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Sigma-Aldrich

Allyl iodide

98%

Synonym(s):

3-Iodo-1-propene

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About This Item

Linear Formula:
CH2=CHCH2I
CAS Number:
556-56-9
Molecular Weight:
167.98
Beilstein/REAXYS Number:
1697594
EC Number:
209-130-4
MDL number:
MFCD00001094
UNSPSC Code:
12352100
PubChem Substance ID:
24854295
NACRES:
NA.22

Quality Level

100

assay

98%

form

liquid

contains

copper as stabilizer

refractive index

n20/D 1.554 (lit.)

bp

102-103 °C (lit.)

solubility

alcohol: miscible(lit.)
chloroform: miscible(lit.)
diethyl ether: miscible(lit.)
water: insoluble (practically)(lit.)

density

1.837 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

ICC=C

InChI

1S/C3H5I/c1-2-3-4/h2H,1,3H2

InChI key

HFEHLDPGIKPNKL-UHFFFAOYSA-N

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General description

The interaction of allyl iodide with MoO3, Bi2O3 and molybdates of Bi, Co and Mg has been studied in the temperature range of 270-480°C.

Application

Allyl iodide has been employed as:
  • precursor for generation of allyl radicals to study their recombination in a single pulse shock tube with gas chromatographic measurements
  • reagent used with allylindium sesquiiodide in the cis-double allylation of cyclopropenes

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B

Storage Class

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

60.8 °F - closed cup

flash_point_c

16 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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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Interaction of allyl iodide with molybdate catalysts for the selective oxidation of hydrocarbons.
Grzybowska B, et al.
J. Catal., 49(2), 150-163 (1977)
Aleksandr Fridlyand et al.
The journal of physical chemistry. A, 117(23), 4762-4776 (2013-05-18)
The recombination and disproportionation of allyl radicals has been studied in a single pulse shock tube with gas chromatographic measurements at 1-10 bar, 650-1300 K, and 1.4-2 ms reaction times. 1,5-Hexadiene and allyl iodide were used as precursors. Simulation of
Tsunehisa Hirashita et al.
Organic & biomolecular chemistry, 5(13), 2154-2158 (2007-06-22)
The successive double allylation of cyclopropenes with allylindium sesquiiodide and allyl iodide proceeded with a cis-addition mode in the presence of other organometallics (e.g. Grignard reagent, cuprate, Et(2)Zn and Et(3)Al), giving the corresponding cis-diallylcyclopropanes in high yields.
Xin Ma et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 25(25), 6355-6361 (2019-02-28)
Unexpectedly, the 5-dehydroquinoline radical cation was formed in the gas phase from the 5-iodo-8-nitroquinolinium cation upon ion-trap collision-activated dissociation. This reaction involves the cleavage of a nitro group to generate an intermediate monoradical, namely, the 8-dehydro-5-iodoquinolinium cation, followed by rearrangement
Michael Lesslie et al.
European journal of mass spectrometry (Chichester, England), 21(3), 589-597 (2015-08-27)
Radical migration, both intramolecular and intermolecular, from the tyrosine phenoxyl radical Tyr(O(∙)) to the cysteine radical Cys(S(∙)) in model peptide systems was observed in the gas phase. Ion-molecule reactions (IMRs) between the radical cation of homotyrosine and propyl thiol resulted

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