4-bromo-2-nitrobenzylidene diethanoate
4-bromo-2-nitrobenzaldehyde
Conditions | Yield |
---|---|
With sulfuric acid In ethanol for 1.5h; Heating; | 93% |
With sulfuric acid | |
With sulfuric acid In ethanol | |
With hydrogenchloride In ethanol; water for 0.75h; Reflux; | |
With hydrogenchloride; water In ethanol for 0.75h; Reflux; |
(4-bromo-2-nitrophenyl)methanol
4-bromo-2-nitrobenzaldehyde
Conditions | Yield |
---|---|
With manganese(IV) oxide In dichloromethane at 20℃; for 12h; | 78% |
4-bromo-2-nitrobenzaldehyde
Conditions | Yield |
---|---|
With sodium periodate In tetrahydrofuran; water at 0 - 25℃; for 18h; | 74% |
With sodium periodate In tetrahydrofuran; water for 2h; | 9.58 g |
With sodium periodate In tetrahydrofuran; water at 0℃; for 15h; |
1,4-dibromo-2-nitrobenzene
N,N-dimethyl-formamide
4-bromo-2-nitrobenzaldehyde
Conditions | Yield |
---|---|
Stage #1: 1,4-dibromo-2-nitrobenzene With phenyllithium In tetrahydrofuran Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78 - 0℃; Stage #3: With sulfuric acid In water at 0℃; | 71% |
With phenyllithium 1) THF, benzene, ether, 25 min, -105 deg C, 2) 0.5 h, -78 deg C; Yield given. Multistep reaction; | |
Stage #1: 1,4-dibromo-2-nitrobenzene With phenyllithium In tetrahydrofuran at -105℃; for 0.5h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -105 - -20℃; |
4-bromo-1-(bromomethyl)-2-nitrobenzene
4-bromo-2-nitrobenzaldehyde
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; dimethyl sulfoxide at 80℃; for 12h; | 68% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide; sulfuric acid at 25℃; for 3h; | 60% |
4-bromo-2-nitrotoluene
4-bromo-2-nitrobenzaldehyde
Conditions | Yield |
---|---|
Stage #1: 4-bromo-2-nitrotoluene With chromium(VI) oxide; sulfuric acid; acetic anhydride at 0 - 10℃; for 1h; Stage #2: With sodium carbonate In water Stage #3: With hydrogenchloride; water In ethanol for 0.75h; | 45% |
Multi-step reaction with 2 steps 1: dimethylformamide / 18 h / 120 °C 2: NaIO4 / tetrahydrofuran; H2O / 2 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: pyrrolidine / Heating 2: sodium periodate / H2O; dimethylformamide / 20 °C View Scheme |
2-nitro-benzaldehyde
A
4-bromo-2-nitrobenzaldehyde
B
4,5-dibromo-2-nitrobenzaldehyde
C
5-bromo-2-nitrobenzaldehyde
D
2-bromo-6-nitrobenzaldehyde
Conditions | Yield |
---|---|
With N-Bromosuccinimide; sulfuric acid at 25℃; for 3h; | A 19% B 1% C 12% D 24% |
2-nitro-benzaldehyde
A
4-bromo-2-nitrobenzaldehyde
B
4,5-dibromo-2-nitrobenzaldehyde
C
5-bromo-2-nitrobenzaldehyde
D
2-bromo-6-nitrobenzaldehyde
E
3,4-dibromo-2-nitrobenzaldehyde
Conditions | Yield |
---|---|
With N-Bromosuccinimide; sulfuric acid at 25℃; for 3h; | A 21% B 1% C 9% D 20% E 5% |
2-nitro-benzaldehyde
A
3-bromo-2-nitrobenzaldehyde
B
4-bromo-2-nitrobenzaldehyde
C
4,5-dibromo-2-nitrobenzaldehyde
D
5-bromo-2-nitrobenzaldehyde
E
2-bromo-6-nitrobenzaldehyde
F
3,4-dibromo-2-nitrobenzaldehyde
Conditions | Yield |
---|---|
With N-Bromosuccinimide; sulfuric acid at 25℃; for 3h; | A 8% B 20% C 9% D 8% E 14% F 12% G 13% |
2-nitro-benzaldehyde
A
4-bromo-2-nitrobenzaldehyde
B
4,5-dibromo-2-nitrobenzaldehyde
C
2-bromo-6-nitrobenzaldehyde
D
3,4-dibromo-2-nitrobenzaldehyde
Conditions | Yield |
---|---|
With N-Bromosuccinimide; sulfuric acid at 60℃; for 3h; | A 10% B 2% C 8% D 9% |
4-bromo-2-nitrobenzaldehyde
Conditions | Yield |
---|---|
With hydrogenchloride | |
With iron (III)-ammonium sulfate; sulfuric acid |
4-amino-2-nitro-benzaldehyde-oxime
4-bromo-2-nitrobenzaldehyde
Conditions | Yield |
---|---|
With water; hydrogen bromide; iron(III) chloride | |
With iron(III) sulfate; hydrogen bromide | |
With hydrogen bromide Diazotization.Versetzen mit Kupferpaste und Destillieren mit Wasserdampf oder Verkochen der Diazoniumsalzloesung mit Kupferbromuer; |
4-amino-2-nitro-benzaldehyde-oxime
hydrogen bromide
4-bromo-2-nitrobenzaldehyde
β-dimethylamino-2-nitrostyrene
4-bromo-2-nitrobenzaldehyde
Conditions | Yield |
---|---|
With sodium periodate In water; N,N-dimethyl-formamide at 20℃; |
(E)-2-(4-bromo-2-nitrophenyl)-N,N-dimethylethyleneamine
4-bromo-2-nitrobenzaldehyde
Conditions | Yield |
---|---|
With sodium periodate In tetrahydrofuran; water at 20℃; for 2h; | |
With sodium periodate In tetrahydrofuran; water pH=7.2; Aqueous phosphate buffer; |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: 64 percent / H2SO4; HNO3 / -5 °C 2.1: HBr; NaNO2 / H2O / 0 °C 2.2: 58 percent / CuBr; HBr / H2O 3.1: 65 percent / H2SO4; CrO3 / acetic acid; H2O / 9 h / 5 - 10 °C 4.1: 93 percent / H2SO4 / ethanol / 1.5 h / Heating View Scheme |
4-bromo-2-nitrobenzaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: HBr; NaNO2 / H2O / 0 °C 1.2: 58 percent / CuBr; HBr / H2O 2.1: 65 percent / H2SO4; CrO3 / acetic acid; H2O / 9 h / 5 - 10 °C 3.1: 93 percent / H2SO4 / ethanol / 1.5 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: aqueous H2SO4; aqueous NaNO2-solution; CuBr 2: ethanolic sodium ethylate solution 3: concentrated aqueous hydrochloric acid View Scheme |
Conditions | Yield |
---|---|
With phenyllithium In tetrahydrofuran; N,N-dimethyl-formamide at -100℃; for 1.5h; | 3.53 g |
4-bromo-2-nitrobenzaldoxime
4-bromo-2-nitrobenzaldehyde
Conditions | Yield |
---|---|
With ammonium iron(III) sulfate dodecahydrate In water for 1.5h; Reflux; |
4-bromo-2-nitrobenzoic acid
4-bromo-2-nitrobenzaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: borane / tetrahydrofuran / 48 h / 0 - 20 °C 1.2: 0 °C 2.1: manganese(IV) oxide / dichloromethane / 12 h / 20 °C View Scheme |
3-(triphenylphosphoranyliden)dihydro-2(3H)-furanone
4-bromo-2-nitrobenzaldehyde
Conditions | Yield |
---|---|
In toluene for 2h; Heating; | 100% |
4-bromo-2-nitrobenzaldehyde
2-(tri-n-butylstannyl)thiazole
2-nitro-4-(thiazol-2-yl)benzaldehyde
Conditions | Yield |
---|---|
tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 80℃; | 100% |
Conditions | Yield |
---|---|
With ammonium chloride In ethanol at 20℃; | 98% |
Conditions | Yield |
---|---|
With morpholine In water at 20℃; for 1h; | 97.3% |
4-bromo-2-nitrobenzaldehyde
(4-bromo-2-nitrophenyl)methanol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol; water at 0℃; for 17.5h; | 97% |
With sodium tetrahydroborate In tetrahydrofuran at 0℃; for 0.25h; | 80% |
3-aminoazetidine-1-carboxylic acid tert-butyl ester
4-bromo-2-nitrobenzaldehyde
Conditions | Yield |
---|---|
With methanol; sodium cyanoborohydride; acetic acid at 50℃; | 95% |
Stage #1: 3-aminoazetidine-1-carboxylic acid tert-butyl ester; 4-bromo-2-nitrobenzaldehyde With acetic acid In methanol at 20℃; for 0.166667h; Stage #2: With sodium cyanoborohydride In methanol at 50℃; for 16h; | 95% |
5-hydroxypentylamine
4-bromo-2-nitrobenzaldehyde
1-pentanol, 5-[[(4-bromo-2-nitrophenyl)methyl]amino]-
Conditions | Yield |
---|---|
Stage #1: 5-hydroxypentylamine; 4-bromo-2-nitrobenzaldehyde With titanium(IV) isopropylate In ethanol at 20 - 50℃; for 1.5h; Stage #2: With sodium tetrahydroborate In ethanol at 20℃; | 93% |
Stage #1: 5-hydroxypentylamine; 4-bromo-2-nitrobenzaldehyde With titanium(IV) isopropylate In ethanol at 20 - 50℃; for 1.5h; Stage #2: With sodium tetrahydroborate In ethanol at 20℃; | 93% |
Stage #1: 5-hydroxypentylamine; 4-bromo-2-nitrobenzaldehyde; titanium(IV) isopropylate In ethanol at 20 - 50℃; for 1.5h; Stage #2: With sodium tetrahydroborate In ethanol at 20℃; Stage #3: With water In ethanol for 0.333333h; | 93% |
Conditions | Yield |
---|---|
With 4 A molecular sieve In 1,2-dichloro-benzene at 110 - 120℃; for 24h; | 92% |
ethyl 3,3-diethoxypropanoate
4-bromo-2-nitrobenzaldehyde
7-bromoquinoline-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With tin(II) chloride dihdyrate In ethanol at 90℃; for 12h; | 92% |
With tin(II) chloride dihdyrate In ethanol at 90℃; for 4h; reductive Friedlander reaction; Inert atmosphere; | 85% |
With tin(II) chloride dihdyrate In ethanol at 90℃; for 4h; | 21.5% |
With tin(II) chloride dihdyrate In ethanol at 90℃; for 4h; |
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 3h; | 92% |
4-bromo-2-nitrobenzaldehyde
4-chlorophenylacetic acid sodium salt
(2E)-3-(4-bromo-2-nitrophenyl)-2-(4-chlorophenyl)prop-2-enoic acid
Conditions | Yield |
---|---|
With acetic anhydride Perkin condensation; Heating; | 91% |
4-bromo-2-nitrobenzaldehyde
2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In toluene Suzuki Coupling; | 91% |
[4-(pyrrolidin-1-ylcarbonyl)phenyl]boronic acid
4-bromo-2-nitrobenzaldehyde
3-nitro-4'-(pyrrolidine-1-carbonyl)biphenyl-4-carbaldehyde
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 100℃; for 18h; Product distribution / selectivity; | 90% |
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 100℃; for 18h; Product distribution / selectivity; | 90% |
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 100℃; for 18h; |
4-bromo-2-nitrobenzaldehyde
methyl (triphenylphosphoranylidene)acetate
(Z)-methyl 2-bromo-3-(4-bromo-2-nitrophenyl)acrylate
Conditions | Yield |
---|---|
Stage #1: methyl (triphenylphosphoranylidene)acetate With dimethylbromosulphonium bromide In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: 4-bromo-2-nitrobenzaldehyde With triethylamine In dichloromethane at -78 - 20℃; Inert atmosphere; | 90% |
4-bromo-2-nitrobenzaldehyde
C35H28NO3PS
Conditions | Yield |
---|---|
In chloroform for 10h; Wittig Olefination; Inert atmosphere; Reflux; | 90% |
Conditions | Yield |
---|---|
With ammonium chloride; zinc In neat (no solvent) for 0.075h; Microwave irradiation; | 90% |
4-bromo-2-nitrobenzaldehyde
6-amino-1H-indazole
1,3-dimethyl-5-pyrazolone
Conditions | Yield |
---|---|
In ethanol Reflux; | 89% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In toluene Stille Cross Coupling; | 89% |
4-bromo-2-nitrobenzaldehyde
ethyl 3-cyano-2-(triphenylphosphoranylidene)propanoate
2-[1-(4-bromo-2-nitrophenyl)-(E)-methylidene]-3-cyanopropionic acid ethyl ester
Conditions | Yield |
---|---|
In toluene at 20 - 25℃; Product distribution / selectivity; Wittig Reaction; | 87% |
In toluene at 110℃; for 3h; | 83% |
In toluene at 25℃; for 18h; | 78% |
In toluene at 25℃; for 18h; | 78% |
In toluene for 2.5h; Reflux; |
4-bromo-2-nitrobenzaldehyde
methyl trans-4-amino-cyclohexanecarboxylate
Conditions | Yield |
---|---|
Stage #1: 4-bromo-2-nitrobenzaldehyde; methyl trans-4-amino-cyclohexanecarboxylate In isopropyl alcohol at 80℃; for 4h; Inert atmosphere; Stage #2: With tributylphosphine In isopropyl alcohol at 80℃; for 16h; Inert atmosphere; | 87% |
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 3h; | 85% |
4-bromo-2-nitrobenzaldehyde
6-amino-1H-indazole
3-phenyl-4H-isoxazol-5-one
Conditions | Yield |
---|---|
In ethanol at 80℃; for 13h; | 84% |
4-bromo-2-nitrobenzaldehyde
6-amino-1H-indazole
3-(4-methoxyphenyl)isoxazol-5(4H)-one
Conditions | Yield |
---|---|
In ethanol at 80℃; for 10h; | 84% |
4-bromo-2-nitrobenzaldehyde
Conditions | Yield |
---|---|
With stannous chloride hydrate In methanol; ethyl acetate at 20℃; for 24h; | 84% |
With tin(ll) chloride In methanol; ethyl acetate at 20℃; | 64% |
With tin(II) chloride dihdyrate In methanol; ethyl acetate at 20℃; for 24h; Inert atmosphere; |
4-bromo-2-nitrobenzaldehyde
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
3-nitro-biphenyl-4-carbaldehyde
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In toluene Suzuki Coupling; | 84% |
Conditions | Yield |
---|---|
With pentafluorophenyl(2,4,6-trimethylphenyl)iodonium tosylate at 20℃; for 24h; Mannich Aminomethylation; | 83% |
4-bromo-2-nitrobenzaldehyde
(Benzoylmethylene)triphenylphosphorane
Conditions | Yield |
---|---|
In acetonitrile | 83% |
In toluene at 90℃; Inert atmosphere; |
2-(4-chlorophenyl)-3-nitro-2H-chromene
4-bromo-2-nitrobenzaldehyde
Conditions | Yield |
---|---|
With iron; acetic acid at 100℃; for 2h; | A 83% B 8% |
Conditions | Yield |
---|---|
With iron pentacarbonyl In tetrahydrofuran at 120℃; for 6h; Schlenk technique; Inert atmosphere; | 83% |
Molecule structure of 4-Bromo-2-nitrobenzaldehyde (CAS NO.5551-12-2) :
IUPAC Name: 4-bromo-2-nitrobenzaldehyde
Molecular Weight: 230.01556 g/mol
Molecular Formula: C7H4BrNO3
Density: 1.781 g/cm3
Boiling Point: 334.4 °C at 760 mmHg
Flash Point: 156.1 °C
Molar Volume: 129.1 cm3
Polarizability: 18.72*10-24 cm3
Surface Tension: 59.2 dyne/cm
Enthalpy of Vaporization: 57.74 kJ/mol
Vapour Pressure: 0.000128 mmHg at 25 °C
XLogP3: 2
H-Bond Acceptor: 3
Rotatable Bond Count: 1
Exact Mass: 228.937456
MonoIsotopic Mass: 228.937456
Topological Polar Surface Area: 60.2
Heavy Atom Count: 12
Complexity: 192
Canonical SMILES: C1=CC(=C(C=C1Br)[N+](=O)[O-])C=O
InChI: InChI=1S/C7H4BrNO3/c8-6-2-1-5(4-10)7(3-6)9(11)12/h1-4H
InChIKey: GSXUXSXBEUJRAJ-UHFFFAOYSA-N
Product Categories of 4-Bromo-2-nitrobenzaldehyde (CAS NO.5551-12-2) : Aromatic Aldehydes & Derivatives (substituted); Heterocyclic Compounds
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