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Sigma-Aldrich

3-Butyn-2-one

95%

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About This Item

Linear Formula:
HC≡CCOCH3
CAS Number:
1423-60-5
Molecular Weight:
68.07
Beilstein:
605353
EC Number:
215-834-2
MDL number:
MFCD00008775
UNSPSC Code:
12352100
PubChem Substance ID:
24849921
NACRES:
NA.22

Assay

95%

refractive index

n20/D 1.406 (lit.)

bp

85 °C (lit.)

density

0.87 g/mL at 25 °C (lit.)

SMILES string

CC(=O)C#C

InChI

1S/C4H4O/c1-3-4(2)5/h1H,2H3

InChI key

XRGPFNGLRSIPSA-UHFFFAOYSA-N

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General description

3-Butyn-2-one undergoes asymmetric double-Michael reaction with ortho-tosylamidophenyl malonate catalyzed by chiral aminophosphines to yield indolines. It undergoes double Michael reaction with nitrogen-containing tethered diacid to give pipecolic acid derivatives.

Application

3-Butyn-2-one was used in the synthesis of clerodane diterpenoid (+/-)-sacacarin. It was used as substrate in stereoselective, conjugate arylation mediated by gallium(III) chloride leading to (E)-α,β-unsaturated ketones.

Pictograms

FlameSkull and crossbones
GHS02,GHS06

Signal Word

Danger

Hazard Statements

H225,H300,H315,H319,H335

Hazard Classifications

Acute Tox. 2 Oral - Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

30.2 °F - closed cup

Flash Point(C)

-1 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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R B Grossman et al.
Organic letters, 3(25), 4027-4030 (2001-12-12)
[reaction: see text] The putative structure of the naturally occurring clerodane diterpenoid (+/-)-sacacarin has been prepared in only 10 steps, six of which are C-C bond-forming steps, in a chemo-, regio-, and diastereoselective manner. The key part of the synthesis
Synlett, 809-809 (2007)
San N Khong et al.
Molecules (Basel, Switzerland), 17(5), 5626-5650 (2012-05-15)
The bisphosphine-catalyzed double-Michael addition of dinucleophiles to electron-deficient acetylenes is an efficient process for the synthesis of many nitrogen-containing heterocycles. Because the resulting heterocycles contain at least one stereogenic center, this double-Michael reaction would be even more useful if an
F Hughes et al.
Organic letters, 3(18), 2911-2914 (2001-09-01)
[reaction: see text]. Nitrogen-containing tethered diacids, easily prepared by reductive alkylation of diethyl aminomalonate or ethyl cyanoglycinate, undergo double Michael reactions with 3-butyn-2-one to give highly functionalized and substituted piperidines (pipecolic acid derivatives) with surprisingly high stereoselectivity. The heterocyclic double

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