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527-85-5 Usage

Uses

2-Methylbenzamide (o-Toluamide) has been used in total synthesis of phenolic protoberberine alkaloid, cerasonine.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 2, p. 586, 1943The Journal of Organic Chemistry, 57, p. 2700, 1992 DOI: 10.1021/jo00035a030

General Description

White powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

O-TOLUAMIDE is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).

Health Hazard

ACUTE/CHRONIC HAZARDS: O-TOLUAMIDE may react violently if exposed to open flame; it should be isolated from all sources of ignition.

Fire Hazard

Flash point data for O-TOLUAMIDE are not available, however O-TOLUAMIDE is probably combustible.

Purification Methods

Crystallise o-toluamide from hot water (10mL/g) and dry in air. [Noller Org Synth Coll Vol II 586 1943, Beilstein 9 H 465, 9 II 319, 9 III 2304.]

Check Digit Verification of cas no

The CAS Registry Mumber 527-85-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,2 and 7 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 527-85:
(5*5)+(4*2)+(3*7)+(2*8)+(1*5)=75
75 % 10 = 5
So 527-85-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H9NO/c1-6-4-2-3-5-7(6)8(9)10/h2-5H,1H3,(H2,9,10)

527-85-5SDS

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 O-TOLUAMIDE

1.2 Other means of identification

Product number -
Other names 2-METHYLBENZAMIDE

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:527-85-5 SDS

527-85-5Synthetic route

2-Methylbenzonitrile
529-19-1

2-Methylbenzonitrile

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With C18H57O3P6Ru2(1+)*C6H5O(1-)*C6H6O; water In 1,4-dioxane for 24h; Time; Sealed tube; Inert atmosphere; Schlenk technique;99%
With sodium hydroxide; dihydrogen peroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane for 1.6h; Ambient temperature;97%
With water; sodium carbonate; tricyclohexylphosphine; {Rh(OMe)(cod)}2 In isopropyl alcohol at 25℃; for 24h;96%
o-methylbenzoyl bromide
20045-96-9

o-methylbenzoyl bromide

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
Stage #1: o-methylbenzoyl bromide With aluminum isopropoxide; dimethyl amine In Cyclooctan at 36℃; for 3h;
Stage #2: With potassium sulfate; zinc 2-ethylhexanoate at 47℃; for 3.16667h; Temperature;
98.8%
ortho-methylbenzoic acid
118-90-1

ortho-methylbenzoic acid

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
Stage #1: ortho-methylbenzoic acid With 1,3,5-trichloro-2,4,6-triazine; potassium carbonate In tetrahydrofuran for 0.0166667h; Milling;
Stage #2: With ammonium thiocyanate In tetrahydrofuran for 0.0833333h; Milling;
98%
With ammonium hydroxide In ethyl acetate at 40℃; for 16h; Solvent; Temperature; Reagent/catalyst; Large scale; Green chemistry;97.7%
Multi-step reaction with 2 steps
1: phosphorus pentachloride / 120 °C
View Scheme
salicylaldoxime
14683-79-5

salicylaldoxime

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With C55H45ClN5P2Ru(1+)*Cl(1-) In water at 110℃; for 12h; Sealed tube;98%
With [PdCl2{κ2-(P,N)-2-Ph2PC6H4CH=NOH}] In water at 100℃; for 24h; Inert atmosphere; Sealed tube;90%
With [RuCl2(η2-C6H6){P(NMe2)3}]; water at 100℃; for 7h; Inert atmosphere; Sealed tube;87%
With cis,cis,trans-[RuCl2{κ2-(P,N)-2-Ph2PC6H4CH=NOH}2] In water at 100℃; for 12h; Sealed tube; Inert atmosphere;82%
With zinc(II) chloride In n-heptane for 18h; Reflux;
2-methyl-benzyl alcohol
89-95-2

2-methyl-benzyl alcohol

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; silver trifluoroacetate; phenylhydrazine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In N,N-dimethyl-formamide at 70℃; for 12h; Reagent/catalyst; Solvent;96.6%
With tert.-butylhydroperoxide; ammonia; oxygen In water; N,N-dimethyl-formamide at 80℃; under 1520.1 Torr; for 5h; Green chemistry;89%
With tert.-butylhydroperoxide; ammonium hydroxide In water at 100℃; for 16h;87%
With tert.-butylhydroperoxide; tetraethylammonium iodide; ammonium bicarbonate In 1,2-dichloro-ethane at 70℃; for 22h;69%
2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With hydroxylamine; C33H28F3N5O3Ru(1+)*Cl(1-) In water at 60℃; for 0.5h; Catalytic behavior; Sonication;96%
With C17H17BrClN2RuSe(1+)*F6P(1-); hydroxylamine hydrochloride; sodium hydroxide In toluene at 100℃; for 12h; Reagent/catalyst; Solvent; Temperature;94%
With tert.-butylhydroperoxide; titanium superoxide; saccharin In 1,4-dioxane; hexane at 90℃; for 1h; Green chemistry;91%
ortho-methylbenzylamine
89-93-0

ortho-methylbenzylamine

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); potassium tert-butylate In tert-butyl alcohol at 70℃; for 12h;95%
With tetra(n-butyl)ammonium hydroxide In water at 70℃; for 12h; Green chemistry;89%
With potassium tert-butylate; C36H24N2O12Ru3 In tert-butyl alcohol for 10h; Reflux;83%
ortho-toluoyl chloride
933-88-0

ortho-toluoyl chloride

adenosine
58-61-7

adenosine

A

pyridine hydrochloride
628-13-7

pyridine hydrochloride

B

N6,2',3',5'-tetra-O-toluoyladenosine
104579-36-4

N6,2',3',5'-tetra-O-toluoyladenosine

C

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With methanol; ammonia In pyridine at 0℃;A n/a
B 93%
C n/a
ortho-methylphenyl iodide
615-37-2

ortho-methylphenyl iodide

carbon monoxide
201230-82-2

carbon monoxide

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; N-methoxylamine hydrochloride; sodium iodide; palladium dichloride In acetonitrile at 90℃; under 3800.26 Torr; for 8h; Autoclave; Inert atmosphere;93%
With 1,4-diaza-bicyclo[2.2.2]octane; palladium 10% on activated carbon; ammonium carbamate; potassium iodide In acetonitrile at 90℃; for 8h; Autoclave; Green chemistry;88%
With dichloro bis(acetonitrile) palladium(II); ammonium bicarbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In acetonitrile at 120℃; under 7500.75 Torr; for 3h; Autoclave;> 99 %Chromat.
formic acid
64-18-6

formic acid

ortho-methylphenyl iodide
615-37-2

ortho-methylphenyl iodide

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With palladium diacetate; ammonium bicarbonate; dicyclohexyl-carbodiimide; triphenylphosphine In acetonitrile at 100℃; Inert atmosphere;93%
2-Methylbenzonitrile
529-19-1

2-Methylbenzonitrile

A

ortho-methylbenzoic acid
118-90-1

ortho-methylbenzoic acid

B

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With phosphate buffer at 30℃; for 5.5h; rhodococcus rhodocrous AJ270, pH 7.0;A 7%
B 92%
With potassium phosphate buffer at 30℃; for 5.5h; Rhodococcus sp. AJ270 cells;A 6.6%
B 92.4%
2-Methylacetophenone
577-16-2, 122382-54-1

2-Methylacetophenone

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With ammonia; water; iodine In tetrahydrofuran at 20℃; for 1h; Haller-Bauer reaction;92%
With tert.-butylhydroperoxide; ammonia; tetra-(n-butyl)ammonium iodide In water at 100℃; for 16h; Green chemistry;51%
(Z)-2-methylbenzaldoxime
127459-91-0

(Z)-2-methylbenzaldoxime

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With aluminum oxide; methanesulfonic acid at 140℃; for 3h; Beckmann rearrangement;90%
ortho-methylphenyl iodide
615-37-2

ortho-methylphenyl iodide

potassium ferrocyanide

potassium ferrocyanide

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With water; potassium carbonate In dimethyl sulfoxide at 110℃; for 12h;90%
carbon monoxide
201230-82-2

carbon monoxide

2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); (2R)-1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene; ammonium carbamate; sodium hydrogencarbonate In 1,4-dioxane at 100℃; for 20h; Inert atmosphere;86%
With 2-(2'-pyridyl)(di(1-adamantyl)phosphino)benzene; ammonia; palladium diacetate In 1,4-dioxane at 120℃; under 1500.15 Torr; for 16h; Autoclave;70%
With ammonia; palladium diacetate; catacxium A In 1,4-dioxane at 100℃; under 3000.3 Torr; for 16h; Autoclave;90 %Chromat.
With 1,1'-bis-(diphenylphosphino)ferrocene; ammonia; palladium diacetate In 1,4-dioxane at 100℃; under 1500.15 Torr; for 16h;98 %Chromat.
ortho-methylphenyl iodide
615-37-2

ortho-methylphenyl iodide

Mo(CO)6

Mo(CO)6

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With hydroxylamine hydrochloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane at 110℃; for 0.333333h; microwave irradiation;84%
ortho-methylbenzylamine
89-93-0

ortho-methylbenzylamine

A

2-Methylbenzonitrile
529-19-1

2-Methylbenzonitrile

B

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With ammonium hydroxide; oxygen In tert-Amyl alcohol at 110℃; under 1500.15 Torr; for 16h;A 82.8%
B 10.4%
2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

Mo(CO)6

Mo(CO)6

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With hydroxylamine hydrochloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane at 150℃; for 0.333333h; microwave irradiation;78%
(R)-2-amino-3-(((2-methylbenzoyl)carbamothioyl)thio)propanoic acid
1628342-24-4

(R)-2-amino-3-(((2-methylbenzoyl)carbamothioyl)thio)propanoic acid

A

(4R)-2-sulfanylidene-1,3-thiazolidine-4-carboxylic acid
98169-56-3

(4R)-2-sulfanylidene-1,3-thiazolidine-4-carboxylic acid

B

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
In water for 1h; Reflux;A n/a
B 76%
o-xylene
95-47-6

o-xylene

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; iron(III) chloride hexahydrate; tetrabutylammonium iodide; ammonium hydroxide In water at 80℃; for 18h; Sealed tube;76%
C19H23N3O2

C19H23N3O2

A

isonicotinoyl-tert-butylformamide

isonicotinoyl-tert-butylformamide

B

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With copper diacetate; palladium diacetate In water at 120℃; for 1h; Reagent/catalyst; Schlenk technique; Green chemistry;A 48%
B 75%
2-Ethyltoluene
611-14-3

2-Ethyltoluene

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; ammonia; iodine In water at 100℃; for 3h; Sealed tube; Green chemistry;73%
2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

A

2-Methylbenzonitrile
529-19-1

2-Methylbenzonitrile

B

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With [Ru(η6-C6Me6)Cl2(tris(dimethylamino)phosphine)]; hydroxylamine hydrochloride; sodium hydrogencarbonate In water at 100℃; for 7h; Inert atmosphere; Sealed tube; Green chemistry;A n/a
B 71%
2-tolylmethylnitrile
22364-68-7

2-tolylmethylnitrile

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; ammonium hydroxide; iodine In acetonitrile at 70℃; for 36h; Sealed tube;70%
With copper(I) oxide; oxygen; ammonium chloride; sodium hydroxide In acetonitrile at 120℃; under 760.051 Torr; for 48h; Schlenk technique;35%
N-<(4-Methylphenyl)sulfonyl>-2-methylbenzenecarboxamide
146448-53-5

N-<(4-Methylphenyl)sulfonyl>-2-methylbenzenecarboxamide

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With tetraethylammonium bromide In N,N-dimethyl-formamide at 20℃;69%
ortho-toluoyl chloride
933-88-0

ortho-toluoyl chloride

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With ammonia Inert atmosphere;62%
With ammonium hydroxide; diethyl ether
With ammonium hydroxide In tetrahydrofuran at 20℃; for 2h;
N-phenyl-2-(2-methylphenyl)formamidine
32622-24-5

N-phenyl-2-(2-methylphenyl)formamidine

benzyl alcohol
100-51-6

benzyl alcohol

A

N-Benzylaniline
758640-21-0

N-Benzylaniline

B

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With potassium hydroxide In toluene at 120℃; for 15h; Schlenk technique; Glovebox; Inert atmosphere; Sealed tube;A 62 %Chromat.
B 58%
2-methyl-N-phenyl-N-tosylbenzamide

2-methyl-N-phenyl-N-tosylbenzamide

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With ammonium carbonate In dimethyl sulfoxide at 25℃; for 6h;51%
1-methyl-2-vinyl-benzene
611-15-4

1-methyl-2-vinyl-benzene

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; ammonia In water at 105℃; for 16h;50%
methanol
67-56-1

methanol

o-Methylbenzamid
527-85-5

o-Methylbenzamid

methyl N-(2-methylphenyl)carbamate
14983-92-7

methyl N-(2-methylphenyl)carbamate

Conditions
ConditionsYield
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; silver(I) acetate In N,N-dimethyl-formamide for 12h; Ambient temperature; or Hg(OAc)2, NBS-Hg(OAc)2;100%
With tetra-N-butylammonium tribromide; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 1.5h; Ambient temperature;97%
With sodium bromide In acetonitrile at 50℃; for 6h; Hofmann Rearrangement; Electrochemical reaction; Green chemistry;93%
o-Methylbenzamid
527-85-5

o-Methylbenzamid

2-Methyl-1,4-benzoquinone
553-97-9

2-Methyl-1,4-benzoquinone

Conditions
ConditionsYield
With iodobenzene; oxone; water In acetonitrile at 20℃;100%
With sodium hydrogen sulfate; [bis(acetoxy)iodo]benzene In water; acetonitrile at 20℃; for 0.583333h;85%
o-Methylbenzamid
527-85-5

o-Methylbenzamid

2-Methylbenzonitrile
529-19-1

2-Methylbenzonitrile

Conditions
ConditionsYield
With per-rhenic acid In water; 1,3,5-trimethyl-benzene for 24h; Heating;99%
With per-rhenic acid In water; 1,3,5-trimethyl-benzene for 24h; Heating;97%
With iron(II) chloride tetrahydrate; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide In tetrahydrofuran at 70℃; for 2h;96%
o-Methylbenzamid
527-85-5

o-Methylbenzamid

5-iodo-2-methylbenzamide

5-iodo-2-methylbenzamide

Conditions
ConditionsYield
With N-iodo-succinimide; trifluoroacetic acid at 20℃; for 3h; regioselective reaction;99%
o-Methylbenzamid
527-85-5

o-Methylbenzamid

3-amido-4-methylbenzenesulfonyl chloride
76503-37-2

3-amido-4-methylbenzenesulfonyl chloride

Conditions
ConditionsYield
With chlorosulfonic acid at 70℃; for 2h;98%
triphenylphosphine
603-35-0

triphenylphosphine

o-Methylbenzamid
527-85-5

o-Methylbenzamid

N-o-toluoyltriphenylphospha-λ5-azene
95978-80-6

N-o-toluoyltriphenylphospha-λ5-azene

Conditions
ConditionsYield
With diethylazodicarboxylate In tetrahydrofuran at 0 - 25℃; for 12h;97%
o-Methylbenzamid
527-85-5

o-Methylbenzamid

2-methyl-benzyl alcohol
89-95-2

2-methyl-benzyl alcohol

Conditions
ConditionsYield
With samarium diiodide; water In tetrahydrofuran for 0.00277778h; Ambient temperature;96%
With C24H20ClN2OPRu; potassium tert-butylate; hydrogen In tetrahydrofuran at 110℃; under 10640.7 Torr; for 36h; Inert atmosphere; Schlenk technique;85%
With sodium amalgam; ethanol
chloral hydrate
302-17-0

chloral hydrate

o-Methylbenzamid
527-85-5

o-Methylbenzamid

N-(2,2,2-trichloro-1-hydroxyethyl)-2-methylbenzamide
51361-17-2

N-(2,2,2-trichloro-1-hydroxyethyl)-2-methylbenzamide

Conditions
ConditionsYield
at 90 - 100℃;95%
Heating;
6-bromo-2-(2-methoxyethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
651768-37-5

6-bromo-2-(2-methoxyethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

o-Methylbenzamid
527-85-5

o-Methylbenzamid

N-(2-(2-methoxyethyl)-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)-2-methylbenzamide

N-(2-(2-methoxyethyl)-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)-2-methylbenzamide

Conditions
ConditionsYield
With palladium [2'-(amino-κN)[1,1'-biphenyl]-2-yl-κC][[5-(diphenylphosphino)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphine-κP](methanesulfonato-κO); caesium carbonate In 1,4-dioxane at 100℃; for 1.66667h; Inert atmosphere;95%
1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

o-Methylbenzamid
527-85-5

o-Methylbenzamid

N-(diphenylmethyl)-2-methylbenzamide
10254-11-2

N-(diphenylmethyl)-2-methylbenzamide

Conditions
ConditionsYield
With Bromodiphenylmethane In neat (no solvent) at 130℃; for 24h; Temperature; Sealed tube; Green chemistry;94%
With silica perchloric acid In 1,4-dioxane for 5h; Reflux;82%
o-Methylbenzamid
527-85-5

o-Methylbenzamid

o-tolylmethanamine monohydrochloride
14865-38-4

o-tolylmethanamine monohydrochloride

Conditions
ConditionsYield
Stage #1: o-Methylbenzamid With bis(cyclopentadienyl)dihydrozirconium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane at 20℃; under 760.051 Torr; for 24h; Inert atmosphere;
Stage #2: With hydrogenchloride In diethyl ether Inert atmosphere;
93%
Stage #1: o-Methylbenzamid With [(aNHC)KN(SiMe3)2]2; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In toluene at 40℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique;
Stage #2: With water; sodium hydroxide In diethyl ether; toluene at 40℃; for 1h; Inert atmosphere; Glovebox; Schlenk technique;
Stage #3: With hydrogenchloride In diethyl ether; water Inert atmosphere; Glovebox; Schlenk technique;
89%
Stage #1: o-Methylbenzamid With phenylsilane; C28H18ClMnN2O2; potassium tert-butylate In tetrahydrofuran at 50℃; for 12h; Inert atmosphere; Glovebox;
Stage #2: With sodium hydroxide In tetrahydrofuran for 3h; Inert atmosphere; Glovebox;
Stage #3: With hydrogenchloride In methanol; diethyl ether Glovebox; Inert atmosphere;
84%
Yield given. Multistep reaction;
benzo[d][1,3]dioxol-5-yl methanesulfonate
128612-45-3

benzo[d][1,3]dioxol-5-yl methanesulfonate

o-Methylbenzamid
527-85-5

o-Methylbenzamid

Conditions
ConditionsYield
With t-BuBrettPhos; water; palladium diacetate; caesium carbonate In tert-butyl alcohol at 110℃; for 2h; Inert atmosphere;93%
o-Methylbenzamid
527-85-5

o-Methylbenzamid

9-methyl-5,6,13-triphenyl-8H-dibenzo[a,g]quinolizin-8-one
1253388-66-7

9-methyl-5,6,13-triphenyl-8H-dibenzo[a,g]quinolizin-8-one

Conditions
ConditionsYield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver carbonate In acetonitrile at 115℃; for 10h; Inert atmosphere;93%
tetramethylammonium fluoride
373-68-2

tetramethylammonium fluoride

o-Methylbenzamid
527-85-5

o-Methylbenzamid

N,N,2-trimethylbenzamide
6639-19-6

N,N,2-trimethylbenzamide

Conditions
ConditionsYield
In toluene at 100℃; for 12h;93%
2,3-dichloropyrazine
4858-85-9

2,3-dichloropyrazine

o-Methylbenzamid
527-85-5

o-Methylbenzamid

2-(ortho-tolyl)oxazolo[4,5-b]pyrazine

2-(ortho-tolyl)oxazolo[4,5-b]pyrazine

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 110℃; for 4h; Inert atmosphere; Sealed tube;92%
2,2,2-trifluoroethyl acrylate
407-47-6

2,2,2-trifluoroethyl acrylate

o-Methylbenzamid
527-85-5

o-Methylbenzamid

2,2,2-trifluoroethyl (Z)-2-(4-methyl-3-oxoisoindolin-1-ylidene)acetate

2,2,2-trifluoroethyl (Z)-2-(4-methyl-3-oxoisoindolin-1-ylidene)acetate

Conditions
ConditionsYield
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate In tert-Amyl alcohol at 20 - 100℃; for 12.33h; Schlenk technique; Sealed tube; regioselective reaction;92%
2-chloropyridine
109-09-1

2-chloropyridine

o-Methylbenzamid
527-85-5

o-Methylbenzamid

2-methyl-N-(pyridin-2-yl)benzamide
35498-29-4

2-methyl-N-(pyridin-2-yl)benzamide

Conditions
ConditionsYield
With tri(sec-butyl)borane; (DiMeIHeptCl)Pd(cinammyl)Cl; caesium carbonate In toluene at 80℃; for 24h; Inert atmosphere; Sealed tube; Schlenk technique;92%

527-85-5Relevant articles and documents

Nitrogen Atom Transfer Catalysis by Metallonitrene C?H Insertion: Photocatalytic Amidation of Aldehydes

Schmidt-R?ntsch, Till,Verplancke, Hendrik,Lienert, Jonas N.,Demeshko, Serhiy,Otte, Matthias,Van Trieste, Gerard P.,Reid, Kaleb A.,Reibenspies, Joseph H.,Powers, David C.,Holthausen, Max C.,Schneider, Sven

, (2022/01/20)

C?H amination and amidation by catalytic nitrene transfer are well-established and typically proceed via electrophilic attack of nitrenoid intermediates. In contrast, the insertion of (formal) terminal nitride ligands into C?H bonds is much less developed and catalytic nitrogen atom transfer remains unknown. We here report the synthesis of a formal terminal nitride complex of palladium. Photocrystallographic, magnetic, and computational characterization support the assignment as an authentic metallonitrene (Pd?N) with a diradical nitrogen ligand that is singly bonded to PdII. Despite the subvalent nitrene character, selective C?H insertion with aldehydes follows nucleophilic selectivity. Transamidation of the benzamide product is enabled by reaction with N3SiMe3. Based on these results, a photocatalytic protocol for aldehyde C?H trimethylsilylamidation was developed that exhibits inverted, nucleophilic selectivity as compared to typical nitrene transfer catalysis. This first example of catalytic C?H nitrogen atom transfer offers facile access to primary amides after deprotection.

Half-Sandwich Iridium Complexes Based on β-Ketoamino Ligands: Preparation, Structure, and Catalytic Activity in Amide Synthesis

Wang, Yang,Guo, Wen,Guan, Ai-Lin,Liu, Shuang,Yao, Zi-Jian

, p. 11514 - 11520 (2021/07/31)

A series of β-ketoamino-based N,O-chelate half-sandwich iridium complexes with the general formula [Cp*IrClL] have been prepared in good yields. These air-insensitive iridium complexes showed desirable catalytic activity in an amide preparation under mild conditions. A number of amides with diverse substituted groups were furnished in a one-pot reaction with good-to-excellent yields through an amidation reaction of NH2OH·HCl with aldehydes in the presence of these iridium(III) precursors. The excellent catalytic activity, mild reaction conditions, and broad substrate scope gave this type of iridium catalyst potential for use in industry. All of the obtained iridium complexes were well characterized by different spectroscopy techniques. The exact molecular structure of complex 3 has been confirmed by single-crystal X-ray analysis.

Efficient nitriding reagent and application thereof

-

Paragraph 0315-0317, (2021/03/31)

The invention discloses an efficient nitriding reagent and application thereof, wherein the nitriding reagent comprises nitrogen oxide, an active agent, a reducing agent and an organic solvent. By applying the nitriding reagent, nitrogen-containing compounds such as amide, nitrile and the like can be produced, and the method is simple in condition, low in waste discharge amount and simple in reaction equipment.

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