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419567

Sigma-Aldrich

Isopropenylmagnesium bromide solution

0.5 M in THF

Synonym(s):

1-Methylvinylmagnesium bromide, 1-Propen-2-ylmagnesium bromide, 2-Propen-2-ylmagnesium bromide, Bromo prop-1-en-2-yl magnesium, Bromo(isopropenylmagnesium), Isopropenylmagnesium bromide

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About This Item

Linear Formula:
CH2=C(CH3)MgBr
CAS Number:
13291-18-4
Molecular Weight:
145.28
Beilstein/REAXYS Number:
3587297
MDL number:
MFCD00192240
UNSPSC Code:
12352103
PubChem Substance ID:
24866260
EC Index Number:
603-688-6
NACRES:
NA.22

Quality Level

100

reaction suitability

reaction type: Grignard Reaction

concentration

0.5 M in THF

bp

67 °C

density

0.935 g/mL at 25 °C

SMILES string

CC(=C)[Mg]Br

InChI

1S/C3H5.BrH.Mg/c1-3-2;;/h1H2,2H3;1H;/q;;+1/p-1

InChI key

LFTYALBVGVNGLI-UHFFFAOYSA-M

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Application

Isopropenylmagnesium bromide (iPrMgBr) solution (0.5 M in THF) has been used in the Grignard reaction, a key step the in preparation of zofenoprilat and (S)-(−)-phosphonotrixin. It can also be used for the regioselective ring opening of an optically active epoxy alcohol in the total synthesis of (+)-desepoxyasperdiol.

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Danger

Hazard Classifications

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

target_organs

Central nervous system, Respiratory system

supp_hazards

EUH019

wgk_germany

WGK 3

flash_point_f

35.6 °F

flash_point_c

2 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Total synthesis of (+)-desepoxyasperdiol.
Tius M A and Fauq A H
Journal of the American Chemical Society, 108(5), 1035-1039 (1986)
Chemoenzymatic formal synthesis of (S)-(?)-phosphonotrixin.
Chenevert R, et al.
Tetrahedron Asymmetry, 15(12), 1889-1892 (2004)
11C-Radiosynthesis and preliminary human evaluation of the disposition of the ACE inhibitor [11C] zofenoprilat.
Matarrese M, et al.
Bioorganic & Medicinal Chemistry, 12(3), 603-611 (2004)

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