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161314

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 1 petroleums
Hazardous rank II
Water insoluble liquid

JAN Code

161314-VAR:
161314-2.5ML:
161314-10ML:
161314-BULK:

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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Synlett, 809-809 (2007)
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
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
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

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