611-74-5

Basic information

• Product Name: N,N-Dimethylbenzamide
• Synonyms: N,N-DiMethylbenzaMide;BenzaMide,N,N-diMethyl-;N,N-Dimethylbenzamide;Dimethylbenzamide;Dimethylbenzmide;n,n-dimethyl-benzamid;LABOTEST-BB LT00793055;N,N-DIMETHYLBENZAMIDE
• CAS NO: 611-74-5
• Molecular Formula: C₉H₁₁NO
• Molecular Weight: 149.19
• EINECS: 210-279-2
• Product Categories: AMIDE;Amides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 611-74-5.mol
• Article Data: 215

Chemical Properties

• Melting Point: 43-45 °C(lit.)
• Boiling Point: 132-133 °C15 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: white to off-white crystals.
• Density: 1.0753 (rough estimate)
• Vapor Pressure: 0.0157mmHg at 25°C
• Refractive Index: 1.5279 (estimate)
• Storage Temp.: 2-8°C(protect from light)
• PKA: -1.14±0.70(Predicted)
• Water Solubility: Soluble in water.
• BRN: 774955
• CAS DataBase Reference: N,N-Dimethylbenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Dimethylbenzamide(611-74-5)
• EPA Substance Registry System: N,N-Dimethylbenzamide(611-74-5)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: CV4500000
• TSCA: Yes
• Hazardous Substances Data: 611-74-5(Hazardous Substances Data)

Usage

Chemical Properties

white to slightly yellow cryst. low melting solid

Uses

Reagent for deoxygenation of secondary alcohols.

Synthesis Reference(s)

The Journal of Organic Chemistry, 36, p. 2721, 1971 DOI: 10.1021/jo00817a036Journal of the American Chemical Society, 77, p. 1114, 1955 DOI: 10.1021/ja01610a010Synthetic Communications, 12, p. 989, 1982 DOI: 10.1080/00397918208061938

General Description

N,N-Dimethylbenzamide is a hydrotropic agent and its ability to solubilize drugs with low aqueous solubility has been investigated. It reacts with PhLnI complexes (Ln-Eu, Sm, Yb) to yield benzophenone in good yields. Deuterium exchange labelling experimets on N,N-dimethylbenzamide using [IrH2(Me2CO)2(PPh3)2]BF4 as catalyst and deuterium gas as the source of isotope has been conducted.

InChI:InChI=1/C9H11NO/c1-10(2)9(11)8-6-4-3-5-7-8/h3-7H,1-2H3

Synthetic route

benzoic acid methyl ester (93-58-3) + methylchloroaluminum N,N-dimethylamide (84738-97-6) → N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
In benzene for 12h; Heating;	100%

N,N-dimethylthiobenzamide (15482-60-7) → N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
With 6H(1+)*Mo9O40PV3(6-); oxygen In acetonitrile at 90℃; under 760.051 Torr; for 2h; Inert atmosphere; Glovebox;	99%
With hydrogenchloride; N-nitrosopiperidine; potassium iodide In dichloromethane; water at 22℃; for 50h;	94%
With hydrogenchloride; sodium nitrite In water at 20℃; for 0.5h;	94%

tris(dimethylamino)borane (4375-83-1) + benzaldehyde (100-52-7) → N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
With tert.-butylhydroperoxide In acetonitrile at 80℃; for 24h;	99%

N,N-dimethyl-formamide (68-12-2, 33513-42-7) + benzoic acid (65-85-0) → N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
With tert.-butylhydroperoxide; copper(II) oxide In water at 80℃; for 20h; Catalytic behavior;	99%
With tert.-butylhydroperoxide; copper(II) perchlorate hexahydrate at 100℃; for 15h;	90%
With trichlorophosphate at 120℃; for 1h; Sealed tube;	90%

dimethylamine borane (74-94-2) + benzoic acid (65-85-0) → N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene for 12h; Reflux;	99%

benzoyl chloride (98-88-4) → 2,4,6-Triphenyl-thiopyrylium-chlorid (2930-27-0) + N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
With 2-Dimethylamino-2,4,6-triphenyl-2H-thiopyran In diethyl ether for 1h; Heating;	A 98% B 40%

2-Dimethylamino-2,4,6-triphenyl-2H-thiopyran (87691-75-6) → 2,4,6-Triphenyl-thiopyrylium-chlorid (2930-27-0) + N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
With benzoyl chloride In diethyl ether for 1h; Heating;	A 98% B 40%

dimethyl amine (124-40-3) + benzoic acid (65-85-0) → N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; (bis-(2-methoxyethyl)amino)sulfur trufluoride In dichloromethane at 0℃; for 0.5h;	98%
With tetrabutylammomium bromide; iodine; potassium hydroxide In water at 20℃; for 2.5h; Irradiation;	75%
With dichloro(dimethylglyoxime)(dimethylglyoximato)cobalt(III); [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; triphenylphosphine In dichloromethane at 20℃; for 12h; Inert atmosphere; Sealed tube; Irradiation;	74%
Stage #1: dimethyl amine; benzoic acid at 60℃; Autoclave; Cooling with dry ice; Stage #2: at 290℃; under 22502.3 Torr; for 0.0136111h; Microwave irradiation;

bromobenzene (108-86-1) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
With sodium methylate; nickel diacetate In 1,4-dioxane at 110℃;	98%
Stage #1: N,N-dimethyl-formamide With 1,3,5-trichloro-2,4,6-triazine at 20℃; for 1h; Stage #2: bromobenzene With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate In N,N-dimethyl-formamide at 120℃; for 6h;	81%
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; trichlorophosphate at 165℃; for 24h; Inert atmosphere;	72%

iodobenzene (591-50-4) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
With Pd nanoparticles supported on reduced graphene oxide nanosheets at 200℃; for 6h; Temperature; Concentration; Autoclave;	98%
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; trichlorophosphate at 135℃; for 6h; Inert atmosphere;	93%
Stage #1: N,N-dimethyl-formamide With tungsten(VI) chloride at 20℃; for 0.25h; Inert atmosphere; Stage #2: iodobenzene With palladium dichloride at 140℃; for 5h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere;	93%

N,N-dimethylbenzamide dimethyl acetal (35452-04-1) → 2-(trichloromethyl)-4-(dimethylamino)-4-phenyl-1,3-diaza-1,3-butadiene + N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
With trichloroacetamidine In tetrahydrofuran at 40 - 50℃; for 3h; Title compound not separated from byproducts;	A 96% B 5%

N,N-dimethylbenzamide dimethyl acetal (35452-04-1) + trichloroacetamidine (2533-68-8) → 2-(trichloromethyl)-4-(dimethylamino)-4-phenyl-1,3-diaza-1,3-butadiene + N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
In tetrahydrofuran at 40 - 50℃; for 3h; Title compound not separated from byproducts;	A 96% B 5%

tert-butyl benzoyl(phenyl)carbamate (101137-69-3) + dimethyl amine (124-40-3) → N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
With triethylamine In dichloromethane at 23℃; for 15h; Inert atmosphere; Schlenk technique;	96%

1,3-diphenylpropanedione (120-46-7) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
With iodosylbenzene at 25℃; for 24h;	96%

benzoyl chloride (98-88-4) + dimethyl amine (124-40-3) → N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; Inert atmosphere;	95%
With triethylamine In dichloromethane at 0 - 20℃;	93%
With dmap; triethylamine In tetrahydrofuran; dichloromethane at 0 - 20℃; for 12h;	91%

1-(benzoyl)piperidine-2,6-dione + dimethyl amine (124-40-3) → N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
With triethylamine In dichloromethane at 23℃; for 15h; Inert atmosphere; Schlenk technique;	95%

N,N-phenyl-p-toluenesulfonylbenzamide (74542-54-4) + dimethyl amine (124-40-3) → N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
With triethylamine In dichloromethane at 23℃; for 15h; Inert atmosphere; Schlenk technique;	94%

2-bromo-N,N-dimethyl benzamide (54616-47-6) → N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; potassium tert-butylate; isopropyl alcohol at 100℃; Schlenk technique; Inert atmosphere;	93%

dimethyl amine (124-40-3) + polymer-bound mixed benzoic dithiocarbamic anhydride → N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
In chloroform for 1h;	92%

N,N-dimethyl-formamide (68-12-2, 33513-42-7) + acetophenone (98-86-2) → N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
With sodium iodide In dimethyl sulfoxide at 20℃; for 6h; Solvent; Reagent/catalyst; Electrochemical reaction;	92%

benzoyl chloride (98-88-4) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
With dysprosium at 20℃; for 0.333333h; Inert atmosphere;	91%
Stage #1: N,N-dimethyl-formamide With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.25h; Schlenk technique; Stage #2: benzoyl chloride In tetrahydrofuran at 50℃; for 12h;	84%

benzoyl chloride (98-88-4) + 2-Dimethylamino-3-methyl-2,4,6-triphenyl-2H-pyran (79962-35-9) → 3-Methyl-2,4,6-triphenylpyryliumchlorid (92919-44-3) + N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
In diethyl ether for 1h; Heating;	A 91% B 54%

2-Dimethylamino-3-methyl-2,4,6-triphenyl-2H-pyran (79962-35-9) → 3-Methyl-2,4,6-triphenylpyryliumchlorid (92919-44-3) + N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
With benzoyl chloride In diethyl ether for 1h; Heating;	A 91% B 54%

dimethyl amine (124-40-3) + benzyl alcohol (100-51-6) → N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
With oxygen; sodium hydroxide In water at 25℃; for 24h; Green chemistry;	91%
With oxygen; sodium hydroxide In water at 25℃; for 24h;	90%
With tert.-butylhydroperoxide; [bis(acetoxy)iodo]benzene In acetonitrile Reagent/catalyst; Solvent; Reflux;	86%

benzaldehyde (100-52-7) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
With tert.-butylhydroperoxide; iodine at 70 - 80℃; for 24h;	91%
With hydrogenchloride; tert.-butylhydroperoxide; iodine In cyclohexane; water at 80℃;	88%
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide at 80℃; for 24h;	85%

2-formylbenzoyl(N,N-dimethyl)amine → N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
With (R)-(+)-2,2'-bis[bis(3,5-dimethylphenyl)phosphino]-1,1'-binaphthyl; bis(1,5-cyclooctadiene)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate In tetrahydrofuran at 135℃; for 24h; Reagent/catalyst; Sealed tube; Inert atmosphere;	91%

tetrakis(dimethylamino)silane (1624-01-7) + benzaldehyde (100-52-7) → N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
bis(di-tert-butylphosphinous acid)PdCl2 In acetonitrile at 25℃; for 24h;	90%

Benzotrichlorid (98-07-7) + dimethyl amine (124-40-3) → N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
In methanol at 20℃; for 3h; UV-irradiation;	90%

N-methylbenzamide (88070-48-8) + tetramethylammonium fluoride (373-68-2) → N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
In toluene at 100℃; for 12h;	90%

benzoyl cyanide (613-90-1) + Bis(dimethylamino)acetonitrile (2214-82-6) → N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
In N,N-dimethyl-formamide	88%

benzylpentacarbonylmanganese + N,N-dimethylbenzamide (611-74-5) → (η2-O,C-1-(N,N-dimethylaminocarbonyl)-2-phenyl)tetracarbonylmanganese

Conditions	Yield
In n-heptane soln. was refluxed for 5 h, after cooling, heptane was removed under vac.; elem.anal.;	100%

N,N-dimethylbenzamide (611-74-5) → N,N'-dimethylbenzylamine (103-83-3)

Conditions	Yield
With C37H46FeN4; diphenylsilane In tetrahydrofuran at 70℃; for 24h; Schlenk technique; Inert atmosphere;	99%
With Pt(ItBu)(divinyltetramethyldisiloxane); diphenylsilane In tetrahydrofuran; Hexadecane at 40℃; for 1h; Reagent/catalyst; Solvent; Schlenk technique; Inert atmosphere;	99%
With triethyl borane; phenylsilane; sodium hydroxide In tetrahydrofuran; tert-butyl methyl ether at 20℃; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique; Sealed tube; chemoselective reaction;	99%

N,N-dimethylbenzamide (611-74-5) → N,N-dimethylthiobenzamide (15482-60-7)

Conditions	Yield
With thiophosphorylated amine resin In toluene at 90℃; for 30h;	99%
With tetraphosphorus decasulfide In dichloromethane for 0.25h; Inert atmosphere; Reflux;	99%
With tetraphosphorus decasulfide; sodium carbonate In tetrahydrofuran at 25℃; for 4h;	90%

1,2-bis(4-methylphenyl)acetylene (2789-88-0) + N,N-dimethylbenzamide (611-74-5) → N,N-dimethyl-1,2,3,4,5,6,7,8-octa-(p-tolyl)anthracene-9-carboxamide

Conditions	Yield
With silver hexafluoroantimonate; copper diacetate; C46H44I4Ir2N2O4 In 1,4-dioxane at 100℃; for 24h; Glovebox; Inert atmosphere;	99%

N-Bromosuccinimide (128-08-5) + N,N-dimethylbenzamide (611-74-5) → N-methyl-N-succinimidomethylbenzamide (87329-69-9)

Conditions	Yield
With dibenzoyl peroxide In tetrachloromethane Product distribution; Heating; succinimidation by N-bromosuccinimide of N,N-dimethylamides and N,N-dimethylamines;	98%
With dibenzoyl peroxide In tetrachloromethane Heating;	98%

N,N-dimethylbenzamide (611-74-5) → benzyl alcohol (100-51-6)

Conditions	Yield
With n-butyllithium; borane-THF; diisopropylamine at 25℃;	98%
With diisobutylaluminum borohydride In tetrahydrofuran at 0 - 25℃; Inert atmosphere;	98%
With diisobutylaluminum borohydride In tetrahydrofuran at 25℃; for 1h; Inert atmosphere;	98%

acrylic acid n-butyl ester (141-32-2) + N,N-dimethylbenzamide (611-74-5) → N,N-dimethyl-2-[(E)-(n-butoxycarbonyl)ethenyl]benzamide (1373338-22-7)

Conditions	Yield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; Ag(1+)*(x)F6Sb; copper(II) acetate monohydrate In tert-Amyl alcohol at 100℃; for 4h; Inert atmosphere; regioselective reaction;	98%
With silver hexafluoroantimonate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In chlorobenzene at 80℃; for 16h; Heck Reaction; Irradiation;	91%

N,N-dimethylbenzamide (611-74-5) → benzaldehyde (100-52-7)

Conditions	Yield
With lithium diisobutylmorpholinoaluminum hydride In tetrahydrofuran; hexane at 0℃; for 0.5h; Concentration; Time;	97%
Stage #1: N,N-dimethylbenzamide With chloromagnesium dimethylaminoborohydride In tetrahydrofuran at 25℃; for 0.5h; Inert atmosphere; Stage #2: With acetaldehyde; acetic acid In tetrahydrofuran; pentane for 5h; Inert atmosphere;	74%
With diethyl ether; diisobutylaluminium hydride

1,3-diphenyl-1H-pyrazol-5-amine (5356-71-8) + N,N-dimethylbenzamide (611-74-5) → N'-(1,3-diphenyl-1H-pyrazol-5-yl)-N,N-dimethylbenzenecarboximidamide

Conditions	Yield
With trichlorophosphate at 30 - 40℃; Microwave irradiation;	97%

4-Methoxyphenethylamine (55-81-2) + N,N-dimethylbenzamide (611-74-5) → N-[2-(4-methoxyphenyl)ethyl]benzamide (3278-19-1)

Conditions	Yield
With Imidazole hydrochloride at 150℃; for 3h; Sealed tube;	97%

Li{(CH2)(CH2)P(C6H5)2} (59983-62-9) + N,N-dimethylbenzamide (611-74-5) → Methyl-diphenyl-phenacyl-phosphonium (19023-66-6) + acetophenone (98-86-2) + diphenyl(methyl)phosphine oxide (2129-89-7)

Conditions	Yield
With HX In water 1.) 2 h, -55 deg C; 2.) 13 h, 21 deg C;	A 96% B 20% C 20%
With HX In water 1.) 2 h, -55 deg C; 2.) 13 h, 21 deg C;	A 80% B 20% C 20%

N,N-dimethylbenzamide (611-74-5) → [2',6'-2H2]-N,N-dimethylbenzamide

Conditions	Yield
With C34H43IrN3(1+)*F6P(1-); deuterium In dichloromethane at -78℃; for 16h; Reagent/catalyst; Inert atmosphere;	96%
With Crabtree's catalyst; water-d2; deuterium In dichloromethane at 20℃;
With silver tetrafluoroborate; bis(1,5-cyclooctadiene)diiridium(I) dichloride; deuterium; triphenylphosphine In dichloromethane at 20℃;	2 mg
With water-d2; Ir(cod)(hfac) In N,N-dimethyl acetamide at 160℃; for 0.0333333h; microwave irradiation;
With 2,6-(2,6-iPr2-C6H3-4,5-H2-imidazol-2-ylidene)2C5H3NFe(N2)2; deuterium In tetrahydrofuran at 45℃; under 3040.2 Torr; for 24h;

tris(1,3-diphenyl-1,3-propanedionato)aquoeuropium(III) (12121-06-1) + N,N-dimethylbenzamide (611-74-5) → Eu(dibenzoylmethanate)3(dimethylbenzamide)

Conditions	Yield
In acetone Eu complex in acetone reacted with dimethylbenzamide; solvent evapd., ppt. washed with water, vac. dried; elem. anal.;	96%

1H-imidazole (288-32-4) + N,N-dimethylbenzamide (611-74-5) → N-((1H-imidazol-1-yl)methyl)-N-methylbenzamide (1402844-74-9)

Conditions	Yield
With di-tert-butyl peroxide; iron(II) chloride In chlorobenzene at 120℃; for 3h; Inert atmosphere; Schlenk technique;	96%

2-chloro-1H-benzoimidazole (4857-06-1) + N,N-dimethylbenzamide (611-74-5) → N-((2-chloro-1H-benzo[d]imidazol-1-yl)methyl)-N-methylbenzamide

Conditions	Yield
With dipotassium peroxodisulfate; potassium iodide at 80℃; for 6h; Schlenk technique;	96%

C54H62N6 + N,N-dimethylbenzamide (611-74-5) → C61H65N6(1+)*F6P(1-)

Conditions	Yield
Stage #1: C54H62N6; N,N-dimethylbenzamide With trichlorophosphate In 1,2-dichloro-ethane at 20 - 40℃; for 2h; Vilsmeier-Haack Formylation; Inert atmosphere; Stage #2: With potassium hexafluorophosphate; sodium hydrogencarbonate In water	96%

Upstream product

• 532-32-1 sodium benzoate 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 
• 93-58-3 benzoic acid methyl ester 
• 84738-97-6 methylchloroaluminum N,N-dimethylamide 
• 613-90-1 benzoyl cyanide 
• 67751-11-5 N,N,N',N'-Tetramethylharnstoff-diethylacetal 
• 2214-82-6 Bis(dimethylamino)acetonitrile 
• 103-83-3 N,N'-dimethylbenzylamine 
• 577-85-5 3-hydroxyflavone 
• 68-12-2 N,N-dimethyl-formamide 
• 123707-27-7 N-methoxyurea-N,N',N'-trimethylurea 
• 80179-40-4 N-<(Dimethylamino)methyl>-N-methylacetamid 
• 80179-41-5 N-<(Dimethylamino)methyl>-N-methylbenzamid 
• 35452-04-1 N,N-dimethylbenzamide dimethyl acetal 

Downstream Products

• 38435-17-5 C₁₁H₁₇N₃ 
• 64713-81-1 O-isopropyl selenobenzoate 
• 62128-30-7 (1-methyl-1H-pyrrol-3-yl)(phenyl)methanone 
• 77375-17-8 2-methyl-1,2,4-triazol-3-yl phenyl ketone 
• 141054-41-3 ethyl 5-benzoylpyrrol-2-ylacetate 
• 104728-70-3 3-hydroxy-2,3-diphenyl-7-azaisoindolinone 
• 104703-16-4 Ethyl 2-(3-Benzoyl-1-methylindole)acetate 
• 119-61-9 benzophenone 
• 129147-73-5 7-Amino-2-phenyl<1,2,4>triazolo<1,5-c>pyrimidin-5(6H)-thione 
• 161144-22-5 2-Benzoyl-4,5-dihydrofuran 
• 31518-17-9 6-benzoyl-3,4-dihydro-(2H)-pyran 
• 120061-18-9 3-benzylamino-4-benzoylsydnone 
• 1083-30-3 dihydrochalcone 
• 98-86-2 acetophenone 

Relevant articles and documents

-

-

A Convenient and Stable Heterogeneous Nickel Catalyst for Hydrodehalogenation of Aryl Halides Using Molecular Hydrogen

Hydrodehalogenation is an effective strategy for transforming persistent and potentially toxic organohalides into their more benign congeners. Common methods utilize Pd/C or Raney-nickel as catalysts, which are either expensive or have safety concerns. In this study, a nickel-based catalyst supported on titania (Ni-phen@TiO2-800) is used as a safe alternative to pyrophoric Raney-nickel. The catalyst is prepared in a straightforward fashion by deposition of nickel(II)/1,10-phenanthroline on titania, followed by pyrolysis. The catalytic material, which was characterized by SEM, TEM, XRD, and XPS, consists of nickel nanoparticles covered with N-doped carbon layers. By using design of experiments (DoE), this nanostructured catalyst is found to be proficient for the facile and selective hydrodehalogenation of a diverse range of substrates bearing C?I, C?Br, or C?Cl bonds (>30 examples). The practicality of this catalyst system is demonstrated by the dehalogenation of environmentally hazardous and polyhalogenated substrates atrazine, tetrabromobisphenol A, tetrachlorobenzene, and a polybrominated diphenyl ether (PBDE).

Visible-light-induced direct construction of amide bond from carboxylic acids with amines in aqueous solution

A novel visible-light-promoted N-acylation for the synthesis of amides from easily available carboxylic acids with amines in the presence of I2 within 2.5 h in aqueous solution has been developed. Using sunlight as the visible light source greatly reduces the cost of experiments and produces almost no toxic effects. Hence, this study provides an alternative catalytic system for the construction of a wide range of amides with readily available materials. Moreover, the strategy was successfully applied in the preparation of N-(3-(2,6-dimethoxyphenoxy)-7-nitroquinoxalin-2-yl)benzohydrazide, which displayed a signification anti-proliferation effect on A549, MCF-7 and HCT116 cell lines.