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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

Quality Level

200

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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Kopf, Henning; Pietraszuk. et al.
Organometallics, 25(10), 2533-2546 (2006)
Tetrahedron Letters, 48, 105-105 (2007)
Ederley Vélez et al.
The journal of physical chemistry. A, 109(34), 7832-7838 (2006-07-13)
The enthalpies of combustion and vaporization of 3-buten-1-ol and 3-butyn-1-ol have been measured by static bomb combustion calorimetry and correlation gas chromatography techniques, respectively, and the gas-phase enthalpies of formation, Delta(f)H degrees (m)(g), have been determined, the values being -147.3
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
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
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