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Sigma-Aldrich

Ethynylmagnesium bromide solution

0.5 M in THF

Synonym(s):

Acetylenemagnesium bromide, Bromoethynylmagnesium, Ethynylmagnesium bromide

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About This Item

Linear Formula:
HC≡CMgBr
CAS Number:
Molecular Weight:
129.24
Beilstein:
3600874
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
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Quality Level

reaction suitability

reaction type: Grignard Reaction

concentration

0.5 M in THF

density

0.94 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

Br[Mg]C#C

InChI

1S/C2H.BrH.Mg/c1-2;;/h1H;1H;/q;;+1/p-1

InChI key

HUGJUYPSXULVQQ-UHFFFAOYSA-M

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General description

Ethynylmagnesium bromide solution, also known as bromoethynylmagnesium, is a grignard reagent that is commonly used in the synthesis of polymers, and unsaturated phosphonites.[1] [2]

Application

Ethynylmagnesium bromide solution can be used in:
  • Grafting of aliphatic polymer. [3]
  • Synthesis of anthracene-containing species like 1,8-dichloro-10-(ethynyl)anthracene. [4]
  • The preparation of the alkyne component in an enyne cross-metathesis leading to conjugated dienes.[5]
  • Ethynylation of chiral α-(dibenzylamino) aldehydes.[6]
  • The synthesis of ethynyl aziridines.[7]
  • To prepare alkyl(triethynyl)germanes from tert-alkyltrichlorogermanes and 2-butyltrichlorogermane.[8]
  • The preperation of a key intermediate in the total synthesis of (+)-4-demethoxydaunomycin.[9]

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

Respiratory system

Supplementary Hazards

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

-20.2 °F

Flash Point(C)

-29 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

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Grafting of functionalized polymer on porous silicon surface using Grignard reagent
FZ T,et al.
Applied Surface Science, 421, 82-88 (2017)
Tandem enyne metathesis and Claisen rearrangement: a versatile approach to conjugated dienes of variable substitution patterns
Clark DA, et al.
Journal of the American Chemical Society, 128(49), 15632-15636 (2006)
An enantioselective formal synthesis of 4-demethoxydaunomycin using the catalytic asymmetric ring opening reaction of meso-epoxide with p-anisidine
Sekine A, et al.
Tetrahedron, 58(1), 75-82 (2002)
Highly heat resistant and thermo-oxidatively stable borosilane alkynyl hybrid polymers
Hua Z,et al.
Royal Society of Chemistry Advances, 5, 12161-12167 (2015)
Improved Access to 1, 8-Dichloro-10-(ethynyl) anthracene: A Useful Building Block for (Semi-) rigid Organic Frameworks
Jan-Hendrik L,et al.
Synthesis, 50, 2009-2018 (2018)

Questions

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  1. 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

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  2. 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

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