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290998

Sigma-Aldrich

Pentylmagnesium bromide solution

2.0 M in diethyl ether

Synonym(s):

1-Pentylmagnesium bromide, n-Pentylmagnesium bromide, Amylmagnesium bromide, Bromopentylmagnesium

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About This Item

Linear Formula:
C5H11MgBr
CAS Number:
693-25-4
Molecular Weight:
175.35
MDL number:
MFCD00000045
UNSPSC Code:
12352001
PubChem Substance ID:
24857502
NACRES:
NA.22

Quality Level

100

reaction suitability

reaction type: Grignard Reaction

concentration

2.0 M in diethyl ether

density

0.947 g/mL at 25 °C

SMILES string

CCCCC[Mg]Br

InChI

1S/C5H11.BrH.Mg/c1-3-5-4-2;;/h1,3-5H2,2H3;1H;/q;;+1/p-1

InChI key

ZXWGTPYWPZGZPT-UHFFFAOYSA-M

Application

Pentylmagnesium bromide solution is a Grignard reagent that can be used in the preparation of:
  • Alkanes via Ni or Cu-catalyzed cross-coupling reaction with alkyl fluorides.
  • Hydroxypiperidinones via the addition-cyclization-deprotection process of aldimines.

It can also be used as a reagent to synthesize a key intermediate by olefin alkylation in the total synthesis of alkaloid, (+)-hyperaspine , and surface alkylation of H-terminated Si (111), by Si-C bond formation.

signalword

Danger

Hazard Classifications

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

target_organs

Central nervous system

supp_hazards

EUH014,EUH019

Storage Class

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

wgk_germany

WGK 3

flash_point_f

-40.0 °F - closed cup

flash_point_c

-40 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBP0467
SHBN5025
SHBM2063
SHBJ8937
SHBJ9345

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A six-step asymmetric synthesis of (+)-hyperaspine
Comins DL and Sahn JJ
Organic Letters, 7(23), 5227-5228 (2005)
Ronia Chung-Tin Sham et al.
Environment international, 137, 105567-105567 (2020-02-23)
The occurrence of triphenyltin (TPT) compounds, a highly toxic antifouling biocide, has been documented in marine environments and organisms all over the world. While some studies showed that marine mammals can be used as sentinel organisms to evaluate the pollution
Ni-or Cu-catalyzed cross-coupling reaction of alkyl fluorides with Grignard reagents
Terao J, et al.
Journal of the American Chemical Society, 125(19), 5646-5647 (2003)
Muhammad Waqar Ashraf et al.
Bulletin of environmental contamination and toxicology, 98(6), 811-816 (2017-04-14)
In the present work, data on the levels of hazardous Organotin compounds in eight commercially important fish species, caught from Arabian Gulf, has been reported. Highest levels of tributyltin (TBT) (98.5 ng/g dry weight) were detected in Epinephelus Tauvina whereas minimum
Alkylation of Si surfaces using a two-step halogenation/Grignard route
Bansal A, et al.
Journal of the American Chemical Society, 118(30), 7225-7226 (1996)
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