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130850

Sigma-Aldrich

3-Butyn-1-ol

97%

Synonym(s):

3-Butynol

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About This Item

Linear Formula:
HC≡CCH2CH2OH
CAS Number:
927-74-2
Molecular Weight:
70.09
Beilstein:
773710
EC Number:
213-161-9
MDL number:
MFCD00002955
UNSPSC Code:
12352100
eCl@ss:
39020335
PubChem Substance ID:
24847980
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.441 (lit.)

bp

128.9 °C (lit.)

mp

−63.6 °C (lit.)

density

0.926 g/mL at 25 °C (lit.)

SMILES string

OCCC#C

InChI

1S/C4H6O/c1-2-3-4-5/h1,5H,3-4H2

InChI key

OTJZCIYGRUNXTP-UHFFFAOYSA-N

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General description

The enthalpies of combustion and vaporization of 3-butyn-1-ol is measured by static bomb combustion calorimetry and correlation gas chromatography techniques.

Application

3-Butyn-1-ol was used to prepare Markovnikov addition product.
Alkynyl substrate used in a study of a palladium-catalyzed coupling with β-tetrionic acid bromide leading to alkynyl substituted furanones in good yield.
Synthon for preparation of oxygen-containing heterocycles and protected esters of s-Hydroxy-L-isoleucine

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

96.8 °F - closed cup

Flash Point(C)

36 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tetrahedron Letters, 48, 105-105 (2007)
Kopf, Henning; Pietraszuk. et al.
Organometallics, 25(10), 2533-2546 (2006)
Kristen Bennett et al.
Applied and environmental microbiology, 82(8), 2270-2279 (2016-01-31)
Nitrosomonas europaea is an aerobic nitrifying bacterium that oxidizes ammonia (NH3) to nitrite (NO2 (-)) through the sequential activities of ammonia monooxygenase (AMO) and hydroxylamine dehydrogenase (HAO). Many alkynes are mechanism-based inactivators of AMO, and here we describe an activity-based
Deniz Dogruer et al.
Bioorganic & medicinal chemistry letters, 14(2), 523-526 (2003-12-31)
The binding of a series pyridylbutynylamines 6 was examined at alpha4beta2 nACh receptors. Structural modifications, comparing 6 with pyridyl ethers 2, did not consistently result in parallel effects on receptor affinity, suggesting possible differences in their modes of binding. Furthermore
Sumod A Pullarkat et al.
Inorganic chemistry, 45(18), 7455-7463 (2006-08-29)
Alcohol functionalized diphosphine ligands with chirality residing on the carbon backbone were prepared using a novel two-stage asymmetric synthetic methodology from the corresponding terminal alkynols. Under mild conditions, the alkynols, 3-butyn-1-ol and 2-propyn-1-ol, were subjected to direct hydrophosphination to give
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