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

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

Uses

Used in Pharmaceutical Industry:
4-Amino-m-cresol is used as a reagent for the synthesis of piperidine (piperazine)-amide substituted derivatives, which serve as multi-target antipsychotics. It plays a crucial role in the development of new psychiatric medications.
Used in Chemical Research:
4-Amino-m-cresol is utilized in the synthesis of a new type of tweezer-molecule, where a strongly preferred binding conformation is generated by convergent, intramolecular hydrogen bonding. This application is significant in the field of molecular chemistry and material science.
Used in Cosmetic Industry:
In the cosmetic industry, 4-Amino-m-cresol is used as an oxidative hair dye. It is mixed with peroxide and can be used at a maximum concentration of 1.5% to achieve the desired hair color. This application takes advantage of its chemical properties to provide a lasting color effect.

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

• 2581-34-2 3-methyl-4-nitrophenol 
• 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 
• 13066-89-2 5-amino-2-hydroxy-4-methyl-benzoic acid 
• 101816-75-5 1-(4-hydroxy-2-methyl-phenyl)-ethanone oxime 
• 13362-34-0 3-methyl-1,4-benzoquinone 4-oxime 
• 95-53-4 o-toluidine 
• 343786-85-6 4-Acetoxyacet-o-toluidid 

Downstream Products

• 100868-09-5 N-(4-hydroxy-2-methyl-phenyl)-N'-(3-nitro-phenyl)-urea 
• 4370-76-7 methyl-[1,4]benzoquinone-1-imine 
• 133921-27-4 4-iodo-3-methyl-phenol 
• 108981-59-5 1-(4-Hydroxy-2-methyl-phenylazo)-[2]naphthol 
• 64050-09-5 4-dimethylcarbamoyloxy-2,N,N,N-tetramethyl-anilinium; iodide 
• 553-97-9 2-Methyl-1,4-benzoquinone 
• 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) 
• 51767-42-1 N-phenylsulfonyl-3-methyl-4-aminophenol 
• 57556-30-6 4-hydroxy-2,N,N,N-tetramethyl-anilinium; iodide 
• 38519-39-0 4-benzothiazol-2-ylamino-3-methyl-phenol 
• 72600-07-8 C₁₁H₁₅NOS 
• 81418-77-1 4-Ethoxy-benzoic acid 4-(4-ethoxy-benzoylamino)-3-methyl-phenyl ester 

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.

Hydroxylation of aromatic amines with dioxygen in photooxidation sensitized by substituted phthalocyanines

Photooxidation of aniline and its methyl and chloro derivatives with dioxygen sensitized by substituted zinc (PcZn) and palladium (PcPd) phthalocyanines in solution and on the carrier surface upon visible light irradiation affords selectively the corresponding p-aminophenols. Active and the most stable PcPd derivative adsorbed on Amberlite XAD 7HP provides conversion of 2,6-dimethylaniline with selectivity over 90% without the loss of sensitizer activity at least in 8 repeated cycles, the overall turnover number of the sensitizer being greater than 25,000.

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.

The Diels-Alder reactions of para-benzoquinone nitrogen-derivatives: An experimental and theoretical study

An experimental and theoretical study of the comparative reactivity and selectivity of the Diels-Alder reactions of para-benzoquinones and three nitrogen derivatives have been performed. The mono-oximes derivatives do not react under the tested reaction conditions, whereas the tosylated mono-oximes react slowly. However, the mono N-tosyl imines show excellent reactivity, and superior to the parent parabenzoquinones. DFT calculations support these experimental results.

COMPOUNDS AND METHODS FOR MODULATING ACTIVITY OF CALCIUM RELEASE CHANNELS

The present teachings provide compounds of Formulae I and II: and and pharmaceutically acceptable salts, hydrates, complexes, esters, and prodrugs thereof, wherein R1, R1', R2, R2', R3, R3', and X are as defined herein. The present teachings also provide methods of making the compounds of formulae I and II, and methods of treating RyR-associated conditions, disorders, and diseases that include administering a therapeutically effective amount of a compound of formula I or II to a subject in need thereof. In addition, the present teachings relate to methods of reducing the open probability of a ryanodine receptor, and methods of reducing Ca2+ release across a ryanodine receptor (e.g., into the cytoplasm of a cell), by contacting a compound of formula I or II with a ryanodine receptor.

1,3-Dihydroxybenzene derivatives and colorants containing said compounds

1,3-Dihydroxybenzene derivatives of general formula (I) or (Ia) or physiologically tolerated, water-soluble thereof wherein R′1 denotes substituted pyridyl group, a pyrimidyl group, a group of formula (IIa) or (IIIa) and the dyeing agents for keratin fibers containing these compounds.

One step hair coloring compositions using salts

A hair coloring composition comprising the following two compositions which are mixed just prior to application to the hair: (a) a composition comprising a water-soluble peroxygen oxidizing agent; and (b) a composition comprising one or more oxidative hair coloring agents selected from the group consisting of an aromatic diamine, an amino phenol, a naphthol, a polyhydric phenol, a catechol and mixtures thereof; wherein the composition comprising one or more oxidative hair coloring agents further comprises al least one water soluble carbonate releasing salts; and optionally a water soluble ammonium salt, is described.

Bisacetamide hydrochloride: A chemoselective and inexpensive N-acetylating reagent for aminophenols

A facile and chemoselective acetylation of aminophenols using bisacetamide hydrochloride under conventional heating and microwave irradiation has been developed. Also, a rapid method for the microwave-assisted preparation of aminophenols is described herein.

Transition metal complexes as dye forming catalysts in hair coloring compositions

A hair coloring composition comprising a first composition which comprises: (a) a dye forming transition metal salt or complex; which is first applied to the hair; and a second composition which comprises the following two compositions which are mixed just prior to application to the hair: (a) a composition comprising a water-soluble peroxygen oxidizing agent; and (b) a composition comprising one or more oxidative hair coloring agents selected from the group consisting of an aromatic diamine, an aminophenol, a polyhydric phenol a catechol and mixtures thereof.