6329-61-9

Basic information

• Product Name: Decahydroisoquinoline
• Synonyms: PERHYDROISOQUINOLINE;DECAHYDROISOQUINOLINE;PERHYDROISOQUINOLINE, 96%, MIXTURE OF CIS AND TRANS;decahydroisoquiline(cis-and trans-mixture);DECAHYDROISOQUINOLINE (CIS- AND TRANS- MIXTURE);3-Azabicyclo[4.4.0]decane;perhydroisoquinoline(PHIQ);Decahydroisoquinoline (cis- and trans- mixture, predominant trans-isomer)
• CAS NO: 6329-61-9
• Molecular Formula: C₉H₁₇N
• Molecular Weight: 139.24
• EINECS: 228-702-4
• Product Categories: API intermediates;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Isoquinolines
• Mol File: 6329-61-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 180 °C
• Boiling Point: 211-214 °C(lit.)
• Flash Point: 175 °F
• Appearance: Colorless and transparent liquid
• Density: 0.936 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.4904(lit.)
• Solubility: soluble in Methanol
• PKA: 11.84±0.20(Predicted)
• CAS DataBase Reference: Decahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: Decahydroisoquinoline(6329-61-9)
• EPA Substance Registry System: Decahydroisoquinoline(6329-61-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 6329-61-9(Hazardous Substances Data)

Usage

Description

Decahydroisoquinoline, also known as perhydroisoquinoline, is an organic compound belonging to the isoquinoline family. It is a fully saturated, cyclic structure with a hydrogenated form of isoquinoline, which gives it unique chemical and physical properties. Its structure allows for various interactions with other molecules, making it a versatile compound in different applications.

Uses

Used in Pharmaceutical Industry:
Decahydroisoquinoline is used as an intermediate in the synthesis of various pharmaceutical compounds. One notable example is its use in the synthesis of nelfinavir mesylate, an antiretroviral medication used to treat HIV/AIDS. Its unique structure and properties make it a valuable component in the development of new drugs and therapies.
Used in Spectroscopic Research:
Decahydroisoquinoline has been utilized in the study of charge-transfer complexes with other molecules, such as 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, p-chloranil, and 7,7′,8,8′-tetracyanoquinodimethane. These investigations contribute to the understanding of the compound's interactions and potential applications in various fields, including materials science and chemical analysis.

InChI:InChI=1/C9H17N/c1-2-4-9-7-10-6-5-8(9)3-1/h8-10H,1-7H2

Upstream product

• 119-65-3 isoquinoline 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 90653-76-2 N-ethoxycarbonyl-cis-decahydroisoquinoline 
• 91240-10-7 (4aS^*,8aS^*)-1,2,3,4,4a,5,6,7,8,8a-perhydroisoquinoline-1,3-dione 
• 122490-16-8 (4aS^*,8aS^*)-1,2,3,4,4a,7,8,8a-octahydroisoquinoline-1,3-dione 
• 73670-84-5 (E)-3,5-hexadienoyl chloride 
• 108306-30-5 (4aS^*,8aS^*)-1-ethoxy-3,4,4a,7,8,8a-hexahydroisoquinol-3-one 
• 2744-08-3 decahydroisoquinoline 
• 87463-47-6 cis-1,2,3,4,4a,5,6,7,8,8a-Decahydro-2-methylisoquinoline 
• 108306-26-9 ethyl N-(3,5-hexadienoyl)-acrylimidate 
• 67123-97-1 (R,S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 36556-06-6 5,6,7,8-tetrahydroisoquinoline 
• 3336-60-5 1-chloro-4-methoxyisoquinoline 
• 10034-85-2 hydrogen iodide 

Downstream Products

• 109445-99-0 3,4-dihydro-1H-spiro[isoquinoline-2,1'-piperidinium]; bromide 
• 14028-67-2 N-acetyl-1,2,3,4-tetrahydroisoquinoline 
• 82342-56-1 N-benzoyl-1,2,3,4-tetrahydroisoquinoline 
• 83491-16-1 N-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxamide 
• 89652-23-3 3,4-dihydro-1H-isoquinoline-2-carbothioic acid phenylamide 
• 88014-09-9 (3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid ethyl ester 
• 5653-11-2 α-(1,2,3,4-Tetrahydro-2-isochinolyl)-acetophenon 
• 1637-45-2 2,2-dimethyl-1,2,3,4-tetrahydroisoquinolinium iodide 
• 17721-96-9 2-nitroso-1,2,3,4-tetrahydroisoquinoline 
• 36556-06-6 5,6,7,8-tetrahydroisoquinoline 
• 119-65-3 isoquinoline 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

PtRuNi/C novel nanostructures of platinum-ruthenium island-on-Ni/Ni(OH)2 nanoparticles for the selective hydrogenation of quinoline

Ni/C was successfully synthesized via hydrazine hydrate reduction at room temperature (RT). Pt/C, Ru/C and PtRu/C were prepared via an impregnation method. PtNi/C, RuNi/C and PtRuNi/C were synthesized via a chemical replacement method. The characterization results revealed that PtRuNi nanoparticles (NPs) were highly and uniformly dispersed on carbon black in PtRuNi/C. PtRuNi/C showed a novel nanostructure in which PtRu islands (PtRu nanoclusters or PtRu binary atoms) covered Ni/Ni(OH)2 NPs. PtRuNi/C trimetallic nanomaterial exhibited an optimum catalytic performance (turnover frequency (TOF) = 211.4 h?1 and selectivity for the production of 1,2,3,4-tetrahydroquinoline (py-THQ) > 99%) in the selective hydrogenation of quinoline at 60 °C under 5.0 MPa H2. The catalytic properties of PtRuNi/C were significantly improved as compared to bimetallic (PtNi/C, RuNi/C and PtRu/C) and monometallic (Ni/C, Pt/C and Ru/C) nanomaterials due to its unique nanostructure, with an observed nano-synergy effect among Pt-, Ru- and Ni-related species.

PEPTIDE COMPOUNDS DERIVED FROM BORONIC ACID

A compound of formula (I): STR1 in which: R 1 represents hydrogen or acyl, alkyl, benzyl, alkoxycarbonyl, benzyloxycarbonyl, phenoxycarbonyl, 5-[(dimethyl)amino]naphthylsulfonyl, alkoxycarbonylmethyl or carboxymethyl,R 2 represents hydrogen or phenyl, substituted or unsubstituted benzyl, 3-thienylmethyl, 2-pyridylmethyl, diphenylmethyl, fluorenyl, naphthylmethyl, benzocyclobutyl, (dicyclopropylmethyl)methyl, indanyl or (C 3-C 7 cycloalkyl)methyl,R' 2 represents hydrogen or benzylor alternativelyR 2 and R'. sub.2 together represent C 6 H 5--CH=,R. sub.3 represents substituted alkyl or guanidinophenyl, amidinophenyl, aminophenyl, guanidinobenzyl, amidinobenzyl, aminobenzyl or cycloalkyl, R 4 and R 5 each represent hydrogen or alkyl, or STR2 forms a boronic ester of pinanediol, A represents any one of the groups as defined in the description.Medicinal products.

Hydrogenation Pathway of Quinolines over Raney Nickel and Ru/C

Quinoline, 2-methylquinoline, and 8-methylquinoline were hydrogenated over Raney Nickel (R-Ni) under 10 atm hydrogen pressure at about 200 deg C and over ruthenium on carbon (Ru/C) under 100 atm hydrogen pressure at 150 deg C.All the substrates were commonly hydrogenated into the initial products, 1,2,3,4-tetrahydroquinolines.The initial products were competitively converted over R-Ni to the final products, decahydroquinolines, directly or via 5,6,7,8-tetrahydroquinolines which were mainly formed from the initial products by isomerization.Ru/C promoted exclusively the direct hydrogenation of 1,2,3,4-tetrahydro derivatives to the final products.The hydrogenation and isomerization of 1,2,3,4-tetrahydroquinoline was completely inhibited in the competitive hydrogenation of quinoline and isoquinoline over R-Ni.Such features of these substrates are explained by the strong basicity of 1,2,3,4-tetrahydroisoquinoline.Roles of 1,2,3,4-tetrahydroisoquinoline are much moderate on Ru/C, where the ?-coordination may be important.The effects of methyl substituent and different reactivities of quinoline and isoquinoline are discussed in terms of the steric hindrance on adsorption, heats of hydrogenation, basicities, and electronic properties of the related compound, which are calculated according to the MNDO-PM3 method.