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346152

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:
4301-14-8
Molecular Weight:
129.24
Beilstein/REAXYS Number:
3600874
MDL number:
MFCD00075342
UNSPSC Code:
12352103
PubChem Substance ID:
24861376
NACRES:
NA.22

Quality Level

200

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.

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.

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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

EUH019

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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Certificates of Analysis (COA)

Lot/Batch Number
STBL4080
SHBR7549
SHBR4981
STBL3325
SHBR7550

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Diastereoselective Ethynylation of Chiral α-(Dibenzylamino) Aldehydes: Synthesis of meso-and Homochiral C2-Symmetrical 1, 6-Diamino-2, 5-diols
Andres JM, et al.
European Journal of Organic Chemistry, 2006(15), 3442-3450 (2006)
Reactions of carbon nucleophiles with 2, 2, 3-trisubstituted ethynylaziridines
Kelley BT and Joullie MM
Tetrahedron Asymmetry, 24(19), 1233-1239 (2013)
(3+ 2)-Cyclization Reactions of Unsaturated Phosphonites with Aldehydes and Thioketones
Don MS,et al.
Chemistry?A European Journal , 29, e202300806-e202300806 (2023)
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
European Journal of Organic Chemistry, 3442-3442 (2006)
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