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Sigma-Aldrich

4-Pentynoic acid

95%

Sinônimo(s):

Propargylacetic acid

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R$ 730,00
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About This Item

Fórmula linear:
CH≡CCH2CH2COOH
Número CAS:
6089-09-4
Peso molecular:
98.10
Beilstein:
1742047
Número CE:
228-028-0
Número MDL:
MFCD00004407
Código UNSPSC:
12352100
ID de substância PubChem:
24853886
NACRES:
NA.22

R$ 730,00

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Nível de qualidade

200

Ensaio

95%

Formulário

solid

p.e.

110 °C/30 mmHg (lit.)

pf

54-57 °C (lit.)

grupo funcional

carboxylic acid

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

OC(=O)CCC#C

InChI

1S/C5H6O2/c1-2-3-4-5(6)7/h1H,3-4H2,(H,6,7)

chave InChI

MLBYLEUJXUBIJJ-UHFFFAOYSA-N

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Descrição geral

4-Pentynoic acid undergoes copper-catalyzed intramolecular cyclizations to form enol lactones[1]. It also reacts with 1-bromo-1-alkynes in the presence of a Pd catalyst to yield biologically active ynenol lactones[2].

Aplicação

4-Pentynoic acid was used:
  • as building block for the synthesis of library of eight sequence-defined model oligomers[3]
  • in one-pot synthesis of the complex polycyclic heterocycles benzo[4,5]imidazo[1,2-c]pyrrolo[1,2-a]quinazolinone derivatives[4]
  • in the synthesis of various allenenols lactones [5(E)-(2-allenylidene)-tetrahydro-2-furanones][5]
  • in the synthesis of a cyctotoxic macrolide by ring-closing metathesis of a bis acetylene[6]

Pictogramas

Corrosion
GHS05

Palavra indicadora

Danger

Frases de perigo

H314

Classificações de perigo

Skin Corr. 1B

Código de classe de armazenamento

8A - Combustible corrosive hazardous materials

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificados de análise (COA)

Lot/Batch Number
BCCG4554
BCCD2220
BCBW3189
BCBR5173V
MKBQ0394V

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4-Pentyn-1-ol 97%

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302481

4-Pentyn-1-ol

17-Octadecynoic acid ≥95% (GC)

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O8382

17-Octadecynoic acid

Alkyne-PEG5-acid

Sigma-Aldrich

764167

Alkyne-PEG5-acid

Palladium-catalyzed synthesis of new unsaturated exo-enol lactones with potential biological activity.
Bouyssi D, et al.
Tetrahedron Letters, 34(19), 3129-3130 (1993)
Thomas L Mindt et al.
The Journal of organic chemistry, 72(26), 10247-10250 (2007-11-30)
Alkynoic acids, in particular, 4-pentynoic acid derivatives, undergo intramolecular cyclizations to enol lactones under reaction conditions typically applied for the Cu(I)-catalyzed cycloaddition of terminal alkynes and azides (click chemistry). Starting from appropriate alkynoic acid derivatives, either enol lactones or 1,2,3-triazole
Thanh Tam Trinh et al.
Macromolecular rapid communications, 35(2), 141-145 (2013-12-18)
A library of eight sequence-defined model oligomers, whose sequence is based on a (0,1) binary code, is prepared through chemoselective repeating cycles of amidification and copper-assisted alkyne-azide cycloaddition reactions from a non-modified Wang resin. This library is constructed from two
Xun Ji et al.
The Journal of organic chemistry, 78(9), 4312-4318 (2013-04-06)
An efficient and facile Au(I)/Ag(I)-catalyzed cascade method has been developed for one-pot synthesis of the complex polycyclic heterocycles benzo[4,5]imidazo[1,2-c]pyrrolo[1,2-a]quinazolinone derivatives through treatment of the substituted 2-(1H-benzo[d]imidazol-2-yl)anilines with 4-pentynoic acid or 5-hexynoic acid. The strategy features a Au(I)/Ag(I)-catalyzed one-pot cascade process
Xin Zhou et al.
Acta biomaterialia, 54, 128-137 (2017-03-13)
Wound healing dressings are increasingly needed clinically due to the large number of skin damage annually. Nitric oxide (NO) plays a key role in promoting wound healing, thus biomaterials with NO-releasing property receive increasing attention as ideal wound dressing. In
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Artigos

Introduction of Terminal Azide and Alkyne Functionalities in Polymers

Click chemistry, and the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) in particular, is a powerful new synthetic tool in polymer chemistry and material science.

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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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    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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