Cas no 78941-95-4 (5-Chloro-8-methylquinoline)

5-Chloro-8-methylquinoline is a halogenated quinoline derivative characterized by its chloro and methyl substituents at the 5- and 8-positions, respectively. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and coordination complexes. Its quinoline backbone offers structural rigidity, while the chloro and methyl groups enhance reactivity for further functionalization, such as cross-coupling or nucleophilic substitution reactions. The electron-withdrawing chloro group and electron-donating methyl group create a balanced electronic profile, making it useful in catalytic applications and ligand design. High purity grades ensure consistent performance in research and industrial processes.
5-Chloro-8-methylquinoline structure
5-Chloro-8-methylquinoline structure
Product Name:5-Chloro-8-methylquinoline
CAS No:78941-95-4
MF:C10H8ClN
MW:177.630221366882
MDL:MFCD00463515
CID:533636
PubChem ID:3948385
Update Time:2025-05-28

5-Chloro-8-methylquinoline Chemical and Physical Properties

Names and Identifiers

    • 5-Chloro-8-methylquinoline
    • Quinoline, 5-chloro-8-methyl-
    • Quinoline,5-chloro-8-methyl
    • 5-chloro-8-methyl-quinoline
    • V7775
    • ST24024052
    • Z2284394372
    • DTXSID70398168
    • AS-58726
    • 78941-95-4
    • MFCD00463515
    • EN300-50515
    • CS-0131202
    • Z600615482
    • A864946
    • SCHEMBL2056205
    • SR-01000388933
    • SB67613
    • IFLAB-BB F0349-0482
    • EU-0066723
    • SR-01000388933-1
    • AKOS001483093
    • D95571
    • 5-Chloro-8-methylquinoline (ACI)
    • DTXCID00349027
    • MDL： MFCD00463515
    • Inchi： 1S/C10H8ClN/c1-7-4-5-9(11)8-3-2-6-12-10(7)8/h2-6H,1H3
    • InChI Key： FOXFUGCJJRDBNG-UHFFFAOYSA-N
    • SMILES： ClC1C2C(=NC=CC=2)C(C)=CC=1

Computed Properties

  • Exact Mass: 177.03500
  • Monoisotopic Mass: 177.035
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 0
  • Complexity: 160
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 12.9
  • XLogP3: 3.2

Experimental Properties

  • PSA: 12.89000
  • LogP: 3.19660

5-Chloro-8-methylquinoline Customs Data

  • HS CODE：2933499090
  • Customs Data：

    China Customs Code:

    2933499090

    Overview:

    2933499090. Other compounds containing quinoline or isoquinoline ring system [but not further fused]. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933499090. other compounds containing in the structure a quinoline or isoquinoline ring-system (whether or not hydrogenated), not further fused. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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5-Chloro-8-methylquinoline Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Sulfuric acid Catalysts: Sodium iodide Solvents: Water ;  0.5 h, 140 °C; 6 h, 140 °C
1.2 Reagents: Sodium hydroxide Solvents: Water ;  pH 9 - 10
Reference
Rh(III)-Catalyzed straightforward arylation of 8-methyl/formylquinolines using diazo compounds
Ghosh, Bidhan; Samanta, Rajarshi, Chemical Communications (Cambridge, 2019, 55(48), 6886-6889

Production Method 2

Reaction Conditions
1.1 Reagents: Chlorine
Reference
Aromatic chlorination and iodination of 8-methylquinoline. Benzyl bromination of 5-halo-8-methylquinolines
Tochilkin, A. I.; Gracheva, I. N.; Kovel'man, I. R.; Prokof'ev, E. P., Khimiya Geterotsiklicheskikh Soedinenii, 1983, (10), 1373-6

Production Method 3

Reaction Conditions
1.1 Reagents: Sulfuric acid ,  Sodium iodide Solvents: Water ;  3.5 h, 140 - 145 °C
Reference
Catalytic aerobic oxidation of substituted 8-methylquinolines in PdII-2,6-pyridinedicarboxylic acid systems
Zhang, Jing; Khaskin, Eugene; Anderson, Nicholas P.; Zavalij, Peter Y.; Vedernikov, Andrei N., Chemical Communications (Cambridge, 2008, (31), 3625-3627

Production Method 4

Reaction Conditions
1.1 Reagents: Sulfuric acid Catalysts: Sodium iodide Solvents: Water ;  1 h, 140 °C; 2.5 h, 140 - 145 °C
1.2 Reagents: Sodium hydroxide Solvents: Water ;  pH 7
Reference
Cp*Rh(III)-Catalyzed Mild Addition of C(sp3)-H Bonds to α,β-Unsaturated Aldehydes and Ketones
Liu, Bingxian; Hu, Panjie; Zhou, Xukai; Bai, Dachang; Chang, Junbiao; et al, Organic Letters, 2017, 19(8), 2086-2089

Production Method 5

Reaction Conditions
1.1 Reagents: Isopropanol ,  Stannous chloride Catalysts: Palladium Solvents: 1,4-Dioxane ,  Water ;  rt; rt → 180 °C; 40 h, 180 °C
Reference
Reduction of nitroarenes followed by propanol group transfer from tris(3-hydroxypropyl)- amine and cyclization leading to quinolines under heterogeneous Pd-C catalysis
Cho, Chan Sik; Kim, Tae Gyun; Yoon, Nam Sik, Applied Organometallic Chemistry, 2010, 24(4), 291-293

Production Method 6

Reaction Conditions
1.1 Reagents: Potassium iodide ,  Potassium persulfate ,  Oxygen Catalysts: Silver carbonate Solvents: Diethylformamide ;  rt → 120 °C; 12 h, 120 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  neutralized
Reference
From Anilines to Quinolines: Iodide- and Silver-Mediated Aerobic Double C-H Oxidative Annulation-Aromatization
Wu, Jiwei; Liao, Zhixiong; Liu, Dong; Chiang, Chien-Wei; Li, Zheng; et al, Chemistry - A European Journal, 2017, 23(63), 15874-15878

Production Method 7

Reaction Conditions
1.1 Reagents: Sulfuric acid ,  Sodium iodide ;  30 min, 140 °C; 24 h, 140 °C
1.2 Reagents: Sodium hydroxide Solvents: Water ;  pH 9 - 10
Reference
Cobalt-catalyzed ring-opening addition of azabenzonorbornadienes via C(sp3)-H bond activation of 8-methylquinoline
Tan, Heng; Khan, Ruhima; Xu, Dandan; Zhou, Yongyun; Zhang, Xuexin; et al, Chemical Communications (Cambridge, 2020, 56(83), 12570-12573

Production Method 8

Reaction Conditions
1.1 Reagents: Sulfuric acid Catalysts: Sodium iodide Solvents: Water ;  0.5 h, 140 °C; 3.5 h, 140 - 145 °C; 145 °C → rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  pH 8 - 11, cooled
Reference
Palladium-Catalyzed C-H Bond Functionalization Reactions Using Phosphate/Sulfonate Hypervalent Iodine Reagents
He, Yimiao ; Huang, Lilan; Xie, Limei; Liu, Peng; Wei, Qiongmei; et al, Journal of Organic Chemistry, 2019, 84(16), 10088-10101

Production Method 9

Reaction Conditions
1.1 Reagents: Sulfuric acid ,  Sodium iodide Solvents: Water ;  0.5 h, 140 °C; 6 h, 140 °C
1.2 Reagents: Sodium hydroxide Solvents: Water ;  pH 9 - 10
Reference
Rhodium(III)-Catalyzed Direct Coupling of Quinoline-8-Carbaldehydes with (Het)Arylboronic Acids for the Synthesis of 8-Aryloylquinolines
Lyu, Xue-Li; Huang, Shi-Sheng; Huang, Yuan-Qiong; Li, Yong-Qiang; Song, Hong-Jian; et al, Journal of Organic Chemistry, 2020, 85(15), 10271-10282

Production Method 10

Reaction Conditions
1.1 Reagents: Arsenic oxide (As2O5) ,  Sulfuric acid Catalysts: Triacylglycerol lipase ;  overnight, 160 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  cooled
Reference
C-H 18F-fluorination of 8-methylquinolines with Ag[18F]F
Lee, So Jeong; Brooks, Allen F.; Ichiishi, Naoko; Makaravage, Katarina J.; Mossine, Andrew V.; et al, Chemical Communications (Cambridge, 2019, 55(20), 2976-2979

Production Method 11

Reaction Conditions
1.1 Reagents: Chlorine
Reference
Halo-substituted 6-, 7-, and 8-(N-methyl-N-propyn-2-ylaminomethyl)quinolines: synthesis and antimonoamine oxidase activity
Kovel'man, I. R.; Tochilkin, A. I.; Ioffina, D. I.; Gorkin, V. Z.; Makarenko, A. V.; et al, Khimiko-Farmatsevticheskii Zhurnal, 1989, 23(9), 1080-4

Production Method 12

Reaction Conditions
1.1 Reagents: Sulfuric acid Catalysts: Sodium iodide Solvents: Water ;  0.5 h, 140 °C; 3.5 h, 140 - 145 °C; 145 °C → rt; cooled
1.2 Reagents: Sodium hydroxide Solvents: Water ;  pH 8 - 11, cooled
Reference
Palladium-Catalyzed C(sp3)-H Biarylation of 8-Methyl Quinolines with Cyclic Diaryliodonium Salts to Access Functionalized Biaryls and Fluorene Derivatives
Maurya, Naveen Kumar; Yadav, Suman; Chaudhary, Dhananjay; Kumar, Dharmendra; Ishu, Km; et al, Journal of Organic Chemistry, 2022, 87(21), 13744-13749

Production Method 13

Reaction Conditions
1.1 Reagents: Sulfuric acid ,  Sodium iodide Solvents: Water ;  0.5 h, 140 °C; 6 h, 140 - 145 °C; 145 °C → rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  pH 8 - 11, cooled
Reference
RhIII-Catalyzed Direct Heteroarylation of C(sp3)-H and C(sp2)-H Bonds in Heterocycles with N-Heteroaromatic Boronates
Wang, Huai-Wei; Wu, Jia-Xue; Qiao, Yu-Han; Li, Yong-Fei; Li, Da-Cheng; et al, Organic Letters, 2021, 23(18), 7177-7182

Production Method 14

Reaction Conditions
1.1 Reagents: Chlorosuccinimide ,  Sulfuric acid ;  5 °C; 18 h, 5 °C
1.2 Reagents: Sodium hydroxide Solvents: Water ;  pH 11, 0 °C
Reference
Cobalt(III)-Catalyzed Alkylation of Primary C(sp3)-H Bonds with Diazo Compounds
Yan, Sheng-Yi; Ling, Peng-Xiang; Shi, Bing-Feng, Advanced Synthesis & Catalysis, 2017, 359(17), 2912-2917

Production Method 15

Reaction Conditions
1.1 Reagents: Sulfuric acid Catalysts: Sodium iodide Solvents: Water ;  0.5 h, 140 °C; 3.5 h, 140 - 145 °C; 145 °C → rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  pH 8 - 11, cooled
Reference
Rh-Catalyzed Direct Amination of Unactivated C(sp3)-H bond with Anthranils Under Mild Conditions
Tang, Conghui; Zou, Miancheng; Liu, Jianzhong; Wen, Xiaojin; Sun, Xiang; et al, Chemistry - A European Journal, 2016, 22(32), 11165-11169

Production Method 16

Reaction Conditions
1.1 Reagents: Sulfuric acid ,  Sodium iodide Solvents: Water ;  0.5 h, 140 °C; 3.5 h, 140 - 145 °C; 145 °C → rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  pH 8 - 11, cooled
Reference
Rhodium(III)-Catalyzed Intermolecular Amidation with Azides via C(sp3)-H Functionalization
Wang, Nuancheng; Li, Renhe; Li, Liubo; Xu, Shansheng; Song, Haibin; et al, Journal of Organic Chemistry, 2014, 79(11), 5379-5385

Production Method 17

Reaction Conditions
1.1 Reagents: Trichloroisocyanuric acid Solvents: Acetonitrile ;  5 - 6 h, rt
Reference
A general method for the metal-free, regioselective, remote C-H halogenation of 8-substituted quinolines
Motati, Damoder Reddy; Uredi, Dilipkumar; Watkins, E. Blake, Chemical Science, 2018, 9(7), 1782-1788

5-Chloro-8-methylquinoline Raw materials

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Amadis Chemical Company Limited
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(CAS:78941-95-4)5-Chloro-8-methylquinoline
Order Number:A864946
Stock Status:in Stock
Quantity:5g
Purity:99%
Pricing Information Last Updated:Friday, 30 August 2024 08:49
Price ($):296.0

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Amadis Chemical Company Limited
(CAS:78941-95-4)5-Chloro-8-methylquinoline
A864946
Purity:99%
Quantity:5g
Price ($):296.0
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