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Merck
CN

346152

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
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3600874
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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


signalword

Danger

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

Hazard Classifications

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

Regulatory Information

危险化学品

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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)
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)



Global Trade Item Number

SKUGTIN
346152-PZ04061823834124
346152-100ML04061826760987
346152-800ML04061826760994