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Merck
CN

294985

Allene

≥95%

Synonym(s):

Propadiene

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About This Item

Linear Formula:
H2C=C=CH2
CAS Number:
Molecular Weight:
40.06
UNSPSC Code:
12142100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
207-335-3
Beilstein/REAXYS Number:
1730774
MDL number:
Assay:
≥95%
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InChI key

IYABWNGZIDDRAK-UHFFFAOYSA-N

InChI

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

SMILES string

C=C=C

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.)

Quality Level

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

pictograms

FlameGas cylinder

signalword

Danger

hcodes

Hazard Classifications

Flam. Gas 1 - Press. Gas Liquefied gas

Storage Class

2A - Gases

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Regulatory Information

监管及禁止进口产品
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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)
The silyl-cupration and stannyl-cupration of allenes.
Fleming I, et al.
Tetrahedron, 45(2), 413-424 (1989)
Gold(I)-catalyzed stereoconvergent, intermolecular enantioselective hydroamination of allenes.
Kristina L Butler et al.
Angewandte Chemie (International ed. in English), 51(21), 5175-5178 (2012-04-12)
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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