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P50803

Sigma-Aldrich

Propargyl alcohol

99%

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Synonym(s):
2-Propyn-1-ol
Linear Formula:
HC≡CCH2OH
CAS Number:
Molecular Weight:
56.06
Beilstein/REAXYS Number:
506003
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

vapor density

1.93 (vs air)

Quality Level

vapor pressure

11.6 mmHg ( 20 °C)

assay

99%

refractive index

n20/D 1.432 (lit.)

bp

114-115 °C (lit.)

mp

−53 °C (lit.)

density

0.963 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

OCC#C

InChI

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

InChI key

TVDSBUOJIPERQY-UHFFFAOYSA-N

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1 of 4

This Item
453021459798615048
vibrant-m

P50803

Propargyl alcohol

vibrant-m

453021

Allyl alcohol

vibrant-m

459798

Allyl alcohol

vibrant-m

615048

1-Propanol-1,1,2,2,3,3,3-d7

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

bp

114-115 °C (lit.)

bp

96-98 °C (lit.)

bp

96-98 °C (lit.)

bp

97 °C (lit.)

mp

−53 °C (lit.)

mp

−129 °C (lit.)

mp

−129 °C (lit.)

mp

-127 °C (lit.)

refractive index

n20/D 1.432 (lit.)

refractive index

n20/D 1.412 (lit.)

refractive index

n20/D 1.412 (lit.)

refractive index

-

density

0.963 g/mL at 25 °C (lit.)

density

0.854 g/mL at 25 °C (lit.)

density

0.854 g/mL at 25 °C (lit.)

density

0.896 g/mL at 25 °C

Application

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.

signalword

Danger

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

91.4 °F - closed cup

flash_point_c

33 °C - closed cup

ppe

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


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Customers Also Viewed

Slide 1 of 9

1 of 9

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.
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
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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