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550779

Sigma-Aldrich

2-Iodobenzaldehyde

97%

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About This Item

Linear Formula:
IC6H4CHO
CAS Number:
Molecular Weight:
232.02
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

mp

36-39 °C (lit.)

functional group

aldehyde
iodo

storage temp.

2-8°C

SMILES string

Ic1ccccc1C=O

InChI

1S/C7H5IO/c8-7-4-2-1-3-6(7)5-9/h1-5H

InChI key

WWKKTHALZAYYAI-UHFFFAOYSA-N

General description

2-Iodobenzaldehyde (o-iodobenzaldehyde) is a 2-halobenzaldehyde derivative. Its crystals belong to the orthorhombic crystal system and P212121 space group.[1]

Application

2-Iodobenzaldehyde may be used as a reactant in the synthesis of the following heterocycles:
  • 2,3-diaryl-1-indenones[2]
  • indolo[1,2-a]quinazolines[3]
  • Baylis-Hillman (BH) adducts[4]
It may also be used in preparing:
  • 5-phenylindazolo[3,2-b]quinazolin-7(5H)-one[5]
  • 4-(3-iodophenyl)-2,2:6,2-terpyridine[6]
  • fluoren-9-one[7]
  • 2-formyl-3′-methoxybiphenyl[8]

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Combined catalysis: Pd-catalyzed two-step one-pot protocol for 2, 3-diaryl-1-indenones involving domino synthesis of diarylacetylenes and Heck-Larock annulations.
Rao MLN and Dhanorkar RJ.
Tetrahedron, 70(43), 8067-8078 (2014)
Self-Assembly of Shape-Persistent Hexagonal Macrocycles with Trimeric Bis (terpyridine)-FeII Connectivity.
Li S, et al.
European Journal of Organic Chemistry, 2008(19), 3328-3334 (2008)
Synthesis of indanones via intramolecular Heck reaction of Baylis-Hillman adducts of 2-iodobenzaldehyde.
Park JB, et al.
Bull. Korean Chem. Soc., 25(6), 927-930 (2004)
Copper (I)-Catalyzed Synthesis of 5-Arylindazolo [3, 2-b] quinazolin-7 (5 H)-one via Ullmann-Type Reaction
Chen DS, et al.
The Journal of Organic Chemistry, 78(11), 5700-5704 (2013)
Ring-Closing Olefin Metathesis of 2, 2'-Divinylbiphenyls: A Novel and General Approach to Phenanthrenes.
Iuliano A, et al.
Organic Letters, 6(21), 3711-3714 (2004)

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