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Description
TCI D4629 is 6,7-Dimethoxy-3,4-dihydroisoquinoline Hydrochloride, the hydrochloride salt of a cyclic imine built on a dihydroisoquinoline framework carrying two methoxy groups at the 6 and 7 positions. It is a well-established heterocyclic building block in alkaloid synthesis, because the dimethoxy substitution pattern on its aromatic ring mirrors a motif found widely across naturally occurring isoquinoline alkaloids. In organic chemistry laboratories, this compound serves as a key intermediate, typically obtained through Bischler–Napieralski cyclisation and then elaborated further into substituted tetrahydroisoquinolines.
The synthetic value of this material comes from the carbon–nitrogen double bond within its ring, which is electrophilic at the imine carbon and therefore primed for nucleophilic attack. From this point, researchers can carry out reduction to the corresponding cyclic amine, addition of organometallic reagents, or Pictet–Spengler and Mannich reactions to construct more elaborate polycyclic frameworks. The hydrochloride salt form offers a practical advantage as well: the free imine is relatively prone to hydrolysis and tends to polymerise, whereas the salt form is more stable in storage and easier to handle on the bench.
In Indonesian laboratories, this building block is typically used in university and institutional research groups working on natural product synthesis, medicinal chemistry, and heterocyclic methodology. It suits work in which an isoquinoline core must be assembled step by step, and its stable salt form is well matched to local laboratory conditions, where reagents are often stored for a period between experiments before being taken through the next stage of a synthetic sequence.
Laboratory Applications
Alkaloid total synthesis — the 6,7-dimethoxy pattern reproduces a motif common to natural isoquinoline alkaloids, giving a direct entry into those target skeletons.
Preparation of substituted tetrahydroisoquinolines — the ring C=N bond can be reduced to the corresponding cyclic amine, a standard downstream transformation from this intermediate.
Pictet–Spengler chemistry — the electrophilic imine carbon participates readily in this classical condensation used to build fused polycyclic isoquinoline architectures.
Mannich-type reactions — the same reactive carbon–nitrogen double bond allows construction of more complex polycyclic frameworks from a single common intermediate.
Organometallic addition studies — nucleophilic organometallic reagents add at the imine carbon, letting researchers install new substituents onto the dihydroisoquinoline core.
Specifications
Brand: TCI
CAS Number: 20232-39-7
Chemical name: 6,7-Dimethoxy-3,4-dihydroisoquinoline Hydrochloride
Category: Chemistry > Building Blocks > Heterocyclic Building Blocks
Pack sizes: available in the standard catalogue pack sizes offered by TCI for this item
Storage: store as a hydrochloride salt, which is more stable in storage than the corresponding free imine
Handling and Storage
Store the container tightly closed in a cool, dry place, away from moisture and from direct sunlight. Because the free imine is susceptible to hydrolysis, keeping the material sealed and protected from atmospheric humidity is important for preserving its quality between uses. Use tightly closed glass or chemically compatible containers, and reseal immediately after weighing out portions. Handle the compound in a fume hood using standard laboratory personal protective equipment, including safety glasses, gloves, and a laboratory coat. Avoid the generation of dust during transfer and weighing, and follow your institution's chemical waste procedures for the disposal of residues and contaminated consumables. Always consult the manufacturer's safety data sheet before first use.
