1699-52-1

Basic information

• Product Name: N-FORMYL-1,2,3,4-TETRAHYDROISOQUINOLINE
• Synonyms: N-FORMYL-1,2,3,4-TETRAHYDROISOQUINOLINE
• CAS NO: 1699-52-1
• Molecular Formula: C₁₀H₁₁NO
• Molecular Weight: 161.2
• Mol File: 1699-52-1.mol
• Article Data: 61

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-FORMYL-1,2,3,4-TETRAHYDROISOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-FORMYL-1,2,3,4-TETRAHYDROISOQUINOLINE(1699-52-1)
• EPA Substance Registry System: N-FORMYL-1,2,3,4-TETRAHYDROISOQUINOLINE(1699-52-1)

Safety Data

• Hazardous Substances Data: 1699-52-1(Hazardous Substances Data)

Upstream product

• 119-65-3 isoquinoline 
• 64-18-6 formic acid 
• 121-44-8 triethylamine 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 72773-04-7 N-formylbenzotriazole 
• 35452-79-0 N-(3-methyl-2-buten-1-yl)-1,2,3,4-tetrahydroisoquinoline 
• 67-66-3 chloroform 
• 598-30-1 sec.-butyllithium 
• 199480-42-7 1,2,3,4-tetrahydroisoquinolin-2-ylcarbonyl chloride 
• 3230-65-7 3,4-dihydroisoquinoline 
• 77287-34-4 formamide 
• 191545-92-3 1,2,3,4-tetrahydro-2-formyl-4-phenylthioisoquinoline 
• 201230-82-2 carbon monoxide 
• 50-00-0 formaldehyd 

Downstream Products

• 84010-77-5 [1-[(S)-1-(4-Chloro-butyl)-3,4-dihydro-1H-isoquinolin-2-yl]-meth-(E)-ylidene]-((R)-2-phenyl-2-trimethylsilanyloxy-1-trimethylsilanyloxymethyl-ethyl)-amine 
• 3340-78-1 2-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 84010-77-5 [1-[(R)-1-(4-Chloro-butyl)-3,4-dihydro-1H-isoquinolin-2-yl]-meth-(E)-ylidene]-((1S,2S)-2-phenyl-2-trimethylsilanyloxy-1-trimethylsilanyloxymethyl-ethyl)-amine 
• 84010-77-5 [1-[(S)-1-(4-Chloro-butyl)-3,4-dihydro-1H-isoquinolin-2-yl]-meth-(E)-ylidene]-((1S,2S)-2-phenyl-2-trimethylsilanyloxy-1-trimethylsilanyloxymethyl-ethyl)-amine 

Relevant articles and documents

Pd/C-catalyzed reductive formylation of indoles and quinolines using formic acid

A two-step, one-pot domino reaction methodology was developed to synthesize a variety of N-formylindolines and N-formyltetrahydroquinolines from the corresponding indoles and quinolines. In the first step, the heterocyclic compounds are reduced to the corresponding dihydro or tetrahydro products by a Pd/C-catalyzed transfer hydrogenation using formic acid as a hydrogen donor. In the second step, nitrogen is formylated by formic acid to afford the final products in very good isolated yields. Georg Thieme Verlag Stuttgart New York.

Reduction with formic acid. II. Reduction of some N-containing heteroaromatic compounds

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Copper-Catalyzed Formylation of Amines by using Methanol as the C1 Source

Cu/TEMPO catalyst systems are known for the selective transformation of alcohols to aldehydes, as well as for the simultaneous coupling of alcohols and amines to imines under oxidative conditions. In this study, such a Cu/TEMPO catalyst system is found to catalyze the N-formylation of a variety of amines by initial oxidative activation of methanol as the carbonyl source via formaldehyde and formation of N,O-hemiacetals and oxidation of the latter under very mild conditions. A vast range of amines, including aromatic and aliphatic, primary and secondary, and linear and cyclic amines are formylated under these conditions with good to excellent yields. Moreover, paraformaldehyde can be used instead of methanol for the N-formylation.

Selective Iron-Catalyzed N-Formylation of Amines using Dihydrogen and Carbon Dioxide

A family of iron(II) carbonyl hydride species supported by PNP pincer ligands was identified as highly productive catalysts for the N-formylation of amines via CO2 hydrogenation. Specifically, iron complexes supported by two different types of PNP ligands were examined for formamide production. Complexes containing a PNP ligand with a tertiary amine afforded superior turnover numbers in comparison to complexes containing a bifunctional PNP ligand with a secondary amine, indicating that bifunctional motifs are not required for catalysis. Systems incorporating a tertiary amine containing a PNP ligand were active for the N-formylation of a variety of amine substrates, achieving TONs up to 8900 and conversions as high as 92%. Mechanistic experiments suggest that N-formylation occurs via an initial, reversible reduction of CO2 to ammonium formate followed by dehydration to produce formamide. Several intermediates relevant to this reaction pathway, as well as iron-containing deactivation species, were isolated and characterized.

Highly Efficient and Selective N-Formylation of Amines with CO2 and H2 Catalyzed by Porous Organometallic Polymers

The valorization of carbon dioxide (CO2) to fine chemicals is one of the most promising approaches for CO2 capture and utilization. Herein we demonstrated a series of porous organometallic polymers could be employed as highly efficient and recyclable catalysts for this purpose. Synergetic effects of specific surface area, iridium content, and CO2 adsorption capability are crucial to achieve excellent selectivity and yields towards N-formylation of diverse amines with CO2 and H2 under mild reaction conditions even at 20 ppm catalyst loading. Density functional theory calculations revealed not only a redox-neutral catalytic pathway but also a new plausible mechanism with the incorporation of the key intermediate formic acid via a proton-relay process. Remarkably, a record turnover number (TON=1.58×106) was achieved in the synthesis of N,N-dimethylformamide (DMF), and the solid catalysts can be reused up to 12 runs, highlighting their practical potential in industry.