3-(tert-Butyl)-2-hydroxy-5-iodobenzaldehyde

Name: 3-(tert-Butyl)-2-hydroxy-5-iodobenzaldehyde
Brand: ChemScene
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CAS No. 83816-59-5
Cat. No. CS-0132295
Purity≥95%
MDL No.MFCD27929482

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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3-(tert-Butyl)-2-hydroxy-5-iodobenzaldehyde|CS-0132295

Structure of 83816-59-5

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General Information

CAS No. 83816-59-5
Cat. No. CS-0132295
Purity ≥95%
MDL No. MFCD27929482
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₃IO₂
Molecular Weight None
Synonym(s) 3-Tert-butyl-5-iodosalicylaldehyde
SMILES O=CC1=CC(I)=CC(C(C)(C)C)=C1O

Description

This bench-stable aldehyde features a sterically hindered tert-butyl group and a reactive hydroxy-iodo substitution pattern, enabling selective functionalization in complex synthesis. The para-hydroxyl group enhances solubility and facilitates downstream derivatization, while the iodine moiety serves as a high-efficiency coupling handle.

Application

3-(tert-Butyl)-2-hydroxy-5-iodobenzaldehyde serves as a versatile building block for the synthesis of functionalized aromatic scaffolds, enabling palladium-catalyzed cross-coupling reactions due to its iodide functionality. The ortho-hydroxyl group facilitates chelation in transition metal catalysis and enhances solubility, while the tert-butyl group provides steric protection and bench stability. Its defined reactivity profile supports efficient downstream derivatization in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  24623-65-2
- ~99%
- In-stock
  
  83816-59-5
References
- Park, Jongwoo; Lang, Kai; Abboud, Khalil A.; Hong, Sukwon Journal of the American Chemical Society, 2008 , vol. 130, # 49 p. 16484 - 16485
Route2
- 88-18-6
- ~%
- In-stock
  
  83816-59-5
References
- Tramposch, Kenneth M.; Kung, Hank F.; Blau, Monte Journal of Medicinal Chemistry, 1983 , vol. 26, # 2 p. 121 - 125

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H312-H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P363-P501

Quality Control

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Computational Chemistry Data

TPSA 37.3
LogP 3.1068
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Phenol

Material Science Covalent Organic Frameworks Aldehyde COFs Linkers

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Material Science Material Building Blocks Covalent Organic Frameworks (COFs) Linkers Aldehyde Linkers

Material Science Polymer/Macromolecule Reagents Covalent Organic Frameworks (COFs) Linkers Aldehyde Linkers

Key Words

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3-(tert-Butyl)-2-hydroxy-5-iodobenzaldehyde

CAS No. 83816-59-5

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