578-66-5

Basic information

• Product Name: 8-Aminoquinoline
• Synonyms: 8-amino-quinolin;nc066;Quinoline, 8-amino-;wr6920;TIMTEC-BB SBB004126;QUINOLIN-8-AMINE;ASISCHEM Z74664;AKOS AUF01700
• CAS NO: 578-66-5
• Molecular Formula: C₉H₈N₂
• Molecular Weight: 144.17
• EINECS: 209-427-9
• Product Categories: Quinolines, Quinazolines and derivatives;Quinoline&Isoquinoline;Quinolines;Aminoquinolines;quinoline
• Mol File: 578-66-5.mol
• Article Data: 129

Chemical Properties

• Melting Point: 62-65 °C
• Boiling Point: 174 °C (26 mmHg)
• Flash Point: 174°C/26mm
• Appearance: Green to beige-brown/Crystalline Powder
• Density: 1.1148 (estimate)
• Vapor Pressure: 0.00215mmHg at 25°C
• Refractive Index: 1.7080 (estimate)
• Storage Temp.: Store below +30°C.
• PKA: pK1: 3.99(+1) (20°C,μ=0.01)
• Water Solubility: slightly soluble
• Sensitive: Air Sensitive
• BRN: 114474
• CAS DataBase Reference: 8-Aminoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Aminoquinoline(578-66-5)
• EPA Substance Registry System: 8-Aminoquinoline(578-66-5)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 68-36/37/38-20/21/22-36/38
• Safety Statements: 36/37/39-26-22-36
• RIDADR: UN2811
• WGK Germany: 3
• RTECS: VA9627000
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 578-66-5(Hazardous Substances Data)

Usage

Description

8-Aminoquinoline is a green to beige-brown crystalline powder that exhibits moderate to weak fluorescence in low dielectric media, but not in strongly hydrogen-bonding or acidic aqueous media. It has been studied for its reactions with various metal salts, including chromium (III), manganese (II), iron (II) and (III), cobalt (II), nickel (II), copper (II), zinc (II), cadmium (II), and platinum (II).

Uses

Used in Pesticide and Pharmaceutical Industries:
8-Aminoquinoline is used as an intermediate in the synthesis of various pesticides and pharmaceuticals, contributing to the development of these products for agricultural and healthcare applications.
Used in Chemical Research:
8-Aminoquinoline is utilized in the preparation of base-stabilized terminal borylene complex of osmium, which is significant for advancing chemical research and understanding the properties of such complexes.
Used in Analytical Chemistry:
In the field of analytical chemistry, 8-Aminoquinoline is employed for the spectrophotometric determination of bivalent palladium, aiding in the accurate measurement and analysis of this metal ion in various samples.

Preparation

Synthesis of 8-aminoquinoline: Under an ice bath, sulfuric acid (2.0 mL) was added onto quinoline (5 mmol, 1.0 equiv) then 65% nitric acid (3.0 equiv) were added dropwise and stirred for 4h at rt. The mixture was poured into the ice water and neutralized with NaOH; and then extracted with dichloromethane. After dried over Na2SO4 and evaporated in vacuo, used next step without purification.Mixture of nitroquinolines and 5% Pd/C was solved in ethanol and suspension was saturated with hydrogen gas under atmospheric pressure at 40°C until the starting material was consumed. 2 h later, the mixture was filtered and evaporated. The crude product was purified by silica gel column chromatography, eluting with EtOAc in hexanes to yield the desired 8-aminoquinoline is isolated as a brown solid in a yield of 32%.Obtained as a brown solid (231 mg, 32%); 1H NMR (500 MHz, CDCl3) δ 8.71 – 8.60 (m, 1H), 7.93 (d, J = 8.2 Hz, 1H), 7.29 – 7.16 (m, 2H), 7.02 (d, J = 8.1 Hz, 1H), 6.80 (d, J = 7.4 Hz, 1H), 4.89 (s, 2H).

Safety Profile

Human mutation data reported.When heated to decomposition it emits toxic fumes ofNOx.

Purification Methods

8-Aminoquinoline crystallises from EtOH, ligroin, octane or H2O, and complexes with metals. [Beilstein 22 III/IV 4708, 22/10 V 316.]

InChI:InChI=1/C9H8N2/c10-8-5-1-3-7-4-2-6-11-9(7)8/h1-6H,10H2

Upstream product

• 148-24-3 8-quinolinol 
• 607-35-2 8-nitroquinoline 
• 23833-99-0 4-chloro-8-nitroquinoline 
• 208191-72-4 8-nitro-quinolin-7-ol 
• 68527-66-2 6-chloro-8-nitroquinoline 
• 110-89-4 piperidine 
• 50400-06-1 8-azidoquinoline 
• 108-91-8 cyclohexylamine 
• 75-31-0 isopropylamine 
• 7647-01-0 hydrogenchloride 
• 7664-41-7 ammonia 
• 91-22-5 quinoline 
• 7462-74-0 2-bromo-2-methylpropanamide 
• 872-50-4 1-methyl-pyrrolidin-2-one 

Downstream Products

• 62366-01-2 4-phenyl-1,10-phenanthroline 
• 40535-46-4 Ν-(quinolinyl)-o-aminobenzoic acid 
• 857588-86-4 2-[8]quinolylamino-4-chloro-benzoic acid 
• 33757-42-5 N-(quinolin-8-yl)acetamide 
• 66262-71-3 2-Keto-N-(8'-chinolyl)-cyclopentan-carboxyamid 
• 33757-48-1 N-quinolin-8-yl-benzamide 
• 58107-20-3 1-phenyl-3-(quinolin-8-yl)urea 
• 33757-52-7 4-nitro-N-(quinolin-8-yl)benzamide 
• 32668-78-3 8-(2,5-dimethyl-1H-pyrrol-1-yl)quinoline 
• 7151-38-4 N-Methyl-N'--harnstoff 
• 32889-11-5 2-chloro-N-(quinolin-8-yl)acetamide 
• 16082-59-0 N-quinolin-8-yl-benzenesulfonamide 
• 10304-39-9 4-methyl-N-quinolin-8-yl-benzenesulfonamide 
• 29526-42-9 N,N-dimethylquinoline-8-amine 

Relevant articles and documents

Hydrazone Switch-Based Negative Feedback Loop

A negative feedback loop that relies on the coordination-coupled deprotonation (CCD) of a hydrazone switch has been developed. Above a particular threshold of zinc(II), CCD releases enough protons to the environment to trigger a cascade of reactions that yield an imine. This imine sequesters the excess of zinc(II) from the hydrazone switch, hence lowering the effective amount of protons, and switching the cascade reactions OFF , thus establishing the negative feedback loop.

Unlocking Amides through Selective C–N Bond Cleavage: Allyl Bromide-Mediated Divergent Synthesis of Nitrogen-Containing Functional Groups

We report a new set of reactions based on the unlocking of amides through simple treatment with allyl bromide, creating a common platform for accessing a diverse range of nitrogen-containing functional groups such as primary amides, sulfonamides, primary amines, N-acyl compounds (esters, thioesters, amides), and N-sulfonyl esters. The method has potential industrial applicability, as demonstrated through gram-scale syntheses in batch and in a continuous flow system.

Nickel-Catalyzed Regio- And Stereospecific C-H Coupling of Benzamides with Aziridines

A nickel-catalyzed C-H coupling of 8-aminoquinoline-derived benzamides with aryl- and alkyl-substituted aziridines has been disclosed. The current strategy provides direct access to benzolactams by the C-H alkylation-intramolecular amidation cascade event with the concomitant removal of the aminoquinoline auxiliary. The regioselectivity of ring opening of aziridines can be controlled by the substituents. The reaction with chiral aziridines proceeds with inversion of configuration, thus suggesting an SN2-type nucleophilic ring-opening pathway.

Method for synthesizing heteroatom- substituted aromatic compound from styrene compound

The invention discloses a method for synthesizing a heteroatom-substituted aromatic compound from a styrene compound, which comprises the following steps of: mixing a styrene compound with a general formula (I) and a heteroatom-containing compound with a general formula (II), and reacting in the presence of an acid additive and an organic solvent to obtain a heteroatom-substituted compound with ageneral formula (III). According to the synthesis method disclosed by the invention, a large amount of styrene compounds are used as raw materials and react to generate aromatic amine or phenol compounds under the action of no metal catalysis; and compared with the traditional aromatic amine and phenol synthesis method, the method has the advantages of high yield, simple conditions, low waste discharge amount, no metal participation, simple reaction equipment, easiness in industrial production and the like.