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Sigma-Aldrich

2-甲基-3-丁炔-2-醇

98%

同義詞:

甲基丁炔醇

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About This Item

線性公式:
HC≡CC(CH3)2OH
CAS號碼:
115-19-5
分子量：:
84.12
Beilstein:
635746
EC號碼:
204-070-5
MDL號碼:
MFCD00004467
分類程式碼代碼:
12352100
PubChem物質ID:
24847925
NACRES:
NA.22
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蒸汽壓力

15 mmHg ( 20 °C)

品質等級

200

化驗

98%

形狀

liquid

自燃溫度

662 °F

expl. lim.

16.6 %

折射率

n20/D 1.42 (lit.)

bp

104 °C (lit.)

mp

2.6 °C (lit.)

密度

0.868 g/mL at 25 °C (lit.)

官能基

hydroxyl

SMILES 字串

CC(C)(O)C#C

InChI

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

InChI 密鑰

CEBKHWWANWSNTI-UHFFFAOYSA-N

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相關類別

一般說明

2-甲基-3-丁炔-2-醇(MBY) 可用作Mannich反应的前体，并可通过选择性半氢化反应生成精细化学品。[1][2]

應用

2-甲基-3-丁炔-2-醇可用作反应物，通过钯催化的与各种芳基溴化物的 Sonogashira 偶联反应合成：
  • 芳基-2-甲基-3-丁炔-2-醇。[3]      
  • Pd/γ-Al2O3 催化的 2-甲基-3-丁烯-2-醇（MBE）选择性加氢反应。MBE 可作为合成维生素 A 的重要中间体。[4]      
  • 在 Cs2CO3 作为碱的存在下，通过 Pd 催化的 Sonogashira 与芳基氯化物的偶联反应合成二芳基乙炔。[5]
  • 在 Zn(OTf)2 和 N-甲基麻黄碱存在下，通过与各种醛的对映选择性加成反应合成具有光学活性的炔丙醇。[6]

訊號詞

Danger

危險分類

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

標靶器官

Central nervous system

儲存類別代碼

3 - Flammable liquids

水污染物質分類（WGK）

WGK 1

閃點（°F）

66.2 °F - closed cup

閃點（°C）

19 °C - closed cup

個人防護裝備

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

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分析證明 (COA)

Lot/Batch Number
BCCK8260
BCCJ0703
BCCJ7527
BCCG8297
BCCD9106

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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
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
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      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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    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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