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106-49-0 Usage

Chemical Description

p-toluidine and phenylhydrazine are primary aromatic amines used in the transamination reaction.

Chemical Properties

Different sources of media describe the Chemical Properties of 106-49-0 differently. You can refer to the following data:
1. White lustrous plates or leaflets. Soluble in alcohol and ether; very slightly soluble in water. Combustible.
2. p-Toluidine is a colorless solid.

Uses

Different sources of media describe the Uses of 106-49-0 differently. You can refer to the following data:
1. p-Toluidine is used as an intermediate in themanufacture of various dyes. It is also usedas a reagent for lignin and nitrites.
2. Manufacture of various dyes and other organic chemicals. o-Isomer also in printing textiles blue black; making colors fast to acids. p-Isomer also as a reagent for lignin, nitrite, phloroglucinol.
3. p-Toluidine is an intermediate in the production of dyes, organic chemicals and aromatic azo compounds. It serves as a component of accelerators for cyanoacrylate glues. Furthermore, it acts as a bidentate Schiff base ligand through condensation with salicylaldehyde. It reacts with catecholamine to form a dye which is useful for spectrophotometric determination of catecholamine drugs.

Definition

ChEBI: An aminotoluene in which the amino substituent is para to the methyl group.

Synthesis Reference(s)

Tetrahedron Letters, 32, p. 2759, 1991 DOI: 10.1016/0040-4039(91)85078-JJournal of the American Chemical Society, 89, p. 5311, 1967 DOI: 10.1021/ja00996a055

General Description

Colorless solid. Melting point 44°C (111°F). Specific gravity 1.046. Vapor heavier than air. Produces toxic oxides of nitrogen during combustion. May be absorbed through the skin. Used in dyes, and in organic chemical manufacturing.

Reactivity Profile

p-Toluidine neutralizes acids to form salts plus water in exothermic reactions. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated in combination with strong reducing agents, such as hydrides. Can react vigorously with oxidizing reagents. Emits very toxic fumes of oxides of nitrogen when heated to decomposition. Hypergolic reaction with red fuming nitric acid [Kit and Evered, 1960, p. 239, 242].

Health Hazard

Different sources of media describe the Health Hazard of 106-49-0 differently. You can refer to the following data:
1. Absorption of toxic quantities by any route causes cyanosis (blue discoloration of lips, nails, skin); nausea, vomiting, and coma may follow. Repeated inhalation of low concentrations may cause pallor, low-grade secondary anemia, fatigability, and loss of appetite. Contact with eyes causes irritation.
2. p-Toluidine is a mild to moderate irritanton the skin. The irritant effect on rabbits’eyes was strong. The toxic properties ofp-toluidine are similar to its ortho- and meta isomers and aniline. The clinical signs of tox icity are methemoglobinemia, anemia, andcyanosis. The major metabolite in urine afteroral application in male rats was 2-amino-5-methylphenol, which was excreted alongwith 3.5% unchanged p-toluidine (ACGIH1986). Exposure to 40-ppm concentrationfor 1 hour resulted in severe poisoning inhumans.

Fire Hazard

Special Hazards of Combustion Products: Toxic and flammable vapors may form in fire.

Safety Profile

Confirmed carcinogen. Poison by ingestion and intraperitoneal routes. Mutation data reported. A severe skin and eye irritant. Flammable when exposed to heat, flame, or oxidizers. Can react vigorously on contact with oxidzing materials. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits highly toxic fumes of NOx. See also o- TOLUIDINE and ANILINE.

Potential Exposure

para-Toluidine is used in dyes, and in organic chemical manufacturing

Carcinogenicity

In an 18-month p-toluidine hydrochloride diet carcinogenicity study, maleCDrats (1000 and 2000 ppmfor 18 months) did not develop statistically significant increases of tumors; however,CD-1male and female mice (1000 ppmfor 6 months and then 500 ppmfor additional 12 months; or 2000 ppm for 6 months and then 1000 ppm for additional 12 months) showed significant increases in liver carcinomas: in males at both dose levels and in females at the high dose level.

Shipping

UN3451 Toluidines, solid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials

Purification Methods

In general, methods similar to those for purifying aniline can be used. It can be separated from the o-and m-isomers by fractional crystallisation from its melt. p-Toluidine has been crystallised from hot water (charcoal), EtOH, *benzene, pet ether or EtOH/water (1:4), and dried in a vacuum desiccator. It can also be sublimed at 30o under vacuum. For further purification, use has been made of the oxalate, the sulfate and acetylation. The oxalate, formed as described for o-toluidine, is filtered, washed and recrystallised three times from hot distilled water. The base is regenerated with aqueous Na2CO3 and recrystallised three times from distilled water. [Berliner & May J Am Chem Soc 49 1007 1927.] Alternatively, p-toluidine is converted to its acetyl derivative which, after repeated crystallisation from EtOH, is hydrolysed by refluxing (50g) in a mixture of 500mL of water and 115mL of conc H2SO4 until a clear solution is obtained. The amine sulfate is isolated, suspended in water, and NaOH is added. The free base is distilled twice from zinc dust under vacuum. The p-toluidine is then recrystallised from pet ether and dried in a vacuum desiccator or in a vacuum for 6hours at 40o. The benzoyl derivative has m 158o (from EtOH). [Berliner & Berliner J Am Chem Soc 76 6179 1954, Moore et al. J Am Chem Soc 108 2257 1986, Beilstein 12 H 880, 12 I 140, 12 II 482, 12 III 2017, 12 IV 1866.]

Incompatibilities

para-Toluidine is incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. p-Toluidine neutralizes acids to form salts plus water in exothermic reactions. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated in combination with strong reducing agents, such as hydrides. Hypergolic reaction with red fuming nitric acid

Waste Disposal

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. Controlled incineration (oxides of nitrogen are removed from the effluent gas by scrubbers and/or thermal devices).

Check Digit Verification of cas no

The CAS Registry Mumber 106-49-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 6 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 106-49:
(5*1)+(4*0)+(3*6)+(2*4)+(1*9)=40
40 % 10 = 0
So 106-49-0 is a valid CAS Registry Number.
InChI:InChI=1/C7H9N/c1-6-2-4-7(8)5-3-6/h2-5H,8H2,1H3

106-49-0 Well-known Company Product Price

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  • CAS number
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  • Alfa Aesar

  • (A13698)  p-Toluidine, 99+%   

  • 106-49-0

  • 250g

  • 228.0CNY

  • Detail
  • Alfa Aesar

  • (A13698)  p-Toluidine, 99+%   

  • 106-49-0

  • 1000g

  • 563.0CNY

  • Detail
  • Alfa Aesar

  • (A13698)  p-Toluidine, 99+%   

  • 106-49-0

  • 5000g

  • 2351.0CNY

  • Detail
  • Sigma-Aldrich

  • (89630)  p-Toluidine  for spectrophotometric det. of Au, Tl(III), W, ≥99.0%

  • 106-49-0

  • 89630-100G

  • 769.86CNY

  • Detail
  • Sigma-Aldrich

  • (89630)  p-Toluidine  for spectrophotometric det. of Au, Tl(III), W, ≥99.0%

  • 106-49-0

  • 89630-500G

  • 3,223.35CNY

  • Detail

106-49-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name p-toluidine

1.2 Other means of identification

Product number -
Other names 4-aminotoluene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:106-49-0 SDS

106-49-0Synthetic route

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

1-methyl-4-nitrobenzene

p-toluidine
106-49-0

p-toluidine

Conditions
ConditionsYield
With triethylsilane; palladium dichloride In ethanol at 20℃; for 0.5h; Inert atmosphere;100%
With hydrazine hydrate In ethanol; water at 80℃; for 1h; chemoselective reaction;100%
With sodium tetrahydroborate In ethanol; water at 39.84℃; for 2h; Reagent/catalyst;100%
4-nitrobenzyl chloride
619-73-8

4-nitrobenzyl chloride

p-toluidine
106-49-0

p-toluidine

Conditions
ConditionsYield
With triethylsilane; palladium dichloride In ethanol at 20℃; for 0.5h; Inert atmosphere;100%
With hydrogen In ethanol at 80℃; under 2250.23 Torr; for 5h; Catalytic behavior; Inert atmosphere;95%
With [IrCl(CO)(PPh3)2]; hydrazine hydrate; potassium hydroxide In methanol at 160℃; for 3h; Wolff-Kishner Reduction; Sealed tube;51%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

p-toluidine
106-49-0

p-toluidine

Conditions
ConditionsYield
With triethylsilane; palladium dichloride In ethanol at 20℃; for 0.75h; Inert atmosphere;100%
With palladium 10% on activated carbon; ammonium formate In ethanol at 100℃; for 24h; Reagent/catalyst;90%
Stage #1: 4-nitrobenzaldehdye With hydrazine hydrate at 135℃; for 3h;
Stage #2: With potassium hydroxide at 135℃; for 24h;
63%
With hydrogen In ethanol; water at 25℃; under 750.075 Torr; for 4h; Schlenk technique;
N-(tert-butoxycarbonyl)-4-methylaniline
14618-59-8

N-(tert-butoxycarbonyl)-4-methylaniline

p-toluidine
106-49-0

p-toluidine

Conditions
ConditionsYield
With water at 100℃; for 10h; Inert atmosphere;99%
With 3-butyl-l-methyl-1H-imidazol-3-iumtrifloroacetate In 1,4-dioxane; water at 70 - 72℃; for 1h;98%
With Montmorillonite K10 In dichloromethane for 2h; deacylation; Heating;97%
With water at 150℃; for 4h; Subcritical conditions;88%
With zinc(II) iodide In toluene at 120℃; for 24h; Reagent/catalyst; Schlenk technique; Inert atmosphere; Glovebox;
2-oxo-2-phenylethyl p-tolylcarbamate

2-oxo-2-phenylethyl p-tolylcarbamate

p-toluidine
106-49-0

p-toluidine

Conditions
ConditionsYield
With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid In water; acetonitrile at 20℃; for 3h; Sealed tube; Irradiation; Inert atmosphere;99%
p-methylazidobenzene
2101-86-2

p-methylazidobenzene

p-toluidine
106-49-0

p-toluidine

Conditions
ConditionsYield
With butyltriphenylphosphonium tetrahydroborate In dichloromethane at 20℃; for 0.266667h;98%
With iron(III) chloride; sodium iodide In acetonitrile at 20℃; for 0.166667h;97%
With chloro-trimethyl-silane; sodium iodide In acetonitrile for 0.0833333h; Ambient temperature;97%
para-bromotoluene
106-38-7

para-bromotoluene

p-toluidine
106-49-0

p-toluidine

Conditions
ConditionsYield
With copper(I) oxide; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 80℃; for 15h;98%
Stage #1: para-bromotoluene With bis(bis(trimethylsilyl)amido)zinc(II); tri-tert-butyl phosphine; lithium chloride; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 50℃; for 9h;
Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether
93%
With ammonium hydroxide In neat (no solvent) at 60℃; for 8h;93%
N-(4-methylphenyl)formamide
3085-54-9

N-(4-methylphenyl)formamide

p-toluidine
106-49-0

p-toluidine

Conditions
ConditionsYield
With water; sodium hydroxide In ethanol at 65 - 70℃; for 1h;98%
With sodium hydroxide; water In 1,4-dioxane at 70℃; Kinetics; Thermodynamic data; isotope effect (D2O); ΔH(excit.), ΔS(excit.);
With sodium hydroxide In ethanol; water at 40℃; Kinetics;
4-Methylacetanilide
103-89-9

4-Methylacetanilide

p-toluidine
106-49-0

p-toluidine

Conditions
ConditionsYield
With 40% potassium fluoride/alumina at 85℃; for 0.0666667h; Microwave irradiation; Neat (no solvent);98%
With sodium hydroxide In methanol at 80℃;92%
With pepsin immobilized on terephthalaldehyde functionalized chitosan magnetic nanoparticle In acetonitrile at 20℃; for 48h; pH=2;83%
N-hydroxy-4-methylbenzamide
2318-82-3

N-hydroxy-4-methylbenzamide

p-toluidine
106-49-0

p-toluidine

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 90℃; for 2h; Lossen rearrangement;98%
With palladium diacetate; triethylamine In acetonitrile at 90℃; for 24h; Solvent; Lossen Rearrangement; Sealed tube;98%
With potassium carbonate In dimethyl sulfoxide at 90℃; for 2h; Reagent/catalyst; Solvent; Lossen Rearrangement;98%
3-azidohomoadamantane
63534-35-0

3-azidohomoadamantane

toluene
108-88-3

toluene

A

1-(adamantan-1-ylmethyl)-4-methylbenzene
76429-91-9

1-(adamantan-1-ylmethyl)-4-methylbenzene

B

p-toluidine
106-49-0

p-toluidine

Conditions
ConditionsYield
With aluminium trichloride at 80℃; for 1.5h; Yields of byproduct given;A 97%
B n/a
p-tolyl triflate
29540-83-8

p-tolyl triflate

p-toluidine
106-49-0

p-toluidine

Conditions
ConditionsYield
Stage #1: p-tolyl triflate With bis(bis(trimethylsilyl)amido)zinc(II); tri-tert-butyl phosphine; tetrabutylammomium bromide; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 50℃; for 6h;
Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether
97%
Multi-step reaction with 2 steps
1: Trimethyl borate; water; trifluoroacetic acid; acetone / 15 °C / UV-irradiation; Inert atmosphere
2: sodium hydroxide / methanol / 80 °C
View Scheme
N-(p-Tolyl)carbamidsaeure-β-chlorethylester
74552-28-6

N-(p-Tolyl)carbamidsaeure-β-chlorethylester

p-toluidine
106-49-0

p-toluidine

Conditions
ConditionsYield
With ammonium chloride; zinc; hydroxycobalamine In ethanol; water at 20℃; for 15h;96%
4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

p-toluidine
106-49-0

p-toluidine

Conditions
ConditionsYield
With sodium tetrahydroborate; titanium tetrachloride In 1,2-dimethoxyethane for 14h; Ambient temperature;96%
1,1,1-Trimethyl-N-(4-methylphenyl)-N-(trimethylsilyl)silanamine
31935-68-9

1,1,1-Trimethyl-N-(4-methylphenyl)-N-(trimethylsilyl)silanamine

p-toluidine
106-49-0

p-toluidine

Conditions
ConditionsYield
With hydrogenchloride; water In methanol at 20℃; for 1h;96%
With hydrogenchloride In diethyl ether
With hydrogenchloride In chloroform; water for 1h;23.6 mg
4-tolyl iodide
624-31-7

4-tolyl iodide

p-toluidine
106-49-0

p-toluidine

Conditions
ConditionsYield
With copper(I) oxide; ammonium hydroxide; C17H14N2O3; potassium hydroxide In ethanol at 60℃; for 24h; Schlenk technique; Inert atmosphere;96%
With ammonia; triethylamine In water at 20℃; for 3.5h;96%
With copper(l) iodide; ascorbic acid In ammonia at 25℃; for 18h; Kinetics; liquid NH3;95%
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

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

1-methyl-4-nitrobenzene

A

quinoline
91-22-5

quinoline

B

p-toluidine
106-49-0

p-toluidine

Conditions
ConditionsYield
With nickel-nitrogen-doped carbon framework In water at 145℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry;A 94%
B 96%
2-((p-toluidino)methyl)phenol
14674-88-5

2-((p-toluidino)methyl)phenol

A

p-toluidine
106-49-0

p-toluidine

B

C21H18O3

C21H18O3

Conditions
ConditionsYield
at 230℃; under 10 Torr; for 0.0833333h; Product distribution; pyrolysis without solvent;A 95%
B n/a
trifluoroacetic acid
76-05-1

trifluoroacetic acid

S,S-dimethyl-4-methylanilinosulfonium picrate

S,S-dimethyl-4-methylanilinosulfonium picrate

A

2,2,2-trifluoro-N-(4-methylphenyl)acetamide
350-96-9

2,2,2-trifluoro-N-(4-methylphenyl)acetamide

B

p-toluidine
106-49-0

p-toluidine

C

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
at 50℃; for 5h; Elimination; acylation; retro-Pummerer reaction;A 3%
B 95%
C 67%
N-benzyl-N-(4-methylphenyl)amine
5405-15-2

N-benzyl-N-(4-methylphenyl)amine

p-toluidine
106-49-0

p-toluidine

Conditions
ConditionsYield
With ammonium formate; zinc In ethylene glycol for 0.05h; microwave irradiation;95%
3-oxo-N-(p-tolyl)butanamide
2415-85-2

3-oxo-N-(p-tolyl)butanamide

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

A

2-Methyl-1H-benzimidazole
615-15-6

2-Methyl-1H-benzimidazole

B

p-toluidine
106-49-0

p-toluidine

Conditions
ConditionsYield
With 1-n-butyl-3-methylimidazolim bromide In neat (no solvent) at 120℃; for 2h;A 95%
B 90%
4'-methylbenzenesulphenanilide
14933-93-8

4'-methylbenzenesulphenanilide

A

2,7-dimethylphenazine
3236-92-8

2,7-dimethylphenazine

B

p-toluidine
106-49-0

p-toluidine

C

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
With trifluoroacetic acid In benzene at 25℃;A 35%
B 55%
C 94%
7-methyl-1,2,3,4-tetrahydroquinoline
58960-03-5

7-methyl-1,2,3,4-tetrahydroquinoline

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

1-methyl-4-nitrobenzene

A

7-methylquinoline
612-60-2

7-methylquinoline

B

p-toluidine
106-49-0

p-toluidine

Conditions
ConditionsYield
With nickel-nitrogen-doped carbon framework In water at 145℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry;A 92%
B 94%
4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

p-toluidine
106-49-0

p-toluidine

Conditions
ConditionsYield
With dimethylsulfide borane complex In chlorobenzene 1) 15 min, r.t. 2) 5 h, reflux;93%
1,2-di(p-tolyl)diazene
501-60-0, 21650-54-4, 30926-02-4

1,2-di(p-tolyl)diazene

p-toluidine
106-49-0

p-toluidine

Conditions
ConditionsYield
With potassium hydroxide; nickel-incorporated hexagonal mesoporous aluminophosphate In isopropyl alcohol at 82.84℃; for 1.5h;93%
With perchloric acid In isopropyl alcohol; acetonitrile at 25℃; for 0.75h; pH=2; Inert atmosphere; Irradiation;92%
With ethanol; iron; calcium chloride at 60℃; for 0.5h;92%
4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

p-toluidine
106-49-0

p-toluidine

Conditions
ConditionsYield
With copper(I) oxide; ammonium hydroxide; air In methanol at 20℃; for 12h;93%
With sodium hydroxide; hydroxylamine-O-sulfonic acid In acetonitrile at 20℃; for 16h;90%
With N-Bromosuccinimide; CYANAMID; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 20℃; for 1h; chemoselective reaction;90%
N-{(Z)-1,3-Diphenyl-3-[(Z)-p-tolylimino]-propenyl}-methanesulfonamide
126629-91-2

N-{(Z)-1,3-Diphenyl-3-[(Z)-p-tolylimino]-propenyl}-methanesulfonamide

A

3,5-Diphenyl-2H-1,2-thiazin-1,1-dioxid
96355-37-2

3,5-Diphenyl-2H-1,2-thiazin-1,1-dioxid

B

p-toluidine
106-49-0

p-toluidine

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at -78 - 25℃; for 12h;A 92%
B n/a
N-{(Z)-3-Phenyl-1-p-tolyl-3-[(Z)-p-tolylimino]-propenyl}-methanesulfonamide
126629-93-4

N-{(Z)-3-Phenyl-1-p-tolyl-3-[(Z)-p-tolylimino]-propenyl}-methanesulfonamide

A

5-Phenyl-3-p-tolyl-2H-[1,2]thiazine 1,1-dioxide
126629-99-0

5-Phenyl-3-p-tolyl-2H-[1,2]thiazine 1,1-dioxide

B

p-toluidine
106-49-0

p-toluidine

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at -78 - 25℃; for 12h;A 92%
B n/a
para-chlorotoluene
106-43-4

para-chlorotoluene

p-toluidine
106-49-0

p-toluidine

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; ammonium hydroxide In PEG1000-DIL; methyl cyclohexane at 60℃; for 8h;92%
Stage #1: para-chlorotoluene With bis(bis(trimethylsilyl)amido)zinc(II); tri-tert-butyl phosphine; lithium chloride; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 90℃; for 12h;
Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether
90%
With copper(I) oxide; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 110℃; for 12h; Microwave irradiation;89%
furfural
98-01-1

furfural

p-toluidine
106-49-0

p-toluidine

furfurylidene-p-toluidine
13060-72-5

furfurylidene-p-toluidine

Conditions
ConditionsYield
In methanol at 20℃; for 24h;100%
In methanol at 20℃; for 24h;100%
In methanol at 20℃;85%
phthalic anhydride
85-44-9

phthalic anhydride

p-toluidine
106-49-0

p-toluidine

2-p-tolylisoindoline-1,3-dione
2142-03-2

2-p-tolylisoindoline-1,3-dione

Conditions
ConditionsYield
for 1h; Solid phase reaction; condensation;100%
With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 80℃; for 8h;97%
In decaethylene glycol at 120℃; for 3h;97%
acetic anhydride
108-24-7

acetic anhydride

p-toluidine
106-49-0

p-toluidine

4-Methylacetanilide
103-89-9

4-Methylacetanilide

Conditions
ConditionsYield
In dichloromethane at 20℃; Inert atmosphere;100%
With Methylenediphosphonic acid at 20℃; for 1h; neat (no solvent);99%
With pyridine; aluminum oxide at 125 - 127℃; for 2h; microwave irradiation;98%
cinnamoyl chloride
102-92-1

cinnamoyl chloride

p-toluidine
106-49-0

p-toluidine

N-(4-methylphenyl)-3-phenyl-2-propenamide
6876-68-2

N-(4-methylphenyl)-3-phenyl-2-propenamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; Inert atmosphere;100%
With triethylamine In ethyl acetate at 0 - 20℃;88%
With potassium hydroxide
3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

p-toluidine
106-49-0

p-toluidine

N-(3-nitrobenzylidene)-4-methylbenzenamine
17064-95-8

N-(3-nitrobenzylidene)-4-methylbenzenamine

Conditions
ConditionsYield
100%
With chitosan In ethanol; water at 20℃; for 0.333333h;85%
With ethanol
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

p-toluidine
106-49-0

p-toluidine

N-(4-nitrobenzylidene)-4-methylaniline
730-39-2, 33442-37-4, 149742-47-2

N-(4-nitrobenzylidene)-4-methylaniline

Conditions
ConditionsYield
for 24h; Ambient temperature;100%
100%
With montmorillonite at 20℃; for 0.0666667h; Neat (no solvent);98%
2-Hydroxy-1,4-naphthoquinone
83-72-7

2-Hydroxy-1,4-naphthoquinone

p-toluidine
106-49-0

p-toluidine

2-(p-toluidino)-1,4-naphthoquinone
57182-49-7

2-(p-toluidino)-1,4-naphthoquinone

Conditions
ConditionsYield
In neat (no solvent) at 100℃; under 750.075 Torr; for 0.05h; Microwave irradiation;100%
With acetic acid
With ethanol
p-toluidine
106-49-0

p-toluidine

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

p-hydroxybenzal-p-toluidine
3230-51-1

p-hydroxybenzal-p-toluidine

Conditions
ConditionsYield
for 6h; Ambient temperature;100%
100%
In ethyl 2-hydroxypropionate at 20℃; for 0.0333333h;90%
p-toluidine
106-49-0

p-toluidine

dimedone
126-81-8

dimedone

3-(p-tolylamino)-5,5-dimethylcyclohex-2-enone
36646-78-3

3-(p-tolylamino)-5,5-dimethylcyclohex-2-enone

Conditions
ConditionsYield
at 20℃; for 0.5h; Solid phase reaction; condensation;100%
With fibrous nano silica sulfuric acid In neat (no solvent) at 80℃; for 0.0333333h; Green chemistry;97%
With silica sulfuric acid In acetonitrile for 0.0194444h; Microwave irradiation;96%
p-toluidine
106-49-0

p-toluidine

3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

1,2-dimethoxy-4-<<(4-methylphenyl)imino>methyl>benzene
67101-90-0

1,2-dimethoxy-4-<<(4-methylphenyl)imino>methyl>benzene

Conditions
ConditionsYield
In toluene Heating;100%
p-toluidine
106-49-0

p-toluidine

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

4-methyl-N-(4-methylphenyl)benzenesulfonamide
599-86-0

4-methyl-N-(4-methylphenyl)benzenesulfonamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 16h;100%
With pyridine at 0 - 25℃;100%
In water at 110℃; for 0.0833333h; Microwave irradiation; Green chemistry; chemoselective reaction;98%
p-toluidine
106-49-0

p-toluidine

2-chloropropionyl chloride
625-36-5

2-chloropropionyl chloride

3-chloro-N-(4-methylphenyl)propionamide
19342-88-2

3-chloro-N-(4-methylphenyl)propionamide

Conditions
ConditionsYield
In acetone for 1h; Acylation; Heating;100%
In water; acetone for 6h; Reflux;100%
With potassium carbonate In acetone at 0℃; for 1h; Condensation;95%
p-toluidine
106-49-0

p-toluidine

2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

4-methyl-(2-nitrobenzylidene)aniline
17064-82-3

4-methyl-(2-nitrobenzylidene)aniline

Conditions
ConditionsYield
100%
In ethanol for 3h; Reflux;77.2%
In ethanol for 3h; Reflux;77.2%
p-toluidine
106-49-0

p-toluidine

n-butyl isocyanide
111-36-4

n-butyl isocyanide

N-butyl-N’-(4-methylphenyl)urea
22671-74-5

N-butyl-N’-(4-methylphenyl)urea

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 24h; Ambient temperature;100%
With toluene
p-toluidine
106-49-0

p-toluidine

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

dimethyl (Z)-N-(4-methylphenyl)aminofumarate
24559-80-6

dimethyl (Z)-N-(4-methylphenyl)aminofumarate

Conditions
ConditionsYield
at 20℃; for 0.133333h; Michael addition;100%
In benzene at 5 - 10℃;70%
In diethyl ether
maleic anhydride
108-31-6

maleic anhydride

p-toluidine
106-49-0

p-toluidine

4-methylmaleanilic acid
24870-11-9

4-methylmaleanilic acid

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 110℃; for 5h;100%
In diethyl ether at 20℃; for 2h;98%
In chloroform for 7h;97%
benzyl bromide
100-39-0

benzyl bromide

p-toluidine
106-49-0

p-toluidine

N,N-dibenzyl-4-methylbenzenamine
5459-79-0

N,N-dibenzyl-4-methylbenzenamine

Conditions
ConditionsYield
With sodium hydrogencarbonate In N,N,N,N,N,N-hexamethylphosphoric triamide for 0.5h; Heating; 3 equivalents of BzBr;100%
With montmorillonite-KSF clay supported CuO nanoparticles In neat (no solvent) at 20℃; for 0.75h; Sonication; Green chemistry; chemoselective reaction;78%
With sodium dodecyl-sulfate; sodium hydrogencarbonate In water at 80℃; for 1h; Inert atmosphere;71%
With sodium dodecyl-sulfate; sodium hydrogencarbonate In water at 80℃; for 1h;70%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

p-toluidine
106-49-0

p-toluidine

N-(4-chlorobenzylidene)-4-toluidine
15485-32-2

N-(4-chlorobenzylidene)-4-toluidine

Conditions
ConditionsYield
for 6h; Ambient temperature;100%
In ethyl 2-hydroxypropionate at 20℃; for 0.0333333h;96%
With montmorillonite at 20℃; for 0.1h; Neat (no solvent);96%
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

p-toluidine
106-49-0

p-toluidine

ethyl 2-(4-methylphenylimino)acetate
121641-60-9

ethyl 2-(4-methylphenylimino)acetate

Conditions
ConditionsYield
With sodium sulfate In dichloromethane for 0.5h;100%
With magnesium sulfate In toluene at 25℃; for 0.5h;100%
for 1h; Green chemistry;75%
1,1,1-trifluoro-4,4-diethoxy-3-buten-2-one
40657-29-2

1,1,1-trifluoro-4,4-diethoxy-3-buten-2-one

p-toluidine
106-49-0

p-toluidine

(E)-4-Ethoxy-1,1,1-trifluoro-4-p-tolylamino-but-3-en-2-one
128648-64-6

(E)-4-Ethoxy-1,1,1-trifluoro-4-p-tolylamino-but-3-en-2-one

Conditions
ConditionsYield
In acetonitrile for 18h; Ambient temperature;100%
(2-formylphenyl)butyl tellurium dibromide
128346-30-5

(2-formylphenyl)butyl tellurium dibromide

p-toluidine
106-49-0

p-toluidine

2-(4'-methylphenyliminomethinyl)phenyltellurenyl bromide
130191-28-5

2-(4'-methylphenyliminomethinyl)phenyltellurenyl bromide

Conditions
ConditionsYield
With trifluoroacetic acid In benzene100%
2-<(3-Chloropropyl)amino>-4H-3,1-benzoxazin-4-one
94507-26-3

2-<(3-Chloropropyl)amino>-4H-3,1-benzoxazin-4-one

p-toluidine
106-49-0

p-toluidine

N-(4-Methylphenyl)-2-<3-(3-chloropropyl)ureido>benzamide
94507-35-4

N-(4-Methylphenyl)-2-<3-(3-chloropropyl)ureido>benzamide

Conditions
ConditionsYield
for 0.05h; Heating;100%
4-[4a-Methoxy-7-(4-methoxy-3,6-dioxo-cyclohexa-1,4-dienyl)-5,8-dioxo-4-phenyl-4a,5,8,8a-tetrahydro-4H-quinolin-1-yl]-benzoic acid
84410-20-8

4-[4a-Methoxy-7-(4-methoxy-3,6-dioxo-cyclohexa-1,4-dienyl)-5,8-dioxo-4-phenyl-4a,5,8,8a-tetrahydro-4H-quinolin-1-yl]-benzoic acid

p-toluidine
106-49-0

p-toluidine

4-(9-Hydroxy-4a,8-dimethoxy-5,11-dioxo-4-phenyl-6-p-tolyl-4,4a,5,6,11,11a-hexahydro-pyrido[3,2-b]carbazol-1-yl)-benzoic acid
84423-43-8

4-(9-Hydroxy-4a,8-dimethoxy-5,11-dioxo-4-phenyl-6-p-tolyl-4,4a,5,6,11,11a-hexahydro-pyrido[3,2-b]carbazol-1-yl)-benzoic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethanol; water for 4h; Heating;100%
p-toluidine
106-49-0

p-toluidine

vanillin
121-33-5

vanillin

3-methoxy-4-{[(4-methylphenyl)imino]methyl}phenol
53304-12-4

3-methoxy-4-{[(4-methylphenyl)imino]methyl}phenol

Conditions
ConditionsYield
for 2h; Ambient temperature;100%
In ethanol for 0.333333h; Reflux;95.51%
sodium hydrogen sulfate; silica gel at 54 - 56℃; for 0.0236111h; microwave irradiation;91%
p-toluidine
106-49-0

p-toluidine

3-Bromopropionyl chloride
15486-96-1

3-Bromopropionyl chloride

3-bomo-N-(4-methylphenyl)propanamide
21437-82-1

3-bomo-N-(4-methylphenyl)propanamide

Conditions
ConditionsYield
With potassium carbonate In 1,2-dichloro-ethane at 20℃; for 1h; Time; Inert atmosphere;100%
With dmap In tetrahydrofuran at 0 - 20℃; for 1h;75%
With triethylamine In benzene70%
furfural
98-01-1

furfural

p-toluidine
106-49-0

p-toluidine

4-methyl-N-((tetrahydrofuran-2-yl)methyl)aniline

4-methyl-N-((tetrahydrofuran-2-yl)methyl)aniline

Conditions
ConditionsYield
With hydrogen; AV-17-8-Pd In ethanol at 45℃; under 750.06 Torr; Rate constant; Thermodynamic data; E(a);100%
With hydrogen; AV-17-8-Pd In ethanol at 45℃; under 750.06 Torr;100%
With Pd/Al2O3; hydrogen In ethanol at 80℃; under 750.075 Torr; for 12h;94%
p-toluidine
106-49-0

p-toluidine

Cinnamoyl chloride
102-92-1

Cinnamoyl chloride

(2E)-N-(4-methylphenyl)-3-phenylprop-2-enamide
134430-88-9

(2E)-N-(4-methylphenyl)-3-phenylprop-2-enamide

Conditions
ConditionsYield
With potassium carbonate In water; acetone at 0℃; for 2h;100%
Stage #1: Cinnamoyl chloride With pyridine; dmap In dichloromethane at 0℃; for 0.416667h; Inert atmosphere;
Stage #2: p-toluidine In dichloromethane at 0 - 20℃;
86%
With dmap; sodium hydrogencarbonate In dichloromethane at 20℃;84%
cyclohexane-1,2-epoxide
286-20-4

cyclohexane-1,2-epoxide

p-toluidine
106-49-0

p-toluidine

trans-2-(p-tolylamino)cyclohexanol

trans-2-(p-tolylamino)cyclohexanol

Conditions
ConditionsYield
With zirconium(IV) chloride at 20℃; for 0.25h;100%
With [{(CH3)5Cp}2Zr(CH3CN)2(H2O)][OSO2C6F5]2·CH3CN In neat (no solvent) at 20℃; for 0.166667h; diastereospecific reaction;99%
With zinc(II) perchlorate hexahydrate at 20℃; for 0.5h;98%
bromocyane
506-68-3

bromocyane

p-toluidine
106-49-0

p-toluidine

N-(4-methylphenyl)cyanamide
10532-64-6

N-(4-methylphenyl)cyanamide

Conditions
ConditionsYield
With trimethylamine Ambient temperature;100%
In diethyl ether; tetrahydrofyran at 0℃; for 4h;95%
With triethylamine In diethyl ether at 0℃;83%

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The charge transfer complexes of the donor p-toluidine with π-acceptor picric acid have been studied spectrophotometrically in various solvents such as carbon tetrachloride, chloroform, dichloromethane acetone, ethanol, and methanol at room temperature using absorption spectrophotometer. The re...detailed

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Molecular structures, charge distributions, and vibrational analyses of the tetracoordinate Cu(II), Zn(II), Cd(II), and Hg(II) bromide complexes of p-Toluidine (cas 106-49-0) investigated by density functional theory in comparison with experiments08/23/2019

The Cu(II), Zn(II), Cd(II), and Hg(II) bromide complexes of p-toluidine have been studied with B3LYP calculations by using def2-TZVP basis set at the metal atoms and using def2-TZVP and 6-311G+(d,p) basis sets at the remaining atoms. Both basis set combinations give analogous results, which vali...detailed

Spectral and hydrodynamic studies on p-Toluidine (cas 106-49-0) induced growth in cationic micelle08/21/2019

The effect of p-toluidine (PTD) on the growth of cationic surfactant micelles in aqueous solutions was examined by viscosity, UV–visible spectroscopy, dynamic light scattering (DLS), 1H NMR and nuclear Overhauser effect spectroscopy (NOESY). Viscosity and scattering results are used to follow t...detailed

Dissimilar effects of solubilized p-Toluidine (cas 106-49-0) on the shape of micelles of differently charged surfactants08/20/2019

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New organic semiconductor thin film derived from p-Toluidine (cas 106-49-0) monomer08/18/2019

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106-49-0Relevant articles and documents

Zeolite-Catalyzed Isomerization of Aromatic Amines to Methyl-Aza-Aromatics

Stamm, T.,Kouwenhoven, H. W.,Seebach, D.,Prins, R.

, p. 268 - 282 (1995)

The scope and mechanism of the isomerization of arylamines to methyl-substituted aromatic heterocycles have been studied.Aniline, toluidines, naphthylamines and m-phenylenediamine all reacted to the corresponding ortho-methyl-substituted aza-aromatiics when exposed to high NH3 pressure and elevated temperature in the presence of acid catalysts.Zeolites with a three-dimensional pore structure, especially H-ZSM-5, showed the best performance.Optimum reaction conditions are around 600 K and 10 MPa.Two mechanisms which had been proposed earlier for this apparent N-ortho C exchange reaction proved untenable.Neither incorporation of the N atom into the aromatic ring nor a mechanism based on an intramolecular Ritter reaction could explain the required high NH3 pressure or the product distribution.Two new mechanisms are proposed which can explain all observations.In both mechanisms, reaction starts with addition of NH3 to the arylamine, followed by ring opening.In one mechanism an alkyno-imine intermediate is formed; in the other mechanism an enamino-imine intermediate is formed through a reverse aldol reaction.In both cases ring closure and NH3 elimination lead to the required aromatic heterocycles.The high NH3 pressure is explained by the need to add NH3 to the aromatic ring, and the high temperature by the need to desorb NH3 from the acid sites.

-

Campbell

, p. 4019 (1951)

-

Microbial deoxygenation of N-oxides with Baker's yeast-NaOH

Baik, Woonphil,Kim, Dong Ik,Koo, Sangho,Rhee, Jong Uk,Shin, Sung Hee,Kim, Byeong Hyo

, p. 845 - 848 (1997)

The microbial deoxygenation of a series of aromatic and heteroaromatic N-oxide compounds, including quinoline N-oxides, isoquinoline N-oxides, 2-aryl-2H-benzotriazole 1-oxides, benzo[c]cinnoline N-oxide and azoxybenzenes, has been performed with bakers'yeast-NaOH.

Electrophilic amination of methylbenzenes with sodium azide in trifluoromethanesulfonic acid

Borodkin,Elanov,Shubin

, p. 934 - 935 (2009)

-

Simple and efficient reduction of aromatic nitro compounds using recyclable polymer-supported formate and magnesium

Abiraj, Keelara,Srinivasa, Gejjalagere R.,Gowda, D. Channe

, p. 149 - 151 (2005)

Aromatic nitro compounds were chemoselectively reduced to the corresponding amines using recyclable polymer-supported formate as a hydrogen donor in the presence of low-cost magnesium powder at room temperature. Use of the immobilized hydrogen donor affords the product amine in excellent yield (90-97%) without the need for any Chromatographic purification steps. This method was found to be highly facile with selectivity over several other functional groups, such as halogen, alkene, nitrile, carbonyl, ester, amide, methoxy, phenol, and hydroxyl groups. CSIRO 2005.

-

Keller,Smith

, p. 1122 (1944)

-

-

Brown,Etzel,Henke

, p. 635 (1928)

-

Mild and general procedure for Pd/C-catalyzed hydrodechlorination of aromatic chlorides

Sajiki, Hironao,Kume, Akira,Hattori, Kazuyuki,Hirota, Kosaku

, p. 7247 - 7250 (2002)

A mild and efficient one-pot hydrodechlorination using a Pd/C-Et3N system proceeds at room temperature, which is general for the dechlorination of a variety of aromatic chlorides.

Metal-assisted lossen rearrangement

Jasikova, Lucie,Hanikyrova, Eva,Skriba, Anton,Jasik, Juraj,Roithova, Jana

, p. 2829 - 2836 (2012)

A new reaction mechanism for the Lossen rearrangement of hydroxamic acids catalyzed by basic salts is presented. It is shown that the rearrangement proceeds in metal complexes of deprotonated hydroxamic acids. The deprotonation can occur either at the oxygen atom (observed for the zinc complexes) or at the nitrogen atom (observed for the potassium complexes). Both anionic forms are characterized by infrared multiphoton dissociation spectroscopy. The rearrangements proceed from the reactive N-deprotonated metal hydroxamates and lead to metal carbamates. The mechanism is elucidated by computational chemistry, mass-spectrometric studies, and preparative experiments.

Rearrangement of N-Methylaniline over H-ZSM-5, H-Theta-1, and H-Y Zeolites

Mordi, Raphael C.,Dwyer, John,Fields, Roy

, p. 627 - 630 (1993)

-

Nickel oxide nanoparticles grafted on reduced graphene oxide (rGO/NiO) as efficient photocatalyst for reduction of nitroaromatics under visible light irradiation

Al-Nafiey, Amer,Kumar, Anurag,Kumar, Malika,Addad, Ahmed,Sieber, Brigitte,Szunerits, Sabine,Boukherroub, Rabah,Jain, Suman L.

, p. 198 - 207 (2017)

Nickel oxide nanoparticles were grafted on reduced graphene oxide via simultaneous reduction of graphene oxide and nickel salt in a single step reaction. The synthesized material (rGO/NiO) was found to be efficient visible light active photocatalyst for the reduction of nitroaromatic derivatives to their corresponding amino compounds. Hydrazine monohydrate provided necessary protons and electrons for the targeted reaction. After completion of the reaction, the photocatalyst could readily be recovered by simple external magnet and could be reused for six runs without any significant loss of its activity. More importantly, the photocatalyst did not show any leaching during the reaction as confirmed by ICP-AES analysis of the recovered catalyst.

Photocatalytic formation of a carbamate through ethanol-assisted carbonylation of p-nitrotoluene

Maldotti, Andrea,Amadelli, Rossano,Samiolo, Luca,Molinari, Alessandra,Penoni, Andrea,Tollari, Stefano,Cenini, Sergio

, p. 1749 - 1751 (2005)

The nitroarene p-nitrotoluene is converted with a selectivity higher than 85% to the corresponding carbamate at room temperature and atmospheric pressure, using photoexcited particles of TiO2 as catalyst and EtOH as carbonylating species. The Royal Society of Chemistry 2005.

Nanocrystalline Pt-CeO2 as an efficient catalyst for a room temperature selective reduction of nitroarenes

Shukla, Astha,Singha, Rajib Kumar,Sasaki, Takehiko,Bal, Rajaram

, p. 785 - 790 (2015)

We have developed a new synthesis strategy to prepare Pt nanoparticles with size between 2 and 5 nm supported on CeO2 nanoparticles with size between 30 and 60 nm by the hydrothermal method in the presence of the surfactant cetyltrimethyl ammonium bromide (CTAB) and a polymer (PVP). It was found that the catalyst is highly active for the chemoselective hydrogenation of nitro compounds in aqueous medium in the presence of molecular hydrogen at room temperature (25 °C). The catalyst was characterized by XRD, ICP-AES, XPS, BET-surface area measurements, SEM, TEM and EXAFS. Different reaction parameters like reaction time, catalyst ratio, Pt loading etc. were studied in detail. The investigation revealed that the site of Pt plays a crucial role in the activity by favouring the reduction of nitro-compounds. The catalyst shows >99.9% conversion of nitro-compounds with 99% selectivity of amino compounds. The reusability of the catalyst was tested by conducting the experiment with the same catalyst and it was found that the catalyst does not change its activity and selectivity even after five reuses. This journal is

SYNTHESIS OF METHYL-N-ARYLCARBAMATES BY THE CARBONYLATION OF AZOXY, AZO, AND NITRO COMPOUNDS

Manov-Yuvenskii, V. I.,Petrovskii, K. B.,Lapidus, A. L.

, p. 543 - 545 (1984)

-

-

Gilman,Sternbach

, p. 465 (1971)

-

Magnetically Recyclable Metal–Organic Framework@Fe3O4 Composite-Catalyzed Facile Reduction of Nitroarene Compounds in Aqueous Medium

Yang, Sen,Zhang, Zhi-Hui,Chen, Qun,He, Ming-Yang,Wang, Liang

, (2018)

A kind of Metal–organic framework (MOF) composite namely Cu-BTC@Fe3O4 (BTC?=?1,3,5-benzenetricarboxylate) was prepared and showed good catalytic activity toward the reduction of nitroarenes. This reaction proceeded smoothly under mild reaction conditions in aqueous medium using sodium borohydride as the reduction agent, affording the corresponding anilines in good to excellent yields. In addition, the catalyst could be easily recovered with an external permanent magnet and be reused for successive six runs with slight decrease in its activity.

-

Albisetti et al.

, p. 1489,1492 (1959)

-

Pd Nanoparticles Assembled on Metalporphyrin-Based Microporous Organic Polymer as Efficient Catalyst for Tandem Dehydrogenation of Ammonia Borane and Hydrogenation of Nitro Compounds

Zou, Zhijuan,Jiang, Yaya,Song, Kunpeng

, p. 1277 - 1286 (2020)

Abstract: Metalporphyrin-based porous polymers supporting high dispersed Pd nanoparticle (NP) catalysts (HUST-1-Pd) were prepared with a novel solvent-knitting hyper-crosslinked polymer method using 5-, 10-, 15-, and 20-tetraphenylporphyrin (TPP) as building blocks. The N2 sorption isotherms of the catalysts show that the HUST-1-Pd possesses many ultra-micropores and continuous mesopores. The NPs are assembled on tetraphenylporphyrin structures and show Pd-N4 composition-dependent catalysis for methanolysis of ammonia borane (AB) and hydrogenation of aromatic nitro compounds to primary amines in methanol solutions at room temperature. The nano-palladium reduced by NaBH4 has efficient catalytic activity for AB methanolysis. A variety of R-NO2 derivatives were reduced selectively into R-NH2 via palladium catalyzed tandem reactions with 5–30?min of reaction time with conversion yields reaching up to 90%. The derivatives also give excellent recycling performance (more than 10 times). Furthermore, the turnover frequency (TOF) can reach 87,209?h?1. The HUST-1-Pd compounds represent a unique metal catalyst for hydrogenation reactions in a green environment without using pure hydrogen. Graphic Abstract: A monodisperse Pd NPs embed in porphyrin-based microporous organic polymer was reported to catalyse the tandem dehydrogenation of ammonia borane and hydrogenation of R-NO2 to R-NH2 at room temperature. The catalyst is efficient and reusable in an environment-friendly process with short reaction times and high yields.[Figure not available: see fulltext.]

One-pot tandem catalysis over Pd@MIL-101: boosting the efficiency of nitro compound hydrogenation by coupling with ammonia borane dehydrogenation

Yang, Qihao,Chen, Yu-Zhen,Wang, Zhiyong U.,Xu, Qiang,Jiang, Hai-Long

, p. 10419 - 10422 (2015)

The hydrogenation efficiency of nitro compounds was found to be greatly boosted by coupling with dehydrogenation of ammonia borane. The Pd@MIL-101 with tiny Pd NPs is exceptionally efficient and recyclable in the tandem reactions and diverse nitro compounds can be selectively reduced to the corresponding amines in 1.5-5 min with quantitative yields.

Sulfamide chemistry applied to the functionalization of self-assembled monolayers on gold surfaces

Pantaine, Lo?c,Humblot, Vincent,Coeffard, Vincent,Vallée, Anne

, p. 648 - 658 (2017)

Aniline-terminated self-assembled monolayers (SAMs) on gold surfaces have successfully reacted with ArSO2NHOSO2Ar (Ar = 4-MeC6H4 or 4-FC6H4) resulting in monolayers with sulfamide moieties

-

Micewicz

, (1928)

-

Transition metal imide/organic imine metathesis reactions: Unexpected observations

McInnes, Jacqueline M.,Mountford, Philip

, p. 1669 - 1670 (1998)

Mixtures of [Ti(NBut)Cl2(py)3] 1 and PhC(NAr)H (Ar = C6H3Me2-2,6 or C6H4Me-4) gave quantitative conversion to [Ti(NAr)Cl2(py)3] and PhC(NBut)H, the products of Ti=N-But/C=NAr transition metal imide/organic imine metathesis; examination of the kinetics for Ar = C6H4Me-4 showed that the rate limiting step for this process is zero order in [1], demonstrating that these reactions do not involve metal imide particiption in the rate limiting step.

PROTONATION OF REAGENTS AND ACID-BASE CATALYSIS IN ACYLATION

Kalnin'sh, K. K.

, p. 822 - 828 (1992)

The kinetic characteristics of the model reaction of electron transfer and the reaction of acylation of aromatic amines by aromatic acid anhydrides were investigated as a function of the concentration of acid catalyst and a correlation was established between the type of this function and the characteristics of protonation of the amines.The rate constants of the catalytic and noncatalytic flows of the forward and reverse reactions in the phthalic anhydride-p-toluidine system were determined as a function of the molarity and proton-acceptor properties of the solvent.The mechanism of acid-base catalysis was examined as a sequence of proton and electron transfer processes. Keywords: catalysis, kinetics, protonation.

Iodide Reduction of Sulfilimines. 2. Evidence for Concurrent Stepwise and Concerted Mechanisms for the Decomposition of Sulfurane Intermediates

Young, Paul R.,Huang, H. C.

, p. 1805 - 1809 (1987)

The iodide reduction of N-(substituted ethyl or phenyl)-S,S-dimethylsulfilimmonium salts (aqueous solution, 25 deg C, μ = 1.0 with KCl) is first order in proton activity and iodide concentration in the pH range 0.5-5.The solvent deuterium isotope effects for the reduction reaction vary in the range kH/kD = 0.26-0.48 as the nitrogen substituent is changed from ethyl- to trifluoroethylamine.Electron-withdrawing groups in the leaving group decrease the rate of the reaction and give βl.g. values of ca. 0.7 for cyanoethyl- and trifluoroethylamine leaving groups and ca. 0.1 for the more basic ethylamine derivatives; a βl.g. of 0.58 is observed for aniline derivatives.General acid catalysis is observed in the reduction of the acidic ethylamine and aniline derivatives with Broensted α values of 0.59 and 0.39 for cyanoethyl- and trifluoroethylamine leaving groups, respectively; for anilines, the Broensted α values decreased from 0.67 to 0.50 as the leaving group is changed from 4-methyl- to 3-nitroaniline.The value of βl.g. decreases with decreasing strength of the catalyzing acid and the term pxy = (δβl.g./δpKaHA) = (δα/δKal.g.) ca. -0.06 to -0.1.The solvent deuterium isotope effect on the general catalyzed reduction reaction increases with increasing acid strength; for the cyanoethylamine derivative, kBH/kBD = 1.47-2.32 for acetic and chloroacetic acids, respectively.A mechanism is suggested involving concurrent stepwise and concerted mechanisms for the reduction reaction; the mechanism observed seems to depend on the nature of the catalyzing acid.

Recyclable aluminium oxy-hydroxide supported Pd nanoparticles for selective hydrogenation of nitro compounds via sodium borohydride hydrolysis

G?ksu, Haydar

, p. 8498 - 8504 (2015)

The reduction of aromatic/aliphatic nitro compounds to primary amines with high yields was easily realized by transfer hydrogenation comprising commercially available aluminium oxy-hydroxide-supported Pd nanoparticles (0.5 wt% Pd, Pd/AlO(OH)) as catalysts and NaBH4 as the hydrogen reservoir at room temperature in a water/methanol mixture (v/v = 7/3). The presented catalytic methodology is highly efficient for the reduction of various nitro compounds as well as reusable. A variety of R-NO2 derivatives were tested by performing the Pd/AlO(OH) catalysed reduction reaction and all the nitro compounds were selectively reduced to their corresponding primary amines in reaction times ranging from 0.75 to 13 min with yields reaching up to 99%. This process can be assessed as an eco-friendly method involving both reusable catalysts (Pd/AlO(OH) NPs) and hydrogen sources (NaBH4).

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

Dong, Zhenhua,Pan, Hongguo,Gao, Pengwei,Xiao, Yongmei,Fan, Lulu,Chen, Jing,Wang, Wentao

, p. 299 - 306 (2021/05/10)

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.]

Rhodium nanoparticles supported on 2-(aminomethyl)phenols-modified Fe3O4 spheres as a magnetically recoverable catalyst for reduction of nitroarenes and the degradation of dyes in water

Chen, Tian,Chen, Zhangpei,Hu, Jianshe,Lv, Kexin,Reheman, Aikebaier,Wang, Gongshu

, (2021/06/18)

A magnetic nanostructured catalyst (Fe3O4@SiO2-Amp-Rh) modified with 2-(aminomethyl)phenols (Amp) was designed and prepared, which is used to catalyze the reduction of aromatic nitro compounds into corresponding amines and the degradation of dyes. The 2-aminomethylphenol motif plays a vital role in the immobilization of rhodium nanoparticles to offer extraordinary stability, which has been characterized by using various techniques, including transmission electron microscopy (TEM), thermal gravimetric analyzer (TGA), X-Ray Diffraction (XRD), and X-ray photoelectron spectroscopy (XPS). A variety of nitroaromatic derivatives have been reduced to the corresponding anilines in water with up to yields of 99% within 1?h at room temperature. In addition, the catalyst system is effective in catalyzing the reduction of toxic pollutant 4-nitrophenol and the degradation of MO, MB and RhB dyes. Importantly, this catalyst Fe3O4@SiO2-Amp-Rh can be easily recovered by an external magnetic field because of the presence of magnetic core of Fe3O4, and the activity of Fe3O4@SiO2-Amp-Rh does not decrease significantly after 7 times’ recycling, which indicates that the catalyst performed high reactivity as well as stability. Graphical abstract: [Figure not available: see fulltext.]

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