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346160

Sigma-Aldrich

Ethynylmagnesium chloride solution

0.5 M in THF

Synonym(s):

Chloromagnesium acetylide

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About This Item

Linear Formula:
CH≡CMgCl
CAS Number:
65032-27-1
Molecular Weight:
84.79
MDL number:
MFCD00075343
UNSPSC Code:
12352103
PubChem Substance ID:
24861377
NACRES:
NA.22

form

liquid

reaction suitability

reaction type: Grignard Reaction

concentration

0.5 M in THF

density

0.921 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

Cl[Mg]C#C

InChI

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

InChI key

YEWNLGTVYUADOR-UHFFFAOYSA-M

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Application

Ethynylmagnesium chloride solution can be used:
  • To synthesize 1-ethynyldeoxyribose derivatives which can further undergo Sonogashira coupling with various aryl, heteroaryl, and metallocenyl derivatives.
  • In one of the key synthetic steps of substituted naphthostyrils.
  • In the preparation of propargylic ester precursor for the synthesis of 1,3-dienylphosphonates.

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Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

-16.6 °F - closed cup

Flash Point(C)

-27 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN9136
SHBN9135
SHBN3133
SHBM5296
SHBL0068

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A novel and convenient method for the synthesis of substituted naphthostyrils
Liu J, et al.
Tetrahedron Letters, 44(12), 2545-2548 (2003)
Sonogashira reactions of α-and β-1-ethynyl-2-deoxyribosides: synthesis of acetylene-extended C-nucleosides
Bobula T, et al.
Tetrahedron, 66(2), 530-536 (2010)
New and efficient synthesis of 1, 3-dienylphosphonates by Palladium-catalyzed substitution of propargylic esters to diethyl phosphite
Liu X, et al.
Synthetic Communications, 43(19), 2622-2626 (2013)

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Reagents for C–C Bond Formation

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