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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:
463-49-0
Molecular Weight:
40.06
Beilstein/REAXYS Number:
1730774
EC Number:
207-335-3
MDL number:
MFCD00008566
UNSPSC Code:
12142100
PubChem Substance ID:
24857749
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

See Technical Information Bulletin AL-151 Gas Regulators: Selection, Installation, and Operation

Legal Information

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

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pictograms

FlameGas cylinder
GHS02,GHS04

signalword

Danger

hcodes

H220,H280

Hazard Classifications

Flam. Gas 1 - Press. Gas Liquefied gas

Storage Class

2A - Gases

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, multi-purpose combination respirator cartridge (US)

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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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)
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Allenes are molecules based on three carbons connected by two cumulated carbon-carbon double bonds. Given their axially chiral nature and unique reactivity, substituted allenes have a variety of applications in organic chemistry as key synthetic intermediates and directly as part
David Tejedor et al.
Chemical Society reviews, 42(2), 458-471 (2012-10-05)
The propargyl Claisen rearrangement is a known protocol to gain access to functionalized allenes through the [3,3]-sigmatropic transformation of propargyl vinyl ethers. The correct use of appropriate propargyl vinyl ethers as starting materials coupled with suitable reaction conditions can aid
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