Name | Quinoline |
Synonyms | B 500 b-500 B-500 leukol leucol ai3-01241 Quinoline 1-Benzine chinoline 1-benzine 1-Benzaine Chinoleine chinoleine Benzopyridine |
CAS | 91-22-5 |
EINECS | 202-051-6 |
InChI | InChI=1/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H |
InChIKey | SMWDFEZZVXVKRB-UHFFFAOYSA-N |
Molecular Formula | C9H7N |
Molar Mass | 129.16 |
Density | 1.093 g/mL at 25 °C (lit.) |
Melting Point | -17--13 °C (lit.) |
Boling Point | 113-114 °C/11 mmHg (lit.)237 °C (lit.) |
Flash Point | 214°F |
Water Solubility | slightly soluble |
Solubility | 6g/l |
Vapor Presure | 0.07 mm Hg ( 20 °C) |
Vapor Density | 4.5 (vs air) |
Appearance | Liquid |
Color | Purple to dark grey |
Odor | Strong, unpleasant. |
Merck | 14,8068 |
BRN | 107477 |
pKa | 4.9(at 20℃) |
PH | 7.3 (5g/l, H2O, 20℃) |
Storage Condition | Store below +30°C. |
Stability | Stable. Incompatible with strong acids, strong oxidizing agents. May discolour on exposure to light. Hygroscopic - protect from moisture. Reacts violently and unpredictably with some materials, especi |
Sensitive | Light Sensitive & Hygroscopic |
Explosive Limit | 1.2-7%(V) |
Refractive Index | n20/D 1.625(lit.) |
Physical and Chemical Properties | Melting point (℃):-14.5 boiling point (℃):237.7 relative density (Air = 1):1.09 relative density (water = 1):4.5 saturated vapor pressure (kpa):0.13 log of octanol/water partition coefficient: 2.6 solubility: soluble in water, alcohol, ether, most organic solvents such as carbon disulfide heat of combustion (kj/mol):4696.2 refractive index: 1.6268(20 ℃) |
Use | It can also be used as acid, solvent, preservative, etc. The pharmaceutical industry is used to make nicotinic acid and 8-hydroxyquinoline drugs. The printing and dyeing industry is used to make cyanine blue pigment and photosensitive pigment; rubber industry for the production of accelerators; Agriculture for the production of 8-hydroxyquinolinone and other pesticides. |
Risk Codes | R21/22 - Harmful in contact with skin and if swallowed. R38 - Irritating to the skin R41 - Risk of serious damage to eyes R68 - Possible risk of irreversible effects R40 - Limited evidence of a carcinogenic effect R37/38 - Irritating to respiratory system and skin. R51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R36/38 - Irritating to eyes and skin. R45 - May cause cancer |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S36 - Wear suitable protective clothing. S23 - Do not breathe vapour. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S53 - Avoid exposure - obtain special instructions before use. |
UN IDs | UN 2656 6.1/PG 3 |
WGK Germany | 2 |
RTECS | VA9275000 |
FLUKA BRAND F CODES | 8 |
TSCA | Yes |
HS Code | 29334900 |
Hazard Class | 6.1 |
Packing Group | III |
Toxicity | LD50 orally in rats: 460 mg/kg (Smyth) |
colorless liquid, long yellow, special odor. Relative density (water 1)1.09. Melting Point -14.5 °c. Boiling point 237.7 °c. The vapor pressure was 0. 13kPa/59.7 °c. Flash point 99 °c. Soluble in water, alcohol, ether, carbon disulfide and other organic solvents.
Combs synthesis method, using aromatic amine and 1,3 one two carbonyl compound reaction, first get high yield of B amino ketene, and then under the action of concentrated sulfuric acid, carbonyl oxygen after protonation of carbonyl carbon atoms to amino Ortho benzene ring carbon atom electrophilic attack, ring closure, and then dehydrated to
To quinoline.
used in organic synthesis, pharmaceutical and efficient pesticides, after oxidation can be made into pyridine hydroxy acid.
LogP | 2.04 at 22℃ |
(IARC) carcinogen classification | 2B (Vol. 121) 2019 |
NIST chemical information | information provided by: webbook.nist.gov (external link) |
EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
Overview | quinoline is also called benzopyridine, azapthalene, pyridine and benzene parallel compounds, is a heterocyclic aromatic organic compounds. It is a colorless hygroscopic liquid with strong odor at room temperature. When exposed to light, it will gradually turn light yellow and further Brown. The molecular formula is C9H7N, which is slightly soluble in water and soluble in ethanol, ether and many other organic solvents, there are two kinds of combination, respectively, called quinoline and isoquinoline. They are found in coal tar and bone tar, and the crude quinoline produced from coal tar contains about 4% isoquinoline. Isoquinoline has a melting point of 26.5 ° C., a boiling point of 242.2 ° C. (743 mmHg) and a density of 1.0986g/cm3(20 ° C.). Both of them are alkaline, isoquinoline is more alkaline than quinoline, and can form salts with strong acids, such as picrate and dichromate; Form quaternary ammonium salts with halogenated alkanes, etc. Quinoline is very aromatic, the benzene ring moiety is susceptible to electrophilic substitution reactions at two positions 5,8, for example, during nitration or sulfonation, 5-and 8-nitro and sulfo-quinoline were produced. The pyridine ring is partially stable, and the benzene ring is destroyed during oxidation, while the pyridine ring is unchanged. The infrared spectrum of quinoline has an absorption peak similar to 1-methylnaphthalene outside 3.27 μm, and the infrared absorption of Isoquinoline and naphthalene is very similar. The nature of isoquinoline is similar to that of quinoline. Nitration and sulfonation occur at the 5-position of the benzene ring, while nucleophilic reaction occurs at the 1-position, such as reaction with sodium Amino, and the 2 Position of the amino group in the 2. The acidic sulfate of quinoline is commonly used in industry to dissolve in ethanol, while the acidic sulfate of isoquinoline is insoluble in nature to separate. quinolines are toxic. Short-term exposure to quinoline vapor can cause corrosion of the nose, eyes, and respiratory tract, and may also cause dizziness and Nausea. The effect of prolonged exposure is uncertain, but quinoline is associated with liver injury. |
Discovery History | quinoline is a benzopyridine heterocyclic compound isolated from coal tar in 1834. Several years later, the compound was found to be a pyrolysis product of octylamine. Quinoline, also known as 1-azapthalene, 1-benzopyridine or benzo [B] pyridine, is a colorless, high-boiling liquid compound with a sweet odor. Its name comes from Quinine, an antimalarial drug isolated from cinchona bark, which evolved from the Spanish transliteration of Quinine, the name of cinchona bark in the local language of South America. |
quinoline compounds | quinoline structure widely exists in the molecular structure of a variety of natural products with important biological activity. Among them, Cinchona alkaloids Quinine and Quinidine and other alkaloids isolated from Rutaceae plants are an important class of Quinoline-containing natural products. For example, Toddaquinoline is an alkaloid isolated from the medicinal plant Toddalia asiatica, which has an inhibitory effect on the proliferation of liver cancer cells and the synthesis of deoxyribonucleic acid in liver cancer cells. Y-Fagarine is an alkaloid isolated from the plant Glycosmis arabea, is a protective agent against chemical carcinogenesis, and exhibits potent cytotoxicity against murine leukemia tumor P-288 cell line. another class of important alkaloids containing quinoline structure is the alkaloid of. Camptothecin is one of the most representative examples. The compound is a kind of alkaloid isolated from the Chinese endemic plant Camptotheca (Camptotheca acuminate) in 1966, which has significant anti-tumor activity. In recent years, camptothecin has been shown to have significant anti-retroviral activity, which may provide a new way of chemotherapy for AIDS. Cryptackieine is an alkaloid extracted from the West African shrub Cryptolepis sanguinolpta in 1996 and has significant antimalarial activity. |
Use | quinoline is used in the preparation of nicotinic acid and hydroxyquinoline drugs, cyanine blue pigment and photosensitive pigment, rubber accelerator and pesticide 8-hydroxyquinolinone and other products. The oral LD50 of rats was 460mg/kg. The production of cardiotonic agents, can also be used as acids, solvents, preservatives, etc.; Pharmaceutical industry for the production of nicotinic acid and 8-hydroxyquinoline drugs; Printing and dyeing industry for the preparation of cyanine blue pigment and photosensitive pigment; rubber industry for the production of accelerators; Agriculture for the production of 8-hydroxyquinolinone and other pesticides. 1. Quinoline is used to prepare nicotinic acid and hydroxyquinoline drugs, cyanine blue pigment and photosensitive pigment, rubber accelerator and pesticide 8-hydroxyquinolinone. The oral LD50 of rats was 460mg/kg. 2, used as organic synthesis reagents, Alkaline condensation agent and solvent. 3, used as analytical reagents, solvents, but also for the separation of vanadate and arsenate. 4, the production of cardiotonic agents, can also be used as acids, solvents, preservatives, etc.; Pharmaceutical industry for the production of nicotinic acid and 8-hydroxyquinoline drugs; Printing and dyeing industry for the preparation of cyanine blue pigment and photosensitive pigment; rubber industry for the production of accelerators; Agriculture for the production of 8-hydroxyquinoline copper and other pesticides. solvent. The refractive index of the mineral was measured. Separation of vanadate and arsenate. Assay of lignin. Determination of arsenic acid by microcrystallization method. Precipitants of zirconium, thorium, cerium, lanthanum, neodymium and praseodymium. Bismuth, antimony, nickel, rhenium, titanium, platinum, palladium, Iridium, osmium and gold were tested. Organic Synthesis. Dye manufacturing. Pharmaceutical antimalarial drugs. Specimen was preserved. |
production method | quinoline can be extracted from wash oil or naphthalene oil of coal tar. The naphthalene oil fraction and the wash oil fraction are washed with dilute sulfuric acid to obtain a quinoline sulfate base solution, and impurities such as neutral oil are removed by steam evaporation, and then decomposed with alkali or ammonia. After dehydration of the separated crude quinoline and its homologs, the crude quinoline containing 237.5 quinoline and 239.5 isoquinoline can be obtained by distillation with a high-yield distillation column and cutting out a fraction with a boiling range of 83%-15% ℃. The crude quinoline was treated with an aqueous solution of phosphoric acid having a concentration of 60%, cooled and filtered to obtain quinoline phosphate crystals. After decomposition with alkali, the purity of the product is 90%-92%. By repeating the treatment with phosphoric acid and recrystallization, Quinoline with a purity of 98%-99% was obtained. The most representative method for the synthesis of quinoline is Schloop synthesis: aniline, glycerol, sulfuric acid and oxidizing agent (such as nitrobenzene) are heated together, and cyclodehydrogenation is carried out to form quinoline. |
category | toxic substances |
toxicity grade | high toxicity |
Acute toxicity | oral-rat LD50: 331 mg/kg |
stimulation data | Skin-rabbits 10 mg/24 h mild; eye-rabbit 250 μg severe |
explosive hazard characteristics | explosive when mixed with air |
flammability hazard characteristics | open flame flammable; High thermal decomposition of toxic nitrogen oxide gas |
storage and transportation characteristics | The warehouse is ventilated and dried at low temperature, separate storage of food additives |
extinguishing agent | dry powder, foam, carbon dioxide, sand, water mist. |
spontaneous combustion temperature | 896 ° F. |
toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |