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183636

Sigma-Aldrich

2-Iodobenzyl alcohol

98%

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About This Item

Linear Formula:
IC6H4CH2OH
CAS Number:
5159-41-1
Molecular Weight:
234.03
Beilstein:
2079487
EC Number:
225-933-2
MDL number:
MFCD00004610
UNSPSC Code:
12352100
PubChem Substance ID:
24851064
NACRES:
NA.22

Assay

98%

mp

89-92 °C (lit.)

functional group

hydroxyl
iodo

SMILES string

OCc1ccccc1I

InChI

1S/C7H7IO/c8-7-4-2-1-3-6(7)5-9/h1-4,9H,5H2

InChI key

WZCXOBMFBKSSFA-UHFFFAOYSA-N

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Application

2-Iodobenzyl alcohol was used in the synthesis of:
  • substituted seven-membered lactones
  • 2-[(E)-(1′-iodo-2′-propenyl)]benzyl alcohol
  • 2,3-diphenyl-1-indenone

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW4687
MKBQ9969V
MKCL4476
MKCC4701
16925LH

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Dinesh Kumar Rayabarapu et al.
Journal of the American Chemical Society, 124(20), 5630-5631 (2002-05-16)
A new class of substituted seven-membered lactones 3 were conveniently synthesized via cyclization of o-iodobenzyl alcohol 1 (o-IC(6)H(4)CH(2)OH) with various propiolates 2 (RC triple bond CCOOMe) in the presence of Ni(dppe)Br(2) and Zn powder in acetonitrile at 80 degrees C.
Synthesis of indenones via palladium-catalyzed annulation of internal alkynes.
Larock RC, et al.
The Journal of Organic Chemistry, 58(17), 4579-4583 (1993)
Guangwei Wang et al.
Journal of organometallic chemistry, 692(21), 4731-4736 (2007-10-01)
The Zr-catalyzed methylalumination of heterosubstituted arylethynes containing O, S, Cl, and Si can proceed in high yields (>70%) and in a highly regio- and stereoselective manner (≥98-99%), although SO(2)Ph, Br, and Cl in a benzylic position present serious chemoselectivity-related problems.

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