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429007

Sigma-Aldrich

1-Propynylmagnesium bromide solution

0.5 M in THF

Synonym(s):

1-Propyn-1-ylmagnesium bromide, Bromo(prop-1-yn-1-yl)magnesium, Bromo-1-propynylmagnesium

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About This Item

Linear Formula:
CH3C≡CMgBr
CAS Number:
16466-97-0
Molecular Weight:
143.26
Beilstein:
3929146
MDL number:
MFCD00216588
UNSPSC Code:
12352103
PubChem Substance ID:
24866829
NACRES:
NA.22

reaction suitability

reaction type: Grignard Reaction

concentration

0.5 M in THF

bp

65-67 °C

density

0.941 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

CC#C[Mg]Br

InChI

1S/C3H3.BrH.Mg/c1-3-2;;/h1H3;1H;/q;;+1/p-1

InChI key

YVJBCTFVENNIOV-UHFFFAOYSA-M

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General description

1-Propynylmagnesiumbromide solution is 1-propynylmagnesium bromide in 0.5M tetrahydrofuran.1-propynylmagnesium bromide solution used as a Grignard reagent in chemical synthesis. This research reagent can be used for chemical and organic transformations. It is used as a regent in the conversion of [11C]CO2 to [11C] amides via Mitsunobu reaction.

Application

Preparation of hydroxy enynes which underwent gold(I)-catalyzed benzannulation leading to tetrahydronaphthalenes.

Signal Word

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

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)

30.2 °F - closed cup

Flash Point(C)

-1 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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 4: Flammable liquids
Type 1 petroleums
Hazardous rank II
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

429007-800ML:4548173149165
429007-BULK:
429007-100ML:4548173149158
429007-VAR:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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From [11 C] CO 2 to [11 C] amides: a rapid one-pot synthesis via the Mitsunobu reaction
Bongarzone S, et al.
Chemical Communications (Cambridge, England), 53(38), 5334-5337 (2017)
The [3+ 2] cycloaddition route to 5-carbomethoxy-4h-1, 2, 3-triazolo [1, 5-a][1] benzazepines from baylis-hillman acetates of 2-azidobenzaldehydes
Song YS and Lee KJ
Journal of Heterocyclic Chemistry, 43(6), 1721-1724 (2006)
Christiane M Grisé et al.
Organic letters, 8(25), 5905-5908 (2006-12-01)
We report a gold-catalyzed benzannulation of 3-hydroxy-1,5-enynes to generate tetrahydronaphthalenes. This mild process proves to be an effective method to synthesize various metasubstituted aromatic rings in good yields. [reaction: see text]

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