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294985

Sigma-Aldrich

Allene

≥95%

Synonym(s):

Propadiene

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About This Item

Linear Formula:
H2C=C=CH2
CAS Number:
Molecular Weight:
40.06
Beilstein:
1730774
EC Number:
MDL number:
UNSPSC Code:
12142100
PubChem Substance ID:
NACRES:
NA.22

vapor density

1.42 (20 °C, vs air)

vapor pressure

6795 mmHg ( 21 °C)

Assay

≥95%

expl. lim.

13 %

bp

−34 °C (lit.)

mp

−136 °C (lit.)

SMILES string

C=C=C

InChI

1S/C3H4/c1-3-2/h1-2H2

InChI key

IYABWNGZIDDRAK-UHFFFAOYSA-N

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Application

  • Allene is extensively used in a variety of photochemical, thermal, and transition metal-mediated cycloadditions.
  • It can be lithiated to obtain allenyllithium which reacts with alkyl halides to afford terminal allenes.
  • Additional application includes the preparation of reagents such as isopropenylsilanes and isopropenylstannanes by reacting with stannyl and silyl cuprates respectively.

Packaging

Supplied in a carbon steel lecture bottle with a CGA180M/CGA110F needle valve installed.

Compatible with the following:
  • Aldrich® lecture-bottle station systems
  • Aldrich® lecture-bottle gas regulators

Other Notes

Legal Information

Aldrich is a registered trademark of Sigma-Aldrich Co. LLC

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purge valve

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Pictograms

FlameGas cylinder

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Flam. Gas 1 - Press. Gas Liquefied gas

Storage Class Code

2A - Gases

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Versatile allene and carbon dioxide equivalents for the Diels-Alder reaction.
Bonjouklian R and Ruden R A
The Journal of Organic Chemistry, 42(25), 4095-4103 (1977)
?-Cyanocyclobutenone as a highly reactive dienophile in comparison to ?-cyanocyclopentenone.
Bienfait B, et al.
Tetrahedron, 47(38), 8167-8176 (1991)
Simple route to mono-, di-, and tri-substituted allenic compounds.
Linstrumelle G and Michelot D
Journal of the Chemical Society. Chemical Communications, 14, 561-562 (1975)
Synthetic applications of intramolecular enone-olefin photocycloadditions.
Crimmins M T
Chemical Reviews, 88(8), 1453-1473 (1988)
Allene.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2007)

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