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761206

Sigma-Aldrich

4-Pentenylmagnesium bromide solution

0.5 M in THF

Synonym(s):

4-Pentene-1-magnesium bromide solution

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About This Item

Empirical Formula (Hill Notation):
C5H9BrMg
Molecular Weight:
173.33
MDL number:
MFCD11553331
UNSPSC Code:
12352302
PubChem Substance ID:
329766914
NACRES:
NA.22

form

solution

reaction suitability

reaction type: Grignard Reaction

concentration

0.5 M in THF

density

0.940 g/mL at 25 °C

SMILES string

Br[Mg]CCCC=C

InChI

1S/C5H9.BrH.Mg/c1-3-5-4-2;;/h3H,1-2,4-5H2;1H;/q;;+1/p-1

InChI key

LHTUYNSQNJOCCB-UHFFFAOYSA-M

Application

4-Pentenylmagnesium bromide is a general Grignard reagent used in the total synthesis of (−)-sarain A, (−)-salicylihalamide A and (+)-erysotramidine. It is also used in the synthesis of hexa-peri-hexabenzocoronene cyclophane.

Signal Word

Danger

Hazard Classifications

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

Target Organs

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)

11.8 °F - closed cup

Flash Point(C)

-11.2 °C - closed cup

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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Sigma-Aldrich

331376

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Total synthesis of (−)-Sarain A.
Becker M H, et al.
Journal of the American Chemical Society, 129(39), 11987-12002 (2007)
Total synthesis of (−)-salicylihalamide A and related congeners.
Smith III A B, et al.
Tetrahedron, 58(32), 6455-6471 (2002)
New approaches for the synthesis of erythrinan alkaloids.
Zhang F, et al.
Organic & Biomolecular Chemistry, 7(9), 1963-1979 (2009)
A Hexa-peri-hexabenzocoronene Cyclophane: An Addition to the Toolbox for Molecular Electronics.
Watson M D, et al.
Journal of the American Chemical Society, 126(5), 1402-1407 (2004)

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