10298-80-3

Basic information

• Product Name: 4-Chloro-3-nitroanisole
• Synonyms: 2-Nitro-4-methoxychlorobenzene;2-CHLORO-5-METHOXYNITROBENZENE;1-CHLORO-4-METHOXY-2-NITROBENZENE;4-CHLORO-3-NITROANISOLE;4-chloro-3-nitro-anisol;4-Chloro-3-Nitroanisole98%(Gc);Benzene, 1-chloro-4-methoxy-2-nitro-;4-methoxy-2-nitrochlorobenzene
• CAS NO: 10298-80-3
• Molecular Formula: C₇H₆ClNO₃
• Molecular Weight: 187.58
• EINECS: 233-674-1
• Product Categories: FINE Chemical & INTERMEDIATES;Miscellaneous;Anisole;Anisoles, Alkyloxy Compounds & Phenylacetates;Chlorine Compounds;Nitro Compounds;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 10298-80-3.mol
• Article Data: 14

Chemical Properties

• Melting Point: 41-43 °C(lit.)
• Boiling Point: 293°C
• Flash Point: >230 °F
• Appearance: Light Cream Dry Crystalline Powder
• Density: 1.366
• Vapor Pressure: 0.00304mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• BRN: 640872
• CAS DataBase Reference: 4-Chloro-3-nitroanisole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-3-nitroanisole(10298-80-3)
• EPA Substance Registry System: 4-Chloro-3-nitroanisole(10298-80-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: BZ8580000
• Hazardous Substances Data: 10298-80-3(Hazardous Substances Data)

Usage

Chemical Properties

beige to ochre powder

Uses

Different sources of media describe the Uses of 10298-80-3 differently. You can refer to the following data:
1. 4-Chloro-3-nitroanisole can be used as disperse azo dyes.
2. 4-chloro-3-nitroanisole is used to synthesize a group of derivatives of 7-methanesulfonylamino-6-phenoxychromone at the pyrone and phenoxy rings.

InChI:InChI=1/C7H6ClNO3/c1-12-5-2-3-6(8)7(4-5)9(10)11/h2-4H,1H3

Synthetic route

4-methoxy-2-nitroaniline (96-96-8) → 2-chloro-5-methoxynitrobenzene (10298-80-3)

Conditions	Yield
Stage #1: 4-methoxy-2-nitroaniline With hydrogenchloride; sodium nitrite In water; acetonitrile at 20℃; for 0.25h; Stage #2: With copper(l) chloride In water; acetonitrile at 60℃; for 3h;	99%
With hydrogenchloride; copper(l) chloride; cobalt(II) chloride; palladium dichloride; sodium nitrite In water at 0 - 5℃; Catalytic behavior; Reagent/catalyst; Concentration;	96%
Stage #1: 4-methoxy-2-nitroaniline With potassium hydrogensulfate; phosphoric acid In water at 8 - 9℃; for 0.833333h; Stage #2: With potassium chloride; tin(II) bromide In water at 19 - 70℃; Temperature;	93%

3-nitro-4-chlorophenol (610-78-6) + carbonic acid dimethyl ester (616-38-6) → 2-chloro-5-methoxynitrobenzene (10298-80-3)

Conditions	Yield
With magnesium oxide In N,N-dimethyl-formamide at 170℃; for 0.5h; Microwave irradiation; Green chemistry;	84%

2-nitro-4-methoxybenzoic acid (33844-21-2) → 2-chloro-5-methoxynitrobenzene (10298-80-3)

Conditions	Yield
With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper (I) acetate; silver sulfate; sodium chloride In dimethyl sulfoxide at 160℃; for 24h; Schlenk technique;	53%
With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper diacetate; silver sulfate; sodium chloride In dimethyl sulfoxide at 160℃; under 760.051 Torr; for 20h; Schlenk technique;	53%
With copper(l) iodide; oxygen; copper(l) chloride In dimethyl sulfoxide at 160℃; under 760.051 Torr; for 30h; Schlenk technique; Sealed tube;	46%

3-nitro-4-chlorobenzenediazonium cation (30930-62-2) + sodium methylate (124-41-4) → 2-Nitroanisole (91-23-6) + 2-Chloronitrobenzene (88-73-3) + 2-chloro-5-methoxynitrobenzene (10298-80-3)

Conditions	Yield
for 16h; Mechanism; Ambient temperature; also reaction with sodium deuteriomethoxide;

potassium methyl sulfate (562-54-9) + potassium-<4-chloro-3-nitro-phenolate> → 2-chloro-5-methoxynitrobenzene (10298-80-3)

Conditions	Yield
With glycerol at 170 - 190℃;

3-nitroanisole (555-03-3) → 2-chloro-5-methoxynitrobenzene (10298-80-3)

Conditions	Yield
With Oxone; ammonium chloride In acetonitrile at 20℃; for 48h;	31 % Chromat.

2-nitro-4-methoxybenzoic acid (33844-21-2) → 4-bromo-3-nitroanizole (5344-78-5) + 2-chloro-5-methoxynitrobenzene (10298-80-3)

Conditions	Yield
With Bromotrichloromethane; trichloroisocyanuric acid; bromine at 10 - 120℃; for 18h; Photolysis;

2-chloro-5-methoxynitrobenzene (10298-80-3) → 2-[(2-amino-4-methoxyphenyl)disulfanyl]-4-methoxyaniline (36210-53-4)

Conditions	Yield
With sodiumsulfide nonahydrate In water at 100℃;	100%

carbon disulfide (75-15-0) + 2-chloro-5-methoxynitrobenzene (10298-80-3) → 5-methoxybenzo[d]thiazole-2-thiol (55690-60-3)

Conditions	Yield
With sodium sulfide at 80℃; for 10h; Temperature; Microwave irradiation;	99%
Stage #1: carbon disulfide; 2-chloro-5-methoxynitrobenzene for 5h; Reflux; Stage #2: With hydrogenchloride In water	93.1%

2-chloro-5-methoxynitrobenzene (10298-80-3) → 2-amino-4-methoxybenzenethiol (14482-32-7)

Conditions	Yield
Stage #1: 2-chloro-5-methoxynitrobenzene With sodium sulfide In water for 20h; Heating / reflux; Stage #2: With hydrogenchloride In water at 20℃; pH=7;	98.9%
(i) Na2S, sulfur, (ii) Sn, aq. HCl; Multistep reaction;
Multi-step reaction with 2 steps 1: ethanol; Na2S2 2: tin; aq.-ethanolic HCl View Scheme
With sodium sulfide; water for 24h; Reflux;

2-chloro-5-methoxynitrobenzene (10298-80-3) → 2-chloro-5-methoxyaniline (2401-24-3)

Conditions	Yield
With iron; ammonium chloride In ethanol; water at 95℃; for 12h;	98%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,10-Phenanthroline; isopropyl alcohol; potassium hydroxide at 100℃; for 15h; Inert atmosphere; Schlenk technique;	96%
With maghemite; methylhydrazine In ethanol at 60℃; for 1h; Sealed tube; Inert atmosphere; chemoselective reaction;	95%

2-chloro-5-methoxynitrobenzene (10298-80-3) → 3-nitro-4-chlorophenol (610-78-6)

Conditions	Yield
With hydrogen bromide In acetic acid for 41h; Heating;	96%
With acetic anhydride; acetic acid In water; ethyl acetate	83.6%
With pyridine hydrochloride at 200℃;
With hydrogen bromide In acetic acid at 120℃; for 24h;
With hydrogen bromide In acetic acid for 41h; Heating;

phenylmethanethiol (100-53-8) + 2-chloro-5-methoxynitrobenzene (10298-80-3) → 2-Nitro-4-methoxy-1-benzylmercapto-benzol (22057-42-7)

Conditions	Yield
With sodium carbonate In ethanol; water for 5h; Heating;	96%
With potassium hydroxide

allyltributylstanane (24850-33-7) + 2-chloro-5-methoxynitrobenzene (10298-80-3) → 1-allyl-4-methoxy-2-nitrobenzene (848492-86-4)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride In 1,2-dichloro-ethane at 120℃; for 0.75h; Microwave irradiation;	95%

2-chloro-5-methoxynitrobenzene (10298-80-3) → 5-methoxybenzo[d]thiazole-2-thiol (55690-60-3)

Conditions	Yield
Stage #1: 2-chloro-5-methoxynitrobenzene With carbon disulfide for 5h; Reflux; Stage #2: With hydrogenchloride In water	93.1%

diethylamine (109-89-7) + 2-chloro-5-methoxynitrobenzene (10298-80-3) → N-ethyl-(4-methoxy-2-nitrophenyl)amine (3360-85-8)

Conditions	Yield
In water at 105℃; for 24h;	92%

2-chloro-5-methoxynitrobenzene (10298-80-3) + (6-methoxy-2-naphthalene)boronic acid (156641-98-4) → 2-methoxy-6-(4-methoxy-2-nitrophenyl)naphthalene

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene for 5h; Suzuki Coupling; Inert atmosphere; Reflux;	91%

ethylamine (75-04-7) + 2-chloro-5-methoxynitrobenzene (10298-80-3) → N-ethyl-(4-methoxy-2-nitrophenyl)amine (3360-85-8)

Conditions	Yield
In water at 100℃; for 12h;	90%
In ethanol

hexan-1-amine (111-26-2) + 2-chloro-5-methoxynitrobenzene (10298-80-3) → N-hexyl-4-methoxy-2-nitroaniline (117703-19-2)

Conditions	Yield
In water at 75℃; for 12h;	90%

2-chloro-5-methoxynitrobenzene (10298-80-3) → 6-methoxy-1H-benzo[d][1,2,3]triazol-1-ol (26198-31-2)

Conditions	Yield
With hydrazine hydrate In n-heptan1ol at 110 - 120℃; for 5h;	90%
With hydrazine hydrate In ethanol at 20℃; for 20h; Reflux;

carbamic acid 2-trimethylsilylethyl ester (3124-37-6) + 2-chloro-5-methoxynitrobenzene (10298-80-3) → (4-methoxy-2-nitrophenyl)carbamic acid 2-trimethylsilanylethyl ester (1257310-77-2)

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 120℃; for 15h; Inert atmosphere;	88%

ethyl 2-cyanoacetate (105-56-6) + 2-chloro-5-methoxynitrobenzene (10298-80-3) → ethyl 2-cyano-2-(4-methoxy-2-nitrophenyl)acetate (65547-98-0)

Conditions	Yield
Stage #1: ethyl 2-cyanoacetate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; Stage #2: 2-chloro-5-methoxynitrobenzene In N,N-dimethyl-formamide; mineral oil at 70℃;	87%
With sodium hydride In N,N-dimethyl-formamide at 100℃;	62%
Stage #1: ethyl 2-cyanoacetate With sodium hydride In dimethyl sulfoxide; mineral oil at 0 - 20℃; for 1.5h; Stage #2: 2-chloro-5-methoxynitrobenzene In dimethyl sulfoxide; mineral oil at 90℃; for 16h;	32%
With sodium hydride In dimethyl sulfoxide at 5 - 90℃; for 8h;
With sodium hydride; cesium fluoride In N,N-dimethyl-formamide at 70℃; for 18h;

2-chloro-5-methoxynitrobenzene (10298-80-3) + phenol (108-95-2) → 4-methoxy-2-nitro-1-phenoxybenzene (84594-95-6)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 110℃; for 4h; Substitution;	84%
With potassium carbonate In N,N-dimethyl-formamide at 100℃; Inert atmosphere;	38%

benzyl chloride (100-44-7) + 2-chloro-5-methoxynitrobenzene (10298-80-3) → 5-methoxy-2-phenyl-1,3-benzothiazole

Conditions	Yield
With N-methylcyclohexylamine; sulfur at 110℃; for 24h; Sealed tube; Inert atmosphere;	83%

2-chloro-5-methoxynitrobenzene (10298-80-3) + benzylamine (100-46-9) → 5-methoxy-2-phenyl-1,3-benzothiazole

Conditions	Yield
With sulfur In neat (no solvent) at 130℃; for 24h; Sealed tube; Inert atmosphere;	80%
With sulfur In pyridine at 100℃; for 16h; Inert atmosphere;	66%

benzoyl chloride (98-88-4) + 2-chloro-5-methoxynitrobenzene (10298-80-3) → N-(2-chloro-5-methoxyphenyl)benzamide

Conditions	Yield
With water; iron at 60℃; for 36h;	78%

2-chloro-5-methoxynitrobenzene (10298-80-3) + para-methylbenzylamine (104-84-7) → 5-methoxy-2-(4′-tolyl)benzo[d]thiazole (101078-50-6)

Conditions	Yield
With sulfur In neat (no solvent) at 130℃; for 24h; Sealed tube; Inert atmosphere;	76%

acetophenone (98-86-2) + 2-chloro-5-methoxynitrobenzene (10298-80-3) → (5-methoxybenzothiazol-2-yl)(phenyl)methanone

Conditions	Yield
With 4-methyl-morpholine; sulfur at 120℃; for 16h; Inert atmosphere;	76%

2-chloro-5-methoxynitrobenzene (10298-80-3) + diethyl malonate (105-53-3) → diethyl 2-(4-methoxy-2-nitrophenyl)malonate (10565-15-8)

Conditions	Yield
Stage #1: diethyl malonate With sodium hydride In N,N-dimethyl-formamide at 20 - 100℃; for 0.666667h; Stage #2: 2-chloro-5-methoxynitrobenzene In N,N-dimethyl-formamide at 20 - 100℃; for 1.5h;	75%
Stage #1: diethyl malonate With sodium hydride In dimethyl sulfoxide at 0 - 83℃; for 3h; Stage #2: 2-chloro-5-methoxynitrobenzene In dimethyl sulfoxide at 50 - 106℃; for 55h;	34%
Stage #1: diethyl malonate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.333333h; Stage #2: 2-chloro-5-methoxynitrobenzene With cesium fluoride In N,N-dimethyl-formamide at 20 - 105℃;	28%
With sodium hydride 1) DMSO, 100 deg C, 40 min, 2a) RT, 30 min, 2b) 100 deg C, 1 h; Yield given. Multistep reaction;

4-(aminomethyl)pyridine (3731-53-1) + 2-chloro-5-methoxynitrobenzene (10298-80-3) → 5-methoxy-2-(pyridin-4-yl)benzo[d]thiazole (51643-53-9)

Conditions	Yield
With sulfur In neat (no solvent) at 130℃; for 24h; Sealed tube; Inert atmosphere;	75%

2-(trimethylsilyl)ethanesulfonamide (125486-96-6) + 2-chloro-5-methoxynitrobenzene (10298-80-3) → 2-(trimethylsilanyl)ethanesulfonic acid (4-methoxy-2-nitrophenyl)amide (1045771-65-0)

Conditions	Yield
With caesium carbonate; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 120℃; for 15h;	74%

sodium diethylmalonate (996-82-7, 34727-00-9, 73177-21-6) + 2-chloro-5-methoxynitrobenzene (10298-80-3) → diethyl 2-(4-methoxy-2-nitrophenyl)malonate (10565-15-8)

Conditions	Yield
In N,N-dimethyl-formamide Heating;	70%

1,2,3,4-tetrahydroisoquinoline (91-21-4) + 2-chloro-5-methoxynitrobenzene (10298-80-3) → 10-methoxy-5,6-dihydrobenzo[4,5]imidazo[2,1-a]isoquinoline

Conditions	Yield
at 130℃; for 24h; Inert atmosphere;	70%

1,3-dihydro-imidazole-2-thione (872-35-5) + 2-chloro-5-methoxynitrobenzene (10298-80-3) → 2-(4-methoxy-2-nitrophenylthio)imidazole (88251-67-6)

Conditions	Yield
With sodium ethanolate In ethanol for 4h; Heating;	68%

4-methoxy-phenol (150-76-5) + 2-chloro-5-methoxynitrobenzene (10298-80-3) → 4-methoxy-1-(4-methoxyphenoxy)-2-nitrobenzene

Conditions	Yield
Stage #1: 4-methoxy-phenol With sodium hydride In N,N-dimethyl-formamide; Petroleum ether at 0℃; for 0.5h; Stage #2: 2-chloro-5-methoxynitrobenzene In N,N-dimethyl-formamide; Petroleum ether at 95℃; for 48h;	67%
With potassium tert-butylate In N,N-dimethyl-formamide at 110℃; for 4h; Substitution;
With sodium hydride In N,N-dimethyl-formamide at 20 - 95℃; for 72h;

Upstream product

• 33844-21-2 2-nitro-4-methoxybenzoic acid 
• 610-78-6 3-nitro-4-chlorophenol 
• 616-38-6 carbonic acid dimethyl ester 
• 555-03-3 3-nitroanisole 
• 562-54-9 potassium methyl sulfate 
• 30930-62-2 3-nitro-4-chlorobenzenediazonium cation 
• 124-41-4 sodium methylate 
• 96-96-8 4-methoxy-2-nitroaniline 

Downstream Products

• 60049-83-4 4-Methoxy-2-nitro-N,N-dimethylbenzeneamine 
• 854651-63-1 N,N-diethyl-N'-(4-methoxy-2-nitro-phenyl)-propanediyldiamine 
• 55690-60-3 5-methoxybenzo[d]thiazole-2(3H)-thione 
• 2401-24-3 2-chloro-5-methoxyaniline 
• 14371-84-7 4,4′-dimethoxy-2,2′-dinitro-diphenyl disulfide 
• 74718-98-2 N-butyl-4-methoxy-2-nitroaniline 
• 65547-98-0 ethyl 2-cyano-2-(4-methoxy-2-nitrophenyl)acetate 
• 118671-03-7 2-(2-amino-4-methoxyphenyl)acetonitrile 
• 22057-42-7 2-Nitro-4-methoxy-1-benzylmercapto-benzol 
• 92905-59-4 1-(2-bromophenoxy)-4-methoxy-2-nitrobenzene 
• 14482-32-7 2-amino-4-methoxybenzenethiol 
• 92023-00-2 2-Amino-4-chlor-4'-methoxy-2'-nitro-diphenylsulfid 
• 2401-25-4 1-chloro-2-iodo-4-methoxybenzene 
• 33358-37-1 (4-methoxy-2-nitrophenyl)(phenyl)sulfane 

Relevant articles and documents

Reactions of Aryl Diazonium Salts and Alkyl Arylazo Ethers. XI. Further Evidence for the Mechanism of Dediazoniation i Basic Alcoholic Solution

A comparison of the relative amounts of dediazoniation, SNAr and aryne reactions of 4-chloro-3-nitrobenzenediazonium ion with methoxide ion in CH3OH and in CD3OH confirms that the dediazoniation reaction involves hydride abstraction from the alkoxide ion by the electrophilic terminal nitrogen atom of the diazonium ion.Furthermore, the relative amounts of anionic and free-radical dediazoniation are the same in CH3OH and in CD3OH.This confirms that the partitioning between the free-radical and anionic pathway for dediazoniation is on the aryl diimide and not on the free diazonium ion.Some previously reported results on the solvent effect (methanol against ethanol) for the reaction have been reinterpreted in the light of the above conclusions.

Induction of Axial Chirality in 8-Arylquinolines through Halogenation Reactions Using Bifunctional Organocatalysts

The enantioselective syntheses of axially chiral heterobiaryls were accomplished through the aromatic electrophilic halogenation of 3-(quinolin-8-yl)phenols with bifunctional organocatalysts that control the molecular conformations during successive halogenations. Axially chiral quinoline derivatives, which have rarely been synthesized in an enantioselective catalytic manner, were afforded in moderate-to-good enantioselectivities through bromination, and an analogous protocol also enabled enantioselective iodination. In addition, this catalytic reaction, which allows enantioselective control through the use of mono-ortho-substituted substrates, allowed the asymmetric synthesis of 8-arylquinoline derivatives bearing two different halogen groups in high enantioselectivities.

PROCESS FOR THE PREPARATION OF ORGANIC HALIDES

The present invention provides a halo-de-carboxylation process for the preparation of organic chlorides, organic bromides and mixtures thereof, from their corresponding carboxylic acids, using a chlorinating agent selected from trichloroisocyanuric acid (TCCA), dichloroisocyanuric acid (DCCA), or combination thereof, and a brominating agent.