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129763

Sigma-Aldrich

2-Methyl-3-butyn-2-ol

98%

Synonyme(s) :

Dimethyl ethynyl carbinol

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

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Disponible pour expédition le22 avril 2025Détails

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

About This Item

Formule linéaire :
HC≡CC(CH3)2OH
Numéro CAS:
115-19-5
Poids moléculaire :
84.12
Beilstein:
635746
Numéro CE :
204-070-5
Numéro MDL:
MFCD00004467
Code UNSPSC :
12352100
ID de substance PubChem :
24847925
Nomenclature NACRES :
NA.22

30,70 €

Disponible pour expédition le22 avril 2025Détails

Devis pour commande en gros

Pression de vapeur

15 mmHg ( 20 °C)

Niveau de qualité

200

Essai

98%

Forme

liquid

Température d'inflammation spontanée

662 °F

Limite d'explosivité

16.6 %

Indice de réfraction

n20/D 1.42 (lit.)

pb

104 °C (lit.)

Pf

2.6 °C (lit.)

Densité

0.868 g/mL at 25 °C (lit.)

Groupe fonctionnel

hydroxyl

Chaîne SMILES 

CC(C)(O)C#C

InChI

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

Clé InChI

CEBKHWWANWSNTI-UHFFFAOYSA-N

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Catégories apparentées

Description générale

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]

Application

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]

Mention d'avertissement

Danger

Mentions de danger

H225,H302,H318,H336,H361fd

Classification des risques

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

Organes cibles

Central nervous system

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

66.2 °F - closed cup

Point d'éclair (°C)

19 °C - closed cup

Équipement de protection individuelle

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

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Certificats d'analyse (COA)

Lot/Batch Number
BCCK8260
BCCJ0703
BCCJ7527
BCCG8297
BCCD9106

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

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
Torstein Fjermestad et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 17(36), 10050-10057 (2011-07-21)
Density functional calculations were carried out to ascertain the origin of enantioselectivity in the brucine N-oxide (BNO)-assisted enantioselective Pauson-Khand reaction (PKR) of norbornene with 2-methyl-3-butyn-2-ol. The computed ee value in acetone is 68 % (R), which compares well to the previously
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)
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)
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)
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Questions

1–2 sur 2 questions  

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

    1 réponse

    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 réponse

    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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