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Sigma-Aldrich

2-Methyl-3-butyn-2-ol

98%

Sinônimo(s):

Dimethyl ethynyl carbinol

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100 ML
R$ 352,00
250 ML
R$ 359,00
1 L
R$ 715,00

About This Item

Fórmula linear:
HC≡CC(CH3)2OH
Número CAS:
115-19-5
Peso molecular:
84.12
Beilstein:
635746
Número CE:
204-070-5
Número MDL:
MFCD00004467
Código UNSPSC:
12352100
ID de substância PubChem:
24847925
NACRES:
NA.22

R$ 352,00

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pressão de vapor

15 mmHg ( 20 °C)

Nível de qualidade

200

Ensaio

98%

Formulário

liquid

temperatura de autoignição

662 °F

Lim. expl.

16.6 %

índice de refração

n20/D 1.42 (lit.)

p.e.

104 °C (lit.)

pf

2.6 °C (lit.)

densidade

0.868 g/mL at 25 °C (lit.)

grupo funcional

hydroxyl

cadeia de caracteres SMILES

CC(C)(O)C#C

InChI

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

chave InChI

CEBKHWWANWSNTI-UHFFFAOYSA-N

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Descrição geral

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]

Aplicação

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]

Palavra indicadora

Danger

Classificações de perigo

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

Órgãos-alvo

Central nervous system

Código de classe de armazenamento

3 - Flammable liquids

Classe de risco de água (WGK)

WGK 1

Ponto de fulgor (°F)

66.2 °F - closed cup

Ponto de fulgor (°C)

19 °C - closed cup

Equipamento de proteção individual

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

Escolha uma das versões mais recentes:

Certificados de análise (COA)

Lot/Batch Number
BCCK8260
BCCJ0703
BCCJ7527
BCCG8297
BCCD9106

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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)
Andrea Caporale et al.
Beilstein journal of organic chemistry, 10, 384-393 (2014-03-08)
Two efficient protocols for the palladium-catalyzed synthesis of aryl-2-methyl-3-butyn-2-ols from aryl bromides in the absence of copper were developed. A simple catalytic system consisting of Pd(OAc)2 and P(p-tol)3 using DBU as the base and THF as the solvent was found
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Questions

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  1. 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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  2. 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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