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225584

Sigma-Aldrich

Vinylmagnesium bromide solution

1.0 M in THF

Sinonimo/i:

Bromoethenylmagnesium, Bromovinylmagnesium

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About This Item

Formula condensata:
CH2=CHMgBr
Numero CAS:
1826-67-1
Peso molecolare:
131.25
Beilstein:
3535841
Numero MDL:
MFCD00000042
Codice UNSPSC:
12352103
ID PubChem:
24853507
NACRES:
NA.22
Prezzi e disponibilità al momento non sono disponibili

Livello qualitativo

100

Impiego in reazioni chimiche

reaction type: Grignard Reaction

Concentrazione

1.0 M in THF

Densità

0.981 g/mL at 25 °C

Stringa SMILE

Br[Mg]C=C

InChI

1S/C2H3.BrH.Mg/c1-2;;/h1H,2H2;1H;/q;;+1/p-1
XHHHAXOHMKAOSL-UHFFFAOYSA-M

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Applicazioni

Vinylmagnesium bromide solution (1 M in THF) may be used in the synthesis of 2-vinylchroman-4-ones by the conjugate addition with chromones in the presence of a Lewis acid.[1]
It may also be used in the following transformations:
  • (S)-3-(benzyloxy)-4-oxo-butanoic acid methyl ester to methyl (3S,4S)-4-hydroxy-3-(phenylmethoxy)hex-5-enoate.[2]
  • (R)-1-Azido-5,6-epoxyhexane to (S)-1-(4-azidobutyl)-2-propen-1-ol.[3]
  • 2,3-O-Isopropylidene-D-ribose to 1-[(4R,5S)-5-((1S)-1-hydroxyallyl)-2,2-dimethyl[1,3]dioxolan-4-yl]ethane-1,2-diol.[4]
  • (4S,5S)-2,2-Dimethyl-5-vinyl[1,3]dioxolane-4-carbaldehyde to (1R,4R,5S)- and (1S,4R,5S)-1-(2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)prop-2-en-1-ol.[4]
  • Ethyl levulinate to ?-methyl-?-vinylbutyrolactone.[5]

Confezionamento

View returnable container options.

Altre note

Storage below 25°C may cause crystallization. Warm gently to redissolve.

Avvertenze

Danger

Indicazioni di pericolo

H225,H260,H302,H314,H335,H336,H351

Classi di pericolo

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

Organi bersaglio

Respiratory system

Rischi supp

EUH019

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 1

Punto d’infiammabilità (°F)

1.4 °F

Punto d’infiammabilità (°C)

-17.0 °C

Dispositivi di protezione individuale

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificati d'analisi (COA)

Lot/Batch Number
SHBR2629
STBL4751
STBL4729
STBL3324
STBL2601

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A new asymmetric entry to 2-substituted piperidines. A concise synthesis of (+)-coniine,(?)-pelletierine,(+)-?-coniceine, and (+)-epidihydropinidine.
Takahata H
Tetrahedron Asymmetry, 7(10), 3047-3054 (1996)
Synthesis and structure?activity relationships of 2-vinylchroman-4-ones as potent antibiotic agents.
Albrecht U
Bioorganic & Medicinal Chemistry, 13(5), 1531-1536 (2005)
A useful new enantiomerically pure synthon from malic acid: chelation controlled activation as a route to regioselectivity.
Keck G E
The Journal of Organic Chemistry, 56(1), 417-420 (1991)
A new endogenous natriuretic factor: LLU-alpha.
Wechter W J
Proceedings of the National Academy of Sciences of the USA, 93(12), 6002-6007 (1996)
Improved and alternative synthesis of D-and L-cyclopentenone derivatives, the versatile intermediates for the synthesis of carbocyclic nucleosides.
Moon H R
Tetrahedron Asymmetry, 13(11), 1189-1193 (2002)
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Questions

1–2 of 2 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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