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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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

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

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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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)
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)
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)
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)
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