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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 3: Spontaneously combustible substances and water- reactive materials
Materials containing Organometallic compounds
Hazardous rank I
1st spontaneously combustible materials and water reactive materials

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

254363-20L:
254363-100ML:4548173125152
254363-18L:4548173125169
254363-PZ:
254363-800ML:4548173125176
254363-BULK:
254363-500ML:
254363-VAR:
254363-8L:4548173125183

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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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