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Merck

P50803

Sigma-Aldrich

Propargylalkohol

99%

Synonym(e):

2-Propin-1-ol

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About This Item

Lineare Formel:
HC≡CCH2OH
CAS-Nummer:
Molekulargewicht:
56.06
Beilstein:
506003
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352100
PubChem Substanz-ID:
NACRES:
NA.22

Dampfdichte

1.93 (vs air)

Qualitätsniveau

Dampfdruck

11.6 mmHg ( 20 °C)

Assay

99%

Brechungsindex

n20/D 1.432 (lit.)

bp

114-115 °C (lit.)

mp (Schmelzpunkt)

−53 °C (lit.)

Dichte

0.963 g/mL at 25 °C (lit.)

Lagertemp.

2-8°C

SMILES String

OCC#C

InChI

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

InChIKey

TVDSBUOJIPERQY-UHFFFAOYSA-N

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Anwendung

Propargyl alcohol has been used as a key starting material in the [4+2] cycloisomerization mediated synthesis of various phthalide derivatives.
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.
  • β-oxopropyl esters by reacting with carboxylic acids in the presence of (arene) (phosphine)ruthenium(II) complex as a catalyst.

Signalwort

Danger

Gefahreneinstufungen

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

Zielorgane

Liver,Kidney

Lagerklassenschlüssel

3 - Flammable liquids

WGK

WGK 3

Flammpunkt (°F)

91.4 °F - closed cup

Flammpunkt (°C)

33 °C - closed cup

Persönliche Schutzausrüstung

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


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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)
Guangyan Zhang et al.
Polymers, 11(2) (2019-04-10)
The temperature responsive PEGylated polyaspartamide derivative, denoted as mPEG-PAAHP, was synthesized by the click reaction. FTIR and ¹H NMR were adopted to characterize and confirm the chemical structures of the obtained mPEG-PAAHPs. The temperature responsive behavior investigated by transmittance and
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
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.
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.

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