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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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Description
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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

FSL

Group 3: Spontaneously combustible substances and water- reactive materials
Materials containing Organometallic compounds
Hazardous rank II
2nd spontaneously combustible materials and water reactive materials

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

346160-800ML:4548173138435
346160-BULK:
346160-100ML:4548173138428
346160-VAR:

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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)

Articles

Reagents for C–C Bond Formation

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