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P50803

Sigma-Aldrich

Propargyl alcohol

99%

Synonyme(s) :

2-Propyn-1-ol

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45,80 €
250 ML
53,60 €
500 ML
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1 L
79,30 €

45,80 €

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Changer de vue
100 ML
45,80 €
250 ML
53,60 €
500 ML
70,50 €
1 L
79,30 €

About This Item

Formule linéaire :
HC≡CCH2OH
Numéro CAS:
107-19-7
Poids moléculaire :
56.06
Beilstein:
506003
Numéro CE :
203-471-2
Numéro MDL:
MFCD00002912
Code UNSPSC :
12352100
ID de substance PubChem :
24898591
Nomenclature NACRES :
NA.22

45,80 €

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Densité de vapeur

1.93 (vs air)

Niveau de qualité

100

Pression de vapeur

11.6 mmHg ( 20 °C)

Essai

99%

Indice de réfraction

n20/D 1.432 (lit.)

pb

114-115 °C (lit.)

Pf

−53 °C (lit.)

Densité

0.963 g/mL at 25 °C (lit.)

Température de stockage

2-8°C

Chaîne SMILES 

OCC#C

InChI

1S/C3H4O/c1-2-3-4/h1,4H,3H2

Clé InChI

TVDSBUOJIPERQY-UHFFFAOYSA-N

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Catégories apparentées

Application

Propargyl alcohol has been used as a key starting material in the [4+2] cycloisomerization mediated synthesis of various phthalide derivatives.[1]
It can also be used to synthesize:
  • A variety of regioselective furan-3-carboxamides by reacting with 3-oxo amides using Ag2CO3 as a promoter.[2]
  • β-oxopropyl esters by reacting with carboxylic acids in the presence of (arene) (phosphine)ruthenium(II) complex as a catalyst.[3]

Mention d'avertissement

Danger

Classification des risques

Acute Tox. 2 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Chronic 2 - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B - STOT RE 2

Organes cibles

Liver,Kidney

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

91.4 °F - closed cup

Point d'éclair (°C)

33 °C - closed cup

Équipement de protection individuelle

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

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Certificats d'analyse (COA)

Lot/Batch Number
MKCV4676
STBJ7484
MKCL0759
STBJ2764
STBJ0314

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Synthesis of β-oxopropyl esters by catalytic addition of carboxylic acids and N-protected amino acids to propargyl alcohol.
Devanne D, et al.
The Journal of Organic Chemistry, 53(4), 925-926 (1988)
A Stephen K Hashmi et al.
The Journal of organic chemistry, 77(17), 7761-7767 (2012-08-11)
The gold(I)-catalyzed oxidative rearrangement of propargyl alcohols provides an efficient and selective route to 1,3-diketones under mild conditions. Pyridine-N-oxides were used as external oxidants with, different from related substrates, no alkylidenecycloalkanones or oxetan-3-ones formed as side-products.
Jin Kyoon Park et al.
Organic letters, 14(18), 4790-4793 (2012-09-06)
The catalytic regioselective hydroboration of propargylic alcohols and ethers was investigated using NHC-CuCl. We observe that different NHC-CuCl complexes catalyze hydroborations of propargylic substrates with opposite regioselectivity. A 6-NHC-CuCl complex provides α-selectivity whereas β-selectivity is achieved using a 5-NHC-CuCl complex.
Ming Chen et al.
Journal of the American Chemical Society, 134(26), 10947-10952 (2012-06-27)
Chiral Brønsted acid catalyzed asymmetric allenylboration reactions are described. Under optimized conditions, anti-homopropargyl alcohols 2 are obtained in high yields with excellent diastereo- and enantioselectivities from stereochemically matched aldehyde allenylboration reactions with (M)-1 catalyzed by the chiral phosphoric acid (S)-4.
Lu Wang et al.
Organic letters, 14(23), 5848-5851 (2012-11-14)
A straightforward synthesis of fully substituted β-carbolines via Brønsted acid promoted cyclizations of α-indolyl propargylic alcohols with nitrones is described. The use of nitrones bearing alkenyl or electron-rich aryl groups as the R(4) substituent dramatically switches the reaction pathway to
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Questions

1–2 of 2 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    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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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    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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