121-86-8

Basic information

• Product Name: 2-Chloro-4-nitrotoluene
• Synonyms: 2-Chloro-4-nitrotoluene, 99.0%(GC);2-chloro-4-nitro-toluen;2-chloro-4-nitrotoluen(czech)[qr];3-chloro-4-methylnitrobenzene[qr];Benzene,2-chloro-1-methyl-4-nitro-;benzene,2-chloro-1-methyl-4-nitro-[qr];cnt[qr];nsc60111[qr]
• CAS NO: 121-86-8
• Molecular Formula: C₇H₆ClNO₂
• Molecular Weight: 171.58
• EINECS: 204-501-7
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Halides;Phenyls & Phenyl-Het;Phenyls & Phenyl-Het
• Mol File: 121-86-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: 61 °C
• Boiling Point: 260 °C
• Flash Point: 150 °C
• Appearance: light yellow crystalline powder
• Density: 1.3246 (rough estimate)
• Vapor Pressure: 0.0243mmHg at 25°C
• Refractive Index: 1.5470 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: acetonitrile: soluble
• Water Solubility: 49 mg/L (20 ºC)
• BRN: 1817924
• CAS DataBase Reference: 2-Chloro-4-nitrotoluene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-4-nitrotoluene(121-86-8)
• EPA Substance Registry System: 2-Chloro-4-nitrotoluene(121-86-8)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-36/37/38-20/21/22-52/53
• Safety Statements: 36/37/39-26-61
• RIDADR: UN 3457 6.1/PG 3
• WGK Germany: 2
• RTECS: XS9100000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 121-86-8(Hazardous Substances Data)

Usage

Chemical Properties

LIGHT YELLOW CRYSTALLINE POWDER

Uses

2-Chloro-4-nitrotoluene is a substituted toluene used in the preparation of wide range of compounds such as herbicides, analgesics and

Synthesis Reference(s)

Journal of the American Chemical Society, 104, p. 4680, 1982 DOI: 10.1021/ja00381a032

Safety Profile

A skin and eye irritant. When heated to decomposition it emits toxic fumes of NOx and Cl-.

InChI:InChI=1/C7H6ClNO2/c1-5-2-3-6(9(10)11)4-7(5)8/h2-4H,1H3

Synthetic route

1-methyl-4-nitrobenzene (99-99-0) → 2-chloro-4-nitrotoluene (121-86-8)

Conditions	Yield
With hypochlorous anhydride; sulfuric acid In tetrachloromethane	99%
With iron(III) chloride at 57 - 59℃; durch Chlorierung; unter Ausschluss von Sonnenlicht;
With antimony(III) chloride at 65 - 75℃; durch Chlorierung; unter Ausschluss von Sonnenlicht;

2-methylchlorobenzene (95-49-8) → 2-chloro-4-nitrotoluene (121-86-8)

Conditions	Yield
With nitric acid; acetic anhydride In dichloromethane for 6h; Reagent/catalyst; Solvent; Reflux;	85.4%
With nitric acid; acetic anhydride In dichloromethane; water for 0.333333h; Solvent; Reagent/catalyst; Microwave irradiation;	80.9%

3,4-dichloronitrobenzene (99-54-7) + 1-Methoxy-2-(dimethyl-alanoxy)-ethan (16160-46-6) → 2-chloro-4-nitrotoluene (121-86-8)

Conditions	Yield
Pd(dippp)2 In benzene at 90℃; for 22h; Methylation;	61%

p-toluidine hydrochloride (540-23-8) → 2-chloro-4-nitrotoluene (121-86-8) + 2-chloro-4-methyl-1-nitrobenzene (38939-88-7) + 2-chloro-4-methylnitrosobenzene

Conditions	Yield
With 3,3-dimethyldioxirane In acetone at 20℃;	A 35% B 51% C 14%

3,4-dichloronitrobenzene (99-54-7) + [3-(dimethylamino)propyl]dimethyl aluminium(III) → 2-chloro-4-nitrotoluene (121-86-8)

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In benzene at 90℃; for 22h; Methylation;	21%

4-nitrotoluene-2-sulfonic acid (121-03-9) → 2-chloro-4-nitrotoluene (121-86-8)

Conditions	Yield
With copper dichloride

2-chloro-3-methyl-6-nitro-aniline (55730-13-7) → 2-chloro-4-nitrotoluene (121-86-8)

Conditions	Yield
Diazotieren und Kochen mit Alkohol.Diazotization;

2-methyl-5-nitroaniline (99-55-8) → 2-chloro-4-nitrotoluene (121-86-8)

Conditions	Yield
With hydrogenchloride Diazotization.Kochen der Diazoniumsalz-Loesung mit CuCl;
With hydrogenchloride; Methamphetamin mit NaNO2 diazotieren und in CuCl-Loesung giessen;

1-methyl-4-nitrobenzene (99-99-0) → 2-chloro-4-nitrotoluene (121-86-8) + 1,3-dichloro-2-methyl-5-nitrobenzene (7149-69-1) + 2,3,6-trichloro-4-nitrotoluene (22548-85-2) + 2,3,5,6-tetrachloro-4-nitrotoluene (22490-21-7)

Conditions	Yield
With iodine; chlorine; iron In dichloromethane at 25℃; Title compound not separated from byproducts;

1-methyl-4-nitrobenzene (99-99-0) → 2-chloro-4-nitrotoluene (121-86-8) + 1,3-dichloro-2-methyl-5-nitrobenzene (7149-69-1) + 2,3,6-trichloro-4-nitrotoluene (22548-85-2) + 2,3-dichloro-4-nitro-toluene (569340-31-4) + 2,3,5,6-tetrachloro-4-nitrotoluene (22490-21-7) + 2,5-dichloro-4-nitrotoluene (7149-76-0)

Conditions	Yield
With iodine; chlorine; iron In dichloromethane at 25℃; Product distribution; var. temp., var. time;

2-methylchlorobenzene (95-49-8) → 2-chloro-4-nitrotoluene (121-86-8) + 1-chloro-2-methyl-4-nitrobenzene (13290-74-9)

Conditions	Yield
With molecular sieve; nitric acid; acetic anhydride at 0℃; for 0.5h; Yield given; Yields of byproduct given. Title compound not separated from byproducts;

1-methyl-4-nitrobenzene (99-99-0) + antimonypentachloride (7647-18-9) → 2-chloro-4-nitrotoluene (121-86-8)

Conditions	Yield
at 100℃;

1-methyl-4-nitrobenzene (99-99-0) + chlorine (7782-50-5) + antimony (III)-chloride → 2-chloro-4-nitrotoluene (121-86-8)

Conditions	Yield
at 65 - 75℃; unter Ausschluss von Sonnenlicht;

1-methyl-4-nitrobenzene (99-99-0) + iron(III) chloride (7705-08-0) + chlorination → 2-chloro-4-nitrotoluene (121-86-8)

Conditions	Yield
at 57 - 59℃; unter Ausschluss von Sonnenlicht;

4-nitrotoluene-2-sulfonic acid (121-03-9) + copper (II)-chloride → 2-chloro-4-nitrotoluene (121-86-8)

2-methylchlorobenzene (95-49-8) + nitric acid (7697-37-2) → 6-chloro-2-nitrotoluene (83-42-1) + 2-chloro-4-nitrotoluene (121-86-8) + 1-chloro-2-methyl-4-nitrobenzene (13290-74-9) + 2-chloro-3-nitrotoluene (3970-40-9)

Conditions	Yield
at 0℃; Product distribution;

4-nitro-toluene-2-diazonium sulfate → 2-chloro-4-nitrotoluene (121-86-8) + 2,2'-dimethyl-5,5'-dinitrobiphenyl (32304-72-6)

Conditions	Yield
With hydrogenchloride; copper dichloride

o-toluidine (95-53-4) → 2-chloro-4-nitrotoluene (121-86-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid; nitric acid 2: ice; concentrated hydrochloric acid / mit NaNO2 diazotieren und in CuCl-Loesung giessen View Scheme

dichloride monoxide + 2-chloro-4-nitrotoluene (121-86-8) → 1-nitro-3-chloro-4-trichloromethylbenzene

Conditions	Yield
In tetrachloromethane	99.2%

2-chloro-4-nitrotoluene (121-86-8) → 3-chloro-p-toluidine (95-74-9)

Conditions	Yield
With LaCu0.67Si1.33; hydrogen In isopropyl alcohol at 120℃; under 22502.3 Torr; for 84h; Autoclave;	99%
Stage #1: 2-chloro-4-nitrotoluene With hydrogenchloride; 1,1,1,3',3',3'-hexafluoro-propanol; iron In water at 20℃; for 0.5h; Stage #2: With sodium hydrogencarbonate In water chemoselective reaction;	83%
With hydrogenchloride; tin

2-chloro-4-nitrotoluene (121-86-8) + 4-dimethylamino-benzaldehyde (100-10-7) → dimethyl-(2'-chloro-4'-nitro-trans-stilbenyl-(4))-amine (106987-33-1)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride for 3h; Ambient temperature;	98%
With piperidine at 170℃;

styrene (292638-84-7) + 2-chloro-4-nitrotoluene (121-86-8) → (E)-1-methyl-4-nitro-2-styrylbenzene

Conditions	Yield
Stage #1: 2-chloro-4-nitrotoluene With palladium diacetate; heptakis(6-amino-6-deoxy)-β-cyclodextrin; potassium iodide In water; N,N-dimethyl-formamide for 0.5h; Stage #2: styrene With potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 16h;	92%

2-chloro-4-nitrotoluene (121-86-8) → p-toluidine (106-49-0)

Conditions	Yield
With hydrogen; triethylamine; palladium on activated charcoal In methanol at 20℃; for 2h;	90%

2-chloro-4-nitrotoluene (121-86-8) + carbon monoxide (201230-82-2) → 1,3-bis(3-chloro-4-methylphenyl)urea

Conditions	Yield
With sodium acetate; selenium In water; N,N-dimethyl-formamide at 95℃; for 12h; atmospheric pressure;	89%

2-chloro-4-nitrotoluene (121-86-8) + [1,4]naphthoquinone (130-15-4) → 2-(3-chloro-4-methylphenylamino)naphthalene-1,4-dione

Conditions	Yield
With zinc(II) acetate dihydrate; acetic acid; zinc at 20℃; for 5h;	88%
With zinc(II) acetate dihydrate; acetic acid; zinc In water at 20℃; for 5h;	38%

2-aminopyrimidine (109-12-6) + 2-chloro-4-nitrotoluene (121-86-8) + carbon monoxide (201230-82-2) → N-(3-chloro-4-methylphenyl)-N'-(2-pyrimidyl)urea (64699-76-9)

Conditions	Yield
With triethylamine; selenium(IV) oxide In toluene at 140 - 150℃; under 22501.8 Torr; for 4h;	87.5%

2-chloro-4-nitrotoluene (121-86-8) → 2-chloro-4,5-dinitro-toluene (56136-79-9)

Conditions	Yield
With sulfuric acid; uronium nitrate at 0 - 20℃; Nitration;	86%

4,6-dimethoxy-2-aminopyrimidine (36315-01-2) + 2-chloro-4-nitrotoluene (121-86-8) + carbon monoxide (201230-82-2) → N-(3-chloro-4-methylphenyl)-N'-(4,6-dimethoxy-2-pyrimidyl)urea

Conditions	Yield
With triethylamine; selenium(IV) oxide In toluene at 140 - 150℃; under 22501.8 Torr; for 4h;	86%

2-chloro-4-nitrotoluene (121-86-8) + potassium thioacetate (10387-40-3) → N-(3-chloro-4-methylphenyl)acetamide (7149-79-3)

Conditions	Yield
In N,N-dimethyl-formamide at 130℃; for 2h;	85%
In N,N-dimethyl-formamide at 130℃; for 2h; Product distribution / selectivity;	85%
Triton-X 405 at 130℃; for 2h; Product distribution / selectivity;	75%

1-thiopropane (107-03-9) + 2-chloro-4-nitrotoluene (121-86-8) + carbon monoxide (201230-82-2) → (3-chloro-4-methyl-phenyl)-thiocarbamic acid S-propyl ester

Conditions	Yield
With selenium; triethylamine at 60℃; for 10h;	83%

2-Amino-4,6-dimethylpyrimidine (767-15-7) + 2-chloro-4-nitrotoluene (121-86-8) + carbon monoxide (201230-82-2) → 1-(3-chloro-4-methyl-phenyl)-3-(4,6-dimethyl-pyrimidin-2-yl)-urea

Conditions	Yield
With selenium; triethylamine In toluene at 150℃; for 4h;	82.5%

4-amino-2,6-dimethylpyrimidine (461-98-3) + 2-chloro-4-nitrotoluene (121-86-8) + carbon monoxide (201230-82-2) → 1-(3-chloro-4-methyl-phenyl)-3-(2,6-dimethyl-pyrimidin-4-yl)-urea

Conditions	Yield
With selenium; triethylamine In toluene at 150℃; for 4h;	82.5%

5-chloro-2-pyridylamine (1072-98-6) + 2-chloro-4-nitrotoluene (121-86-8) + carbon monoxide (201230-82-2) → 1-(3-chloro-4-methyl-phenyl)-3-(5-chloro-pyridin-2-yl)-urea

Conditions	Yield
With selenium; triethylamine In toluene at 130℃; for 4h;	81%

N,N,N-­trimethyl-­1-­phenylmethanaminium trifluoromethanesulfonate (260783-80-0) + 2-chloro-4-nitrotoluene (121-86-8) + molybdenum hexacarbonyl (13939-06-5, 199620-15-0) → N-(3-chloro-4-methylphenyl)-2-phenylacetamide

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium(II) acetylacetonate; water; potassium carbonate In acetonitrile at 130℃; for 13h; Inert atmosphere; Sealed tube;	79%

2-chloro-4-nitrotoluene (121-86-8) → 1,2-bis(2-chloro-4-nitrophenyl)ethanol

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 30℃; for 48h;	73%

2-chloro-4-nitrotoluene (121-86-8) → 1-(bromomethyl)-2-chloro-4-nitrobenzene (42533-63-1)

Conditions	Yield
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane Reflux; Inert atmosphere;	72%
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 80℃; Solvent; Inert atmosphere; Reflux;	72%
With bromine at 130 - 135℃;

styrene (292638-84-7) + 2-chloro-4-nitrotoluene (121-86-8) + molybdenum hexacarbonyl (13939-06-5, 199620-15-0) → N-(3-chloro-4-methylphenyl)cinnamamide

Conditions	Yield
With bis(acetylacetonato)palladium(II); 1,3-bis-(diphenylphosphino)propane; benzenesulfonic acid In 1,4-dioxane at 130℃; for 14h; Inert atmosphere; Sealed tube; regioselective reaction;	72%

hex-3-yne (928-49-4) + 2-chloro-4-nitrotoluene (121-86-8) + molybdenum hexacarbonyl (13939-06-5, 199620-15-0) → C14H18ClNO

Conditions	Yield
With palladium(II) trifluoroacetate; toluene-4-sulfonic acid; bis[2-(diphenylphosphino)phenyl] ether In water; toluene at 140℃; for 14h;	72%

hex-3-yne (928-49-4) + 2-chloro-4-nitrotoluene (121-86-8) + molybdenum hexacarbonyl (13939-06-5, 199620-15-0) → C15H16ClNO2

Conditions	Yield
With bis(acetylacetonato)palladium(II); 4-chloro-benzenesulfonic acid; 1,3-bis-(diphenylphosphino)propane In N,N-dimethyl-formamide at 100℃; for 14h;	62%

2-chloro-4-nitrotoluene (121-86-8) + 2-[1-cyano-2,2-bis(methylsulfanyl)vinyl]benzonitrile (1616776-05-6) → 4-amino-3-(2-chloro-4-nitrophenyl)-2-(methylthio)-1-naphthonitrile

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide at 90℃; for 2h;	41%

2-chloro-4-nitrotoluene (121-86-8) + 2-(3,3-bis(methylthio)-1-phenylallylidene)malononitrile (64608-21-5) → 3'-amino-2″-chloro-5'-(methylthio)-4″-nitro-[1,1':4',1″-terphenyl]-2'-carbonitrile

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide at 60℃; for 5h;	41%

2-chloro-4-nitrotoluene (121-86-8) + acetic anhydride (108-24-7) → 2-chloro-4-nitrobenzal diacetate (77455-54-0)

Conditions	Yield
With chromium(VI) oxide; sulfuric acid In acetic acid at 5 - 8℃;	36%
With chromium(VI) oxide; sulfuric acid; acetic acid at 0 - 10℃;	28%
With chromium(VI) oxide; sulfuric acid In acetic acid at 0℃; for 1.25h;	24%

2-chloro-4-nitrotoluene (121-86-8) + 2,6-dichlorobenzaldehyde (83-38-5) → (Z)-3-chloro-N-(2,6-dichlorobenzylidene)-4-methylaniline oxide

Conditions	Yield
With ammonium chloride; zinc In ethanol; water at 0 - 20℃; for 16h;	35%

Upstream product

• 99-99-0 1-methyl-4-nitrobenzene 
• 7647-18-9 antimonypentachloride 
• 7782-50-5 chlorine 
• 7705-08-0 iron(III) chloride 
• 121-03-9 4-nitrotoluene-2-sulfonic acid 
• 95-49-8 2-methylchlorobenzene 
• 7697-37-2 nitric acid 
• 95-53-4 o-toluidine 
• 540-23-8 p-toluidine hydrochloride 
• 99-54-7 3,4-dichloronitrobenzene 
• 16160-46-6 1-Methoxy-2-(dimethyl-alanoxy)-ethan 
• 99-55-8 2-methyl-5-nitroaniline 
• 55730-13-7 2-chloro-3-methyl-6-nitro-aniline 

Downstream Products

• 65655-68-7 1,2-bis(3-chloro-4-methylphenyl)diazene oxide 
• 7149-69-1 1,3-dichloro-2-methyl-5-nitrobenzene 
• 96-90-2 1-chloro-2-methyl-3,5-dinitrobenzene 
• 56136-79-9 2-chloro-4,5-dinitro-toluene 
• 107016-63-7 2,2'-dichloro-4,4'-dinitro-trans-stilbene 
• 64699-76-9 N-(3-chloro-4-methylphenyl)-N'-(2-pyrimidyl)urea 
• 107947-94-4 1,3-bis(3-chloro-4-methylphenyl)urea 
• 7149-79-3 N-(3-chloro-4-methylphenyl)acetamide 
• 106-49-0 p-toluidine 
• 107016-63-7 2,2'-dichloro-4,4'-dinitro-cis-stilbene; low-melting 2,2'-dichloro-4,4'-dinitro-stilbene 
• 42533-63-1 1-(bromomethyl)-2-chloro-4-nitrobenzene 
• 42460-61-7 4-amino-2-chloro-benzaldehyde 
• 95-74-9 3-chloro-p-toluidine 
• 99-60-5 2-chloro-4-nitrobenzoic acid 

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Molecular structure, vibrational spectra, HOMO, LUMO and NMR studies of 2-Chloro-4-nitrotoluene (cas 121-86-8) and 4-chloro-2-nitrotoluene09/04/2019

The solid phase FTIR and FT-Raman spectra of 2-chloro-4-nitrotoluene (2Cl4NT) and 4-chloro-2-nitrotoluene (4Cl2NT) were recorded in the regions 4000–400 cm−1 and 4000–50 cm−1 respectively. The fundamental vibrational frequencies and intensities of the vibrational bands were evaluated using den...detailed

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