- Investigation of NNN Pincer Ruthenium(II) Complexes with a Pendant Hydroxyl Group for N-Monomethylation of amines and Nitroarenes by MethanolLi, Kangkang; Li, Jin-Feng; Yin, Bing; Zeng, Fanlong, ChemCatChem, 2022, 14(11),
Cas no 932-96-7 (4-Chloro-N-methylaniline)
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
-
Symbol:
- Prompt:warning
- Signal Word:Danger
- Hazard Statement: H226-H302+H312+H332-H315-H319
- Warning Statement: P210-P233-P240-P241+P242+P243-P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P305+P351+P338+P337+P313-P403+P235-P501
- Hazardous Material transportation number:UN 1993 3/PG 3
- WGK Germany:3
- Hazard Category Code: 10-36/37
- Safety Instruction: S16-S26-S36/37/39
- RTECS:CX9857900
-
Hazardous Material Identification:
- HazardClass:6.1
- PackingGroup:III
- Safety Term:6.1
- Packing Group:III
- Risk Phrases:R10; R20/21/22; R36/37/38
- Storage Condition:Flammable area
4-Chloro-N-methylaniline Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| Fluorochem | 009650-1g |
4-Chloro-N-methylaniline |
932-96-7 | 97% | 1g |
£10.00 | 2022-02-28 | |
| Fluorochem | 009650-5g |
4-Chloro-N-methylaniline |
932-96-7 | 97% | 5g |
£20.00 | 2022-02-28 | |
| Fluorochem | 009650-25g |
4-Chloro-N-methylaniline |
932-96-7 | 97% | 25g |
£79.00 | 2022-02-28 | |
| SHANG HAI A LA DING SHENG HUA KE JI GU FEN Co., Ltd. | C139458-100g |
4-Chloro-N-methylaniline |
932-96-7 | ≥96% | 100g |
¥1927.90 | 2023-09-03 | |
| SHANG HAI A LA DING SHENG HUA KE JI GU FEN Co., Ltd. | C139458-25g |
4-Chloro-N-methylaniline |
932-96-7 | ≥96% | 25g |
¥568.90 | 2023-09-03 | |
| SHANG HAI A LA DING SHENG HUA KE JI GU FEN Co., Ltd. | C139458-5g |
4-Chloro-N-methylaniline |
932-96-7 | ≥96% | 5g |
¥142.90 | 2023-09-03 | |
| SHANG HAI A LA DING SHENG HUA KE JI GU FEN Co., Ltd. | C139458-1g |
4-Chloro-N-methylaniline |
932-96-7 | ≥96% | 1g |
¥48.90 | 2023-09-03 | |
| Chemenu | CM118284-25g |
4-Chloro-N-methylaniline |
932-96-7 | 95% | 25g |
$122 | 2021-06-17 | |
| SHANG HAI YI EN HUA XUE JI SHU Co., Ltd. | R032679-1g |
4-Chloro-N-methylaniline |
932-96-7 | 96% | 1g |
¥59 | 2024-05-20 | |
| SHANG HAI YI EN HUA XUE JI SHU Co., Ltd. | R032679-25g |
4-Chloro-N-methylaniline |
932-96-7 | 96% | 25g |
¥683 | 2024-05-20 |
4-Chloro-N-methylaniline Production Method
Production Method 1
Production Method 2
- Tandem Transformation of Nitro Compounds into N-Methylated Amines: Greener Strategy for the Utilization of Methanol as a Methylating AgentPaul, Bhaskar; Shee, Sujan; Chakrabarti, Kaushik; Kundu, Sabuj, ChemSusChem, 2017, 10(11), 2370-2374
Production Method 3
1.2 Reagents: Water ; rt
- La-Catalyzed Decarbonylation of Formamides and Its ApplicationsLi, Shaocheng; Rajeshkumar, Thayalan; Liu, Jincheng; Maron, Laurent ; Zhou, Xigeng, Organic Letters, 2023, 25(1), 163-168
Production Method 4
- Sustainable and Selective Monomethylation of Anilines by Methanol with Solid Molecular NHC-Ir CatalystsChen, Jiangbo; Wu, Jiajie; Tu, Tao, ACS Sustainable Chemistry & Engineering, 2017, 5(12), 11744-11751
Production Method 5
- Room-Temperature Copper-Catalyzed Arylation of Dimethylamine and Methylamine in Neat WaterWang, Deping; Kuang, Daizhi; Zhang, Fuxing; Yang, Chunlin; Zhu, Xiaoming, Advanced Synthesis & Catalysis, 2015, 357(4), 714-718
Production Method 6
- Highly efficient N-monomethylation of primary aryl aminesPeng, Yiyuan; Liu, Hanliang; Tang, Min; Cai, Lisheng; Pike, Victor, Chinese Journal of Chemistry, 2009, 27(7), 1339-1344
Production Method 7
- Microwave-assisted deformylation of N-aryl formamide by KF on basic Al2O3Ge, Yiyu; Hu, Longqin, Tetrahedron Letters, 2007, 48(26), 4585-4588
Production Method 8
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
- A facile protocol for the synthesis of mono-N-methyl anilines via formimidate intermediatesSun, Nan; Wang, Shuai; Mo, Weimin; Hu, Baoxiang; Shen, Zhenlu; et al, Tetrahedron, 2010, 66(35), 7142-7148
Production Method 9
- Microwave-assisted one-pot synthesis of N-alkyl aromatic amines from benzanilide in presence of phase transfer catalystTapase, Arvind B.; Shinde, Narayan; Shinde, Devanand, Organic Chemistry: An Indian Journal, 2010, 6(1), 52-55
Production Method 10
- Recyclable covalent triazine framework-supported iridium catalyst for the N-methylation of amines with methanol in the presence of carbonateLiu, Peng ; Yang, Jiazhi; Ai, Yao; Hao, Shushu; Chen, Xiaozhong; et al, Journal of Catalysis, 2021, 396, 281-290
Production Method 11
- Efficient and Versatile Catalytic Systems for the N -Methylation of Primary Amines with Methanol Catalyzed by N -Heterocyclic Carbene Complexes of IridiumToyooka, Genki; Tuji, Akiko; Fujita, Ken-ichi, Synthesis, 2018, 50(23), 4617-4626
Production Method 12
- Selective N-Monomethylation of Amines and Nitroarenes using Methanol over an Encapsulated Iridium NanocatalystFu, Aixiao; Liu, Qiang; Jiang, Mingxiang; Xu, Guoqiang, Asian Journal of Organic Chemistry, 2019, 8(4), 487-491
Production Method 13
- N-Methylation of amines with methanol catalyzed by a Cp*Ir complex bearing a functional 2,2'-bibenzimidazole ligandLiang, Ran; Li, Shun; Wang, Rongzhou; Lu, Lei; Li, Feng, Organic Letters, 2017, 19(21), 5790-5793
Production Method 14
- Ruthenium(II) Complexes of Heteroditopic N-Heterocyclic Carbene Ligands: Efficient Catalysts for C-N Bond Formation via a Hydrogen-Borrowing Strategy under Solvent-Free ConditionsDonthireddy, S. N. R.; Mathoor Illam, Praseetha; Rit, Arnab, Inorganic Chemistry, 2020, 59(3), 1835-1847
Production Method 15
- A highly active catalyst supported molecular sieves-NaHCO3 mixture for the selective and advantageous N-monoalkylation of aminesDas, Asish R.; Medda, Arunima; Singha, Raghunath; Guchhait, Nikhil, Journal of the Indian Chemical Society, 2009, 86(8), 841-848
Production Method 16
- N-Methylation of Amines with Methanol in Aqueous Solution Catalyzed by a Water-Soluble Metal-Ligand Bifunctional Dinuclear Iridium CatalystMeng, Chong; Liu, Peng; Nguyen, Thanh Tung; Han, Xingyou; Li, Feng, Journal of Organic Chemistry, 2020, 85(9), 5815-5824
Production Method 17
1.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7 - 8
- Pd(II)/Ag(I)-Promoted One-Pot Synthesis of Cyclic Ureas from (Hetero)Aromatic Amines and IsocyanatesYoun, So Won; Kim, Yi Hyun, Organic Letters, 2016, 18(23), 6140-6143
Production Method 18
- Selective N-monomethylation of primary anilines with dimethyl carbonate in continuous flowSeo, Hyowon; Bedard, Anne-Catherine; Chen, Willie P.; Hicklin, Robert W.; Alabugin, Alexander; et al, Tetrahedron, 2018, 74(25), 3124-3128
Production Method 19
- Preparation and use of DMF-stabilized iridium nanoclusters as methylation catalysts using methanol as the C1 sourceOikawa, Kei; Itoh, Satoshi; Yano, Hiroki; Kawasaki, Hideya; Obora, Yasushi, Chemical Communications (Cambridge, 2017, 53(6), 1080-1083
Production Method 20
- Catalytic Hydrogenation of Carboxamides with a Bifunctional Cp*Ru Catalyst Bearing an Imidazol-2-ylidene with a Protic Aminoethyl Side ChainKawano, Teruhiro; Watari, Ryo; Kayaki, Yoshihito ; Ikariya, Takao, Synthesis, 2019, 51(12), 2542-2547
Production Method 21
- Methylation of Aniline and Its Derivatives with Dimethyl Carbonate under the Action of Zeolite FeHY-mmmKhusnutdinov, 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
- N-Methylation of ortho-substituted aromatic amines with methanol catalyzed by 2-arylbenzo[d]oxazole NHC-Ir(III) complexesHuang, Shuang; Hong, Xi; Cui, He-Zhen; Zhou, Quan; Lin, Yue-Jian; et al, Dalton Transactions, 2019, 48(15), 5072-5082
Production Method 23
- Chemoselectivity change in catalytic hydrogenolysis enabling urea-reduction to formamide/amine over more reactive carbonyl compoundsIwasaki, Takanori ; Tsuge, Kazuki; Naito, Naoki ; Nozaki, Kyoko, Nature Communications, 2023, 14(1),
Production Method 24
- Efficient and selective hydrogenation of amides to alcohols and amines using a well-defined manganese-PNN pincer complexPapa, Veronica; Cabrero-Antonino, Jose R.; Alberico, Elisabetta; Spanneberg, Anke; Junge, Kathrin; et al, Chemical Science, 2017, 8(5), 3576-3585
Production Method 25
- Bimetallic Bis-NHC-Ir(III) Complex Bearing 2-Arylbenzo[d]oxazolyl Ligand: Synthesis, Catalysis, and Bimetallic EffectsHuang, Shuang; Hong, Xi; Cui, He-Zhen; Zhan, Bing; Li, Zhi-Ming; et al, Organometallics, 2020, 39(19), 3514-3523
Production Method 26
- Efficient Ruthenium-Catalyzed N-Methylation of Amines Using MethanolDang, Tuan Thanh; Ramalingam, Balamurugan; Seayad, Abdul Majeed, ACS Catalysis, 2015, 5(7), 4082-4088
Production Method 27
- N-Methylation of Amines with Methanol Catalyzed by Iridium(I) Complexes Bearing an N,O-Functionalized NHC LigandGonzalez-Lainez, Miguel; Jimenez, M. Victoria; Azpiroz, Ramon ; Passarelli, Vincenzo ; Modrego, F. Javier ; et al, Organometallics, 2022, 41(11), 1364-1380
Production Method 28
- General and efficient method for direct N-monomethylation of aromatic primary amines with methanolLi, Feng; Xie, Jianjiang; Shan, Haixia; Sun, Chunlou; Chen, Lin, RSC Advances, 2012, 2(23), 8645-8652
Production Method 29
- The conversion of phenols to primary and secondary aromatic amines via a Smiles rearrangementCoutts, Ian G. C.; Southcott, Mark R., Journal of the Chemical Society, 1990, (3), 767-71
Production Method 30
- One-pot synthesis of N,N-dimethylanilines from nitroarenes with skeletal Cu as chemoselective catalystRong, Zeming; Zhang, Wenjun; Zhang, Peng; Sun, Zhuohua; Lv, Jinkun; et al, Catalysis Communications, 2013, 41, 115-118
Production Method 31
- Simple RuCl3-catalyzed N-Methylation of Amines and Transfer Hydrogenation of Nitroarenes using MethanolSarki, Naina; Goyal, Vishakha; Tyagi, Nitin Kumar; Puttaswamy; Narani, Anand; et al, ChemCatChem, 2021, 13(7), 1722-1729
Production Method 32
- Effect of the ancillary ligand in N-heterocyclic carbene iridium(III) catalyzed N-alkylation of amines with alcoholsFeng, Xinshu; Huang, Ming, Polyhedron, 2021, 205,
Production Method 33
1.2 Reagents: Ammonium chloride Solvents: Water
- CO2-tuned highly selective reduction of formamides to the corresponding methylaminesGuo, Zhiqiang; Pang, Tengfei; Yan, Leilei; Wei, Xuehong; Chao, Jianbin; et al, Green Chemistry, 2021, 23(19), 7534-7538
Production Method 34
1.2 Reagents: Potassium carbonate Catalysts: 2043953-31-5 Solvents: Methanol ; 18 h, 140 °C
- Synthesis of N-methylated amines from acyl azides using methanolChakrabarti, Kaushik; Dutta, Kuheli; Kundu, Sabuj, Organic & Biomolecular Chemistry, 2020, 18(30), 5891-5896
Production Method 35
1.2 Reagents: Ammonium chloride Solvents: Water
- Selective N-monomethylation of primary anilines with the controllable installation of N-CH2D, N-CHD2, and N-CD3 unitsMeng, 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
1.2 Reagents: Hydrochloric acid Solvents: Water ; pH 1 - 2, rt
- Hydrogenation of C=N bonds on TiO2 surface: The effect of the Cu2O/TiO2 p-n heterojunction photocatalystJiang, Jie; Ding, Yuqiang, Surfaces and Interfaces, 2023, 37,
Production Method 37
- 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
- Palladium-Catalyzed Oxidative Carbonylation of Aromatic C-H Bonds of N-Alkylanilines with CO and Alcohols for the Synthesis of o-AminobenzoatesChen, Ming; Ren, Zhi-Hui; Wang, Yao-Yu; Guan, Zheng-Hui, Journal of Organic Chemistry, 2015, 80(2), 1258-1263
Production Method 39
- A Facile and Practical Copper Powder-Catalyzed, Organic Solvent- and Ligand-Free Ullmann Amination of Aryl HalidesJiao, 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
- Sequential coupling of the transesterification of cyclic carbonates with the selective N-methylation of anilines catalyzed by faujasitesSelva, Maurizio; Perosa, Alvise; Fabris, Massimo, Green Chemistry, 2008, 10(10), 1068-1077
4-Chloro-N-methylaniline Raw materials
- Methyl methanesulfonate
- Acetamide, N-(4-chlorophenyl)-N-methyl-
- 4'-Chloro-N-methylformanilide
- 4-Chlorobromobenzene
- Propanamide, 2-(4-chlorophenoxy)-N,2-dimethyl-
- Tert-butyl N-(4-chlorophenyl)-N-methylcarbamate
- 1-Chloro-4-iodobenzene
- Benzoyl azide, 4-chloro-
- Benzamide, N-(4-chlorophenyl)-N-methyl-
4-Chloro-N-methylaniline Preparation Products
4-Chloro-N-methylaniline Related Literature
-
Ziyang Deng,Changwei Chen,Sunliang Cui RSC Adv., 2016,6, 93753-93755
-
2. Fatty acid eutectic mixtures and derivatives from non-edible animal fat as phase change materials?Pau Gallart-Sirvent,Marc Martín,Gemma Villorbina,Mercè Balcells,Aran Solé,Luisa F. Cabeza,Ramon Canela-Garayoa RSC Adv., 2017,7, 24133-24139
-
Ross Harder,David C. Dunand,Ian McNulty Nanoscale, 2017,9, 5686-5693
-
Joo Chuan Yeo,Kenry Lab Chip, 2016,16, 4082-4090
-
Chao-Han Cheng,Wen-Zhen Wang,Shie-Ming Peng,I-Chia Chen Phys. Chem. Chem. Phys., 2017,19, 25471-25477
Related Categories
- Solvents and Organic Chemicals Organic Compounds Organic nitrogen compounds Organonitrogen compounds Aralkylamines
- Solvents and Organic Chemicals Organic Compounds Organic nitrogen compounds Organonitrogen compounds Amines Aralkylamines
- Solvents and Organic Chemicals Organic Compounds Amines/Sulfonamides
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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