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294985

Sigma-Aldrich

Allene

≥95%

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Synonym(s):
Propadiene
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)

Quality Level

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

hose barb

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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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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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The silyl-cupration and stannyl-cupration of allenes.
Fleming I, et al.
Tetrahedron, 45(2), 413-424 (1989)
?-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)
Allene.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2007)
Synthetic applications of intramolecular enone-olefin photocycloadditions.
Crimmins M T
Chemical Reviews, 88(8), 1453-1473 (1988)

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