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Merck

346152

Sigma-Aldrich

Ethynylmagnesium bromide solution

0.5 M in THF

Sinónimos:

Acetylenemagnesium bromide, Bromoethynylmagnesium, Ethynylmagnesium bromide

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About This Item

Fórmula lineal:
HC≡CMgBr
Número de CAS:
Peso molecular:
129.24
Beilstein:
3600874
Número MDL:
Código UNSPSC:
12352103
ID de la sustancia en PubChem:
NACRES:
NA.22
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Nivel de calidad

idoneidad de la reacción

reaction type: Grignard Reaction

concentración

0.5 M in THF

densidad

0.94 g/mL at 25 °C

temp. de almacenamiento

2-8°C

cadena SMILES

Br[Mg]C#C

InChI

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

Clave InChI

HUGJUYPSXULVQQ-UHFFFAOYSA-M

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Descripción general

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]

Aplicación

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]

Palabra de señalización

Danger

Clasificaciones de peligro

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

Órganos de actuación

Respiratory system

Riesgos supl.

Código de clase de almacenamiento

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

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

-20.2 °F

Punto de inflamabilidad (°C)

-29 °C

Equipo de protección personal

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


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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)
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)
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)
Daniel A Clark et al.
Journal of the American Chemical Society, 128(49), 15632-15636 (2006-12-07)
To extend the versatility of the ruthenium carbene-promoted enyne metathesis, it was combined with an Ireland ester enolate Claisen rearrangement. This reaction sequence provided conjugated dienes of higher substitution pattern than that obtained through a cross-enyne metathesis alone. The Ireland-Claisen

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    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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