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7-Hydroxy-1,2,3,4-tetrahydroquinoline structure
7-Hydroxy-1,2,3,4-tetrahydroquinoline structure

7-Hydroxy-1,2,3,4-tetrahydroquinoline

Iupac Name:1,2,3,4-tetrahydroquinolin-7-ol
CAS No.: 58196-33-1
Molecular Weight:149.193
Modify Date.: 2022-11-22 16:00
1. Names and Identifiers
1.1 Name
7-Hydroxy-1,2,3,4-tetrahydroquinoline
1.2 Synonyms

1,2,3,4-Tetrahydro-7-hydroxyquinoline 1,2,3,4-Tetrahydro-7-quinolinol 1,2,3,4-Tetrahydro-quinolin-7-ol 7-Hydroxy-1,2,3,4-Tetrahydro Quinolinoe 7-Hydroxy-1,2,3,4-tetrahydroquinoL 7-hydroxy-1,2,3,4-Tetrahydro-quinolin 7-Hydroxy-1,2,3,4-tetrahydroquinoline 7-Quinolinol, 1,2,3,4-tetrahydro-

1.3 CAS No.
58196-33-1
1.4 CID
93980
1.5 Molecular Formula
C9H11NO (isomer)
1.6 Inchi
InChI=1S/C9H11NO/c11-8-4-3-7-2-1-5-10-9(7)6-8/h3-4,6,10-11H,1-2,5H2
1.7 InChkey
HJJRGZMJZDSMDB-UHFFFAOYSA-N
1.8 Canonical Smiles
C1CC2=C(C=C(C=C2)O)NC1
1.9 Isomers Smiles
C1CC2=C(C=C(C=C2)O)NC1
2. Properties
3.1 Density
1.141 g/cm3
3.1 Melting point
70-80 °C
3.1 Boiling point
319.7 °C at 760 mmHg
3.1 Refractive index
1.582
3.1 Flash Point
174.7 °C
3.1 Precise Quality
149.08400
3.1 PSA
32.26000
3.1 logP
1.88830
3.1 Appearance
light yellow solid
3.2 Color/Form
Light-red to Brown Solid
3.3 pKa
10.70±0.20(Predicted)
3. Use and Manufacturing
4.1 Methods of Manufacturing
7-Hydroxy-3, 4-dihydroquinolin-2(1H)-one(2.00 g, 12.26 mmol) was dissolved in THF (20 mL) and cooled to 0oC. After the addition ofNaBH4 (1.07 g, 28.19 mmol), I2 (3.42 g, 13.48 mmol) dissolved in THF (20 mL) was added to thesolution dropwise via an addition funnel. The reaction was then fitted with a condenser andrefluxed overnight. The solution was then neutralized with 3 M hydrochloric acid and thenextracted with dichloromethane three times, dried over magnesium sulfate. Evaporation ofthe solvent resulted in a viscous yellow oil. The crude material was purified by flash columnchromatography to yield the product as a white crystalline solid (1.80 g) in a 98percent yield.A solution of 7-hydroxy-3, 4-dihydroquinolin-2(1H)-one (12, 5.0 g, 30.64 mmol) in anhydrous THF (30 mL) was added dropwise to a suspended solution of LiAlH4 (1.7 g, 44.80 mmol) in anhydrous THF (70 mL) at 0. After the mixture was stirred for 15 min, the cooled batch was removed, and then the mixture was heated to 65 and stirred for 16 h. The resulting reaction mixture was diluted with THF (50 mL) and quenched with saturated NH4Cl (5 mL) in the ice-water batch. The aqueous solution was adjusted to PH 4-5 with 4 N HCl solution and extracted with EtOAc (100 mL × 2). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with ethyl acetate/petroleum ether (1:20-1:10-1:5, v/v), to afford the intermediate 13 (3.03 g, 66percent yield) as a slight yellow solid. 1H NMR (400 MHz, CDCl3) δ 6.79 (d, J = 8.1 Hz, 1H), 6.12 (dd, J = 8.1, 2.3 Hz, 1H), 5.97 (d, J = 2.2 Hz, 1H), 4.55 (s, 2H), 3.32-3.13 (m, 2H), 2.67 (t, J = 6.4 Hz, 2H), 1.97-1.80 (m, 2H). 13C NMR (101 MHz, CDCl3) δ 154.68 (s), 145.50 (s), 130.45 (s), 114.45 (s), 104.79 (s), 101.18 (s), 42.04 (s), 26.32 (s), 22.46 (s).1, 2, 3, 4-tetrahydro-7-hydroxyquinoline 1, 2, 3, 4-tetrahydro-7-hydroxyquinoline 1, 2, 3, 4-tetrahydro-7-hydroxyquinoline. 1, 2, 3, 4-tetrahydro-7-hydroxyquinoline. 1, 2, 3, 4-tetrahydro-7-hydroxyquinoline
4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s) no data available
Signal word

no data available

Hazard statement(s)

no data available

Precautionary statement(s)
Prevention

no data available

Response

no data available

Storage

no data available

Disposal

no data available

2.3 Other hazards which do not result in classification

no data available

6. Other Information
6.0 Manufacturing Info
7-Quinolinol, 1,2,3,4-tetrahydro-: INACTIVE
7. Computational chemical data
  • Molecular Weight: 149.193g/mol
  • Molecular Formula: C9H11NO
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 149.084063974
  • Monoisotopic Mass: 149.084063974
  • Complexity: 138
  • Rotatable Bond Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 2
  • Topological Polar Surface Area: 32.3
  • Heavy Atom Count: 11
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADccByIAAAAAAAAAAAAAAAAAAAAAAAAAA8QAAAAAAAAACxAAAAHgAQCAAADAzBmAQwxoLAAgCAAiRCQACCAAAhIgAIiIAObIgIJiLCkZOEcAhm0BnI2AeQ0KMOIAAAAgACAABAAAAEAAQAAAAAAAAAAA==
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