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419613

Sigma-Aldrich

2-Methyl-1-propenylmagnesium bromide solution

0.5 M in THF

Synonym(s):

(2-Methylpropenyl)magnesium bromide, 2,2-Dimethylvinylmagnesium bromide, Isobutenylmagnesium bromide

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About This Item

Linear Formula:
(CH3)2C=CHMgBr
CAS Number:
38614-36-7
Molecular Weight:
159.31
MDL number:
MFCD00209600
UNSPSC Code:
12352103
PubChem Substance ID:
24866265
NACRES:
NA.22

Quality Level

100

reaction suitability

reaction type: Grignard Reaction

concentration

0.5 M in THF

density

0.952 g/mL at 25 °C

SMILES string

C\C(C)=C\[Mg]Br

InChI

1S/C4H7.BrH.Mg/c1-4(2)3;;/h1H,2-3H3;1H;/q;;+1/p-1

InChI key

BKVIQODYSREJQH-UHFFFAOYSA-M

Related Categories

General description

2-Methyl-1-propenylmagnesiumbromide is a heterocyclic organic compound. It is used as a Grignard reagent in chemical synthesis.

Application

Used in a study of a palladium-catalyzed coupling with aryl tosylates.
Used in a synthesis of (2S,3S)-3′-fluoroisoleucine.

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)

5.0 °F - closed cup

Flash Point(C)

-15 °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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Enantioselective Oxy-Heck--Matsuda Arylations: Expeditious Synthesis of Dihydrobenzofuran Systems and Total Synthesis of the Neolignan (-)-Conocarpan
Silva AR, et al.
advanced synthesis and catalysis, 360(2), 346-365 (2018)
Michael E Limmert et al.
The Journal of organic chemistry, 70(23), 9364-9370 (2005-11-05)
[Reaction: see text]. Aryl and alkenyl tosylates are easily prepared, inexpensive and, thus, attractive for transition-metal-catalyzed couplings, but their reactivity is low. We report examples of mild, palladium-catalyzed coupling of aryl, alkenyl, and alkyl Grignard reagents with aryl and alkenyl
Jean-Damien Charrier et al.
Organic & biomolecular chemistry, 2(5), 797-802 (2004-02-27)
The fluorinated amino acid, (2S,3S)-3'-fluoroisoleucine 3, has been synthesised by a route involving stereoselective cuprate or photochemical addition to the compound 4, derived in turn from (2S)-pyroglutamic acid. This provides a reporter group for the hydrophobic amino acid (2S)-isoleucine for

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