Production Method 1

89-60-1

106347-49-3

Reaction Conditions

1.1 Reagents: Acetic anhydride ,  Trifluoroacetic anhydride ,  Nitric acid
1.2 Reagents: Ammonium hydroxide Solvents: Water

Reference

ipso Nitration. XXVIII. Nitration of 4-substituted toluenes: 1,2 adducts

Fischer, Alfred; Fyles, Deborah L.; Henderson, George N.; Mahasay, Sumit Ray, Canadian Journal of Chemistry, 1986, 64(9), 1764-70

Production Method 2

89-60-1

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Water ;  1.5 h, 80 - 90 °C; 90 °C → 50 °C
1.2 Reagents: Cuprous chloride ;  2.5 h, 50 °C
1.3 Reagents: Sodium nitrite Solvents: Water ;  50 °C; 70 °C

Reference

Synthesis of 4-chloro-3-fluorotoluene and 4-bromo-3-fluorotoluene

Zhao, Haoyu; Xue, Xuming; Jiang, Tao, Jingxi Shiyou Huagong, 2007, 24(1), 39-43

Production Method 3

27329-27-7

89-60-1

Reaction Conditions

1.1 Reagents: Sodium chloride ,  Oxygen Catalysts: Cupric acetate ,  2,9-Dimethyl-1,10-phenanthroline ,  Silver sulfate Solvents: Dimethyl sulfoxide ;  20 h, 1 atm, 160 °C

Reference

Inexpensive NaX (X = I, Br, Cl) as a halogen donor in the practical Ag/Cu-mediated decarboxylative halogenation of aryl carboxylic acids under aerobic conditions

Fu, Zhengjiang; Jiang, Ligao; Zuo, Qianming; Li, Zhaojie; Liu, Yanzhu; et al, Organic & Biomolecular Chemistry, 2018, 16(30), 5416-5421

Production Method 4

27329-27-7

89-60-1

Reaction Conditions

1.1 Reagents: Cuprous chloride ,  Oxygen Catalysts: Cuprous iodide Solvents: Dimethyl sulfoxide ;  30 h, 160 °C

Reference

Halogenation and Cyanation of Electron-Deficient Aryl Carboxylic Acids via Cu Mediator as Well as Electron-Rich Ones through Pd Catalyst under Aerobic Conditions

Fu, Zhengjiang; Li, Zhaojie; Song, Yuanyuan; Yang, Ruchun; Liu, Yanzhu; et al, Journal of Organic Chemistry, 2016, 81(7), 2794-2803

Production Method 5

89-60-1

Reaction Conditions

1.1 Reagents: Sulfuric acid ,  Nitric acid

Reference

Alkaline Soil Degradation and Crop Safety of 5-Substituted Chlorsulfuron Derivatives

Wu, Lei ; Hua, Xue-Wen; Li, Yong-Hong; Wang, Zhong-Wen; Zhou, Sha; et al, Molecules, 2022, 27(10),

Production Method 6

89-60-1

Reaction Conditions

1.1 Reagents: Cuprous chloride ,  Nitrous acid

Reference

Synthesis of some nitrotoluenesulfonic acids

Asakura, Hideyuki; Muramoto, Yoshihiro, Nippon Kagaku Kaishi, 1977, (11), 1694-7

Production Method 7

89-60-1

Reaction Conditions

1.1 Reagents: Urea ,  Nitric acid Solvents: Acetic anhydride

Reference

Nitration of p-chlorotoluene and p-chloroisopropylbenzene

Khan, Iftikhar A.; Manglik, Ajay K.; Sangal, S. K., Journal of the Indian Chemical Society, 1988, 65(6), 415-16

Production Method 8

89-60-1

Reaction Conditions

1.1 Reagents: Sulfuric acid ,  Nitric acid ,  Water

Reference

Preparation of 4-halomononitrotoluenes

, Japan, , ,

Production Method 9

2088335-80-0

89-60-1

Reaction Conditions

1.1 Reagents: Potassium carbonate ,  Cupric chloride ,  Oxygen ,  Silver oxide (Ag2O) Catalysts: 1,10-Phenanthroline Solvents: Dimethyl sulfoxide ;  18 - 36 h, 0.5 MPa, 140 °C

Reference

Dehydroxyalkylative halogenation of C(aryl)-C bonds of aryl alcohols

Liu, Mingyang; Zhang, Zhanrong; Liu, Huizhen; Wu, Tianbin; Han, Buxing, Chemical Communications (Cambridge, 2020, 56(52), 7120-7123

Production Method 10

89-60-1

Reaction Conditions

1.1 Reagents: tert-Butyl nitrite Solvents: Acetonitrile ;  1 min, rt
1.2 Reagents: Cupric chloride Solvents: Acetonitrile ,  Ethylene glycol ;  4 min, 82 °C

Reference

Efficient Transposition of the Sandmeyer Reaction from Batch to Continuous Process

D'Attoma, Joseph; Camara, Titi; Brun, Pierre Louis; Robin, Yves; Bostyn, Stephane; et al, Organic Process Research & Development, 2017, 21(1), 44-51

Production Method 11

37777-68-7

89-60-1

Reaction Conditions

1.1 Solvents: Methanol ,  Water ;  240 s, rt

Reference

Improved Photodecarboxylation Properties in Zinc Photocages Constructed Using m-Nitrophenylacetic Acid Variants

Shigemoto, Austin K.; Bhattacharjee, Avik; Hickey, Erin E.; Boyd, Hallee Jade; McCormick, Theresa M.; et al, ChemPhotoChem, 2022, 6(9),

Production Method 12

89-60-1

Reaction Conditions

1.1 Reagents: Dichlorotriphenylphosphorane Solvents: Carbon tetrachloride
1.2 120 - 140 °C

Reference

Triphenylphosphine Dichloride

Dormoy, Jean-Robert; Castro, Bertrand, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, ,

Production Method 13

55912-20-4

89-60-1

Reaction Conditions

1.1 Solvents: Nitromethane

Reference

Development of Polymer-Supported Benzotriazole as a Novel Traceless Linker for Solid-Phase Organic Synthesis

Schiemann, Kai; Showalter, H. D. Hollis, Journal of Organic Chemistry, 1999, 64(13), 4972-4975

Production Method 14

89-60-1

Reaction Conditions

1.1 Reagents: Sodium nitrite ,  Hydrochloric acid ,  Cuprous chloride

Reference

Synthesis of 4-halotoluene-2- and 3-sulfonic acids, and sulfonation mixtures of 4-halotoluenes by the HPLC (high performance liquid chromatography) analysis

Muramoto, Yoshirio; Asakura, Hideyuki; Suzuki, Hitomi, Kinki Daigaku Kogakubu Kenkyu Hokoku, 1991, 25, 73-9

Production Method 15

89-60-1

Reaction Conditions

1.1 Reagents: Cupric chloride Catalysts: 2-Methyl-2-nitropropane

Reference

Alkyl nitrite-metal halide deamination reactions. 2. Substitutive deamination of arylamines by alkyl nitrites and copper(II) halides. A direct and remarkably efficient conversion of arylamines to aryl halides

Doyle, Michael P.; Siegfried, Bernard; Dellaria, Joseph F. Jr., Journal of Organic Chemistry, 1977, 42(14), 2426-31

4-Chloro-3-nitrotoluene Raw materials

• 4-Methyl-2-nitrobenzoic acid
• 4-Chloro-3-nitrophenylacetic acid
• 4-Chloro-3-nitrobenzyl alcohol
• Benzenemethanol, α,4-dimethyl-2-nitro-

4-Chloro-3-nitrotoluene Preparation Products

• 4-Chloro-3-nitrotoluene (89-60-1)
• 2,4-Cyclohexadien-1-ol, 3-chloro-6-methyl-6-nitro-, acetate (ester), cis- (106347-49-3)

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Comprehensive Overview of 4-Chloro-3-nitrotoluene (CAS No. 89-60-1): Properties, Applications, and Industry Insights

4-Chloro-3-nitrotoluene (CAS No. 89-60-1) is a versatile organic compound widely utilized in industrial and research applications. This yellow crystalline solid belongs to the nitrotoluene family, characterized by its molecular formula C7H6ClNO2. Its unique chemical structure, featuring a chloro group at the 4-position and a nitro group at the 3-position of the toluene ring, grants it distinct reactivity and functional value. Researchers often search for "synthesis of 4-Chloro-3-nitrotoluene" or "89-60-1 solubility data," reflecting its technical relevance.

The compound's physicochemical properties are critical for its applications. With a melting point of 44-46°C and moderate solubility in organic solvents like ethanol and acetone, it serves as a key intermediate in dye manufacturing and agrochemical production. Recent trends highlight growing interest in "eco-friendly nitrotoluene derivatives," aligning with sustainability goals. Innovations in catalytic reduction methods for 4-Chloro-3-nitrotoluene are also gaining traction, addressing demands for greener chemistry.

In the pharmaceutical sector, 89-60-1 is explored as a precursor for active pharmaceutical ingredients (APIs). Queries such as "4-Chloro-3-nitrotoluene drug intermediates" underscore its role in medicinal chemistry. Its electron-withdrawing groups facilitate electrophilic substitution reactions, making it valuable for constructing complex molecular frameworks. However, handling requires adherence to industrial safety standards, a topic frequently searched alongside "nitrotoluene handling precautions."

The compound's stability under controlled conditions enables its use in high-performance material synthesis. For instance, it contributes to polyurethane catalysts and corrosion inhibitors. Emerging discussions on "bio-based alternatives to nitrotoluenes" reflect shifting market priorities. Analytical techniques like HPLC and GC-MS are commonly employed for purity assessment, as noted in searches for "89-60-1 analytical methods."

Regulatory compliance remains a focal point. While 4-Chloro-3-nitrotoluene is not classified as hazardous under standard protocols, proper storage guidelines (e.g., avoiding light and moisture) are emphasized. Environmental concerns drive queries like "biodegradation of nitrotoluene compounds," prompting research into microbial degradation pathways. Industry reports suggest a steady demand for this compound, particularly in regions with robust specialty chemical sectors.

Future prospects for CAS No. 89-60-1 include advancements in catalytic hydrogenation to minimize waste. The rise of digital chemistry platforms has also streamlined its supply chain, with searches for "buy 4-Chloro-3-nitrotoluene online" increasing. Collaborative efforts between academia and industry aim to optimize its applications while addressing carbon footprint concerns, a hot topic in modern chemical engineering.

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