Conditions | Yield |
---|---|
With hydrogen bromide; dihydrogen peroxide In methanol at 0 - 20℃; for 12h; | 99% |
With HMTAB In dichloromethane at 20℃; for 0.5h; | 98% |
With 1-butyl-3-methylpyridinium tribromide at 20℃; | 98% |
4-Bromo-2-nitroaniline
Conditions | Yield |
---|---|
With potassium carbonate; dimethyl sulfoxide; thiophenol In acetonitrile at 100℃; for 24h; | 96% |
4-Bromo-2-nitroaniline
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol at 90℃; for 8h; | 92% |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol at 80℃; for 12h; | 86% |
With hydrogenchloride In tetrahydrofuran Heating; | 77% |
With hydrogenchloride |
Conditions | Yield |
---|---|
With dihydrogen peroxide; potassium bromide In water; acetonitrile | A 15% B 82% |
With dihydrogen peroxide; potassium bromide; HZSM-5 In acetic acid at 20℃; for 4h; Bromination; | A 15% B 77% |
With N-Bromosuccinimide; acetic acid at 34.84 - 89.84℃; for 5.5h; | A 6.81 g B 74% |
With dihydrogen peroxide; ammonium bromide; acetic acid at 20℃; for 4h; | |
Stage #1: 2-nitro-aniline With dihydrogen peroxide; acetic acid; potassium bromide In water at 20℃; for 3h; Stage #2: With sodium hydrogencarbonate In diethyl ether; water regioselective reaction; |
Conditions | Yield |
---|---|
With 4-nitro-4-methyl-2,3,5,6-tetrabromo-2,5-cyclohexadien-1-one In trifluoroacetic acid for 3h; Ambient temperature; | 70% |
With nitric acid; acetic acid | |
Multi-step reaction with 3 steps 1: Diazotization.Zersetzung des Diazoniumperbromids mit Alkohol 2: beim Nitrieren 3: alcohol; ammonia / 200 - 210 °C View Scheme | |
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane 2: nitric acid; acetic anhydride / dichloromethane 3: hydrogenchloride / water / Reflux View Scheme | |
Multi-step reaction with 3 steps 1: pyridine / tetrahydrofuran / 16 h / 20 °C / Cooling with ice 2: nitric acid; copper(II) nitrate hydrate; oxygen / acetonitrile; water / 4 h / 50 °C / 760.05 Torr 3: potassium carbonate; dimethyl sulfoxide; thiophenol / acetonitrile / 24 h / 100 °C View Scheme |
4-Bromo-2-nitroaniline
Conditions | Yield |
---|---|
Stage #1: N-(4-bromo-2-nitrophenyl) pyrimidin-2-amine With triethylsilane; trifluoroacetic acid at 50℃; Inert atmosphere; Stage #2: With acetic acid; hydrazine In methanol at 20℃; Inert atmosphere; regioselective reaction; | 68% |
4’-methoxy-2-nitroazobenzene
A
4-Bromo-2-nitroaniline
B
2,4-dibromo-6-nitroaniline
C
2-nitro-aniline
Conditions | Yield |
---|---|
With hydrogen bromide In acetic acid for 1h; Heating; | A 51% B 10% C 22% |
2-(4-bromophenyl)isoindoline-1,3-dione
A
4-Bromo-2-nitroaniline
B
4-bromo-3-nitroaniline
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid Erhitzen des Reaktionsprodukts mit 90prozentig.wss.Schwefelsaeure auf 130grad; |
Conditions | Yield |
---|---|
With ammonia; ethylene glycol at 120 - 130℃; | |
With ethanol; ammonia at 200 - 210℃; |
4-bromo-1-chloro-2-nitrobenzene
4-Bromo-2-nitroaniline
Conditions | Yield |
---|---|
With ethanol; ammonia at 160℃; |
Conditions | Yield |
---|---|
Bromieren und Verseifung des Reaktionsproduktes; |
4-Bromo-2-nitroaniline
Conditions | Yield |
---|---|
With ammonium hydroxide |
acetic acid-(N-bromo-2-nitro-anilide)
4-Bromo-2-nitroaniline
Conditions | Yield |
---|---|
With water |
N-(4-bromophenyl)-nitramine
4-Bromo-2-nitroaniline
Conditions | Yield |
---|---|
With hydrogen bromide |
Conditions | Yield |
---|---|
at 200 - 210℃; |
2-nitro-aniline
A
2-bromo-6-nitroaniline
B
4-Bromo-2-nitroaniline
C
2,4-dibromo-6-nitroaniline
Conditions | Yield |
---|---|
With sodium perborate; ammonium heptamolybdate; potassium bromide In acetic acid at 20℃; for 1.25h; Bromination; |
Conditions | Yield |
---|---|
With sodium periodate; potassium iodide; lithium bromide In water; acetic acid at 25℃; for 8h; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 92 percent / nitric acid / 0.17 h / -40 °C 2: 77 percent / aq. HCl / tetrahydrofuran / Heating View Scheme | |
Multi-step reaction with 2 steps 1: HNO3 / 8 min below 0 deg C, 8 min, RT. 2: 3N KOH / 24 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: alcoholic potash 2: glacial acetic acid; nitric acid View Scheme | |
Multi-step reaction with 2 steps 1: sulfuric acid; sodium nitrate 2: aqueous sulfuric acid View Scheme | |
Multi-step reaction with 2 steps 1: nitric acid; acetic anhydride / dichloromethane 2: hydrogenchloride / water / Reflux View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: chloroform; KHCO3; acid; bromine 2: acidified water View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: concentrated nitric acid 2: alcohol; ammonia / 160 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: beim Nitrieren 2: alcohol; ammonia / 200 - 210 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: bromine 2: concentrated nitric acid 3: alcohol; ammonia / 160 °C View Scheme |
dichloromethane
4-methylmorpholine N-oxide
5-benzimidazolecarboxylic acid
A
4-Bromo-2-nitroaniline
B
1H-benzo[d]imidazole-5-carbaldehyde
Conditions | Yield |
---|---|
With LiAlH4; tetrapropylammonium perruthennate In tetrahydrofuran; N,N-dimethyl-formamide | A 452 mg (32%, 2 steps) B n/a |
4-Bromo-2-nitroaniline
2-nitro-4-(pyridin-3-yl)benzenamine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,2-dimethoxyethane at 90℃; for 8h; Suzuki coupling; | 100% |
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 90℃; for 8h; |
4-Bromo-2-nitroaniline
cyclopropylboronic acid
4-cyclopropyl-2-nitro-phenylamine
Conditions | Yield |
---|---|
With potassium phosphate; palladium diacetate; catacxium A In water; toluene at 90℃; Inert atmosphere; | 100% |
With potassium phosphate; palladium diacetate; tricyclohexylphosphine In water; toluene at 100℃; for 12h; Inert atmosphere; | 89% |
With potassium phosphate; palladium diacetate; triphenylphosphine In toluene at 100℃; for 17h; Sealed tube; | 72% |
3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole
4-Bromo-2-nitroaniline
Conditions | Yield |
---|---|
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; caesium carbonate In 1,2-dimethoxyethane; water for 0.5h; Suzuki Coupling; | 100% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 90℃; for 16h; Inert atmosphere; | 88% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 90℃; for 16h; Inert atmosphere; | 88% |
Conditions | Yield |
---|---|
With potassium phosphate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) In ethanol; water for 8h; Inert atmosphere; Reflux; | 100% |
Conditions | Yield |
---|---|
With acetic acid at 95℃; for 7.5h; | 99.1% |
With acetic acid at 100℃; for 3h; | 94% |
With acetic acid at 100℃; for 5h; | 92.1% |
CYANAMID
4-Bromo-2-nitroaniline
7-bromo-1-oxido-1,2,4-benzotriazin-1-ium-3-amine
Conditions | Yield |
---|---|
Stage #1: CYANAMID; 4-Bromo-2-nitroaniline at 50 - 100℃; Stage #2: With hydrogenchloride In water at 100℃; for 3h; Stage #3: With sodium hydroxide In water at 100℃; for 1h; | 99% |
Stage #1: CYANAMID; 4-Bromo-2-nitroaniline In diethyl ether at 100℃; for 0.5h; Stage #2: With hydrogenchloride In diethyl ether; water at 50 - 110℃; for 1h; Stage #3: With sodium hydroxide In diethyl ether; water at 50 - 110℃; for 1h; | 79% |
Stage #1: CYANAMID; 4-Bromo-2-nitroaniline at 100℃; for 0.5h; Stage #2: With hydrogenchloride In water at 50 - 100℃; for 3h; Stage #3: With sodium hydroxide In water at 100℃; for 1h; | 60% |
4-Bromo-2-nitroaniline
1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
4-(1-methyl-1H-pyrazol-4-yl)-2-nitroaniline
Conditions | Yield |
---|---|
With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In ISOPROPYLAMIDE; water at 80℃; for 1h; Suzuki Coupling; | 99% |
With sodium carbonate In N,N-dimethyl acetamide; water at 80℃; for 1h; Inert atmosphere; | 99% |
With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In N,N-dimethyl acetamide; water at 80℃; for 1h; Suzuki Coupling; | 99% |
4-Bromo-2-nitroaniline
acrylic acid methyl ester
methyl (E)-3-(4′-bromo-2′-nitrophenyl)acrylate
Conditions | Yield |
---|---|
With tert.-butylnitrite; methanesulfonic acid; palladium diacetate; methoxybenzene In methanol at 0 - 25℃; for 48h; Reagent/catalyst; Heck Reaction; | 99% |
Stage #1: 4-Bromo-2-nitroaniline With tert.-butylnitrite In methanol at 0℃; for 0.5h; Stage #2: acrylic acid methyl ester With methanesulfonic acid; palladium diacetate In methanol at 0 - 25℃; Heck-Matsuda reaction; chemoselective reaction; | 98% |
With palladium diacetate; toluene-4-sulfonic acid In methanol at 60℃; for 1.5h; Inert atmosphere; chemoselective reaction; | 76% |
With tert.-butylnitrite In methanol at 25℃; for 24h; chemoselective reaction; | 74% |
Conditions | Yield |
---|---|
Stage #1: 4-Bromo-2-nitroaniline With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.166667h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 0 - 20℃; for 2h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
Stage #1: 4-Bromo-2-nitroaniline With potassium hydroxide In ethanol at 47 - 65℃; for 2h; Inert atmosphere; Stage #2: With sodium hypochlorite In ethanol; water at 2 - 20℃; for 19.5h; | 98% |
Stage #1: 4-Bromo-2-nitroaniline With potassium hydroxide In ethanol at 60℃; for 1h; Stage #2: With sodium hypochlorite at 0℃; for 1h; | |
Stage #1: 4-Bromo-2-nitroaniline With potassium hydroxide In ethanol at 47 - 65℃; for 2h; Stage #2: With sodium hypochlorite In ethanol; water at 5℃; for 1.5h; |
4-Bromo-2-nitroaniline
2-nitro-4-thiophen-2-yl-phenylamine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 3h; Suzuki-Miyaura coupling; | 98% |
With potassium carbonate; tris-(o-tolyl)phosphine; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water Suzuki coupling; |
cis,trans-2,5-dimethoxytetrahydrofuran
4-Bromo-2-nitroaniline
1-(4-bromo-2-nitrophenyl)-1H-pyrrole
Conditions | Yield |
---|---|
With acetic acid for 4h; Reflux; | 98% |
With acetic acid for 1h; Reflux; | 86% |
With acetic acid for 2h; Clauson-Kaas Synthesis; Reflux; |
Conditions | Yield |
---|---|
With sodium tetrachloroaurate(III) dihydrate; sodium 3-(diphenylphosphanyl)benzenesulfonate In water at 80℃; for 16h; Sealed tube; Green chemistry; | 98% |
4-Bromo-2-nitroaniline
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride; trifluoroacetic acid In dichloromethane at -5 - 0℃; for 2h; | 97.4% |
Conditions | Yield |
---|---|
With iron(III) chloride; hydrazine In methanol | 97% |
With hydrogenchloride; tin(ll) chloride at 65 - 70℃; for 1h; | 96% |
With tin(ll) chloride In ethanol Reduction; Heating; | 94% |
Conditions | Yield |
---|---|
With isopentyl nitrite at 25 - 90℃; for 2h; | 97% |
With isopentyl nitrite at 80 - 90℃; for 2h; | 76% |
4-Bromo-2-nitroaniline
isopentyl nitrite
4-bromo-1-methylsulfanyl-2-nitro-benzene
Conditions | Yield |
---|---|
In Dimethyldisulphide; ethyl acetate | 97% |
4-Bromo-2-nitroaniline
Conditions | Yield |
---|---|
With tert.-butylnitrite; boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; | 97% |
4-Bromo-2-nitroaniline
2-(trifluoromethyl)phenylboronic acid
3-nitro-2'-(trifluoromethyl)-[1,1'-biphenyl]-4-amine
Conditions | Yield |
---|---|
With sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,2-dimethoxyethane; water at 90℃; for 16h; Inert atmosphere; | 97% |
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane; water at 90℃; for 18h; Suzuki coupling; Inert atmosphere; | 97% |
With sodium carbonate; lithium chloride; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 80℃; Inert atmosphere; | |
With sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,2-dimethoxyethane; water at 90℃; for 16h; Inert atmosphere; |
4-Bromo-2-nitroaniline
2-trifluoromethoxyphenylboronic acid
3-nitro-2'-(trifluoromethoxy)-[1,1'-biphenyl]-4-amine
Conditions | Yield |
---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane; water at 90℃; for 18h; Suzuki coupling; Inert atmosphere; | 97% |
4-Bromo-2-nitroaniline
(4-bromo-2-nitrophenyl)hydrazine hydrochloride
Conditions | Yield |
---|---|
Stage #1: 4-Bromo-2-nitroaniline With hydrogenchloride In water at 40℃; for 2h; Stage #2: With sodium nitrite In water at -10℃; for 2h; Stage #3: With hydrogenchloride; tin(ll) chloride In water at -30 - -20℃; | 97% |
Conditions | Yield |
---|---|
With bis(triphenylphosphine)palladium(II)-chloride; triphenylphosphine In N,N-dimethyl-formamide at 120℃; | 96% |
Molecular structure of 4-Bromo-2-nitroaniline (CAS NO.875-51-4) is:
Product Name: 4-Bromo-2-nitroaniline
CAS Registry Number: 875-51-4
IUPAC Name: 4-bromo-2-nitroaniline
Molecular Weight: 217.0201 [g/mol]
Molecular Formula: C6H5BrN2O2
XLogP3: 1.9
H-Bond Donor: 1
H-Bond Acceptor: 3
Melting Point: 110-113 °C(lit.)
Surface Tension: 64.3 dyne/cm
Density: 1.812 g/cm3
Flash Point: 140.5 °C
Enthalpy of Vaporization: 54.94 kJ/mol
Boiling Point: 308.7 °C at 760 mmHg
Vapour Pressure: 0.00067 mmHg at 25°C
Product Categories: Amines and Anilines;Anilines, Aromatic Amines and Nitro Compounds;Amines;Phenyls & Phenyl-Het;Anilines, Amides & Amines;Bromine Compounds;Nitro Compounds;Phenyls & Phenyl-Het;C2 to C6;Nitrogen Compounds
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rat | LD | oral | > 500mg/kg (500mg/kg) | National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 12, 1953. |
Safty information about 4-Bromo-2-nitroaniline (CAS NO.875-51-4) is:
Hazard Codes: Xn,Xi
Risk Statements: 22-36/37/38-43-20/21/22
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
R43:May cause sensitization by skin contact.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
WGK Germany: 3
RTECS: BW9370000
Hazard Note: Irritant
HazardClass: IRRITANT, IRRITANT-HARMFUL
4-Bromo-2-nitroaniline , its cas register number is 875-51-4. It also can be called 2-Nitro-4-bromoaniline ; 4-Bromo-2-nitrobenzeneamine ; 4-Bromo-o-nitroaniline ; Aniline, 4-bromo-2-nitro- ; Benzenamine, 4-bromo-2-nitro- ; p-Bromo-o-nitroaniline ; Aniline, 4-bromo-2-nitro- ; Benzenamine, 4-bromo-2-nitro- .
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