5-Hydroxy-2,2-dimethyl-2H-chromene-6-carbaldehyde

Name: 5-Hydroxy-2,2-dimethyl-2H-chromene-6-carbaldehyde
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CAS No. 54287-99-9
Cat. No. CS-0153819
Purity≥98%
MDL No.MFCD08705718

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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5-Hydroxy-2,2-dimethyl-2H-chromene-6-carbaldehyde|CS-0153819

Structure of 54287-99-9

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General Information

CAS No. 54287-99-9
Cat. No. CS-0153819
Purity ≥98%
MDL No. MFCD08705718
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₂O₃
Molecular Weight 204.22
Synonym(s) formyl 2,2-dimethyl-chromen
SMILES CC1(C)C=CC2=C(C=CC(=C2O)C=O)O1

Description

5-Hydroxy-2,2-dimethyl-2H-chromene-6-carbaldehyde features a sterically hindered chromene core with a phenolic hydroxyl and aldehyde functional group in close proximity. This arrangement enables direct participation in condensation reactions and facilitates the construction of complex heterocyclic architectures under mild conditions.

Application

5-Hydroxy-2,2-dimethyl-2H-chromene-6-carbaldehyde serves as a versatile scaffold for the synthesis of bioactive heterocycles, enabling efficient derivatization via aldol condensations and nucleophilic additions. Its phenolic hydroxyl and aldehyde functionalities provide orthogonal reactivity for selective functionalization, while the dimethyl-substituted chromene core enhances stability and facilitates purification. This compound functions as a key building block in the construction of natural product analogs and pharmaceutical intermediates.

Synthesis

Route1
- In-stock
  
  107-86-8
- In-stock
  
  95-01-2
- ~59%
- In-stock
  
  54287-99-9
References
- Shi, Zhuangzhi; Schroeder, Nils; Glorius, Frank Angewandte Chemie - International Edition, 2012 , vol. 51, # 32 p. 8092 - 8096
Route2
- 32268-30-7
- ~%
- In-stock
  
  54287-99-9
References
- Nomura, Taro; Fukai, Toshio; Hano, Yoshio; Tsukamoto, Koji Heterocycles, 1983 , vol. 20, # 4 p. 661 - 666
Route3
- 54287-98-8
- ~99%
- In-stock
  
  54287-99-9
References
- Garcia, Jose; Barluenga, Sofia; Beebe, Kristin; Neckers, Len; Winssinger, Nicolas Chemistry - A European Journal, 2010 , vol. 16, # 32 p. 9767 - 9771

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-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 46.53
LogP 2.3889
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Aldehyde

Building Blocks Skeleton Aromatic heterocycle compounds Other aromatic heterocycles compounds

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5-Hydroxy-2,2-dimethyl-2H-chromene-6-carbaldehyde

CAS No. 54287-99-9

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