676-58-4

Basic information

• Product Name: Methylmagnesium chloride
• Synonyms: chloromethyl-magnesiu;METHYLMAGNESIUM CHLORIDE;METHYLMAGNESIUM CHLORIDE, 2.5M SOLUTIONIN BUTYL DIGLYME;METHYLMAGNESIUM CHLORIDE, 3.0M SOLUTION IN TETRAHYDROFURAN;METHYLMAGNESIUM CHLORIDE SOLUTION, ~3 M IN THF;METHYLMAGNESIUM CHLORIDE, 3.0M SOLUTION;Methylmagnesium Chloride 1.5 M In Butyl Diglyme;Methylmagnesium Chloride 1.5 M in n-Butyl Ether
• CAS NO: 676-58-4
• Molecular Formula: CH₃ClMg
• Molecular Weight: 74.79
• EINECS: 211-629-7
• Product Categories: Organometallics;GRIGNARD REAGENTS;AlkylChemical Synthesis;Grignard Reagents;Organic Bases;Organometallic Reagents;Synthetic Reagents;grignard reagent
• Mol File: 676-58-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 66 °C
• Flash Point: −1 °F
• Appearance: Pale brown to dark green/Liquid
• Density: 1.013 g/mL at 25 °C
• Storage Temp.: Flammables + water-Freezer (-20°C)e area
• Solubility: Miscible with diethyl ether and tetrahydrofuran.
• Water Solubility: reacts
• Sensitive: Air & Moisture Sensitive
• BRN: 3587199
• CAS DataBase Reference: Methylmagnesium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Methylmagnesium chloride(676-58-4)
• EPA Substance Registry System: Methylmagnesium chloride(676-58-4)

Safety Data

• Hazard Codes: F,C
• Statements: 11-14/15-34-19-15-37-14
• Safety Statements: 26-30-36/37/39-43-45-7/8-33-29-16
• RIDADR: UN 3399 4.3/PG 2
• WGK Germany: 1
• F: 1-3-10
• TSCA: Yes
• HazardClass: 4.3
• PackingGroup: I
• Hazardous Substances Data: 676-58-4(Hazardous Substances Data)

Usage

Description

Methylmagnesium chloride is an organomagnesium compound with the chemical formula CH3MgCl. It is a highly reactive and flammable substance, often used in organic synthesis as a Grignard reagent.

Uses

Used in Organic Synthesis:
Methylmagnesium chloride is used as a Grignard reagent for various organic synthesis applications. It acts as a nucleophile and can react with a wide range of organic compounds, such as carbonyl compounds, to form new chemical bonds.
Used in Pharmaceutical Industry:
Methylmagnesium chloride is used as an alkylating agent in the synthesis of various pharmaceutical compounds. Its ability to transfer alkyl groups makes it a versatile reagent for the production of drugs and other bioactive molecules.
Used in Chemical Research:
Methylmagnesium chloride is also used in chemical research as a model compound to study the reactivity and properties of organomagnesium compounds. This helps in understanding the underlying mechanisms of various organic reactions and developing new synthetic methods.

Hazard

Flammable, dangerous fire and explosionrisk.

InChI:InChI=1/CH3.ClH.Mg/h1H3;1H;/q;;+1/p-1/rCH3Mg.ClH/c1-2;/h1H3;1H/q+1;/p-1

Synthetic route

methylene chloride (74-87-3) → methylmagnesium chloride (676-58-4)

Conditions	Yield
With magnesium In tetrahydrofuran
With magnesium In solid matrix at -258.2℃;
With magnesium; lithium chloride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;

methylene chloride (74-87-3) + magnesium → methylmagnesium chloride (676-58-4)

Conditions	Yield
With diethyl ether

methylmagnesium chloride (676-58-4) + heptan-3-one (106-35-4) → 3-methyl-3-heptanol (5582-82-1)

Conditions	Yield
In diethyl ether at 0 - 20℃;	100%

8-bromo-2-tetralone (117294-21-0) + methylmagnesium chloride (676-58-4) → 8-bromo-2-hydroxy-2-methyl-1,2,3,4-tetrahydronaphthalene (127810-66-6)

Conditions	Yield
With titanium tetrachloride In tetrahydrofuran; dichloromethane at 0℃; for 2h;	100%

methylmagnesium chloride (676-58-4) + methyl 6-<2-(7-acetamidoheptyl)-1,3-dioxolan-2-yl>hexanoate (119947-11-4) → N-<7-<2-(6-hydroxy-6-methylheptyl)-1,3-dioxolan-2-yl>heptyl>acetamide (119947-12-5)

Conditions	Yield
In tetrahydrofuran for 12h;	100%

methylmagnesium chloride (676-58-4) + dimethyl (RS)-6,6'-dibromobiphenyl-2,2'-dicarboxylate (156749-48-3) → 6,6'-dibromobiphenyl-2,2'-di(1-methylethanol) (156749-47-2)

Conditions	Yield
In tetrahydrofuran for 3h; Heating;	100%

methylmagnesium chloride (676-58-4) + 2,2-Dimethyl-propionic acid (2S,3S)-4-hydroxy-2-methyl-6-(tetrahydro-pyran-2-yl)-3-(2-trimethylsilanyl-ethoxymethoxy)-hexyl ester → 2,2-Dimethyl-propionic acid (2S,3S)-4-hydroxy-2,4-dimethyl-6-(tetrahydro-pyran-2-yl)-3-(2-trimethylsilanyl-ethoxymethoxy)-hexyl ester

Conditions	Yield
In tetrahydrofuran	100%

methylmagnesium chloride (676-58-4) + 3-(6',6'-dimethyl-2'-methylenecyclohexyl)propan-1-al (76337-22-9) → 4-(6',6'-dimethyl-2'-methylenecyclohexyl)butan-2-ol (13720-13-3)

Conditions	Yield
	100%

methylmagnesium chloride (676-58-4) + C6H4(CH2CH2C(O)O) (119-84-6) → 4-(2-hydroxyphenyl)-2-methyl-2-butanol (4167-73-1)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃;	100%
In tetrahydrofuran Ambient temperature;	6.25 g
In tetrahydrofuran; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water
Stage #1: methylmagnesium chloride; C6H4(CH2CH2C(O)O) In tetrahydrofuran for 18.6667h; Stage #2: With water In tetrahydrofuran Cooling;

methylmagnesium chloride (676-58-4) + (3R,5R)-3,5-Bis-benzyloxy-2,2,6,6-tetramethyl-heptanedial → (4SR,6SR)-4,6-bis(benzyloxy)-3,3,7,7-tetramethylnonane-2,8-diol

Conditions	Yield
In tetrahydrofuran at -20 - 20℃;	100%
at -20℃; for 0.0833333h; pH=13; Grignard reaction;

phenyl(tetrahydro-2H-pyran-2-yl)methanone (73504-72-0) + methylmagnesium chloride (676-58-4) → (R*,S*)-2-(1'-hydroxy-1'-phenyl)ethyloxane

Conditions	Yield
In tetrahydrofuran; diethyl ether at 20℃; for 2h; Addition;	100%

methylmagnesium chloride (676-58-4) + 8-(tert-butyl-dimethyl-silanyloxy)-8-imidazol-1-yl-octan-2-one (410097-80-2) → 8-(tert-butyl-dimethyl-silanyloxy)-8-imidazol-1-yl-2-methyl-octan-2-ol (410097-88-0)

Conditions	Yield
In tetrahydrofuran	100%

methylmagnesium chloride (676-58-4) + (+)-(3aR,4R,6aS)-4-tert-butoxymethyl-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one (479041-69-5) → ((1S,4S,5R)-5-tert-Butoxymethyl-4-methyl-cyclopent-2-enyl)-acetic acid (479041-70-8)

Conditions	Yield
With copper(I) bromide dimethylsulfide complex In tetrahydrofuran	100%

methylmagnesium chloride (676-58-4) + (+/-)-(3aR,4R,6aS)-4-tert-butoxymethyl-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one → ((1R,4R,5S)-5-tert-Butoxymethyl-4-methyl-cyclopent-2-enyl)-acetic acid

Conditions	Yield
With copper(I) bromide dimethylsulfide complex In tetrahydrofuran	100%

4,4-dimethoxy-5,6-dihydro-2H-pyran-3(4H)-one (693245-80-6) + methylmagnesium chloride (676-58-4) → C8H16O4 (693248-63-4)

Conditions	Yield
In diethyl ether at 0℃; for 3h;	100%

isovanillin (621-59-0) + methylmagnesium chloride (676-58-4) → 3-(α-hydroxyethyl)-6-methoxyphenol (29866-05-5)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 4.08333h;	100%
In tetrahydrofuran at 5 - 20℃; Grignard addition;	85%

[3-(2-ethoxy-2-oxoethyl)phenyl]acetic acid (113520-28-8) + methylmagnesium chloride (676-58-4) → 2-[3-(2-hydroxy-2-methylpropyl)phenyl]acetic acid (808768-96-9)

Conditions	Yield
Stage #1: [3-(2-ethoxy-2-oxoethyl)phenyl]acetic acid; methylmagnesium chloride In tetrahydrofuran at 0 - 20℃; Stage #2: With hydrogenchloride In tetrahydrofuran; water Product distribution / selectivity;	100%
Stage #1: [3-(2-ethoxy-2-oxoethyl)phenyl]acetic acid; methylmagnesium chloride In tetrahydrofuran at 0℃; for 18h; Stage #2: With hydrogenchloride; water In tetrahydrofuran	100%
In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	100%

N-(4-acetyl-3-methoxyphenyl)acetamide (51410-08-3) + methylmagnesium chloride (676-58-4) → N-[4-(1-Hydroxy-1-methyl-ethyl)-3-methoxy-phenyl]-acetamide (865306-00-9)

Conditions	Yield
Stage #1: N-(4-acetyl-3-methoxyphenyl)acetamide; methylmagnesium chloride In tetrahydrofuran at 0 - 20℃; for 2.91667h; Stage #2: With ammonium chloride In tetrahydrofuran	100%
In tetrahydrofuran at 0 - 20℃; for 1.91667h;	100%

1-(3-chlorophenyl)-1H-pyrazole-4-carbaldehyde (400877-26-1) + methylmagnesium chloride (676-58-4) → 1-[1-(3-chlorophenyl)-1H-pyrazol-4-yl]ethanol (863609-08-9)

Conditions	Yield
Stage #1: 1-(3-chlorophenyl)-1H-pyrazole-4-carbaldehyde; methylmagnesium chloride In tetrahydrofuran; diethyl ether at 0 - 20℃; for 2.25h; Stage #2: With water; ammonium chloride In tetrahydrofuran; diethyl ether	100%

methylmagnesium chloride (676-58-4) + 2-(3-chloro-phenyl)-2H-[1,2,3]triazole-4-carbaldehyde (41886-28-6) → 1-[2-(3-chlorophenyl)-2H-1,2,3-triazol-4-yl]ethanol (863609-09-0)

Conditions	Yield
Stage #1: methylmagnesium chloride; 2-(3-chloro-phenyl)-2H-[1,2,3]triazole-4-carbaldehyde In tetrahydrofuran; diethyl ether at 0 - 20℃; for 1.5h; Stage #2: With water; ammonium chloride In tetrahydrofuran; diethyl ether	100%

3-Ethyl-N-methoxy-N-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole-6-carboxamide (885132-75-2) + methylmagnesium chloride (676-58-4) → 1-(3-Ethyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazol-6-yl)ethanone (885132-76-3)

Conditions	Yield
In tetrahydrofuran at -78 - 20℃;	100%
Stage #1: 3-ethyl-N-methoxy-N-methyl-1-[(2-(trimethylsilyl)ethoxy)methyl]-1H-indazole-6-carboxamide; methylmagnesium chloride In tetrahydrofuran at -78 - 20℃; Stage #2: With water; ammonium chloride In tetrahydrofuran at 20℃;	100%

N-methoxy-N-methylisoquinoline-1-carboxamide (866328-99-6) + methylmagnesium chloride (676-58-4) → 1-acetylisoquinoline (58022-21-2)

Conditions	Yield
Stage #1: N-methoxy-N-methylisoquinoline-1-carboxamide; methylmagnesium chloride In tetrahydrofuran at 0℃; for 1.16667h; Stage #2: With water; ammonium chloride In tetrahydrofuran	100%

3,7-dimethyl-2,6-octadienal (141-27-5) + ammonium chloride + methylmagnesium chloride (676-58-4) → 1-methylgeraniol (853065-81-3)

Conditions	Yield
In hexane; tert-butyl methyl ether	100%

(E)-N-butyl-1-(2-chloro-6-fluorophenyl)methanimine (945408-07-1) + methylmagnesium chloride (676-58-4) → butyl-[1-(2-chloro-6-methyl-phenyl)-meth-(E)-ylidene]-amine (945408-08-2)

Conditions	Yield
With manganese(ll) chloride In tetrahydrofuran at 0 - 40℃; for 0.5h;	100%

methylmagnesium chloride (676-58-4) + (5-bromo-pentyl)-dimethyl tin (1+); bromide (61222-13-7) → (5-bromo-pentyl)-trimethyl stannane (61222-07-9)

Conditions	Yield
In diethyl ether	100%

methylmagnesium chloride (676-58-4) + copper(l) chloride + phosphorous acid trimethyl ester (121-45-9) → CH3Cu{P(OCH3)3}3

Conditions	Yield
In tetrahydrofuran under N2, MeMgCl reacted with CuCl, P(OMe)3 was added, stirred for 30 min at 0°C; not isolated;	100%

methylmagnesium chloride (676-58-4) + copper(l) chloride → Mg(2+)*4Cu(1+)*6(CH3)(1-) = {(CH3)3Cu2}2Mg

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran under N2, soln. of MeMgCl was added to a stirred suspn. of CuCl at -10°C (ratio MeMgCl/CuCl = 3/2), stirred for 30 min at 0°C; not isolated;	100%

methylmagnesium chloride (676-58-4) + copper(l) chloride → Mg(2+)*2{CH3CuCl}(1-) = Mg{CH3CuCl}2

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran under N2, soln. of MeMgCl was added to a stirred suspn. of CuCl at -10°C, HMPT was also added, stirred for 30 min at 0°C; not isolated;	100%

Ti(η(5):η(1):η(1)-C5Me4SiMe2NCH2CH2OMe)Cl2 (166987-94-6, 174898-32-9) + methylmagnesium chloride (676-58-4) → Ti(η(5):η(1)-C5Me4SiMe2NCH2CH2OMe)Me2 (166987-98-0, 219947-10-1)

Conditions	Yield
In not given	100%

methylmagnesium chloride (676-58-4) + N-methoxy-N-methyl-3-(1-(tert-butoxycarbonyl)piperidin-4-yl)propionamide (301186-40-3) → tert-butyl 4-(3-oxobutyl)piperidine-1-carboxylate

Conditions	Yield
Stage #1: methylmagnesium chloride; N-methoxy-N-methyl-3-(1-(tert-butoxycarbonyl)piperidin-4-yl)propionamide In tetrahydrofuran at 0 - 20℃; for 4h; Stage #2: With ammonium chloride In tetrahydrofuran; water for 0.166667h;	100%

({2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-6-methyl-pyrimidin-4-yl}-methyl-amino)-acetic acid benzyl ester (1185019-50-4) + methylmagnesium chloride (676-58-4) → 1-({2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-6-methyl-pyrimidin-4-yl}-methyl-amino)-2-methyl-propan-2-ol (1185015-50-2)

Conditions	Yield
Stage #1: ({2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-6-methyl-pyrimidin-4-yl}-methyl-amino)-acetic acid benzyl ester; methylmagnesium chloride In tetrahydrofuran at 20℃; for 2.16667h; Cooling with ice; Stage #2: With water In tetrahydrofuran Hydrolysis;	100%

3-(3-methoxypropoxy)-4-[(triisopropylsilyl)oxy]benzaldehyde (960409-26-1) + methylmagnesium chloride (676-58-4) → 1-{3-(3-methoxypropoxy)-4-[(triisopropylsilyl)oxy]phenyl}ethanol (960409-28-3)

Conditions	Yield
Stage #1: 3-(3-methoxypropoxy)-4-[(triisopropylsilyl)oxy]benzaldehyde; methylmagnesium chloride In tetrahydrofuran at 0 - 20℃; Stage #2: With water; ammonium chloride In tetrahydrofuran at 0℃;	100%

Upstream product

• 74-87-3 methylene chloride 

Downstream Products

• 1084-78-2 (1RS,2SR)-(+/-)-1,2-diphenyl-1,2-propandiol 
• 1084-78-2 (1RS,2RS)-(+/-)-1,2-diphenyl-1,2-propandiol 
• 19005-95-9 2,4,5-Trimethyl-3-acetyl-pyrrole 
• 2532-58-3 cis-1,3-dimethylcyclopentane 
• 1759-58-6 trans-1,3-dimethylcyclopentane 
• 75-77-4 chloro-trimethyl-silane 
• 629165-59-9 2-phenyl-4-piperidino-butan-2-ol 
• 594-82-1 tetramethyl-2,2,3,3 butane 
• 2344-80-1 Chloromethyltrimethylsilane 
• 75-83-2 2,2-Dimethylbutane 
• 690-37-9 2,4,4-trimethyl-2-pentanol 
• 463-82-1 2,2-dimethylpropane 
• 10545-34-3 3-(trimethylsilyl)propyl bromide 
• 18292-38-1 2-methallyltrimethylsilane 

Relevant articles and documents

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