56039-93-1

Usage

Uses

Used in Organic Synthesis:
Magnesium, 3-butenylchlorois used as a nucleophile in Grignard reactions for the formation of new carbon-carbon bonds. It plays a crucial role in the synthesis of various organic compounds.
Used in Pharmaceutical Industry:
Magnesium, 3-butenylchlorois utilized in the preparation of pharmaceuticals. Its reactivity in Grignard reactions allows for the synthesis of complex organic molecules with potential medicinal properties.
Used in Agrochemical Industry:
In the agrochemical industry, Magnesium, 3-butenylchlorois employed in the synthesis of various agrochemicals. Its ability to form new carbon-carbon bonds through Grignard reactions contributes to the development of effective crop protection agents and other agricultural products.
Safety Precautions:
Due to its high reactivity, Magnesium, 3-butenylchloromust be handled with extreme caution. It is flammable and can react violently with water and air, posing a risk of fire or explosion. Proper safety measures, including the use of protective equipment and controlled environments, should be taken during its handling and use.

Synthetic route

(E)-(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl 4-(tert-butyldimethylsilyl)-2-((4-methoxyphenyl)imino)but-3-ynoate + 3-butenylmagnesium chloride (56039-93-1) → (R)-(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl 2-((tert-butyldimethylsilyl)ethynyl)-2-(phenylamino)hex-5-enoate

Conditions

Yield

Stage #1: 3-butenylmagnesium chloride With (trimethylsilyl)methylmagnesium chloride; lithium chloride; zinc(II) chloride In tetrahydrofuran at 20℃; for 1h; Schlenk technique; Stage #2: (E)-(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl 4-(tert-butyldimethylsilyl)-2-((4-methoxyphenyl)imino)but-3-ynoate In tetrahydrofuran at -78℃; for 0.0833333h; Schlenk technique; diastereoselective reaction;

94%

potassium iodomethyltrifluoroborate + 3-butenylmagnesium chloride (56039-93-1) → potassium 1-propenyltrifluoroborate

Conditions	Yield
In tetrahydrofuran at -25 - 0℃;	85%

3-butenylmagnesium chloride (56039-93-1) + isobutyraldehyde (78-84-2) → 2,9-dimethyl-dec-5-ene-3,8-diol

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: isobutyraldehyde In diethyl ether at -50 - -30℃; for 1h; Further stages.;	85%

3-butenylmagnesium chloride (56039-93-1) + tert-butyl (2S)-5-bromo-2-(methoxyacetyl)indoline-1-carboxylate (500548-54-9) → (S)-5-Bromo-2-((S)-1-hydroxy-1-methoxymethyl-pent-4-enyl)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester + tert-butyl (2S)-5-bromo-2-[(1R)-1-hydroxy-1-(methoxymethyl)-pent-4-enyl]-indoline-1-carboxylate (849479-96-5)

Conditions	Yield
In tetrahydrofuran at -78℃; for 0.25h; Grignard addition;	A n/a B 82%

pentanal (110-62-3) + 3-butenylmagnesium chloride (56039-93-1) → tetradec-7-ene-5,10-diol

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: pentanal In diethyl ether at -50 - -30℃; Further stages.;	82%

3,4,6-tri-O-benzyl-D-glucal epoxide (74372-90-0) + 3-butenylmagnesium chloride (56039-93-1) → (3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-but-3-enyl-tetrahydro-pyran-3-ol

Conditions	Yield
at -60 - 0℃;	80%

chloro(cyclopentadienyl)(triphenylphosphine)nickel(II) + 3-butenylmagnesium chloride (56039-93-1) → C5H5Ni(P(C6H5)3)CH2CH2CHCH2

Conditions	Yield
In diethyl ether; water; benzene C5H5Ni(P(C6H5)3)Cl in C6H6; added to a cooled soln. of CH2CH2CHCH2MgCl in ether; hydrolysis with aq. soln. of NH4Cl; purifn. of org. phase by chromy. on Al2O3; eluted with C6H6/hexane; crystd. by cooling and addn. of n-hexane;	80%
In diethyl ether; water; benzene C5H5Ni(P(C6H5)3)Cl in C6H6; added to a cooled soln. of CH2CH2CHCH2MgCl in ether; hydrolysis with aq. soln. of NH4Cl; purifn. of org. phase by chromy. on Al2O3; eluted with C6H6/hexane; crystd. by cooling and addn. of n-hexane;	80%

Isobutyronitrile (78-82-0) + 3-butenylmagnesium chloride (56039-93-1) → 2-methyl-hept-5-en-3-one (77958-21-5)

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: Isobutyronitrile In diethyl ether at -50 - -30℃; for 1h; Further stages.;	79%

cyclohexanone (108-94-1) + 3-butenylmagnesium chloride (56039-93-1) → 1-[4-(1-hydroxy-cyclohexyl)-but-2-enyl]-cyclohexanol

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: cyclohexanone In diethyl ether at -50 - -30℃; Further stages.;	78%

3-butenylmagnesium chloride (56039-93-1) + cyclopentanone (120-92-3) → 1-[4-(1-hydroxy-cyclopentyl)-but-2-enyl]-cyclopentanol

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: cyclopentanone In diethyl ether at -50 - -30℃; Further stages.;	78%

3-butenylmagnesium chloride (56039-93-1) + cyclopentanone (120-92-3) + propiononitrile (107-12-0) → 7-(1-hydroxy-cyclopentyl)-hept-5-en-3-one

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: propiononitrile In diethyl ether at -50 - -30℃; for 1h; Stage #3: cyclopentanone In diethyl ether at -30 - -10℃; for 1h; Further stages.;	76%

3-butenylmagnesium chloride (56039-93-1) + propiononitrile (107-12-0) → hept-5-en-3-one (63407-93-2)

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: propiononitrile In diethyl ether at -50 - -30℃; for 1h; Further stages.;	76%

4,4-dimethyl-1-cyclopentene-1-carboxaldehyde (38312-94-6) + 3-butenylmagnesium chloride (56039-93-1) → 1-(4,4-dimethylcyclopent-1-en-1-yl)pent-4-en-1-ol

Conditions	Yield
In tetrahydrofuran at 0℃; for 0.666667h; Inert atmosphere;	75%

(R)-(–)-2-(((tert-butyldimethylsilyl)oxy)methyl)-2,6-dimethylhept-5-enal (160661-42-7) + 3-butenylmagnesium chloride (56039-93-1) + propargyl bromide (106-96-7) → (2R)-2-methyl-2-(4-methylpent-3-en-1-yl)dec-9-en-4-yne-1,3-diol

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride; propargyl bromide In tetrahydrofuran at 0 - 20℃; for 5h; Inert atmosphere; Stage #2: (R)-(–)-2-(((tert-butyldimethylsilyl)oxy)methyl)-2,6-dimethylhept-5-enal In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; Stage #3: With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	75%

2-(methoxymethyl)-6-methylaniline (1035570-51-4) + 3-butenylmagnesium chloride (56039-93-1) → 2-(but-3-en-1-yl)-6-methylaniline (1035570-56-9)

Conditions	Yield
In tetrahydrofuran at 0 - 25℃; for 12h; Inert atmosphere;	75%

2-(4-ethyl-2-fluoro-phenylamino)-3,4-difluoro-N-methoxy-N-methyl-benzamide (833452-10-1) + 3-butenylmagnesium chloride (56039-93-1) → 1-[2-(4-ethyl-2-fluoro-phenylamino)-3,4-difluoro-phenyl]-pent-4-en-1-one

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.5h;	70%

C14H22N2O2 + 3-butenylmagnesium chloride (56039-93-1) → 8-methyl-6-(phenylamino)non-1-en-5-one

Conditions	Yield
With sodium carbonate In tetrahydrofuran at -20℃;	68%

6-Methyl-hept-5-en-2-on (110-93-0) + 3-butenylmagnesium chloride (56039-93-1) → 2,6,11,15-tetramethyl-hexadeca-2,8,14-triene-6,11-diol

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: 6-Methyl-hept-5-en-2-on In diethyl ether at -50 - -30℃; Further stages.;	67%

3-butenylmagnesium chloride (56039-93-1) + acetone (67-64-1) → 2,7-dimethyl-oct-4-ene-2,7-diol

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: acetone In diethyl ether at -50 - -30℃; Further stages.;	63%

propionaldehyde (123-38-6) + 3-butenylmagnesium chloride (56039-93-1) + propiononitrile (107-12-0) → 8-hydroxy-dec-5-en-3-one

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: propiononitrile In diethyl ether at -50 - -30℃; for 1h; Stage #3: propionaldehyde In diethyl ether at -30 - -10℃; for 1h; Further stages.;	60%

3,3-dimethyl acrylaldehyde (107-86-8) + 3-butenylmagnesium chloride (56039-93-1) → 2,11-dimethyl-dodeca-2,6,10-triene-4,9-diol

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: 3,3-dimethyl acrylaldehyde In diethyl ether at -50 - -30℃; Further stages.;	57%

methyl vinyl ketone (78-94-4) + 3-butenylmagnesium chloride (56039-93-1) → 3,8-dimethyl-deca-1,5,9-triene-3,8-diol

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: methyl vinyl ketone In diethyl ether at -50 - -30℃; Further stages.;	54%

methyl vinyl ketone (78-94-4) + 3-butenylmagnesium chloride (56039-93-1) + propiononitrile (107-12-0) → 8-hydroxy-8-methyl-deca-5,9-dien-3-one

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: propiononitrile In diethyl ether at -50 - -30℃; for 1h; Stage #3: methyl vinyl ketone In diethyl ether at -30 - -10℃; for 1h; Further stages.;	53%

C18H16ClN5O (858523-33-8) + 3-butenylmagnesium chloride (56039-93-1) → C22H23N5O

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; iron(III) acetylacetonate In tetrahydrofuran at 20℃; for 3h;	48%

(1R,4R)-(+)-bicyclo<2.2.2>oct-5-en-2-one (16196-15-9) + 3-butenylmagnesium chloride (56039-93-1) → C12H18O + C12H18O

Conditions	Yield
In tetrahydrofuran at -78 - 20℃; for 12h; diastereoselective reaction;	A 45% B 15%

3-butenylmagnesium chloride (56039-93-1) + propiononitrile (107-12-0) → dec-5-ene-3,8-dione

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: propiononitrile In diethyl ether at -50 - 35℃; for 4h; Further stages.;	33%

2,5-hexanedione (110-13-4) + 3-butenylmagnesium chloride (56039-93-1) → (1S*,2S*,4R*)-1,4-dimethyl-2-vinyl-cyclohexane-1,4-diol

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: 2,5-hexanedione In diethyl ether at -50 - -30℃; Further stages.;	30%

3-butenylmagnesium chloride (56039-93-1) + acetophenone (98-86-2) → (Z)-2,7-Diphenyl-oct-4-ene-2,7-diol

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: acetophenone In diethyl ether at -50 - -30℃; Further stages.;	30%

2-(4-ethynyl-2-fluoro-phenylamino)-3,4-difluoro-N-methoxy-N-methyl-benzamide (833451-95-9) + 3-butenylmagnesium chloride (56039-93-1) → 1-(2-(4-ethynyl-2-fluoro-phenylamino)-3,4-difluoro-phenyl)-pent-4-en-1-one

Conditions	Yield
Stage #1: 2-(4-ethynyl-2-fluoro-phenylamino)-3,4-difluoro-N-methoxy-N-methyl-benzamide; 3-butenylmagnesium chloride In tetrahydrofuran at -78℃; for 0.5h; Stage #2: With ammonium chloride In tetrahydrofuran at 20℃;	27%

(4,4-dimethyl-4-silacyclopent-1-en-1-yl)methanol + 3-butenylmagnesium chloride (56039-93-1) → 1-(4,4-dimethyl-4-silacyclopent-1-en-1-yl)pent-4-en-1-ol

Conditions	Yield
Stage #1: (4,4-dimethyl-4-silacyclopent-1-en-1-yl)methanol With aluminum tri-sec-butoxide; acetic acid In tert-butyl methyl ether at 0℃; for 0.166667h; Inert atmosphere; Stage #2: With 4-nitrobenzaldehdye In tert-butyl methyl ether at 20℃; for 2h; Inert atmosphere; Stage #3: 3-butenylmagnesium chloride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;	21%

Downstream Products

• 33558-80-4 (but-3-enyl)(chloromethyl)dimethylsilane 
• 903594-23-0 1-[5-chloro-2-(4-methoxy-benzylamino)-phenyl]-pent-4-en-1-one 
• 944284-25-7 (1,3-bis(diphenylphosphino)propane)bis(1-pentenyl)platinum(II) 
• 1008519-04-7 (1,2-bis(diphenylphosphino)ethane)bis(1-pentenyl)platinum(II) 
• 69393-37-9 2-(4'-Pentenoyl)imidazol 
• 1035570-56-9 2-(but-3-en-1-yl)-6-methylaniline