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346152

Sigma-Aldrich

Ethynylmagnesium bromide solution

0.5 M in THF

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Synonym(s):
Acetylenemagnesium bromide, Bromoethynylmagnesium, Ethynylmagnesium bromide
Linear Formula:
HC≡CMgBr
CAS Number:
Molecular Weight:
129.24
Beilstein/REAXYS Number:
3600874
MDL number:
PubChem Substance ID:
NACRES:
NA.22

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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346152

Ethynylmagnesium bromide solution

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

reaction suitability

reaction type: Grignard Reaction

reaction suitability

reaction type: Grignard Reaction

reaction suitability

reaction type: Grignard Reaction

reaction suitability

reaction type: Grignard Reaction

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.

-

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.

signalword

Danger

Hazard Classifications

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

supp_hazards

Storage Class

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

wgk_germany

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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