Product Name

  • Name

    N,N-Diethyl-m-toluamide

  • EINECS 205-149-7
  • CAS No. 134-62-3
  • Article Data51
  • CAS DataBase
  • Density 0.985 g/cm3
  • Solubility solubility in water is negligible
  • Melting Point -45oC
  • Formula C12H17NO
  • Boiling Point 297.5 °C at 760 mmHg
  • Molecular Weight 191.273
  • Flash Point 141.7 °C
  • Transport Information
  • Appearance Colorless to Amberlike Liquid
  • Safety 61
  • Risk Codes 22-36/38-52/53
  • Molecular Structure Molecular Structure of 134-62-3 (N,N-Diethyl-m-toluamide)
  • Hazard Symbols HarmfulXn
  • Synonyms m-Toluamide,N,N-diethyl- (6CI,7CI,8CI);3-Methyl-N,N-diethylbenzamide;AminceneC 140;Cutter Unscented;DETA;Delphene;Dieltamid;Diethyl-m-toluamide;Diethyltoluamide;ENT 22542;Flypel;Metadelfene;Metadelphene;N,N-Diethyl-m-methylbenzamide;
  • PSA 20.31000
  • LogP 2.47700

Synthetic route

diethylamine
109-89-7

diethylamine

3-Methylbenzoyl chloride
1711-06-4

3-Methylbenzoyl chloride

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

Conditions
ConditionsYield
With sodium hydroxide In water at 45℃; for 0.05h; Temperature; Reagent/catalyst;97.5%
With benzene
With triethylamine Heating; Microwave irradiation;
With triethylamine In dichloromethane at 0 - 20℃;
at 0 - 20℃; for 20h; Alkaline conditions;
N,N-diethylcarbamyl chloride
88-10-8

N,N-diethylcarbamyl chloride

m-Toluic acid
99-04-7

m-Toluic acid

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

Conditions
ConditionsYield
With triethylamine at 20℃; for 0.333333h;97.5%
With triethylamine at 20℃; for 0.333333h;97.5%
diethylamine
109-89-7

diethylamine

m-Toluic acid
99-04-7

m-Toluic acid

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

Conditions
ConditionsYield
With Zn-MCM-22 catalyst at 100 - 280℃; under 15001.5 Torr; for 6h; Inert atmosphere; Large scale;96%
Stage #1: m-Toluic acid With niobium pentachloride In dichloromethane
Stage #2: diethylamine In dichloromethane at 45 - 50℃; for 2.5h;		85%
hydroxy-apatite at 280 - 320℃; Product distribution; other catalysts; var. reaction time and temp.; influence of mineral acids with different pKa values;
N-formyldiethylamine
617-84-5

N-formyldiethylamine

m-Toluic acid
99-04-7

m-Toluic acid

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

Conditions
ConditionsYield
With hydrogenchloride; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In 1,4-dioxane at 120℃; for 22h;91%
3-Methylbenzonitrile
620-22-4

3-Methylbenzonitrile

diethylamine
109-89-7

diethylamine

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

Conditions
ConditionsYield
Stage #1: diethylamine With ethylmagnesium bromide In tetrahydrofuran; diethyl ether at 30℃; for 1h;
Stage #2: 3-Methylbenzonitrile With ethylmagnesium bromide In diethyl ether; dichloromethane at 30℃; for 1h;
Stage #3: With hydrogenchloride In tetrahydrofuran; diethyl ether; dichloromethane at 22℃;		90%
3-Methylbenzotrichloride
3335-34-0

3-Methylbenzotrichloride

triethylamine
121-44-8

triethylamine

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

Conditions
ConditionsYield
With heptamethyl Coβ-perchlorato-cob(II)yrinate; tetrabutylammonium perchlorate In acetonitrile at 20℃; for 3h; Electrolysis;90%
carbon monoxide
201230-82-2

carbon monoxide

3-Iodotoluene
625-95-6

3-Iodotoluene

diethylamine
109-89-7

diethylamine

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

Conditions
ConditionsYield
With palladium diacetate; triethylamine; triphenylphosphine In toluene at 80℃; for 18h; Sealed tube;89%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; under 750.075 Torr; for 2h; Autoclave; chemoselective reaction;85%
With triethylamine In N,N-dimethyl acetamide at 130℃; under 15001.5 Torr; for 1.5h; Autoclave; Green chemistry;84%
...Expand
triethylamine
121-44-8

triethylamine

m-Toluic acid
99-04-7

m-Toluic acid

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

Conditions
ConditionsYield
With trifuran-2-yl-phosphane; palladium diacetate; 2,2-dimethylpropanoic anhydride In toluene at 120℃; for 15h; Inert atmosphere;89%
m-toluic acid diethylammonium salt

m-toluic acid diethylammonium salt

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

Conditions
ConditionsYield
at 200℃; for 0.0277778h; Product distribution / selectivity; microwave irradiation;88%
potassium trifluoro(3-methylphenyl)borate

potassium trifluoro(3-methylphenyl)borate

2-(diethylamino)-2-oxoacetic acid
55441-26-4

2-(diethylamino)-2-oxoacetic acid

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

Conditions
ConditionsYield
With dipotassium peroxodisulfate; palladium diacetate In water; dimethyl sulfoxide; acetonitrile at 20℃;86%
m-toluic acid diethylammonium salt

m-toluic acid diethylammonium salt

A

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

B

N-ethyl-m-Toluamide
26819-07-8

N-ethyl-m-Toluamide

Conditions
ConditionsYield
With tetrabutoxytitanium at 200℃; under 15001.5 Torr; for 0.0333333h; Product distribution / selectivity; microwave irradiation;A 81%
B 9%
furfural
98-01-1

furfural

3-Iodotoluene
625-95-6

3-Iodotoluene

triethylamine
121-44-8

triethylamine

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

Conditions
ConditionsYield
With Wilkinson’s catalyst; 1,3-bis-(diphenylphosphino)propane; water In tetrahydrofuran at 140℃; for 12h; Inert atmosphere; Sealed tube;80%
...Expand
diethyl amine hydrochloride
660-68-4

diethyl amine hydrochloride

m-Toluic acid
99-04-7

m-Toluic acid

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

Conditions
ConditionsYield
With silica gel; triethylamine; p-toluenesulfonyl chloride at 20℃; for 0.0166667h;76%
With triethylamine at 20℃; for 0.0166667h;60%
1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
4064-06-6

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

N,N-diethyl-α,α-difluoro-(meta-methylbenzyl)amine
500131-50-0

N,N-diethyl-α,α-difluoro-(meta-methylbenzyl)amine

A

6-deoxy-6-fluoro-1,2:3,4-di-O-isopropylidene-α-D-galctopyranose
2021-97-8, 6185-32-6, 70981-54-3

6-deoxy-6-fluoro-1,2:3,4-di-O-isopropylidene-α-D-galctopyranose

B

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

Conditions
ConditionsYield
In n-heptane for 0.333333h; microwave irradiation;A 70%
B n/a
...Expand
isopropyl 2-(diethylcarbamoyl)-4-methylbenzoate

isopropyl 2-(diethylcarbamoyl)-4-methylbenzoate

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); sodium t-butanolate In toluene at 20 - 180℃; for 14h; Inert atmosphere; Glovebox; Sealed tube;64%
N,N-Diethyl-3-methyl-2-(2-methyl-propane-2-sulfonyl)-benzamide
118354-88-4

N,N-Diethyl-3-methyl-2-(2-methyl-propane-2-sulfonyl)-benzamide

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

Conditions
ConditionsYield
With hydrogen; nickel In ethanol for 15h; Heating;55%
tert-butyl phenyl sulfide
3019-19-0

tert-butyl phenyl sulfide

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: H2O2 / acetic acid / 3 h / 100 °C
2: 1.) n-BuLi / 1.) THF, -78 deg C, 0.5 h, 2.) -78 deg C
3: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C
4: 55 percent / H2 / Raney Ni / ethanol / 15 h / Heating
View Scheme
tert-butyl-phenyl sulfone
4170-72-3

tert-butyl-phenyl sulfone

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) n-BuLi / 1.) THF, -78 deg C, 0.5 h, 2.) -78 deg C
2: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C
3: 55 percent / H2 / Raney Ni / ethanol / 15 h / Heating
View Scheme
2-<(1,1-dimethylethyl)sulphonyl>-N,N'-diethylbenzamide
118335-04-9

2-<(1,1-dimethylethyl)sulphonyl>-N,N'-diethylbenzamide

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C
2: 55 percent / H2 / Raney Ni / ethanol / 15 h / Heating
View Scheme
phenyllithium
591-51-5

phenyllithium

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: tetrahydrofuran / -78 °C
2: H2O2 / acetic acid / 3 h / 100 °C
3: 1.) n-BuLi / 1.) THF, -78 deg C, 0.5 h, 2.) -78 deg C
4: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C
5: 55 percent / H2 / Raney Ni / ethanol / 15 h / Heating
View Scheme
diethylamine
109-89-7

diethylamine

m-toluic acid n-butyl ester

m-toluic acid n-butyl ester

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

Conditions
ConditionsYield
sodium ethanolate at 305℃; under 26252.6 Torr; for 0.00944444h; autoclave; Industry scale; Microwave irradiation;
ortho-methylbenzoic acid
118-90-1

ortho-methylbenzoic acid

thionyl chloride
7719-09-7

thionyl chloride

dichloromethane
75-09-2

dichloromethane

dibenzylamine
103-49-1

dibenzylamine

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

Conditions
ConditionsYield
Stage #1: ortho-methylbenzoic acid; thionyl chloride; dichloromethane With N,N-dimethyl-formamide for 2h; Reflux;
Stage #2: dibenzylamine at 20℃;
...Expand
diethylamine
109-89-7

diethylamine

3-(3-methylbenzoyl)-5,5-dimethylhydantoin

3-(3-methylbenzoyl)-5,5-dimethylhydantoin

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

Conditions
ConditionsYield
In ethyl acetate at 50℃; Sealed tube;
3-methylbenzyl alcohol
587-03-1

3-methylbenzyl alcohol

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydrogencarbonate; iron(III) chloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile; water / 35 °C
2: ethyl acetate / 50 °C / Sealed tube
View Scheme
m-Toluic acid
99-04-7

m-Toluic acid

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1,3,5-trichloro-2,4,6-triazine; 1-pyrrolidinecarboxaldehyde / acetonitrile / Heating
2: 20 h / 0 - 20 °C / Alkaline conditions
View Scheme
2-bromo-5-methylbenzoic acid
6967-82-4

2-bromo-5-methylbenzoic acid

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 2 h / 0 - 20 °C
1.2: 0 - 20 °C
2.1: zinc(II) chloride; diisobutylaluminium hydride; magnesium; lithium chloride / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere
2.2: 50 °C / Inert atmosphere
3.1: bis(1,5-cyclooctadiene)nickel (0); sodium t-butanolate / toluene / 14 h / 20 - 180 °C / Inert atmosphere; Glovebox; Sealed tube
View Scheme
2-bromo-N,N-diethyl-5-methylbenzamide

2-bromo-N,N-diethyl-5-methylbenzamide

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: zinc(II) chloride; diisobutylaluminium hydride; magnesium; lithium chloride / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere
1.2: 50 °C / Inert atmosphere
2.1: bis(1,5-cyclooctadiene)nickel (0); sodium t-butanolate / toluene / 14 h / 20 - 180 °C / Inert atmosphere; Glovebox; Sealed tube
View Scheme
N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

N-ethyl-N-(3-methylbenzyl)ethanamine
22704-60-5

N-ethyl-N-(3-methylbenzyl)ethanamine

Conditions
ConditionsYield
With n-butyllithium; borane-THF; diisopropylamine at 25℃;99%
With lithium (diisopropylamino)borohydride In tetrahydrofuran at 25℃; for 2h;99%
With diisobutylaluminum borohydride In tetrahydrofuran at 0 - 25℃; Inert atmosphere;99%
styrene
292638-84-7

styrene

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

N,N-diethyl-5-methyl-2-(1-phenylethyl)benzamide
1620210-49-2

N,N-diethyl-5-methyl-2-(1-phenylethyl)benzamide

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; 1,4-bis[bis(pentafluorophenyl)phosphino]butane In 1,4-dioxane at 100℃; for 48h; Sealed tube; Inert atmosphere;99%
N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

N,N-diethyl-αlpha;-chloro-meta-toluylamidinum chloride
500131-49-7

N,N-diethyl-αlpha;-chloro-meta-toluylamidinum chloride

Conditions
ConditionsYield
With oxalyl dichloride In tetrachloromethane at 0 - 50℃; for 1.5h;98%
With oxalyl dichloride In tetrachloromethane at 0 - 50℃; for 1.5h;98%
With oxalyl dichloride In tetrachloromethane at 0 - 50℃; for 1.5h;
With oxalyl dichloride In tetrachloromethane at 0 - 50℃; for 1.5h;
1,1,1,3,5,5,5-heptamethyltrisiloxan
1873-88-7

1,1,1,3,5,5,5-heptamethyltrisiloxan

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

C19H37NO3Si3
1583285-82-8

C19H37NO3Si3

Conditions
ConditionsYield
With [Rh(coe)2OH]2; 3,4,5-MeO-MeO-BIPHEP; cyclohexene In tetrahydrofuran at 45℃; regioselective reaction;96%
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 2.9-dimethyl-1,10-phenanthroline In 1,4-dioxane at 100℃; for 20h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Sealed tube; regioselective reaction;63%
N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

3-methylbenzyl alcohol
587-03-1

3-methylbenzyl alcohol

Conditions
ConditionsYield
With pyrrolidine; n-butyllithium; borane-THF at 25℃;95%
With LiPyrrBH3 In tetrahydrofuran at 25℃; for 2h;95%
N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

N,N-diethyl 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

N,N-diethyl 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Conditions
ConditionsYield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In hexane at 80℃; for 18h; Inert atmosphere; Sealed tube; regioselective reaction;95%
Stage #1: bis(pinacol)diborane With C24H28ClIrN2O In n-heptane; isopropyl alcohol at 75℃; for 1h; Sealed tube; Inert atmosphere;
Stage #2: N,N-Diethyl-3-methylbenzamide In n-heptane; isopropyl alcohol Sealed tube; Inert atmosphere;		87%
Stage #1: bis(pinacol)diborane With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2’-bipyridine In hexane at 60℃; for 0.5h; Inert atmosphere; Glovebox; Sealed tube;
Stage #2: N,N-Diethyl-3-methylbenzamide With bis(2,6-di-tert-butyl-4-methylphenoxide)methylaluminum In hexane at 20℃; for 18h; Sealed tube;		55%
N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

N,N-diethyl-3-methylthiobenzamide
1017241-61-0

N,N-diethyl-3-methylthiobenzamide

Conditions
ConditionsYield
With triethylamine; trichlorophosphate In water at 60 - 70℃; for 0.0833333h; microwave irradiation;89%
With trichlorothiophosphine; water; triethylamine Microwave irradiation;89%
With trichlorothiophosphine; water; triethylamine Heating; Microwave irradiation;
N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

C24H30LaN3

C24H30LaN3

(4-(dimethylamino)phenyl)(m-tolyl)methanone
26704-95-0

(4-(dimethylamino)phenyl)(m-tolyl)methanone

Conditions
ConditionsYield
at 0℃; for 1h; Inert atmosphere; Schlenk technique;86%
N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

N,N-diethyl-α,α-difluoro-(meta-methylbenzyl)amine
500131-50-0

N,N-diethyl-α,α-difluoro-(meta-methylbenzyl)amine

Conditions
ConditionsYield
Stage #1: N,N-Diethyl-3-methylbenzamide With oxalyl dichloride In dichloromethane at 40℃; for 2h;
Stage #2: With triethylamine tris(hydrogen fluoride); triethylamine In dichloromethane at 20℃; for 2h;		82%
Stage #1: N,N-Diethyl-3-methylbenzamide With oxalyl dichloride In dichloromethane at 40℃; for 2h;
Stage #2: With triethylamine tris(hydrogen fluoride); triethylamine In dichloromethane at 20℃; for 2h; Further stages.;		82%
With Carbonyl fluoride In 1,2-dichloro-ethane at 158℃; for 10h; Product distribution / selectivity;60%
With Carbonyl fluoride at 72 - 170℃; for 10h; Product distribution / selectivity;7%
N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

1-((5-phenylpent-1-en-2-yl)oxy)pyridin-1-ium bis((trifluoromethyl)sulfonyl)amide

1-((5-phenylpent-1-en-2-yl)oxy)pyridin-1-ium bis((trifluoromethyl)sulfonyl)amide

2-oxo-5-phenylpentyl 3-methylbenzoate

2-oxo-5-phenylpentyl 3-methylbenzoate

Conditions
ConditionsYield
With water In dichloromethane at 45℃; for 6h;82%
With water at 60℃; for 18h;82%
ethanol
64-17-5

ethanol

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

ethyl 3-methylbenzoate
120-33-2

ethyl 3-methylbenzoate

Conditions
ConditionsYield
With hydrogenchloride; iron(III) chloride hexahydrate In hexane; water at 80℃; for 14h;81%
N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

m-Toluic acid
99-04-7

m-Toluic acid

Conditions
ConditionsYield
With niobium(V) oxide; water In neat (no solvent) for 24h; Reflux; Inert atmosphere;76%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

Trimethyl borate
121-43-7

Trimethyl borate

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

pinacolo[2-(N,N-diethylcarboxamido)-4-methylphenyl]boronate
698376-34-0

pinacolo[2-(N,N-diethylcarboxamido)-4-methylphenyl]boronate

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In tetrahydrofuran (Ar); soln. of benzamide in THF was added dropwise to stirred soln. of s-BuLi/tetramethylethylenediamine (1/1) in THF at -78°C; mixt. wasstirred at -78°C for 1 h; treated with B(OMe)3; mixt. was warmed to room temp. over 8-12 h; quenched with satd. aq. NH4Cl; aq. phase extd. (Et2O); extract dried (Na2SO4); concd. (vac.); chromd. (silica gel, EtOAc/hexane); stirred with pinacol and MgSO4 in CH2Cl2 for 12 h; filtered; concd.; chromd. (silica gel, EtOAc/hexane, 1/3);70%
...Expand
N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

A

3-methylbenzyl alcohol
587-03-1

3-methylbenzyl alcohol

B

m-tolyl aldehyde
620-23-5

m-tolyl aldehyde

Conditions
ConditionsYield
With titanium(IV) isopropylate; 1,1,3,3-Tetramethyldisiloxane In methyl cyclohexane at 20℃; for 15h; Inert atmosphere;A Ca. 10 %Spectr.
B 70%
Triethoxyvinylsilane
78-08-0

Triethoxyvinylsilane

N,N-Diethyl-3-methylbenzamide
134-62-3

N,N-Diethyl-3-methylbenzamide

C14H19NO

C14H19NO

Conditions
ConditionsYield
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; lithium fluoride In 1,2-dichloro-ethane at 120℃; for 36h; Schlenk technique;68%

N,N-Diethyl-3-methylbenzamide Chemical Properties

IUPAC Name: N,N-Diethyl-3-methylbenzamide
Synonyms of N,N-Diethyl-m-toluamide (CAS NO.134-62-3): N,N-Diethyl-3-methylbenzamide ; m-Toluic acid diethylamid
CAS NO: 134-62-3
Molecular Formula: C12H17NO
Molecular Weight: 191.27
Molecular Structure:
EINECS: 205-149-7
H bond acceptors: 2
H bond donors: 0
Freely Rotating Bonds: 3
Polar Surface Area: 20.31 Å2
Index of Refraction: 1.517
Molar Refractivity: 58.72 cm3
Molar Volume: 194 cm3
Surface Tension: 35.9 dyne/cm
Density: 0.985 g/cm3
Flash Point: 141.7 °C
Enthalpy of Vaporization: 53.73 kJ/mol
Boiling Point: 297.5 °C at 760 mmHg
Vapour Pressure: 0.00135 mmHg at 25°C
Water Solubility: negligible
Appearance: Colorless to Amberlike Liquid
SMILES: O=C(c1cc(ccc1)C)N(CC)CC
InChI: InChI=1/C12H17NO/c1-4-13(5-2)12(14)11-8-6-7-10(3)9-11/h6-9H,4-5H2,1-3H3
InChIKey: MMOXZBCLCQITDF-UHFFFAOYAE
Std. InChI: InChI=1S/C12H17NO/c1-4-13(5-2)12(14)11-8-6-7-10(3)9-11/h6-9H,4-5H2,1-3H3
Std. InChIKey: MMOXZBCLCQITDF-UHFFFAOYSA-N
Product Categories of N,N-Diethyl-m-toluamide (CAS NO.134-62-3): INORGANIC & ORGANIC CHEMICALS;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Organics;Amines;Aromatics;Isotope Labeled Compounds;Alphabetic;D;DID - DINPesticides&Metabolites;Others;Pesticides
Stability: Stable. Combustible. Incompatible with strong oxidizing agents, strong acids, strong bases. Hydrolyzes slowly in water.

N,N-Diethyl-3-methylbenzamide Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 4750mg/kg (4750mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: STIFFNESS

BEHAVIORAL: COMA		 JAMA, Journal of the American Medical Association. Vol. 258, Pg. 1509, 1987.
human TDLo skin 35mg/kg/5D (35mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Toxicology and Applied Pharmacology. Vol. 1, Pg. 97, 1959.
mammal (species unspecified) LD50 oral 1800mg/kg (1800mg/kg)   United States Patent Document. Vol. #3594481,
man LDLo oral 679mg/kg (679mg/kg)   JAMA, Journal of the American Medical Association. Vol. 258, Pg. 1509, 1987.
mouse LD50 oral 1170mg/kg (1170mg/kg)   Yakkyoku. Pharmacy. Vol. 36, Pg. 1671, 1985.
mouse LD50 skin 3170uL/kg (3.17mL/kg)   Yakkyoku. Pharmacy. Vol. 31, Pg. 309, 1980.
rabbit LD50 oral 1584mg/kg (1584mg/kg)   National Technical Information Service. Vol. AD-A082-131,
rabbit LD50 oral 1584mg/kg (1584mg/kg)   National Technical Information Service. Vol. AD-A082-131,
rabbit LD50 skin 3180uL/kg (3.18mL/kg)   Toxicology and Applied Pharmacology. Vol. 28, Pg. 313, 1974.
rabbit LDLo intravenous 75mg/kg (75mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: TREMOR		 Toxicology and Applied Pharmacology. Vol. 1, Pg. 97, 1959.
rat LC50 inhalation 5950mg/m3 (5950mg/m3)   National Technical Information Service. Vol. AD-079-960,
rat LD50 oral 1950mg/kg (1950mg/kg)   Special Publication of the Entomological Society of America. Vol. 78-1, Pg. 53, 1978.
rat LD50 skin 5gm/kg (5000mg/kg)   Meditsinskaya Parazitologiya i Parazitarnye Bolezni. Medical Parasitology and Parasitic Diseases. Vol. 45, Pg. 65, 1976.
women LDLo oral 950mg/kg (950mg/kg) BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

GASTROINTESTINAL: NAUSEA OR VOMITING		 JAMA, Journal of the American Medical Association. Vol. 258, Pg. 1509, 1987.
women TDLo oral 300ug/kg (0.3mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION		 Journal of Analytical Toxicology. Vol. 19, Pg. 197, 1995.
women TDLo oral 950mg/kg (950mg/kg) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 JAMA, Journal of the American Medical Association. Vol. 258, Pg. 1509, 1987.
 

N,N-Diethyl-3-methylbenzamide Consensus Reports

Reported in EPA TSCA Inventory.

N,N-Diethyl-3-methylbenzamide Safety Profile

Safety Information about N,N-Diethyl-m-toluamide (CAS NO.134-62-3):
Hazard Codes: HarmfulXn
Risk Statements: 22-36/38-52/53
R22: Harmful if swallowed. 
R36/38: Irritating to eyes and skin. 
R52/53: Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 61
S21:When using do not smoke.
RIDADR: 2810
WGK Germany: 2
RTECS: XS3675000
HazardClass: 6.1(b)
PackingGroup: III
HS Code: 29242995
Poison by intravenous route. Moderately toxic by ingestion and skin contact. Human systemic effects: coma, convulsions, dermatitis, mydriasis (pupillary dilation), nausea or vomiting, stiffness. An eye and skin irritant. Experimental reproductive effects by skin contact. Mutation data reported. Can cause central nervous system disturbances. A pesticide. DEET is the active ingredient in most commercial insect repellents. When heated to decomposition DIETHYL-m-TOLUAMIDE (134-62-3) emits toxic fumes of NOx.

N,N-Diethyl-3-methylbenzamide Specification

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam. 
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Store in a cool, dry place. Store in a tightly closed container.

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