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254363

Sigma-Aldrich

Methylmagnesium iodide solution

3.0 M in diethyl ether

Synonym(s):

Iodomethylmagnesium, Methylmagnesium iodine

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About This Item

Linear Formula:
CH3MgI
CAS Number:
917-64-6
Molecular Weight:
166.24
Beilstein:
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.

Signal Word

Danger

Hazard Statements

H224,H260,H314,H336

Hazard Classifications

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

Target Organs

Central nervous system

Supplementary Hazards

EUH014,EUH019

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

-40.0 °F - closed cup

Flash Point(C)

-40 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBK9708
SHBH8848
SHBG5857V
12896BPV
12896BP

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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)

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