6-Bromo-1,2,3,4-tetrahydroquinoline

Name: 6-Bromo-1,2,3,4-tetrahydroquinoline
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 22190-35-8
Cat. No. CS-W019748
Purity≥96%
MDL No.MFCD04966989

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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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6-Bromo-1,2,3,4-tetrahydroquinoline|CS-W019748

Structure of 22190-35-8

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General Information

CAS No. 22190-35-8
Cat. No. CS-W019748
Purity ≥96%
MDL No. MFCD04966989
Storage RT, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₀BrN
Molecular Weight 212.09
Synonym(s) None
SMILES BrC1=CC=C(NCCC2)C2=C1

Description

6-Bromo-1,2,3,4-tetrahydroquinoline features a brominated tetrahydroquinoline core with enhanced reactivity at the C6 position. This bench-stable heterocycle integrates readily into cross-coupling reactions and serves as a key scaffold in medicinal chemistry and materials synthesis.

Application

6-Bromo-1,2,3,4-tetrahydroquinoline serves as a versatile building block in medicinal chemistry and synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions due to its stable bromo functionality. The tetrahydroquinoline core provides a rigid, electron-rich scaffold suitable for late-stage functionalization and incorporation into bioactive molecules. Its bench-stable nature and compatibility with diverse reaction conditions facilitate efficient synthesis of heterocyclic compounds and drug candidates.

Synthesis

Route1
- In-stock
  
  635-46-1
- ~61%
- In-stock
  
  22190-35-8
References
- Marchand, Pascal; Puget, Alain; Le Baut, Guillaume; Emig, Peter; Czech, Michael; Guenther, Eckhard Tetrahedron, 2005 , vol. 61, # 16 p. 4035 - 4041
Route2
- In-stock
  
  3279-90-1
- ~%
- In-stock
  
  22190-35-8
References
- US2004/220206 A1, ; Page 24; 32 ; US 20040220206 A1
Route3
- In-stock
  
  76228-06-3
- ~30%
- In-stock
  
  22190-35-8
References
- Varnes, Jeffrey G.; Wacker, Dean A.; Jacobson, Irina C.; Quan, Mimi L.; Ellis, Christopher D.; Rossi, Karen A.; He, Ming Y.; Luettgen, Joseph M.; Knabb, Robert M.; Bai, Steven; He, Kan; Lam, Patrick Y.S.; Wexler, Ruth R. Bioorganic and Medicinal Chemistry Letters, 2007 , vol. 17, # 23 p. 6481 - 6488

Safety Information

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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 12.03
LogP 2.8072
H_Acceptors 1
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Tetrahydroquinoline compounds

Key Words

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6-Bromo-1,2,3,4-tetrahydroquinoline

CAS No. 22190-35-8

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