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346152

Ethynylmagnesium bromide solution

0.5 M in THF

Synonym(s):

Acetylenemagnesium bromide, Bromoethynylmagnesium, Ethynylmagnesium bromide

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Pack SizeSKUAvailabilityPrice
100 mL

Available to ship TODAYfromMILWAUKEE

$81.10
800 mL

Available to ship TODAYfromMILWAUKEE

$363.00

About This Item

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

$81.10


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Quality Level

reaction suitability

reaction type: Grignard Reaction

packaging

Sure/Seal of

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

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.

Application

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

Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

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This Item
775797419613470260
reaction suitability

reaction type: Grignard Reaction

reaction suitability

reaction type: Grignard Reaction

reaction suitability

reaction type: Grignard Reaction

reaction suitability

reaction type: Grignard Reaction

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

100

density

0.94 g/mL at 25 °C

density

0.982 g/mL at 25 °C

density

0.952 g/mL at 25 °C

density

0.955 g/mL at 25 °C

concentration

0.5 M in THF

concentration

0.75 M in THF

concentration

0.5 M in THF

concentration

0.5 M in THF

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

storage temp.

-

packaging

Sure/Seal of

packaging

Sure/Seal of

packaging

Sure/Seal of

packaging

Sure/Seal of


signalword

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

supp_hazards

Storage Class

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

ppe

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)
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)



Global Trade Item Number

SKUGTIN
346152-100ML04061826760987
346152-800ML04061826760994

Questions

1–2 of 2 Questions  
  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/418/501/product-dating-information-06-25-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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