577-19-5

Basic information

• Product Name: 1-Bromo-2-nitrobenzene
• Synonyms: o-nitrophenylbromide;2-Nitrobromobenzene;2-BROMONITROBENZENE;1-BROMO-2-NITROBENZENE;AURORA KA-1883;O-BROMONITROBENZENE;O-NITROBROMOBENZENE;1-BROMO-2-NITROBENZENE, 99+%
• CAS NO: 577-19-5
• Molecular Formula: C₆H₄BrNO₂
• Molecular Weight: 202.01
• EINECS: 209-409-0
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Benzene derivates;Miscellaneous;Bromine Compounds;Nitro Compounds;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 577-19-5.mol
• Article Data: 92

Chemical Properties

• Melting Point: 40-42 °C(lit.)
• Boiling Point: 261 °C(lit.)
• Flash Point: >230 °F
• Appearance: white to light yellow crystal powder
• Density: 1.7 g/cm3 (20℃)
• Vapor Pressure: 0.0192mmHg at 25°C
• Refractive Index: 1.6060 (estimate)
• Storage Temp.: 2-8°C
• Water Solubility: insoluble
• Stability: Stable. Combustible. Incompatible with strong bases, strong oxidizing agents.
• BRN: 2044109
• CAS DataBase Reference: 1-Bromo-2-nitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Bromo-2-nitrobenzene(577-19-5)
• EPA Substance Registry System: 1-Bromo-2-nitrobenzene(577-19-5)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 36/37-36/37/39-26-22
• RIDADR: UN 3459 6.1/PG 3
• WGK Germany: 3
• RTECS: CY9040450
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 577-19-5(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

Different sources of media describe the Uses of 577-19-5 differently. You can refer to the following data:
1. 1-Bromo-2-nitrobenzene is used in organic synthesis. It also can react with 2-methylamino-benzoic acid to get N-methyl-N-(2-nitro-phenyl)-anthranilic acid. And it is also used in the preparation of 4-methoxy-2?-nitrodiphenyl ether, 1-methoxy-3,5-bis-(2-nitro-phenoxy)benzene.
2. 1-Bromo-2-nitrobenzene may be used in the preparation of: 4-methoxy-2′-nitrodiphenyl ether1-methoxy-3,5-bis-(2-nitro-phenoxy)benzene5-hydroxy-3-methoxy-2′-nitrodiphenyl ether

General Description

1-Bromo-2-nitrobenzene undergoes palladium[0]-mediated Ullmann cross-coupling reaction with a range of β-halo-enals, -enones or -esters to afford the corresponding β-aryl derivatives. Palladium[0]-mediated Ullmann cross-coupling reaction of 1-bromo-2-nitrobenzene with β-bromo-α,β-unsaturated aldehydes is reported.

Purification Methods

Crystallise it twice from pet ether, using charcoal before the first crystallisation. [Beilstein 5 III 618, 5 IV 728.]

InChI:InChI=1/C6H4BrNO2/c7-5-3-1-2-4-6(5)8(9)10/h1-4H

Synthetic route

ortho-nitrobenzoic acid (552-16-9) → 2-nitrophenyl bromide (577-19-5)

Conditions	Yield
With bromine; dibromoisocyanuric acid In dichloromethane at 20℃; for 24h; Reagent/catalyst; Concentration; UV-irradiation;	100%
With Bromotrichloromethane; trichloroisocyanuric acid; bromine In tetrachloromethane at 10 - 120℃; for 18h; Temperature; Reagent/catalyst; Concentration; Photolysis;	97%
With [bis(acetoxy)iodo]benzene; bromine In various solvent(s) for 22h; bromodecarboxylation; Heating; irradiation;	51%

4-bromo-3-nitrobenzoic acid (6319-40-0) → 2-nitrophenyl bromide (577-19-5)

Conditions	Yield
With sulfolane; sodium hydrogencarbonate at 195℃; for 2h;	92%

2-nitrobenzenediazonium o-benzenedisulfonamide → 2-nitrophenyl bromide (577-19-5)

Conditions	Yield
With tetrabutylammomium bromide; copper In acetonitrile at 20℃; for 0.75h; Substitution;	89%
With tetrabutylammomium bromide In acetonitrile at 60℃; for 0.75h; Substitution;	83%

(2-bromophenyl)boronic acid (244205-40-1) → 2-nitrophenyl bromide (577-19-5)

Conditions	Yield
With Iron(III) nitrate nonahydrate In toluene at 80℃; for 18h; Inert atmosphere;	87%
With copper(I) oxide; ammonium hydroxide; oxygen; sodium nitrite In water at 25℃; for 36h;	44%

C14H10Br2F3IO4S → 2-nitrophenyl bromide (577-19-5)

Conditions	Yield
With sodium nitrite In 1,2-dichloro-ethane at 20 - 80℃; Schlenk technique;	85%

2-nitro-aniline (88-74-4) → 2-nitrophenyl bromide (577-19-5)

Conditions	Yield
With tert.-butylnitrite; tetrabutylammomium bromide; copper(I) bromide; 10-camphorsulfonic acid In acetonitrile at 20℃; for 24h; Reagent/catalyst; Time; Solvent;	83%
With potassium nitrite; hydrogen bromide; dimethyl sulfoxide In water at 35℃; for 0.25h;	78%
With tert.-butylnitrite; tetrabutylammomium bromide; toluene-4-sulfonic acid; copper(ll) bromide In acetonitrile at 20℃; for 1h;	76%

o-nitroiodobenzene (609-73-4) → 2-nitrophenyl bromide (577-19-5)

Conditions	Yield
With aluminum oxide; copper(I) bromide In various solvent(s) at 150℃; for 8h;	80%

2-nitrophenylboronic acid (5570-19-4) → 2-nitrophenyl bromide (577-19-5)

Conditions	Yield
With sodium nitrite In acetonitrile at 80℃; for 20h; Sealed tube;	80%

nitrobenzene (98-95-3) → 2-nitrophenyl bromide (577-19-5)

Conditions	Yield
Stage #1: nitrobenzene With acetic acid at 0℃; Stage #2: With bromine at 20℃; for 12h;	78.9%
With bromine; acetic acid at 0 - 20℃; for 12h;	78.9%
With hydrogen bromide; dimethyl sulfoxide for 21h; Ambient temperature;	67%

bromobenzene (108-86-1) → 2-nitrophenyl bromide (577-19-5) + para-nitrophenyl bromide (586-78-7)

Conditions	Yield
With nitric acid at 50℃; for 3h;	A 20.9% B 78.2%
With Iron(III) nitrate nonahydrate; phosphorus pentoxide In neat (no solvent) at 20℃; for 6h; Milling; Green chemistry; Overall yield = 93 percent;	A 25% B 68%
With thionyl chloride; bismuth subnitrate In dichloromethane at 20℃; for 9h;	A 18% B 60%

2-bromoaniline (615-36-1) → 2-nitrophenyl bromide (577-19-5)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane for 10h; Reflux;	74%
Stage #1: 2-bromoaniline With sulfuric acid In 1,4-dioxane at -15℃; Stage #2: With sodium nitrite In 1,4-dioxane at -15℃;

2-nitrobenzenediazonium tetrafluoroborate (365-33-3) → 2-nitrophenyl bromide (577-19-5)

Conditions	Yield
With N-Bromosuccinimide; tetrabutylammonium perchlorate In methanol; N,N-dimethyl-formamide at 20℃; for 3h; Sandmeyer Reaction; Electrochemical reaction;	61%

1,2-Dinitrobenzene (528-29-0) → 2-nitrophenyl bromide (577-19-5)

Conditions	Yield
Stage #1: 1,2-Dinitrobenzene With perchloric acid; sulfuric acid; sodium nitrite In water; ethyl acetate Electrochemical reaction; Stage #2: With hydrogen bromide; copper In water Electrochemical reaction;	60%

2-nitrophenyl trifluoromethanesulfonate (132993-22-7) → 2-nitrophenyl bromide (577-19-5)

Conditions	Yield
With tetrabutylammomium bromide In toluene for 48h; Heating;	48%

o-nitrophenylhydrazine hydrochloride (6293-87-4) → 2-nitrophenyl bromide (577-19-5)

Conditions	Yield
With boron tribromide; dimethyl sulfoxide at 80℃; for 1h;	45%

3-Bromo-4-nitrobenzoic acid (101420-81-9) → 2-nitrophenyl bromide (577-19-5)

Conditions	Yield
With dipotassium peroxodisulfate; silver(I) acetate In acetonitrile at 100℃; for 24h;	43%

2-bromo-N,N-dimethylaniline (698-00-0) → 2-nitrophenyl bromide (577-19-5)

Conditions	Yield
With tert.-butylhydroperoxide; ammonium iodide; water In dimethyl sulfoxide at 90℃; for 6h; Sealed tube;	38%

bromobenzene (108-86-1) + nitro acetate (591-09-3) → 2-nitrophenyl bromide (577-19-5) + para-nitrophenyl bromide (586-78-7)

Conditions	Yield
With acetic anhydride at 0℃;

bromobenzene (108-86-1) → 2-nitrophenyl bromide (577-19-5)

Conditions	Yield
beim Nitrieren;
With nitric acid; acetic anhydride; H5PV2Mo10O40(1,11) for 1h; Heating;	62 % Chromat.

3-bromo-4-nitroaniline (40787-96-0) → 2-nitrophenyl bromide (577-19-5)

Conditions	Yield
With ethanol; mixture of gaseous nitrogen oxides

bromobenzene (108-86-1) + nitro acetate (591-09-3) + acetic anhydride (108-24-7) → 2-nitrophenyl bromide (577-19-5) + para-nitrophenyl bromide (586-78-7)

Conditions	Yield
at 25℃;
at 0℃;

silver(I) o-nitrobenzoate (72247-99-5) → 2-nitrophenyl bromide (577-19-5)

Conditions	Yield
With tetrachloromethane; bromine

bromobenzene (108-86-1) → bromochlorobenzene (106-39-8) + 2-bromo-1-chlorobenzene (694-80-4) + 2-nitrophenyl bromide (577-19-5) + para-nitrophenyl bromide (586-78-7)

Conditions	Yield
With Nitryl chloride; trifluoroacetic acid at 20℃; for 8h; Product distribution; Mechanism;

bromobenzene (108-86-1) → 3-Bromonitrobenzene (585-79-5) + 2-nitrophenyl bromide (577-19-5) + para-nitrophenyl bromide (586-78-7)

Conditions	Yield
With nitric acid In water at 25℃;	A 0.4 % Chromat. B 36.3 % Chromat. C 62.8 % Chromat.
With dinitrogen tetraoxide; N,N,N,N-tetraethylammonium tetrafluoroborate In sulfolane at 30℃; electrochemical process; Yield given. Yields of byproduct given;
With nitric acid; ytterbium(III) triflate In 1,2-dichloro-ethane for 12h; Heating; Title compound not separated from byproducts;

bromine (7726-95-6) + 1,2-Dinitrobenzene (528-29-0) → 2-nitrophenyl bromide (577-19-5)

Conditions	Yield
at 180℃;

ethyl bromide (74-96-4) + bromine (7726-95-6) + nitrobenzene (98-95-3) → 3-Bromonitrobenzene (585-79-5) + 2-nitrophenyl bromide (577-19-5) + para-nitrophenyl bromide (586-78-7)

Conditions	Yield
Kinetics; Beschuss mit langsamen Neutronen;

bromobenzene (108-86-1) + nitric acid (7697-37-2) → 2-nitrophenyl bromide (577-19-5) + para-nitrophenyl bromide (586-78-7)

Conditions	Yield
Product distribution;

aluminium trichloride (7446-70-0) + bromobenzene (108-86-1) + dinitrogen tetraoxide (10544-72-6) → 2-nitrophenyl bromide (577-19-5) + para-nitrophenyl bromide (586-78-7)

Conditions	Yield
at 0 - 10℃;

1-Bromo-2-iodobenzene (583-55-1) + nitric acid (7697-37-2) → 2-nitrophenyl bromide (577-19-5) + bromoiodonitrobenzene

Conditions	Yield
at -10℃;

2-nitrophenyl bromide (577-19-5) → N-(2-bromophenyl)hydroxylamine (35758-75-9)

Conditions	Yield
With 5% rhodium-on-charcoal; hydrazine hydrate In tetrahydrofuran at 0℃; for 2.5h; Inert atmosphere;	100%
With 5% rhodium-on-charcoal; hydrazine hydrate In tetrahydrofuran at 0℃; Inert atmosphere;	100%
With methyldiazene In acetonitrile at 28℃; for 3.5h; Irradiation; Sealed tube; Inert atmosphere;	95%

2-nitrophenyl bromide (577-19-5) → ortho-nitrofluorobenzene (1493-27-2)

Conditions	Yield
With Cu(Ph3P)3F In N,N-dimethyl-formamide at 170℃; for 5h;	100%

trans-geranyl bromide (6138-90-5) + 2-nitrophenyl bromide (577-19-5) → 1-((E)-3,7-Dimethyl-octa-2,6-dienyl)-2-nitro-benzene

Conditions	Yield
Stage #1: 2-nitrophenyl bromide With phenyllithium In tetrahydrofuran at -78℃; for 0.0833333h; Stage #2: trans-geranyl bromide With N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78℃; for 3h;	100%

2-nitrophenyl bromide (577-19-5) + benzyl bromide (100-39-0) → 2-nitrodiphenylmethane (5840-40-4)

Conditions	Yield
Stage #1: 2-nitrophenyl bromide With phenyllithium In tetrahydrofuran at -78℃; for 0.0833333h; Stage #2: benzyl bromide With N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78℃; for 3h;	100%

2-nitrophenyl bromide (577-19-5) + 2-methylbenzyl bromide (89-92-9) → C14H13NO2

Conditions	Yield
Stage #1: 2-nitrophenyl bromide With phenyllithium In tetrahydrofuran at -78℃; for 0.0833333h; Stage #2: 2-methylbenzyl bromide With N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78℃; for 3h;	100%

2-nitrophenyl bromide (577-19-5) + prenyl bromide (870-63-3) → 1-(3-methylbut-2-en-1-yl)-2-nitrobenzene (421571-68-8)

Conditions	Yield
Stage #1: 2-nitrophenyl bromide With phenyllithium In tetrahydrofuran at -78℃; for 0.0833333h; Stage #2: prenyl bromide With N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78℃; for 3h;	100%
Stage #1: 2-nitrophenyl bromide With phenyllithium In tetrahydrofuran at -78℃; Stage #2: prenyl bromide With N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78℃; for 3h;	100%

2-nitrophenyl bromide (577-19-5) + 8-methoxy-naphthalen-1-ylboronic acid → 8-methoxy-1-(2'-nitrophenyl)naphthalene (683764-60-5)

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 100℃; for 3.5h; Suzuki-Miyaura coupling reaction;	100%

2-nitrophenyl bromide (577-19-5) + (S)-2,2'-diamino-1,1'-binaphthalene (18531-95-8) → (S)-(+)-N2,N2'-bis(2-nitrophenyl)-1,1'-binaphthalenyl-2,2'-diamine

Conditions	Yield
With DPE-Phos; caesium carbonate; tris(dibenzylideneacetone)dipalladium (0) In toluene at 80℃; for 48h;	100%
With caesium carbonate; bis[2-(diphenylphosphino)phenyl] ether; tris(dibenzylideneacetone)dipalladium (0) In toluene at 80℃; for 48h;	100%

2-nitrophenyl bromide (577-19-5) + 10-hexyl-3,7-bis(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-10H-phenothiazine (405198-30-3) → 10-hexyl-3,7-bis(2-nitrophenyl)-10H-phenothiazine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 18h; Suzuki coupling;	100%

2-nitrophenyl bromide (577-19-5) + 5-chloroanthranilic acid (635-21-2) → 5-Chloro-2-(2-nitro-phenylamino)-benzoic acid (97027-31-1)

Conditions	Yield
With copper; potassium carbonate In pentan-1-ol at 150℃; Ullman coupling;	100%

2-nitrophenyl bromide (577-19-5) + phenylboronic acid (98-80-6) → 2-nitrobiphenyl (86-00-0)

Conditions	Yield
With potassium carbonate In water; isopropyl alcohol at 100℃; for 10h; Suzuki-Miyaura Coupling; Inert atmosphere;	100%
With potassium phosphate; second generation phosphine dendrimer-stabilized palladium In 1,4-dioxane for 20h; Suzuki coupling; Heating;	99%
With potassium phosphate tribasic heptahydrate In 1,4-dioxane for 20h; Suzuki coupling; Reflux;	99%

2-nitrophenyl bromide (577-19-5) + N-butylamine (109-73-9) → o-Nitro-N-n-butylaminobenzene (42896-66-2)

Conditions	Yield
In dimethyl sulfoxide at 80℃;	100%
In dimethyl sulfoxide at 80℃;	100%
In dimethyl sulfoxide

4-dibenzofurylboronic acid (100124-06-9) + 2-nitrophenyl bromide (577-19-5) → 4-(2-nitrophenyl)dibenzo[b,d]furan (1246308-80-4)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene for 12h; Reflux;	100%
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene for 24h; Reflux;	99.7%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 3h; Reflux;	98%

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (942070-38-4) + 2-nitrophenyl bromide (577-19-5) → 1-tert-butyl 2-methyl 4-(2-nitrophenyl)-1H-pyrrole-1,2-dicarboxylate

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 35℃; for 16h; Suzuki Coupling; Sealed tube; Inert atmosphere;	100%

4-methyl-6-(methyloxy)-3-pyridinamine (6635-91-2) + 2-nitrophenyl bromide (577-19-5) → 6-methoxy-4-methyl-N-(2-nitrophenyl)pyridin-3-amine

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium tert-pentoxide; XPhos In 1,4-dioxane at 110℃;	100%

2-nitrophenyl bromide (577-19-5) + N2,3-dimethylpyridine-2,5-diamine → N2,3-dimethyl-N5-(2-nitrophenyl)pyridine-2,5-diamine

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium tert-pentoxide; XPhos In 1,4-dioxane at 110℃;	100%

1-methyl-1H-indazol-5-amine (50593-24-3) + 2-nitrophenyl bromide (577-19-5) → 1-methyl-N-(2-nitrophenyl)-1H-indazol-5-amine

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); XPhos In 1,4-dioxane at 110℃;	100%

(S)-2,2',3,3'-tetrahydro-1,1'-spirobi-[indene]-7,7'-diamine + 2-nitrophenyl bromide (577-19-5) → (S)-N7,N7'-bis(2-nitrophenyl)-2,2',3,3'-tetrahydro-1,1'-spirobi[indene]-7,7'-diamine

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; bis[2-(diphenylphosphino)phenyl] ether In toluene at 80℃; for 48h; Buchwald-Hartwig Coupling; Inert atmosphere;	100%

2-nitrophenyl bromide (577-19-5) → 2-bromoaniline (615-36-1)

Conditions	Yield
With hydrogen In tetrahydrofuran; water at 120℃; under 22502.3 Torr; for 4h; Autoclave;	99%
With hydrazine In ethanol at 80℃; for 0.333333h; Catalytic behavior; chemoselective reaction;	99.6%
With hydrogen In water at 120℃; under 15001.5 Torr; for 5h; Green chemistry; chemoselective reaction;	99%

2-nitrophenyl bromide (577-19-5) + methylamine (74-89-5) → 2-nitro-N-methylaniline (612-28-2)

Conditions	Yield
With copper In water at 100℃; for 12h; Ullmann reaction;	99.5%
With ethanol at 150℃; unter Druck;
In ethanol at 150℃;

2-nitrophenyl bromide (577-19-5) + 4-Chlorophenylboronic acid (1679-18-1) → 4'-chloro-2-nitrobiphenyl (6271-80-3)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 5h; Inert atmosphere;	99%
With tetrabutylammomium bromide; sodium acetate; C50H63Cl2N3Pd; sodium carbonate In ethanol; water at 90℃; for 24h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Suzuki-Miyaura Coupling;	99.2%
With C30H24N3OPPd; potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide for 1h; Suzuki Coupling; Reflux;	75%

2-nitrophenyl bromide (577-19-5) + 2-Chloroaniline (95-51-2) → N-(2-chlorophenyl)-N-(2-nitrophenyl)amine (74002-26-9)

Conditions	Yield
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium (0) In toluene at 110℃;	99%
With sodium acetate; nitrobenzene
With copper; potassium carbonate at 160℃;

2-nitrophenyl bromide (577-19-5) + trimethylsilylacetylene (1066-54-2) → trimethyl((2-nitrophenyl)ethynyl)silane (75867-47-9)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine for 4h; Inert atmosphere;	99%
With triethylamine; bis-triphenylphosphine-palladium(II) chloride at 20℃; for 48h;	96%
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 20℃;	89%

2-nitrophenyl bromide (577-19-5) + 4-methylphenylboronic acid (5720-05-8) → 4-methyl-2'-nitrobiphenyl (70680-21-6)

Conditions	Yield
With palladium diacetate; 4-Ph2P-C6H4-2-N-glucosamine; sodium carbonate In tetrahydrofuran; ethanol; water at 60℃; for 18h;	99%
With caesium carbonate; [PdCl(NNCNHC-nBu)]BF4 In water; N,N-dimethyl-formamide at 80℃; for 0.5h; Suzuki-Miyaura reaction;	98%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane at 100℃; for 12h;	97%

farnesyl bromide (24163-93-7, 24163-94-8, 56881-57-3, 6874-67-5, 28290-41-7) + 2-nitrophenyl bromide (577-19-5) → 2-farnesylnitrobenzene

Conditions	Yield
Stage #1: 2-nitrophenyl bromide With phenyllithium In tetrahydrofuran at -78℃; for 0.0833333h; Stage #2: farnesyl bromide With N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78℃; for 3h;	99%

2-nitrophenyl bromide (577-19-5) + 3-methoxyphenylboronic acid (10365-98-7) → 2-(3-Methoxyphenyl)nitrobenzene (92017-95-3)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 5h; Inert atmosphere;	99%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane at 110℃; for 5h;	93%
With potassium carbonate; Pd(PPh3)4 In 1,2-dimethoxyethane; water; ethyl acetate
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 90℃; for 12h; Inert atmosphere;

1,1'-biphenyl-2,2'-diamine (1454-80-4) + 2-nitrophenyl bromide (577-19-5) → N,N'-bis-(2-nitro-phenyl)-biphenyl-2,2'-diyldiamine (860590-00-7)

Conditions	Yield
With caesium carbonate; bis[2-(diphenylphosphino)phenyl] ether; tris(dibenzylideneacetone)dipalladium (0) In toluene at 80℃; for 48h;	99%

2-nitrophenyl bromide (577-19-5) + phenyl trimethylsiloxane (2996-92-1) → 2-nitrobiphenyl (86-00-0)

Conditions	Yield
With sodium hydroxide; palladium diacetate at 60℃; for 2h; Hiyama reaction;	99%
With tetrabutyl ammonium fluoride; caesium carbonate In 1,4-dioxane; water at 80℃; for 7h; Hiyama Coupling; chemoselective reaction;	83%
With trans-[1,3-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene]PdCl2(NC5H5); sodium hydroxide In 1,4-dioxane; water at 80℃; for 16h; Hiyama cross-coupling;	> 99 %Chromat.
With cis-{1-benzyl-3-methyl-4-phenyl-1,2,3-triazol-5-ylidene}PdI2(PPh3)*acetonitrile; sodium hydroxide In 1,4-dioxane; water at 80℃; for 4h; Catalytic behavior; Reagent/catalyst; Hiyama Coupling;	84 %Chromat.

2-nitrophenyl bromide (577-19-5) + N-methylaniline (100-61-8) → 2-nitro-N-methyl-N-phenylaniline (52997-62-3)

Conditions	Yield
With caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 85℃; for 20.25h;	99%
With C31H38N5P; caesium carbonate; bis(dibenzylideneacetone)-palladium(0) In tert-Amyl alcohol at 100℃; Inert atmosphere;	94.33%
With C31H38N5P; caesium carbonate; bis(dibenzylideneacetone)-palladium(0) In tert-Amyl alcohol at 100℃; Buchwald-Hartwig Coupling; Inert atmosphere;	94.33%

Upstream product

• 108-86-1 bromobenzene 
• 591-09-3 nitro acetate 
• 108-24-7 acetic anhydride 
• 88-74-4 2-nitro-aniline 
• 609-73-4 o-nitroiodobenzene 
• 98-95-3 nitrobenzene 
• 552-16-9 ortho-nitrobenzoic acid 
• 7726-95-6 bromine 
• 528-29-0 1,2-Dinitrobenzene 
• 583-55-1 1-Bromo-2-iodobenzene 
• 7697-37-2 nitric acid 
• 6293-87-4 o-nitrophenylhydrazine hydrochloride 
• 698-00-0 2-bromo-N,N-dimethylaniline 
• 615-36-1 2-bromoaniline 

Downstream Products

• 5320-98-9 N-(2-nitrophenyl)morpholine 
• 115581-68-5 2-nitro-N-(3-piperidino-propyl)-aniline 
• 91-22-5 quinoline 
• 4171-83-9 2-nitrophenyl phenyl sulfide 
• 102442-84-2 2′-nitrophenyl-1-pyrene 
• 412340-24-0 1-nitro-2-(2-nitro-phenyl)-naphthalene 
• 236102-72-0 2'-nitro-biphenyl-3-carboxylic acid 
• 247223-88-7 N-Methyl-N-(2-nitrophenyl)anthranilsaeure 
• 612-36-2 2-nitro-N-(4-nitrophenyl)benzenamine 
• 122859-66-9 2-methyl-2’-nitrodiphenylamine-6-carboxylic acid 
• 27147-69-9 (2-amino-phenyl)-(4-amino-phenyl)-sulfone 
• 18514-06-2 acetic acid-[4-(2-nitro-benzenesulfonyl)-anilide] 
• 876497-37-9 [2-(2-nitro-anilino)-phenyl]-arsonic acid 
• 858458-21-6 2,4-dimethyl-1-(2-nitro-phenyl)-naphthalene 

Relevant articles and documents

Nitration of deactivated aromatic compounds via mechanochemical reaction

A variety of deactivated arenes were nitrated to their corresponding nitro derivatives in excellent yields under high-speed ball milling condition using Fe(NO3)3·9H2O/P2O5 as nitrating reagent. A radical involved mechanism was proposed for this facial, eco-friendly, safe, and effective nitration reaction.

Two-Phase Electrochemical Generation of Aryldiazonium Salts: Application in Electrogenerated Copper-Catalyzed Sandmeyer Reactions

The electrochemical generation of aryldiazonium salts from nitroarenes in a two-phase system (ethyl acetate/water) was reported for the first time. Some compounds including azo, azosulfone, and arylazides were prepared in good yields with good purity. Cathodically generated aryldiazoniums and anodically produced copper(Ι) ions were used to perform Sandmeyer reactions. To improve the method, an H-type self-driving cell equipped with a Zn rod as an anode was introduced and used for two-phase aryldiazonium production.

Dehydroxyalkylative halogenation of C(aryl)-C bonds of aryl alcohols

We herein report Cu mediated side-directed dehydroxyalkylative halogenation of aryl alcohols. C(aryl)-C bonds of aryl alcohols were effectively cleaved, affording the corresponding aryl chlorides, bromides and iodides in excellent yields. Aryl alcohols could serve as both aromatic electrophilic and radical synthetic equivalents during the reaction.