3536-96-7

Basic information

• Product Name: Vinylmagnesium chloride
• Synonyms: VINYLMAGNESIUM CHLORIDE;Vinylmagnesium chloride solution;chlorovinylmagnesium;Vinylmagnesium;VINYLMAGNESIUM CHLORIDE, 1.6M SOLUTION IN TETRAHYDROFURAN;VINYLMAGNESIUM CHLORIDE SOLUTION, ~1.7 M IN TETRAHYDROFURAN;Vinylmagnesium chloride, 15 wt% solution in tetrahydrofuran;VINYLMAGNESIUMCHLORIDE,15%(W/W)SOLUTIONINTETRAHYDROFURAN
• CAS NO: 3536-96-7
• Molecular Formula: C₂H₃ClMg
• Molecular Weight: 86.8
• EINECS: 222-575-9
• Product Categories: Alkenyl;Grignard Reagents;Organometallic Reagents;Grignard Reagent
• Mol File: 3536-96-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 66 °C
• Flash Point: −1 °F
• Appearance: White to beige/Crystalline Powder
• Density: 0.980 g/mL at 20 °C
• Storage Temp.: 0-6°C
• Water Solubility: vigorous reaction
• BRN: 3535268
• CAS DataBase Reference: Vinylmagnesium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Vinylmagnesium chloride(3536-96-7)
• EPA Substance Registry System: Vinylmagnesium chloride(3536-96-7)

Safety Data

• Hazard Codes: F,C
• Statements: 11-14/15-19-22-34-40-37
• Safety Statements: 16-26-36/37/39-43-45-7/8-43B-30
• RIDADR: UN 3399 4.3/PG 1
• WGK Germany: 1
• F: 1-3-10
• Hazardous Substances Data: 3536-96-7(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 3536-96-7 differently. You can refer to the following data:
1. Grignard reagent.
2. Vinylmagnesium chloride (Grignard reagent) can be prepared from vinyl chloride and then used to make a variety of useful end products or intermediates by adding a vinyl anion to organic functional groups. For instance, the vinylmagnesium compounds can be coupled with cuprous chloride, CuCl, at ?60 °C (?76 °F) to give 1,3-butadiene, while vinyl ketones and alcohols can be prepared by the addition of vinylmagnesium chloride to organic acids.
3. Used with iron pentadienoate complexes in a synthesis of divinyl cyclopropanes.

InChI:InChI=1/C2H3.ClH.Mg/c1-2;;/h1H,2H2;1H;/q;;+1/p-1/rC2H3Mg.ClH/c1-2-3;/h2H,1H2;1H/q+1;/p-1

Synthetic route

chloroethylene (75-01-4) → vinylmagnesium chloride (3536-96-7)

Conditions	Yield
With magnesium In tetrahydrofuran
With magnesium In tetrahydrofuran at 50℃; for 0.75h;
With magnesium; ethylene dibromide In tetrahydrofuran at 25 - 60℃;
With magnesium In tert-butyl methyl ether at 50℃; for 8h; Inert atmosphere;

chloroethylene (75-01-4) + magnesium (7439-95-4) → vinylmagnesium chloride (3536-96-7)

Conditions	Yield
In tetrahydrofuran
Stage #1: magnesium With iodine; ethylene dibromide In tetrahydrofuran at 60 - 64℃; Stage #2: chloroethylene In tetrahydrofuran at 60 - 64℃;

vinylmagnesium chloride (3536-96-7) + benzaldehyde (100-52-7) → 1-Phenyl-2-propen-1-ol (4393-06-0)

Conditions	Yield
In tetrahydrofuran at 0℃; for 2h; Inert atmosphere;	100%
In tetrahydrofuran at -10 - 20℃; Schlenk technique;	95%
In tetrahydrofuran at -10℃; for 2h; Inert atmosphere;	93%

4-chlorobutyraldehyde (6139-84-0) + vinylmagnesium chloride (3536-96-7) → 6-chloro-1-hexen-3-ol (167751-21-5)

Conditions	Yield
In tetrahydrofuran at -20℃; for 0.333333h;	100%

(1S,2R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-hydroxy-1,3-dimethyl-cyclohex-3-enecarbaldehyde + vinylmagnesium chloride (3536-96-7) → (1S,5S,6R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((S)-1-hydroxy-allyl)-4,6-dimethyl-cyclohex-3-enol

Conditions	Yield
In tetrahydrofuran at 0℃;	100%

2-(4-fluorophenyl)-N-methoxy-N-methylacetamide (457948-95-7) + vinylmagnesium chloride (3536-96-7) → 1-(4-fluorophenyl)but-3-en-2-one (860642-35-9) + 2-(4-fluorophenyl)-N-methoxyacetamide (119114-45-3) + C12H16FNO2 + N-Methoxy-N-methylacetamide (78191-00-1)

Conditions	Yield
Stage #1: 2-(4-fluorophenyl)-N-methoxy-N-methylacetamide; vinylmagnesium chloride In tetrahydrofuran; toluene at -30℃; for 2h; Stage #2: With acetic anhydride In tetrahydrofuran; toluene at -30℃; for 0.5h; Stage #3: With ammonium chloride In tetrahydrofuran; water; toluene at -30 - 10℃;	A 100% B n/a C n/a D n/a

(R,R)-2,3-butanediol (dichloromethyl)boronate (98632-84-9) + pinanediol (18680-27-8) + vinylmagnesium chloride (3536-96-7) → (s)-pinanediol {(S)-1-chloro-allyl}boronate

Conditions	Yield
With zinc(II) chloride In tetrahydrofuran; Petroleum ether to borolane (THF, -78°C) added vinylmagnesium chloride (THF), after 15 min ZnCl2 (THF) added, warmed (0°C), stirred (4h), filtered without moisture, concd. in vac., treated with petroleum ether, filtered, diol added, stirred; after 15 h aq. phase separated, extracted with ether, combined extracts dried over Na2SO4, concd., (1)H-NMR;	100%

bis[(μ-dimethylsilyl)(η5-cyclopentadienyl)]dichlorozirconium (154675-56-6) + vinylmagnesium chloride (3536-96-7) → [Zr(C5H3(CH3)4Si2C5H3)(CHCH2)2] (260786-65-0)

Conditions	Yield
In tetrahydrofuran; tetrahydrofuran-d8 dichlorozirconocene in THF and soln. of MgCl(CHCH2) in THF-d8 was sealed in vac. (-78°C); heated (5 min, -50°C); not isolated; detected by NMR;	100%

C23H42O3Si (1221900-15-7) + vinylmagnesium chloride (3536-96-7) → C25H46O3Si (1221900-35-1)

Conditions	Yield
In tetrahydrofuran; diethyl ether at -40℃; for 1.5h; Inert atmosphere;	100%

vinylmagnesium chloride (3536-96-7) + (R)-benzyl glycidol (14618-80-5) + acryloyl chloride (814-68-6) → Acrylic acid (R)-1-benzyloxymethyl-but-3-enyl ester (640298-47-1)

Conditions	Yield
Stage #1: vinylmagnesium chloride; (R)-benzyl glycidol With copper(l) iodide In tetrahydrofuran at 0℃; for 1h; Stage #2: acryloyl chloride With ethylmagnesium bromide In tetrahydrofuran at 20℃; for 1.5h;	100%

(R,E)-2-(4-(benzyloxy)-2-(5-(benzyloxy)pent-3-en-2-yl)-5-methylphenoxy)-N-methoxy-N,2-dimethylpropanamide (1313708-50-7) + vinylmagnesium chloride (3536-96-7) → (R,E)-4-(4-(benzyloxy)-2-(5-(benzyloxy)pent-3-en-2-yl)-5-methylphenoxy)-4-methylpent-1-en-3-one (1313708-48-3)

Conditions	Yield
In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;	100%

2-(3-bromophertyl)-6,6-dimethyl-6,7-dihydrobenzo[b]thiophen-4(5H)-one + vinylmagnesium chloride (3536-96-7) → 2-(3-bromophenyl)-6,6-dimethyl-4-vinyl-4,5,6,7-tetrahydrobenzo[b]thiophen-4-ol

Conditions	Yield
In tetrahydrofuran at -30 - 25℃; for 18h; Inert atmosphere;	100%
In tetrahydrofuran at -30 - 25℃; for 20h; Inert atmosphere;	100%

vinylmagnesium chloride (3536-96-7) + (S)-2-(((4-chlorobenzyl)oxy)methyl)oxirane (930278-81-2) → (S)-1-((4-chlorobenzyl)oxy)pent-4-en-2-ol

Conditions	Yield
With copper(l) iodide In tetrahydrofuran at -10℃;	100%

1,5-diphenyl-3-pentanone (5396-91-8) + vinylmagnesium chloride (3536-96-7) → 3-phenethyl-5-phenyl-pent-1-en-3-ol

Conditions	Yield
In tetrahydrofuran at 0℃; for 0.5h; Grignard Reaction;	100%

1-(5-bromo-2-fluorophenyl)ethan-1-one (198477-89-3) + vinylmagnesium chloride (3536-96-7) → 2-(5-bromo-2-fluorophenyl)but-3-en-2-ol

Conditions	Yield
In tetrahydrofuran; 2-methyltetrahydrofuran at -20 - 0℃; for 2h; Inert atmosphere;	100%

vinylmagnesium chloride (3536-96-7) + 2-Methyl-propane-2-sulfinic acid (S)-1-methyl-2,2-diphenyl-ethyl ester → (R)-tert-butyl vinyl sulfoxide (126494-93-7)

Conditions	Yield
In tetrahydrofuran; acetone at 25℃; for 0.5h;	99%

vinylmagnesium chloride (3536-96-7) + 4-methoxy-benzaldehyde (123-11-5) → 1-(4-methoxylphenyl)-2-propen-1-ol (51410-44-7)

Conditions	Yield
In tetrahydrofuran at 23℃;	99%
In tetrahydrofuran; diethyl ether at -15℃; for 1.5h; Inert atmosphere;	89%
In tetrahydrofuran at 0℃;

vinylmagnesium chloride (3536-96-7) + (R)-2-allyloxy-1,2-diphenylethanone (497239-72-2) → (1R,2S)-1-allyloxy-1,2-diphenylbut-3-en-2-ol (497239-78-8)

Conditions	Yield
In tetrahydrofuran; diethyl ether at -78℃;	99%

5-(trimethylsilyl)pent-4-ynal (68654-85-3) + vinylmagnesium chloride (3536-96-7) → 3-hydroxy-7-(trimethylsilyl)-1,6-heptenyne (88304-13-6, 135821-32-8, 69361-42-8)

Conditions	Yield
In tetrahydrofuran at 0℃;	99%
In tetrahydrofuran at 0℃; for 0.25h;	98%

2-methoxy-3-methylbenzaldehyde (824-42-0) + vinylmagnesium chloride (3536-96-7) → 2-(1-hydroxyallyl)-6-methylphenol (911817-84-0)

Conditions	Yield
In tetrahydrofuran at -78 - 20℃; for 0.5h; Inert atmosphere;	99%
Stage #1: 2-methoxy-3-methylbenzaldehyde; vinylmagnesium chloride In tetrahydrofuran at 0 - 20℃; for 18.75h; Stage #2: With water; ammonium chloride In tetrahydrofuran at 0 - 20℃; for 0.5h; Product distribution / selectivity;
Stage #1: 2-methoxy-3-methylbenzaldehyde; vinylmagnesium chloride In tetrahydrofuran; toluene at 0 - 25℃; for 2.25h; Stage #2: With water; ammonium chloride In tetrahydrofuran; toluene at 0 - 25℃; for 1h; Product distribution / selectivity;

vinylmagnesium chloride (3536-96-7) + 1-Phenyl-2-(trimethylsilyl)acetylene (2170-06-1) → (Z)-trimethyl(2-phenylbut-1-en-1-yl)silane (68669-61-4)

Conditions	Yield
Stage #1: vinylmagnesium chloride With CpYH2 In tetrahydrofuran; hexane at 20℃; for 0.5h; Stage #2: 1-Phenyl-2-(trimethylsilyl)acetylene In tetrahydrofuran; hexane at 55℃; for 3h; Further stages.;	99%

vinylmagnesium chloride (3536-96-7) + (R)-2-(((4-methoxybenzyl)oxy)methyl)oxirane (80910-01-6, 108836-41-5, 144069-33-0, 134733-19-0) → (R)-1-[(4-methoxybenzyl)oxy]pent-4-en-2-ol (194342-84-2)

Conditions	Yield
Stage #1: vinylmagnesium chloride; (R)-2-(((4-methoxybenzyl)oxy)methyl)oxirane With copper(l) iodide In tetrahydrofuran at -78 - 20℃; Inert atmosphere; Stage #2: With ammonia; water; ammonium chloride In tetrahydrofuran at 20℃;	99%

vinylmagnesium chloride (3536-96-7) + (S)-benzyl glycidyl ether (2930-05-4, 14618-80-5, 89616-40-0, 16495-13-9) → (2S)-1-(benzyloxy)pent-4-en-2-ol (88981-35-5)

Conditions	Yield
With copper(l) iodide In tetrahydrofuran at -10℃;	99%
Stage #1: vinylmagnesium chloride; (S)-benzyl glycidyl ether With copper(l) chloride In tetrahydrofuran at -10 - 0℃; Large scale reaction; Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water at 0 - 10℃; for 1h; optical yield given as %ee; regioselective reaction;	94%

bis(p-methoxyphenyl)methanone (90-96-0) + vinylmagnesium chloride (3536-96-7) → 1,1-bis(4-methoxyphenyl)prop-2-en-1-ol (101018-40-0)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 2.5h; Inert atmosphere;	99%
In tetrahydrofuran at 0 - 20℃;	91%
In tetrahydrofuran

2-hydroxy-5-t-butylbenzaldehyde (2725-53-3) + vinylmagnesium chloride (3536-96-7) → 4-(tert-butyl)-2-(1-hydroxyallyl)phenol

Conditions	Yield
In tetrahydrofuran at -78 - 20℃; for 0.5h; Inert atmosphere;	99%

5-iodosalicyclaldehyde (1761-62-2) + vinylmagnesium chloride (3536-96-7) → 2-(1-hydroxyallyl)-4-iodophenol

Conditions	Yield
In tetrahydrofuran at -78 - 20℃; for 0.5h; Inert atmosphere;	99%

o-hydroxyacetophenone (118-93-4) + vinylmagnesium chloride (3536-96-7) → 2-(2'-hydroxyphenyl)but-3-en-2-ol (38865-41-7)

Conditions	Yield
In tetrahydrofuran at -78 - 20℃; for 0.5h; Inert atmosphere;	99%

2-Hydroxybenzophenone (117-99-7) + vinylmagnesium chloride (3536-96-7) → 1-(2'-hydroxyphenyl)-1-phenylprop-2-en-1-ol (38865-43-9)

Conditions	Yield
In tetrahydrofuran at -78 - 20℃; for 0.5h; Inert atmosphere;	99%

(S)-2-(((4-bromobenzyl)oxy)methyl)oxirane (897961-91-0) + vinylmagnesium chloride (3536-96-7) → (S)-1-((4-bromobenzyl)oxy)pent-4-en-2-ol

Conditions	Yield
With copper(l) iodide In tetrahydrofuran at -10℃;	99%

(2Z)-non-2-enal (60784-31-8) + vinylmagnesium chloride (3536-96-7) → (Z)-undeca-1,4-dien-3-ol (119771-53-8)

Conditions	Yield
In tetrahydrofuran at 0℃; for 2h; Inert atmosphere;	99%

(±)-6-methoxy-2,6-dimethylheptanal + vinylmagnesium chloride (3536-96-7) → 8-methoxy-4,8-dimethylnon-1-en-3-ol

Conditions	Yield
In tetrahydrofuran at 20 - 25℃;	98.2%

vinylmagnesium chloride (3536-96-7) + 5-Formyl-1-(6-chloro-1-oxohex-2-ynyl)-2,6,6-trimethylcyclohex-1-ene (189444-01-7) → 1-(6-Chloro-1-oxohex-2-ynyl)-5-(1-hydroxyprop-2-enyl)-2,6,6-trimethylcyclohex-1-ene (216978-21-1)

Conditions	Yield
In tetrahydrofuran at -78℃; for 2h;	98%

Upstream product

• 75-01-4 chloroethylene 
• 7439-95-4 magnesium 

Downstream Products

• 1112-06-7 vinylpentamethyldisilane 
• 75144-60-4 hexavinyldisiloxane 
• 18414-59-0 diphenyl(vinyl)silane 
• 61193-58-6 (Diphenylarsino)ethen 
• 1822-73-7 phenylthioethylene 
• 103597-19-9 methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-D-glycero-α-D-glucooct-7-eno-1,5-pyranoside 
• 103597-23-5 methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-L-glycero-α-D-gluco-oct-7-ene-1,5-pyranoside 
• 72834-87-8 1-[3,7-Dimethyl-nona-1-yne-3,5,8-trien-7-ol-1-yl]-2,6,6-trimethyl-cyclohex-1-ene 
• 7071-29-6 4-cyclohexylidenepent-1-en-3-ol 
• 56431-05-1 4-n-Butyl-α-vinyl-benzhydrol 
• 6221-41-6 2-Isopropyl-4-methyl-1-vinyl-cyclohexanol 
• 66534-99-4 1-phenyl-1-vinyltetramethyldisilane 
• 56431-06-2 2,4-Dimethoxy-α-vinyl-benzhydrol 
• 56431-03-9 2-fluoro-α-vinyl-benzhydrol 

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