2,3-DIHYDRO-1,4-BENZODIOXINE-5-CARBALDEHYD

Name: 2,3-DIHYDRO-1,4-BENZODIOXINE-5-CARBALDEHYD
Brand: ChemScene
Availability: InStock
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CAS No. 29668-43-7
Cat. No. CS-W000358
Purity≥98%
MDL No.MFCD00239451

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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+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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2,3-DIHYDRO-1,4-BENZODIOXINE-5-CARBALDEHYD|CS-W000358

Structure of 29668-43-7

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General Information

CAS No. 29668-43-7
Cat. No. CS-W000358
Purity ≥98%
MDL No. MFCD00239451
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₈O₃
Molecular Weight 164.16
Synonym(s) 2,3-Dihydro-1,4-benzodioxine-5-carbaldehyde
SMILES O=CC1=C2OCCOC2=CC=C1

Description

2,3-Dihydrobenzo[b][1,4]dioxine-5-carbaldehyde features a rigid, electron-rich dioxane ring fused to a benzene core, delivering enhanced stability and predictable reactivity. The pendant aldehyde group enables direct incorporation into Suzuki-Miyaura couplings, Buchwald-Hartwig aminations, and other C–C or C–heteroatom bond-forming processes. This scaffold serves as a key building block in the synthesis of bioactive heterocycles and functional materials, particularly where planarity and solubility are critical.

Application

2,3-Dihydrobenzo[b][1,4]dioxine-5-carbaldehyde serves as a versatile building block in medicinal chemistry, enabling efficient access to bioactive heterocycles. Its aldehyde functionality facilitates reductive amination, Grignard additions, and Wittig reactions under mild conditions. The rigid, oxygenated bicyclic core provides excellent metabolic stability and favorable pharmacokinetic properties, making it valuable for scaffold hopping and lead optimization in CNS-targeted drug discovery.

Synthesis

Route1
- In-stock
  
  24677-78-9
- 106-93-4
- ~89%
- In-stock
  
  29668-43-7
References
- Grudzien, Krzysztof; Malinska, Maura; Barbasiewicz, Michal Organometallics, 2012 , vol. 31, # 9 p. 3636 - 3646
Route2
- In-stock
  
  274910-19-9
- ~88%
- In-stock
  
  29668-43-7
References
- Allergan, Inc. Patent: US2006/69144 A1, 2006 ; Location in patent: Page/Page column 19-20 ; US 20060069144 A1
Route3
- In-stock
  
  624-73-7
- In-stock
  
  24677-78-9
- ~93%
- In-stock
  
  29668-43-7
References
- Deveau, Amy Morin; Macdonald, Timothy L. Tetrahedron Letters, 2004 , vol. 45, # 4 p. 803 - 807

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H319-H412
Precautionary Statements : P264-P273-P280-P501

Quality Control

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Computational Chemistry Data

TPSA 35.53
LogP 1.2703
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Benzodioxane compounds

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2,3-DIHYDRO-1,4-BENZODIOXINE-5-CARBALDEHYD

CAS No. 29668-43-7

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