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Key Documents

P50803

Sigma-Aldrich

Propargyl alcohol

99%

Synonym(s):

2-Propyn-1-ol

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About This Item

Linear Formula:
HC≡CCH2OH
CAS Number:
Molecular Weight:
56.06
Beilstein:
506003
EC Number:
MDL number:
UNSPSC Code:
12352100
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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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.

Signal Word

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

Target Organs

Liver,Kidney

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

91.4 °F - closed cup

Flash Point(C)

33 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)
Barry M Trost et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(51), 16498-16509 (2012-10-26)
The development of a general and practical zinc-catalyzed enantioselective alkyne addition methodology is reported. The commercially available ProPhenol ligand (1) has facilitated the addition of a wide range of zinc alkynylides to aryl, aliphatic, and α,β-unsaturated aldehydes in high yield
Srijit Biswas et al.
Chemical communications (Cambridge, England), 48(52), 6586-6588 (2012-05-25)
A one-step atom efficient gold(I)-catalyzed route to α-sulfenylated ketones and aldehydes from propargylic alcohols and aryl thiols is described.
Silver (i)/base-promoted propargyl alcohol-controlled regio-or stereoselective synthesis of furan-3-carboxamides and (Z)-enaminones.
Sultana S, et al.
Organic & Biomolecular Chemistry, 16(36), 6749-6759 (2018)
Daniel F Earley et al.
Molecules (Basel, Switzerland), 26(3) (2021-02-06)
89Zr-radiolabelled proteins functionalised with desferrioxamine B are a cornerstone of diagnostic positron emission tomography. In the clinical setting, 89Zr-labelled proteins are produced manually. Here, we explore the potential of using a microfluidic photochemical flow reactor to prepare 89Zr-radiolabelled proteins. The

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