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Merck

129763

Sigma-Aldrich

2-甲基-3-丁炔-2-醇

98%

别名:

甲基丁炔醇

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About This Item

线性分子式:
HC≡CC(CH3)2OH
CAS号:
分子量:
84.12
Beilstein:
635746
EC號碼:
MDL號碼:
分類程式碼代碼:
12352100
PubChem物質ID:
NACRES:
NA.22

蒸汽壓力

15 mmHg ( 20 °C)

品質等級

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.)

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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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。

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。      
  • 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。      
  • 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。
  • 在 Zn(OTf)2N-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。

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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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
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
Micaela Crespo-Quesada et al.
Journal of the American Chemical Society, 133(32), 12787-12794 (2011-07-14)
The activity and selectivity of structure-sensitive reactions are strongly correlated with the shape and size of the nanocrystals present in a catalyst. This correlation can be exploited for rational catalyst design, especially if each type of surface atom displays a
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)
Shinji Harada et al.
Chemical communications (Cambridge, England), (9)(9), 948-950 (2007-02-22)
Indium(III)-catalyzed asymmetric alkynylation of aryl, heteroaryl, alkyl and alkenyl aldehydes with 2-methyl-3-butyn-2-ol as an ethyne equivalent donor was realized, and products were obtained in moderate to good yields (up to 97%) and high enantioselectivities (up to 99% ee) using 2-10

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