmagnesium bromide With copper(l) iodide In tetrahydrofuran at -40℃; for 0.5h; Stage #2: 1,2:5,6-dianhydro-3,4-O-methylethylidene-L-iditol In tetrahydrofuran at -40 - -30℃; for 2h;	100%
With copper(l) iodide In tetrahydrofuran at -40℃; for 2h;	92%

isopropenylmagnesium bromide (13291-18-4) + 1-<α-(Dibenzylamino)benzyl>benzotriazole (133384-09-5) → N,N-dibenzyl-2-methyl-1-phenyl-2-propen-1-ylamine

Conditions	Yield
In tetrahydrofuran; toluene at 50℃; for 2h; Inert atmosphere;	100%
In tetrahydrofuran; toluene at 50℃; for 2h;	86%

isopropenylmagnesium bromide (13291-18-4) → isopropenylboronic acid (14559-87-6)

Conditions	Yield
Stage #1: isopropenylmagnesium bromide With Trimethyl borate In tetrahydrofuran at 20℃; for 2h; Stage #2: With hydrogenchloride; water In tetrahydrofuran at 0℃; for 0.25h;	100%
With Trimethyl borate In tetrahydrofuran at 20℃;	88%
With Trimethyl borate In tetrahydrofuran at 20℃; for 2h;	1.5 g

isopropenylmagnesium bromide (13291-18-4) + tert-butyl (2S)-2-(methoxyacetyl)indoline-1-carboxylate (500548-61-8) → (S)-2-((S)-1-Hydroxy-1-methoxymethyl-2-methyl-allyl)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester + tert-butyl (2S)-2-[(1R)-1-hydroxy-1-(methoxymethyl)-2-methylallyl]indoline-1-carboxylate (500548-71-0)

Conditions	Yield
In tetrahydrofuran at -78℃; for 0.25h; Grignard addition;	A n/a B 100%

isopropenylmagnesium bromide (13291-18-4) + (1R,2R,5S,6S)-2,5-Bis-(4-methoxy-benzyloxy)-7-oxa-bicyclo[4.1.0]heptane (350708-56-4) → (1S,2S,3S,6R)-2-Isopropenyl-3,6-bis-(4-methoxy-benzyloxy)-cyclohexanol

Conditions	Yield
In tetrahydrofuran; diethyl ether at -10℃;	100%

2-carbonyl-3-benzyl-5-hydropyridino[1,2-a]pyrimidin-4-one (817206-01-2) + isopropenylmagnesium bromide (13291-18-4) → 3-benzyl-2-(1-hydroxy-2-methylprop-2-enyl)-4H-pyrido[1,2-a]pyrimidin-4-one (866611-15-6)

Conditions	Yield
Stage #1: 2-carbonyl-3-benzyl-5-hydropyridino[1,2-a]pyrimidin-4-one; isopropenylmagnesium bromide In tetrahydrofuran at -78℃; for 2h; Stage #2: With water; ammonium chloride In tetrahydrofuran	100%

isopropenylmagnesium bromide (13291-18-4) + 2-oxo-butyric acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-cyclohexyl ester (146596-05-6) → (2S)-2-ethyl-2-hydroxy-3-methyl-but-3-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (880815-57-6)

Conditions	Yield
Stage #1: isopropenylmagnesium bromide; 2-oxo-butyric acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-cyclohexyl ester In tetrahydrofuran at -78℃; for 0.833333h; Grignard Addition; Stage #2: With water; ammonium chloride In tetrahydrofuran	100%

4-Trifluoromethylbenzaldehyde (455-19-6) + isopropenylmagnesium bromide (13291-18-4) → 1-[4-(trifluoromethyl)phenyl]-2-methylprop-2-en-1-ol (1204403-36-0)

Conditions	Yield
Stage #1: 4-Trifluoromethylbenzaldehyde; isopropenylmagnesium bromide In tetrahydrofuran at 0℃; for 2h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; water Inert atmosphere;	100%
In acetonitrile at 0 - 5℃; for 3h; Inert atmosphere;

[4-(benzyloxy)phenyl](6-bromopyridin-3-yl)methanone + isopropenylmagnesium bromide (13291-18-4) → 1-[4-(benzyloxy)phenyl]-1-(6-bromopyridin-3-yl)-2-methylprop-2-en-1-ol

Conditions	Yield
In tetrahydrofuran for 0.0166667h;	100%

isopropenylmagnesium bromide (13291-18-4) + zinc(II) chloride (7646-85-7) → prop-1-en-2-ylzinc(II) chloride (119441-91-7)

Conditions	Yield
With lithium chloride In tetrahydrofuran Inert atmosphere;	100%
With N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 20℃; for 0.166667h;

cyclohexanedione monoethylene ketal (4746-97-8) + isopropenylmagnesium bromide (13291-18-4) → 8-(Prop-1-en-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol

Conditions	Yield
In tetrahydrofuran at 0 - 5℃; for 2h; Inert atmosphere;	100%
In tetrahydrofuran at 0 - 5℃; for 4h; Inert atmosphere;
In tetrahydrofuran at 5℃; for 2h;

(S)-2-(benzyloxy)-1-(4-fluoro-3-methylphenyl)propan-1-one + isopropenylmagnesium bromide (13291-18-4) → (4S)-4-(benzyloxy)-3-(4-fluorophenyl)-2-methylpent-1-en-3-ol

Conditions	Yield
In tetrahydrofuran; 2-methyltetrahydrofuran at 0℃; for 2h; Cooling with ice;	100%

isopropenylmagnesium bromide (13291-18-4) + (S,E)-3-(4-(furan-2-yl)but-2-enoyl)-4-phenyloxazolidin-2-one → (S)-3-((R)-3-(furan-2-ylmethyl)-4-methylpent-4-enoyl)-4-phenyloxazolidin-2-one

Conditions	Yield
Stage #1: isopropenylmagnesium bromide With copper(I) bromide dimethylsulfide complex In tetrahydrofuran at -78℃; for 1.16667h; Stage #2: (S,E)-3-(4-(furan-2-yl)but-2-enoyl)-4-phenyloxazolidin-2-one In tetrahydrofuran for 1h;	100%

5-[[(2R)-oxiran-2-yl]methoxy]-1,3-benzodioxole (329977-77-7) + isopropenylmagnesium bromide (13291-18-4) → (R)-1-(benzo[d][1,3]dioxol-5-yloxy)-4-methylpent-4-en-2-ol

Conditions	Yield
Stage #1: isopropenylmagnesium bromide With copper(II) iodide In tetrahydrofuran at -40℃; for 0.583333h; Inert atmosphere; Stage #2: 5-[[(2R)-oxiran-2-yl]methoxy]-1,3-benzodioxole In tetrahydrofuran at -40℃; for 2.5h;	100%

3-phenyl-propionaldehyde (104-53-0) + isopropenylmagnesium bromide (13291-18-4) → (+/-)-2-methyl-5-phenylpent-1-en-3-ol (123718-22-9, 1836-38-0)

Conditions	Yield
at 0 - 20℃; for 3h;	99%
In tetrahydrofuran at 0 - 20℃; for 3.5h; Inert atmosphere;	88%
In tetrahydrofuran at 0 - 20℃; for 3.5h; Inert atmosphere;	88%

heptanal (111-71-7) + isopropenylmagnesium bromide (13291-18-4) → 2-methyl-1-nonen-3-ol (52500-37-5)

Conditions	Yield
In tetrahydrofuran for 0.5h; Ambient temperature;	99%
In tetrahydrofuran at 0℃;

isopropenylmagnesium bromide (13291-18-4) + 6-(trimethylsilyl)-4-hexynal (117416-13-4) → 2-methyl-8-(trimethylsilyl)oct-1-en-6-yn-3-ol (74377-88-1)

Conditions	Yield
In tetrahydrofuran at -5℃; for 1.5h;	99%
In tetrahydrofuran at 0℃; for 0.5h;

isopropenylmagnesium bromide (13291-18-4) + (+/-)-5-(2-methoxymethoxyethyl)-7-methylidene-cis-bicyclo<3.2.1>oct-3-en-2-one → (1R*,4S*,5S*)-5-(2-methoxymethoxyethyl)-4-methylethenyl-7-methylidenebicyclo[3.2.1]octan-2-one

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex In tetrahydrofuran at -78℃; for 0.5h;	99%

isopropenylmagnesium bromide (13291-18-4) + (3S,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-al (188730-08-7) → (E)-(S)-5-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-7-(2-methyl-thiazol-4-yl)-hepta-1,6-dien-3-ol

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 1h; Grignard reaction;	99%

3-furan-2-yl-propenal (623-30-3) + isopropenylmagnesium bromide (13291-18-4) → 1-(furan-2-yl)-4-methyl-penta-1,4-dien-3-ol

Conditions	Yield
In tetrahydrofuran at 0℃; for 0.5h;	99%

5-(furan-2-yl)-penta-2,4-dienal (5916-94-9) + isopropenylmagnesium bromide (13291-18-4) → 7-(furan-2-yl)-2-methyl-hepta-1,4,6-trien-3-ol

Conditions	Yield
In tetrahydrofuran at 0℃; for 0.5h;	99%

(E)-2-decenal (3913-81-3) + isopropenylmagnesium bromide (13291-18-4) → 2-methyl-dodeca-1,4-dien-3-ol (1013890-31-7)

Conditions	Yield
In tetrahydrofuran at 0℃; for 0.5h;	99%

2E,4E-5,9-dimethyldeca-2,4-8-trienal (86306-35-6) + isopropenylmagnesium bromide (13291-18-4) → 2,7,11-trimethyl-dodeca-1,4,6,10-tetraen-3-ol

Conditions	Yield
In tetrahydrofuran at 0℃; for 0.5h;	99%

(R)-tert-butyldimethyl(4-(oxiran-2-yl)butoxy)silane (952103-37-6) + isopropenylmagnesium bromide (13291-18-4) → C15H32O2Si (1109114-99-9)

Conditions	Yield
With copper(l) iodide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; optical yield given as %ee;	99%

isopropenylmagnesium bromide (13291-18-4) + (R)-phenyl glycidyl ether (71031-03-3) → (S)-4-methyl-1-phenoxypent-4-en-2-ol (1177441-30-3)

Conditions	Yield
Stage #1: isopropenylmagnesium bromide With copper(l) iodide In tetrahydrofuran at -30℃; for 0.25h; Stage #2: (R)-phenyl glycidyl ether In tetrahydrofuran at -30 - 20℃; for 3h;	99%

(S)-5-(oxiran-2-ylmethylthio)-1-phenyl-1H-tetrazole (1198463-58-9) + isopropenylmagnesium bromide (13291-18-4) → (S)-4-methyl-1-(1-phenyl-1H-tetrazol-5-ylthio)pent-4-en-2-ol (1198463-43-2)

Conditions	Yield
Stage #1: isopropenylmagnesium bromide With copper(l) iodide In tetrahydrofuran at -30℃; Inert atmosphere; Stage #2: (S)-5-(oxiran-2-ylmethylthio)-1-phenyl-1H-tetrazole In tetrahydrofuran at -30 - 0℃; Inert atmosphere;	99%
Stage #1: isopropenylmagnesium bromide With copper(l) iodide In tetrahydrofuran at -30℃; for 0.0833333h; Inert atmosphere; Stage #2: (S)-5-(oxiran-2-ylmethylthio)-1-phenyl-1H-tetrazole In tetrahydrofuran at -30 - 0℃; Inert atmosphere; regioselective reaction;	99%

furfural (98-01-1) + isopropenylmagnesium bromide (13291-18-4) → (±)-1-(furan-2-yl)-2-methylprop-2-en-1-ol (196879-17-1)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 0.333333h; Inert atmosphere;	99%
Stage #1: furfural; isopropenylmagnesium bromide In tetrahydrofuran at 0℃; for 2h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; water Inert atmosphere;	90%

thiophene-2-carbaldehyde (98-03-3) + isopropenylmagnesium bromide (13291-18-4) → (±)-2-methyl-1-(thiophen-2-yl)prop-2-en-1-ol (1245792-94-2)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 0.333333h; Inert atmosphere;	99%
Stage #1: thiophene-2-carbaldehyde; isopropenylmagnesium bromide In tetrahydrofuran at 0℃; for 2h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; water Inert atmosphere;	91%

Upstream product

• 557-93-7 2-bromoprop-1-ene 

Downstream Products

• 61342-06-1 3,5-Di-isopropenyl-1-chlorbenzol 
• 14559-87-6 isopropenylboronic acid 
• 7071-28-5 1-Cyclohexyliden-3-methyl-2-hydroxy-buten-3 
• 1855-47-6 1-(propen-2-yl)naphthalene 
• 64723-79-1 N-(1,3,3,4-tetramethyl-pent-4-enylidene)-aniline 
• 24350-58-1 (±)-(1S,2R)-2-(prop-1-en-2-yl)cyclohexanol 
• 10473-13-9 2,3-dimethyl-1-buten-3-ol 
• 61765-62-6 3-(prop-1-en-2-yl)cyclohex-2-enone 
• 133565-98-7 1-(1-methylethenyl)benzocyclobuten-1-ol 
• 20077-60-5 Benzyl 3-methyl-2-oxo-3-butenoate 
• 3019-20-3 isopropylthiobenzene 
• 85109-95-1 p-(1-methylethenyl)phenyl i-propyl sulphide 
• 131510-65-1 1-Acetyl-2-isopropenyl-2-methylcyclobutane 
• 96413-06-8 3-Methyl-1-(triphenyl-λ⁵-phosphanylidene)-but-3-en-2-one 

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