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4-Chloro-2-nitrotoluene is an organic compound that is characterized by the presence of a chlorine atom at the 4-position and a nitro group at the 2-position on a toluene molecule. It is a versatile intermediate in the synthesis of various chemical compounds and has potential applications in different industries.

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  • 89-59-8 Structure
  • Basic information

    1. Product Name: 4-Chloro-2-nitrotoluene
    2. Synonyms: Toluene,4-chloro-2-nitro-;4-CHLORO-2-NITROTOLUENE;4-chloro-1-methyl-2-nitro-benzene;5-CHLORO-2-METHYLNITROBENZENE;2-Nitro-4-chlorotoluene;4-CHLORO-2-NITROTOLUENE OEKANAL, 250 MG;4-Chloro-2-nitrotoluene,99%;1-Chloro-4-methyl-3-nitrobenzene
    3. CAS NO:89-59-8
    4. Molecular Formula: C7H6ClNO2
    5. Molecular Weight: 171.58
    6. EINECS: 201-921-2
    7. Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Nitrogen Compounds;Organic Building Blocks;Alpha Sort;Analytical Standards;AromaticsVolatiles/ Semivolatiles;C;CAlphabetic;CHChemical Class;Chemical Class;ChloroAnalytical Standards;Halogenated;Nitro Compounds
    8. Mol File: 89-59-8.mol
  • Chemical Properties

    1. Melting Point: 35 °C
    2. Boiling Point: 239-240 °C718 mm Hg(lit.)
    3. Flash Point: >230 °F
    4. Appearance: clear brown liquid after melting
    5. Density: 1.2559
    6. Vapor Pressure: 0.0651mmHg at 25°C
    7. Refractive Index: 1.5570 (estimate)
    8. Storage Temp.: Store below +30°C.
    9. Solubility: N/A
    10. Water Solubility: 109 mg/L (20 ºC)
    11. BRN: 2046651
    12. CAS DataBase Reference: 4-Chloro-2-nitrotoluene(CAS DataBase Reference)
    13. NIST Chemistry Reference: 4-Chloro-2-nitrotoluene(89-59-8)
    14. EPA Substance Registry System: 4-Chloro-2-nitrotoluene(89-59-8)
  • Safety Data

    1. Hazard Codes: Xi,Xn,N
    2. Statements: 36/37/38-20/21/22-52/53
    3. Safety Statements: 26-36-36/37/39-61
    4. RIDADR: UN 3457 6.1/PG 3
    5. WGK Germany: 2
    6. RTECS:
    7. TSCA: Yes
    8. HazardClass: 6.1
    9. PackingGroup: III
    10. Hazardous Substances Data: 89-59-8(Hazardous Substances Data)

89-59-8 Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-2-nitrotoluene is used as a key intermediate in the synthesis of NMDA-glycine antagonists, which are important for the development of drugs targeting neurological disorders.
Used in Pharmaceutical Industry:
4-Chloro-2-nitrotoluene is also used in the preparation of COX-2 inhibitors, which are nonsteroidal anti-inflammatory drugs used for treating pain and inflammation.
Used in Dye Industry:
4-Chloro-2-nitrotoluene can be used in the synthesis of indigo dye, a blue pigment commonly used in the textile industry for dyeing and printing.

Biochem/physiol Actions

4-Chloro-2-nitrotoluene is the starting reagent for synthesis of tricyclic indole-2-carboxylic acids, a potential NMDA-glycine antagonists.

Check Digit Verification of cas no

The CAS Registry Mumber 89-59-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 9 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 89-59:
(4*8)+(3*9)+(2*5)+(1*9)=78
78 % 10 = 8
So 89-59-8 is a valid CAS Registry Number.
InChI:InChI=1/C7H6ClNO2/c1-5-2-3-6(8)4-7(5)9(10)11/h2-4H,1H3

89-59-8 Well-known Company Product Price

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  • Alfa Aesar

  • (B23382)  4-Chloro-2-nitrotoluene, 99%   

  • 89-59-8

  • 100g

  • 246.0CNY

  • Detail
  • Alfa Aesar

  • (B23382)  4-Chloro-2-nitrotoluene, 99%   

  • 89-59-8

  • 500g

  • 944.0CNY

  • Detail
  • Aldrich

  • (101702)  4-Chloro-2-nitrotoluene  98%

  • 89-59-8

  • 101702-100G

  • 333.45CNY

  • Detail
  • Aldrich

  • (101702)  4-Chloro-2-nitrotoluene  98%

  • 89-59-8

  • 101702-500G

  • 1,106.82CNY

  • Detail

89-59-8SDS

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 4-Chloro-2-nitrotoluene

1.2 Other means of identification

Product number -
Other names 4,2-Chloronitrotoluene

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:89-59-8 SDS

89-59-8Synthetic route

(4-Chlor-2-nitro-phenyl)-malonsaeure-diaethylester
10565-16-9

(4-Chlor-2-nitro-phenyl)-malonsaeure-diaethylester

4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

Conditions
ConditionsYield
With dimethyl sulfoxide; sodium chloride at 160 - 170℃; for 24h; Decarboxylation; Krapcho's reaction;55%
para-chlorotoluene
106-43-4

para-chlorotoluene

A

4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

B

1-chloro-4-methyl-2-nitro-benzene
89-60-1

1-chloro-4-methyl-2-nitro-benzene

Conditions
ConditionsYield
With oxygen; Nitrogen dioxide; iron(III)-acetylacetonate In 1,2-dichloro-ethane at 0℃; for 12h;A 54%
B 39%
With nitric acid; urea In acetic anhydride at 0 - 5℃; for 3h;A 9.1%
B 12%
With nitric acid; urea In acetic anhydride at 0 - 5℃; for 3h;A 9.1%
B 12%
para-chlorotoluene
106-43-4

para-chlorotoluene

4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

Conditions
ConditionsYield
With sulfuric acid; nitric acid In water at 50 - 55℃; for 2h;49.2%
With sulfuric acid; nitric acid
With sulfuric acid; nitric acid das mit Aether isolierte Reaktionsprodukt unterwirft man der fraktionierten Destillation, wobei 4-Chlor-2-nitro-toluol bei 240-245grad uebergeht;
Multi-step reaction with 2 steps
1: 2 g / nitric acid, acetic anhydride, trifluoroacetic anhydride
2: 94.3 percent Chromat. / 92.4percent sulphuric acid, hydrazinium sulphate / H2O / 0.03 h / 25 °C
View Scheme
para-chlorotoluene
106-43-4

para-chlorotoluene

A

4-methyl-2-nitrophenol
119-33-5

4-methyl-2-nitrophenol

B

4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

C

1-chloro-4-methyl-2-nitro-benzene
89-60-1

1-chloro-4-methyl-2-nitro-benzene

Conditions
ConditionsYield
With sulfuric acid; nitric acid In water at 25℃; for 3.83333h;A 9.3%
B 39.1%
C 31%
With sulfuric acid; nitric acid In water at 25℃; for 3.83333h; Title compound not separated from byproducts;A 9.3 % Chromat.
B 39.1 % Chromat.
C 31.0 % Chromat.
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

Conditions
ConditionsYield
With oxone; potassium chloride In acetonitrile at 20℃; for 24h;5%
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

A

6-chloro-2-nitrotoluene
83-42-1

6-chloro-2-nitrotoluene

B

4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

Conditions
ConditionsYield
With antimonypentachloride durch Chlorierung;
With chlorine; iron at 30℃;
With antimonypentachloride; chlorine
With chlorine; iron
With iodine; iron at 50 - 60℃; beim Chlorieren;
5-chloro-2-methyl-2-nitrocyclohexa-3,5-dienyl acetate
75508-74-6

5-chloro-2-methyl-2-nitrocyclohexa-3,5-dienyl acetate

A

4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

B

1-chloro-4-methyl-2-nitro-benzene
89-60-1

1-chloro-4-methyl-2-nitro-benzene

Conditions
ConditionsYield
With hydrazin sulfate; sulfuric acid In water at 25℃; for 0.0333333h; Title compound not separated from byproducts;A 94.3 % Chromat.
B 3.5 % Chromat.
3-nitro-4-methylphenylammonium hydrogensulfate

3-nitro-4-methylphenylammonium hydrogensulfate

4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

Conditions
ConditionsYield
(i) aq. HCl, NaNO2, (ii) CuCl, aq. HCl; Multistep reaction;
para-chlorotoluene
106-43-4

para-chlorotoluene

sulfuric acid
7664-93-9

sulfuric acid

A

4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

B

1-chloro-4-methyl-2-nitro-benzene
89-60-1

1-chloro-4-methyl-2-nitro-benzene

Conditions
ConditionsYield
Product distribution; Nitrierung;
para-chlorotoluene
106-43-4

para-chlorotoluene

nitric acid
7697-37-2

nitric acid

A

4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

B

1-chloro-4-methyl-2-nitro-benzene
89-60-1

1-chloro-4-methyl-2-nitro-benzene

Conditions
ConditionsYield
at -15℃; Quantum yield; sowie im Temperaturbereich von 0grad bis 50grad;
at 0℃; Product distribution;
para-chlorotoluene
106-43-4

para-chlorotoluene

acetic anhydride
108-24-7

acetic anhydride

phosphorus pentoxide

phosphorus pentoxide

A

4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

B

1-chloro-4-methyl-2-nitro-benzene
89-60-1

1-chloro-4-methyl-2-nitro-benzene

Conditions
ConditionsYield
Product distribution; Nitrierung;
sodium salt of/the/ 4-chloro-2-nitro-toluene-sulfonic acid-(3)

sodium salt of/the/ 4-chloro-2-nitro-toluene-sulfonic acid-(3)

4-chloro-2-nitro-toluene-sulfonic acid-(3)-amide

4-chloro-2-nitro-toluene-sulfonic acid-(3)-amide

4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

Conditions
ConditionsYield
With sulfuric acid at 220℃; Wasserdampf-Strom;
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

antimonypentachloride
7647-18-9

antimonypentachloride

A

6-chloro-2-nitrotoluene
83-42-1

6-chloro-2-nitrotoluene

B

4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

Conditions
ConditionsYield
bei der Chlorierung;
bei der Chlorierung;
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

chlorine
7782-50-5

chlorine

iron

iron

A

6-chloro-2-nitrotoluene
83-42-1

6-chloro-2-nitrotoluene

B

4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

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

1-methyl-2-nitrobenzene

iodine
7553-56-2

iodine

chlorine
7782-50-5

chlorine

iron

iron

A

6-chloro-2-nitrotoluene
83-42-1

6-chloro-2-nitrotoluene

B

4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

Conditions
ConditionsYield
at 50 - 60℃;
2-nitro-toluene-4-diazonium sulfate

2-nitro-toluene-4-diazonium sulfate

A

4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

B

3,3’-dinitroditoluene
28442-37-7

3,3’-dinitroditoluene

Conditions
ConditionsYield
With hydrogenchloride; copper dichloride
2,5-dichloronitrobenzene
89-61-2

2,5-dichloronitrobenzene

4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dimethylformamide / 20 °C
2: 55 percent / aq. NaCl; DMSO / 24 h / 160 - 170 °C
View Scheme
2,3-dinitro-4-methylaniline
70343-09-8

2,3-dinitro-4-methylaniline

4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Diazotization.folgend Behandlung mit Kupfer(I)-chlorid in Salzsaeure bei 0grad
2: methanol; ammonia / 140 - 150 °C
3: Diazotieren und Kochen mit Alkohol
View Scheme
4-chloro-2,3-dinitro-toluene
170099-17-9

4-chloro-2,3-dinitro-toluene

4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol; ammonia / 140 - 150 °C
2: Diazotieren und Kochen mit Alkohol
View Scheme
toluene
108-88-3

toluene

4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: iodine; iron; chlorine
2: HNO3+H2SO4
View Scheme
4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

5-chloro-2-methyl-benzenamine
95-79-4

5-chloro-2-methyl-benzenamine

Conditions
ConditionsYield
With hydrogen In 2-methyltetrahydrofuran; water at 40℃; under 15001.5 Torr; for 24h; chemoselective reaction;99%
With TPGS-750-M; ammonium chloride; zinc In water at 20℃; for 3h; Green chemistry; chemoselective reaction;97%
With hydrogen In methanol at 50℃; under 1500.15 Torr; for 0.25h; Inert atmosphere;97%
4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

4-chloro-2-nitrobenzyl bromide
52311-59-8

4-chloro-2-nitrobenzyl bromide

Conditions
ConditionsYield
With N-Bromosuccinimide; Perbenzoic acid In tetrachloromethane for 6h; Heating;98%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 24h; Reflux;93%
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 18h; Inert atmosphere; Reflux;69%
4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

4,4,5,5-tetramethyl-2-(4-methyl-3-nitrophenyl)-1,3,2-dioxaborolane
1072945-06-2

4,4,5,5-tetramethyl-2-(4-methyl-3-nitrophenyl)-1,3,2-dioxaborolane

Conditions
ConditionsYield
With sodium acetate; bis(dibenzylideneacetone)-palladium(0); XPhos for 12h; Miyaura Borylation Reaction; Heating;98%
4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

p-chlorobenzyl cyanide
140-53-4

p-chlorobenzyl cyanide

4-chloro-α-(2-chloro-4-hydroxyimino-5-methyl-2,5-cyclohexadien-1-ylidene)phenylacetonitrile
844-24-6

4-chloro-α-(2-chloro-4-hydroxyimino-5-methyl-2,5-cyclohexadien-1-ylidene)phenylacetonitrile

Conditions
ConditionsYield
With methanol; sodium methylate at 50℃; for 3h; Reagent/catalyst; Sealed tube;97.2%
4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

dimethyl-(4'-chloro-2'-nitro-trans-stilbenyl-(4))-amine
106987-32-0

dimethyl-(4'-chloro-2'-nitro-trans-stilbenyl-(4))-amine

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride for 3.5h; Ambient temperature;95%
With piperidine at 170℃;
4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

acetic anhydride
108-24-7

acetic anhydride

N-(5-chloro-2-methylphenyl)acetamide
5900-55-0

N-(5-chloro-2-methylphenyl)acetamide

Conditions
ConditionsYield
Stage #1: 4-chloro-2-nitrotoluene With sodium tetrahydroborate In water at 60 - 70℃; Green chemistry;
Stage #2: acetic anhydride In water at 60 - 70℃; Green chemistry;
94%
4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

trimethyl(phenyl)stannane
934-56-5

trimethyl(phenyl)stannane

1-methyl-2-nitro-4-phenylbenzene
80726-54-1

1-methyl-2-nitro-4-phenylbenzene

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; bis(tri-t-butylphosphine)palladium(0); sodium chloride In water at 60℃; for 24h; Stille Cross Coupling; Inert atmosphere;92%
4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

4-Chloro-2-nitrobenzaldehyde
5551-11-1

4-Chloro-2-nitrobenzaldehyde

Conditions
ConditionsYield
Stage #1: 4-chloro-2-nitrotoluene With N,N-dimethyl-aniline In N,N-dimethyl-formamide at 140℃; for 48h;
Stage #2: With sodium periodate In water; N,N-dimethyl-formamide at 20℃; for 4h;
90%
Stage #1: 4-chloro-2-nitrotoluene With N,N-dimethyl-formamide dimethyl acetal In N,N-dimethyl-formamide at 140℃; for 16h;
Stage #2: With sodium periodate In N,N-dimethyl-formamide at 0 - 20℃; Further stages.;
84%
With N,N-dimethyl-formamide dimethyl acetal In N,N-dimethyl-formamide at 135℃; for 48h; Temperature;54%
4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

5-chloro-trans-2-[β-(dimethylamino)vinyl]-nitrobenzene
32989-56-3

5-chloro-trans-2-[β-(dimethylamino)vinyl]-nitrobenzene

Conditions
ConditionsYield
With copper(l) iodide; N,N-dimethyl-formamide at 180℃; under 6000.6 - 7500.75 Torr; for 0.166667h; microwave irradiation;90%
In N,N-dimethyl-formamide at 115℃; for 20h; Inert atmosphere;73%
at 135℃; for 11h;
4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

6-chloroindole
17422-33-2

6-chloroindole

Conditions
ConditionsYield
Stage #1: 4-chloro-2-nitrotoluene; N,N-dimethyl-formamide dimethyl acetal With pyrrolidine In 1,4-dioxane at 102℃; for 5.5h; Leimgruber-Batcho Indole Synthesis; Reflux; Inert atmosphere;
Stage #2: With hydrazine hydrate In 1,4-dioxane at 45℃; for 1h; Reagent/catalyst; Solvent; Temperature; Leimgruber-Batcho Indole Synthesis;
90%
Stage #1: 4-chloro-2-nitrotoluene; N,N-dimethyl-formamide dimethyl acetal In N,N-dimethyl-formamide at 115℃; for 20h; Leimgruber-Batcho indole synthesis; Inert atmosphere;
Stage #2: With iron(III) chloride hexahydrate; pyrographite; hydrazine hydrate In ethanol at 75℃; for 7h; Leimgruber-Batcho indole synthesis;
4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

4-Chloro-2-nitrobenzaldehyde
5551-11-1

4-Chloro-2-nitrobenzaldehyde

Conditions
ConditionsYield
Stage #1: 4-chloro-2-nitrotoluene; N,N-dimethyl-formamide dimethyl acetal In N,N-dimethyl-formamide at 140℃; for 16h;
Stage #2: With sodium periodate In tetrahydrofuran; water at 0 - 20℃; for 5.16667h;
84%
formaldehyd
50-00-0

formaldehyd

4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

2-(4-chloro-2-nitrophenyl)ethan-1-ol
16764-17-3

2-(4-chloro-2-nitrophenyl)ethan-1-ol

Conditions
ConditionsYield
With potassium hydroxide In water; dimethyl sulfoxide at 20℃; for 3h; Schlenk technique;75%
With N-benzyl-trimethylammonium hydroxide In methanol; dimethyl sulfoxide at 90℃; for 2h;48%
With sodium ethanolate In dimethyl sulfoxide
tributyl(3,6-dihydro-2H-pyran-4-yl)stannane
535924-69-7

tributyl(3,6-dihydro-2H-pyran-4-yl)stannane

4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

4-(4-methyl-3-nitrophenyl)-3,6-dihydro-2H-pyran
1417617-59-4

4-(4-methyl-3-nitrophenyl)-3,6-dihydro-2H-pyran

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; bis(tri-t-butylphosphine)palladium(0); sodium chloride In water at 60℃; for 24h; Temperature; Stille Cross Coupling; Inert atmosphere;73%
pyrrolidine
123-75-1

pyrrolidine

4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

6-chloroindole
17422-33-2

6-chloroindole

Conditions
ConditionsYield
aluminum nickel In tetrahydrofuran; N-methyl-acetamide; methanol72.6%
4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

phenylboronic acid
98-80-6

phenylboronic acid

1-methyl-2-nitro-4-phenylbenzene
80726-54-1

1-methyl-2-nitro-4-phenylbenzene

Conditions
ConditionsYield
With 4,4'-(phenylphosphinediyl)bis(2,6-dimethylmorpholine); caesium carbonate; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane for 14h; Suzuki-Miyaura coupling; Heating;72%
With [1,2-dimethyl-3-propoxymethylimidazolium]2[PdCl4]; potassium hydroxide In water; isopropyl alcohol at 70℃; for 24h; Suzuki-Miyaura Coupling; Schlenk technique;
4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

propionaldehyde
123-38-6

propionaldehyde

3,3'-propane-1,1'-diylbis(4-chloro-7-methyl-1H-indole)
1445721-23-2

3,3'-propane-1,1'-diylbis(4-chloro-7-methyl-1H-indole)

Conditions
ConditionsYield
Stage #1: 4-chloro-2-nitrotoluene; vinyl magnesium bromide In tetrahydrofuran at -40 - 0℃; for 2.5h; Inert atmosphere;
Stage #2: propionaldehyde With hydrogenchloride In tetrahydrofuran; water at 0℃; for 0.5h; Inert atmosphere;
63%
4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

dimethyl 2-(4-methoxybenzylidene)malonate
7443-25-6

dimethyl 2-(4-methoxybenzylidene)malonate

2-[2-(4-Chloro-2-nitro-phenyl)-1-(4-methoxy-phenyl)-ethyl]-malonic acid dimethyl ester

2-[2-(4-Chloro-2-nitro-phenyl)-1-(4-methoxy-phenyl)-ethyl]-malonic acid dimethyl ester

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide Ambient temperature;61%
4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

N-benzyl-trimethylammonium hydroxide
100-85-6

N-benzyl-trimethylammonium hydroxide

2-(4-chloro-2-nitrophenyl)ethan-1-ol
16764-17-3

2-(4-chloro-2-nitrophenyl)ethan-1-ol

Conditions
ConditionsYield
With paraformaldehyde In methanol; dimethyl sulfoxide; ethyl acetate55%
4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

2-(4-chloro-2-nitrophenyl)-1-(4-chlorophenyl)ethanol
1313843-56-9

2-(4-chloro-2-nitrophenyl)-1-(4-chlorophenyl)ethanol

Conditions
ConditionsYield
With sodium methylate52%
4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

3,3’-ethane-1,1-diylbis(4-chloro-7-methyl-1H-indole)
1445721-19-6

3,3’-ethane-1,1-diylbis(4-chloro-7-methyl-1H-indole)

Conditions
ConditionsYield
Stage #1: 4-chloro-2-nitrotoluene; vinyl magnesium bromide In tetrahydrofuran at -40 - 0℃; for 2.5h; Inert atmosphere;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 0℃; for 0.5h; Inert atmosphere;
50%
Dimethyl oxalate
553-90-2

Dimethyl oxalate

4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

methyl 4-chloro-2-nitrophenylpyruvate
199526-95-9

methyl 4-chloro-2-nitrophenylpyruvate

Conditions
ConditionsYield
With sodium methylate In methanol for 2h; Claisen-type condensation; Heating;40%
4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

4-chloro-2,3-dinitro-toluene
170099-17-9

4-chloro-2,3-dinitro-toluene

Conditions
ConditionsYield
With potassium nitrate In sulfuric acid24%
4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

5-chloro-2-methyl-1,3-dinitro-benzene
35572-79-3

5-chloro-2-methyl-1,3-dinitro-benzene

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 0 - 90℃;21.8%
4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

3-(4-chloro-2-nitro-phenyl)-2-hydroxyimino-propionic acid

3-(4-chloro-2-nitro-phenyl)-2-hydroxyimino-propionic acid

Conditions
ConditionsYield
Stage #1: 4-chloro-2-nitrotoluene; oxalic acid diethyl ester With sodium methylate In ethanol at 90℃; for 0.416667h;
Stage #2: With hydroxylamine hydrochloride In water at 50℃;
Stage #3: With hydrogenchloride In water at 20℃; pH=1;
20%
pyridine
110-86-1

pyridine

4-chloro-2-nitrotoluene
89-59-8

4-chloro-2-nitrotoluene

1-(4-chloro-2-nitro-benzyl)-pyridinium; bromide
95196-90-0

1-(4-chloro-2-nitro-benzyl)-pyridinium; bromide

Conditions
ConditionsYield
With bromine

89-59-8Relevant articles and documents

Conformations, equilibrium thermodynamics and rotational barriers of secondary thiobenzanilides

Kozic, Ján,Novák, Zdeněk,?ímal, Václav,Profant, Václav,Kune?, Ji?í,Vin?ová, Jarmila

, p. 2072 - 2083 (2016/04/09)

The article deals with conformational behaviour of 2-methoxy-2′-hydroxythiobenzanilides. The CS-NH group of these compounds preferentially adopts the Z-conformation. Entropy favours the Z-conformer over the E-conformer, whereas enthalpy slightly favours the E-conformer over the Z-conformer. The rotational barrier about the CS-NH bond was determined to be (81.5±0.4) kJ/mol. No significant rotational barrier was found on the Ar-CS and Ar-NH bonds. All experimental outcomes are compared with the results of quantum-chemical calculations.

Highly efficient, para-selective oxychlorination of aromatic compounds using potassium chloride and Oxone

Narender,Srinivasu,Kulkarni,Raghavan

, p. 279 - 286 (2007/10/03)

A highly efficient, regioselective method for oxychlorination of aromatic compounds is possible through electrophilic substitution of chlorine generated in situ from KCl as a chlorine source and Oxone as an oxidant for the first time.

Bis(dealkoxycarbonylation) of nitroarylmalonates: A facile entry to alkylated nitroaromatics

Gurjar,Reddy,Murugaiah,Murugaiah

, p. 1659 - 1661 (2007/10/03)

A simple approach to alkylated nitroaromatics from substituted nitroaryl malonic esters by double decarboxylation is detailed.

Iron(III)-catalysed nitration of non-activated and moderately activated arenes with nitrogen dioxide-molecular oxygen under neutral conditions

Suzuki, Hitomi,Yonezawa, Shuji,Nonoyama, Nobuaki,Mori, Tadashi

, p. 2385 - 2389 (2007/10/03)

In the presence of molecular oxygen and a catalytic amount of tris(pentane-2,4-dionato)iron(III), non-activated and moderately activated arenes, which include alkylbenzenes, halogenobenzenes, phenolic ethers, naphthalene and derivatives, can be nitrated with nitrogen dioxide at ice-bath temperature or below to give the corresponding nitro derivatives in fair to good yields. An electron-transfer mechanism has been proposed, where an activated NO2-FeIII complex plays a key role in the cyclic process for converting arenes into nitroarenes.

A veterinary medicament for preventive treatment and therapy of cattle against parasites

-

, (2008/06/13)

A veterinary medicament to control endo- and ectoparasites including larvae of arthropoda, for oral and parenteral therapeutical and prophylactical application, consisting of Ivermectin and N-[5-chloro-4-α-chlorophenyl-α cyano-methyl-2-methyl-phenyl-]-2-hydroxy-3,5-diiodobenzamide.

Nitration of p-Chlorotoluene and p-Chloroisopropylbenzene

Khan, Iftikhar A.,Manglik, Ajay K.,Sangal, S. K.

, p. 415 - 416 (2007/10/02)

The nitrations of p-chlorotoluene and p-chloroisopropylbenzene with nitric acid in acetic anhydride have been studied.The product composition from the nitration of p-chlorotoluene in acetic anhydride when examined alongwith the previously known product compositions obtained from the nitrations of p-chlorotoluene in varying percentages of sulphuric acid gave information of the degree of attack by the nitronium ion at various positions in p-chlorotoluene.The relative rates of nitrations at various nuclear positions for chlorobenzene could then be calculated.Results from nitration of p-chloroisopropylbenzene were found to be in agreement with these values.

ipso Nitration. XXVIII. Nitration of 4-substituted toluenes: 1,2 adducts

Fisher, Alfred,Fyles, Deborah L.,Henderson, George, N.,Mahasay, Sumit Ray

, p. 1764 - 1770 (2007/10/02)

Nitration of 4-acetamido, 4-chloro, and 4-methoxy-toluene in acetic anhydride gives in each case a cis 1,2 nitronium acetate adduct in adition to the nitro substitution product(s).Nitration of 4-fluorotoluene gives a pair of diastereomeric 1,4 nitronium acetate adducts and the cis 1,2 adduct.

Electrophilic Aromatic Substitution. Part 30. The Kinetics and Products of the Solvolyses in Aqueous Sulphuric Acids of 5-Chloro-2-methyl-2-nitrocyclohexa-3,5-dienyl Acetate: the Occurence of AAC2 and AAl1 Solvolyses, and of an Acid-catalysed Elimination of Nitrous Acid, and the...

Bloomfield, Colin,Moodie, Roy B.,Schofield, Kenneth

, p. 1793 - 1802 (2007/10/02)

Good first order kinetics of solvolysis of the above-named diene in water and in 6.5-43.6percent H2SO4 at 25 deg C, and in water and in 15.2-58.8percent H2SO4 at 5 deg C have been observed.The yields of 4-chlorotoluene, 5-chloro-2-methylphenyl acetate, 5-chloro-2-methylphenol, 4-chloro-2-nitrotoluene, 4-chloro-3-nitrotoluene, and 4-methyl-2-nitrophenol produced in water and in 21.5-92.4percent H2SO4 at 25 deg C in the presence of sulphanilic acid or hydrazinium sulphate, and additionally of 2- and 4-nitroanisole when anisole was also added, have been measured.The solvolysis proceeds by an acid-catalysed elimination of nitrous acid (confirming a tentative conclusion in another case), which competes with AAC2 and AAL1 ester solvolyses.With increasing acidity the solvolyses become dominant, the AAL1 reaction increasingly so.The small yield of 4-chloro-3-nitrotoluene comes from a thermal reaction of the diene unrelated to the elimination and solvolyses.The AAL1 reaction generates the ipso-Wheland intermediate (WiMe) that is also formed in the nitration of 4-chlorotoluene.The intermediate reacts by return to 4-chlorotoluene and nitronium ion (which can be captured by anisole), by 1,2-and 1,4-nucleophilic capture by water (giving 5-chloro-2-methylphenol and 4-methyl-2-nitrophenol, respectively), and by 1,2-rearrangement to 4-chloro-2-nitrotoluene.The first of these reactions never accounts for more than about 12percent of the WiMe and competition between capture and rearrangement moves strongly in favour of the latter with increasing acidity.Re-examination of the nitration of 4-chlorotoluene has revealed products arising from 1,2- and 1,4-capture of WiMe, previously overlooked.An improved assessmentof positional reactivities shows 59percent of primary attack by nitronium ion to occur at C-Me in 63percent H2SO4.

ipso-Nitration: Formation of Nitronium Acetate Adducts in the Nitration of p-Acetamido-, p-Halogeno-, and p-Methoxy-toluenes, and α-p-Tolyloxyisobutyric acid

Fischer, Alfred,Fyles, Deborah L.,Henderson, George N.

, p. 513 - 514 (2007/10/02)

Low-temperature nitration of the title compounds in acetic anhydride gives 1,2-nitronium acetate adducts, except p-fluorotoluene which gives both 1,2 and 1,4 adducts and α-p-tolyloxyisobutyric acid which gives a spiro adduct.

2-Aryl-3,4-diphenylisoxazolin-5-ones

-

, (2008/06/13)

Contacting of appropriately substituted nitrosobenzene with diphenylcyclopropenone under reflux conditions yields novel 2-aryl-3,4-diphenylisoxazolin-5-ones, which are useful as pharmacological agents in view of their serum triglyceride and cholesterol lowering properties.

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