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238325

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.)

functional group

alkyl halide
iodo

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCS8833
MKCR6970
MKCQ7060
MKCN9231
MKCM1182

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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.
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
Interaction of allyl iodide with molybdate catalysts for the selective oxidation of hydrocarbons.
Grzybowska B, et al.
J. Catal., 49(2), 150-163 (1977)
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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