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254363

Sigma-Aldrich

Methylmagnesium iodide solution

3.0 M in diethyl ether

Sinónimos:

Iodomethylmagnesium, Methylmagnesium iodine

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About This Item

Fórmula lineal:
CH3MgI
Número de CAS:
917-64-6
Peso molecular:
166.24
Beilstein/REAXYS Number:
1209226
MDL number:
MFCD00001026
UNSPSC Code:
12352103
PubChem Substance ID:
24855379
NACRES:
NA.22

Quality Level

200

reaction suitability

reaction type: Grignard Reaction

concentration

3.0 M in diethyl ether

density

1.261 g/mL at 25 °C

SMILES string

C[Mg]I

InChI

1S/CH3.HI.Mg/h1H3;1H;/q;;+1/p-1

InChI key

AUPXBVDHVRZMIB-UHFFFAOYSA-M

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Application

Methylmagnesium iodide solution can be used:
  • To prepare cis-1,2-dialkylcyclopropanols by treating with titanium(IV) alkoxide and carboxylic esters.
  • In stereospecific Ni catalyzed Kumada cross-coupling reactions of benzylic ethers.
  • To prepare 2,4-disubstituted selenochromenes by reacting with 1-benzoselenopyrylium salts.
  • In one of the key synthetic steps for the preparation of 7β-methyl-substituted 5-androstene derivatives from 3β-acetoxyandrost-5-en-17-one stereoselectively.

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Flam. Liq. 1 - Skin Corr. 1B - STOT SE 3 - Water-react 1

target_organs

Central nervous system

supp_hazards

EUH014,EUH019

Storage Class

4.3 - Hazardous materials which set free flammable gases upon contact with water

wgk_germany

WGK 3

flash_point_f

-40.0 °F - closed cup

flash_point_c

-40 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Sigma-Aldrich

67692

Iodomethane

Advanced Procedure for the Preparation of cis-1, 2-Dialkylcyclopropanols-Modified Ate Complex Mechanism for Titanium-Mediated Cyclopropanation of Carboxylic Esters with Grignard Reagents
Kulinkovich OG and Kananovich DG
European Journal of Organic Chemistry, 2007(13), 2121-2132 (2007)
Novel stereoselective synthesis of 7β -methyl-substituted 5-androstene derivatives
Zheng Y and Li Y
The Journal of Organic Chemistry, 68(4), 1603-1606 (2003)
Stereospecific nickel-catalyzed cross-coupling reactions of benzylic ethers with isotopically-labeled grignard reagents
Dawson DD and Jarvo ER
Organic Process Research & Development, 19(10), 1356-1359 (2015)
Reaction of 1-benzoselenopyrylium salts with grignard reagents: Formation of 2, 4-disubstituted selenochromenes and their conversion into the corresponding 1-benzoselenopyrylium salts
Sashida H, et al.
Journal of Heterocyclic Chemistry, 39(2), 405-409 (2002)

Artículos

Reagents for C–C Bond Formation

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