95-53-4 Usage
Uses
Used in Dye and Pigment Industry:
o-Toluidine is used as an intermediate for the manufacture of various dyes and pigments, particularly for printing textiles in blue-black colors. It plays a crucial role in the production of color photography and biological stains.
Used in Rubber Chemical Industry:
o-Toluidine serves as an intermediate in the production of rubber vulcanizing chemicals, which are essential for the manufacturing process of rubber products.
Used in Pharmaceutical Industry:
o-Toluidine is used as an intermediate in the synthesis of various pharmaceuticals, contributing to the development of essential medications.
Used in Pesticide Industry:
As an intermediate, o-Toluidine is utilized in the production of pesticides, helping to create effective solutions for pest control in agriculture and other industries.
Used in Organic Synthesis:
o-Toluidine is employed as an intermediate for organic synthesis, enabling the creation of various organic compounds for different applications.
Used in Clinical Laboratory:
o-Toluidine is used as a clinical laboratory reagent for glucose analysis, playing a significant role in the determination of glucose levels in biological materials.
Used in Synthesis of Poly(o-toluidine) and Copper Nanoparticle Composite Material:
o-Toluidine is used as a precursor in the synthesis of poly(o-toluidine) and copper nanoparticle composite material, which have potential applications in various fields.
Toluidine Isomers
Toluidine has three isomers: o-toluidine, m-toluidine and p-toluidine, while o-toluidine is the situ substitution product and m-toluidine is the shift substitution product.
O-toluidine is an important intermediate for the production of dyes and pigments and can be used to prepare direct red 62, red base RL, red base G, juvenile base GBC, alkaloid, peptone AS-D, acid red 35,158 265, solvent red 124, diazo group of azo dyes and coupling component, pigment yellow 14, yellow 17, Blue 19; raw materials of pesticide like Tricyclazole, insecticide Chlordimeform, chloromethiuron; acetochlor; raw materials of Thiofide; raw material of saccharin; corrosion inhibitor and other raw materials. In organic synthesis, o-toluidine are also used in synthesis of heterocyclic compounds indole and its derivatives.
Chemical and Physical Properties
O-toluidine is a clear colorless or light yellow liquid, may become reddish brown on exposure to air and light, and white precipitate at the presence of formaldehyde. It is slightly soluble in water, soluble in dilute acid, alcohol and ether.
relative density: 1.004(20℃);
melting point:-16.3℃ (β),-24.4℃(α);
boiling point: 199.7℃;
Flash point 185°F;
spontaneous ignition point: 482.2℃;
vapor density: 3.69.
Its vapor can form explosive mixture with air. The maximum allowable concentration in air is 5ppm. O-toluidine is flammable when exposed to heat or flame. It will, when heated, emit toxic gases toxic similar to that of aniline. Once it enters human body, it will cause the formation of hemoglobin, resulting in the occurrence of neurological disorders and cyanosis.
It has about the same density as water and is very slightly soluble in water. Vapors are heavier than air. Confirmed carcinogen.
The chemical properties of the toluidines are quite similar to those of aniline and toluidines have properties in common with other aromatic amines. Due to the amino group bonded to the aromatic ring, the toluidines are weakly basic.
Synthesis Method
o-Toluidine can be synthesized from toluene. The direct aromatic amination is very effective when done with a parent nitrenium ion, but o-toluidine can also be synthesized in other ways. For example, by the amination of toluene with methylhydroxylamine or hydroxylammonium salts in presence of aluminum trichloride.[22] The reaction using a nitrenium ion is not regionselective and multiple structural isomers will be present in the product. Figure 2 shows a very general synthesis reaction of o-toluidine and the other products (p-toluidine and m-toluidine). To obtain pure o-toluidine, the isomers need to be separated.
1. In the dilute acid medium, o-nitrotoluene heated together with iron powder and water to synthesize o-toluidine.
?
2. O-nitrotoluene is preheated with hydrogen in the induction heater and hydrogenated in the presence of copper catalyst to prepare o-toluidine.?
3.Toluene is aminated by ammonia sodium with the rhodium-carbon catalyst to produce o-toluidine.
4.Aniline is alkylated with methanol under the catalysis of ferric nitrate and germanium dioxide to produce the finished product o-toluidine.
Hazard Occasions
O-toluidine is toxic, the inhalation of its vapor or absorbtion through the skin or ingestion can cause poisoning. It is one of the known carcinogens.
O-toluidine is flammable with a fire point of 482℃, and can form explosive mixture with air. The allowable concentration in air in the United States is 2ppm (9mg/m3).
Toxicity
O-toluidine has a toxicity similar to aniline. The inhalation of its vapor or absorbtion through the skin or ingestion can cause poisoning. Once it enters human body, it will cause the formation of hemoglobin, resulting in the occurrence of neurological disorders, anoxia, headach, acratia, dizziness, drowsiness, cyanosis and hematuresis under microscope. Contact with eyes and skin may cause dermatitis and eye burns. It is one of the known carcinogens.
(Toxicity studies on animals: acute P.O. toxicity on rat LD50: 670 mg/kg, acute P.O. toxicity on mice LD50: 520 mg/kg
Skin irritation on rabbit 10 mg x 24 h, severe. Eye irritation on rabbit 0.75 mg x 24 h, severe.)
Transportation
Organic poison;
Dangerous Goods Code: 84182.UN No.：1708/6270/6.1-02/335.
Domestic commodity number: 61750；
Container in transportation must be marked “Poisonous”.
Storage
Stored in glass bottles or metal barrels to prevent mechanical damage. Place it in a cool, dry, well ventilated place. It is best to use the open or attached warehouse. No fireworks, far away from the fire site. Avoid light. Sealed preservation. Separate it from oxidizer.
Identification
Determination in air: analysis by silica adsorption, propyl alcohol treatment and gas chromatography.
Specific determination of glucose
o-Toluidine can also be used for measuring serum glucose concentration, in the form of acetic acid–o-toluidine.[26] The o-toluidine reaction for the estimation of glucose concentration in the serum gained massive popularity in the 1970s. This method was mostly used by clinical laboratories. Because of the potential health hazard, the laboratories now have a modified method by using alternative compounds.
Separation of toxic metal ions
The increasing level of heavy metals in the environment is a serious environmental problem. Various methods have been developed to remove these metals from aqueous systems, but these methods have limitations. Because of the limitations, researchers prompted to exploit inorganic materials as ion exchangers. These inorganic ion exchangers are able to obtain specific metal ions/anions or organic molecules. Following research in 2010,[27] there has been a synthesis and analytical application on a new thermally stable composite cation exchange material: poly-o-toluidine stannic molybdate. This material showed a high selectivity for Pb2+ and Hg2+ metal ions.
First-aid
If it enters the eyes, immediately rinse with water or eye drops; on the contact with the skin, immediately wash it off with soap and water; if it inhaled, immediately remove the patient from the scene to the fresh air; practice artificial respiration if necessary; if it is swallowed, drink plenty of water and induce vomiting followed by gastric lavage, and immediately send the patient to hospital for treatment. Methylene blue is a specific antidote to it.
Protective Measures
Suitable protective clothing should be equipped during the peration to prevent skin contact. Wear protective glasses to prevent contact with skin and eyes. Immediately remove permeable clothing, such as wetted or contaminated,. The operating site shall be provided with a safety signal indicator, eyewash and flushing equipment.
The Detection of blood glucose
Methods of determination of the glucose include oxidase method and o-toluidine condensation method and Folin-Wushi method. Among them, o-toluidine condensation method are most commonly used. This method has a high specificity for detecting glucose and is not affected by other substances other than glucose. The theoretical basis is that glucose in hot acetic acid solution can be condensed with o-toluidine to form a blue-green Schiff's base and the color depth is proportional to the glucose content. O-toluidine is added into the serum and glucose standard liquid. Then compare their optical density and calculate the serum glucose content. The normal level of fasting serum glucose is 70~100mg /dl.
Fire Extinguishant
Fog water, foam, carbon dioxide, sand.
Occupational Standard
TWA 22 mg/m3; STEL 44 mg/m3.
Production Methods
The production of O-toluidine is based on the catalytic hydrogenation of O-nitrotoluene or the amination of toluene with methylhydroxylamine in the presence of aluminum trichloride (Windholz 1983). It is available as a technical grade with a minimum of 99.5% purity containing m-toluidine (0.4% maximum) and/or ptoluidine (0.1% maximum) as impurities (Anon. 1978). The stabilized technical grade may also contain less than 0.5% of unidentified stabilizing agents to prevent darkening.
Synthesis Reference(s)
Journal of the American Chemical Society, 113, p. 1054, 1991 DOI: 10.1021/ja00003a056The Journal of Organic Chemistry, 43, p. 731, 1978 DOI: 10.1021/jo00398a046Chemical and Pharmaceutical Bulletin, 34, p. 3905, 1986 DOI: 10.1248/cpb.34.3905
Air & Water Reactions
Becomes reddish brown upon exposure to air and light [Hawley]. Slightly soluble in water.
Reactivity Profile
o-Toluidine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides. Emits very toxic oxides of nitrogen when heated to decomposition. Undergoes a hypergolic reaction with red fuming nitric acid [Kit and Evered, 1960, p. 239, 242].
Health Hazard
Exposures to O-toluidine cause toxicity and poisoning to animals and occupational workers. It is highly toxic to animals and humans and is rapidly absorbed by oral, dermal, and inhalation by mammals. The acute oral LD50 to rats ranges from 900 to 940 mg/kg. The compound is known to cause adverse effects in workers, which include headache, irritation of skin, eye, kidneys, bladder, and hematuria. O-Toluidine has caused hepatocellular adenoma and carcinoma in experimental laboratory mice and rats. Occupational workers exposed to O-toluidine have also demonstrated bladder cancer although the role of aniline cannot be ruled out. However, the IARC working group, because of insuffi cient data, classify O-toluidine as a Group 2B agent, meaning possibly carcinogenic to humans, while the NIOSH classify this compound as an occupational carcinogen, and the ACGIH label it as a suspected human carcinogen under A2 class.
Health Hazard
o-Toluidine is a cancer-causing compound.Its acute toxicity in test species was lowto moderate. Severe poisoning may occur athigh doses. It may enter the body by inhala tion of its vapors, ingestion, or absorptionthrough skin contact. The target organs arekidneys, liver, blood, cardiovascular system,skin, and eyes. The toxic symptoms includemethemoglobinemia, anemia, and reticulo cytosis, which are similar to aniline. Thisproduces anoxia (lack of oxygen), cyanosis,headache, weakness, drowsiness, dizziness,increase in urine volume, and hematuria.The pure liquid on skin contact can causeirritation and dermatitis. Contact with eyescan cause burns.LD50 value, oral (mice): 520 mg/kgo-Toluidine is a suspected human carcinogen. The evidence of carcinogenicity inhuman is inadequate. It caused tumors in thekidney, bladder, and lungs in rats, mice, andrabbits resulting from oral and subcutaneousadministration.Brennan and Schiestl (1999) have reportedo-toluidine and o-anisidine induced free radicals and intrachromosomal recombination inSaccharomyces cerevisiae. The toxicity andrecombination induced by these compoundswere reduced by free radical scavenger andantioxidant N-acetyl cysteine.
Health Hazard
Acute O-toluidine poisoning can cause painful hematuria (Goldbarb and Finelli, 1974) and methemoglobinemia (Hjelm et al 1972 and Struck et al 1969) in humans. Conflicting reports have resulted from evaluating the role of the compound in causing bladder or other cancers. Olt and Langner (1983) reported no increase in men engaged in the production of organic dyes, but Rubino et al (1982) strongly implicated O-toluidine in deaths due to bladder cancer in similar types of men.
Flammability and Explosibility
Nonflammable
Safety Profile
Confirmed carcinogen
with experimental neoplastigenic and
tumorigenic data. Poison by ingestion and
intraperitoneal routes. Moderately toxic by
skin contact. Human systemic effects by
inhalation: urine volume increase, hematuria,
and blood methemoglobinemiacarboxyhemoglobinemia.
An experimental
teratogen. Human mutation data reported. A
skin and severe eye irritant. Human mucous
membrane effects. Can produce severe
systemic disturbances. The main portal of
entry into the body is the respiratory tract,
particularly in cases of industrial exposure.
The symptoms produced are headache,
weakness, difficulty in breathing, air hunger,
psychic dsturbances, and marked irritation
of the kidneys and bladder. The literature
does not yield any good data for comparing
the toxicity of the o-, m-, and p-isomers.
Their behavior is generally comparable to
that of aniline. It has been determined
experimentally that a concentration of about
100 ppm is the maximum endurable for 1
hour without serious consequences and that
6-23 ppm is endurable for several hours
without serious disturbances.
Flammable when exposed to heat or
flame. Hypergolic reaction with red fuming
nitric acid. Can react with oxidizing
materials. To fight fire, use foam, CO2, dry
chemical. When heated to decomposition it
emits highly toxic fumes of NOx. See also
ANILINE.
Potential Exposure
o-Toluidine is used as an intermediate in the manufacture of dyes; as an intermediate in pharmaceutical manufacture; in textile printing; in rubber accelerators; in production of o-aminoazotoluene
Source
As o+p-toluidine, detected in distilled water-soluble fractions of 87 octane gasoline and
Gasohol at concentrations of 0.80 and 0.19 mg/L, respectively (Potter, 1996). o-Toluidine was
detected in 77% of 65 gasoline (regular and premium) samples (62 from Switzerland, 3 from
Boston, MA). At 25 °C, concentrations ranged from 13 to 18,000 μg/L in gasoline and 10 to 1,400 μg/L in water-soluble fractions. Average concentrations were 6.1 mg/L in gasoline and 0.47 mg/L
in water-soluble fractions (Schmidt et al., 2002).
Environmental fate
Biological. Heukelekian and Rand (1955) reported a 5-d BOD value of 1.40 g/g which is 55.1%
of the ThOD value of 2.54 g/g.
Chemical/Physical. Kanno et al. (1982) studied the aqueous reaction of o-toluidine and other
substituted aromatic hydrocarbons (aniline, toluidine, 1- and 2-naphthylamine, phenol, cresol,
pyrocatechol, resorcinol, hydroquinone, and 1-naphthol) with hypochlorous acid in the presence of
ammonium ion. They reported that the aromatic ring was not chlorinated as expected but was
cleaved by chloramine forming cyanogen chloride. As the pH was lowered, the amount of
cyanogen chloride formed increased (Kanno et al., 1982).
o-Toluidine will not hydrolyze because it does not contain a hydrolyzable functional group
(Kollig, 1993).
Metabolism
Absorption of O-toluidine from the gastrointestinal tract in rats is rapid with peak blood values at 1 h; blood values were near zero in 24 h (Sencyuk and Rucinska 1984a). The urine was the main excretory route; > 92% in 24 h (Cheever et al 1980). At an oral dose of 20 mg/kg, 26% was excreted in the urine in 24 h as O-toluidine (Senczuk and Rucinska 1984b). Kulkarni et al (1983) demonstrated that N-hydroxy-O-toluidine and O-nitrosotoluene are urinary metabolites of otoluidine. Other urinary metabolites in rats have included conjugated aminomethylphenols (Cheever et al 1980), azoxytoluene, N-acetyl-O-toluidine, N-acetyl-oaminobenzylalcohol, 4-amino-m-cresol, N-acetyl-4-amino-m-cresol, anthranilic acid, N-acetylanthranilic acid (Son et al 1980). Sulfate conjugates predominate over glucuronides by a ratio of 6:1. Thus, in rats, the major metabolic routes are N-acetylation and 4-hydroxylation. Human urinary metabolites (after administration of prilocaine) included O-toluidine,P-hydroxy-O-toluidine, and O-hydroxy-toluidine (Hjelm et al 1972). The primary metabolism of O-toluidine takes place in the endoplasmic reticulum. Exposure to O-toluidine enhances the microsomal activity of aryl hydrocarbon hydroxylase (particularly in kidney), NADPH-cyto-chrome c reductase and the content of cytochrome P-450 (Gnojkowski et al 1984).
Shipping
UN1708 Toluidines, liquid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
Purification Methods
In general, methods similar to those for purifying aniline can be used, e.g. distillation from zinc dust, at reduced pressure, under nitrogen. Berliner and May [J Am Chem Soc 49 1007 1927] purified it via the oxalate. Twice-distilled o-toluidine is dissolved in four times its volume of diethyl ether, and the equivalent amount of oxalic acid needed to form the dioxalate is added as its solution in diethyl ether. (If p-toluidine is present, its oxalate precipitates and can be removed by filtration.) Evaporation of the ethereal solution gives crystals of o-toluidine dioxalate [Beilstein 12 III 1494, 12 IV 1817]. These are filtered off, recrystallised five times from water containing a small amount of oxalic acid (to prevent hydrolysis), then treated with dilute aqueous Na2CO3 to liberate the amine which is separated, dried (CaCl2) and distilled under reduced pressure. The benzoyl derivative has m 144o (from EtOH). [Beilstein 12 H 772, 12 I 372, 12 II 429, 12 III 1837, 12 IV 1744.]
Check Digit Verification of cas no
The CAS Registry Mumber 95-53-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 5 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 95-53:
(4*9)+(3*5)+(2*5)+(1*3)=64
64 % 10 = 4
So 95-53-4 is a valid CAS Registry Number.
95-53-4Relevant articles and documents
Determination of prilocaine HCl in pharmaceutical preparations by GC-MS method
Atila, Alptug,Kadioglu, Yucel
, p. 6650 - 6654 (2014)
The novel analytical method using gas chromatography with mass spectrometry detection (GC-MS) method for determination of prilocaine HCl in pharmaceutical preparations were developed and validated. The using lidocaine HCl as the internal standard (IS) was
Rh-PVP Catalyzed Reductive Amination of Phenols by Ammonia or Amines to Cyclohexylamines under Solvent-free Conditions
Chaudhari, Chandan,Nagaoka, Katsutoshi,Nishida, Yoshihide,Rumi, Saeki,Sato, Katsutoshi,Shiraishi, Masaya
supporting information, p. 81 - 84 (2022/01/12)
Colloidal metal nanoparticles were examined for reductive amination of phenol by ammonia under mild reaction conditions. The results showed that Rh-PVP was the most active catalyst for reductive amination reaction. Linear, cyclic, and amino alcohols were used as nucleophiles and converted to primary/secondary/tertiary amines. Using this strategy, the synthesis of an industrially important chemical, N-cyclohexyl- 2-pyrrolidone was explored.
Palladium Immobilized on a Polyimide Covalent Organic Framework: An Efficient and Recyclable Heterogeneous Catalyst for the Suzuki–Miyaura Coupling Reaction and Nitroarene Reduction in Water
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An efficient and recyclable Pd nano-catalyst was developed via immobilization of Pd nanoparticles on polyimide linked covalent organic frameworks (PCOFs) that was facilely prepared through condensation of melamine and 3,3′,4,4′-biphenyltetracarboxylic dianhydride. The Pd nanoparticles (Pd NPs) catalyst was thoroughly characterized by FT-IR, XRD, SEM, TEM. Furthermore, the catalytic activity of Pd NPs catalyst was evaluated by Suzuki–Miyaura coupling reaction and nitroarene reduction in water, respectively. The excellent yields of corresponding products revealing revealed that the Pd NPs catalyst could be applied as an efficient and reusable heterogeneous catalyst for above two reactions. Graphical Abstract: [Figure not available: see fulltext.]
Industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles-catalyzed hydrogenation of nitroarenes
Fu, Lihua,Li, Dingzhong,Lu, Hao,Qiu, Renhua,Sun, Tulai,Xing, Chen,Yang, Tianbao
, (2022/01/11)
The development of green and efficient methods for hydrogenation of nitroarenes is still highly demanding in organic synthesis. Herein, we report an industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles process for the synthesis of aryl amines with good yields via hydrogenation of nitroarenes. Nine key anti-cancer drug intermediates were successfully achieved with protocol. And Osimertinib intermediate 4m can be smoothly synthesized at a 2.67 kg-scale with >99.5% HPLC purity. This protocol features cheap carbon source, highly catalytic activity, simple operation, kilogram-scalable and recyclable catalysts (eight times without observable losing activity).
Method for synthesizing heteroatom- substituted aromatic compound from styrene compound
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Paragraph 0185-0188, (2021/02/06)
The invention discloses a method for synthesizing a heteroatom-substituted aromatic compound from a styrene compound, which comprises the following steps of: mixing a styrene compound with a general formula (I) and a heteroatom-containing compound with a general formula (II), and reacting in the presence of an acid additive and an organic solvent to obtain a heteroatom-substituted compound with ageneral formula (III). According to the synthesis method disclosed by the invention, a large amount of styrene compounds are used as raw materials and react to generate aromatic amine or phenol compounds under the action of no metal catalysis; and compared with the traditional aromatic amine and phenol synthesis method, the method has the advantages of high yield, simple conditions, low waste discharge amount, no metal participation, simple reaction equipment, easiness in industrial production and the like.
Minimization of Back-Electron Transfer Enables the Elusive sp3 C?H Functionalization of Secondary Anilines
Zhao, Huaibo,Leonori, Daniele
supporting information, p. 7669 - 7674 (2021/03/08)
Anilines are some of the most used class of substrates for application in photoinduced electron transfer. N,N-Dialkyl-derivatives enable radical generation α to the N-atom by oxidation followed by deprotonation. This approach is however elusive to monosubstituted anilines owing to fast back-electron transfer (BET). Here we demonstrate that BET can be minimised by using photoredox catalysis in the presence of an exogenous alkylamine. This approach synergistically aids aniline SET oxidation and then accelerates the following deprotonation. In this way, the generation of α-anilinoalkyl radicals is now possible and these species can be used in a general sense to achieve divergent sp3 C?H functionalization.
Multi-functional aromatic amine compound as well as preparation method and application thereof
-
, (2021/08/14)
The invention belongs to the technical field of synthesis of aromatic amine compounds, and particularly relates to a multi-functional aromatic amine compound as well as a preparation method and application thereof. The invention provides a multi-functional aromatic amine compound and also provides a preparation method of the multi-functional aromatic amine compound. The amination reaction of aromatic carboxylic acid is catalyzed by DMAP at a relatively low temperature under the condition of no transition metal, and the method can be used for synthesizing a series of multi-functional aromatic amine compounds. The preparation method has not been reported in literature at present. The invention also provides a derivative product of arylamine and a preparation method thereof, and an application of the multi-functional aromatic amine compound in later modification of active molecules. The compound can be used for construction of optical active urea compounds and some important active molecules, and has a development prospect in synthesis of active drugs and natural products.
Ligand compound for copper catalyzed aryl halide coupling reaction, catalytic system and coupling reaction
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Paragraph 0111-0119, (2021/05/29)
The invention provides a ligand compound capable of being used for copper catalyzed aryl halide coupling reaction, the ligand compound is a three-class compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group, and the invention also provides a catalytic system for the aryl halide coupling reaction. Thecatalytic system comprises a copper catalyst, a compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group adopted as a ligand, alkali and a solvent, and meanwhile, the invention also provides a system for the aryl halide coupling reaction adopting the catalyst system. The compound containing the 2-(substituted or non-substituted) aminopyridine nitrogen oxygen group can be used as the ligand for the copper catalyzed aryl chloride coupling reaction, and the ligand is stable under a strong alkaline condition and can well maintain catalytic activity when being used for the copper-catalyzed aryl chloride coupling reaction. In addition, the copper catalyst adopting the compound as the ligand can particularly effectively promote coupling of copper catalyzed aryl chloride and various nucleophilic reagents which are difficult to generate under conventional conditions, C-N, C-O and C-S bonds are generated, and numerous useful small molecule compounds are synthesized. Therefore, the aryl halide coupling reaction has a very good large-scale application prospect by adopting the copper catalysis system of the ligand.
Magnetically‐recoverable Schiff base complex of Pd(II) immobilized on Fe3O4@SiO2 nanoparticles: an efficient catalyst for the reduction of aromatic nitro compounds to aniline derivatives
Azadi, Sedigheh,Esmaeilpour, Mohsen,Sardarian, Ali Reza
, p. 809 - 821 (2021/07/20)
Fe3O4@SiO2/Schiff base/Pd(II) is reported as a magnetically recoverable heterogeneous catalyst for the chemoselective reduction of aromatic nitro compounds to the corresponding amines through catalytic transfer hydrogenation (CTH). In this regard, a small amount of the nanocatalyst (0.52?mol% Pd) and hydrazine hydrate, showing safe characteristics and perfect ability as the hydrogen donor, were added to the nitro substrates. The experiments described the successful reduction of aromatic nitro compounds with good to excellent yields and short reaction times. The catalyst, due to its magnetic property, could be simply separated from the reaction mixture by a permanent magnet and reused in seven consecutive reactions without considerable loss in its activity. Moreover, the leaching of Pd was only 3.6% after the seventh run. Thus, the most striking feature of this method is to use a small amount of the magnetic nanocatalyst along with a cheap and safe hydrogen source to produce the important amine substances selectively, which makes the method economical, cheap, environmentally friendly, and simple. Graphic abstract: [Figure not available: see fulltext.]
Synthetic method of chlorantraniliprole pesticide intermediate 2 - amino -5 - chlorine - N and 3 -dimethylbenzamide
-
Paragraph 0021-0023, (2021/10/05)
The invention relates to a synthetic method of a chlorantraniliprole pesticide intermediate 2 - amino -5 - chlorine - N and 3 -dimethylbenzamide. Chloro, formylation gave 2 - amino -5 - chloro - N, 3 - dimethyl. The method has the advantages of simple reaction, low cost and high yield, and is a method suitable for industrial production.
