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464147

Sigma-Aldrich

3-Iodo-4,5-dimethoxybenzaldehyde

97%

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About This Item

Linear Formula:
IC6H2(OCH3)2CHO
CAS Number:
32024-15-0
Molecular Weight:
292.07
MDL number:
MFCD00674091
UNSPSC Code:
12352100
PubChem Substance ID:
24870143
NACRES:
NA.22

Assay

97%

mp

69-72 °C (lit.)

functional group

aldehyde
iodo

SMILES string

COc1cc(C=O)cc(I)c1OC

InChI

1S/C9H9IO3/c1-12-8-4-6(5-11)3-7(10)9(8)13-2/h3-5H,1-2H3

InChI key

MVPNBXPAUYYZAF-UHFFFAOYSA-N

General description

3-Iodo-4,5-dimethoxybenzaldehyde is an aryl iodide having an aldehyde group. It can be synthesized starting from 3,4-dihydroxy-5-iodobenzaldehyde.

Application

3-Iodo-4,5-dimethoxybenzaldehyde was used in the preparation of 3-iodo-4,4′,5-trimethoxy-3′-O-tert-butyldiphenylsilyl-Z-stilbene and 3-iodo-4,4′,5-trimethoxy-3′-O-tert-butyldiphenylsilyl-E-stilbene. It may be used for the synthesis of chloropeptin I and chloropeptin II.

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

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Certificates of Analysis (COA)

Lot/Batch Number
07024JJ
00103PD
13228MQ

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Nucleophilic catalysis of the iodine-zinc exchange reaction: preparation of highly functionalized diaryl zinc compounds.
Florian F Kneisel et al.
Angewandte Chemie (International ed. in English), 43(8), 1017-1021 (2004-02-18)
George R Pettit et al.
Journal of natural products, 75(3), 385-393 (2012-02-14)
Toward the objective of designing a structurally modified analogue of the combretastatin A-4 phosphate prodrug (1b) with the potential for increased specificity toward thyroid carcinoma, synthesis of a series of iodocombstatin phosphate (11a-h) and diiodocombstatin phosphate prodrugs (12a-h) has been
Joie Garfunkle et al.
Journal of the American Chemical Society, 131(44), 16036-16038 (2009-10-21)
The first total synthesis of chloropeptin II (1, complestatin) is disclosed. Key elements of the approach include the use of an intramolecular Larock indole synthesis for the initial macrocyclization, adopting conditions that permit utilization of a 2-bromoaniline, incorporating a terminal
Approaches to iodinated derivatives of vanillin and isovanillin.
Nammalwar B, et al.
Organic preparations and procedures international, 44(2), 146-146 (2012)

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