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526797

Sigma-Aldrich

Cyclopropylmagnesium bromide solution

0.5 M in THF

Synonym(s):

Bromocyclopropylmagnesium

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About This Item

Empirical Formula (Hill Notation):
C3H5BrMg
CAS Number:
23719-80-4
Molecular Weight:
145.28
MDL number:
MFCD00672094
UNSPSC Code:
12352103
PubChem Substance ID:
24874579
NACRES:
NA.22

reaction suitability

reaction type: Grignard Reaction

concentration

0.5 M in THF

bp

65 °C

density

0.968 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

Br[Mg]C1CC1

InChI

1S/C3H5.BrH.Mg/c1-2-3-1;;/h1H,2-3H2;1H;/q;;+1/p-1

InChI key

QUPLLJGAJVXXBW-UHFFFAOYSA-M

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Application

Cyclopropylmagnesium bromide solution has been used in Grignard reaction that finds application as the key step in the preparation of aminopropylindenes, a chemotype of oxidosqualene cyclase (OSC) inhibitors from Grundmann′s ketone. It can react with trimethylborate to form cyclopropylboronic acid, which can undergo Suzuki-type coupling reactions with different aryl, and heteroaryl bromides to form the cyclopropyl adducts.

Signal Word

Danger

Hazard Classifications

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

Target Organs

Central nervous system, Respiratory 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)

1.0 °F - closed cup

Flash Point(C)

-17.22 °C - closed cup

Certificates of Analysis (COA)

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Cyclopropylboronic acid: synthesis and Suzuki cross-coupling reactions.
Wallace D, et al.
Tetrahedron, 43(39), 6987-6990 (2002)
Aminopropylindenes derived from Grundmann's ketone as a novel chemotype of oxidosqualene cyclase inhibitors.
Lange S, et al.
European Journal of Medicinal Chemistry, 63, 758-764 (2013)

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