quinoline

• ChemBase ID: 103510
• Molecular Formular: C9H7N
• Molecular Mass: 129.15858
• Monoisotopic Mass: 129.05784923
• SMILES: c1cc2cccnc2cc1
• Canonical SMILES: c1ccc2c(c1)nccc2
• InChI: InChI=1S/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H
• InChIKey: SMWDFEZZVXVKRB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: quinoline
• IUPAC Systematic name: 2-azabicyclo[4.4.0]deca-1(6),2,4,7,9-pentaene; 2-azabicyclo[4.4.0]deca-1,3,5,7,9-pentaene; benzo[b]azine; benzo[b]azabenzene
• IUPAC Traditional name: cinch
• Synonyms: 1-azanaphthalene; benzo[b]pyridine; benzazine; benzazabenzene; benzopyridine; 1-benzine; quinolin; chinoline; chinoleine; chinolin; leucol; leukol; leucoline; Quinoline; 2,3-benzopyridine; 1-Benzazine; 2,3-Benzopyridine; QUINOLINE; 1-偶氮萘; 苯并吡啶; 喹啉

Database IDs

• CAS Number: 91-22-5
• EC Number: 202-051-6
• MDL Number: MFCD00006736
• Beilstein Number: 107477
• Merck Index: 148068
• PubChem SID: 24849279; 162090609; 24899202; 24901720; 24854491
• PubChem CID: 7047
• CHEBI ID: 17362
• CHEMBL: 14474
• Chemspider ID: 6780
• FEMA ID: 3470
• KEGG ID: C06413
• MeSH Name: Quinolines
• Unique Ingredient Identifier: E66400VT9R
• Wikipedia Title: Quinoline
• Council of Europe Number: 11364
• Flavis Number: 14.063

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.0912383
• LogD (pH = 7.4): 2.1303756
• Log P: 2.1309004
• Molar Refractivity: 39.9793 cm^3
• Polarizability: 17.084923 Å^3
• Polar Surface Area: 12.89 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: More soluble in hot than cold water. Miscible with alcohol, ether; Slightly soluble in water
• Apperance: clear, brown liquid; Liquid; yellowish oily liquid
• Melting Point: −15 °C; -15°C; -17--13 °C(lit.); -19.5 - 14.2 °C
• Boiling Point: 113-114 °C/11 mmHg(lit.); 237 °C(lit.); 237 °C/760 mm Hg, 108-110 °C/11 mm Hg; 237.1 °C at 1013 hPa; 237°C
• Flash Point: 101 °C; 101°C(214°F); 107 °C (closed cup); 213.8 °F
• Auto Ignition Point: 400 °C; 480 °C at 1013 hPa; 896 °F
• Density: 1.090; 1.093 g/mL; 1.093 g/mL at 25 °C(lit.); 1.0938 g/cm^3 at 20 °C
• Refractive Index: 1.6260; n20/D 1.625; n20/D 1.625(lit.)
• Vapor Pressure: .012 hPa at 25 °C; 0.07 mmHg ( 20 °C)
• Vapor Density: 4.45 (Air = 1); 4.5 (vs air)
• pKa: 4.85
• Std enthalpy of formation: 174.9 kJ mol^-1

Safety Information

• Storage Condition: Room Temperature (15-30°C), Desiccate, Protect from light
• Storage Warning: Light Sensitive & Hygroscopic
• RTECS: VA9275000
• European Hazard Symbols: Corrosive (C); Nature polluting (N); Toxic (T); Harmful (Xn)
• UN Number: 2656; UN2656
• German water hazard class: 2
• Hazard Class: 6.1
• Packing Group: 3; III
• Australian Hazchem: 3Z
• Risk Statements: 45-21/22-36/38-51/53-68; 45-21/22-36/38-68-51/53; R:22-27-34; R21, R22
• Safety Statements: 53-45-61; S:26-27/28-36/37/39-46-64; S26, S27, S28, S29, S30, S31, S32, S33, S34, S35, S36
• EU Classification: T1
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS08; GHS09
• GHS Signal Word: Danger
• NFPA704:
  

  1

  2

  0
• LD50: 331 mg/kg
• GHS Hazard statements: H301-H312-H315-H319-H341-H350-H411; H302-H311-H315-H319-H341-H350-H411; H311-H302-H315-H319-H350-H341-H411-H401
• GHS Precautionary statements: P201-P273-P280-P301 + P310-P305 + P351 + P338-P308 + P313; P201-P273-P280-P305 + P351 + P338-P308 + P313; P280-P305+P351+P338-P361-P302+P352-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2656 6.1/PG 3

Pharmacology Properties

• Gene Information: human ... CYP2D6(1565)

Product Information

• Purity: ~98%; ≥90% (GC); ≥94.0%; ≥95.0%; ≥96% (GC); ≥97%; ≥97.0% (GC); ≥99%; 95+%; 96%; 97%; 98%
• Grade: JIS special grade; NI; purum; reagent grade; SAJ first grade; technical
• Empirical Formula (Hill Notation): C9H7N

DETAILS

MP Biomedicals - 02152010

Purity: ~98%
1 ml = approx. 1.09 g

Sigma Aldrich - W347000

Packaging
1 kg in glass bottle
1 sample in glass bottle
5, 10 kg in poly drum

Sigma Aldrich - Q1255

Packaging
500 g in glass bottle

Sigma Aldrich - 241571

Packaging
5, 100, 500 g in glass bottle

REFERENCES

• Dehydrohalogenation base; see, e.g.: Org. Synth. Coll., 4, 608 (1963).
• Widely used solvent for the copper-promoted decarboxylation of carboxylic acids; see, e.g.: Org. Synth. Coll., 4, 731, 857 (1963).
• Reacts with acyl halides in the presence of an alkali cyanide to give Reissert compounds. For reviews, see: Chem. Rev., 55, 511 (1955); Adv. Het. Chem., 9, 1 (1968); 24, 187 (1979). See also Isoquinoline, B21279. For the formation of Reissert compounds under phase-transfer conditions, with a variety of carbonyl, sulfonyl and phosphoryl halides, see: Synthesis, 497 (1977). For 'direct' cyanation by a modified Reissert procedure, using DBU, see: J. Org. Chem., 49, 4056 (1984).
• Enhances selectivity of reduction of alkynes to alkenes over Lindlar catalyst: Org. Synth. Coll., 5, 880 (1973). In combination with sulfur, is a catalyst poison for the Rosenmund reduction of acid chlorides to aldehydes: Org. Synth. Coll., 3, 629 (1955), Note 4.
• Li or Na in liquid ammonia give the 1,4-dihydro-derivative: Tetrahedron Lett., 2395 (1975), whereas pyridine-borane gives 1,2,3,4-tetrahydroquinoline: Synthesis, 447 (1978). Reaction with NaBH₄ and a carboxylic acid results in "reduction-alkylation" to a 1-alkyl-1,2,3,4-tetrahydroquinoline: Synthesis, 650 (1975); compare also Sodium cyanoborohydride, 87839. However, selective hydrogenation of the benzene ring over PtO₂ in conc. HCl was reported: J. Am. Chem. Soc., 96, 2256 (1974).
• A novel radical alkylation of quinoline and related heterocycles in the 2-position uses free radicals generated by reaction of alkyl iodides with hydrogen peroxide in DMSO: J. Org. Chem., 54, 5224 (1989). For silver(II)-promoted radical alkylation, see: Trimethylacetic acid, A10776.