Propynal

Names
Preferred IUPAC name

Prop-2-ynal

Other names

Propiolaldehyde; Propiolic aldehyde

Identifiers

CAS Number

* 624-67-9 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 11721

PubChem CID

* 12222

UNII |

* SJ8A65XF7N Y

SMILES

* C#CC=O

Properties

Chemical formula

| C3H2O
Molar mass | 54.048 g·mol−1
Boiling point |  54–57 °C (129–135 °F; 327–330 K)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Tracking categories (test):

* SizeSet

Propynal is an organic compound with molecular formula HC2CHO. It is the simplest chemical compound containing both alkyne and aldehyde functional groups. It is a colorless liquid with explosive properties.[1]

The compound exhibits reactions expected for an electrophilic alkynyl aldehyde. It is a dienophile and a good Michael acceptor. Grignard reagents add to the carbonyl center.[1]

## Contents

* 1 Occurrence in interstellar medium
* 2 Hazards
* 3 See also
* 4 References

## Occurrence in interstellar medium

Propynal has been observed in the interstellar medium. It is hypothesized to be formed from a carbon monoxide-acetylene complex.[2] Another possible pathway is through the reaction of propynylidyne (C3H) with water.[3]

## Hazards

The compound is explosive, possibly because it tends to polymerize.[1]

## See also

* Acrolein
* Propiolic acid

## References

1. ↑ 1.0 1.1 1.2 P. Perlmutter (2001). "Encyclopedia of Reagents for Organic Synthesis". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rp262m. ISBN 978-0471936237.
2. ↑ Zhou, Li; Ralf I. Kaiser (2008), "Pathways to Oxygen-Bearing Molecules in the Interstellar Medium and in Planetary Atmospheres: Cyclopropenone (c-C3H2O) and Propynal (HCCCHO)", The Astrophysical Journal 686 (2), doi:10.1086/591072
3. ↑ Xie, Hong-bin; Chang-bin Shao (2007), "Radical-Molecule Reaction C3H + H2O on Amorphous Water Ice: A Promising Route for Interstellar Propynal", The Astrophysical Journal 670 (1): 449–456, doi:10.1086/520757

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* t
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Molecules detected in outer space

Molecules|

| Diatomic|

* Aluminium monochloride
* Aluminium monofluoride
* Aluminium monoxide
* Argonium
* Carbon monophosphide
* Carbon monosulfide
* Carbon monoxide
* Carborundum
* Cyanogen radical
* Diatomic carbon
* Fluoromethylidynium
* Helium hydride ion
* Hydrogen chloride
* Hydrogen fluoride
* Hydrogen (molecular)
* Hydroxyl radical
* Iron(II) oxide
* Magnesium monohydride cation
* Methylidyne radical
* Nitric oxide
* Nitrogen (molecular)
* Nitrogen monohydride
* Nitrogen sulfide
* Oxygen (molecular)
* Phosphorus monoxide
* Phosphorus mononitride
* Potassium chloride
* Silicon carbide
* Silicon mononitride
* Silicon monoxide
* Silicon monosulfide
* Sodium chloride
* Sodium iodide
* Sulfur monohydride
* Sulfur monoxide
* Titanium oxide

|
|

Triatomic|

* Aluminium hydroxide
* Aluminium isocyanide
* Amino radical
* Carbon dioxide
* Carbonyl sulfide
* CCP radical
* Chloronium
* Diazenylium
* Dicarbon monoxide
* Disilicon carbide
* Ethynyl radical
* Formyl radical
* Hydrogen cyanide (HCN)
* Hydrogen isocyanide (HNC)
* Hydrogen sulfide
* Hydroperoxyl
* Iron cyanide
* Isoformyl
* Magnesium cyanide
* Magnesium isocyanide
* Methylene radical
* N2H+
* Nitrous oxide
* Nitroxyl
* Ozone
* Phosphaethyne
* Potassium cyanide
* Protonated molecular hydrogen
* Sodium cyanide
* Sodium hydroxide
* Silicon carbonitride
* c-Silicon dicarbide
* SiNC
* Sulfur dioxide
* Thioformyl
* Thioxoethenylidene
* Titanium dioxide
* Tricarbon
* Water

Four
atoms|

* Acetylene
* Ammonia
* Cyanic acid
* Cyanoethynyl
* Cyclopropynylidyne
* Formaldehyde
* Fulminic acid
* HCCN
* Hydrogen peroxide
* Hydromagnesium isocyanide
* Isocyanic acid
* Isothiocyanic acid
* Ketenyl
* Methylene amidogen
* Methyl radical
* Propynylidyne
* Protonated carbon dioxide
* Protonated hydrogen cyanide
* Silicon tricarbide
* Thioformaldehyde
* Tricarbon monoxide
* Tricarbon sulfide
* Thiocyanic acid

Five
atoms|

* Ammonium ion
* Butadiynyl
* Carbodiimide
* Cyanamide
* Cyanoacetylene
* Cyanoformaldehyde
* Cyanomethyl
* Cyclopropenylidene
* Formic acid
* Isocyanoacetylene
* Ketene
* Methane
* Methoxy radical
* Methylenimine
* Propadienylidene
* Protonated formaldehyde
* Protonated formaldehyde
* Silane
* Silicon-carbide cluster

Six
atoms|

* Acetonitrile
* Cyanobutadiynyl radical
* E-Cyanomethanimine
* Cyclopropenone
* Diacetylene
* Ethylene
* Formamide
* HC4N
* Ketenimine
* Methanethiol
* Methanol
* Methyl isocyanide
* Pentynylidyne
* Propynal
* Protonated cyanoacetylene

Seven
atoms|

* Acetaldehyde
* Acrylonitrile
* Vinyl cyanide
* Cyanodiacetylene
* Ethylene oxide
* Glycolonitrile
* Hexatriynyl radical
* Methylacetylene
* Methylamine
* Methyl isocyanate
* Vinyl alcohol

Eight
atoms|

* Acetic acid
* Aminoacetonitrile
* Cyanoallene
* Ethanimine
* Glycolaldehyde
* Heptatrienyl radical
* Hexapentaenylidene
* Methylcyanoacetylene
* Methyl formate
* Propenal

Nine
atoms|

* Acetamide
* Cyanohexatriyne
* Cyanotriacetylene
* Dimethyl ether
* Ethanol
* Methyldiacetylene
* Octatetraynyl radical
* Propene
* Propionitrile

Ten
atoms
or more|

* Acetone
* Benzene
* Benzonitrile
* Buckminsterfullerene (C60, C60+, fullerene, buckyball)
* C70 fullerene
* Cyanodecapentayne
* Cyanopentaacetylene
* Cyanotetra-acetylene
* Ethylene glycol
* Ethyl formate
* Methyl acetate
* Methyl-cyano-diacetylene
* Methyltriacetylene
* Propanal
* n-Propyl cyanide
* Pyrimidine

Deuterated
molecules|

* Ammonia
* Ammonium ion
* Formaldehyde
* Formyl radical
* Heavy water
* Hydrogen cyanide
* Hydrogen deuteride
* Hydrogen isocyanide
* Methylacetylene
* N2D+
* Trihydrogen cation

Unconfirmed|

* Anthracene
* Dihydroxyacetone
* Ethyl methyl ether
* Glycine
* Graphene
* H2NCO+
* Linear C5
* Naphthalene cation
* Phosphine
* Pyrene
* Silylidine

Related|

* Abiogenesis
* Astrobiology
* Astrochemistry
* Atomic and molecular astrophysics
* Chemical formula
* Circumstellar envelope
* Cosmic dust
* Cosmic ray
* Cosmochemistry
* Diffuse interstellar band
* Earliest known life forms
* Extraterrestrial life
* Extraterrestrial liquid water
* Forbidden mechanism
* Homochirality
* Intergalactic dust
* Interplanetary medium
* Interstellar medium
* Photodissociation region
* Iron–sulfur world theory
* Kerogen
* Molecules in stars
* Nexus for Exoplanet System Science
* Organic compound
* Outer space
* PAH world hypothesis
* Panspermia
* Polycyclic aromatic hydrocarbon (PAH)
* RNA world hypothesis
* Spectroscopy
* Tholin

* Category:Astrochemistry
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