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Merck
CN

P50803

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24898591
EC Number:
203-471-2
Beilstein/REAXYS Number:
506003
MDL number:
MFCD00002912

Key Documents

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Product Name

Propargyl alcohol, 99%

InChI

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

InChI key

TVDSBUOJIPERQY-UHFFFAOYSA-N

SMILES string

OCC#C

vapor density

1.93 (vs air)

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

Quality Level

100

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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.

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

target_organs

Liver,Kidney

Storage Class

3 - Flammable liquids

wgk

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

Regulatory Information

监管及禁止进口产品
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Certificates of Analysis (COA)

Lot/Batch Number
SDBB5276
MKCZ3512
MKCV4676
STBJ7484
MKCL0759

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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
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.
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.
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