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526797

Sigma-Aldrich

Cyclopropylmagnesium bromide solution

0.5 M in THF

Synonym(s):

Bromocyclopropylmagnesium

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100 ML
$306.36
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$2,050.00

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100 ML
$306.36
800 ML
$2,050.00

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

$306.36

List Price$333.00Save 8%
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Available to ship onApril 17, 2025Details

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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.[1] 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.[2]

signalword

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

supp_hazards

EUH019

Storage Class

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

wgk_germany

WGK 3

flash_point_f

1.0 °F - closed cup

flash_point_c

-17.22 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR9025
SHBP5250
SHBM4442
SHBK2630
SHBH9826

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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)
Cyclopropylboronic acid: synthesis and Suzuki cross-coupling reactions.
Wallace D, et al.
Tetrahedron, 43(39), 6987-6990 (2002)

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