8-Chloroquinoline
- Iupac Name：8-chloroquinoline
- CAS No.: 611-33-6
- Molecular Weight：163.604
- Modify Date.: 2022-11-29 07:41
- Introduction:
CLEAR YELLOW TO BROWN LIQUID
8-chloroquinoline is a member of quinolines and an organochlorine compound.
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1. Names and Identifiers
- 1.1 Name
- 8-Chloroquinoline
- 1.2 Synonyms
8-Chlor-chinolin 8-chloro-quinoline EINECS 210-265-6 MFCD00047618 NSC 56815 Quinoline, 8-chloro- Quinoline,8-chloro
- 1.3 CAS No.
- 611-33-6
- 1.4 CID
- 69139
- 1.5 EINECS(EC#)
- 210-265-6
- 1.6 Molecular Formula
- C9H6ClN (isomer)
- 1.7 Inchi
- InChI=1S/C9H6ClN/c10-8-5-1-3-7-4-2-6-11-9(7)8/h1-6H
- 1.8 InChkey
- RUSMDMDNFUYZTM-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- C1=CC2=C(C(=C1)Cl)N=CC=C2
- 1.10 Isomers Smiles
- C1=CC2=C(C(=C1)Cl)N=CC=C2
2. Properties
- 2.1 Density
- 1.27
- 2.1 Melting point
- -20℃
- 2.1 Boiling point
- 288.5℃
- 2.1 Refractive index
- 1.6408 (14.3 C)
- 2.1 Flash Point
- 145.2 °C
- 2.1 Precise Quality
- 163.01900
- 2.1 PSA
- 12.89000
- 2.1 logP
- 2.88820
- 2.1 Appearance
- Clear yellow to brown Liquid
- 2.2 Chemical Properties
- CLEAR YELLOW TO BROWN LIQUID
- 2.3 Color/Form
- Clear yellow to brown
- 2.4 pKa
- 2.33±0.17(Predicted)
- 2.5 Water Solubility
- SOLUBLE
- 2.6 Stability
- Stable under normal temperatures and pressures.
- 2.7 StorageTemp
- Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
3. Use and Manufacturing
- 3.1 Methods of Manufacturing
- General procedure: PdClGeneral procedure: A mixture of aromatic amine (1.0 mmol), glycerol (3.0 mmol), and Br?nsted acidic ionic liquid BAIL (1.5 mmol) in a closed glass vial was heated using a GE model JE635WW microwave oven, at full power (920W) in five 20 s pulses giving 5 s cooling time between the pulses. Then cooled reaction mixture was diluted with water (30 mL), basified with 0.5 M aqueous sodium hydroxide and steam distilled. The distillate was extracted with methylene chloride (3X 6 mL). Combined organic layer was dried and chromatographed on silica, eluting with methylene chloride gave corresponding quinolines.General procedure: N-Heterocyclic amine (0.50 mmol), CoTPP (10 mg) and DMF (2 mL) were mixed in a carousel reaction tube. The reaction mixture was stirred at 120 C under oxygen atmosphere, the reaction was sampled periodically and monitored by TLC (petroleum ether/ethyl acetate (10:1 v/v)). After the reaction, the reaction mixture was then cooled to room temperature and purified using flash chromatography to give the corresponding product. All the dehydrogenation products are known, and their NMR spectra were consistent with the literature. NMR spectra were recorded at 25 C on an Bruker AVANCE III 400-NMR spectrometer at 400 MHz for General procedure: An ampule was charged with 0.02 mmol of FeClGeneral procedure: General procedure for synthesis of quinolines from anilines and ADA was carried out in Panasonic NN-K5541JF microwave oven reactor equipping a magnetic stirring device. The typical procedures were as follows: ADA (1mmol), excessive anilines (4mmol) and solid catalyst were charged into a round-bottom ask; and then, the mixtures was placed into microwave reactor. The reaction was conducted by continuous microwave irradiation for 1–40 min under refluxing and stirring condition. Finally, the resulting products were determined by GC–MS of Varian Saturn 2200/ CP-3800 gas chromatography–mass spectrometry equipped with two CP8944 capillary columns (VF-5, 30m×0.25mm×0.25 μm).General procedure: A mixture of aromatic amine (1.0 mmol), glycerol (3.0 mmol), and Broensted acidic ionic liquid BAIL (1.5 mmol) in a closed glass vial was heated using a GE model JE635WW microwave oven, at full power (920W) in five 20 s pulses giving 5 s cooling time between the pulses. Then cooled reaction mixture was diluted with water (30 mL), basified with 0.5 M aqueous sodium hydroxide and steam distilled. The distillate was extracted with methylene chloride (3X 6 mL). Combined organic layer was dried and chromatographed on silica, eluting with methylene chloride gave corresponding quinolines.
- 3.2 Purification Methods
- Purify it by crystallisation of its ZnCl2 complex (m 228o) from aqueous EtOH. [Beilstein 20 III/IV 3381, 20/7 V 315.] 8-Chloroquinoline Preparation Products And Raw materials Raw materials
4. Safety and Handling
- 4.1 Hazard Codes
- Xi
- 4.1 Risk Statements
- R36/37/38
- 4.1 Safety Statements
- S26;S37/39
- 4.1 Hazard Class
- IRRITANT
- 4.1 Hazard Declaration
- H315
- 4.1 Caution Statement
- P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Skin irritation, Category 2
Eye irritation, Category 2
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Warning |
| Hazard statement(s) | H315 Causes skin irritation H319 Causes serious eye irritation |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. |
| Response | P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. |
| Storage | none |
| Disposal | none |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
611-33-6Total: 6 Synthesis Route
9. Other Information
- 9.0 Mesh Entry Terms
- 8-chloroquinoline
- 9.1 Manufacturing Info
- Quinoline, 8-chloro-: INACTIVE
10. Computational chemical data
- Molecular Weight: 163.604g/mol
- Molecular Formula: C9H6ClN
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 163.0188769
- Monoisotopic Mass: 163.0188769
- Complexity: 138
- Rotatable Bond Count: 0
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 1
- Topological Polar Surface Area: 12.9
- 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: AAADcYByAAAEAAAAAAAAAAAAAAAAAAAAAAA8QAAAAAAAAACx8AAAHAIAAAAADArBHiQ8wPIIEACgAzRnRACCgCAxByAI2CA4ZpgIIOLBk5HEIAhggADIyAcQgIAOAAAAIAACABAAAABAAAQAIAAAAAAAAA==
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