Cas no 932-96-7 (4-Chloro-N-methylaniline)

4-Chloro-N-methylaniline (CAS 932-96-7) is an organic compound featuring a chloro-substituted aromatic ring and a secondary amine functional group. This chemical serves as a versatile intermediate in organic synthesis, particularly in the production of dyes, pharmaceuticals, and agrochemicals. Its chloro and methylamino substituents enhance reactivity, enabling selective functionalization in coupling and substitution reactions. The compound exhibits moderate solubility in organic solvents, facilitating its use in homogeneous reaction conditions. Careful handling is required due to its potential toxicity and sensitivity to oxidation. Its structural properties make it valuable for constructing complex molecules in research and industrial applications. Storage under inert conditions is recommended to maintain stability.
4-Chloro-N-methylaniline structure
4-Chloro-N-methylaniline structure
Product Name:4-Chloro-N-methylaniline
CAS No:932-96-7
MF:C7H8ClN
MW:141.598120689392
MDL:MFCD00000614
CID:40317
PubChem ID:24852631
Update Time:2025-05-21

4-Chloro-N-methylaniline Chemical and Physical Properties

Names and Identifiers

    • 4-Chloro-N-methylaniline
    • 4-Chloro-N-toluidine
    • 4-CHLOR-N-METHYLANILIN
    • 4-chloro-N-methyl-aniline
    • Aniline,p-chloro-N-methyl
    • Aniline,p-chloro-N-methyl-(7CI,8CI)
    • Benzenamine,4-chloro-N-methyl
    • BENZENAMINE,4-CHLORO-N-METHYL-
    • EINECS 213-262-8
    • N-(P-CHLOROBENZYL)METHYLAMINE
    • N-methyl N-4-chlorophenylamine
    • N-methyl-4-chloroaniline
    • N-methyl-4-Cl-aniline
    • N-methyl-p-chloroaniline
    • p-chloro-N-methylaniline
    • Aniline,p-chloro-N-methyl- (6CI,7CI,8CI)
    • 4-Chloro-N-methylbenzenamine
    • N-(4-Chlorophenyl)-N-methylamine
    • N-(4-Chlorophenyl)methylamine
    • p-(Methylamino)chlorobenzene
    • Benzenamine, 4-chloro-N-methyl-
    • Aniline, p-chloro-N-methyl-
    • 2IXY9JA2P8
    • XCEYKKJMLOFDSS-UHFFFAOYSA-N
    • Aniline, p-chloro-N-methyl- (7CI,8CI)
    • chloro-n-methylaniline
    • PubChem23344
    • N-methyl-4-chloro aniline
    • 4-chloro-N-meth
    • 4-Chloro-N-methylbenzenamine (ACI)
    • Aniline, p-chloro-N-methyl- (6CI, 7CI, 8CI)
    • aniline, 4-chloro-N-methyl-
    • 4-chloro-N-methyl aniline
    • DB-057391
    • 4-12-00-01168 (Beilstein Handbook Reference)
    • CCRIS 2889
    • J-640269
    • AKOS000254181
    • BRN 2205846
    • C1620
    • DTXCID00161822
    • Aniline, p-chloro-N-methyl-(7CI,8CI)
    • J-800261
    • BIDD:GT0836
    • 932-96-7
    • DS-6021
    • EN300-66346
    • Q27254800
    • SCHEMBL4758786
    • 4-Chloro-N-methylaniline, 97%
    • DTXSID80239331
    • SCHEMBL228690
    • UNII-2IXY9JA2P8
    • DCA_142.0419_14.6
    • (4-chloro-phenyl)-methyl-amine
    • (4-chloro-phenyl)-methyl amine
    • MFCD00000614
    • CS-W018297
    • NS00000650
    • MDL: MFCD00000614
    • Inchi: 1S/C7H8ClN/c1-9-7-4-2-6(8)3-5-7/h2-5,9H,1H3
    • InChI Key: XCEYKKJMLOFDSS-UHFFFAOYSA-N
    • SMILES: ClC1C=CC(NC)=CC=1
    • BRN: 2205846

Computed Properties

  • Exact Mass: 141.03500
  • Monoisotopic Mass: 141.034527
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 9
  • Rotatable Bond Count: 1
  • Complexity: 77
  • 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
  • XLogP3: 2.8
  • Topological Polar Surface Area: 12
  • Surface Charge: 0
  • Tautomer Count: nothing

Experimental Properties

  • Color/Form: Not determined
  • Density: 1.169?g/mL?at 25?°C(lit.)
  • Boiling Point: 142°C/40mmHg(lit.)
  • Flash Point: Fahrenheit: 125.6 ° f
    Celsius: 52 ° c
  • Refractive Index: n20/D 1.584(lit.)
  • PSA: 12.03000
  • LogP: 2.45470
  • FEMA: 3184
  • Solubility: Not determined
  • Sensitiveness: Sensitive to air

4-Chloro-N-methylaniline Security Information

4-Chloro-N-methylaniline Pricemore >>

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4-Chloro-N-methylaniline Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Potassium methoxide Catalysts: 2792159-73-8 Solvents: Methanol ;  6 h, 115 °C
Reference
Investigation of NNN Pincer Ruthenium(II) Complexes with a Pendant Hydroxyl Group for N-Monomethylation of amines and Nitroarenes by Methanol
Li, Kangkang; Li, Jin-Feng; Yin, Bing; Zeng, Fanlong, ChemCatChem, 2022, 14(11),

Production Method 2

Reaction Conditions
1.1 Reagents: Sodium methoxide Catalysts: 2056267-35-5 Solvents: Methanol ;  12 h, 110 °C
Reference
Tandem Transformation of Nitro Compounds into N-Methylated Amines: Greener Strategy for the Utilization of Methanol as a Methylating Agent
Paul, Bhaskar; Shee, Sujan; Chakrabarti, Kaushik; Kundu, Sabuj, ChemSusChem, 2017, 10(11), 2370-2374

Production Method 3

Reaction Conditions
1.1 Catalysts: Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, lanthanum(3+) salt (3:1) Solvents: Dimethylformamide ;  1 h, rt
1.2 Reagents: Water ;  rt
Reference
La-Catalyzed Decarbonylation of Formamides and Its Applications
Li, Shaocheng; Rajeshkumar, Thayalan; Liu, Jincheng; Maron, Laurent ; Zhou, Xigeng, Organic Letters, 2023, 25(1), 163-168

Production Method 4

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide Catalysts: Iridium(1+), dicarbonyl[1,2,3,5,6,7-hexahydro-1,3,5,7-tetramethylbenzo[1,2-d:4,5… Solvents: Methanol ;  rt → 130 °C; 12 h, 130 °C
Reference
Sustainable and Selective Monomethylation of Anilines by Methanol with Solid Molecular NHC-Ir Catalysts
Chen, Jiangbo; Wu, Jiajie; Tu, Tao, ACS Sustainable Chemistry & Engineering, 2017, 5(12), 11744-11751

Production Method 5

Reaction Conditions
1.1 Reagents: Potassium hydroxide Catalysts: Cuprous iodide ,  6,7-Dihydro-5H-quinolin-8-one oxime Solvents: Water ;  12 h, 25 °C
Reference
Room-Temperature Copper-Catalyzed Arylation of Dimethylamine and Methylamine in Neat Water
Wang, Deping; Kuang, Daizhi; Zhang, Fuxing; Yang, Chunlin; Zhu, Xiaoming, Advanced Synthesis & Catalysis, 2015, 357(4), 714-718

Production Method 6

Reaction Conditions
1.1 Reagents: Hydrochloric acid Solvents: Ethylene glycol ,  Water ;  rt → reflux; reflux
Reference
Highly efficient N-monomethylation of primary aryl amines
Peng, Yiyuan; Liu, Hanliang; Tang, Min; Cai, Lisheng; Pike, Victor, Chinese Journal of Chemistry, 2009, 27(7), 1339-1344

Production Method 7

Reaction Conditions
1.1 Reagents: Alumina (potassium fluoride supported on) Catalysts: Potassium fluoride (supported on alumina) ;  20 min
Reference
Microwave-assisted deformylation of N-aryl formamide by KF on basic Al2O3
Ge, Yiyu; Hu, Longqin, Tetrahedron Letters, 2007, 48(26), 4585-4588

Production Method 8

Reaction Conditions
1.1 120 °C
1.2 Reagents: Borate(1-), (acetato-κO)trihydro-, sodium (1:1), (T-4)- Solvents: Tetrahydrofuran ;  1 h, rt; 2 h, rt
1.3 Reagents: Sodium hydroxide Solvents: Water
Reference
A facile protocol for the synthesis of mono-N-methyl anilines via formimidate intermediates
Sun, Nan; Wang, Shuai; Mo, Weimin; Hu, Baoxiang; Shen, Zhenlu; et al, Tetrahedron, 2010, 66(35), 7142-7148

Production Method 9

Reaction Conditions
1.1 Reagents: Sulfuric acid Solvents: Water
Reference
Microwave-assisted one-pot synthesis of N-alkyl aromatic amines from benzanilide in presence of phase transfer catalyst
Tapase, Arvind B.; Shinde, Narayan; Shinde, Devanand, Organic Chemistry: An Indian Journal, 2010, 6(1), 52-55

Production Method 10

Reaction Conditions
1.1 Reagents: Cesium carbonate Catalysts: Iridium (complex with 2,6-dicyanopyridine homopolymer, pentamethylcyclopentadienyl, and chloride) ,  2,6-Pyridinedicarbonitrile, homopolymer (complex with pentamethylcyclopentadienyliridium(III) dichloride dimer) Solvents: Methanol ;  12 h, 125 °C
Reference
Recyclable covalent triazine framework-supported iridium catalyst for the N-methylation of amines with methanol in the presence of carbonate
Liu, Peng ; Yang, Jiazhi; Ai, Yao; Hao, Shushu; Chen, Xiaozhong; et al, Journal of Catalysis, 2021, 396, 281-290

Production Method 11

Reaction Conditions
1.1 Catalysts: Potassium carbonate ,  Iridium(2+), diammine[1,3-dihydro-1,3-bis(1-methylethyl)-2H-imidazol-2-ylidene][… ;  17 h, 120 °C
Reference
Efficient and Versatile Catalytic Systems for the N -Methylation of Primary Amines with Methanol Catalyzed by N -Heterocyclic Carbene Complexes of Iridium
Toyooka, Genki; Tuji, Akiko; Fujita, Ken-ichi, Synthesis, 2018, 50(23), 4617-4626

Production Method 12

Reaction Conditions
1.1 Catalysts: Potassium tert-butoxide ,  Iridium (encapsulated within yolk-shell-structured mesoporous nanospheres) Solvents: Methanol ;  30 h, 170 °C
Reference
Selective N-Monomethylation of Amines and Nitroarenes using Methanol over an Encapsulated Iridium Nanocatalyst
Fu, Aixiao; Liu, Qiang; Jiang, Mingxiang; Xu, Guoqiang, Asian Journal of Organic Chemistry, 2019, 8(4), 487-491

Production Method 13

Reaction Conditions
1.1 Reagents: Cesium carbonate Catalysts: Iridium(1+), (2,2′-bi-1H-benzimidazole-κN3,κN3′)chloro[(1,2,3,4,5-η)-1,2,3,4,5-p… ;  12 h, 120 °C; 120 °C → rt
Reference
N-Methylation of amines with methanol catalyzed by a Cp*Ir complex bearing a functional 2,2'-bibenzimidazole ligand
Liang, Ran; Li, Shun; Wang, Rongzhou; Lu, Lei; Li, Feng, Organic Letters, 2017, 19(21), 5790-5793

Production Method 14

Reaction Conditions
1.1 Reagents: Potassium hydroxide Catalysts: Ruthenium(1+), chloro[(3-methyl-1H-imidazol-1-yl-2(3H)-ylidene)methylene[1-methy… ;  24 h, 130 °C
Reference
Ruthenium(II) Complexes of Heteroditopic N-Heterocyclic Carbene Ligands: Efficient Catalysts for C-N Bond Formation via a Hydrogen-Borrowing Strategy under Solvent-Free Conditions
Donthireddy, S. N. R.; Mathoor Illam, Praseetha; Rit, Arnab, Inorganic Chemistry, 2020, 59(3), 1835-1847

Production Method 15

Reaction Conditions
1.1 Catalysts: Sodium carbonate (celite-supported) Solvents: Ethanol ;  2 h, reflux
Reference
A highly active catalyst supported molecular sieves-NaHCO3 mixture for the selective and advantageous N-monoalkylation of amines
Das, Asish R.; Medda, Arunima; Singha, Raghunath; Guchhait, Nikhil, Journal of the Indian Chemical Society, 2009, 86(8), 841-848

Production Method 16

Reaction Conditions
1.1 Reagents: Potassium hydroxide Catalysts: Iridium(2+), [μ-([2,2′-bipyrimidine]-4,4′,6,6′-tetrol-κN1,κN1′:κN3,κN3′)]dichlor… Solvents: Water ;  12 h, 130 °C
Reference
N-Methylation of Amines with Methanol in Aqueous Solution Catalyzed by a Water-Soluble Metal-Ligand Bifunctional Dinuclear Iridium Catalyst
Meng, Chong; Liu, Peng; Nguyen, Thanh Tung; Han, Xingyou; Li, Feng, Journal of Organic Chemistry, 2020, 85(9), 5815-5824

Production Method 17

Reaction Conditions
1.1 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ;  1 - 2 h, 25 °C; 25 °C → 0 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  pH 7 - 8
Reference
Pd(II)/Ag(I)-Promoted One-Pot Synthesis of Cyclic Ureas from (Hetero)Aromatic Amines and Isocyanates
Youn, So Won; Kim, Yi Hyun, Organic Letters, 2016, 18(23), 6140-6143

Production Method 18

Reaction Conditions
1.1 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene Solvents: N-Methyl-2-pyrrolidone ;  12 min, 250 °C
Reference
Selective N-monomethylation of primary anilines with dimethyl carbonate in continuous flow
Seo, Hyowon; Bedard, Anne-Catherine; Chen, Willie P.; Hicklin, Robert W.; Alabugin, Alexander; et al, Tetrahedron, 2018, 74(25), 3124-3128

Production Method 19

Reaction Conditions
1.1 Reagents: Cesium carbonate Catalysts: Dimethylformamide ,  Iridium ;  24 h, 150 °C
Reference
Preparation and use of DMF-stabilized iridium nanoclusters as methylation catalysts using methanol as the C1 source
Oikawa, Kei; Itoh, Satoshi; Yano, Hiroki; Kawasaki, Hideya; Obora, Yasushi, Chemical Communications (Cambridge, 2017, 53(6), 1080-1083

Production Method 20

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide ,  Hydrogen Catalysts: 2322320-11-4 Solvents: Isopropanol ;  24 h, 25 atm, 50 °C
Reference
Catalytic Hydrogenation of Carboxamides with a Bifunctional Cp*Ru Catalyst Bearing an Imidazol-2-ylidene with a Protic Aminoethyl Side Chain
Kawano, Teruhiro; Watari, Ryo; Kayaki, Yoshihito ; Ikariya, Takao, Synthesis, 2019, 51(12), 2542-2547

Production Method 21

Reaction Conditions
1.1 3 h, 120 °C
Reference
Methylation of Aniline and Its Derivatives with Dimethyl Carbonate under the Action of Zeolite FeHY-mmm
Khusnutdinov, R. I.; Shchadneva, N. A.; Mayakova, Yu. Yu.; Abdrakhmanov, A. N.; Khazipova, A. N.; et al, Russian Journal of Organic Chemistry, 2019, 55(8), 1085-1087

Production Method 22

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide Catalysts: Iridium(1+), [1-[2-(2-benzoxazolyl-κN3)phenyl]-1,3-dihydro-3-methyl-2H-benzimida… ;  12 h, 130 °C
Reference
N-Methylation of ortho-substituted aromatic amines with methanol catalyzed by 2-arylbenzo[d]oxazole NHC-Ir(III) complexes
Huang, Shuang; Hong, Xi; Cui, He-Zhen; Zhou, Quan; Lin, Yue-Jian; et al, Dalton Transactions, 2019, 48(15), 5072-5082

Production Method 23

Reaction Conditions
1.1 Reagents: Hydrogen Catalysts: 2895434-86-1 Solvents: Tetrahydrofuran ;  5 min, 1 MPa; 48 h, 130 °C
Reference
Chemoselectivity change in catalytic hydrogenolysis enabling urea-reduction to formamide/amine over more reactive carbonyl compounds
Iwasaki, Takanori ; Tsuge, Kazuki; Naito, Naoki ; Nozaki, Kyoko, Nature Communications, 2023, 14(1),

Production Method 24

Reaction Conditions
1.1 Reagents: Hydrogen Catalysts: Potassium tert-butoxide ,  Manganese(1+), [N-[2-[bis(1-methylethyl)phosphino-κP]ethyl]-1-methyl-1H-imidazol… Solvents: Cyclohexane ;  16 h, 30 bar, 100 °C
Reference
Efficient and selective hydrogenation of amides to alcohols and amines using a well-defined manganese-PNN pincer complex
Papa, Veronica; Cabrero-Antonino, Jose R.; Alberico, Elisabetta; Spanneberg, Anke; Junge, Kathrin; et al, Chemical Science, 2017, 8(5), 3576-3585

Production Method 25

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide Catalysts: 2489429-36-7 ;  12 h, 130 °C
Reference
Bimetallic Bis-NHC-Ir(III) Complex Bearing 2-Arylbenzo[d]oxazolyl Ligand: Synthesis, Catalysis, and Bimetallic Effects
Huang, Shuang; Hong, Xi; Cui, He-Zhen; Zhan, Bing; Li, Zhi-Ming; et al, Organometallics, 2020, 39(19), 3514-3523

Production Method 26

Reaction Conditions
1.1 Reagents: Lithium tert-butoxide Catalysts: Di-μ-chlorodichlorobis[(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2,4-cyclopentadien-1-… ,  Bis[2-(diphenylphosphino)phenyl] ether ;  24 h, 100 °C
Reference
Efficient Ruthenium-Catalyzed N-Methylation of Amines Using Methanol
Dang, Tuan Thanh; Ramalingam, Balamurugan; Seayad, Abdul Majeed, ACS Catalysis, 2015, 5(7), 4082-4088

Production Method 27

Reaction Conditions
1.1 Reagents: Cesium carbonate Catalysts: Iridium, bromodicarbonyl[1-(1,1-dimethylethyl)-1,3-dihydro-3-[[6-(methoxymethyl)… Solvents: Methanol ;  rt; 5 h, 423 K
Reference
N-Methylation of Amines with Methanol Catalyzed by Iridium(I) Complexes Bearing an N,O-Functionalized NHC Ligand
Gonzalez-Lainez, Miguel; Jimenez, M. Victoria; Azpiroz, Ramon ; Passarelli, Vincenzo ; Modrego, F. Javier ; et al, Organometallics, 2022, 41(11), 1364-1380

Production Method 28

Reaction Conditions
1.1 Reagents: Sodium hydroxide Catalysts: Iridium, di-μ-chlorodichlorobis[(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2,4-cyclopen… Solvents: Methanol ;  12 h, 150 °C
Reference
General and efficient method for direct N-monomethylation of aromatic primary amines with methanol
Li, Feng; Xie, Jianjiang; Shan, Haixia; Sun, Chunlou; Chen, Lin, RSC Advances, 2012, 2(23), 8645-8652

Production Method 29

Reaction Conditions
1.1 Reagents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone ,  Sodium hydride Solvents: Dimethylformamide
Reference
The conversion of phenols to primary and secondary aromatic amines via a Smiles rearrangement
Coutts, Ian G. C.; Southcott, Mark R., Journal of the Chemical Society, 1990, (3), 767-71

Production Method 30

Reaction Conditions
1.1 Reagents: Hydrogen Catalysts: Copper ,  Aluminum copper (AlCu) Solvents: Methanol ;  60 min, 13 bar, 373 K
Reference
One-pot synthesis of N,N-dimethylanilines from nitroarenes with skeletal Cu as chemoselective catalyst
Rong, Zeming; Zhang, Wenjun; Zhang, Peng; Sun, Zhuohua; Lv, Jinkun; et al, Catalysis Communications, 2013, 41, 115-118

Production Method 31

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide Catalysts: Ruthenium trichloride Solvents: Methanol ;  24 h, 130 °C
Reference
Simple RuCl3-catalyzed N-Methylation of Amines and Transfer Hydrogenation of Nitroarenes using Methanol
Sarki, Naina; Goyal, Vishakha; Tyagi, Nitin Kumar; Puttaswamy; Narani, Anand; et al, ChemCatChem, 2021, 13(7), 1722-1729

Production Method 32

Reaction Conditions
1.1 Reagents: Potassium hydroxide Catalysts: Iridium(1+), chlorobis(1,3-dihydro-1,3-dimethyl-2H-imidazol-2-ylidene)[(1,2,3,4,… Solvents: Toluene ;  12 h, 100 °C
Reference
Effect of the ancillary ligand in N-heterocyclic carbene iridium(III) catalyzed N-alkylation of amines with alcohols
Feng, Xinshu; Huang, Ming, Polyhedron, 2021, 205,

Production Method 33

Reaction Conditions
1.1 Reagents: Sodium borohydride Solvents: 1,4-Dioxane ;  24 h, 100 °C
1.2 Reagents: Ammonium chloride Solvents: Water
Reference
CO2-tuned highly selective reduction of formamides to the corresponding methylamines
Guo, Zhiqiang; Pang, Tengfei; Yan, Leilei; Wei, Xuehong; Chao, Jianbin; et al, Green Chemistry, 2021, 23(19), 7534-7538

Production Method 34

Reaction Conditions
1.1 Solvents: Methanol ;  3 h, 70 °C; 70 °C → rt
1.2 Reagents: Potassium carbonate Catalysts: 2043953-31-5 Solvents: Methanol ;  18 h, 140 °C
Reference
Synthesis of N-methylated amines from acyl azides using methanol
Chakrabarti, Kaushik; Dutta, Kuheli; Kundu, Sabuj, Organic & Biomolecular Chemistry, 2020, 18(30), 5891-5896

Production Method 35

Reaction Conditions
1.1 Reagents: Trimethylamineborane ,  Sodium hydride Solvents: Dimethylformamide ;  1.5 h, 80 °C
1.2 Reagents: Ammonium chloride Solvents: Water
Reference
Selective N-monomethylation of primary anilines with the controllable installation of N-CH2D, N-CHD2, and N-CD3 units
Meng, Jing; Xia, Hui-Min; Xu, Ai-Qing; Wang, Yi-Feng; Wang, Zhijuan; et al, Organic & Biomolecular Chemistry, 2020, 18(26), 4922-4926

Production Method 36

Reaction Conditions
1.1 Catalysts: Copper oxide (Cu2O) Solvents: Water ;  12 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1 - 2, rt
Reference
Hydrogenation of C=N bonds on TiO2 surface: The effect of the Cu2O/TiO2 p-n heterojunction photocatalyst
Jiang, Jie; Ding, Yuqiang, Surfaces and Interfaces, 2023, 37,

Production Method 37

Reaction Conditions
1.1 Reagents: Cesium carbonate Catalysts: Ruthenium, aqua[[2,2′-bipyridine]-6,6′(1H,1′H)-dionato(2-)-κN1,κN1′][(1,2,3,4,5,… ;  15 h, 125 °C
Reference
N-Methylation of Amines with Methanol in the Presence of Carbonate Salt Catalyzed by a Metal-Ligand Bifunctional Ruthenium Catalyst [(p-cymene)Ru(2,2'-bpyO)(H2O)]
Liu, Peng; Tung, Nguyen Thanh; Xu, Xiangchao; Yang, Jiazhi; Li, Feng, Journal of Organic Chemistry, 2021, 86(3), 2621-2631

Production Method 38

Reaction Conditions
1.1 Reagents: Hydrochloric acid Solvents: Water ;  120 °C
Reference
Palladium-Catalyzed Oxidative Carbonylation of Aromatic C-H Bonds of N-Alkylanilines with CO and Alcohols for the Synthesis of o-Aminobenzoates
Chen, Ming; Ren, Zhi-Hui; Wang, Yao-Yu; Guan, Zheng-Hui, Journal of Organic Chemistry, 2015, 80(2), 1258-1263

Production Method 39

Reaction Conditions
1.1 Reagents: Oxygen Catalysts: Copper Solvents: Water ;  12 h, rt → 100 °C
Reference
A Facile and Practical Copper Powder-Catalyzed, Organic Solvent- and Ligand-Free Ullmann Amination of Aryl Halides
Jiao, Jiao; Zhang, Xi-Ru; Chang, Ning-Hui; Wang, Jie; Wei, Jun-Fa; et al, Journal of Organic Chemistry, 2011, 76(4), 1180-1183

Production Method 40

Reaction Conditions
1.1 Reagents: Ethylene carbonate Solvents: Methanol ;  28 h, 180 °C; 180 °C → rt
Reference
Sequential coupling of the transesterification of cyclic carbonates with the selective N-methylation of anilines catalyzed by faujasites
Selva, Maurizio; Perosa, Alvise; Fabris, Massimo, Green Chemistry, 2008, 10(10), 1068-1077

4-Chloro-N-methylaniline Raw materials

4-Chloro-N-methylaniline Preparation Products

Additional information on 4-Chloro-N-methylaniline

Recent Advances in the Study of 4-Chloro-N-methylaniline (CAS: 932-96-7) and Its Applications in Chemical Biology and Pharmaceutical Research

4-Chloro-N-methylaniline (CAS: 932-96-7) is an important intermediate in the synthesis of various pharmaceuticals and agrochemicals. Recent studies have highlighted its role in the development of novel therapeutic agents and its potential applications in chemical biology. This research brief aims to summarize the latest findings related to this compound, focusing on its synthesis, biological activity, and industrial relevance.

A study published in the Journal of Medicinal Chemistry (2023) explored the use of 4-Chloro-N-methylaniline as a precursor in the synthesis of kinase inhibitors. The researchers demonstrated that derivatives of this compound exhibit significant inhibitory activity against specific cancer-related kinases, suggesting its potential as a scaffold for anticancer drug development. The study utilized computational modeling and in vitro assays to validate the binding affinity and selectivity of these derivatives.

In another recent investigation, 4-Chloro-N-methylaniline was employed in the development of novel antimicrobial agents. A team from the University of Cambridge reported the synthesis of a series of sulfonamide derivatives incorporating this compound, which showed promising activity against drug-resistant bacterial strains. The findings, published in Antimicrobial Agents and Chemotherapy, underscore the versatility of 4-Chloro-N-methylaniline in addressing global health challenges.

From an industrial perspective, advancements in the green synthesis of 4-Chloro-N-methylaniline have been reported. A 2024 study in Green Chemistry detailed a catalytic process that reduces the environmental impact of its production, achieving higher yields with lower energy consumption. This development aligns with the growing demand for sustainable chemical manufacturing practices in the pharmaceutical industry.

The toxicological profile of 4-Chloro-N-methylaniline has also been recently reevaluated. New data from the European Chemicals Agency (ECHA) provides updated safety guidelines for handling this compound, particularly in industrial settings. These findings are crucial for ensuring workplace safety and regulatory compliance in facilities that manufacture or use this chemical.

Looking forward, researchers are exploring the potential of 4-Chloro-N-methylaniline in emerging areas such as targeted drug delivery systems and diagnostic agent development. Its chemical properties make it a valuable building block for creating more complex molecular architectures with specific biological functions. The compound's versatility continues to make it a subject of active investigation across multiple disciplines within chemical biology and pharmaceutical sciences.

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