1,4-Dihydro-1,4-methanonaphthalene

Name: 1,4-Dihydro-1,4-methanonaphthalene
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 4453-90-1
Cat. No. CS-B0002
Purity≥98%
MDL No.MFCD00213597

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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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1,4-Dihydro-1,4-methanonaphthalene|CS-B0002

Structure of 4453-90-1

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General Information

CAS No. 4453-90-1
Cat. No. CS-B0002
Purity ≥98%
MDL No. MFCD00213597
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₀
Molecular Weight 142.20
Synonym(s) Tricyclo[6.2.1.02,7]undeca-2,4,6,9-tetraene
SMILES C12C3=CC=CC=C3C(C=C2)C1

Description

1,4-Dihydro-1,4-methanonaphthalene features a rigid, fused bicyclic structure with localized diene character, enabling participation in Diels-Alder cycloadditions. This bench-stable, moisture-tolerant intermediate integrates readily into synthetic sequences requiring controlled reactivity and defined stereochemistry.

Application

1,4-Dihydro-1,4-methanonaphthalene serves as a versatile bicyclic building block in synthetic organic chemistry, offering enhanced rigidity and defined stereochemistry. Its stable dihydroaromatic core facilitates functionalization at the olefinic positions and enables selective transformations under standard catalytic conditions. The molecule functions effectively in transition-metal-catalyzed couplings and serves as a scaffold for heterocyclic systems and complex molecular architectures relevant to medicinal chemistry and materials science.

Synthesis

Route1
- In-stock
  
  1072-85-1
- 542-92-7
- ~65%
- In-stock
  
  4453-90-1
References
- Fernandez, Franco; Garcia-Mera, Xerardo; Morales, Melvin; Rodriguez-Borges, Jose E.; De Clercq, Eric Synthesis, 2002 , # 8 p. 1084 - 1090
Route2
- 542-92-7
- 583-53-9
- ~90%
- In-stock
  
  4453-90-1
References
- Brooks, Paige R.; Caron, Stephane; Coe, Jotham W.; Ng, Karl K.; Singer, Robert A.; Vazquez, Enrique; Vetelino, Michael G.; Watson Jr., Harry H.; Whritenour, David C.; Wirtz, Michael C. Synthesis, 2004 , # 11 p. 1755 - 1758
Route3
- In-stock
  
  583-55-1
- 542-92-7
- ~99%
- In-stock
  
  4453-90-1
References
- Kawabata, Hiroshi; Nishino, Toshiki; Nishiyama, Yutaka; Sonoda, Noboru Tetrahedron Letters, 2002 , vol. 43, # 28 p. 4911 - 4913

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-P280-P330

Quality Control

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Computational Chemistry Data

TPSA 0
LogP 2.8273
H_Acceptors 0
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Bridge Rings compounds Other bridge ring compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Material Science Polymer/Macromolecule Reagents Monomers Cyclic Olefin Monomers

Key Words

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1,4-Dihydro-1,4-methanonaphthalene

CAS No. 4453-90-1

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