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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:
107-19-7
Molecular Weight:
56.06
Beilstein:
506003
EC Number:
203-471-2
MDL number:
MFCD00002912
UNSPSC Code:
12352100
PubChem Substance ID:
24898591
NACRES:
NA.22

vapor density

1.93 (vs air)

Quality Level

100

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

Certificates of Analysis (COA)

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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
Hua-Dong Xu et al.
Organic letters, 15(4), 840-843 (2013-01-30)
Cross-dimerization of terminal arylacetylenes and terminal propargylic alcohols/amides has been achieved in the presence of a rhodium catalyst. This method features high chemo- and regioselectivities rendering convenient and atom economical access to functionalized enynes.
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)
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.
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