91-21-4

Basic information

• Product Name: 1,2,3,4-TETRAHYDROISOQUINOLINE
• Synonyms: 1,2,3,4-Tetrahydro-2-azanaphthalene;1,2,3,4-Tetrahydro-2-isoquinoline;1,2,3,4-tetrahydro-isoquinolin;Tetrahydroisoquinoline;LABOTEST-BB LTBB000776;AKOS BB-9293;1,2,3,4-TETRAHYDROISOQUINOLINE;1,2,3,4-Tetrahydro-#niso-quinoline
• CAS NO: 91-21-4
• Molecular Formula: C₉H₁₁N
• Molecular Weight: 133.19
• EINECS: 202-050-0
• Product Categories: Quinoline&Isoquinoline;Building Blocks;Heterocyclic Building Blocks;Isoquinolines;Bioactive Small Molecules;Building Blocks;Cell Biology;Chemical Synthesis;Heterocyclic Building Blocks;T
• Mol File: 91-21-4.mol
• Article Data: 153

Chemical Properties

• Melting Point: −30 °C(lit.)
• Boiling Point: 232-233 °C(lit.)
• Flash Point: 210 °F
• Appearance: Clear yellow to brown/Liquid
• Density: 1.064 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0588mmHg at 25°C
• Refractive Index: n20/D 1.568(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 20g/l
• PKA: 9.66±0.20(Predicted)
• Water Solubility: Soluble in water at 20°C 20g/L.
• BRN: 116156
• CAS DataBase Reference: 1,2,3,4-TETRAHYDROISOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-TETRAHYDROISOQUINOLINE(91-21-4)
• EPA Substance Registry System: 1,2,3,4-TETRAHYDROISOQUINOLINE(91-21-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: NX4900000
• TSCA: Yes
• Hazardous Substances Data: 91-21-4(Hazardous Substances Data)

Usage

Synthesis

To a solution of the isoquinolinone (1.156 g, 9.90 mmol) and tert-butyl alcohol (0.88 mL, 11.9 mmol) in THF (30 mL) at ?78 °C was added liquid ammonia (about 280 mL). Lithium was added in small pieces until the blue coloration persisted, after which the solution was stirred at ?78 °C for 30 min. The blue coloration was dissipated with piperlyne, 4-methoxybenzyl chloride (4.83 g, 31.00 mmol) in THF (5 mL) was introduced by syringe, and the mixture was stirred for an additional 150 min at ?78 °C. Solid ammonium chloride was added and then the ammonia was allowed to evaporate. The pale yellow residue was partitioned between CH2Cl2 (30 mL) and water (40 mL). The layers were separated, and the aqueous layer was extracted with CH2Cl2 (2 × 30 mL). The combined organic layers were washed with 10% sodium thiosulfate solution (20 mL), dried over magnesium sulfate, and concentrated. Flash chromatography (EtOAc:hexane, 2:1) on silica gave 2.21 g (75%) of the tetrahydroisoquinolinone.??Reference: Schultz, A. G.; Guzi, T. J.; Larsson, E.; Rahm, R.; Thakker, K. Bidlack, J. M. J. Org. Chem. 1998, 63, 7795–7804.

Description

1, 2, 3, 4-TETRAHYDROISOQUINOLINE belongs to tetrahydroisoquinoline compound, which is encountered in a number of drugs, tubocurarine, one of the quaternary ammonium muscle relaxants1-3. It is used as a reagent in the preparation of4-(1, 2, 4-oxadiazol-5-yl) piperidine-1-carboxamides as antiproliferative tubulin inhibitors1. It can be used for the synthesis of 1, 2, 3, 4-tetrahydroisoquinoline-3-carboxylic acid (Tic), which has strong applications in peptides and peptidomimetics design and discovery2. 1, 2, 3, 4-tetrahydroisoquinoline has been made into some derivatives with potential for prevention of parkinsonism4, cancer treatment5 and acting as Anticonvulsant Agents6.

Reference

https://www.alfa.com/en/catalog/L08143/ https://www.ncbi.nlm.nih.gov/pubmed/21235510 https://en.wikipedia.org/wiki/Tetrahydroisoquinoline Okuda, K, Y. Kotake, and S. Ohta. "Parkinsonism-preventing activity of 1-methyl-1, 2, 3, 4-tetrahydroisoquinoline derivatives in C57BL mouse in vivo. Biological & Pharmaceutical Bulletin 29.7(2006):1401-1403. Luca, Laura De, et al. "3D Pharmacophore Models for 1, 2, 3, 4‐Tetrahydroisoquinoline Derivatives Acting as Anticonvulsant Agents." Archiv Der Pharmazie 339.7(2006):388-400. Hatano, H, et al. "Tumor-specific cytotoxic activity of 1, 2, 3, 4-tetrahydroisoquinoline derivatives against human oral squamous cell carcinoma cell lines."Anticancer Research 29.8(2009):3079-3086.

Chemical Properties

clear yellow to brown liquid

Uses

1,2,3,4-Tetrahydroisoquinoline is used as a reagent in the preparation of 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides as antiproliferative tubulin inhibitors.

Synthesis Reference(s)

The Journal of Organic Chemistry, 40, p. 1191, 1975 DOI: 10.1021/jo00897a001Tetrahedron Letters, 26, p. 4633, 1985 DOI: 10.1016/S0040-4039(00)98771-9

InChI:InChI=1/C9H11N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-4,10H,5-7H2/p+1

Upstream product

• 542-88-1 bis(2-chloromethyl)ether 
• 60-29-7 diethyl ether 
• 156-28-5 2-phenylethylamine hydrochloride 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 1196-38-9 3,4-dihydroisoquinolin-1(2H)-one 
• 109-87-5 Dimethoxymethane 
• 64-04-0 phenethylamine 
• 119-65-3 isoquinoline 
• 7742-73-6 1,3-dichloroisoquinoline 
• 54105-63-4 1,2,3,4-tetrahydroisoquinolin-2-ol 
• 53054-77-6 2-(2-propenyl)isoquinolinium bromide 
• 111875-01-5 3-(3,4-Dihydro-1H-isoquinoline-2-sulfonyl)-propionic acid ethyl ester 
• 1699-52-1 2-formyl-1,2,3,4-tetrahydroisoquinoline 
• 2079-11-0 N-allyl 1,2,3,4-tetrahydroisoquinoline 

Downstream Products

• 88014-15-7 2-(3,4-dihydro-1H-isoquinolin-2-yl)-ethanol 
• 2744-08-3 (4aS^*,8aS^*)-1,2,3,4,4a,5,6,7,8,8a-perhydroisoquinoline 
• 83095-06-1 N-(1,2,3,4-tetrahydroisoquinolin-2-ylmethyl)succinimide 
• 134750-52-0 N-<2-(hydroxymethyl)benzoyl>-1,2,3,4-tetrahydroisoquinoline 
• 1612-65-3 2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 14028-67-2 N-acetyl-1,2,3,4-tetrahydroisoquinoline 
• 57928-04-8 2-Ethyl-1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

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The β-hydroxyacid dehydrogenase from Thermocrinus albus (Ta-βHAD), which catalyzes the NADP+-dependent oxidation of β-hydroxyacids, was engineered to accept imines as substrates. The catalytic activity of the proton-donor variant K189D was further increased by the introduction of two nonpolar flanking residues (N192 L, N193 L). Engineering the putative alternative proton donor (D258S) and the gate-keeping residue (F250 A) led to a switched substrate specificity as compared to the single and triple variants. The two most active Ta-βHAD variants were applied to biocatalytic asymmetric reductions of imines at elevated temperatures and enabled enhanced product formation at a reaction temperature of 50 °C.

carba Nicotinamide Adenine Dinucleotide Phosphate: Robust Cofactor for Redox Biocatalysis

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Chemoselective and Tandem Reduction of Arenes Using a Metal–Organic Framework-Supported Single-Site Cobalt Catalyst

The development of heterogeneous, chemoselective, and tandem catalytic systems using abundant metals is vital for the sustainable synthesis of fine and commodity chemicals. We report a robust and recyclable single-site cobalt-hydride catalyst based on a porous aluminum metal–organic framework (DUT-5 MOF) for chemoselective hydrogenation of arenes. The DUT-5 node-supported cobalt(II) hydride (DUT-5-CoH) is a versatile solid catalyst for chemoselective hydrogenation of a range of nonpolar and polar arenes, including heteroarenes such as pyridines, quinolines, isoquinolines, indoles, and furans to afford cycloalkanes and saturated heterocycles in excellent yields. DUT-5-CoH exhibited excellent functional group tolerance and could be reusable at least five times without decreased activity. The same MOF-Co catalyst was also efficient for tandem hydrogenation–hydrodeoxygenation of aryl carbonyl compounds, including biomass-derived platform molecules such as furfural and hydroxymethylfurfural to cycloalkanes. In the case of hydrogenation of cumene, our spectroscopic, kinetic, and density functional theory (DFT) studies suggest the insertion of a trisubstituted alkene intermediate into the Co–H bond occurring in the turnover limiting step. Our work highlights the potential of MOF-supported single-site base–metal catalysts for sustainable and environment-friendly industrial production of chemicals and biofuels.