Skip to Content
Merck
All Photos(2)

Key Documents

View All Documentation

225754

Sigma-Aldrich

Allylmagnesium bromide solution

1.0 M in diethyl ether

Synonym(s):

(Prop-2-en-1-yl)magnesium bromide, 2-Propenylmagnesium bromide, Allyl magnesium bromide, Allylbromomagnesium, Allylmagnesiumbromide, Bromo-2-propenylmagnesium

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Linear Formula:
CH2=CHCH2MgBr
CAS Number:
1730-25-2
Molecular Weight:
145.28
Beilstein:
969335
MDL number:
MFCD00000044
UNSPSC Code:
12352103
PubChem Substance ID:
24853518
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

100

reaction suitability

reaction type: Grignard Reaction

concentration

1.0 M in diethyl ether

density

0.851 g/mL at 25 °C

SMILES string

Br[Mg]CC=C

InChI

1S/C3H5.BrH.Mg/c1-3-2;;/h3H,1-2H2;1H;/q;;+1/p-1

InChI key

FEMBXICCJNZMMC-UHFFFAOYSA-M

Looking for similar products? Visit Product Comparison Guide

Related Categories

General description

Allylmagnesium bromide solution serves as a selective nucleophile toward aza-aromatic heterocycles. [1]

Application

Allylmagnesium bromide solution can be used in the Grignard reaction, which is a key step to synthesize:
  • 2-(9,10-dihydro-9,10-propanoanthracen-9-yl)-N-methylethanamine (2), a homolog of benzoctamine [2]
  • tarchonanthuslactone[3]
  • (+)-preussin[4]
  • polyhydroxylated quinolizidine alkaloids[5]

Packaging

View returnable container options.

Signal Word

Danger

Hazard Statements

H224,H260,H302,H314,H336

Hazard Classifications

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

Target Organs

Central nervous system

Supplementary Hazards

EUH019

Storage Class Code

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

WGK

WGK 1

Flash Point(F)

-40.0 °F - closed cup

Flash Point(C)

-40 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SHBQ7020
SHBP1025
SHBM1555
SHBJ6101
SHBH8690

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

An Efficient Asymmetric Synthesis of Tarchonanthuslactone1.
Reddy M, et al.
The Journal of Organic Chemistry, 66(7), 2512-2514 (2001)
Stereoselective synthesis of the antifungal antibiotic (+)-preussin.
Veeresa G, et al.
Tetrahedron, 54(51), 15673-15678 (1998)
Synthesis of 2-(9, 10-dihydro-9, 10-propanoanthracen-9-yl)-N-methylethanamine via a [4+ 2] cycloaddition.
Karama U, et al.
Molecules (Basel), 15(6), 4201-4206 (2010)
Allylmagnesium Bromide as a selective nucleophile toward Aza-aromatic heterocycles
Henry G et al.
Journal of the American Chemical Society, 79, 1245-1249 (1957)
Synthesis of trihydroxy quinolizidine alkaloids: 1, 3-addition reaction of allylmagnesium bromide to a sugar nitrone.
Dhavale DD, et al.
Tetrahedron, 60(13), 3009-3016 (2004)

Questions

1–2 of 2 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service