8-Bromo-1,2,3,4-tetrahydroisoquinoline

Name: 8-Bromo-1,2,3,4-tetrahydroisoquinoline
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 75416-51-2
Cat. No. CS-W005890
Purity≥95%
MDL No.MFCD10001500

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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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8-Bromo-1,2,3,4-tetrahydroisoquinoline|CS-W005890

Structure of 75416-51-2

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General Information

CAS No. 75416-51-2
Cat. No. CS-W005890
Purity ≥95%
MDL No. MFCD10001500
Storage -20°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₀BrN
Molecular Weight 212.09
Synonym(s) 8-BroMo-1,2,3,4-tetrahydroisoquinline
SMILES BrC1=CC=CC2=C1CNCC2

Description

8-Bromo-1,2,3,4-tetrahydroisoquinoline features a bromine substituent at the 8-position of the tetrahydroisoquinoline core, enhancing electrophilic reactivity and enabling direct functionalization in transition-metal-catalyzed couplings. This bench-stable, moisture-tolerant scaffold integrates readily into complex alkaloid architectures and bioactive molecule synthesis, offering high regioselectivity in C–H activation processes.

Application

8-Bromo-1,2,3,4-tetrahydroisoquinoline serves as a versatile building block in medicinal chemistry, enabling efficient access to brominated isoquinoline scaffolds. Its halogenated aromatic ring facilitates palladium-catalyzed cross-coupling reactions, while the saturated nitrogen-containing core offers compatibility with diverse functional groups. The compound exhibits excellent bench stability and ease of purification, making it well-suited for iterative synthesis and late-stage diversification in API development.

Synthesis

Route1
- 252331-63-8
- 726136-49-8
- ~22%
- In-stock
  
  226942-29-6
- In-stock
  
  75416-51-2
References
- WO2008/76954 A2, ; Page/Page column 50 ; WO 2008/076954 A2
Route2
- 75416-47-6
- ~60%
- In-stock
  
  75416-51-2
References
- Mendelson, W. L.; Spainhour, C. B.; Jones, S. S.; Lam, B. L.; Wert, K. L. Tetrahedron Letters, 1980 , vol. 21, p. 1393 - 1396

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 12.03
LogP 2.0948
H_Acceptors 1
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Tetrahydroisoquinoline compounds

Key Words

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8-Bromo-1,2,3,4-tetrahydroisoquinoline

CAS No. 75416-51-2

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