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550779

Sigma-Aldrich

2-Iodobenzaldehyde

97%

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About This Item

Linear Formula:
IC6H4CHO
CAS Number:
26260-02-6
Molecular Weight:
232.02
MDL number:
MFCD00039570
UNSPSC Code:
12352100
PubChem Substance ID:
24879145
NACRES:
NA.22

assay

97%

mp

36-39 °C (lit.)

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.

Application

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

pictograms

Exclamation mark
GHS07

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

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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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)
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)
2-Iodobenzaldehyde.
Betz R and Klufers P.
Acta Crystallographica Section E, Structure Reports Online, 63(12), o4879-o4879 (2007)
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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