1,2,3,4-TETRAHYDROISOQUINOLINE

1,2,3,4-TETRAHYDROISOQUINOLINE Basic information
Synthesis Description Reference
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:91-21-4
MF:C9H11N
MW:133.19
EINECS:202-050-0
Product Categories:Bioactive Small Molecules;Building Blocks;Cell Biology;Chemical Synthesis;Heterocyclic Building Blocks;T;Quinoline&Isoquinoline;Building Blocks;Heterocyclic Building Blocks;Isoquinolines;bc0001
Mol File:91-21-4.mol
1,2,3,4-TETRAHYDROISOQUINOLINE Structure
1,2,3,4-TETRAHYDROISOQUINOLINE Chemical Properties
Melting point −30 °C(lit.)
Boiling point 232-233 °C(lit.)
density 1.064 g/mL at 25 °C(lit.)
vapor pressure 3.33-97.9Pa at 20-58.5℃
refractive index n20/D 1.568(lit.)
Fp 210 °F
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility 20g/l
form Liquid
pka9.66±0.20(Predicted)
color Clear yellow to brown
Water Solubility Soluble in water at 20°C 20g/L.
BRN 116156
InChIKeyUWYZHKAOTLEWKK-UHFFFAOYSA-N
CAS DataBase Reference91-21-4(CAS DataBase Reference)
EPA Substance Registry SystemIsoquinoline, 1,2,3,4-tetrahydro- (91-21-4)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
RTECS NX4900000
Hazard Note Irritant
TSCA Yes
HS Code 29334900
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
1,2,3,4-TETRAHYDROISOQUINOLINE Usage And Synthesis
SynthesisTo 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. Synthesis of tetrahydroisoquinolinone 
Reference: Schultz, A. G.; Guzi, T. J.; Larsson, E.; Rahm, R.; Thakker, K. Bidlack, J. M. J. Org. Chem. 1998, 63, 7795–7804.
Description1, 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
  1. https://www.alfa.com/en/catalog/L08143/
  2. https://www.ncbi.nlm.nih.gov/pubmed/21235510
  3. https://en.wikipedia.org/wiki/Tetrahydroisoquinoline
  4. 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.
  5. 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.
  6. 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 Propertiesclear yellow to brown liquid
Uses1,2,3,4-Tetrahydroisoquinoline is used as a reagent in the preparation of 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides as antiproliferative tubulin inhibitors.
DefinitionChEBI: 1,2,3,4-tetrahydroisoquinoline is a member of isoquinolines.
Synthesis Reference(s)The Journal of Organic Chemistry, 40, p. 1191, 1975 DOI: 10.1021/jo00897a001
Tetrahedron Letters, 26, p. 4633, 1985 DOI: 10.1016/S0040-4039(00)98771-9
Clazolam 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride 1,2-DIMETHYL-6,7-DIMETHOXY-1,2,3,4-TETRAHYDROISOQUINOLINE HYDROCHLORIDE LABOTEST-BB LT00452039 Isoquinoline, 1,2,3,4-tetrahydro-2-methyl- 2-(3,4-DIHYDROISOQUINOLIN-2(1H)-YL)-5-(TRIFLUOROMETHYL)ANILINE [4-CHLORO-2-(1,2,3,4-TETRAHYDRO-ISOQUINOLIN-1-YL)-PHENYL]-METHYL-AMINE DL-6'-BROMOLAUDANOSIN (-)-1-[5-CHLORO-2-(METHYLAMINO)PHENYL]-1,2,3,4-TETRAHYDROISOQUINOLINE,(-)-TARTRATE 1,2,3,4-TETRAHYDROISOQUINOLINE 1,2,3,4-L-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID 6,7-DIHYDROXY-1-METHYL-1,2,3,4-TETRAHYDROISOQUINOLINE HYDROBROMIDE D-TUBOCURARINE CHLORIDE 1-BENZYL-1,2,3,4-TETRAHYDROISOQUINOLINE DL-LAUDANOSOLINE HYDROBROMIDE TRIHYDRATE 1,2,3,4-TETRAHYDROISOQUINOLINE HYDROCHLORIDE (+/-)-TETRAHYDROPAPAVEROLINE HYDROBROMIDE DL-LAUDANOSINE

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