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779385

Sigma-Aldrich

3,4-Dihydroisoquinoline

≥97.5% (GC)

Synonym(s):

3,4-Dihydroisoquinoline

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About This Item

Empirical Formula (Hill Notation):
C9H9N
CAS Number:
3230-65-7
Molecular Weight:
131.17
EC Number:
221-769-0
MDL number:
MFCD00033714
UNSPSC Code:
12352100
PubChem Substance ID:
329768033
NACRES:
NA.22

Quality Level

100

Assay

≥97.5% (GC)
97.5-102.5% (T)

form

solid

suitability

complies for identity (IR)

SMILES string

C1Cc2ccccc2C=N1

InChI

1S/C9H9N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-4,7H,5-6H2

InChI key

NKSZCPBUWGZONP-UHFFFAOYSA-N

Application

3,4-Dihydroisoquinoline can be used as a reactant to synthesize:
  • 5,6-Dihydro-8H-isoquino[1,2-b]quinazolin-8-one by decarboxylative cyclization reaction with isatoic anhydride using tetrabutylammonium iodide (TBAI).
  • 1-naphtholyl tetrahydroisoquinoline by aza-Friedel-Crafts reaction with various naphthols.
  • 3,4-dihydroisoquinoline pseudo bases, which are employed as starting materials for the preperation of 3-benzazepine derivatives.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H302,H310,H315,H319

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK6145
BCCD3026
STBJ8357
STBG6722
STBG6646

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Solvent-free direct aza-Friedel-Crafts reactions between 3, 4-dihydroisoquinoline and 1-or 2-naphthols
MacLeod PD, et al.
Tetrahedron Letters, 47(38), 6791-6794 (2006)
Electrosynthesis of polycyclic quinazolinones and rutaecarpine from isatoic anhydrides and cyclic amines
Chen Xingyu, et al.
Royal Society of Chemistry Advances, 10(72), 44382-44386 (2020)
A facile, one pot method for the synthesis of 4-acyl-1, 2-dihydro-3-benzazepines, based on the ring expansion of natural and synthetic 3, 4-dihydroisoquinoline pseudo bases
Kartsev VG, et al.
Tetrahedron Letters, 56(50), 6988-6993 (2015)

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