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419532

Sigma-Aldrich

2-Methylallylmagnesium chloride solution

0.5 M in THF

Synonym(s):

(2-Methyl-2-propenyl)magnesium chloride, Chloro(2-methyl-2-propenyl)magnesium, Chloro(2-methylallyl)magnesium, Methallylmagnesium chloride

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About This Item

Linear Formula:
H2C=C(CH3)CH2MgCl
CAS Number:
5674-01-1
Molecular Weight:
114.86
MDL number:
MFCD00674003
UNSPSC Code:
12352103
PubChem Substance ID:
24866258
NACRES:
NA.22

reaction suitability

reaction type: Grignard Reaction

Quality Level

100

concentration

0.5 M in THF

bp

65-67 °C

density

0.915 g/mL at 25 °C

SMILES string

CC(=C)C[Mg]Cl

InChI

1S/C4H7.ClH.Mg/c1-4(2)3;;/h1-2H2,3H3;1H;/q;;+1/p-1

InChI key

BJVFGWYBOLMUEM-UHFFFAOYSA-M

Application

2-Methylallylmagnesium chloride is a general Grignard reagent used in the synthesis of (−)-aplysin, acutumine, dimedol and allyldicyclopentadienyltitanium(III) complexes.

Packaging

The 25 mL Sure/Seal™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.

Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3 - Water-react 2

Target Organs

Respiratory 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)

-5.8 °F - closed cup

Flash Point(C)

-21 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The total synthesis of (−)-aplysin via a lithiation?borylation?propenylation sequence.
Fletcher C J, et al.
Tetrahedron, 68(37), 7598-7604 (2012)
Allyldicyclopentadienyltitanium (III) and (DI) methylallyl homologues.
Martin H A and Jellinek F
Journal of Organometallic Chemistry, 8(1), 115-128 (1967)
B List et al.
Proceedings of the National Academy of Sciences of the United States of America, 95(26), 15351-15355 (1998-12-23)
The synthesis of novel fluorogenic retro-aldol substrates for aldolase antibody 38C2 is described. These substrates are efficiently and specifically processed by antibody aldolases but not by natural cellular enzymes. Together, the fluorogenic substrates and antibody aldolases provide reporter gene systems
?Classical carbonyl reactivity enables a short synthesis of the core structure of acutumine?
Moreau.JR and Sorensen.JE
Tetrahedron, 63(28), 6446-6453 (2007)

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