Quinoline 喹啉

CAS 91-22-5 MFCD00006736

化学结构图

91-22-5
SMILES: c1ccc2ncccc2c1

化学属性

Mol. FormulaC9H7N
Mol. Weight129.16
Refractive index1.6250 to 1.6290
Boiling Point-
Density1.093
Melting Point-17 - -13
Flash Point101.11°C
SolubilityMore soluble in hot than cold water. Miscible with alcohol, ether
TSCAYes
Autoignition Point896 °F
Vapor Density4.5 (vs air)
Vapor Pressure0.07 mmHg ( 20 °C)
Stability对光敏感

别名和识别编码

Chemical NameQuinoline
Synonym Quinoline {LY} Quinoline {} {LY} Quinoline {} {} {LY} Quinoline {} {} {} {LY} Quinoline {} {} {} {} {LY} Quinoline {} {} {} {} {} {LY} Quinoline {} {} {} {} {} {} {LY} Quinoline {} {} {} {} {} {} {} {LY} Quinoline {} {} {} {} {} {} {} {} {LY} Quinoline {} {} {} {} {} {} {} {} {} {LY} Quinoline {} {} {} {} {} {} {} {} {} {} {LY} Quinoline {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Quinoline {} {} {} {} {} {} {} {} {} {} {} {} {LY} Quinoline {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Quinoline {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Quinoline {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Quinoline {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Quinoline {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Quinoline {} {} {} {} {} {}
CAS Number91-22-5
PubChem Substance ID7047
EC Number202-051-6
Beilstein Registry Number107477
MDL Number-
Reaxys-RN107477
Merck Number8068
Chemical Name Translation喹啉
Wiswesser Line NotationT66 BNJ
LabNetwork Molecule IDLN00193846
InChIInChI=1S/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H
Canonical SMILESC12=CC=CC=C1N=CC=C2
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分类

  • {SNA} Ephedra sinica, Ligands and Metal Complex Precursors, Organic and Printed Electronics, Phytochemicals by Plant (Food/Spice/Herb), Synthetic Tools and Reagents, 材料科学, 细胞生物学, 营养研究
  • {SNA} Alphabetical Listings, Bioactive Small Molecules, Flavors and Fragrances, Q, Q-Z, 细胞生物学
  • {SNA} Alphabetical Listings, Flavors and Fragrances, Q-Z
  • {SNA} Bioactive Small Molecules, Ephedra sinica, Ligands and Metal Complex Precursors, Materials Science, Nutrition Research,
  • {SNA} Alphabetical Listings, Bioactive Small Molecules, Flavors and Fragrances, Q,
  • Bioactive Small Molecules,

产品应用

  • 溶剂。测定矿物的折光率。分离钒酸盐及砷酸盐。检定木质素。显微结晶方法测定砷酸。锆、钍、铈、镧、钕和镨的沉淀剂。测试铋、锑、镍、铼、钛、铂、钯、铱、锇和金等。有机合成。染料制造。医药抗疟药。标本防腐。

相关文献及参考

  • {ALF
  • 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.
  • 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 co
  • 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 a
  • 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).
  • 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).
  • Dehydrohalogenation base; see, e.g.: Org. Synth. Coll., 4, 608 (1963).

安全信息

GHS Symbol
WGK Germany2
Hazard Codes 6.1 T,N Xn
Hazard statements
  • H315 Causes skin irritation 会刺激皮肤
  • H301 Toxic if swallowed 吞食有毒
  • H312 Harmful in contact with skin 皮肤接触有害
  • H350 May cause cancer 可能致癌
  • H341 Suspected of causing genetic defects 怀疑导致遗传性缺陷
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H411 Toxictoaquaticlifewithlonglastingeffects 对水生生物有毒性并具有长期影响。
  • H302 Harmful if swallowed 吞食有害
  • H311 Toxic in contact with skin 皮肤接触中毒
Personal Protective Equipment Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
RTECSVA9275000
Precautionary statements
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西,喝水或吸烟。
  • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
  • P273 Avoid release to the environment. 避免释放到环境中。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P301+P310
  • P301+P312+P330
  • P302+P350
  • P302+P352+P312+P361+P364
  • P304+P340+P312
  • P305+P351+P338
  • P305+P351+P338+P337+P313
  • P308+
  • P308+P311
  • P308+P313
  • P332+P313
  • P337+P313
  • P391 Collect spillage. Hazardous to the aquatic environment 收集对水环境有危害的泄漏物。
  • P403+P233
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Signal word Danger
UN Number 2656 UN2656
Risk Statements
  • R21/22 Harmful in contact with skin and if swallowed 皮肤接触和不慎吞咽有害
  • R36/38 Irritating to eyes and skin 对眼睛和皮肤有刺激性
  • R45 May cause cancer 可能致癌
  • R51/53
  • R68 Possible risk of irreversible effects 可能有不可挽回的作用的危险
Safety Statements
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时,立即求医(可能时出示标签);
  • S53 Avoid exposure - obtain special instructions before use 避免接触,使用前获得特别指示说明;
  • S61 Avoid release to the environment. Refer to special instructions/safety data sheet 避免释放到环境中,参考特别指示/安全收据说明书;
Storage condition Store at room temperature {LY} Store at room temperature {} {LY} Store at room temperature {} {} {LY} Store at room temperature {} {} {} {LY} Store at room temperature {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
Packing GroupIII
Hazard Class6.1
Warnings 危化品目录(2015)
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 7770 mg/kg/37W-C
TOXIC EFFECTS :
   Tumorigenic - neoplastic by RTECS criteria
   Liver - tumors
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   36,329,1976

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 50 gm/kg/30W-C
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Liver - tumors
REFERENCE :
   GANNA2 Gann.  Japanese Journal of Cancer Research.  (Tokyo, Japan)  V.1-75,
   1907-84.  For publisher information, see JJCREP.  Volume(issue)/page/year:
   68,785,1977

TYPE OF TEST            : TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 23 gm/kg/30W-C
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Liver - tumors
REFERENCE :
   GANNA2 Gann.  Japanese Journal of Cancer Research.  (Tokyo, Japan)  V.1-75,
   1907-84.  For publisher information, see JJCREP.  Volume(issue)/page/year:
   68,785,1977

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 9042 ug/kg/15D-I
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Liver - tumors
   Blood - lymphoma, including Hodgkin's disease
REFERENCE :
   JJCREP Japanese Journal of Cancer Research. (Elsevier Science Pub. BV, POB
   211, 1000 AE Amsterdam, Netherlands)  V.76-    1985-
   Volume(issue)/page/year: 78,139,1987

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 331 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   85JCAE "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J.,
   Prague, Czechoslovakia, Avicenum, 1986  Volume(issue)/page/year: -,848,1986

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Administration onto the skin
SPECIES OBSERVED        : Rodent - rabbit
DOSE/DURATION           : 540 uL/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   AMIHBC AMA Archives of Industrial Hygiene and Occupational Medicine.
   (Chicago, IL)  V.2-10, 1950-54. For publisher information, see AEHLAU.
   Volume(issue)/page/year: 4,119,1951

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Amphibian - frog
DOSE/DURATION           : 150 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig,
   Ger. Dem. Rep.)  Volume(issue)/page/year: 4,1289,1935

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rabbit
DOSE/DURATION           : 200 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig,
   Ger. Dem. Rep.)  Volume(issue)/page/year: 4,1289,1935

TYPE OF TEST            : Micronucleus test
ROUTE OF EXPOSURE       : Intraperitoneal
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION           : 50 mg/kg
REFERENCE :
   TCMUD8 Teratogenesis, Carcinogenesis, and Mutagenesis.  (Alan R. Liss, Inc.,
   41 E. 11th St., New York, NY 10003)  V.1-    1980- Volume(issue)/page/year:
   9,111,1989

TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Non-mammalian species Embryo
DOSE/DURATION           : 460 mmol/L/10M (Continuous)
REFERENCE :
   CHROAU Chromosoma.  (Springer-Verlag New York, Inc., Service Center, 44
   Hartz Way, Secaucus, NJ 07094)  V.1-    1939-  Volume(issue)/page/year:
   56,289,1976

TYPE OF TEST            : Cytogenetic analysis
TEST SYSTEM             : Rodent - hamster Lung
DOSE/DURATION           : 100 mg/L
REFERENCE :
   ATSUDG Archives of Toxicology, Supplement.  (Springer-Verlag New York, Inc.,
   Service Center, 44 Hartz Way, Secaucus, NJ 07094)  No.1-    1978-
   Volume(issue)/page/year: 4,41,1980

TYPE OF TEST            : DNA damage
TEST SYSTEM             : Rodent - rat Liver
DOSE/DURATION           : 1 mmol/L
REFERENCE :
   SinJF# Personal Communication from J.F. Sina, Merck Institute for
   Therapeutic Research, West Point, PA 19486, Oct. 26, 1982
   Volume(issue)/page/y

TYPE OF TEST            : Sister chromatid exchange
TEST SYSTEM             : Rodent - hamster Ovary
DOSE/DURATION           : 110 ug/L
REFERENCE :
   ENMUDM Environmental Mutagenesis.  (New York, NY)  V.1-9, 1979-87.  For
   publisher information, see EMMUEG.  Volume(issue)/page/year: 7,1,1985

TYPE OF TEST            : DNA damage
TEST SYSTEM             : Rodent - rat Liver
DOSE/DURATION           : 1 mmol/L
REFERENCE :
   SinJF# Personal Communication from J.F. Sina, Merck Institute for
   Therapeutic Research, West Point, PA 19486, Oct. 26, 1982
   Volu

Restrict 危险品

其他信息

  • 概述:喹啉也叫做苯并吡啶、氮杂萘,为吡啶与苯并联的化合物,是一个杂环芳香性有机化合物。常温下为具有强烈臭味的无色吸湿性液体,暴露在光下,会慢慢变成淡黄色,进一步变成棕色,分子式是C9H7N,微溶于水,易溶于乙醇、乙醚等很多有机溶剂,有两种并合方式,分别称为喹啉和异喹啉。它们存在于煤焦油和骨焦油内,由煤焦油制得的粗喹啉含有约4%的异喹啉。异喹啉的熔点26.5℃,沸点242.2℃(743毫米汞柱),密度1.0986g/cm3(20℃),其气味与喹啉完全不同。二者都具有碱性,异喹啉比喹啉碱性更强,都可以与强酸生成盐,如苦味酸盐和重铬酸盐;与卤代烷形成四级铵盐等,喹啉的芳香性很强,苯环部分容易在5,8两位上发生亲电取代反应,例如在硝化或磺化时,产生5-和8-硝基和磺基喹啉。吡啶环部分稳定,在氧化时,苯环被破坏,而吡啶环不变。喹啉的红外光谱在3.27微米外有一个与1-甲基萘相似的吸收峰,异喹啉与萘的红外吸收很相似。异喹啉的性质与喹啉近似,硝化和磺化在苯环的5位上发生,亲核反应则在1位上发生,如与氨基钠反应,生成1-氨基异喹啉,而喹啉在2位上氨基化。工业上常用喹啉的酸性硫酸盐溶于乙醇,而异喹啉的酸性硫酸盐则不溶的性质来分离。 喹啉是有毒性的,短时间暴露在喹啉蒸汽中会导致鼻子、眼睛和呼吸道被腐蚀,也可能导致头昏和恶心。长时间暴露的影响还不确定,不过喹啉与肝损伤有一定的关系。
  • 下游产品:3-氨基奎宁环盐酸盐 --> 喹啉酸 --> 4-羟基苯乙烯 --> 8-羟基喹啉 --> 4-氰基苯乙烯 --> 2-氨基喹啉 --> 5-氨基苯并噻吩 --> 4-溴喹啉 --> 4-硝基苯乙烯 --> 3-氟喹啉-4-羧酸 --> 4-氨基喹啉 --> 3,4-二甲基噻吩并[2,3-B]噻吩-2-甲醛 --> 4-氯-6-三氟甲基嘧啶 --> 2-羟基喹啉 --> 2-溴喹啉 --> 1-甲基-5-硝基-1H-吲哚 --> 铬黑 T --> 灭草喹 --> 硝酸硫胺 --> 盐酸硫胺 --> 1-甲基-1,2,3,4-四氢喹啉-6-甲醛 --> 4-硝基喹啉-N-氧化物 --> 8-羟基喹啉铜 --> 3-氰基喹啉 --> 4-甲氧基喹啉 --> 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 --> 喹啉-8-磺酰氯 --> 5-氨基吲哚 --> (Z)-3,4,5,4',-四甲氧基-3'-羟基二苯乙烯 --> 2-氰基喹啉 --> 5-溴-6-氯烟酸 --> 2-苯基喹啉 --> 喹哪啶酸 --> 3-甲基呋喃 --> 喹啉黄 --> 4-乙烯基-2-甲氧基苯酚 --> 异氰酸己酯
  • Sigma Aldrich:91-22-5(sigmaaldrich)
  • 蒸气压:0.07 mm Hg ( 20 °C)
  • {Chemicalbook
  • 灭火剂:干粉、泡沫、二氧化碳、砂土、雾状水。
  • Acros Organics:喹啉 Quinoline, 96%(91-22-5)
  • 可燃性危险特性:明火可燃; 高热分解有毒的氧化氮气体
  • 日久变黄,有特殊不愉快的气味。有吸湿性,能从空气中吸收22%水分。能随水蒸气挥发。见光或露置后色变深,如显著变色,必须重新蒸馏。弱碱性,对酚酞呈中性,与强酸形成可溶性盐类。能与醇、醚及二硫化碳混溶,易溶于热水,难溶于冷水,能溶解硫、磷和三氧化砷。中等毒,半数致死量(大鼠,经口)460mg/kg。
  • F:8
  • 食品添加剂最大允许使用量最大允许残留量标准:添加剂中文名称 允许使用该种添加剂的食品中文名称 添加剂功能 最大允许使用量(g/kg) 最大允许残留量(g/kg) 喹啉 食品 食品用香料 用于配制香精的各香料成分不得超过在GB 2760中的最
  • 方法一:喹啉可从煤焦油的洗油或萘油中提取。萘油馏分和洗油馏分用稀硫酸洗涤,得到硫酸喹啉盐基溶液,用蒸气蒸去除中性油等杂质,再用碱或氨分解。分离出来的粗喹啉及其同系物经脱水后,用高产蒸馏塔精馏,切取沸程为237.5-239.5℃的馏分段,可以得到含喹啉83%、异喹啉15%的粗喹啉。将粗喹啉用浓度为60%的磷酸水溶液处理,冷却后过滤,即得到喹啉磷酸盐结晶。用碱分解后,产品纯度为9
  • {Che
  • 图谱信息:喹啉(91-22-5)红外
  • 日久变黄,有特殊不愉快的气味。有吸湿性,能从空气中吸收22%水分
  • 毒性分级:高毒

系列性分类


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