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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.

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  • 676-58-4 Structure
  • Basic information

    1. Product Name: Methylmagnesium chloride
    2. 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
    3. CAS NO:676-58-4
    4. Molecular Formula: CH3ClMg
    5. Molecular Weight: 74.79
    6. EINECS: 211-629-7
    7. Product Categories: Organometallics;GRIGNARD REAGENTS;AlkylChemical Synthesis;Grignard Reagents;Organic Bases;Organometallic Reagents;Synthetic Reagents;grignard reagent
    8. Mol File: 676-58-4.mol
    9. Article Data: 8
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 66 °C
    3. Flash Point: −1 °F
    4. Appearance: Pale brown to dark green/Liquid
    5. Density: 1.013 g/mL at 25 °C
    6. Refractive Index: N/A
    7. Storage Temp.: Flammables + water-Freezer (-20°C)e area
    8. Solubility: Miscible with diethyl ether and tetrahydrofuran.
    9. Water Solubility: reacts
    10. Sensitive: Air & Moisture Sensitive
    11. BRN: 3587199
    12. CAS DataBase Reference: Methylmagnesium chloride(CAS DataBase Reference)
    13. NIST Chemistry Reference: Methylmagnesium chloride(676-58-4)
    14. EPA Substance Registry System: Methylmagnesium chloride(676-58-4)
  • Safety Data

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

676-58-4 Usage

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.

Check Digit Verification of cas no

The CAS Registry Mumber 676-58-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,7 and 6 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 676-58:
(5*6)+(4*7)+(3*6)+(2*5)+(1*8)=94
94 % 10 = 4
So 676-58-4 is a valid CAS Registry Number.
InChI:InChI=1/CH3.ClH.Mg/h1H3;1H;/q;;+1/p-1/rCH3Mg.ClH/c1-2;/h1H3;1H/q+1;/p-1

676-58-4 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • Alfa Aesar

  • (42101)  Methylmagnesium chloride, 3M in THF, packaged under Argon in resealable ChemSeal? bottles   

  • 676-58-4

  • 0.25mole

  • 578.0CNY

  • Detail
  • Alfa Aesar

  • (42101)  Methylmagnesium chloride, 3M in THF, packaged under Argon in resealable ChemSeal? bottles   

  • 676-58-4

  • 1mole

  • 1519.0CNY

  • Detail
  • Alfa Aesar

  • (46118)  Methylmagnesium chloride, 3M in THF   

  • 676-58-4

  • 0.25mole

  • 381.0CNY

  • Detail
  • Alfa Aesar

  • (46118)  Methylmagnesium chloride, 3M in THF   

  • 676-58-4

  • 1mole

  • 1257.0CNY

  • Detail
  • Aldrich

  • (189901)  Methylmagnesiumchloridesolution  3.0 M in THF

  • 676-58-4

  • 189901-100ML

  • 423.54CNY

  • Detail
  • Aldrich

  • (189901)  Methylmagnesiumchloridesolution  3.0 M in THF

  • 676-58-4

  • 189901-4X25ML

  • 634.14CNY

  • Detail
  • Aldrich

  • (189901)  Methylmagnesiumchloridesolution  3.0 M in THF

  • 676-58-4

  • 189901-800ML

  • 1,623.96CNY

  • Detail
  • Aldrich

  • (189901)  Methylmagnesiumchloridesolution  3.0 M in THF

  • 676-58-4

  • 189901-18L-KL

  • 20,053.80CNY

  • Detail

676-58-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name methylmagnesium chloride

1.2 Other means of identification

Product number -
Other names Methylmagnesium chloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:676-58-4 SDS

676-58-4Synthetic route

methylene chloride
74-87-3

methylene chloride

methylmagnesium chloride
676-58-4

methylmagnesium chloride

Conditions
ConditionsYield
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

methylene chloride

magnesium

magnesium

methylmagnesium chloride
676-58-4

methylmagnesium chloride

Conditions
ConditionsYield
With diethyl ether
methylmagnesium chloride
676-58-4

methylmagnesium chloride

heptan-3-one
106-35-4

heptan-3-one

3-methyl-3-heptanol
5582-82-1

3-methyl-3-heptanol

Conditions
ConditionsYield
In diethyl ether at 0 - 20℃;100%
8-bromo-2-tetralone
117294-21-0

8-bromo-2-tetralone

methylmagnesium chloride
676-58-4

methylmagnesium chloride

8-bromo-2-hydroxy-2-methyl-1,2,3,4-tetrahydronaphthalene
127810-66-6

8-bromo-2-hydroxy-2-methyl-1,2,3,4-tetrahydronaphthalene

Conditions
ConditionsYield
With titanium tetrachloride In tetrahydrofuran; dichloromethane at 0℃; for 2h;100%
methylmagnesium chloride
676-58-4

methylmagnesium chloride

methyl 6-<2-(7-acetamidoheptyl)-1,3-dioxolan-2-yl>hexanoate
119947-11-4

methyl 6-<2-(7-acetamidoheptyl)-1,3-dioxolan-2-yl>hexanoate

N-<7-<2-(6-hydroxy-6-methylheptyl)-1,3-dioxolan-2-yl>heptyl>acetamide
119947-12-5

N-<7-<2-(6-hydroxy-6-methylheptyl)-1,3-dioxolan-2-yl>heptyl>acetamide

Conditions
ConditionsYield
In tetrahydrofuran for 12h;100%
methylmagnesium chloride
676-58-4

methylmagnesium chloride

dimethyl (RS)-6,6'-dibromobiphenyl-2,2'-dicarboxylate
156749-48-3

dimethyl (RS)-6,6'-dibromobiphenyl-2,2'-dicarboxylate

6,6'-dibromobiphenyl-2,2'-di(1-methylethanol)
156749-47-2

6,6'-dibromobiphenyl-2,2'-di(1-methylethanol)

Conditions
ConditionsYield
In tetrahydrofuran for 3h; Heating;100%
methylmagnesium chloride
676-58-4

methylmagnesium chloride

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-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

2,2-Dimethyl-propionic acid (2S,3S)-4-hydroxy-2,4-dimethyl-6-(tetrahydro-pyran-2-yl)-3-(2-trimethylsilanyl-ethoxymethoxy)-hexyl ester

Conditions
ConditionsYield
In tetrahydrofuran100%
methylmagnesium chloride
676-58-4

methylmagnesium chloride

3-(6',6'-dimethyl-2'-methylenecyclohexyl)propan-1-al
76337-22-9

3-(6',6'-dimethyl-2'-methylenecyclohexyl)propan-1-al

4-(6',6'-dimethyl-2'-methylenecyclohexyl)butan-2-ol
13720-13-3

4-(6',6'-dimethyl-2'-methylenecyclohexyl)butan-2-ol

Conditions
ConditionsYield
100%
methylmagnesium chloride
676-58-4

methylmagnesium chloride

C6H4(CH2CH2C(O)O)
119-84-6

C6H4(CH2CH2C(O)O)

4-(2-hydroxyphenyl)-2-methyl-2-butanol
4167-73-1

4-(2-hydroxyphenyl)-2-methyl-2-butanol

Conditions
ConditionsYield
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

methylmagnesium chloride

(3R,5R)-3,5-Bis-benzyloxy-2,2,6,6-tetramethyl-heptanedial

(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

(4SR,6SR)-4,6-bis(benzyloxy)-3,3,7,7-tetramethylnonane-2,8-diol

Conditions
ConditionsYield
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

phenyl(tetrahydro-2H-pyran-2-yl)methanone

methylmagnesium chloride
676-58-4

methylmagnesium chloride

(R*,S*)-2-(1'-hydroxy-1'-phenyl)ethyloxane

(R*,S*)-2-(1'-hydroxy-1'-phenyl)ethyloxane

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at 20℃; for 2h; Addition;100%
methylmagnesium chloride
676-58-4

methylmagnesium chloride

8-(tert-butyl-dimethyl-silanyloxy)-8-imidazol-1-yl-octan-2-one
410097-80-2

8-(tert-butyl-dimethyl-silanyloxy)-8-imidazol-1-yl-octan-2-one

8-(tert-butyl-dimethyl-silanyloxy)-8-imidazol-1-yl-2-methyl-octan-2-ol
410097-88-0

8-(tert-butyl-dimethyl-silanyloxy)-8-imidazol-1-yl-2-methyl-octan-2-ol

Conditions
ConditionsYield
In tetrahydrofuran100%
methylmagnesium chloride
676-58-4

methylmagnesium chloride

(+)-(3aR,4R,6aS)-4-tert-butoxymethyl-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one
479041-69-5

(+)-(3aR,4R,6aS)-4-tert-butoxymethyl-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one

((1S,4S,5R)-5-tert-Butoxymethyl-4-methyl-cyclopent-2-enyl)-acetic acid
479041-70-8

((1S,4S,5R)-5-tert-Butoxymethyl-4-methyl-cyclopent-2-enyl)-acetic acid

Conditions
ConditionsYield
With copper(I) bromide dimethylsulfide complex In tetrahydrofuran100%
methylmagnesium chloride
676-58-4

methylmagnesium chloride

(+/-)-(3aR,4R,6aS)-4-tert-butoxymethyl-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one

(+/-)-(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

((1R,4R,5S)-5-tert-Butoxymethyl-4-methyl-cyclopent-2-enyl)-acetic acid

Conditions
ConditionsYield
With copper(I) bromide dimethylsulfide complex In tetrahydrofuran100%
4,4-dimethoxy-5,6-dihydro-2H-pyran-3(4H)-one
693245-80-6

4,4-dimethoxy-5,6-dihydro-2H-pyran-3(4H)-one

methylmagnesium chloride
676-58-4

methylmagnesium chloride

C8H16O4
693248-63-4

C8H16O4

Conditions
ConditionsYield
In diethyl ether at 0℃; for 3h;100%
isovanillin
621-59-0

isovanillin

methylmagnesium chloride
676-58-4

methylmagnesium chloride

3-(α-hydroxyethyl)-6-methoxyphenol
29866-05-5

3-(α-hydroxyethyl)-6-methoxyphenol

Conditions
ConditionsYield
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

[3-(2-ethoxy-2-oxoethyl)phenyl]acetic acid

methylmagnesium chloride
676-58-4

methylmagnesium chloride

2-[3-(2-hydroxy-2-methylpropyl)phenyl]acetic acid
808768-96-9

2-[3-(2-hydroxy-2-methylpropyl)phenyl]acetic acid

Conditions
ConditionsYield
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

N-(4-acetyl-3-methoxyphenyl)acetamide

methylmagnesium chloride
676-58-4

methylmagnesium chloride

N-[4-(1-Hydroxy-1-methyl-ethyl)-3-methoxy-phenyl]-acetamide
865306-00-9

N-[4-(1-Hydroxy-1-methyl-ethyl)-3-methoxy-phenyl]-acetamide

Conditions
ConditionsYield
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

1-(3-chlorophenyl)-1H-pyrazole-4-carbaldehyde

methylmagnesium chloride
676-58-4

methylmagnesium chloride

1-[1-(3-chlorophenyl)-1H-pyrazol-4-yl]ethanol
863609-08-9

1-[1-(3-chlorophenyl)-1H-pyrazol-4-yl]ethanol

Conditions
ConditionsYield
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

methylmagnesium chloride

2-(3-chloro-phenyl)-2H-[1,2,3]triazole-4-carbaldehyde
41886-28-6

2-(3-chloro-phenyl)-2H-[1,2,3]triazole-4-carbaldehyde

1-[2-(3-chlorophenyl)-2H-1,2,3-triazol-4-yl]ethanol
863609-09-0

1-[2-(3-chlorophenyl)-2H-1,2,3-triazol-4-yl]ethanol

Conditions
ConditionsYield
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

3-Ethyl-N-methoxy-N-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole-6-carboxamide

methylmagnesium chloride
676-58-4

methylmagnesium chloride

1-(3-Ethyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazol-6-yl)ethanone
885132-76-3

1-(3-Ethyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazol-6-yl)ethanone

Conditions
ConditionsYield
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

N-methoxy-N-methylisoquinoline-1-carboxamide

methylmagnesium chloride
676-58-4

methylmagnesium chloride

1-acetylisoquinoline
58022-21-2

1-acetylisoquinoline

Conditions
ConditionsYield
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

3,7-dimethyl-2,6-octadienal

ammonium chloride

ammonium chloride

methylmagnesium chloride
676-58-4

methylmagnesium chloride

1-methylgeraniol
853065-81-3

1-methylgeraniol

Conditions
ConditionsYield
In hexane; tert-butyl methyl ether100%
(E)-N-butyl-1-(2-chloro-6-fluorophenyl)methanimine
945408-07-1

(E)-N-butyl-1-(2-chloro-6-fluorophenyl)methanimine

methylmagnesium chloride
676-58-4

methylmagnesium chloride

butyl-[1-(2-chloro-6-methyl-phenyl)-meth-(E)-ylidene]-amine
945408-08-2

butyl-[1-(2-chloro-6-methyl-phenyl)-meth-(E)-ylidene]-amine

Conditions
ConditionsYield
With manganese(ll) chloride In tetrahydrofuran at 0 - 40℃; for 0.5h;100%
methylmagnesium chloride
676-58-4

methylmagnesium chloride

(5-bromo-pentyl)-dimethyl tin (1+); bromide
61222-13-7

(5-bromo-pentyl)-dimethyl tin (1+); bromide

(5-bromo-pentyl)-trimethyl stannane
61222-07-9

(5-bromo-pentyl)-trimethyl stannane

Conditions
ConditionsYield
In diethyl ether100%
methylmagnesium chloride
676-58-4

methylmagnesium chloride

copper(l) chloride

copper(l) chloride

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

CH3Cu{P(OCH3)3}3

CH3Cu{P(OCH3)3}3

Conditions
ConditionsYield
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

methylmagnesium chloride

copper(l) chloride

copper(l) chloride

Mg(2+)*4Cu(1+)*6(CH3)(1-) = {(CH3)3Cu2}2Mg

Mg(2+)*4Cu(1+)*6(CH3)(1-) = {(CH3)3Cu2}2Mg

Conditions
ConditionsYield
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

methylmagnesium chloride

copper(l) chloride

copper(l) chloride

Mg(2+)*2{CH3CuCl}(1-) = Mg{CH3CuCl}2

Mg(2+)*2{CH3CuCl}(1-) = Mg{CH3CuCl}2

Conditions
ConditionsYield
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

Ti(η(5):η(1):η(1)-C5Me4SiMe2NCH2CH2OMe)Cl2

methylmagnesium chloride
676-58-4

methylmagnesium chloride

Ti(η(5):η(1)-C5Me4SiMe2NCH2CH2OMe)Me2
166987-98-0, 219947-10-1

Ti(η(5):η(1)-C5Me4SiMe2NCH2CH2OMe)Me2

Conditions
ConditionsYield
In not given100%
methylmagnesium chloride
676-58-4

methylmagnesium chloride

N-methoxy-N-methyl-3-(1-(tert-butoxycarbonyl)piperidin-4-yl)propionamide
301186-40-3

N-methoxy-N-methyl-3-(1-(tert-butoxycarbonyl)piperidin-4-yl)propionamide

tert-butyl 4-(3-oxobutyl)piperidine-1-carboxylate

tert-butyl 4-(3-oxobutyl)piperidine-1-carboxylate

Conditions
ConditionsYield
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

({2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-6-methyl-pyrimidin-4-yl}-methyl-amino)-acetic acid benzyl ester

methylmagnesium chloride
676-58-4

methylmagnesium chloride

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

1-({2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-6-methyl-pyrimidin-4-yl}-methyl-amino)-2-methyl-propan-2-ol

Conditions
ConditionsYield
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

3-(3-methoxypropoxy)-4-[(triisopropylsilyl)oxy]benzaldehyde

methylmagnesium chloride
676-58-4

methylmagnesium chloride

1-{3-(3-methoxypropoxy)-4-[(triisopropylsilyl)oxy]phenyl}ethanol
960409-28-3

1-{3-(3-methoxypropoxy)-4-[(triisopropylsilyl)oxy]phenyl}ethanol

Conditions
ConditionsYield
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%

676-58-4Upstream product

676-58-4Relevant articles and documents

Method for preparing 1, 1 and 1 -trifluoro -2 -methyl -2 - propanol

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Paragraph 0022; 0024; 0026; 0028; 0030; 0032; 0034; 0036; .., (2021/12/07)

The invention discloses a method for preparing 1, 1 and 1 -trifluoro -2 -methyl -2 - propanol. To the method, methyl magnesium halide Grignard reagent is prepared from halogenated methane as a raw material in ether solvents, 1, 1 and 1 - trifluoroacetone are reacted in the presence of a catalyst to obtain 1, 1, 1 -trifluoro -2 -methyl -2 -propanol. The method has the advantages of easily available raw materials, convenience in post-treatment and purification, simplicity in operation, relatively low cost, high yield and the like.

Chromium(II)-Catalyzed Diastereoselective and Chemoselective Csp2-Csp3 Cross-Couplings Using Organomagnesium Reagents

Li, Jie,Ren, Qianyi,Cheng, Xinyi,Karaghiosoff, Konstantin,Knochel, Paul

supporting information, p. 18127 - 18135 (2019/11/19)

A simple protocol for performing chromium-catalyzed highly diastereoselective alkylations of arylmagnesium halides with cyclohexyl iodides at ambient temperature has been developed. Furthermore, this ligand-free CrCl2 enables efficient electrophilic alkenylations of primary, secondary, and tetiary alkylmagnesium halides with readily available alkenyl acetates. Moreover, this chemoselective C-C coupling reaction with stereodefined alkenyl acetates proceeds in a stereoretentive fashion. A wide range of functional groups on alkyl iodides and alkenyl acetates are well tolerated, thus furnishing functionalized Csp2-Csp3 coupling products in good yields and high diastereoselectivity. Detailed mechanistic studies suggest that the in situ generated low-valent chromium(I) species might be the active catalyst for these Csp2-Csp3 cross-couplings.

ACID-LABILE ESTER MONOMER HAVING SPIROCYCLIC STRUCTURE, POLYMER, RESIST COMPOSITION, AND PATTERNING PROCESS

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, (2010/12/29)

An acid-labile ester monomer of spirocyclic structure has formula (1) wherein Z is a monovalent group having a polymerizable double bond, X is a divalent group which forms a cyclopentane, cyclohexane or norbornane ring, R2 is H or monovalent hydrocarbon, R3 and R4 are H or monovalent hydrocarbon, or R3 and R4, taken together, stand for a divalent group which forms a cyclopentane or cyclohexane ring, and n is 1 or 2. A polymer obtained from the acid-labile ester monomer has so high reactivity in acid-catalyzed elimination reaction that the polymer may be used to formulate a resist composition having high resolution.

Process for making α,β-unsaturated carboxylic acids

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, (2008/06/13)

α, β-Unsaturated acids of the formula STR1 wherein R1 signifies C1 -C5 -alkyl and Ar signifies an aryl group which is optionally substituted by one or more substituents selected from the group consisting of halogen, phenyl, C1 -C5 -alkyl, C1 -C5 -alkoxy, perfluorinated C1 -C5 -alkyl or perfluorinated C1 -C5 -alkoxy can be obtained from new or known compounds of the formula STR2 Compounds I can be converted by asymmetric hydrogenation into corresponding optically active saturated acids.

Chemical synthesis

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, (2008/06/13)

A process for the production of disubstituted bile acid analogs, including the disubstituted analogs of such bile acids as, lithocholic, hyodeoxycholic, cholic, chenodeoxycholic and ursodeoxycholic acids. This invention was made in the course of work performed under a grant from the U.S. National Heart Lung and Blood Institute.

A HIGHLY EFFICIENT SYNTHETIC ROUTE TO KETONES THROUGH SEQUENTIAL COUPLING REACTIONS OF GRIGNARD REAGENTS WITH S-PHENYL CARBONOCHLORODITHIOATE IN THE PRESENCE OF NICKEL OR IRON CATALYSTS

Cardellicchio, C.,Fiandanese, V.,Marchese, G.,Ronzini, L.

, p. 3595 - 3598 (2007/10/02)

The sequential coupling reactions of Grignard reagents with S-phenyl carbonochloridothioate in the presence of nickel(II) or iron(III) catalysts provides a very mild and straightforward route to symmetrical and unsymmetrical aliphatic and aromatic ketones.

IRON CATALYZED CROSS-COUPLING REACTIONS OF ACYL CHLORIDES WITH GRIGNARD REAGENTS. A MILD, GENERAL, AND CONVENIENT SYNTHESIS OF ALIPHATIC AND AROMATIC KETONES.

Fiandanese, V.,Marchese, G.,Martina, V.,Ronzini, L.

, p. 4805 - 4808 (2007/10/02)

Acyl chlorides couple with Grignard reagents at room temperature in the presence of catalytic amounts of tris(acetylacetonate)iron(III), Fe(acac)3.The reaction is general with respect to both reactants and provides a very mild and convenient method for the synthesis of aliphatic and aromatic ketones.

Infrared Matrix Isolation Study of Magnesium Metal Atom Reactions. Spectra of an Unsolvated Grignard Species

Ault, Bruce S.

, p. 3480 - 3484 (2007/10/02)

Reactions of magnesium atoms with methyl halides in argon matrices have given rise to four product bands which can be assigned to a new chemical species, at 543, 1305, 2800, and 2892 cm-1.All four are hydrogenic in nature, and are assigned to the four vibrations of a C3v methyl group in the reaction product.Evidence is presented for insertion of the magnesium atom into the carbon-halogen bond of the methyl halide to form a species H3CMgX, for X = Cl, Br, I.Similar reactions were observed with calcium and strontium atoms, while zinc atoms did not react with methylhalides under these conditions.No evidence was detected for a strong polar covalent carbon-magnesium bond, suggesting that the unsolvated Grignard reagent formed here has a structure other than that of the solvated solution species.

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