1-Bromo-2-nitrobenzene supplier

Name
1-Bromo-2-nitrobenzene
EINECS 209-409-0
CAS No. 577-19-5
Article Data129
CAS DataBase
Density 1.719 g/cm³
Solubility insoluble in water
Melting Point 40-42 °C(lit.)
Formula C₆H₄BrNO₂
Boiling Point 261 °C at 760 mmHg
Molecular Weight 202.007
Flash Point 87.8 °C
Transport Information UN 3459 6.1/PG 3
Appearance white to light yellow crystal powder
Safety 36/37-36/37/39-26-22
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xn, Xi
Synonyms 2-Bromo-1-nitrobenzene;2-Bromonitrobenzene;2-Nitro-1-bromobenzene;2-Nitrobromobenzene;2-Nitrophenyl bromide;NSC 403836;o-Bromonitrobenzene;o-Nitrobromobenzene;o-Nitrophenyl bromide;
PSA 45.82000
LogP 2.88050

Synthetic route

: 552-16-9
ortho-nitrobenzoic acid

: 577-19-5
2-nitrophenyl bromide

Conditions

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%

: 6319-40-0
4-bromo-3-nitrobenzoic acid

: 577-19-5
2-nitrophenyl bromide

Conditions

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

: 2-nitrobenzenediazonium o-benzenedisulfonamide

: 577-19-5
2-nitrophenyl bromide

Conditions

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%

: 244205-40-1
(2-bromophenyl)boronic acid

: 577-19-5
2-nitrophenyl bromide

Conditions

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

: 577-19-5
2-nitrophenyl bromide

Conditions

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

: 88-74-4
2-nitro-aniline

: 577-19-5
2-nitrophenyl bromide

Conditions

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%

: 609-73-4
o-nitroiodobenzene

: 577-19-5
2-nitrophenyl bromide

Conditions

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

: 5570-19-4
2-nitrophenylboronic acid

: 577-19-5
2-nitrophenyl bromide

Conditions

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

: 98-95-3
nitrobenzene

: 577-19-5
2-nitrophenyl bromide

Conditions

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%

: 108-86-1
bromobenzene

A: 577-19-5
2-nitrophenyl bromide

B: 586-78-7
para-nitrophenyl bromide

Conditions

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%

: 615-36-1
2-bromoaniline

: 577-19-5
2-nitrophenyl bromide

Conditions

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℃;

: 365-33-3
2-nitrobenzenediazonium tetrafluoroborate

: 577-19-5
2-nitrophenyl bromide

Conditions

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

: 528-29-0
1,2-Dinitrobenzene

: 577-19-5
2-nitrophenyl bromide

Conditions

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%

: 132993-22-7
2-nitrophenyl trifluoromethanesulfonate

: 577-19-5
2-nitrophenyl bromide

Conditions

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

: 6293-87-4
o-nitrophenylhydrazine hydrochloride

: 577-19-5
2-nitrophenyl bromide

Conditions

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

: 101420-81-9
3-Bromo-4-nitrobenzoic acid

: 577-19-5
2-nitrophenyl bromide

Conditions

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

: 698-00-0
2-bromo-N,N-dimethylaniline

: 577-19-5
2-nitrophenyl bromide

Conditions

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

: 108-86-1
bromobenzene

: 591-09-3
nitro acetate

A: 577-19-5
2-nitrophenyl bromide

B: 586-78-7
para-nitrophenyl bromide

Conditions

Conditions	Yield
With acetic anhydride at 0℃;

...Expand

: 108-86-1
bromobenzene

: 577-19-5
2-nitrophenyl bromide

Conditions

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

: 40787-96-0
3-bromo-4-nitroaniline

: 577-19-5
2-nitrophenyl bromide

Conditions

Conditions	Yield
With ethanol; mixture of gaseous nitrogen oxides

: 108-86-1
bromobenzene

: 591-09-3
nitro acetate

: 108-24-7
acetic anhydride

A: 577-19-5
2-nitrophenyl bromide

B: 586-78-7
para-nitrophenyl bromide

Conditions

Conditions	Yield
at 25℃;
at 0℃;

...Expand

: 72247-99-5
silver(I) o-nitrobenzoate

: 577-19-5
2-nitrophenyl bromide

Conditions

Conditions	Yield
With tetrachloromethane; bromine

: 108-86-1
bromobenzene

A: 106-39-8
bromochlorobenzene

B: 694-80-4
2-bromo-1-chlorobenzene

C: 577-19-5
2-nitrophenyl bromide

D: 586-78-7
para-nitrophenyl bromide

Conditions

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

...Expand

: 108-86-1
bromobenzene

A: 585-79-5
3-Bromonitrobenzene

B: 577-19-5
2-nitrophenyl bromide

C: 586-78-7
para-nitrophenyl bromide

Conditions

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;

...Expand

: 7726-95-6
bromine

: 528-29-0
1,2-Dinitrobenzene

: 577-19-5
2-nitrophenyl bromide

Conditions

Conditions	Yield
at 180℃;

: 74-96-4
ethyl bromide

: 7726-95-6
bromine

: 98-95-3
nitrobenzene

A: 585-79-5
3-Bromonitrobenzene

B: 577-19-5
2-nitrophenyl bromide

C: 586-78-7
para-nitrophenyl bromide

Conditions

Conditions	Yield
Kinetics; Beschuss mit langsamen Neutronen;

...Expand

: 108-86-1
bromobenzene

: 7697-37-2
nitric acid

A: 577-19-5
2-nitrophenyl bromide

B: 586-78-7
para-nitrophenyl bromide

Conditions

Conditions	Yield
Product distribution;

...Expand

: 7446-70-0
aluminium trichloride

: 108-86-1
bromobenzene

: 10544-72-6
dinitrogen tetraoxide

A: 577-19-5
2-nitrophenyl bromide

B: 586-78-7
para-nitrophenyl bromide

Conditions

Conditions	Yield
at 0 - 10℃;

...Expand

: 583-55-1
1-Bromo-2-iodobenzene

: 7697-37-2
nitric acid

A: 577-19-5
2-nitrophenyl bromide

B bromoiodonitrobenzene: bromoiodonitrobenzene

Conditions

Conditions	Yield
at -10℃;

...Expand

: 577-19-5
2-nitrophenyl bromide

: 35758-75-9
N-(2-bromophenyl)hydroxylamine

Conditions

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%

: 577-19-5
2-nitrophenyl bromide

: 1493-27-2
ortho-nitrofluorobenzene

Conditions

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

: 6138-90-5
trans-geranyl bromide

: 577-19-5
2-nitrophenyl bromide

: 1-((E)-3,7-Dimethyl-octa-2,6-dienyl)-2-nitro-benzene

Conditions

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%

: 577-19-5
2-nitrophenyl bromide

: 100-39-0
benzyl bromide

: 5840-40-4
2-nitrodiphenylmethane

Conditions

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%

: 577-19-5
2-nitrophenyl bromide

: 89-92-9
2-methylbenzyl bromide

: C14H13NO2

Conditions

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%

: 577-19-5
2-nitrophenyl bromide

: 870-63-3
prenyl bromide

: 421571-68-8
1-(3-methylbut-2-en-1-yl)-2-nitrobenzene

Conditions

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%

: 577-19-5
2-nitrophenyl bromide

: 8-methoxy-naphthalen-1-ylboronic acid

: 683764-60-5
8-methoxy-1-(2'-nitrophenyl)naphthalene

Conditions

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

: 577-19-5
2-nitrophenyl bromide

: 18531-95-8
(S)-2,2'-diamino-1,1'-binaphthalene

: (S)-(+)-N2,N2'-bis(2-nitrophenyl)-1,1'-binaphthalenyl-2,2'-diamine

Conditions

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%

: 577-19-5
2-nitrophenyl bromide

: 405198-30-3
10-hexyl-3,7-bis(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-10H-phenothiazine

: 10-hexyl-3,7-bis(2-nitrophenyl)-10H-phenothiazine

Conditions

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

: 577-19-5
2-nitrophenyl bromide

: 635-21-2
5-chloroanthranilic acid

: 97027-31-1
5-Chloro-2-(2-nitro-phenylamino)-benzoic acid

Conditions

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

: 577-19-5
2-nitrophenyl bromide

: 98-80-6
phenylboronic acid

: 86-00-0
2-nitrobiphenyl

Conditions

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%

: 577-19-5
2-nitrophenyl bromide

: 109-73-9
N-butylamine

: 42896-66-2
o-Nitro-N-n-butylaminobenzene

Conditions

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

: 100124-06-9
4-dibenzofurylboronic acid

: 577-19-5
2-nitrophenyl bromide

: 1246308-80-4
4-(2-nitrophenyl)dibenzo[b,d]furan

Conditions

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%

: 942070-38-4
4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

: 577-19-5
2-nitrophenyl bromide

: 1-tert-butyl 2-methyl 4-(2-nitrophenyl)-1H-pyrrole-1,2-dicarboxylate

Conditions

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%

: 6635-91-2
4-methyl-6-(methyloxy)-3-pyridinamine

: 577-19-5
2-nitrophenyl bromide

: 6-methoxy-4-methyl-N-(2-nitrophenyl)pyridin-3-amine

Conditions

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

: 577-19-5
2-nitrophenyl bromide

: N2,3-dimethylpyridine-2,5-diamine

: N2,3-dimethyl-N5-(2-nitrophenyl)pyridine-2,5-diamine

Conditions

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

: 50593-24-3
1-methyl-1H-indazol-5-amine

: 577-19-5
2-nitrophenyl bromide

: 1-methyl-N-(2-nitrophenyl)-1H-indazol-5-amine

Conditions

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

: 577-19-5
2-nitrophenyl bromide

: (S)-N7,N7'-bis(2-nitrophenyl)-2,2',3,3'-tetrahydro-1,1'-spirobi[indene]-7,7'-diamine

Conditions

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%

: 577-19-5
2-nitrophenyl bromide

: 615-36-1
2-bromoaniline

Conditions

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%

: 577-19-5
2-nitrophenyl bromide

: 74-89-5
methylamine

: 612-28-2
2-nitro-N-methylaniline

Conditions

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

: 577-19-5
2-nitrophenyl bromide

: 1679-18-1
4-Chlorophenylboronic acid

: 6271-80-3
4'-chloro-2-nitrobiphenyl

Conditions

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%

: 577-19-5
2-nitrophenyl bromide

: 95-51-2
2-Chloroaniline

: 74002-26-9
N-(2-chlorophenyl)-N-(2-nitrophenyl)amine

Conditions

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℃;

: 577-19-5
2-nitrophenyl bromide

: 1066-54-2
trimethylsilylacetylene

: 75867-47-9
trimethyl((2-nitrophenyl)ethynyl)silane

Conditions

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%

: 577-19-5
2-nitrophenyl bromide

: 5720-05-8
4-methylphenylboronic acid

: 70680-21-6
4-methyl-2'-nitrobiphenyl

Conditions

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%

: 24163-93-7, 24163-94-8, 56881-57-3, 6874-67-5, 28290-41-7
farnesyl bromide

: 577-19-5
2-nitrophenyl bromide

: 2-farnesylnitrobenzene

Conditions

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%

: 577-19-5
2-nitrophenyl bromide

: 10365-98-7
3-methoxyphenylboronic acid

: 92017-95-3
2-(3-Methoxyphenyl)nitrobenzene

Conditions

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;

: 1454-80-4
1,1'-biphenyl-2,2'-diamine

: 577-19-5
2-nitrophenyl bromide

: 860590-00-7
N,N'-bis-(2-nitro-phenyl)-biphenyl-2,2'-diyldiamine

Conditions

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

: 577-19-5
2-nitrophenyl bromide

: 2996-92-1
phenyl trimethylsiloxane

: 86-00-0
2-nitrobiphenyl

Conditions

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.

: 577-19-5
2-nitrophenyl bromide

: 100-61-8
N-methylaniline

: 52997-62-3
2-nitro-N-methyl-N-phenylaniline

Conditions

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%

1-Bromo-2-nitrobenzene Consensus Reports

Reported in EPA TSCA Inventory.

1-Bromo-2-nitrobenzene Specification

The IUPAC name of 2-Nitrobromobenzene is 1-bromo-2-nitrobenzene. With the CAS registry number 577-19-5, it is also named as Benzene, 1-bromo-2-nitro-. The product's categories are Aromatic Hydrocarbons (substituted) & Derivatives; Benzene Derivates; Miscellaneous; Bromine Compounds; Nitro Compounds; Nitrogen Compounds; Organic Building Blocks. It is white to light yellow crystal powder which is easily soluble in ethanol, soluble in ether and benzene, insoluble in water. What's more, it is stable, combustible and incompatible with strong bases, strong oxidizing agents. When heated to decomposition it emits toxic vapors of NO_x and Br⁻. So the storage environment should be well- ventilated, low-temperature and dry. Keep 2-Nitrobromobenzene separate from oxidants and food additives.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.52; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.52; (4)ACD/LogD (pH 7.4): 2.52; (5)ACD/BCF (pH 5.5): 48.44; (6)ACD/BCF (pH 7.4): 48.44; (7)ACD/KOC (pH 5.5): 559.63; (8)ACD/KOC (pH 7.4): 559.63; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.605; (13)Molar Refractivity: 40.48 cm³; (14)Molar Volume: 117.4 cm³; (15)Polarizability: 16.05×10^-24 cm³; (16)Surface Tension: 50.5 dyne/cm; (17)Enthalpy of Vaporization: 47.86 kJ/mol; (18)Vapour Pressure: 0.0192 mmHg at 25°C; (19)Exact Mass: 200.942541; (20)MonoIsotopic Mass: 200.942541; (21)Topological Polar Surface Area: 45.8; (22)Heavy Atom Count: 10; (23)Complexity: 134.

Preparation of 2-Nitrobromobenzene: It can be obtained by o-nitroaniline. The mixture of o-nitroaniline and sulfuric acid is cooled to 0-5 °C. Adding sodium nitrite solution slowly under stirring. When the reaction makes potassium iodide starch test paper turn blue, we stops. The obtained diazonium salt solution adds to 40 °C CuBr solution while stirring. After cooling, it is extracted with diethyl ether. The extract is washed by lye, hydrochloric acid and water. Then we can get the product after the recovery of ether. The yield is 70%.

Uses of 2-Nitrobromobenzene: It is used in organic synthesis. It also can react with 2-methylamino-benzoic acid to get N-methyl-N-(2-nitro-phenyl)-anthranilic acid. This reaction needs reagents potassium carbonate, copper powder and isoamyl alcohol.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. So people should not breathe dust. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
1. SMILES:O=[N+]([O-])c1ccccc1Br
2. InChI:InChI=1/C6H4BrNO2/c7-5-3-1-2-4-6(5)8(9)10/h1-4H
3. InChIKey:ORPVVAKYSXQCJI-UHFFFAOYAL

Product Name

1-Bromo-2-nitrobenzene

Synthetic route

1-Bromo-2-nitrobenzene Consensus Reports

1-Bromo-2-nitrobenzene Specification

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