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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
Recommended Products
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:
Compatible with the following:
- Aldrich® lecture-bottle station systems
- Aldrich® lecture-bottle gas regulators
Other Notes
See Technical Information Bulletin AL-151 Gas Regulators: Selection, Installation, and Operation
Legal Information
Aldrich is a registered trademark of Sigma-Aldrich Co. LLC
also commonly purchased with this product
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control valve
hose barb
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purge valve
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recommended
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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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?-Cyanocyclobutenone as a highly reactive dienophile in comparison to ?-cyanocyclopentenone.
Bienfait B, et al.
Tetrahedron, 47(38), 8167-8176 (1991)
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)
Cale D Weatherly et al.
Organic letters, 14(7), 1704-1707 (2012-03-22)
The synthesis of 1,3-diaminated stereotriads via the bis-aziridination of allenes is reported. The reactive 1,4-diazaspiro[2.2]pentane intermediates undergo a mild Brønsted acid-promoted rearrangement to yield 1,3-diaminated ketones in good yields with excellent stereocontrol. Directed reduction of the ketone can be achieved
Fanke Meng et al.
Organic letters, 15(6), 1414-1417 (2013-03-07)
Two types of NHC-Cu complexes catalyze protoborations of terminal allenes to afford valuable 1,1- or trisubstituted vinylboron species with high site selectivity and stereoselectivity. The scope of the method, application to natural product synthesis, and mechanistic basis for the observed
Anthony Pitaval et al.
Organic letters, 15(17), 4580-4583 (2013-08-22)
Gold(I)-catalyzed allene-vinylcyclopropane cycloisomerization leads to the tricyclic framework of the protoilludanes in a single step by a reaction that involves a cyclopropane ring expansion and a Prins cyclization.
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