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Cas Database

623-10-9

623-10-9

Identification

  • Product Name:4-(HYDROXYAMINO)TOLUENE

  • CAS Number: 623-10-9

  • EINECS:

  • Molecular Weight:123.155

  • Molecular Formula: C7H9NO

  • HS Code:

  • Mol File:623-10-9.mol

Synonyms:p-Tolylhydroxylamine;p-methylphenylhydroxylamine;4-Me-C6H4NHOH;Benzenamine,N-hydroxy-4-methyl;N-4-methylphenyl-hydroxylamine;N-p-Tolyhydroxylamine;Hydroxylamine,N-p-tolyl;p-Tolyhydroxylamine;4-methyl-N-phenyl hydroxylamine;Benzenamine, N-hydroxy-4-methyl-;4-Methylphenylhydroxylamine;

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 94 Articles be found

Generating System-Level Responses from a Network of Simple Synthetic Replicators

Sadownik, Jan W.,Kosikova, Tamara,Philp, Douglas

, p. 17565 - 17573 (2017)

The creation of reaction networks capable of exhibiting responses that are properties of entire systems represents a significant challenge for the chemical sciences. The system-level behavior of a reaction network is linked intrinsically to its topology and the functional connections between its nodes. A simple network of chemical reactions constructed from four reagents, in which each reagent reacts with exactly two others, can exhibit up-regulation of two products even when only a single chemical reaction is addressed catalytically. We implement a system with this topology using two maleimides and two nitrones of different sizes - either short or long and each bearing complementary recognition sites - that react pairwise through 1,3-dipolar cycloaddition reactions to create a network of four length-segregated replicating templates. Comprehensive 1H NMR spectroscopy experiments unravel the network topology, confirming that, in isolation, three out of four templates self-replicate, with the shortest template exhibiting the highest efficiency. The strongest template effects within the network are the mutually cross-catalytic relationships between the two templates of intermediate size. The network topology is such that the addition of different preformed templates as instructions to a mixture of all starting materials elicits system-level behavior. Instruction with a single template up-regulates the formation of two templates in a predictable manner. These results demonstrate that the rules governing system-level behavior can be unraveled through the application of wholly synthetic networks with well-defined chemistries and interactions.

Synthesis, crystal structure, theoretical study and application of 1-(4-methylphenyl)-3-(2- (trifluoromethyl)phenyl)triaz-1-ene 1-oxide in the extraction of Ni ions: Synthesis of a new triazene 1-oxide derivative, X-ray crystal structure and its theoretical studies

Rezaei, Behrooz,Fazlollahi, Mehrnoosh

, p. 1581 - 1590 (2021)

The crystal structure of 1-(4-methylphenyl)-3-(2-(trifluoromethyl)phenyl)triaz-1-ene 1-oxide (L) is monoclinic and has a space group of P21/c with a = 8.066(2) ?, b = 16.740(5) ?, c = 11.730(4) ?, β = 117.76(3)° and Z = 4. In this study, direct procedures were used to solve the crystalline structure of this complex and refine it by full-matrix least-squares to ultimate values of R1 = 0.0610 and wR2 = 0.1661 with 1474 reflections (I > 2σ(I)). The molecule is included in inter-hydrogen bonding with C5–H5 acting as donors and O atoms of N-oxide groups as acceptors (O1······H5) with a distance of 2.638 ?. These results were also confirmed by theoretical studies. The spectrophotometric titrations of the synthesized L with metal ions showed a substantially greater stability constant for its nickel ion complex with a mole ratio equal to 1. Consequently, the ligand was used for the selective extraction and spectrophotometric determining the Ni2+ ion in natural water. Under optimized conditions, the calibrating curve was linear over a nickel concentration range of 9.2 × 10?7–8.4 × 10?3 M. The detecting limit of this method was 6.0 × 10?7 M Ni2+. No considerable interference was found from at least 100 times concentrations of a number of possibly interfering ions.

Polystyrene stabilized iridium nanoparticles catalyzed chemo- and regio-selective semi-hydrogenation of nitroarenes to N-arylhydroxylamines

Bhattacherjee, Dhananjay,Das, Pralay,Kumar, Ajay,Shaifali,Zyryanov, Grigory V.

, (2021/08/31)

Polystyrene stabilized Iridium (Ir@PS) nanoparticles (NPs) as a heterogeneous catalyst have been developed and characterized by IR, UV–Vis, SEM, TEM, EDX and XRD studies. The prepared Ir@PS catalyst showed excellent reactivity for chemo- and regio-selective controlled-hydrogenation of functionalized nitroarenes to corresponding N-arylhydroxylamine using hydrazine hydrate as reducing source and environmentally benign polyethylene glycol (PEG-400) as green solvent. The present methodology was applied for vast substrate scope and found to be compatible with wide range of reducible functional groups. The reaction performed at 85 °C or ambient temperature and completed within 5–80 minutes. The catalyst can easily be filtered out from reaction mixture and reusable.

Electrochemically Tuned Oxidative [4+2] Annulation and Dioxygenation of Olefins with Hydroxamic Acids

Wei, Bang-Yi,Xie, Dong-Tai,Lai, Sheng-Qiang,Jiang, Yu,Fu, Hong,Wei, Dian,Han, Bing

supporting information, p. 3182 - 3188 (2020/12/11)

This work represents the first [4+2] annulation of hydroxamic acids with olefins for the synthesis of benzo[c][1,2]oxazines scaffold via anode-selective electrochemical oxidation. This protocol features mild conditions, is oxidant free, shows high regioselectivity and stereoselectivity, broad substrate scope of both alkenes and hydroxamic acids, and is compatible with terpenes, peptides, and steroids. Significantly, the dioxygenation of olefins employing hydroxamic acid is also successfully achieved by switching the anode material under the same reaction conditions. The study not only reveals a new reactivity of hydroxamic acids and its first application in electrosynthesis but also provides a successful example of anode material-tuned product selectivity.

Polyfunctionalized biaryls accessed by a one-pot nucleophilic aromatic substitution and sigmatropic rearrangement reaction cascade under mild conditions

Liang, Dong-Dong,Guo, Shen-Yi,Tong, Shuo,Wang, Mei-Xiang

supporting information, (2021/02/09)

A practical synthetic method has been developed for polyfunctionalized biaryls based on a facile one-pot nucleophilic aromatic substitution (SNAr) reaction and [5,5]- or [3,3]-sigmatropic rearrangement reaction cascade. Under mild basic conditions, N-arylhydroxylamines reacted with o-activated fluoro (het)arenes to form N,O-diarylhydroxylamine intermediates which underwent spontaneously selective [5,5]-sigmatropic rearrangement reaction to produce diverse functionalized 4-amino-4′-hydroxy-1,1′-biaryls. A sequential SNAr reaction and [3,3]-sigmatropic rearrangement took place between N-arylhydroxylamines and 2-fluoropyridine derivatives or 4-fluorobenzonitrile to afford functionalized 2-amino-2′-hydroxy-1,1′-biaryls. As invaluable and unique building blocks, the resulting biaryls were applied in the straightforward synthesis of N2,O2-coronarene, carbazole, aza- and diaza carbazole derivatives.

Practical bromination of arylhydroxylamines with SOBr2 towards ortho-bromo-anilides

Du, Yuanbo,Feng, Lei,Gao, Hongyin,Guo, Lirong,Lu, Haifeng,Xi, Zhenguo

supporting information, (2021/05/19)

A facile approach for synthesizing ortho-bromoanilides from readily available aryhydroxylamines and thionyl bromide is demonstrated in this work. Mild reaction conditions and broad scope of substrates ranging from heterocyclic structures to pharmaceutics-potential motifs are used in the reactions of this paper. Efficient bromination of ortho C–H bonds of the aryhydroxylamines has been achieved. Ortho-bromoanilide products were obtained in good to excellent yields, and model scaled-up reactions of this synthetic approach are shown in this work.

Process route upstream and downstream products

Process route

4-MeC<sub>6</sub>H<sub>4</sub>-N(Teoc)OTBS
1303610-37-8

4-MeC6H4-N(Teoc)OTBS

N-(4-methylphenyl)hydroxylamine
623-10-9

N-(4-methylphenyl)hydroxylamine

Conditions
Conditions Yield
With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 40 ℃; for 1.5h; Inert atmosphere;
83%
1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

N-(4-methylphenyl)hydroxylamine
623-10-9

N-(4-methylphenyl)hydroxylamine

Conditions
Conditions Yield
With 5% rhodium-on-charcoal; hydrazine hydrate; In tetrahydrofuran; at 0 ℃; for 2.5h; Inert atmosphere;
100%
With 5% rhodium-on-charcoal; hydrazine hydrate; In tetrahydrofuran; at 0 ℃; Inert atmosphere;
100%
With rhodium contaminated with carbon; hydrazine hydrate; In tetrahydrofuran; at 0 ℃; for 2.5h; Inert atmosphere;
100%
With hydrogen; reduced complex Pt(II)-polyethyleneimine; In water; at 30 ℃;
98%
With hydrogen; reduced complex Pt(II)-polyethyleneimine; In water; at 30 ℃;
98%
With ammonium formate; zinc; In acetonitrile; at 25 - 30 ℃; for 1.16667h; sonification;
96%
With hydrazine hydrate; at 60 ℃; for 0.833333h; chemoselective reaction; Green chemistry;
96%
With methyldiazene; In acetonitrile; at 28 ℃; for 1h; Irradiation; Sealed tube; Inert atmosphere;
96%
With carbon dioxide; zinc; In water; at 25 ℃; for 0.666667h; under 750.075 Torr; Sonication;
94%
With borane-ammonia complex; [C6H3-2,6-(CHN(t-Bu))2]Bi; In 1,4-dioxane; at 35 ℃; for 2h; Schlenk technique; Inert atmosphere;
94%
With sodium tetrahydroborate; palladium diacetate; In ethanol; dichloromethane; water; at 20 ℃; for 0.0833333h; Time;
90%
With hydrazine hydrate; at 85 ℃; for 0.5h;
90%
With tin(II) benzenethiolate; thiophenol; triethylamine; In benzene; for 0.166667h; Ambient temperature;
82%
With antimony; sodium tetrahydroborate; In methanol; for 1h; Ambient temperature;
73%
With bismuth(III) chloride; potassium borohydride; In ethanol; for 0.25h; Ambient temperature;
73%
With water; hydrazine hydrate; palladium on activated charcoal; In tetrahydrofuran; at 0 - 5 ℃; for 5h;
73%
With ammonium chloride; zinc; In ethanol; water; for 4h; Cooling with ice; Inert atmosphere;
68%
With ammonium chloride; zinc; at 0 - 10 ℃; for 2h;
67%
With 5% Rh/C; hydrazine hydrate; In tetrahydrofuran; at 0 - 25 ℃; for 2.5h;
67%
With rhodium contaminated with carbon; hydrazine hydrate; In tetrahydrofuran; at 0 - 20 ℃; for 3h;
67%
With sodium tetrahydroborate; tellurium; In ethanol; for 3h; Ambient temperature;
65%
With ammonium chloride; zinc;
58%
With sodium tetrahydroborate; selenium; In ethanol; at 23 - 26 ℃; for 6.5h;
54%
With hydrogen; iridium; In isopropyl alcohol; under 5250.4 Torr; Rate constant;
52%
With ammonium chloride; zinc; In ethanol; water; for 1h; from 20 deg C to 40 deg C;
48%
With ammonium chloride; zinc; In ethanol; water; at 20 ℃; for 0.25h;
25%
With Britton-Robbinson buffer; N-dodecylpyridinium chloride; In ethanol; at 25 ℃; Kinetics; Mechanism; electric current;
With Britton-Robbinson buffer; sodium dodecyl-sulfate; In ethanol; at 25 ℃; Kinetics; Mechanism; electric current;
With Britton-Robbinson buffer; Triton X-100; In ethanol; at 25 ℃; Kinetics; Mechanism; electric current;
In ethanol; at 25 ℃; Kinetics; Mechanism; polarographic reduction in the presence of ionic and non-ionic surfactants; pH = 7;
With ethanol; calcium chloride; zinc;
With ammonium salt; zinc;
With acetic acid; zinc; anschliessend Behandeln mit Wasser oder verd. wss. Schwefelsaeure;
With acetic acid; cadmium; anschliessend Behandeln mit Wasser oder verd. wss. Schwefelsaeure;
With lead; acetic acid; anschliessend Behandeln mit Wasser oder verd. wss. Schwefelsaeure;
With sodium amalgam; diethyl ether; anschliessend Behandeln mit Wasser oder verd. wss. Schwefelsaeure;
With sodium hydrogensulfide; water; calcium chloride; at 20 ℃; weiteres Reagens: Benzol;
With calcium chloride; zinc; unter Neutralisation mit Essigsaeure;
With ethanol; ammonia; anschl. Einleiten von Schwefelwasserstoff;
With ammonium chloride; zinc;
With hydrazine hydrate; Rh on carbon; In tetrahydrofuran;
With ammonium chloride; zinc; In water; at 60 - 65 ℃; for 0.25h;
With ammonium chloride; zinc; at 60 - 80 ℃;
With hydrazine hydrate; Raney nickel (type W-4); In ethanol; 1,2-dichloro-ethane; at 10 ℃;
With hydrazine hydrate; nickel;
With ammonium chloride; zinc;
With ammonium chloride; zinc; In ethanol; water; N,N-dimethyl-formamide; for 1h; Ambient temperature;
With ammonium chloride; zinc; In methanol; water; at 65 ℃;
With ammonium chloride; zinc; In ethanol; water; at 60 - 70 ℃;
In ethanol; at 25 ℃; polarographic reduction in the presence of ionic and non-ionic surfactants; pH = 7;
With ammonium chloride; zinc; In ethanol;
With ammonium chloride; zinc; In ethanol; for 3h; Yield given; Ambient temperature;
With water; ammonium chloride; zinc; In ethanol; at 70 ℃;
With hydrazine; Rh on carbon; In tetrahydrofuran;
With ammonium chloride; zinc; In ethanol; at 50 ℃;
With ammonium chloride; zinc; In methanol; water; at 0 ℃;
With sodium hydroxide; ammonium chloride; zinc; pH=6.5 - 7;
With ammonium chloride; zinc; In ethanol; at 50 - 70 ℃;
With ammonium chloride; zinc; In 2-methoxy-ethanol; for 3h;
With ammonium chloride; zinc; In chloroform; water; for 0.25h;
With ammonium chloride; zinc; In water; for 2h;
With carbon dioxide; water; zinc; at 25 ℃; for 1h; chemoselective reaction;
90 %Spectr.
With platinum on silica gel; hydrogen; dimethyl sulfoxide; N-butylamine; In isopropyl alcohol; at 20 ℃; for 3h; under 750.075 Torr; chemoselective reaction; Autoclave;
97 %Spectr.
With ammonium chloride; zinc; In water; at 65 ℃;
With ammonium chloride; zinc; at 50 - 60 ℃;
With hydrazine hydrate; In ethanol; at 0 ℃;
With ammonium chloride; zinc; In water; at 25 ℃; for 0.75h;
With ammonium chloride; zinc;
With ammonia borane; silver nitrate; In methanol; at 20 ℃; Sealed tube;
With ammonium chloride; zinc; In ethanol; water; at 65 ℃;
With ammonium chloride; zinc; In water; at 60 - 70 ℃; for 0.25h;
With rhodium contaminated with carbon; hydrazine hydrate; In tetrahydrofuran; at 0 ℃; Inert atmosphere;
With rhodium contaminated with carbon; hydrazine; In tetrahydrofuran; at 0 ℃; for 3h; Inert atmosphere;
With ethanol; calcium chloride; zinc;
With ammonium salt; zinc;
With 5% rhodium-on-charcoal; hydrazine hydrate; In tetrahydrofuran; at 0 - 20 ℃; for 5h; Inert atmosphere;
With 5% rhodium-on-charcoal; hydrazine hydrate; In tetrahydrofuran; at 0 ℃; for 2h; Inert atmosphere;
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; In dichloromethane; at 31 ℃; for 44h; Sealed tube; Irradiation;
With ammonium chloride; zinc; at 50 - 60 ℃;
With ammonium chloride; zinc; In ethanol; water; at 60 - 65 ℃; for 1h;
With 5% rhodium-on-charcoal; hydrazine hydrate; In tetrahydrofuran; at 0 - 20 ℃; for 5h; Inert atmosphere;
With ammonium chloride; zinc; In ethanol; water; at 20 - 50 ℃; for 2h;
With 5% rhodium-on-charcoal; hydrazine hydrate; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;
With 5% rhodium-on-charcoal; hydrazine hydrate; In tetrahydrofuran; at 0 - 20 ℃; for 3h;
benzene-petroleum ether

benzene-petroleum ether

1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

N-(4-methylphenyl)hydroxylamine
623-10-9

N-(4-methylphenyl)hydroxylamine

Conditions
Conditions Yield
With ammonium chloride; zinc; In water;
1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

N-(4-methylphenyl)hydroxylamine
623-10-9

N-(4-methylphenyl)hydroxylamine

1,2-bis(4-methylphenyl)diazene oxide
955-98-6,21650-69-1,71297-92-2

1,2-bis(4-methylphenyl)diazene oxide

Conditions
Conditions Yield
With sodium tetrahydroborate; palladium diacetate; In ethanol; water; at 20 ℃; for 0.166667h;
85%
10%
1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

N-(4-methylphenyl)hydroxylamine
623-10-9

N-(4-methylphenyl)hydroxylamine

1,2-bis(4-methylphenyl)diazene oxide
955-98-6,21650-69-1,71297-92-2

1,2-bis(4-methylphenyl)diazene oxide

Conditions
Conditions Yield
With [(5-phenyl-2,8-di-2-pyridinylanthyridine)Ru26-C6H6)2Cl2](PF6)2; hydrazine; In ethanol; at 80 ℃; for 10h;
52 %Spectr.
9 %Spectr.
35 %Spectr.
With methyldiazene; In acetonitrile; at 28 ℃; for 1h; Irradiation; Inert atmosphere;
71 %Spectr.
18 %Spectr.
11 %Spectr.
With methyldiazene; In methanol; at 28 ℃; for 1h; Solvent; Irradiation; Inert atmosphere;
62 %Spectr.
18 %Spectr.
15 %Spectr.
With [Co(κS,N-4-(trifluoromethyl)pyrimidine-2-thiolate)3]; methylhydrazine; In ethanol; at 70 ℃; for 5h; Reagent/catalyst; Temperature; Solvent; Catalytic behavior; Sealed tube;
13 %Spectr.
58 %Spectr.
8 %Spectr.
C-phenyl-N-p-tolyl-nitrone
19064-77-8

C-phenyl-N-p-tolyl-nitrone

cyanoacetic acid amide
107-91-5

cyanoacetic acid amide

2-cyano-3-phenylacrylamide
709-79-5

2-cyano-3-phenylacrylamide

N-(4-methylphenyl)hydroxylamine
623-10-9

N-(4-methylphenyl)hydroxylamine

Conditions
Conditions Yield
With sodium dodecyl-sulfate; In water; at 25 - 30 ℃; for 0.216667h;
83%
cinnamaldehyde-(<i>N</i>-<i>p</i>-tolyl oxime )
98203-62-4

cinnamaldehyde-(N-p-tolyl oxime )

malononitrile
109-77-3

malononitrile

(E)-2-(3-phenylallylidene)malononitrile
41109-96-0

(E)-2-(3-phenylallylidene)malononitrile

N-(4-methylphenyl)hydroxylamine
623-10-9

N-(4-methylphenyl)hydroxylamine

Conditions
Conditions Yield
With sodium dodecyl-sulfate; In water; at 25 - 30 ℃; for 0.25h;
83%
(Z)-2-phthalimido-1-p-tolyl-diazen-1-oxid
78661-62-8,78661-73-1,908352-82-9

(Z)-2-phthalimido-1-p-tolyl-diazen-1-oxid

N-(4-methylphenyl)hydroxylamine
623-10-9

N-(4-methylphenyl)hydroxylamine

Conditions
Conditions Yield
With hydrazine hydrate; at 5 ℃;
98%
1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

N-(4-methylphenyl)hydroxylamine
623-10-9

N-(4-methylphenyl)hydroxylamine

Conditions
Conditions Yield
With [Pd2(2,7-bis(2-pyridinyl)-1,8-naphthyridine)(μ-OH)(CF3CO2)2](CF3CO2); hydrogen; In methanol; at 25 ℃; for 6h; under 760.051 Torr;
17%
8%
In ethanol; water; at 25 ℃; Rate constant; Mechanism; Product distribution; polarographic reduction; potential-dependent rate constants kf,h, αna; pH = 1.81-11.00;
With hydrazine hydrate; In chloroform; for 1.25h; Overall yield = 87 %; Overall yield = 35.4 mg; chemoselective reaction;
1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

N-(4-methylphenyl)hydroxylamine
623-10-9

N-(4-methylphenyl)hydroxylamine

Conditions
Conditions Yield
With tert.-butylhydroperoxide; In acetonitrile; at 70 ℃; for 1h; Reagent/catalyst;
16 %Spectr.
75 %Spectr.

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