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Merck

129763

Sigma-Aldrich

2-Methyl-3-butyn-2-ol

98%

Sinónimos:

Dimethyl ethynyl carbinol

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100 ML
32,30 €
250 ML
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71,40 €

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100 ML
32,30 €
250 ML
38,70 €
1 L
71,40 €

About This Item

Fórmula lineal:
HC≡CC(CH3)2OH
Número de CAS:
Peso molecular:
84.12
Beilstein:
635746
Número CE:
Número MDL:
Código UNSPSC:
12352100
ID de la sustancia en PubChem:
NACRES:
NA.22

32,30 €


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presión de vapor

15 mmHg ( 20 °C)

Nivel de calidad

Ensayo

98%

Formulario

liquid

temp. de autoignición

662 °F

lim. expl.

16.6 %

índice de refracción

n20/D 1.42 (lit.)

bp

104 °C (lit.)

mp

2.6 °C (lit.)

densidad

0.868 g/mL at 25 °C (lit.)

grupo funcional

hydroxyl

cadena SMILES

CC(C)(O)C#C

InChI

1S/C5H8O/c1-4-5(2,3)6/h1,6H,2-3H3

Clave InChI

CEBKHWWANWSNTI-UHFFFAOYSA-N

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Descripción general

2-Methyl-3-butyn-2-ol (MBY) is used as a precursor in the Mannich reaction and can undergo selective semihydrogenation to produce fine chemicals.[1][2]

Aplicación

2-Methyl-3-butyn-2-ol can be used as a reactant to synthesize:,·
  • Aryl-2-methyl-3-butyn-2-ols via Pd-catalyzed Sonogashira coupling reaction with various aryl bromides.[3]      
  • 2-Methyl-3-buten-2-ol (MBE) by Pd/γ-Al2O3 catalyzed selective hydrogenation reaction. MBE is applicable as an important intermediate in the synthesis of vitamin A.[4]      
  • Diarylacetylenes via Pd-catalyzed Sonogashira coupling reaction with aryl chlorides in the presence of Cs2CO3 as a base.[5] 
  • Optically active propargylic alcohols by enantioselective addition reaction with various aldehydes in the presence of Zn(OTf)2 and N-methylephedrine.[6]

Palabra de señalización

Danger

Clasificaciones de peligro

Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - STOT SE 3

Órganos de actuación

Central nervous system

Código de clase de almacenamiento

3 - Flammable liquids

Clase de riesgo para el agua (WGK)

WGK 1

Punto de inflamabilidad (°F)

66.2 °F - closed cup

Punto de inflamabilidad (°C)

19 °C - closed cup

Equipo de protección personal

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


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Certificados de análisis (COA)

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Palladium-Catalyzed Efficient and One-Pot Synthesis of Diarylacetylenes from the Reaction of Aryl Chlorides with 2-Methyl-3-butyn-2-ol
Yi Chenyi, et al.
Advanced Synthesis & Catalysis, 349(10), 1738-1742 (2007)
2-Methyl-3-butyn-2-ol as an acetylene precursor in the Mannich reaction. A new synthesis of suicide inactivators of monoamine oxidase
Fowler JS
The Journal of Organic Chemistry, 42(15) , 2637-2639 (1977)
Boyall et al.
Organic letters, 2(26), 4233-4236 (2001-01-11)
We report the first example of enantioselective aldehyde additions of 2-methyl-3-butyn-2-ol, a commodity bulk chemical that is readily available. Following a facile fragmentation reaction, the addition reactions provide access to optically active terminal acetylenes as useful building blocks for asymmetric
General kinetic modeling of the selective hydrogenation of 2-methyl-3-butyn-2-ol over a commercial palladium-based catalyst
Vernuccio S, et al.
Industrial & Engineering Chemistry Research, 54(46), 11543-11551 (2015)
Continuous 2-Methyl-3-Butyn-2-ol Selective Hydrogenation on Pd/?-Al2O3 as a Green Pathway of Vitamin A Precursor Synthesis
Fernandez-Ropero AJ, et al.
Catalysts, 11(4), 501-501 (2021)

Preguntas

1–2 de 2 Preguntas  
  1. How can I determine the shelf life / expiration / retest date of this product?

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

    1 respuesta
    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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