2835-99-6

Basic information

• Product Name: 4-Amino-m-cresol
• Synonyms: 4-amino-cresol;4-amino-m-creso;4-amino-m-cresol,4-hydroxy-o-toluidine,4-amino-3-methylphenol;m-Cresol, 4-amino-;Phenol, 4-amino-3-methyl-;p-Hydroxy-o-toluidine;4-Amino-3-methylphenol,98%;4-amino-meta-cresol
• CAS NO: 2835-99-6
• Molecular Formula: C₇H₉NO
• Molecular Weight: 123.15
• EINECS: 220-621-2
• Product Categories: Aromatic Phenols;NULL
• Mol File: 2835-99-6.mol
• Article Data: 28

Chemical Properties

• Melting Point: 176-179 °C(lit.)
• Boiling Point: 229.26°C (rough estimate)
• Flash Point: 127.2 °C
• Appearance: Brown/Powder
• Density: 1.0877 (rough estimate)
• Vapor Pressure: 1.65mmHg at 25°C
• Refractive Index: 1.5380 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: soluble in Methanol
• PKA: 10.34±0.18(Predicted)
• Water Solubility: insoluble
• BRN: 2078803
• CAS DataBase Reference: 4-Amino-m-cresol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-m-cresol(2835-99-6)
• EPA Substance Registry System: 4-Amino-m-cresol(2835-99-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 26-37/39-36/37/39-36-24/25
• RIDADR: UN3077
• WGK Germany: 3
• RTECS: GO6826000
• F: 8-10-23
• TSCA: Yes
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 2835-99-6(Hazardous Substances Data)

Usage

Description

4-Amino-3-methylphenol is a metabolite of 3-methyl-4-nitrophenol. It is a major metabolite of carcinogenic o-toluidine and causes DNA damage in the presence of Cu(II).

Chemical Properties

Light gray powder

Uses

Different sources of media describe the Uses of 2835-99-6 differently. You can refer to the following data:
1. 4-Amino-3-methylphenol is a useful reagent for the synthesis of piperidine (piperazine)-amide substituted derivatives as multi-target antipsychotics.4-Amino-3-methylphenol was used in synthesis of a new type of tweezer-molecule in which a strongly preferred binding conformation is generated by convergent, intramolecular hydrogen bonding.
2. 4-Amino-3-methylphenol was used in synthesis of a new type of tweezer-molecule in which a strongly preferred binding conformation is generated by convergent, intramolecular hydrogen bonding.

Application

4-Amino-m-cresol is used as an oxidative hair dye at a maximum concentration of 1.5% after mixing with peroxide.

Definition

ChEBI: A substituted aniline in which the aniline ring carries 4-hydroxy and 6-methyl substituents; a urinary metabolite of lidocaine.

General Description

4-Amino-3-methylphenol is a metabolite of 3-methyl-4-nitrophenol. It is a major metabolite of carcinogenic o-toluidine and causes DNA damage in the presence of Cu(II).

Flammability and Explosibility

Notclassified

Synthesis

The synthesis of 4-Amino-3-methylphenol is as follows:A mixture of the para-benzoquinone mono-oxime (1.26 mmol),SnCl2 (0.72 g, 3.80 mmol), 20 mL of CH2Cl2, and 0.2 mL of concentrated HCl, was heated to reflux for 16 h. The CH2Cl2 was removed under reduced pressure, and the residue was dissolved in ethyl acetate and washed with concentrated aqueous NaHCO3. The organic layer was dried over anhydrous Na2SO4 and the filtrate was concentrated under reduced pressure to afford the solid product.

Purification Methods

Crystallise it from 50% EtOH. [Beilstein 13 H 593, 13 IV 1698.]

InChI:InChI=1/C8H14O3/c1-5-6-10-7(9)11-8(2,3)4/h5H,1,6H2,2-4H3

Upstream product

• 88-72-2 1-methyl-2-nitrobenzene 
• 108-39-4 3-methyl-phenol 
• 611-22-3 N-(o-tolyl)hydroxylamine 
• 31656-92-5 1-azido-2-methyl-benzene 
• 7664-93-9 sulfuric acid 
• 7647-01-0 hydrogenchloride 
• 1435-88-7 3-Methyl-4-phenylazo-phenol 
• 7758-99-8 copper(II) sulfate 
• 95-53-4 o-toluidine 
• 13362-34-0 3-methyl-1,4-benzoquinone 4-oxime 
• 101816-75-5 1-(4-hydroxy-2-methyl-phenyl)-ethanone oxime 
• 13066-89-2 5-amino-2-hydroxy-4-methyl-benzoic acid 
• 2724-87-0 3-Methyl-4-(2-nitro-phenylazo)-phenol 
• 2581-34-2 3-methyl-4-nitrophenol 

Downstream Products

• 39495-15-3 4-acetamido-3-methylphenol 
• 145823-43-4 diacetyl-4-amino-3-methylphenol 
• 860571-35-3 chloro-acetic acid-(4-hydroxy-2-methyl-anilide) 
• 57556-30-6 4-hydroxy-2,N,N,N-tetramethyl-anilinium; iodide 
• 38519-39-0 4-benzothiazol-2-ylamino-3-methyl-phenol 
• 81418-77-1 4-Ethoxy-benzoic acid 4-(4-ethoxy-benzoylamino)-3-methyl-phenyl ester 
• 88854-46-0 C₂₂H₂₄N₄O₆ 
• 107834-30-0 1-(4-hydroxy-2-methylphenyl)-6-methyl-1,4-dihydro-4-oxonicotinic acid 
• 452-70-0 4-fluoro-3-methylphenol 
• 36174-07-9 N,O-diacetyl-5-hydroxy-1H-indazole 

Relevant articles and documents

New route for synthesis of fluorescent SnO2 nanoparticles for selective sensing of Fe(III) in aqueous media

A simple new route for synthesis of fluorescent SnO2 and its application as an efficient sensing material for Fe3+ in aqueous media is reported. The fluorescent SnO2 nanoparticles were obtained by oxidation of SnCl2, which when used as reducing agent for the reduction of organic nitro compounds to corresponding amino compounds in ethanol. The SnO2 nanoparticles have been characterized on the basis of powder-XRD, IR, UV-Vis, TEM, FESEM and EDX analysis and found that this material is highly fluorescent in aqueous media. Detail study revealed that this material functions as a selective probe for Fe3+ out of a large number of metal ions used. The oxygen vacancies (defects) generated on the surface of the SnO2 during synthesis, are the source of emission due to recombination of electrons with the photo-excited hole in the valance bond. The quenching of emission intensity in presence of Fe3+ is due to the nonradiative recombination of electrons and holes at the surface. This material is used for estimation of Fe3+ in real samples such as drinking water, tap water and soil.

A capping agent dissolution method for the synthesis of metal nanosponges and their catalytic activity towards nitroarene reduction under mild conditions

We report a general strategy for the synthesis of metal nanosponges (M = Ag, Au, Pt, Pd, and Cu) using a capping agent dissolution method where addition of water to the M@BNHx nanocomposite affords the metal nanosponges. The B-H bond of the BNHx polymer gets hydrolysed upon addition of water and produces hydrogen gas bubbles which act as dynamic templates leading to the formation of nanosponges. The rate of B-H bond hydrolysis has a direct impact on the final nanostructure of the materials. The metal nanosponges were characterized using powder XRD, electron microscopy, XPS, and BET surface area analyzer techniques. The porous structure of these nanosponges offers a large number of accessible surface sites for catalytic reactions. The catalytic activity of these metal nanosponges has been demonstrated for the reduction of 4-nitrophenol where palladium exhibits the highest catalytic activity (k = 0.314 min?1). The catalytic activity of palladium nanosponge was verified for the tandem dehydrogenation of ammonia borane and the hydrogenation of nitroarenes to arylamines in methanol at room temperature. The reduction of various substituted nitroarenes was proven to be functional group tolerant except for a few halogenated nitroarenes (X = Br and I) and >99% conversion was noted within 30-60 min with high turnover frequencies (TOF) at low catalyst loading (0.1 mol%). The catalyst could be easily separated out from the reaction mixture via centrifugation and was recyclable over several cycles, retaining its porous structure.

Monodispersed Ag nanoparticles as catalyst: Preparation based on crystalline supramolecular hybrid of decamethylcucurbit[5]uril and silver ions

Monodispersed silver nanoparticles (Ag0 NPs) have been first prepared on the basis of a postsynthesis via mild reduction from a new crystalline supramolecular hybrid solid assembled from Ag+ ions and decamethylcucurbit[5]uril (Me10CB[5]). Uniform growth of nearly spherical Ag0 NPs with an average size of ca. 4.4 nm was observed on the organic Me10CB[5] support to form Ag@Me10CB[5] composite material. The as-synthesized composite material was characterized by a range of physical measurements (PXRD, TGA, XPS, ICP, TEM, etc.) and was further exploited as a heterogeneous catalyst for the reduction of various nitrophenols in the presence of NaBH4. The kinetics of the reduction process was monitored under various experimental conditions. The Ag@Me10CB[5] composite material showed excellent catalytic performance over the reduction reactions and remained active after several consecutive cycles.