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3278-14-6

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3278-14-6 Usage

Uses

N-Phenethylbenzamide was used for the synthesis of deteurerium-labeled amides within microreactors.

Check Digit Verification of cas no

The CAS Registry Mumber 3278-14-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,2,7 and 8 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 3278-14:
(6*3)+(5*2)+(4*7)+(3*8)+(2*1)+(1*4)=86
86 % 10 = 6
So 3278-14-6 is a valid CAS Registry Number.
InChI:InChI=1/C15H15NO/c17-15(14-9-5-2-6-10-14)16-12-11-13-7-3-1-4-8-13/h1-10H,11-12H2,(H,16,17)

3278-14-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name N-(2-phenylethyl)benzamide

1.2 Other means of identification

Product number -
Other names benzoic acid phenethylamide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:3278-14-6 SDS

3278-14-6Synthetic route

benzoyl chloride
98-88-4

benzoyl chloride

phenethylamine
64-04-0

phenethylamine

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 23℃;100%
With triethylamine In dichloromethane at 0 - 30℃; for 12h;100%
With sodium hydroxide In water at 10 - 20℃; for 3h; Cooling with ice;99%
(Z)-N-phenethylbenzimidoyl cyanide
1019849-88-7

(Z)-N-phenethylbenzimidoyl cyanide

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
With aluminum oxide In toluene at 130℃; for 1h; Temperature; Time; Reagent/catalyst; Solvent; Microwave irradiation; Inert atmosphere;100%
phenyl(2-phenylaziridin-1-yl)methanone
93638-44-9

phenyl(2-phenylaziridin-1-yl)methanone

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene for 2h; Heating;99%
Multi-step reaction with 2 steps
1: 70 percent / conc. aq. HCl / diethyl ether / 0.25 h
2: 1) n-BuLi / 1) hexane, THF 2) THF, 5 min
View Scheme
phenethylamine
64-04-0

phenethylamine

benzoic acid
65-85-0

benzoic acid

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In methanol at 110℃; for 0.416667h; Microwave irradiation;99%
With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium In methanol at 25℃; for 1h; Reagent/catalyst; Solvent;99%
With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In methanol at 20℃; for 2h;97%
phenethylamine
64-04-0

phenethylamine

N-benzoyl-N-(2,3,4,5,6-pentafluorophenyl)methanesulfonamide
300561-20-0

N-benzoyl-N-(2,3,4,5,6-pentafluorophenyl)methanesulfonamide

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
In tetrahydrofuran at 23℃; for 0.333333h; Acylation;99%
benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

phenethylamine
64-04-0

phenethylamine

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
With 14C2H2F3O(1-)*6C4H8O*La2Na8(14+) at 80℃; for 6h; Inert atmosphere;99%
With sodium t-butanolate In neat (no solvent) at 20℃; for 1h; Inert atmosphere; Schlenk technique; Green chemistry;98%
With C18H15IMnN3O3; sodium t-butanolate In toluene at 90℃; for 18h; Inert atmosphere; Schlenk technique;95%
With niobium(V) oxide In neat (no solvent) at 140℃; for 30h; Molecular sieve; Inert atmosphere;91%
With zirconocene dichloride In toluene at 110℃; for 20h;74%
benzoyltrimethylsilane
5908-41-8

benzoyltrimethylsilane

phenethyl azide
6926-44-9

phenethyl azide

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 0.166667h; Schmidt Reaction; Inert atmosphere;99%
(E)-1-((N,4-dimethylphenyl)sulfonamido)-2-phenylvinyl benzoate

(E)-1-((N,4-dimethylphenyl)sulfonamido)-2-phenylvinyl benzoate

phenethylamine
64-04-0

phenethylamine

A

N-methyl-N-(p-tolylsulfonyl)phenylacetamide
1005500-94-6

N-methyl-N-(p-tolylsulfonyl)phenylacetamide

B

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
In dichloromethane at 25℃; for 1h;A 99%
B 99%
benzoyltrimethylsilane
5908-41-8

benzoyltrimethylsilane

O-diethylcarbamoyl-N-phenethylhydroxylamine
1590361-11-7

O-diethylcarbamoyl-N-phenethylhydroxylamine

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
With citric acid In water; acetonitrile at 20℃; for 0.2h; chemoselective reaction;99%
3-benzoyl-1,3-oxazolidin-2-one
7007-15-0

3-benzoyl-1,3-oxazolidin-2-one

phenethylamine
64-04-0

phenethylamine

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
bis(cyclopentadienyl)titanium dichloride In tetrahydrofuran at 25℃; for 18h;98%
C22H21N3OS

C22H21N3OS

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran; methanol at 0℃;98%
DL-N-benzoylphenylalanine
2566-22-5, 2901-76-0, 37002-52-1

DL-N-benzoylphenylalanine

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
With 2,6-dimethylpyridine; 4,4'-dichlorodiphenyl disulfide; 10-methyl-9-(2,4,6-trimethylphenyl) acridinium tetrafluoroborate In 1,2-dichloro-ethane at 20℃; for 14h; Irradiation; Inert atmosphere;98%
Multi-step reaction with 2 steps
1: DCC, DMAP
2: 93 percent / Bu3SnH, AIBN / benzene / 1 h / Heating
View Scheme
phenethylamine
64-04-0

phenethylamine

benzoic acid
65-85-0

benzoic acid

A

3-phenylpropanoic acid methyl ester
103-25-3

3-phenylpropanoic acid methyl ester

B

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
With N-[4-methoxy-6-(N'-phenylbenzamido)-1,3,5-triazin-2-yl]-N-methylmorpholinium chloride In methanol at 20℃; for 4h;A 8 %Spectr.
B 97%
N-(2-phenylethyl)-p-chlorobenzamide
39887-24-6

N-(2-phenylethyl)-p-chlorobenzamide

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
With dimethylamine borane; potassium carbonate; triphenylphosphine; Ni(II)/C In acetonitrile for 7h; Heating;96%
C22H21NO2S
1245735-60-7

C22H21NO2S

benzoyl chloride
98-88-4

benzoyl chloride

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
Stage #1: C22H21NO2S With piperidine In N,N-dimethyl-formamide at 25℃; for 0.0166667h;
Stage #2: benzoyl chloride With triethylamine In N,N-dimethyl-formamide at 25℃; for 8h;
96%
benzamide
55-21-0

benzamide

phenethylamine
64-04-0

phenethylamine

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
With sulfated tungstate In toluene for 12h; Reflux; Green chemistry;96%
With chitosan In neat (no solvent) at 150℃; for 36h; Sealed tube;90%
With 1-(3-sulfopropyl)pyridinium phosphotungstate In neat (no solvent) at 140℃; for 0.833333h; Microwave irradiation;88%
N-chloro-2-phenylethanamine

N-chloro-2-phenylethanamine

benzaldehyde
100-52-7

benzaldehyde

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
With tert.-butylhydroperoxide; copper(II) acetate monohydrate at 82℃; for 0.833333h; Minisci Aromatic Substitution; Inert atmosphere;96%
With tert.-butylhydroperoxide; 2,2'-azobis(isobutyronitrile) In water; acetonitrile at 80℃; for 24h; Mechanism;82%
With tert.-butylhydroperoxide; iron(III) chloride hexahydrate In water; acetonitrile Inert atmosphere; Reflux;57%
2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

benzoic acid
65-85-0

benzoic acid

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
Stage #1: benzoic acid With 1,1'-carbonyldiimidazole In neat (no solvent) for 0.0833333h; Milling;
Stage #2: 2-phenylethylamine hydrochloride In neat (no solvent) for 0.166667h; Milling;
96%
Stage #1: benzoic acid With 1,1'-carbonyldiimidazole for 0.0833333h; Milling; Green chemistry;
Stage #2: 2-phenylethylamine hydrochloride for 0.166667h; Milling; Green chemistry;
96%
C16H17N3O4

C16H17N3O4

phenethylamine
64-04-0

phenethylamine

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
In methanol at 20℃; for 1.5h; Solvent;96%
C16H14N2
74491-35-3

C16H14N2

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
With aluminum oxide at 20℃; Concentration; Inert atmosphere;95%
C17H17NO3S2

C17H17NO3S2

phenethylamine
64-04-0

phenethylamine

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.5h;95%
4-(5-allyl-6-isopropoxy-4-oxo-4,5-dihydro-1,3,5-triazine-2-yl)-4-methylmorpholine-4-ium chloride

4-(5-allyl-6-isopropoxy-4-oxo-4,5-dihydro-1,3,5-triazine-2-yl)-4-methylmorpholine-4-ium chloride

phenethylamine
64-04-0

phenethylamine

benzoic acid
65-85-0

benzoic acid

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 0.5h;95%
methanol
67-56-1

methanol

3-phenethyl-4,5-diphenyl-3H-oxazol-2-one
37628-64-1

3-phenethyl-4,5-diphenyl-3H-oxazol-2-one

A

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

B

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
With oxygen Product distribution; Irradiation;A 80%
B 94%
Irradiation;A 80%
B 94%
C29H24N2O3Se
195874-39-6

C29H24N2O3Se

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene for 1h; Heating;93%
benzoic acid ethyl ester
93-89-0

benzoic acid ethyl ester

phenethylamine
64-04-0

phenethylamine

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
With potassium tert-butylate; water; oxygen In tetrahydrofuran at 20℃; for 0.25h;93%
1-Benzoyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester

1-Benzoyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester

phenethylamine
64-04-0

phenethylamine

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
Stage #1: 1-Benzoyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 15h;
Stage #2: phenethylamine With dmap In dichloromethane at 20℃; for 8h;
93%
phenethylamine
64-04-0

phenethylamine

N-benzoyl-N-(2-fluorophenyl)methanesulfonamide
215657-47-9

N-benzoyl-N-(2-fluorophenyl)methanesulfonamide

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
In tetrahydrofuran at 23℃; for 2h; Acylation;91%
methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

trans-N-styryl-benzamide
78007-47-3

trans-N-styryl-benzamide

A

methyl N-benzoylphenylalaninate
74923-17-4

methyl N-benzoylphenylalaninate

B

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
With dicobalt octacarbonyl; hydrogen In tetrahydrofuran at 100℃; for 16h; Product distribution; Further Variations:; Temperatures; CO/H2 ratio;A 91%
B n/a
2-benzoyl-1,3-dimethyl-1H-imidazol-3-ium iodide
99802-96-7

2-benzoyl-1,3-dimethyl-1H-imidazol-3-ium iodide

phenethylamine
64-04-0

phenethylamine

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1h; Inert atmosphere; Sealed tube; regioselective reaction;91%
C29H24N2O3
115975-10-5

C29H24N2O3

A

benzophenone
119-61-9

benzophenone

B

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

C

benzophenone azine
983-79-9

benzophenone azine

Conditions
ConditionsYield
With 2-methylpropan-2-thiol In isopropyl alcohol Ambient temperature; Irradiation; Yields of byproduct given;A n/a
B 90%
C n/a
N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

N-(2-phenethyl)-benzimidoyl trifluoroacetate

N-(2-phenethyl)-benzimidoyl trifluoroacetate

Conditions
ConditionsYield
In diethyl ether at 20 - 25℃;100%
N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

1-phenyl-3,4-dihydroisoquinoline
52250-50-7

1-phenyl-3,4-dihydroisoquinoline

Conditions
ConditionsYield
With 2-chloropyridine; trifluoromethylsulfonic anhydride In dichloromethane at -78 - 45℃; Bischler-Napieralski reaction; Inert atmosphere;95%
With polyphosphoric acid at 180 - 200℃;95%
With phosphorus pentoxide; trichlorophosphate In 5,5-dimethyl-1,3-cyclohexadiene Bischler-Napieralski Reaction; Reflux;92%
N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

N-(2-phenethyl)benzimidoyl chloride hydrochloride
77988-90-0

N-(2-phenethyl)benzimidoyl chloride hydrochloride

Conditions
ConditionsYield
With phosphorus pentachloride In benzene at 0℃; for 1h;94%
N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

1-phenyl-3,4-dihydroisoquinoline hydrochloride
52250-51-8

1-phenyl-3,4-dihydroisoquinoline hydrochloride

Conditions
ConditionsYield
Stage #1: N-phenethylbenzamide With phosphorus pentoxide; trichlorophosphate In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 5h;
Stage #2: With hydrogenchloride In tert-butyl methyl ether; water for 1h;
93%

3278-14-6Relevant articles and documents

Direct carbodiimide-mediated conjugation of carboxylates using pyridinium p-toluenesulfonate and tertiary amines as additives

Ficht, Simon,R?glin, Lars,Ziehe, Matthias,Breyer, David,Seitz, Oliver

, p. 2525 - 2528 (2004)

The use of carboxylates in the carbodiimide-mediated coupling to amines was investigated. The addition of pyridinium p-toluenesulfonate (PPTS) and a tertiary amine was found to significantly improve acylation yields by up to 70%.

Synthesis, characterization and cytotoxic evaluation of inclusion complexes between Riparin A and β-cyclodextrin

Araújo, éverton José Ferreira de,Silva, Oskar Almeida,Rezende-Júnior, Luís Mário,Sousa, Ian Jhemes Oliveira,Araújo, Danielle Yasmin Moura Lopes de,Carvalho, Rusbene Bruno Fonseca de,Pereira, Sean Telles,Gutierrez, Stanley Juan Chavez,Ferreira, Paulo Michel Pinheiro,Lima, Francisco das Chagas Alves

, p. 84 - 91 (2017)

This study performed a physicochemical characterization of the inclusion complex generated between Riparin A and β-cyclodextrin (Rip A/β-CD) and compared the cytotoxic potential of the incorporated Rip A upon Artemia salina larvae. Samples were analyzed by phase solubility diagram, dissolution profile, differential scanning calorimetry, X-ray diffraction, infrared spectroscopy, proton nuclear magnetic resonance, scanning electron microscopy and artemicidal action. Riparin A/β-cyclodextrin complexes presented increased water solubility, AL type solubility diagram and Kst constant of 373?L/mol. Thermal analysis demonstrated reduction of the melt peak of complexed Rip A at 116.2?°C. Infrared spectroscopy confirmed generation of inclusion complexes, 1H NMR pointed out the interaction with H-3 of β-CD cavities, alterations in the crystalline natures of Rip A when incorporated within β-CD were observed and inclusion complexes presented higher cytotoxic on A.?salina nauplii, with CL50 value of 117.2 (84.9–161.8) μg/mL. So, Rip A was incorporated into β-CDs with high efficiency and water solubility of Rip A was improved. Such solubility was corroborated by cytotoxic evaluation and these outcomes support the improvement of biological properties for complexes between Riparin A/β-cyclodextrin.

Sustainable triazine-based dehydro-condensation agents for amide synthesis

Sole, Roberto,Gatto, Vanessa,Conca, Silvia,Bardella, Noemi,Morandini, Andrea,Beghetto, Valentina

, (2021/04/26)

Conventional methods employed today for the synthesis of amides often lack of economic and environmental sustainability. Triazine-derived quaternary ammonium salts, e.g., 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM(Cl)), emerged as promising dehydro-condensation agents for amide synthesis, although suffering of limited stability and high costs. In the present work, a simple protocol for the synthesis of amides mediated by 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) and a tert-amine has been described and data are compared to DMTMM(Cl) and other CDMT-derived quaternary ammonium salts (DMT-Ams(X), X: Cl? or ClO4?). Different tert-amines (Ams) were tested for the synthesis of various DMT-Ams(Cl), but only DMTMM(Cl) could be isolated and employed for dehydro-condensation reactions, while all CDMT/tert-amine systems tested were efficient as dehydro-condensation agents. Interestingly, in best reaction conditions, CDMT and 1,4-dimethylpiperazine gave N-phenethyl benzamide in 93% yield in 15 min, with up to half the amount of tert-amine consumption. The efficiency of CDMT/tert-amine was further compared to more stable triazine quaternary ammonium salts having a perchlorate counter anion (DMT-Ams(ClO4)). Overall CDMT/tert-amine systems appear to be a viable and more economical alternative to most dehydro-condensation agents employed today.

Method for preparing amide from carboxylic acid under irradiation of blue light by taking iridium and cobalt complexes as catalysts

-

Paragraph 0073-0074, (2021/05/12)

The invention relates to a method for preparing amide from carboxylic acid under the irradiation of blue light by taking iridium and cobalt complexes as catalysts, and belongs to the field of chemistry. The method comprises the following step of: by taking R substituted carboxylic acid and R1' and R2' substituted amines as raw materials, triphenylphosphine as a deoxidizing agent, [Ir(dF(CF3)ppy)2(dtbbpy)]PF6 as a photocatalyst and Co(dmgH)(dmgH2)Cl2 as a metal complex catalyst, reacting in dichloromethane in an inert atmosphere and under the irradiation of blue light to obtain an amide compound, wherein R is an aryl group, a heteroaryl group, a protected amino group, a substituted alkyl group, a substituted aryl group or a substituted protected amino group, R1' is a hydrogen group, a substituted alkyl group, a phenyl group or a substituted phenyl group, and R2' is a hydrogen group, a substituted alkyl group, a phenyl group or a substituted phenyl group.

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