(R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

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

CAS No. 180272-45-1
Cat. No. CS-M0032
Purity≥98%
MDL No.MFCD11858641

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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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(R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline|CS-M0032

Structure of 180272-45-1

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General Information

CAS No. 180272-45-1
Cat. No. CS-M0032
Purity ≥98%
MDL No. MFCD11858641
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₁₅N
Molecular Weight 209.29
Synonym(s) (1R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
SMILES [C@@H]1(C2=CC=CC=C2)C3=CC=CC=C3CCN1

Description

(R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline is a chiral heterocyclic scaffold featuring a rigid, electron-rich aromatic system fused to a saturated nitrogen-containing ring. This configuration imparts high enantioselectivity in asymmetric synthesis and serves as a key structural motif in bioactive alkaloid analogs. The compound exhibits excellent stability under standard bench conditions and integrates readily into medicinal chemistry campaigns targeting CNS-directed therapeutics.

Application

(R)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline serves as a well-established chiral building block in medicinal chemistry, enabling the synthesis of bioactive alkaloids and CNS-targeted pharmaceuticals. Its stereogenic center at C1 provides predictable stereochemical control in downstream transformations, while the tetrahydroisoquinoline core exhibits favorable metabolic stability and membrane permeability. The compound demonstrates robust bench stability, tolerates common functional groups, and participates reliably in Pd-catalyzed coupling reactions and electrophilic substitutions, facilitating efficient route design for complex heterocyclic scaffolds.

Synthesis

Route1
- In-stock
  
  52250-50-7
- ~%
- In-stock
  
  22990-19-8
- In-stock
  
  180272-45-1
References
- Journal of Medicinal Chemistry, , vol. 48, # 21 p. 6597 - 6606
Route2
- 220936-57-2
- ~97%
- In-stock
  
  180272-45-1
References
- Berhal, Farouk; Wu, Zi; Zhang, Zhaoguo; Ayad, Tahar; Ratovelomanana-Vidal, Virginie Organic Letters, 2012 , vol. 14, # 13 p. 3308 - 3311
Route3
- 1443308-76-6
- ~95%
- In-stock
  
  180272-45-1
References
- Ye, Zhi-Shi; Guo, Ran-Ning; Cai, Xian-Feng; Chen, Mu-Wang; Shi, Lei; Zhou, Yong-Gui Angewandte Chemie - International Edition, 2013 , vol. 52, # 13 p. 3685 - 3689 Angew. Chem., 2013 , vol. 125, # 13 p. 3773 - 3777,5

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 2.9217
H_Acceptors 1
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Tetrahydroisoquinoline compounds

Chemical Biology Pharmaceutical Development and Drug Discovery Research Reagents Building Blocks for Pharmaceutical Ingredients

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(R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

CAS No. 180272-45-1

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