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121-69-7

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121-69-7 Usage

Chemical Properties

N,N-Dimethylaniline is a light yellow to light brown oily liquid. Has a pungent odor. Soluble in ethanol, chloroform, ether and aromatic organic solvents, slightly soluble in water.It is a tertiary amine used in the synthesis of several triarylmethane dyes like malachite green. It is also used in the synthesis of a magnetic gram stain for the detection of bacteria.

Physical properties

Straw to brown-colored oily liquid with a characteristic amine-like odor. Odor threshold concentration is 13 ppb (quoted, Amoore and Hautala, 1983).

Uses

Different sources of media describe the Uses of 121-69-7 differently. You can refer to the following data:
1. N,N-Dimethylaniline is used in production of dyestuffs, as a solvent, a reagent in methylation reactions, and a hardener in fiberglass reinforced resins.
2. N,N-dimethylaniline is an important dye intermediate. It can be used to prepare alkaline yellow, Crystal Violet 5BN, basic magenta green, basic lake blue BB, basic brilliant blue R, cationic red 2BL, brilliant red 5GN, violet 3BL, brilliant blue, etc. In the pharmaceutical industry, the product can be used to manufacture cefazolin V, sulfamonomethoxine, Sulfadoxine, fluorocytosine, etc. moreover, It can be used as an intermediate to vanillin, a stabilizer for colorimetric peroxidase determination or as a reagent in chemical synthesis.

Definition

ChEBI: N,N-dimethylaniline is a tertiary amine that is aniline in which the amino hydrogens are replaced by two methyl groups. It is a tertiary amine and a dimethylaniline.

Production Methods

N,N-Dimethylaniline is made by heating aniline, methyl alcohol and sulfuric acid under pressure, followed by hydrolysis of the sulfate formed with sodium hydroxide to the free base (Windholz et al 1983). United States production in 1975 was estimated at 4,600 metric tons (HSDB 1989).

General Description

N,N-Dimethylaniline appears as a yellow to brown colored oily liquid with a fishlike odor. Less dense than water and insoluble in water. Flash point 150°F. Toxic by ingestion, inhalation, and skin absorption. Used to make dyes and as a solvent.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Explosive decomposition occurred when finely divided benzoyl peroxide was allowed to react with N,N-Dimethylaniline by breaking an ampoule containing 0.5 grams of dimethylaniline in an autoclave, NFPA 491M, 1991. This result may be expected with other peroxides and various oxidants.

Health Hazard

Different sources of media describe the Health Hazard of 121-69-7 differently. You can refer to the following data:
1. TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
2. Clinical signs of intoxication with N,N-dimethylaniline in man are headaches, cyanosis, dizziness, labored breathing, paralysis and convulsions (HSDB 1989). It is absorbed through the skin to produce a dangerous methemoglobinemia (Gosselin 1984). Treatment is similar to that of aniline with the object of managing methemoglobinemia.

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

Flammability and Explosibility

Nonflammable

Industrial uses

N,N-Dimethylaniline is used as chemical intermediate in the manufacturing of vanillin, Michler's ketone, and dyes such as Acid Red 2, Basic Green 4 and Basic Violet 1 (Northcott 1978). It is also used as a solvent and an activator for polyesters and as an alkylating agent (Beard and Noe 1981). It is used as an acid scavenger or accepter in the manufacture of beta-lactam antibiotics such as penicillin and cephalosporin (Nachtmann and Gstrein 1981).

Safety Profile

Suspected carcinogen with equivocal tumorigenic data. Human poison by ingestion. Moderately toxic by inhalation and skin contact. A skin irritant. Human systemic effects by ingestion: nausea or vomiting. Physiological action is similar to, but less toxic than, adne. A central nervous system depressant. Mutation data reported. Flammable liquid when exposed to heat, flame, or oxidizers. Explodes on contact with benzoyl peroxide or disopropyl peroxydicarbonate. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits htghly toxic fumes of adne and NOx. See also ANILINE.

Carcinogenicity

A 2-year corn oil gavage bioassay conducted by NTP in F344/N rats (0.3 or 30 mg/kg) and B6C3F1 mice (0, 15, or 30 mg/kg) for 103 weeks concluded that there was some evidence of carcinogenic activity for male F344/N rats as indicated by the increased incidences of sarcomas or osteosarcomas in the spleen; there was no evidence of carcinogenic activity in the female rats or male mice; there was equivocal evidence of carcinogenic activity for female mice as indicated by an increased incidence of squamous cell papillomas of the forestomach. Both rats and mice could have tolerated doses higher than those used in these studies.

Environmental fate

Photolytic. A rate constant of 1.48 x 10-10 cm3/molecule?sec was reported for the reaction of N,N-dimethylaniline and OH radicals in air at room temperature (Atkinson et al., 1987). Chemical/Physical. Products identified from the gas-phase reaction of ozone with N,Ndimethylaniline in synthetic air at 23 °C were: N-methylformanilide, formaldehyde, formic acid, hydrogen peroxide, and a nitrated salt having the formula: [C6H6NH(CH3)2]+NO3 - (Atkinson et al., 1987). Reacts with acids forming water-soluble salts.

Metabolism

Ν,Ν-Dimethylaniline undergoes N-demethylation, N-oxidation, and ring hydroxylation in animals. Urinary metabolites produced by dogs and rabbits injected with this compound included 4-aminophenol, 4-dimethylaminophenol, 2-aminophenol and N-methylaniline (Williams 1959; Kiese and Renner 1974). N-oxidation, N-demethylation and ring hydroxylation of Ν,Ν-dimethylaniline was demonstrated in vitro using liver microsomal preparations from pigs, rats, rabbits, chickens, and guinea pigs (Fish et al 1955; Zeigler and Pettit 1964, 1966; Abou-Donia and Menzel 1968). N-oxidation was also demonstrated using whole homogenate of human liver (Zeigler and Gold 1971; Rane 1974). Evidence has been obtained with rabbit liver microsomes for two pathways for Ν,Ν-dimethylaniline N-oxidation (Hlavica and Kehl 1977). One pathway involves cytochrome P-450 while the second makes use of flavin-containing monooxygenase. N,N-Dimethylaniline was also metabolized to formaldehyde in the nasal and respiratory mucosa of Fischer 344 rats (McNulty et al 1983). Alveolar type II cells from rabbit and rat lungs catalyzed the N-oxidation of this compound (Devereux and Fouts 1974; Ohmiya and Mehendale 1981). The microsomal preparation from rat seminal vesicles when fortified with arachidonic acid catalyzed the dealkylation of N,Ndimethylaniline (Sivarajah et al 1982).

Purification Methods

Primary and secondary amines (including aniline and monomethylaniline) can be removed by refluxing for 4-5hours with excess acetic anhydride, and then fractionally distilling. Crocker and Jones (J Chem Soc 1808 1959) used four volumes of acetic anhydride, then distilled off the greater part of it, and dissolved the residue in ice-cold dilute HCl. Non-basic materials were removed by ether extraction, then the dimethylaniline was liberated with ammonia, extracted with ether, dried, and distilled under reduced pressure. Metzler and Tobolsky (J Am Chem Soc 76 5178 1954) refluxed with only 10% (w/w) of acetic anhydride, then cooled and poured it into excess 20% HCl, which, after cooling, was extracted with diethyl ether. (The amine hydrochloride remains in the aqueous phase.) The HCl solution was cautiously made alkaline to phenolphthalein, and the amine layer was drawn off, dried over KOH and fractionally distilled under reduced pressure, under nitrogen. Suitable drying agents for dimethylaniline include NaOH, BaO, CaSO4, and CaH2. Other purification procedures include the formation of the picrate (m 163o from Me2CO or EtOH/H2O), prepared in *benzene solution and crystallised to constant melting point, then decomposed with warm 10% NaOH and extracted into ether: the extract was washed with water and distilled under reduced pressure. The oxalate salt has also been used for purification. The base has been fractionally crystallised by partial freezing and also from aqueous 80% EtOH then from absolute EtOH. It has been distilled from zinc dust, under nitrogen. [Beilstein 12 H 141, 12 I 151, 12 II 2, 12 III 245, 12 IV 243.]

Check Digit Verification of cas no

The CAS Registry Mumber 121-69-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 1 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 121-69:
(5*1)+(4*2)+(3*1)+(2*6)+(1*9)=37
37 % 10 = 7
So 121-69-7 is a valid CAS Registry Number.
InChI:InChI=1/C8H11N/c1-9(2)8-6-4-3-5-7-8/h3-7H,1-2H3/p+1

121-69-7 Well-known Company Product Price

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  • TCI America

  • (D3866)  N,N-Dimethylaniline [for Biochemical Research]  >99.0%(GC)

  • 121-69-7

  • 1g

  • 180.00CNY

  • Detail
  • TCI America

  • (D3866)  N,N-Dimethylaniline [for Biochemical Research]  >99.0%(GC)

  • 121-69-7

  • 5g

  • 560.00CNY

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  • Alfa Aesar

  • (A11916)  N,N-Dimethylaniline, 99%   

  • 121-69-7

  • 100ml

  • 184.0CNY

  • Detail
  • Alfa Aesar

  • (A11916)  N,N-Dimethylaniline, 99%   

  • 121-69-7

  • 500ml

  • 223.0CNY

  • Detail
  • Alfa Aesar

  • (A11916)  N,N-Dimethylaniline, 99%   

  • 121-69-7

  • 2500ml

  • 706.0CNY

  • Detail
  • Alfa Aesar

  • (A11916)  N,N-Dimethylaniline, 99%   

  • 121-69-7

  • 10000ml

  • 2326.0CNY

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121-69-7SDS

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 N,N-dimethylaniline

1.2 Other means of identification

Product number -
Other names N,N-Dimethylbenzeneamine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. N,N-Dimethylaniline is used as an intermediate in the manufacture of vanillin, Michler's ketone, methyl violet, and other dyes and also as a solvent, an alkylating agent, and a stabilizer. (-,,)
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:121-69-7 SDS

121-69-7Synthetic route

4-bromo-N,N-dimethylaniline
586-77-6

4-bromo-N,N-dimethylaniline

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With 4-methyl-morpholine; tetrahydroxydiboron; 5%-palladium/activated carbon In 1,2-dichloro-ethane at 50℃; for 3h;100%
With lithium aluminium tetrahydride; di-tert-butyl peroxide In tetrahydrofuran for 3h; Irradiation;93%
With isopropyl alcohol at 20℃; for 24h; UV-irradiation; chemoselective reaction;82%
carbon dioxide
124-38-9

carbon dioxide

N-methylaniline
100-61-8

N-methylaniline

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With 9-borabicyclo[3.3.1]nonane dimer; proazaphosphatrane In tetrahydrofuran-d8 at 90℃; under 750.075 Torr; for 0.166667h; Catalytic behavior; Time; Inert atmosphere; Schlenk technique; Sealed tube; chemoselective reaction;100%
With [Ru(Triphos)(TMM)]; hydrogen; bis(trifluoromethanesulfonyl)amide In tetrahydrofuran at 150℃; under 60006 Torr; for 10h; Temperature; Time; Reagent/catalyst; Pressure; Inert atmosphere;99%
With phenylsilane; triphenylphosphine In tetrahydrofuran at 120℃; under 3750.38 Torr; for 24h; Catalytic behavior; Reagent/catalyst; Autoclave; Green chemistry;99%
(4-(N,N-dimethylamino)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
171364-78-6

(4-(N,N-dimethylamino)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With water In dimethylsulfoxide-d6 at 100℃; for 96h;100%
C13H17BN2O4

C13H17BN2O4

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With water In dimethylsulfoxide-d6 at 100℃; for 168h;100%
carbon dioxide
124-38-9

carbon dioxide

N,N’-dimethyl-N,N’-diphenylmethanediamine
1145-27-3

N,N’-dimethyl-N,N’-diphenylmethanediamine

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With potassium tungstate; phenylsilane In acetonitrile at 70℃; for 12h;100%
methanol
67-56-1

methanol

aniline
62-53-3

aniline

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With ferric(III) bromide; 1,2,3,4,5-pentamethylcyclopentadiene; Pyroglutamic acid In 1,2,4-Trimethylbenzene at 200℃; for 36h; Inert atmosphere;99%
With tetrachloromethane; copper(ll) bromide at 180℃; for 6h; Reagent/catalyst; Temperature; Inert atmosphere; Sealed tube;99%
With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine In 1,2,4-Trimethylbenzene at 200℃; for 36h; Inert atmosphere;97%
N-methyl-N-phenylformamide
93-61-8

N-methyl-N-phenylformamide

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With tris(pentafluorophenyl)borate In dibutyl ether at 100℃; for 8h; Inert atmosphere; Schlenk technique;99%
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex; 1,3-bis-(diphenylphosphino)propane; phenylsilane In dibutyl ether at 20℃; for 18h; Schlenk technique; Inert atmosphere;98%
With tetrabutyl ammonium fluoride; HSiPh3 In acetonitrile at 50℃;95%
phenyltrimethylammonium iodide
98-04-4

phenyltrimethylammonium iodide

(4-(dimethylamino)phenyl)zinc(II) chloride
93296-10-7

(4-(dimethylamino)phenyl)zinc(II) chloride

A

N,N-dimethyl-4-biphenylamine
1137-79-7

N,N-dimethyl-4-biphenylamine

B

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With bis(tricyclohexylphosphine)nickel(II) dichloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 90℃; for 8h; Negishi coupling reaction; Inert atmosphere;A 99%
B n/a
N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

chlorobenzene
108-90-7

chlorobenzene

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With NHC-Pd(II)-Im; potassium tert-butylate at 20℃; for 6h; Inert atmosphere;99%
With bis(1,5-cyclooctadiene)nickel (0); 7,9-bis(2,6-diisopropylphenyl)-7H-acenaphtho[1,2-d]imidazol-9-ium chloride; potassium tert-butylate In water; toluene at 35℃; for 24h; Catalytic behavior; Reagent/catalyst; Glovebox; Sealed tube; Inert atmosphere;99 %Chromat.
phenylsilane
694-53-1

phenylsilane

N-methyl-N-phenylformamide
93-61-8

N-methyl-N-phenylformamide

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With C27H36Cl2N2Zn at 100℃; for 20h;99%
formic acid
64-18-6

formic acid

N-methylaniline
100-61-8

N-methylaniline

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With phenylsilane In dibutyl ether at 100℃; for 8h; Catalytic behavior; Solvent; Reagent/catalyst; Inert atmosphere; Schlenk technique;99%
With phenylsilane; copper diacetate In dibutyl ether at 80℃; for 8h; Catalytic behavior; Reagent/catalyst; Schlenk technique; Green chemistry;97%
With copper (II) carbonate hydroxide; phenylsilane; 1,4-di(diphenylphosphino)-butane In acetonitrile at 60℃; for 12h;74%
carbon dioxide
124-38-9

carbon dioxide

N-methyl-N-phenylformamide
93-61-8

N-methyl-N-phenylformamide

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With phenylsilane; triphenylphosphine In tetrahydrofuran at 120℃; under 3750.38 Torr; for 24h; Autoclave; Green chemistry;99%
carbon dioxide
124-38-9

carbon dioxide

N,N’-dimethyl-N,N’-diphenylmethanediamine
1145-27-3

N,N’-dimethyl-N,N’-diphenylmethanediamine

A

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

B

N-methylaniline
100-61-8

N-methylaniline

Conditions
ConditionsYield
With diphenylsilane; cesium formate In acetonitrile at 50℃; under 750.075 Torr; Green chemistry;A 99%
B n/a
N,N-dimethylaniline N-oxide
874-52-2

N,N-dimethylaniline N-oxide

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With phenylboronic acid In dichloromethane at 20℃; for 0.0833333h;98%
With AFA In dichloromethane at 0 - 21℃;97%
With Amberlite IRA-400; borohydride form; copper(II) sulfate In methanol at 20℃; for 1h; Reduction;94%
N-methylaniline
100-61-8

N-methylaniline

A

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

B

aniline
62-53-3

aniline

Conditions
ConditionsYield
palladium at 120℃; for 20h;A 98%
B 98%
methanol
67-56-1

methanol

nitrobenzene
98-95-3

nitrobenzene

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With Raney-Ni at 169.84℃; under 22502.3 Torr; for 5h; Inert atmosphere; Autoclave;98%
With aluminum (III) chloride; water In acetonitrile at 20℃; Reagent/catalyst; Irradiation;88%
With TiO2 supported nano-Pd(0.8) catalyst In water at 20℃; for 15h; Inert atmosphere; Irradiation; Green chemistry;76 %Chromat.
With palladium 10% on activated carbon; potassium tert-butylate at 150℃; for 36h;
formaldehyd
50-00-0

formaldehyd

nitrobenzene
98-95-3

nitrobenzene

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With sodium carbonate In water; dimethyl sulfoxide at 130℃; for 15h; Schlenk technique; Sealed tube; Green chemistry;98%
With methanol; hydrogen at 79.84℃; under 9750.98 Torr; for 1.41667h; Autoclave;
phenyltrimethylammonium iodide
98-04-4

phenyltrimethylammonium iodide

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With disodium telluride In ethanol Heating;97%
With hydrogenchloride bei der Destillation;
With potassium hydroxide
Multi-step reaction with 2 steps
1: silver oxide
2: Erhitzen
View Scheme
benzyl<2-(N,N-dimethylamino)phenyl>diphenylphosphonium bromide
110698-86-7

benzyl<2-(N,N-dimethylamino)phenyl>diphenylphosphonium bromide

A

benzyldiphenylphosphine oxide
2959-74-2

benzyldiphenylphosphine oxide

B

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

C

benzene
71-43-2

benzene

Conditions
ConditionsYield
With potassium hydroxide In 1,4-dioxane; water at 37.7℃; relative rate constant; other o- and p-substituted phenyl phosphomium salts; other temperature;A 96%
B 96.5%
C 3.5%
bromobenzene
108-86-1

bromobenzene

dimethyl amine
124-40-3

dimethyl amine

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With copper(l) iodide; 6,7-dihydro-5H-quinolin-8-one oxime; potassium hydroxide In water at 85℃; for 24h; Inert atmosphere;95%
With potassium hydroxide In N,N-dimethyl-formamide at 110℃; for 18h; Buchwald-Hartwig Coupling;73%
at 250 - 260℃;
4-chloro-N,N-dimethylaniline
698-69-1

4-chloro-N,N-dimethylaniline

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With potassium tert-butylate; N,N-dimethyl-formamide at 35℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation;95%
With allyl-trimethyl-silane In cyclohexane Quantum yield; Further Variations:; Solvents; UV-irradiation;
With [hmim][ClO4] for 16h; Irradiation;78 % Chromat.
In isopropyl alcohol for 4h; Irradiation; Inert atmosphere;99 %Chromat.
With triethanolamine; water In ethanol for 24h; Irradiation; Glovebox;90 %Chromat.
formic acid
64-18-6

formic acid

nitrobenzene
98-95-3

nitrobenzene

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With hydrogen In toluene at 140℃; under 30003 Torr; for 3h; chemoselective reaction;95%
With tetrakis(triphenylphosphine)platinum; phenylsilane; C30H51Cl3Mo3N6PPtS4(1+)*BF4(1-) In tetrahydrofuran at 70℃; under 760.051 Torr; Inert atmosphere; Schlenk technique; chemoselective reaction;91%
formaldehyd
50-00-0

formaldehyd

aniline
62-53-3

aniline

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With N-methylpyrrolidine zinc borohydride; sulfuric acid In tetrahydrofuran; water at 0 - 10℃;94%
With sodium cyanoborohydride for 2h;92%
With acetic acid; zinc In 1,4-dioxane at 30℃; for 0.5h;92%
(benzyl)di(methyl)(phenyl)ammonium bromide
23145-45-1

(benzyl)di(methyl)(phenyl)ammonium bromide

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With sodium hydrogen telluride In N,N-dimethyl-formamide at 40℃; for 4h;94%
With sodium hydrogen telluride In N,N-dimethyl-formamide at 40℃; for 4h; Mechanism; other phase transfer catalysts;
lithium iodide monohydrate

lithium iodide monohydrate

4-(dimethylamino)phenylthallium bis(trifluroacetate) * 2CF3COOH

4-(dimethylamino)phenylthallium bis(trifluroacetate) * 2CF3COOH

A

thallium(III) iodide
13453-37-7

thallium(III) iodide

B

lithium trifluoroacetate
2923-17-3

lithium trifluoroacetate

C

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
In acetone -70°C, several hours, warming to room temp.; redn. of vol. (distn., vac., room temp.), pptn. on addn. of water, crystn. (overnight), dissolving (acetone), pptn. on pentane addn., crystn. (several days);A 94%
B n/a
C n/a
carbon dioxide
124-38-9

carbon dioxide

aniline
62-53-3

aniline

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With [Ru(Triphos)(TMM)]; hydrogen; bis(trifluoromethanesulfonyl)amide In tetrahydrofuran at 150℃; under 60006 Torr; for 15h; Inert atmosphere;94%
With [RhCl{κ3-P,C,P′=C(NCH2PCy2)2C10H6}]; phenylsilane In toluene at 90℃; for 16h; Schlenk technique;93%
With hydrogen In hexane at 140℃; under 15001.5 - 60006 Torr; for 7h; Inert atmosphere; Autoclave;92%
carbon dioxide
124-38-9

carbon dioxide

N-methylaniline
100-61-8

N-methylaniline

A

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

B

N-methyl-N-phenylformamide
93-61-8

N-methyl-N-phenylformamide

Conditions
ConditionsYield
With phenylsilane In N,N-dimethyl acetamide at 60℃; for 4h; Time; Sealed tube;A 94%
B 8%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 110℃; under 760.051 Torr; for 48h; Mechanism; Solvent; Reagent/catalyst; Schlenk technique;A 92%
B 8%
With phenylsilane; C23H23O2P In acetonitrile at 100℃; under 15001.5 Torr; for 24h;A 8%
B 91%
4-(dimethylamino)benzene-boronic acid
28611-39-4

4-(dimethylamino)benzene-boronic acid

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With water In dimethyl sulfoxide at 100℃; for 2h; Reagent/catalyst; Solvent; Enzymatic reaction;94%
Multi-step reaction with 2 steps
1: dimethyl sulfoxide / toluene / 0.5 h / 120 °C / Dean-Stark
2: water / dimethylsulfoxide-d6 / 168 h / 100 °C
View Scheme
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 1 h / 120 °C / Molecular sieve; Inert atmosphere
2: water / dimethylsulfoxide-d6 / 168 h / 100 °C
View Scheme
Multi-step reaction with 2 steps
1: toluene / 1 h / 20 °C / Inert atmosphere
2: water / dimethylsulfoxide-d6 / 96 h / 100 °C
View Scheme
formaldehyd
50-00-0

formaldehyd

N-methylaniline
100-61-8

N-methylaniline

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With sodium tetrahydroborate In 2,2,2-trifluoroethanol for 1.1h; Reflux;93%
Stage #1: formaldehyd; N-methylaniline With hydrogenchloride In methanol at 20℃;
Stage #2: With N-methylpiperidine zinc borohydride In methanol at 20℃; for 0.25h;
88%
With N-methylpyrrolidine zinc borohydride; sulfuric acid In tetrahydrofuran; water at 0 - 10℃; for 0.333333h;88%
N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

N,N-dimethylaniline N-oxide
874-52-2

N,N-dimethylaniline N-oxide

Conditions
ConditionsYield
With 4a-FlEt-OOH In 1,4-dioxane at 30℃; Rate constant;100%
With oxygen; ruthenium trichloride In 1,2-dichloro-ethane at 20℃; under 760 Torr; for 8h;98%
With dihydrogen peroxide In acetonitrile at 80℃; under 760.051 Torr; for 4h;98%
N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

p-N,N-dimethylaminobenzenesulfonic acid
121-58-4

p-N,N-dimethylaminobenzenesulfonic acid

Conditions
ConditionsYield
With bis(trimethylsilyl)sulphate at 170℃; for 5h;100%
Stage #1: N,N-dimethyl-aniline With bis(trimethylsilyl)sulphate at 170℃; for 4h;
Stage #2: With water
96%
With bis(trimethylsilyl)sulphate at 170℃; for 4h;85%
N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

N,N-Dimethyl-4-nitroaniline
100-23-2

N,N-Dimethyl-4-nitroaniline

Conditions
ConditionsYield
With bismuth(III) nitrate; sulfuric acid; silica gel at 25℃; for 0.0333333h;100%
With sodium nitrate In neat (no solvent) at 20℃; for 0.05h; Green chemistry;98%
With 2-chloro-1-methyl-pyridinium iodide; water; silica gel; sodium nitrite In hexane at 20℃; for 0.75h; regioselective reaction;85%
4,6-dinitrobenzofuroxan
5128-28-9

4,6-dinitrobenzofuroxan

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

4-(4-dimethylammoniophenyl)-5,7-dinitro-4,5-dihydrobenzofurazanide 3-oxide

4-(4-dimethylammoniophenyl)-5,7-dinitro-4,5-dihydrobenzofurazanide 3-oxide

Conditions
ConditionsYield
In methanol for 2h; Ambient temperature;100%
(4-Benzotriazol-1-ylmethyl-phenyl)-diethyl-amine
129075-92-9

(4-Benzotriazol-1-ylmethyl-phenyl)-diethyl-amine

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

C19H26N2
129075-94-1

C19H26N2

Conditions
ConditionsYield
In acetic acid for 3h; Heating;100%
benzoyl chloride
98-88-4

benzoyl chloride

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

methyl 5-oxopyrrolidine-2-carboxylate
4931-66-2, 54571-66-3, 64700-65-8

methyl 5-oxopyrrolidine-2-carboxylate

N-methyl-N-phenyl-benzamide
1934-92-5

N-methyl-N-phenyl-benzamide

Conditions
ConditionsYield
Product distribution;100%
N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

bis(2-amino-4-nitrophenyl) ether
515145-68-3

bis(2-amino-4-nitrophenyl) ether

4,4'-[oxobis(3-nitro-o-phenyleneazo)]bis(N,N-dimethyl-aniline)

4,4'-[oxobis(3-nitro-o-phenyleneazo)]bis(N,N-dimethyl-aniline)

Conditions
ConditionsYield
Stage #1: bis(2-amino-4-nitrophenyl) ether With hydrogenchloride; sodium nitrite at 0 - 5℃; for 1h;
Stage #2: N,N-dimethyl-aniline With hydrogenchloride In acetate buffer pH=5;
100%
N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

1-Bromo-2-bromomethyl-benzene
3433-80-5

1-Bromo-2-bromomethyl-benzene

(ortho-bromobenzyl)dimethylanilinium bromide

(ortho-bromobenzyl)dimethylanilinium bromide

Conditions
ConditionsYield
In benzene at 23℃; for 48h;100%
N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

diborane
19287-45-7

diborane

N,N-diethylaniline borane
1769-74-0

N,N-diethylaniline borane

Conditions
ConditionsYield
In toluene Product distribution / selectivity;100%
In neat (no solvent) addn. of diborane to amine at liquid N2 temp., keeping at -111°C, -78°C and 0°C consecutively, stirring at 0°C for 4-6 h (vacuum line); cooling to -78°C, removal of B2H6 by distn.;
In neat (no solvent) at 0°C;;
In neat (no solvent) at room temp.;;
[Cp*Ru(CH3CN)3]OTf
113860-02-9

[Cp*Ru(CH3CN)3]OTf

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

{C5(CH3)5}Ru{C6H5N(CH3)2}(1+)*CF3SO3(1-)={(C5(CH3)5)Ru(C6H5N(CH3)2)}(CF3SO3)

{C5(CH3)5}Ru{C6H5N(CH3)2}(1+)*CF3SO3(1-)={(C5(CH3)5)Ru(C6H5N(CH3)2)}(CF3SO3)

Conditions
ConditionsYield
In tetrahydrofuran byproducts: CH3CN; under N2; addn. of Ru-complex to N,N-dimethylaniline and THF (benzene-free), mixt. stirred (30°C); addn. of hexane, solid filtered, washed twice (hexane), dried (vac.), elem. anal.;100%
[((CH3)3CC(NC(CH3)3)2)GaCH3](1+)*[B(C6F5)4](1-)=[((CH3)3CC(NC(CH3)3)2)GaCH3][B(C6F5)4]
258519-28-7

[((CH3)3CC(NC(CH3)3)2)GaCH3](1+)*[B(C6F5)4](1-)=[((CH3)3CC(NC(CH3)3)2)GaCH3][B(C6F5)4]

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

[((CH3)3CC(NC(CH3)3)2)Ga(CH3)(N(CH3)2C6H5)](1+)*[B(C6F5)4](1-)=[((CH3)3CC(NC(CH3)3)2)Ga(CH3)(N(CH3)2C6H5)][B(C6F5)4]
258519-32-3

[((CH3)3CC(NC(CH3)3)2)Ga(CH3)(N(CH3)2C6H5)](1+)*[B(C6F5)4](1-)=[((CH3)3CC(NC(CH3)3)2)Ga(CH3)(N(CH3)2C6H5)][B(C6F5)4]

Conditions
ConditionsYield
In further solvent(s) under N2; in C6D5Cl, 23°C, 10 min; not isolated; NMR;100%
sodium cyanide
773837-37-9

sodium cyanide

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

(N-methylanilino)acetonitrile
36602-08-1

(N-methylanilino)acetonitrile

Conditions
ConditionsYield
With C47H45Cl2N5Ru2(2+)*2F6P(1-); dihydrogen peroxide; acetic acid In methanol at 60℃; for 8h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;100%
With dihydrogen peroxide; acetic acid In water at 20℃; for 0.416667h; Reagent/catalyst; Solvent;98%
With C22H26N2O5U; dihydrogen peroxide; acetic acid In methanol at 20℃; for 8h; Catalytic behavior; Reagent/catalyst; Solvent; Irradiation;97%
trifluorormethanesulfonic acid
1493-13-6

trifluorormethanesulfonic acid

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

N,N-dimethylphenylammonium trifluoromethanesulfonate
142279-32-1

N,N-dimethylphenylammonium trifluoromethanesulfonate

Conditions
ConditionsYield
In hexane at 20℃; for 1h;100%
N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

3-iodo-N,N-dimethylaniline
33454-16-9

3-iodo-N,N-dimethylaniline

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-aniline With (TMEDA)Na(TMP)(t-Bu)Zn(t-Bu) In hexane at 20℃; Inert atmosphere;
Stage #2: With iodine Inert atmosphere;
100%
N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

chromium(0) hexacarbonyl
199620-14-9, 13007-92-6

chromium(0) hexacarbonyl

(N,N-dimethylaniline)tricarbonylchromium
124916-48-9, 14122-95-3, 12109-10-3

(N,N-dimethylaniline)tricarbonylchromium

Conditions
ConditionsYield
In decalin byproducts: CO; 3.5:1 mixture of arene and Cr(CO)6 in solvent purged for 20 min with Ar, evacuated for 20 min, mixture refluxed, cooled to 20°C, cooled to -18°C under argon, reaction time 5.5 h; filtered off, dissolved in benzene, filtered through Kieselguhr, concentrated, light petroleum added, crystn. at -18°C, complexes eluted with benzene/ethyl acetate, elem. anal., NMR;99.5%
In neat (no solvent) boiling;;91%
In neat (no solvent) boiling;;91%
formaldehyd
50-00-0

formaldehyd

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

4,4'-methylene-bis(N,N-dimethylaniline)
101-61-1

4,4'-methylene-bis(N,N-dimethylaniline)

Conditions
ConditionsYield
With aluminum (III) chloride; sodium pyrophosphate; hydrazine hydrate; pyrographite; ammonium hydroxide; 1-butyl-3-methylimidazolium chloride; sodium hydroxide at 130℃; for 0.0222222h; Reagent/catalyst; Temperature;99.4%
With acetic acid; β-naphthol In ethanol at 20℃; for 12h; Mannich type Friedel-Crafts reaction;90%
With acetic acid In water82%
N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

A

2-dimethylamino-benzenesulfonic acid
14503-46-9

2-dimethylamino-benzenesulfonic acid

B

p-N,N-dimethylaminobenzenesulfonic acid
121-58-4

p-N,N-dimethylaminobenzenesulfonic acid

Conditions
ConditionsYield
With chlorosulfonic acid In 1,2-dichloro-benzene at 50℃; for 1h; Product distribution; Kinetics; Mechanism; E(activ), oth. temperatures;A 0.6%
B 99.4%
With sulfur trioxide In 1,2-dichloro-ethane at 5℃; Rate constant; Thermodynamic data; Product distribution; oth. temperature, E(activ.), var. ratios of reactants;
With sulfuric acid In 1,2-dichloro-benzene at 180℃; Kinetics; Thermodynamic data; Equilibrium constant; variation of molar ratio and temperature, Ea, ΔGo, ΔHo, ΔSo;
With sulfuric acid In 1,2-dichloro-benzene at 24.9℃; Thermodynamic data; Mechanism; Activation Free Energy, Enthalpy, Entropy of sulfonation and desulfonation;
N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

4-amino-3-nitrobenzoic acid
1588-83-6

4-amino-3-nitrobenzoic acid

4'-dimethylamino-2-nitroazobenzene-4-carboxylic acid
392300-99-1

4'-dimethylamino-2-nitroazobenzene-4-carboxylic acid

Conditions
ConditionsYield
Stage #1: 4-amino-3-nitrobenzoic acid With hydrogenchloride; sodium nitrite In water; acetic acid at 15 - 20℃; for 0.25h;
Stage #2: N,N-dimethyl-aniline In water; acetic acid at 0 - 5℃;
99.4%
ethenetetracarbonitrile
670-54-2

ethenetetracarbonitrile

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

2-(4-dimethylaminophenyl)ethylene-1,1,2-tricarbonitrile
6673-15-0

2-(4-dimethylaminophenyl)ethylene-1,1,2-tricarbonitrile

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20 - 25℃; for 0.0833333h; Sonication;99%
In N,N-dimethyl-formamide at 50 - 60℃; for 0.5h;95%
With choline chloride; urea at 35℃; for 0.0833333h; Reagent/catalyst; Solvent; Green chemistry;89%
With N,N-dimethyl-formamide
In N,N-dimethyl-formamide
allyl iodid
556-56-9

allyl iodid

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

N-allyl-N,N-dimethylbenzenaminium iodide
73680-59-8

N-allyl-N,N-dimethylbenzenaminium iodide

Conditions
ConditionsYield
at 30℃;99%
N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

4-bromo-N,N-dimethylaniline
586-77-6

4-bromo-N,N-dimethylaniline

Conditions
ConditionsYield
With methanol; tetraethylammonium chloride; bromine In dichloromethane at 35℃; other substituted anilines: regioselectivity of bromination;99%
With methanol; tetraethylammonium chloride; bromine In dichloromethane at 35℃;99%
With hexabromocyclopenta-1,3-diene; triethylamine In acetonitrile for 24h; Ambient temperature;99%
N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

4-Iodo-N,N-dimethylaniline
698-70-4

4-Iodo-N,N-dimethylaniline

Conditions
ConditionsYield
With iodine at 30℃; for 12h; Green chemistry;99%
With tetrafluoroboric acid; [bis(pyridine)iodine]+ tetrafluoroborate In diethyl ether; dichloromethane for 0.1h; Ambient temperature;98%
With iodine In 1,4-dioxane; pyridine at 0 - 20℃;98%
N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

N,N-Dimethylaniline hydroiodide
35462-54-5

N,N-Dimethylaniline hydroiodide

Conditions
ConditionsYield
With hydrogen iodide In 1,4-dioxane; water at 0 - 20℃; for 12h;99%
With hydrogen iodide

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The reaction of lithiated N,N-dimethylaniline π-coordinated to Cr(CO)3 with W(CO)6 and alkylation with [Et3O][BF4] afforded the o-, m- and p-isomers of the σ,π-bimetallic complexes {η6-Me2NC6H4C(OEt)W(CO)5}Cr(CO)3 (o-, 1, m-, 2 and p-isomer, 3). A by-product of the reaction is found by the s...detailed

Determination of thermodynamic properties for protonation equilibrium between isomeric cresols and N,N-Dimethylaniline (cas 121-69-7) in n-hexane medium09/10/2019

The formation of hydrogen bonded complexes of o-cresol (OC), m-cresol (MC) and p-cresol (PC) with N,N-dimethylaniline (DMA) in n-hexane solutions is investigated by ultrasonic velocity, density and dynamic viscosity measurements in the equimolar concentration of solutes ([cresol] = [DMA]) rangin...detailed

Volumetric and transport properties of binary liquid mixtures of sulfolane with aniline, N,N-Dimethylaniline (cas 121-69-7) and N,N-diethylaniline at different temperatures and atmospheric pressure09/08/2019

Densities and viscosities of pure sulfolane, aniline, N,N-dimethylaniline, N,N-diethylaniline and their binary mixtures with sulfolane as common component were measured over the entire composition range at T = (303.15, 308.15, and 313.15) K and atmospheric pressure. A high precision vibrating-tu...detailed

Excess molar volumes and viscosity behaviour of binary mixtures of aniline/or N,N-Dimethylaniline (cas 121-69-7) with imidazolium ionic liquids having triflate or bistriflamide anion09/07/2019

In this study, densities and viscosities of four binary systems {aniline/N,N-dimethylaniline + 1-butyl-3-methylimidazolium triflate ([bmim][OTf])} and {aniline/N,N-dimethylaniline + 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([bmim][NTf2])} were measured at atmospheric pressur...detailed

121-69-7Relevant articles and documents

Fluoro-functionalized polymeric N-heterocyclic carbene-zinc complexes: Efficient catalyst for formylation and methylation of amines with CO2 as a C1-building block

Yang, Zhen-Zhen,Yu, Bo,Zhang, Hongye,Zhao, Yanfei,Ji, Guipeng,Liu, Zhimin

, p. 19613 - 19619 (2015)

A fluoro-functionalized polymeric N-heterocyclic carbene (NHC)-Zn complex (F-PNHC-Zn) was designed and synthesized by taking fluorous imidazolium salts as precursors through a two-step alkylation. The resultant F-PNHC-Zn was applied in catalyzing the formylation and methylation of amines using CO2 as a C1 building block in the presence of organosilane, which showed much higher activity than the corresponding non-fluorous PNHC-Zn under identical conditions. N-Methylanilines with both electron-withdrawing and electron-donating groups all could be converted to the corresponding formamides and methylamines in >90% conversion. Quantitative conversion of N-methylaniline was obtained even under very low CO2 pressure (0.05 MPa diluted by N2). Moreover, F-PNHC-Zn was highly stable and easily recyclable for these reactions. This journal is

-

Merz,Weith

, p. 1571,1576 (1886)

-

Photoinduced, ionic Meerwein arylation of olefins

Mella,Coppo,Guizzardi,Fagnoni,Freccero,Albini

, p. 6344 - 6352 (2001)

Irradiation of 4-chloroaniline or of its N,N-dimethyl derivative in polar solvents generates the corresponding triplet phenyl cations. These are trapped by alkenes yielding arylated products in medium to good yields. B3LYP calculations show that the triplet cation slides with negligible activation energy to a bonded adduct with ethylene, whereas it forms only a marginally stabilized CT complex with water (chosen as a representative σ nucleophile). The structure of the final products depends on the preferred path from the adduct cation with the alkene. In the case of aryl olefins, this deprotonates to stilbene derivatives, while, from 2,3-dimethyl-2-butene and allytrimethylsilane, allylanilines are obtained by elimination of an electrofugal group in γ. In the case of mono- and disubstituted alkenes the cation adds chloride rather than eliminating and β-chloroalkylanilines are obtained. The regio- and sterochemistry of the addition across the alkene are best understood with a phenonium ion structure for the adduct. The nucleophile entering in fi can be varied under conditions in which the adduct cation is trapped more efficiently than the starting phenyl cation. Thus, β-methoxyalkylanilines are formed when the irradiation is carried out in methanol. β-Iodoalkylanilines are obtained in acetonitrile containing iodide and unsubstituted alkylanilines in the presence of sodium borohydride. A case of intramolecular nucleophilic trapping is found with 4-pentenoic acid. The reaction is a wide-scope ionic analogue of the radicalic Meerwin arylation of olefins.

Interaction of retinoic acid radical cation with lysozyme and antioxidants: Laser flash photolysis study in microemulsion

Li, Kun,Wang, Mei,Wang, Ting,Sun, Dongmei,Zhu, Rongrong,Sun, Xiaoyu,Wu, Xianzheng,Wang, Shi-Long

, p. 1064 - 1070 (2013)

All-trans retinoic acid (ATRA) plays essential roles in the normal biological processes and the treatment of cancer and skin diseases. Considering its photosensitive property, many studies have been focused on the photochemistry of ATRA. In this study, we investigated the transient phenomena in the laser flash photolysis (LFP) of ATRA in microemulsion to further understand the photochemistry of ATRA. Results show that 355 nm LFP of ATRA in both acidic and alkaline conditions leads to the generation of retinoic acid cation radicals (ATRA?+) via biphotonic processes. The employment of microemulsion system allows us to investigate the reaction of hydrophobic ATRA?+ with molecules of different polarity. Therefore, we studied the reaction activity of ATRA?+ to many hydrophobic and hydrophilic molecules. Results show that ATRA?+ can efficiently interact with lysozyme, tyrosine, tryptophan and many antioxidants, such as curcumin (Cur), vitamin C (VC) and gallic acid (GA). The apparent rate constants of these reactions were measured and compared. These findings suggest that ATRA?+ is a reactive transient product which may pose damage to lysozyme, and antioxidants, such as Cur, VC and GA, may inactivate ATRA?+ by efficient quenching reactions. 355 nm laser flash photolysis of all-trans retinoic acid (ATRA) in microemulsion leads to the formation of retinoic acid cation radicals (ATRA?+) via biphotonic processes. Deprotonated form of ATRA is more favorable for the formation of ATRA?+. ATRA?+ is proved to be reactive to lysozyme, tyrosine and tryptophan which is suggestive of its destructive effect on proteins. Meanwhile, some antioxidants, such as curcumin, gallic acid and vitamin C, can efficiently interact with ATRA?+, which indicates that it may competitively protect proteins from the attack of ATRA?+ by inactivating free radical.

Capillary-Bound Dense Micelle Brush Supports for Continuous Flow Catalysis

Cai, Jiandong,Cui, Yan,Lin, Geyu,Liu, Qiuwen,Manners, Ian,Qiu, Huibin,Sun, Yan

, p. 24637 - 24643 (2021)

Flow reactors are appealing alternatives to conventional batch reactors for heterogeneous catalysis. However, it remains a key challenge to firmly immobilize the catalysts in a facile and flexible manner and to simultaneously maintain a high catalytic efficiency and throughput. Herein, we introduce a dense cylindrical micelle brush support in glass capillary flow reactors through a living crystallization-driven self-assembly process initiated by pre-immobilized short micelle seeds. The active hairy corona of these micellar brushes allows the flexible decoration of a diverse array of nanocatalysts, either through a direct capture process or an in situ growth method. The resulting flow reactors reveal excellent catalytic efficiency for a broad range of frequently utilized transformations, including organic reductions, Suzuki couplings, photolytic degradations, and multistep cascade reactions, and the system was both recyclable and durable. Significantly, this approach is readily applicable to long capillaries, which enables the construction of flow reactors with remarkably higher throughput.

On the mechanism of the N,N-dimethyl amination of Grignard reagents: A kinetic study

Erdik, Ender,Uelhue, Selma Ates

, p. 671 - 676 (2007)

A direct kinetic study is reported for the electrophilic amination of substituted phenylmagnesium bromides with N,N-dimethyl O-(mesitylenesulfonyl) hydroxylamine in THF. Rate data, Hammett relationship, and activation entropy are consistent with a SN2 displacement involving the attack of carbanions to sp3N in the amination reagent (AR). Copyright

Brown et al.

, p. 1193,1196 (1978)

A novel access to 3-aryl-2-norbornyl cation

Mella, Mariella,Esposti, Silvia,Fagnoni, Maurizio,Albini, Angelo

, p. 738 - 739 (2003)

A novel access to a 2-norbornyl cation under mild, non acidic conditions is found in the addition of photochemically generated 4-dimethylaminophenyl cation to 2-norbornene. Deprotonation to nortricyclene or nucleophile addition ensue depending on the solvent characteristics.

-

Biehl et al.

, p. 2454 (1970)

-

Efficient degradation of azo dyes using Ag and Au nanoparticles stabilized on graphene oxide functionalized with PAMAM dendrimers

Rajesh, Rajendiran,Kumar, S. Senthil,Venkatesan, Rengarajan

, p. 1551 - 1558 (2014)

Herein, we report the stabilization of silver and gold nanoparticles (Ag/Au NPs) on graphene oxide (GO) functionalized with PAMAM dendrimers. The grafting of the PAMAM dendrimers on GO has been investigated using TGA and Raman spectral studies and the stabilization of the Ag/Au NPs on the dendritic structures has been confirmed using XRD, UV-Vis and FT-IR spectra, SEM and TEM studies. The catalytic activity of the prepared nanocatalysts towards the degradation of organic azo dyes, namely methyl orange and congo red, has been tested. The prepared nanocatalysts were found to exhibit excellent catalytic activity towards the complete degradation of both methyl orange and congo red within only a few seconds.

Visible-Light-Induced C(sp2)-C(sp3) Cross-Dehydrogenative-Coupling Reaction of N-Heterocycles with N-Alkyl- N-methylanilines under Mild Conditions

Zhang, Hong-Yu,Chen, Jianjun,Lu, Cong-Cong,Han, Ya-Ping,Zhang, Yuecheng,Zhao, Jiquan

, p. 11723 - 11735 (2021)

Disclosed herein is a cross-dehydrogenative-coupling reaction of N-heterocycles including 1,2,4-triazine-3,5(2H, 4H)-diones and quinoxaline-2(1H)-ones with N-methylanilines to form C(sp2)-C(sp3) under visible-light illumination and ambient air at room temperature. In this process, easily available Ru(bpy)3Cl2·6H2O serves as the catalyst, and air acts as the green oxidant. This method features high atom economy, environmental friendliness, and convenient operation and provides an efficient and practical access to aminomethyl-substituted N-heterocycles with extensive functional group compatibility in 40-86% yields.

-

Dunlop,Jones

, p. 416 (1909)

-

-

Tarbell,Vaughan

, p. 231 (1943)

-

REVERSIBLE PROTON TRANSFER IN THE 2,3,5,6-TETRACHLOROPHENOL-N,N-DIMETHYLANILINE HYDROGEN-BONDED COMPLEX STUDIED BY LOW-TEMPERATURE 1H NMR SPECTROSCOPY

Ilczyszyn, Marek,Ratajczak, Henryk,Ladd, John A.

, p. 499 - 504 (1989)

Low temperature 1H NMR studies of the bridging OHN signal in the hydrogen-bonded complex formed between 2,3,5,6-tetrachlorophenol and N,N-dimethylaniline in C2H5Cl solution have shown that separate signals for the molecular and ion-pair forms of the complex can be observed below -135 deg C (138 K).Analyses of the observed lineshapes have yielded values for the thermodynamic quantities ΔH0, ΔS0 as well as for the activation quantities ΔH, ΔS.

Zn(ii)@TFP-DAQ COF: An efficient mesoporous catalyst for the synthesis of: N -methylated amine and carbamate through chemical fixation of CO2

Sarkar, Priyanka,Chowdhury, Arpita Hazra,Riyajuddin, Sk.,Biswas, Surajit,Ghosh, Kaushik,Islam, Sk. Manirul

, p. 744 - 752 (2020)

Selective N-methylation and carbamate formation reactions were demonstrated via the chemical incorporation of CO2 using a Zn-loaded TFP-DAQ COF (covalent organic framework) as an active catalyst under mild reaction conditions. The selective N-methylation and N-formylation reactions were performed by simply varying the type of solvent. The Zn(ii)@TFP-DAQ COF catalyst was characterized via different characterization techniques such as PXRD, FTIR, UV-vis, N2 adsorption-desorption studies, FESEM and TEM. The catalyst material showed pores in the mesoporous region with a high surface area of 1117.375 m2 g-1. The as-synthesized material was applied as a cheap catalyst for the N-methylation of secondary amines and in carbamate formation reactions with high yields of the desired products up to 98.5% and 97%, respectively, with >99% selectivity. The catalyst was found to be completely heterogeneous and reusable for multiple reaction cycles.

The reaction between sodium hydrogen telluride and phase transfer catalysts

Li,Zhou

, p. 3635 - 3639 (1995)

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Yamdagni,R.,Kebarle,P.

, p. 3504 - 3510 (1973)

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Unexpected Macrocyclic Multinuclear Zinc and Nickel Complexes that Function as Multitasking Catalysts for CO2 Fixations

Takaishi, Kazuto,Nath, Bikash Dev,Yamada, Yuya,Kosugi, Hiroyasu,Ema, Tadashi

, p. 9984 - 9988 (2019)

Unique self-assembled macrocyclic multinuclear ZnII and NiII complexes with binaphthyl-bipyridyl ligands (L) were synthesized. X-ray analysis revealed that these complexes consisted of an outer ring (Zn3L3 or Ni3L3) and an inner core (Zn2 or Ni). In the ZnII complex, the inner Zn2 part rotated rapidly inside the outer ring in solution on an NMR timescale. These complexes exhibited dual catalytic activities for CO2 fixations: synthesis of cyclic carbonates from epoxides and CO2 and temperature-switched N-formylation/N-methylation of amines with CO2 and hydrosilane.

N-Mannich Bases of Aromatic Heterocyclic Amides: Synthesis via Copper-Catalyzed Aerobic Cross-Dehydrogenative Coupling under Ambient Conditions

Singh, Shailendra K.,Chandna, Nisha,Jain, Nidhi

, p. 1322 - 1325 (2017)

An efficient and facile method to synthesize N-Mannich bases has been developed using an inexpensive copper(I) bromide/air catalyst system at ambient temperature. A cross-dehydrogenative coupling of N,N-dimethylarylamines occurs efficiently with aromatic heterocyclic amides (oxindoles, isatins), cyclic amides (lactams), simple amides (benzamide), as well as imides (succinimide, phthalimide) to furnish the corresponding amidated/imidated derivatives in good to excellent yields. Preliminary mechanistic and isotope-labeling studies suggest the reaction follows a radical pathway and involves an iminium ion intermediate.

Kinetics of One-Electron Transfer Reactions Involving ClO2 and NO2

Huie, Robert E.,Neta, P.

, p. 1193 - 1198 (1986)

Rate constants for the one-electron oxidation of ClO2(1-) and NO2(1-) by several organic and inorganic free radicals have been measured along with rate constants for several reactions of ClO2, NO2 and BrO2.The kinetics of the reactions of ClO2 and NO2 are consistent with simple electron-transfer theory, except for the reaction of NO2 with SO3(2-), which appears to be oxygen atom transfer.Equilibrium constants have been determined for the reactions of ClO2 with aniline at pH 6.9 and N,N-dimethylaniline at pH 9.6.This leads to one-electron redox potentials of 1.03 and 0.87 V for these aromatic amines, respectively, at the corresponding pH.

N, N -Dimethylation of nitrobenzenes with CO2 and water by electrocatalysis

Sun, Xiaofu,Zhu, Qinggong,Hu, Jiayin,Kang, Xinchen,Ma, Jun,Liu, Huizhen,Han, Buxing

, p. 5669 - 5674 (2017)

We have proposed a strategy for the synthesis of N,N-dimethylanilines from nitrobenzene and its derivatives, CO2, and water via an electrochemical reaction under ambient conditions. H+ generated from H2O was used as the hydrogen source. Pd/Co-N/carbon, in which the Pd nanoparticles were supported on Co-N/carbon, was designed and used as the electrocatalyst. It was found that the electrocatalyst was very efficient for the reaction in MeCN solution with 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([Bmim]Tf2N) as the supporting electrolyte and 1-amino-methylphosphonic acid (AMPA) as the thermal co-catalyst. A series of control experiments showed that Pd/Co-N/carbon and AMPA cooperated very well in accelerating the reaction. This synthetic route has some obvious advantages, such as using CO2 and water as the reactants, ambient reaction conditions, and high yields of the desired products. This opens up a way to synthesize chemicals by the combination of an electrocatalyst and a thermal catalyst with organic compounds, CO2, and water as the reactants.

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Giumanini,Lercker

, p. 3756,3757 (1970)

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Billman,Radike,Mundy

, p. 2978 (1942)

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Highly efficient and simultaneous catalytic reduction of multiple dyes using recyclable RGO/Co dendritic nanocomposites as catalyst for wastewater treatment

Sahoo, Prasanta Kumar,Thakur, Dinbandhu,Bahadur,Panigrahy, Bharati

, p. 106723 - 106731 (2016)

Development of a low cost, highly efficient and easily retrievable catalyst with improved reusability is a major challenge in the area of advanced catalysts. In this study, we report a simple one-step approach for the fabrication of a reduced graphene oxide (RGO)/Co dendritic nanocomposite. The structure and morphology of the as synthesized material are thoroughly examined by XRD, Raman, FTIR, TEM, and SEM. The magnetic properties of the RGO/Co dendritic nanocomposite reveal that it exhibits ferromagnetic behavior at room temperature with high saturation magnetization. The catalytic activity of the RGO/Co dendritic nanocomposite was investigated for the reduction of different dyes namely, 4-nitrophenol, methylene blue, methyl orange and rhodamine B individually, and their mixture in the presence of a sufficient amount of NaBH4. RGO/Co dendritic nanocomposite exhibits excellent catalytic activity as compared to the bare Co dendritic structure. The catalyst could be easily separated by an external magnet and recycled magnetically with no major loss of catalytic activity upto five cycles. The high catalytic efficiency, low cost and easy recycle technique make RGO/Co dendritic nanocomposite a proficient catalyst for degradation of organic dyes.

Green and chemo selective amine methylation using methanol by an organometallic ruthenium complex

Abbasi, Alireza,Dindar, Sara,Nemati Kharat, Ali

, (2021/11/16)

Herein a green and convenient catalytic N-methylation of aniline and n-hexylamine using methanol as a dual methylation agent and solvent has been investigated. A new ruthenium carbonyl complex was synthesized and applied as a homogeneous catalyst in methylation reaction. The solid-state structure of the complex was determined by X-ray crystallographic analysis which indicate xantphos ligand bonded to ruthenium (II) as a tridentate pincer ligand by two P donor and one O atom. The catalytic system showed excellent conversion and selectivity toward N-methylaniline, and N,N-hexyldimethylamine at 140°C.

Efficient base-free hydrodehalogenation of organic halides catalyzed by a well-defined diphosphine-ruthenium(II) complex

Gao, Pengxiang,Liu, Qingbin,Liu, Yahuan,Ma, Ning,Wang, Zheng,Zhao, Ziwei

, (2021/10/29)

A base-free, robust catalytic system based on the diphosphine-ruthenium(II) complex cation has been developed for the hydrodehalogenation of a wide range of aryl- and alkyl-chlorides/bromides (27 examples) with molecule hydrogen. Notably, the reaction proceeds at 120 °C with low catalyst loading (0.1 mol%) and exhibits a good tolerance toward functional groups, such as amido, carboxyl, sulfonyl, methoxyl, ester groups. All dehalogenation products are confirmed by GC, GC–MS and NMR spectroscopy. Moreover, a mechanism for the diphosphine-ruthenium(II) complex cation catalyzed dehalogenation process has been proposed. This hydrodehalogenation methodology shows a potential application for the organic transformation and degradation of organic halides.

Method for realizing N-alkylation by using alcohols as carbon source under photocatalysis

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Paragraph 0048-0099, (2021/03/13)

The invention discloses a method for realizing N-alkylation by using alcohols as a carbon source under photocatalysis, and belongs to the technical field of catalytic synthesis. Alcohol, a substrate raw material and a catalyst are placed in a reaction device, ultraviolet and/or visible light irradiation is carried out in an inert atmosphere, after the irradiation is finished, solid-liquid separation is carried out to remove the catalyst, and an N-alkylation product can be obtained through extraction, distillation and purification, wherein the substrate raw material comprises any one of an amine compound, an aromatic nitro compound or an aromatic nitrile compound, the alcohol comprises any one or more of soluble primary alcohols, and the catalyst is metal oxide/titanium dioxide or metal sulfide/titanium dioxide. The method is simple and easy to operate, can be used for efficient photocatalysis one-pot multi-step hydrogenation N-alkylation reaction, and is mild in reaction condition, high in chemical selectivity of N-alkylamine, good in catalyst stability and easy to recycle.

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