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338257

Sigma-Aldrich

Isobutylmagnesium bromide solution

2.0 M in diethyl ether

Synonym(s):

iBuMgBr solution

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About This Item

Linear Formula:
(CH3)2CHCH2MgBr
CAS Number:
926-62-5
Molecular Weight:
161.32
MDL number:
MFCD00075126
UNSPSC Code:
12352103
PubChem Substance ID:
24860530
NACRES:
NA.22

form

liquid

reaction suitability

reaction type: Grignard Reaction

concentration

2.0 M in diethyl ether

density

0.941 g/mL at 25 °C

SMILES string

CC(C)C[Mg]Br

InChI

1S/C4H9.BrH.Mg/c1-4(2)3;;/h4H,1H2,2-3H3;1H;/q;;+1/p-1

InChI key

CMWBEISSZHZIMU-UHFFFAOYSA-M

Application

Isobutylmagnesium bromide (iBuMgBr) is a general Grignard reagent used in the total synthesis of (+)-rishirilide B, glucolipsin A, and (+)-juvabione. It can also be used as a reagent in the synthesis of pyrrolidine-based influenza neuraminidase (NA) inhibitors.

Signal Word

Danger

Hazard Statements

H224,H302,H315,H318,H336

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Central nervous system

Supplementary Hazards

EUH019

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

-29.2 °F - closed cup

Flash Point(C)

-34 °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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Enantio-and diastereocontrolled synthesis of (+)-juvabione employing organocatalytic desymmetrisation and photoinduced fragmentation.
Itagaki N and Iwabuchi Y
Chemical Communications (Cambridge, England), 69(11), 1175-1176 (2007)
Total synthesis of (+)-rishirilide B: Development and application of general processes for enantioselective oxidative dearomatization of resorcinol derivatives.
Mejorado LH and Pettus TRR
Journal of the American Chemical Society, 128(49), 15625-15631 (2006)
Structure-based characterization and optimization of novel hydrophobic binding interactions in a series of pyrrolidine influenza neuraminidase inhibitors.
Maring CJ, et al.
Journal of Medicinal Chemistry, 48(12), 3980-3990 (2005)
Structure assignment, total synthesis, and evaluation of the phosphatase modulating activity of glucolipsin A.
Furstner A, et al.
The Journal of Organic Chemistry, 69(2), 459-467 (2004)

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