4-Chloro-2-nitrotoluene supplier

Name
4-Chloro-2-nitrotoluene
EINECS 201-921-2
CAS No. 89-59-8
Article Data31
CAS DataBase
Density 1.324 g/cm³
Solubility 109 mg/L (20 °C) in water
Melting Point 35 °C
Formula C₇H₆ClNO₂
Boiling Point 238.5 °C at 760 mmHg
Molecular Weight 171.583
Flash Point 98.1 °C
Transport Information UN 3457 6.1/PG 3
Appearance clear brown liquid after melting
Safety 26-36/37/39-61
Risk Codes 36/37/38-20/21/22-52/53
Molecular Structure
Hazard Symbols Xi,Xn,N
Synonyms 4-Chloro-1-methyl-2-nitro-benzene;
PSA 45.82000
LogP 3.07980

Synthetic route

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

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

Conditions

Conditions	Yield
With dimethyl sulfoxide; sodium chloride at 160 - 170℃; for 24h; Decarboxylation; Krapcho's reaction;	55%

: 106-43-4
para-chlorotoluene

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

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

Conditions

Conditions	Yield
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%

: 106-43-4
para-chlorotoluene

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

Conditions

Conditions	Yield
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

: 106-43-4
para-chlorotoluene

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

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

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

Conditions

Conditions	Yield
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.

...Expand

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

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

Conditions

Conditions	Yield
With oxone; potassium chloride In acetonitrile at 20℃; for 24h;	5%

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

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

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

Conditions

Conditions	Yield
With antimonypentachloride durch Chlorierung;
With chlorine; iron at 30℃;
With antimonypentachloride; chlorine
With chlorine; iron
With iodine; iron at 50 - 60℃; beim Chlorieren;

: 75508-74-6
5-chloro-2-methyl-2-nitrocyclohexa-3,5-dienyl acetate

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

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

Conditions

Conditions	Yield
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

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

Conditions

Conditions	Yield
(i) aq. HCl, NaNO2, (ii) CuCl, aq. HCl; Multistep reaction;

: 106-43-4
para-chlorotoluene

: 7664-93-9
sulfuric acid

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

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

Conditions

Conditions	Yield
Product distribution; Nitrierung;

...Expand

: 106-43-4
para-chlorotoluene

: 7697-37-2
nitric acid

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

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

Conditions

Conditions	Yield
at -15℃; Quantum yield; sowie im Temperaturbereich von 0grad bis 50grad;
at 0℃; Product distribution;

...Expand

: 106-43-4
para-chlorotoluene

: 108-24-7
acetic anhydride

phosphorus pentoxide: phosphorus pentoxide

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

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

Conditions

Conditions	Yield
Product distribution; Nitrierung;

...Expand

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

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

Conditions

Conditions	Yield
With sulfuric acid at 220℃; Wasserdampf-Strom;

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

: 7647-18-9
antimonypentachloride

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

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

Conditions

Conditions	Yield
bei der Chlorierung;
bei der Chlorierung;

...Expand

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

: 7782-50-5
chlorine

iron: iron

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

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

...Expand

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

: 7553-56-2
iodine

: 7782-50-5
chlorine

iron: iron

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

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

Conditions

Conditions	Yield
at 50 - 60℃;

...Expand

2-nitro-toluene-4-diazonium sulfate: 2-nitro-toluene-4-diazonium sulfate

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

B: 28442-37-7
3,3’-dinitroditoluene

Conditions

Conditions	Yield
With hydrogenchloride; copper dichloride

: 89-61-2
2,5-dichloronitrobenzene

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylformamide / 20 °C 2: 55 percent / aq. NaCl; DMSO / 24 h / 160 - 170 °C View Scheme

: 70343-09-8
2,3-dinitro-4-methylaniline

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

Conditions

Conditions	Yield
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

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

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

Conditions

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

: 108-88-3
toluene

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: iodine; iron; chlorine 2: HNO3+H2SO4 View Scheme

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

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

Conditions

Conditions	Yield
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%

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

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

Conditions

Conditions	Yield
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%

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

: 73183-34-3
bis(pinacol)diborane

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

Conditions

Conditions	Yield
With sodium acetate; bis(dibenzylideneacetone)-palladium(0); XPhos for 12h; Miyaura Borylation Reaction; Heating;	98%

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

: 140-53-4
p-chlorobenzyl cyanide

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

Conditions

Conditions	Yield
With methanol; sodium methylate at 50℃; for 3h; Reagent/catalyst; Sealed tube;	97.2%

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

: 100-10-7
4-dimethylamino-benzaldehyde

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

Conditions

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride for 3.5h; Ambient temperature;	95%
With piperidine at 170℃;

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

: 108-24-7
acetic anhydride

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

Conditions

Conditions	Yield
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%

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

: 934-56-5
trimethyl(phenyl)stannane

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

Conditions

Conditions	Yield
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%

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

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

Conditions

Conditions	Yield
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%

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

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

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

Conditions

Conditions	Yield
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;

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

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

: 17422-33-2
6-chloroindole

Conditions

Conditions	Yield
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;

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

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

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

Conditions

Conditions	Yield
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%

: 50-00-0
formaldehyd

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

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

Conditions

Conditions	Yield
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

: 535924-69-7
tributyl(3,6-dihydro-2H-pyran-4-yl)stannane

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

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

Conditions

Conditions	Yield
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%

: 123-75-1
pyrrolidine

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

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

: 17422-33-2
6-chloroindole

Conditions

Conditions	Yield
aluminum nickel In tetrahydrofuran; N-methyl-acetamide; methanol	72.6%

...Expand

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

: 98-80-6
phenylboronic acid

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

Conditions

Conditions	Yield
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;

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

: 1826-67-1
vinyl magnesium bromide

: 123-38-6
propionaldehyde

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

Conditions

Conditions	Yield
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%

...Expand

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

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

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

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide Ambient temperature;	61%

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

: 100-85-6
N-benzyl-trimethylammonium hydroxide

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

Conditions

Conditions	Yield
With paraformaldehyde In methanol; dimethyl sulfoxide; ethyl acetate	55%

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

: 104-88-1
4-chlorobenzaldehyde

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

Conditions

Conditions	Yield
With sodium methylate	52%

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

: 1826-67-1
vinyl magnesium bromide

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

Conditions

Conditions	Yield
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%

: 553-90-2
Dimethyl oxalate

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

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

Conditions

Conditions	Yield
With sodium methylate In methanol for 2h; Claisen-type condensation; Heating;	40%

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

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

Conditions

Conditions	Yield
With potassium nitrate In sulfuric acid	24%

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

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

Conditions

Conditions	Yield
With sulfuric acid; nitric acid at 0 - 90℃;	21.8%

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

: 95-92-1
oxalic acid diethyl ester

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

Conditions

Conditions	Yield
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%

: 110-86-1
pyridine

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

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

Conditions

Conditions	Yield
With bromine

4-Chloro-2-nitrotoluene Specification

The 4-Chloro-2-nitrotoluene, with the CAS registry number 89-59-8, is also known as Benzene, 4-Chloro-1-methyl-2-nitro-. It belongs to the product categories of 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. Its EINECS registry number is 201-921-2. This chemical's molecular formula is C₇H₆ClNO₂ and molecular weight is 171.58. What's more, both its IUPAC name and systematic name are the same which is called 4-Chloro-1-methyl-2-nitrobenzene. It should be stored in a cool, dry and well-ventilated place.

Physical properties about 4-Chloro-2-nitrotoluene are: (1)ACD/LogP: 2.918; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.92; (4)ACD/LogD (pH 7.4): 2.92; (5)ACD/BCF (pH 5.5): 97.27; (6)ACD/BCF (pH 7.4): 97.27; (7)ACD/KOC (pH 5.5): 921.73; (8)ACD/KOC (pH 7.4): 921.73; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 45.82 Å²; (13)Index of Refraction: 1.57; (14)Molar Refractivity: 42.518 cm³; (15)Molar Volume: 129.501 cm³; (16)Surface Tension: 45.46 dyne/cm; (17)Density: 1.325 g/cm³; (18)Flash Point: 98.053 °C; (19)Enthalpy of Vaporization: 45.61 kJ/mol; (20)Boiling Point: 238.518 °C at 760 mmHg; (21)Vapour Pressure: 0.065 mmHg at 25 °C.

Preparation of 4-Chloro-2-nitrotoluene: this chemical can be prepared by (4-Chlor-2-nitro-phenyl)-malonsaeure-diaethylester. This reaction needs reagents NaCl and DMSO at temperature of 160-170 °C. The reaction time is 24 hours. The yield is 55 %.

4-Chloro-2-nitrotoluene can be prepared by (4-Chlor-2-nitro-phenyl)-malonsaeure-diaethylester.

Uses of 4-Chloro-2-nitrotoluene: (1) it is used as dye intermediateand and organic Intermediate; (2) it is used to produce other chemicals. For example, it can react with 4-Dimethylamino-benzaldehyde to get {4-[2-(4-Chloro-2-nitro-phenyl)-vinyl]-phenyl}-dimethyl-amine. The reaction occurs with reagents benzyltriethylammonium chloride, 50 percent aq. NaOH. The yield is 95 %.

4-Chloro-2-nitrotoluene can react with 4-Dimethylamino-benzaldehyde to get {4-[2-(4-Chloro-2-nitro-phenyl)-vinyl]-phenyl}-dimethyl-amine.

When you are dealing with this chemical, you should be very careful. This chemical may cause damage to health and may cause inflammation to the skin or other mucous membranes. It may may present an immediate or delayed danger to one or more components of the environment. This chemical is inflammation to the skin, eyes and respiratory system. In addition, it may cause damage to health by inhalation, in contacting with skin and if swallowed. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. You must avoid releasing to the environment. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: Clc1cc([N+]([O-])=O)c(cc1)C
(2) InChI: InChI=1S/C7H6ClNO2/c1-5-2-3-6(8)4-7(5)9(10)11/h2-4H,1H3
(3) InChIKey: SQFLFRQWPBEDHM-UHFFFAOYSA-N

Product Name

4-Chloro-2-nitrotoluene

Synthetic route

4-Chloro-2-nitrotoluene Specification

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