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99-08-1 Usage

Safety Profile

Poison by ingestion. Moderatelytoxic by inhalation. Combustible when exposed to heat,flame, or oxidizers. To fight fire, use water, CO2, drychemical. Probably an explosive. When heated todecomposition it emits toxic fumes of NOx.

Check Digit Verification of cas no

The CAS Registry Mumber 99-08-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 9 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 99-08:
(4*9)+(3*9)+(2*0)+(1*8)=71
71 % 10 = 1
So 99-08-1 is a valid CAS Registry Number.

99-08-1 Well-known Company Product Price

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  • Supelco

  • (442394)  3-Nitrotoluene  analytical standard

  • 99-08-1

  • 000000000000442394

  • 259.74CNY

  • Detail
  • Supelco

  • (47241)  3-Nitrotoluenesolution  1000 μg/mL in acetonitrile, analytical standard

  • 99-08-1

  • 000000000000047241

  • 372.06CNY

  • Detail
  • Sigma-Aldrich

  • (45986)  3-Nitrotoluene  analytical standard

  • 99-08-1

  • 45986-250MG

  • 324.09CNY

  • Detail
  • Aldrich

  • (N27314)  3-Nitrotoluene  99%

  • 99-08-1

  • N27314-100G

  • 259.74CNY

  • Detail

99-08-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-nitrotoluene

1.2 Other means of identification

Product number -
Other names 3-Nitrotoluene

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:99-08-1 SDS

99-08-1Synthetic route

1-bromomethyl-3-nitrobenzene
3958-57-4

1-bromomethyl-3-nitrobenzene

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
With sodium tetrahydroborate; sodium hydroxide In water at 60℃; for 1.5h; pH=12; Reagent/catalyst; Green chemistry;99%
With diethylzinc; tetrakis(triphenylphosphine) palladium(0) In hexane; N,N-dimethyl-formamide at 25℃; for 1h;63%
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 1.5h;72 % Turnov.
m-tolylboronic acid
17933-03-8

m-tolylboronic acid

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
With dipotassium peroxodisulfate; bismuth (III) nitrate pentahydrate In toluene at 80℃; for 12h; Inert atmosphere;96%
With N-Bromosuccinimide; [bis(trifluoroacetoxy)iodo]benzene; sodium nitrite In acetonitrile at 20℃; for 3h; Solvent; regioselective reaction;93%
With pyridine; copper(I) oxide; sodium nitrite In acetonitrile at 20℃;78%
1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
With 1,9-diperoxynonanedioic acid In acetonitrile at 50℃; for 0.5h;95%
With dihydrogen peroxide; acetonitrile In aq. buffer at 20℃; for 1h; pH=11; Green chemistry;88%
With sodium perborate tetrahydrate; cetyltrimethylammonim bromide In water at 60℃; for 12h; silica gel; Micellar solution; Green chemistry; regioselective reaction;53%
With sulfuric acid Diazotization.Behandlung der neutralisierten Diazoniumsalz-Loesung mit NaNO2 und Kupfer(I)-kupfer(II)-sulfit;
With sulfuric acid Diazotization.Behandlung der neutralisierten Diazoniumsalz-Loesung mit NaNO2, CuSO4 und Cu2O;
C12H9N3O6S2

C12H9N3O6S2

tetramethylstannane
594-27-4

tetramethylstannane

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
palladium diacetate In tetrahydrofuran at 40℃; for 0.25h;90%
2-methyl-6-nitrobenzoic acid
13506-76-8

2-methyl-6-nitrobenzoic acid

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
With silver carbonate In dimethyl sulfoxide at 120℃; for 16h;86%
With silver carbonate In dimethyl sulfoxide at 120℃;
Multi-step reaction with 3 steps
1.1: sodium hydroxide / tetrahydrofuran; water / 0.17 h / Darkness
1.2: 0.08 h / Darkness
2.1: acetonitrile / 0.08 h / Darkness
3.1: water / d7-N,N-dimethylformamide / 2 h / 100 °C / Inert atmosphere; Glovebox; Sealed tube; Darkness
View Scheme
toluene
108-88-3

toluene

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
With nitric acid; sodium dodecyl-sulfate In acetonitrile at 24.84℃; for 3h; Micellar solution; regioselective reaction;85%
4-methyl-2-nitrobenzoic acid
27329-27-7

4-methyl-2-nitrobenzoic acid

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
With copper(l) iodide; triethylamine In dimethyl sulfoxide at 120℃; under 760.051 Torr; for 20h; Inert atmosphere; Schlenk technique;85%
With 1-methyl-pyrrolidin-2-one; quinoline; copper(I) oxide; 1,10-Phenanthroline at 100 - 175℃; for 0.5h; Inert atmosphere; Microwave irradiation;50%
Multi-step reaction with 3 steps
1: tetrahydrofuran / 2 h / 20 °C / Darkness
2: tetrahydrofuran / Darkness
3: water / d7-N,N-dimethylformamide / 0.83 h / 100 °C / Inert atmosphere; Glovebox; Sealed tube; Darkness
View Scheme
3-Iodotoluene
625-95-6

3-Iodotoluene

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
With copper; tetrabutylammonium nitrite; N,N`-dimethylethylenediamine In N,N-dimethyl-formamide at 110℃; for 0.333333h; Inert atmosphere; Microwave irradiation;84%
With copper bronze; tetrabutylammonium nitrate; N,N`-dimethylethylenediamine In N,N-dimethyl-formamide at 100℃;69%
With potassium nitrite; copper(II) bis(trifluoromethanesulfonate) In dimethyl sulfoxide at 130℃; for 48h; Inert atmosphere; Sealed tube; regioselective reaction;67%
N'-(3-nitrobenzylidene)-4-methylbenzenesulfonohydrazide
3748-99-0

N'-(3-nitrobenzylidene)-4-methylbenzenesulfonohydrazide

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
With dichloro bis(1,4-diazabicyclo[2.2.2]octane)(BH4)Zr(IV); toluene-4-sulfonic acid In sulfolane; N,N-dimethyl-formamide at 110℃; for 7.2h;83%
tetramethylstannane
594-27-4

tetramethylstannane

bis-(3-nitro-phenyl)-iodonium ; hydrogen sulfate

bis-(3-nitro-phenyl)-iodonium ; hydrogen sulfate

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
With palladium diacetate In water at 60 - 70℃; for 4h;80%
palladium diacetate In water at 60℃; for 4h;80 % Chromat.
toluene
108-88-3

toluene

A

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

B

1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

C

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

Conditions
ConditionsYield
With copper(II) nitrate on K10 montmorillonite; acetic anhydride In tetrachloromethane for 120h; Ambient temperature;A 1%
B 79%
C 20%
With nitric acid In trifluoroacetic acid at 25℃; Rate constant;A 0.7%
B 66.7%
C 32.6%
With ortho-methylphenyl iodide; potassium nitrate In trifluoroacetic acid for 0.5h; Product distribution; nitration of aromatic compounds in the presence of aryl iodides; other temperatures, other reagents;A n/a
B 64%
C 33%
tetramethylstannane
594-27-4

tetramethylstannane

bis(3-nitrophenyl)iodonium tetrafluoroborate

bis(3-nitrophenyl)iodonium tetrafluoroborate

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
With palladium diacetate In N,N-dimethyl-formamide at 60 - 70℃; for 2.5h;77%
palladium diacetate In N,N-dimethyl-formamide at 60℃; for 2h;77 % Chromat.
tetramethylstannane
594-27-4

tetramethylstannane

bis(3-nitrophenyl)iodonium trifluoroacetate

bis(3-nitrophenyl)iodonium trifluoroacetate

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
With palladium diacetate In N,N-dimethyl-formamide at 60 - 70℃; for 2.5h;77%
palladium diacetate In N,N-dimethyl-formamide at 60℃; for 2.5h;77 % Chromat.
2-methyl-4-nitrobenzoic acid
1975-51-5

2-methyl-4-nitrobenzoic acid

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
With [Au(1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene)(O2CAd)] In toluene at 140℃; for 20h;71%
diisopropyl hydrogenphosphonate
1809-20-7

diisopropyl hydrogenphosphonate

1-bromomethyl-3-nitrobenzene
3958-57-4

1-bromomethyl-3-nitrobenzene

A

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

B

diisopropyl (3-nitrophenyl)methyl phosphonate

diisopropyl (3-nitrophenyl)methyl phosphonate

Conditions
ConditionsYield
With sodium hydride In isopropyl alcohol for 3h; Ambient temperature;A 21%
B 69%
N-nitro-2,6-dimethylpyridinium tetrafluoroborate

N-nitro-2,6-dimethylpyridinium tetrafluoroborate

toluene
108-88-3

toluene

A

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

B

1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

C

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

Conditions
ConditionsYield
Product distribution; Ambient temperature;A 3%
B 32%
C 65%
tetramethylstannane
594-27-4

tetramethylstannane

m-nitrobenzenediazonium hexafluorophosphate
1514-51-8

m-nitrobenzenediazonium hexafluorophosphate

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
palladium diacetate In acetonitrile for 2h; Ambient temperature;62%
2-(3-nitrophenyl)acetaldehyde
66146-33-6

2-(3-nitrophenyl)acetaldehyde

A

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

B

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

C

3,3'-dinitrobibenzyl
19829-61-9

3,3'-dinitrobibenzyl

Conditions
ConditionsYield
In water; acetonitrile for 48h; Product distribution; Irradiation;A 60%
B 40%
C n/a
m-toluidine hydrochloride
638-03-9

m-toluidine hydrochloride

A

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

B

1-chloro-2-methyl-4-nitrobenzene
13290-74-9

1-chloro-2-methyl-4-nitrobenzene

Conditions
ConditionsYield
With 3,3-dimethyldioxirane In acetone at 20℃;A 45%
B 55%
2-iodo-5-nitrotoluene
5326-38-5

2-iodo-5-nitrotoluene

A

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

B

2,2'-dimethyl-4,4'-dinitro-biphenyl
59517-20-3

2,2'-dimethyl-4,4'-dinitro-biphenyl

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 12h; Catalytic behavior; Ullmann Condensation; Inert atmosphere; Green chemistry;A 10%
B 55%
1-bromomethyl-3-nitrobenzene
3958-57-4

1-bromomethyl-3-nitrobenzene

A

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

B

3,3'-dinitrobibenzyl
19829-61-9

3,3'-dinitrobibenzyl

C

diisopropyl (3-nitrophenyl)methyl phosphonate

diisopropyl (3-nitrophenyl)methyl phosphonate

Conditions
ConditionsYield
With diisopropyl phosphite; sodium hydride In tetrahydrofuran for 3h; Ambient temperature;A 5%
B 28%
C 52%
toluene
108-88-3

toluene

A

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

B

1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

C

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

D

2,4-dinitrotoluene
121-14-2

2,4-dinitrotoluene

Conditions
ConditionsYield
With trinitratooxovanadium(V) In dichloromethane for 0.05h; Ambient temperature; Further byproducts given;A 3%
B 47%
C 50%
D n/a
With trinitratooxovanadium(V) In dichloromethane for 0.1h; Ambient temperature; Further byproducts given;A 2%
B 41%
C 35%
D 19%
N,N-dimethyl-m-toluidine
121-72-2

N,N-dimethyl-m-toluidine

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
With tert.-butylhydroperoxide; ammonium iodide; water In dimethyl sulfoxide at 90℃; for 4h; Sealed tube;38%
toluene
108-88-3

toluene

A

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

B

1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

C

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

D

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In water; trifluoroacetic acid for 72h; Ambient temperature; Yield given;A n/a
B n/a
C n/a
D 24.5%
With nitric acid at 90 - 100℃; for 4h; Product distribution; Further Variations:; Temperatures; Reagents;
With nitrogen dioxide at 70℃; for 6h; Reagent/catalyst; Autoclave; Green chemistry;
dibenzylphosphine oxide
13238-16-9

dibenzylphosphine oxide

1-bromomethyl-3-nitrobenzene
3958-57-4

1-bromomethyl-3-nitrobenzene

A

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

B

3,3'-dinitrobibenzyl
19829-61-9

3,3'-dinitrobibenzyl

C

(3-nitrophenyl)methyl-dibenzyl-phosphine oxide

(3-nitrophenyl)methyl-dibenzyl-phosphine oxide

Conditions
ConditionsYield
With sodium hydride 1.) THF, 2.) THF, RT, 3 h; Yield given. Multistep reaction;A 2%
B 21%
C n/a
ethanol
64-17-5

ethanol

1,3-bis-(4-methyl-2-nitro-phenyl)-triazene

1,3-bis-(4-methyl-2-nitro-phenyl)-triazene

A

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

B

4-methyl-2-nitroaniline
89-62-3

4-methyl-2-nitroaniline

Conditions
ConditionsYield
at 170℃; im geschlossenen Rohr;
methyl radical
2229-07-4

methyl radical

nitrobenzene
98-95-3

nitrobenzene

A

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

B

1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

C

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

Conditions
ConditionsYield
at 143℃;
2-methyl-4-nitro-benzenamine
99-52-5

2-methyl-4-nitro-benzenamine

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
With hydrogenchloride Diazotization.Behandlung der Diazoniumsalz-Loesung mit wss.-alkal. Natriumstannit-Loesung bei -10grad;
Diazotization.Erwaermen des Diazoniumsulfats mit Alkohol;
With formamide; triethylamine; trifluoroacetic acid; sodium nitrite 1.) formamide/water, r.t.; 2.) water, r.t.; Yield given. Multistep reaction;
4-methyl-2-nitroaniline
89-62-3

4-methyl-2-nitroaniline

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
durch Entamidierung;
With hydrogenchloride Diazotization.Behandlung der Diazoniumsalz-Loesung mit H3PO2;
Diazotization.Kochen des Diazoniumsulfats mit absol. Alkohol;
1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

Conditions
ConditionsYield
With laccase from Coriolus versicolor MTCC-138; 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt In 1,4-dioxane for 1h; pH=4.5; Green chemistry; Enzymatic reaction;100%
With laccase at 20℃; Reagent/catalyst; Green chemistry; Enzymatic reaction;100%
With laccase of Pleurotus ostreatus MTCC-1801; 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt In 1,4-dioxane at 20℃; pH=4.5; Enzymatic reaction;98%
1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

Conditions
ConditionsYield
With [1-butyl-2,3-dimethylimidazolium][tppm] stabilized rhodium nanoarticles at 50℃; under 22502.3 Torr; for 5h; Ionic liquid; Autoclave; chemoselective reaction;100%
With cadmium sulphide; ammonium formate In water at 20℃; for 14h; Inert atmosphere; Irradiation; Sealed tube;100%
With water; oxalic acid; titanium(IV) oxide for 3h; Wavelength; Irradiation; Inert atmosphere; Sealed tube; Green chemistry; chemoselective reaction;100%
propyl cyanide
109-74-0

propyl cyanide

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

A

N-butyl-m-toluidine
60995-75-7

N-butyl-m-toluidine

B

N-butyl-N-(3-methyl-n-propyl)-m-toluidine
74878-72-1

N-butyl-N-(3-methyl-n-propyl)-m-toluidine

Conditions
ConditionsYield
Stage #1: 1-methyl-3-nitrobenzene With ammonium formate; palladium on activated charcoal In methanol; water at 20℃;
Stage #2: propyl cyanide In methanol; water
A 100%
B n/a
1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

butyraldehyde
123-72-8

butyraldehyde

N-butyl-m-toluidine
60995-75-7

N-butyl-m-toluidine

Conditions
ConditionsYield
With ammonium formate; palladium on activated charcoal In water; isopropyl alcohol at 20℃; for 1h;100%
1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

2,5-hexanedione
110-13-4

2,5-hexanedione

N-(3′-methylphenyl)-2,5-dimethylpyrrole
32570-10-8

N-(3′-methylphenyl)-2,5-dimethylpyrrole

Conditions
ConditionsYield
With formic acid for 12h; Autoclave; Inert atmosphere; Green chemistry;100%
With indium; acetic acid In toluene at 80℃; for 3h; Inert atmosphere;97%
1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

m-toluidine hydrochloride
638-03-9

m-toluidine hydrochloride

Conditions
ConditionsYield
Stage #1: 1-methyl-3-nitrobenzene With hydrogen In ethanol at 25℃; under 11172.7 Torr; Flow reactor;
Stage #2: With hydrogenchloride In ethanol Flow reactor; chemoselective reaction;
99%
With hydrogenchloride; tin(ll) chloride In ethanol; water at 30℃; Rate constant; Mechanism; various concentration of HCl;
Stage #1: 1-methyl-3-nitrobenzene With phosgene; sodium tetrahydroborate; copper(II) sulfate In methanol at 20℃;
Stage #2: With hydrogenchloride In methanol; diethyl ether
550 mg
1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

acetic anhydride
108-24-7

acetic anhydride

3-Methylacetanilide
537-92-8

3-Methylacetanilide

Conditions
ConditionsYield
With indium; acetic acid In methanol at 20℃; for 1h;99%
Stage #1: 1-methyl-3-nitrobenzene With sodium tetrahydroborate In water at 60 - 70℃; Green chemistry;
Stage #2: acetic anhydride In water at 60 - 70℃; Green chemistry;
94%
Stage #1: 1-methyl-3-nitrobenzene In water for 0.0833333h;
Stage #2: With sodium tetrahydroborate In water at 65℃; for 0.05h;
Stage #3: acetic anhydride In water at 65℃; for 0.0333333h; Catalytic behavior;
93%
tungsten hexacarbonyl
14040-11-0

tungsten hexacarbonyl

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

3-Methylacetanilide
537-92-8

3-Methylacetanilide

Conditions
ConditionsYield
With di(rhodium)tetracarbonyl dichloride; 1,3-bis-(diphenylphosphino)propane; sodium phosphate; sodium iodide In water at 120℃; for 24h; Inert atmosphere; Sealed tube;99%
1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

3,3'-dimethylazobenzene
588-04-5

3,3'-dimethylazobenzene

Conditions
ConditionsYield
With 1,3-bis(N',N'-dimethyl-4-aminopyridinium)propane diiodide; sodium hydride In N,N-dimethyl-formamide; paraffin oil at 20℃; for 0.25h; Inert atmosphere;98%
With potassium hydroxide In water; isopropyl alcohol at 35℃; under 760.051 Torr; for 8h; Inert atmosphere;95%
With Piperonyl butoxide; ammonium formate In methanol for 1.25h; Heating;94%
1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

5-(3-nitrophenyl)-1H-tetrazole
21871-44-3

5-(3-nitrophenyl)-1H-tetrazole

Conditions
ConditionsYield
With sodium azide; hydroxylamine hydrochloride In water at 20℃; for 4.16667h;97%
phenyl benzyl ketone
451-40-1

phenyl benzyl ketone

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

2-(3-methylphenyl)-1,2-diphenylethanone
123848-41-9

2-(3-methylphenyl)-1,2-diphenylethanone

Conditions
ConditionsYield
With potassium phosphate; bis(acetylacetonato)palladium(II); dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine In cyclohexane at 130℃; for 24h; Inert atmosphere;97%
formic acid
64-18-6

formic acid

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

N-formyl-m-toluidine
3085-53-8

N-formyl-m-toluidine

Conditions
ConditionsYield
With gold nano particles supported on rutile TiO2 In toluene at 70℃; under 750.075 Torr; for 3h; Inert atmosphere; chemoselective reaction;96%
With cobalt nanoparticles anchoring on nitrogen doped carbon, pyrolysis at 700 °C In acetonitrile at 110℃; under 750.075 Torr; for 5h; Inert atmosphere; chemoselective reaction;96.2%
With palladium(II) trifluoroacetate; triphenylphosphine In water at 80℃; for 0.333333h; Sealed tube; Green chemistry;92%
With [PdCl4]2-ion-exchanged imidazolium IL containing triethylene glycol-tagged onto silica-coated iron oxide nanoparticles In water at 90℃; for 24h; Inert atmosphere; Green chemistry;
With palladium particles distributed over the surface of fibrous silica nanospheres modified via aminopropyltriethoxysilane In toluene at 70℃; for 3h;98 %Chromat.
1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

N-(3-methylphenyl)hydroxylamine
620-25-7

N-(3-methylphenyl)hydroxylamine

Conditions
ConditionsYield
With methyldiazene In acetonitrile at 28℃; for 1.33333h; Irradiation; Sealed tube; Inert atmosphere;95%
With sodium tetrahydroborate; palladium diacetate In ethanol; dichloromethane; water at 20℃; for 0.0833333h;88%
With rhodium contaminated with carbon; hydrazine hydrate In tetrahydrofuran at 0 - 20℃; for 3h;85%
1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

A

1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

B

3,3'-dimethylhydrazobenzene
621-26-1

3,3'-dimethylhydrazobenzene

Conditions
ConditionsYield
With potassium hydroxide; aluminium In methanol at 20℃; for 0.25h; Reduction; Reductive coupling;A 3%
B 95%
formic acid
64-18-6

formic acid

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

N,N-dimethyl-m-toluidine
121-72-2

N,N-dimethyl-m-toluidine

Conditions
ConditionsYield
With hydrogen In toluene at 140℃; under 30003 Torr; for 3h; chemoselective reaction;95%
1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

3,3'-dimethylazoxybenzene
19618-06-5, 71297-97-7, 116723-90-1

3,3'-dimethylazoxybenzene

Conditions
ConditionsYield
With oxygen; ammonium chloride; zinc In [bmim][BF4]; water at 20℃; for 16h;94%
With potassium hydroxide In methanol; toluene for 24h; Heating;90%
Stage #1: 1-methyl-3-nitrobenzene With sodium tetrahydroborate; palladium diacetate In ethanol; dichloromethane; water at 20℃;
Stage #2: With oxygen In ethanol; dichloromethane; water
90%
1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

N-formyl-m-toluidine
3085-53-8

N-formyl-m-toluidine

Conditions
ConditionsYield
With cobalt nanoparticles coated by N,P-codoped carbon shell pyrolyzed at 800°C In tetrahydrofuran at 120℃; for 12h; Schlenk technique; Inert atmosphere;94%
With zinc for 0.05h; microwave irradiation;80%
1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

1-phenylpentane-1,4-dione
583-05-1

1-phenylpentane-1,4-dione

2-methyl-5-phenyl-1-m-tolyl-1H-pyrrole
357988-79-5

2-methyl-5-phenyl-1-m-tolyl-1H-pyrrole

Conditions
ConditionsYield
With indium; acetic acid In toluene for 0.5h; Inert atmosphere; Reflux;94%
1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

3-nitrobenzoic acid
121-92-6

3-nitrobenzoic acid

Conditions
ConditionsYield
With ruthenium trichloride; sodium hypochlorite; tetrabutylammomium bromide In 1,2-dichloro-ethane at 25℃; for 2h;93%
With chromium(VI) oxide; periodic acid In acetonitrile at 20℃; for 1h;93%
With oxygen; acetic acid; 1N,3N,5N-trihydroxy-1,3,5-triazin-2,4,6[1H,3H,5H]-trione; cobalt(II) acetate; manganese(II) acetate at 100℃; under 760 Torr; for 14h;88%
1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

trans-3,3'-dimethylazobenzene
51437-67-3

trans-3,3'-dimethylazobenzene

Conditions
ConditionsYield
With ammonium acetate; lead In methanol at 20℃;93%
With isopropyl alcohol; sodium hydroxide at 30℃; for 2h; Catalytic behavior; Inert atmosphere; UV-irradiation;88%
With ethanolamine; potassium hydroxide at 55℃; for 1h; Sonication; Microwave irradiation;88%
1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

benzaldehyde
100-52-7

benzaldehyde

N-benzyl-3-methylaniline
5405-17-4

N-benzyl-3-methylaniline

Conditions
ConditionsYield
With formic acid; Au/TiO2-R In water at 80℃; under 760.051 Torr; for 4h; Inert atmosphere; Green chemistry; chemoselective reaction;93%
With hydrogen In ethanol at 120℃; under 15001.5 Torr; for 8.5h; Autoclave;87%
Stage #1: 1-methyl-3-nitrobenzene With triethylsilane; palladium In methanol at 20℃; under 760.051 Torr; for 2h;
Stage #2: benzaldehyde In methanol
70%
methanol
67-56-1

methanol

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
With potassium tert-butylate at 130℃; for 24h; Sealed tube;93%
With [(N,N′-bis(diisopropylphosphino)-2,6-diaminopyridine)Mn(CO)3][Br]; potassium hydroxide at 110℃; for 16h; Molecular sieve; Sealed tube;80%
With [Ru(2-(6-methoxypyridin-2-yl)-1,10-phenanthroline)(MeCN)2Cl]Cl; sodium methylate at 110℃; for 12h; Green chemistry;87 %Chromat.
With platinum on carbon; potassium tert-butylate; hydrogen at 150℃; under 1500.15 Torr; for 24h; Autoclave;93 %Chromat.
1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

2,2,2-trifluoro-N-(2-iodophenyl)acetimidoyl chloride
1160967-80-5

2,2,2-trifluoro-N-(2-iodophenyl)acetimidoyl chloride

molybdenum hexacarbonyl
13939-06-5, 199620-15-0

molybdenum hexacarbonyl

3-(m–tolyl)-2-(trifluoromethyl)quinazolin-4(3H)-one

3-(m–tolyl)-2-(trifluoromethyl)quinazolin-4(3H)-one

Conditions
ConditionsYield
With 1,3-bis-(diphenylphosphino)propane; sodium carbonate; palladium dichloride In 1,4-dioxane at 120℃; for 24h; Inert atmosphere; Sealed tube;93%
1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

A

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

B

3-nitrobenzoic acid
121-92-6

3-nitrobenzoic acid

Conditions
ConditionsYield
With N-acetoxyphthalimide; cobalt(II) acetate; manganese(II) acetate In acetic acid at 130℃; under 7600 Torr; for 14h;A 5%
B 92%
With Coprinus sp. peroxidase; tartaric acid buffer; dihydrogen peroxide In water; acetone at 20℃; pH=5;
1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

ethyl cinnamate
4192-77-2

ethyl cinnamate

(2E)-N-(3-methylphenyl)-3-phenylprop-2-enamide

(2E)-N-(3-methylphenyl)-3-phenylprop-2-enamide

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran at 20℃; for 0.5h;92%
1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

cyclohexanone
108-94-1

cyclohexanone

3-Methyldiphenylamine
1205-64-7

3-Methyldiphenylamine

Conditions
ConditionsYield
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1-methyl-pyrrolidin-2-one at 150℃; for 24h; Inert atmosphere; Sealed vessel;92%
With N/O-doped porous carbon (on base of polypyrrole) supported nanopalladium at 80℃; Inert atmosphere;70%
1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

A

3,3'-dimethylazobenzene
588-04-5

3,3'-dimethylazobenzene

B

3,3'-dimethylazoxybenzene
19618-06-5, 71297-97-7, 116723-90-1

3,3'-dimethylazoxybenzene

Conditions
ConditionsYield
With sodium hydroxide; sodium tetrahydroborate; diphenyl ditelluride In ethanol for 20h; Heating;A 90%
B 10%
With sodium tetrahydroborate; water In ethanol at 30℃; for 3h; chemoselective reaction;A n/a
B 78%

99-08-1Relevant articles and documents

-

Roberts et al.

, p. 4285 (1958)

-

Photoinduced Iron-Catalyzed ipso-Nitration of Aryl Halides via Single-Electron Transfer

Wu, Cunluo,Bian, Qilong,Ding, Tao,Tang, Mingming,Zhang, Wenkai,Xu, Yuanqing,Liu, Baoying,Xu, Hao,Li, Hai-Bei,Fu, Hua

, p. 9561 - 9568 (2021/08/06)

A photoinduced iron-catalyzed ipso-nitration of aryl halides with KNO2 has been developed, in which aryl iodides, bromides, and some of aryl chlorides are feasible. The mechanism investigations show that the in situ formed iron complex by FeSO4, KNO2, and 1,10-phenanthroline acts as the light-harvesting photocatalyst with a longer lifetime of the excited state, and the reaction undergoes a photoinduced single-electron transfer (SET) process. This work represents an example for the photoinduced iron-catalyzed Ullmann-type couplings.

Niobium oxide prepared through a novel supercritical-CO2-assisted method as a highly active heterogeneous catalyst for the synthesis of azoxybenzene from aniline

Tao, Yehan,Singh, Bhawan,Jindal, Vanshika,Tang, Zhenchen,Pescarmona, Paolo P.

, p. 5852 - 5864 (2019/11/11)

High-surface area Nb2O5 nanoparticles were synthesised by a novel supercritical-CO2-assisted method (Nb2O5-scCO2) and were applied for the first time as a heterogeneous catalyst in the oxidative coupling of aniline to azoxybenzene using the environmentally friendly H2O2 as the oxidant. The application of scCO2 in the synthesis of Nb2O5-scCO2 catalyst resulted in a significantly enhanced catalytic activity compared to a reference catalyst prepared without scCO2 (Nb2O5-Ref) or to commercial Nb2O5. Importantly, the Nb2O5-scCO2 catalyst achieved an aniline conversion of 86% (stoichiometric maximum of 93% with the employed aniline-to-H2O2 ratio of 1?:?1.4) with an azoxybenzene selectivity of 92% and with 95% efficiency in H2O2 utilisation in 45 min without requiring external heating (the reaction is exothermic) and with an extremely low catalyst loading (weight ratio between the catalyst and substrate, Rc/s = 0.005). This performance largely surpasses that of any other heterogeneous catalyst previously reported for this reaction. Additionally, the Nb2O5 catalyst displayed high activity also for substituted anilines (e.g. methyl or ethyl-anilines and para-anisidine) and was reused in consecutive runs without any loss of activity. Characterisation by means of N2-physisorption, XRD, FTIR and TEM allowed the correlation of the remarkable catalytic performance of Nb2O5-scCO2 to its higher surface area and discrete nanoparticle morphology compared to the aggregated larger particles constituting the material prepared without scCO2. A catalytic test in the presence of a radical scavenger proved that the reaction follows a radical pathway.

Pd-poly(N-vinyl-2-pyrrolidone)/MCM-48 nanocomposite: a novel catalyst for the Ullmann reaction

Mosaddegh, Neda,Yavari, Issa

, p. 2013 - 2021 (2018/07/29)

Abstract: Homocoupling of aryl halides (Ullmann-type reaction) promoted by a Pd-poly(N-vinyl-2-pyrrolidone)/MCM-48 (Pd–PVP/MCM-48) nanocomposite catalyst is described. In situ polymerization method was employed to prepare composite poly(N-vinyl-2-pyrrolidone)/MCM-48 (PVP/MCM-48) which was used as a support for palladium nanoparticles obtained by reducing Pd(OAc)2 with hydrazine hydrate. FT-IR, XPS, XRD, UV–Vis, SEM, and BET techniques were used to study the chemical and physical properties of the catalyst. The catalytic performance of this heterogeneous catalyst was specified for Ullmann-type reaction between aryl halies in DMF. The catalyst was good with regard to its stability and it can be reused up to six times without significant loss of its activity.

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