153856-89-4

Basic information

• Product Name: 7-Amino-1,2,3,4-tetrahydroquinoline
• Synonyms: 7-AMINO-1,2,3,4-TETRAHYDROQUINOLINE;7-Quinolinamine,1,2,3,4-tetrahydro-(9CI);7-AMINO-1,2,3,4-TETRAHYDROQUINOLIN;1,2,3,4-tetrahydroquinolin-7-aMine;1,2,3,4-Tetrahydro-quinolin-7-ylaMine
• CAS NO: 153856-89-4
• Molecular Formula: C₉H₁₂N₂
• Molecular Weight: 148.2
• EINECS: -0
• Product Categories: AMINEPRIMARY
• Mol File: 153856-89-4.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 321.89 °C at 760 mmHg
• Flash Point: 173.647 °C
• Appearance: /
• Density: 1.101 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 5.76±0.20(Predicted)
• CAS DataBase Reference: 7-Amino-1,2,3,4-tetrahydroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Amino-1,2,3,4-tetrahydroquinoline(153856-89-4)
• EPA Substance Registry System: 7-Amino-1,2,3,4-tetrahydroquinoline(153856-89-4)

Safety Data

• Hazardous Substances Data: 153856-89-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Canadian Journal of Chemistry, 30, p. 720, 1952 DOI: 10.1139/v52-085

InChI:InChI=1/C9H12N2/c10-8-4-3-7-2-1-5-11-9(7)6-8/h3-4,6,11H,1-2,5,10H2

Upstream product

• 613-51-4 7-nitroquinoline 
• 30450-62-5 7-nitro-1,2,3,4-tetrahydro-quinoline 
• 4169-19-1 1-acetyl-1,2,3,4-tetrahydroquinoline 
• 22246-07-7 7-amino-3,4-dihydro-2(1H)-quinolinone 
• 1176657-15-0 tert-butyl (1,2,3,4-tetrahydroquinolin-7-yl)carbamate 
• 861529-01-3 benzoic acid-[2-(3-chloro-propyl)-5-nitro-anilide] 
• 861609-66-7 2-(3-chloro-propyl)-5-nitro-aniline 
• 40484-69-3 1-benzoyl-7-nitro-1,2,3,4-tetrahydro-quinoline 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 580-19-8 quinolin-7-ylamine 
• 767-92-0 decahydroquinoline 

Downstream Products

• 946266-78-0 N-(1-benzoyl-1,2,3,4-tetrahydro-[7]quinolyl)-benzamide 
• 580-19-8 quinolin-7-ylamine 
• 587-02-0 m-ethylaniline 
• 578-54-1 ortho-ethylaniline 
• 62-53-3 aniline 
• 58196-33-1 7-hydroxy-1,2,3,4-tetrahydroquinoline 

Relevant articles and documents

Photostable, amino reactive and water-soluble fluorescent labels based on sulfonated rhodamine with a rigidized xanthene fragment

Highly water soluble fluorescent dyes were synthesized and transformed into new amino reactive fluorescent labels for biological microscopy. To this end, rhodamine 8 (prepared from 7-hydroxy-1,2,3,4-tetrahydroquinoline (7) and phthalic anhydride in 85% aq. H3PO4) was sulfonated with 30% SO3 in H2SO4 and afforded the water soluble disulfonic acid 3 a (64%). Amidation of the carboxy group in 3 a with 2-(methylamino)ethanol in the presence of O-(7-azabenzotriazol-1-yl)-N,N,N, N′-tetramethyluronium·PF6- (HATU) led to alcohol 3b (66%), which was transformed into the amino reactive mixed carbonate 3d with di(N-succinimidyl)carbonate and Et3N, Reaction of the carboxy group in 3a with MeNH(CH2)2CO2Me and N,N,N′,N′-tetramethyl-O-(N-succinimidyl)-uronium-BF4 - (TSTU) yielded methyl ester 13. After saponification of the aliphatic carboxy group in 13, the compound was converted into NHS-ester 3e (using HATU and Et3N). Heating of 7 with trimellitic anhydride in H3PO4 gave a mixture of dicarboxylic acids 14 and 15 (1:1). Regioisomer 15 was isolated, sulfonated with 30% SO3 in H 2SO4, and disulfonic acid 3f was used for the synthesis of the mono NHS-ester 3g, in which the sterically unhindered carboxy group was selectively activated (with n-hydroxysuccinimide, HATU, and Et3N). The sulfonated rhodamines 3 b, c and f are soluble in water (up to 0.1 M), have excellent photostabilities and large fluorescence quantum yields. Subdiffraction resolution images of tubulin filaments of mammalian cells stained with these dyes illustrate their applicability as labels for stimulated emission depletion microscopy and other fluorescence techniques.

Cu-Catalyzed Chemoselective Reduction of N-Heteroaromatics with NH3·BH3 in Aqueous Solution

An efficient catalytic system was successfully developed on reduction of N-heteroaromatics with H3N?BH3 as hydrogen source in CuSO4 solution, featuring excellent chemoselectivity as well as very broad functional group tolerance. Various challenging substrates, such as OH-, NH2-, Cl-, Br-, etc., contained quinolines, quinoxalines, 1,5-naphthyridines and quinazolines were all reduced smoothly. Mechanistic studies suggested that [Cu-H] intermediate might be generated from NH3?BH3, which was believed to form with H3N?BH3 in CuSO4 solution.

A 4, 4 - dimethoxy - 2, 2 - bipyridyl silver catalytic hydrogenation of aromatic nitro compound synthesis of aromatic amines (by machine translation)

The invention discloses a 4, 4 - dimethoxy - 2, 2 - bipyridyl silver catalytic hydrogenation of aromatic nitro compound synthesis of aromatic amines, the method uses a cheap, easy synthesis of 4, 4 - dimethoxy - 2, 2 - bipyridyl silver as catalyst, in order to green, environmental protection, non-toxic as the hydrogen source, the aromatic nitro compound in the relatively mild reaction conditions, one-step reaction can synthesize aromatic amine. The invention has simple operation, catalyst is cheap and easy and small consumption, mild reaction conditions, to substrate demonstrates better functional group tolerant, high product yield, industrial manufacturing cost, it has very good application prospect. (by machine translation)

TETRAHYDRONAPHTHYRIDINE, BENZOXAZINE, AZA-BENZOXAZINE, AND RELATED BICYCLIC COMPOUNDS FOR INHIBITION OF RORgamma ACTIVITY AND THE TREATMENT OF DISEASE

The invention provides certain bicylic heterocyclic compounds of the Formula (I) or pharmaceutically acceptable salts thereof, wherein X1, X2, R1, R2, R3, R4, and Cy are as defined herein. The invention also provides pharmaceutical compositions comprising such compounds of the Formula (I) or pharmaceutically acceptable salts thereof, and methods of using the compounds of the Formula (I) or pharmaceutically acceptable salts thereof or pharmaceutical compositions comprising the same for treating diseases or conditions mediated by RORgammaT.