5551-12-2

Basic information

• Product Name: 4-Bromo-2-nitrobenzaldehyde
• Synonyms: 4-BROMO-2-NITROBENZALDEHYDE;4-BroMo-2-nitrobenzaldehyde, 95+%
• CAS NO: 5551-12-2
• Molecular Formula: C₇H₄BrNO₃
• Molecular Weight: 230.02
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Heterocyclic Compounds
• Mol File: 5551-12-2.mol
• Article Data: 21

Chemical Properties

• Melting Point: 95.0 to 99.0 °C
• Boiling Point: 334.4°Cat760mmHg
• Flash Point: 156.1°C
• Appearance: /
• Density: 1.781g/cm³
• Vapor Pressure: 0.000128mmHg at 25°C
• Refractive Index: 1.652
• Solubility: soluble in Methanol
• CAS DataBase Reference: 4-Bromo-2-nitrobenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-2-nitrobenzaldehyde(5551-12-2)
• EPA Substance Registry System: 4-Bromo-2-nitrobenzaldehyde(5551-12-2)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-36/37/38-43-50
• Safety Statements: 26-36/37-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 5551-12-2(Hazardous Substances Data)

Usage

Description

4-Bromo-2-nitrobenzaldehyde is an organic compound with the molecular formula C7H4BrNO3. It is a derivative of benzaldehyde, featuring a bromine atom at the 4th position and a nitro group at the 2nd position. 4-Bromo-2-nitrobenzaldehyde is known for its distinct chemical properties and reactivity, making it a versatile building block in various chemical syntheses.

Uses

Used in Chemical Synthesis:
4-Bromo-2-nitrobenzaldehyde is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for further functionalization and modification, making it a valuable starting material for the production of a wide range of chemicals.
Used in the Synthesis of Tyrian Purple:
4-Bromo-2-nitrobenzaldehyde is utilized in the synthesis of Tyrian Purple, an ancient and highly valued dye. It serves as a teaching material, demonstrating the process from o-Nitrotoluene via 4-Bromo-2-nitrotoluene and 4-Bromo-2-nitrobenzylidene diacetate. This application highlights the compound's role in historical and educational contexts.
Used in the Synthesis of Heterocyclic Compounds as HDAC3 Inhibitors:
4-Bromo-2-nitrobenzaldehyde is also used as a starting material in the synthesis of heterocyclic compounds, specifically as inhibitors of Histone Deacetylase 3 (HDAC3). These inhibitors play a crucial role in the regulation of gene expression and have potential applications in the treatment of various diseases, including cancer.

InChI:InChI=1/C7H4BrNO3/c8-6-2-1-5(4-10)7(3-6)9(11)12/h1-4H

Synthetic route

4-bromo-2-nitrobenzylidene diethanoate (135308-80-4) → 4-bromo-2-nitrobenzaldehyde (5551-12-2)

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 (22996-19-6) → 4-bromo-2-nitrobenzaldehyde (5551-12-2)

Conditions	Yield
With manganese(IV) oxide In dichloromethane at 20℃; for 12h;	78%

1-[(E)-2-(4-bromo-2-nitrophenyl)vinyl]pyrrolidine → 4-bromo-2-nitrobenzaldehyde (5551-12-2)

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 (3460-18-2) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 4-bromo-2-nitrobenzaldehyde (5551-12-2)

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 (82420-34-6) → 4-bromo-2-nitrobenzaldehyde (5551-12-2)

Conditions	Yield
With sodium hydrogencarbonate; dimethyl sulfoxide at 80℃; for 12h;	68%

2-nitro-benzaldehyde (552-89-6) → 4-bromo-2-nitrobenzaldehyde (5551-12-2)

Conditions	Yield
With N-Bromosuccinimide; sulfuric acid at 25℃; for 3h;	60%

4-bromo-2-nitrotoluene (60956-26-5) → 4-bromo-2-nitrobenzaldehyde (5551-12-2)

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 (552-89-6) → 4-bromo-2-nitrobenzaldehyde (5551-12-2) + 4,5-dibromo-2-nitrobenzaldehyde (56990-05-7) + 5-bromo-2-nitrobenzaldehyde (20357-20-4) + 2-bromo-6-nitrobenzaldehyde (20357-21-5)

Conditions	Yield
With N-Bromosuccinimide; sulfuric acid at 25℃; for 3h;	A 19% B 1% C 12% D 24%

2-nitro-benzaldehyde (552-89-6) → 4-bromo-2-nitrobenzaldehyde (5551-12-2) + 4,5-dibromo-2-nitrobenzaldehyde (56990-05-7) + 5-bromo-2-nitrobenzaldehyde (20357-20-4) + 2-bromo-6-nitrobenzaldehyde (20357-21-5) + 3,4-dibromo-2-nitrobenzaldehyde (1559060-83-1)

Conditions	Yield
With N-Bromosuccinimide; sulfuric acid at 25℃; for 3h;	A 21% B 1% C 9% D 20% E 5%

2-nitro-benzaldehyde (552-89-6) → 3-bromo-2-nitrobenzaldehyde (882772-99-8) + 4-bromo-2-nitrobenzaldehyde (5551-12-2) + 4,5-dibromo-2-nitrobenzaldehyde (56990-05-7) + 5-bromo-2-nitrobenzaldehyde (20357-20-4) + 2-bromo-6-nitrobenzaldehyde (20357-21-5) + 3,4-dibromo-2-nitrobenzaldehyde (1559060-83-1) + 3,6-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 (552-89-6) → 4-bromo-2-nitrobenzaldehyde (5551-12-2) + 4,5-dibromo-2-nitrobenzaldehyde (56990-05-7) + 2-bromo-6-nitrobenzaldehyde (20357-21-5) + 3,4-dibromo-2-nitrobenzaldehyde (1559060-83-1)

Conditions	Yield
With N-Bromosuccinimide; sulfuric acid at 60℃; for 3h;	A 10% B 2% C 8% D 9%

4-bromo-2-nitro-benzaldehyde-oxime → 4-bromo-2-nitrobenzaldehyde (5551-12-2)

Conditions	Yield
With hydrogenchloride
With iron (III)-ammonium sulfate; sulfuric acid

4-amino-2-nitro-benzaldehyde-oxime (959089-98-6) → 4-bromo-2-nitrobenzaldehyde (5551-12-2)

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 (959089-98-6) + hydrogen bromide (10035-10-6, 12258-64-9) + ferrisulfate → 4-bromo-2-nitrobenzaldehyde (5551-12-2)

β-dimethylamino-2-nitrostyrene (78508-22-2) → 4-bromo-2-nitrobenzaldehyde (5551-12-2)

Conditions	Yield
With sodium periodate In water; N,N-dimethyl-formamide at 20℃;

(E)-2-(4-bromo-2-nitrophenyl)-N,N-dimethylethyleneamine (99474-21-2) → 4-bromo-2-nitrobenzaldehyde (5551-12-2)

Conditions	Yield
With sodium periodate In tetrahydrofuran; water at 20℃; for 2h;
With sodium periodate In tetrahydrofuran; water pH=7.2; Aqueous phosphate buffer;

p-toluidine (106-49-0) + C7H9N+H3PO4 → 4-bromo-2-nitrobenzaldehyde (5551-12-2)

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

3-nitro-4-methylphenylammonium hydrogensulfate → 4-bromo-2-nitrobenzaldehyde (5551-12-2)

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

4-Methyl-3-nitroanilin (119-32-4) → 4-bromo-2-nitrobenzaldehyde (5551-12-2)

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

1,4-dibromo-2-nitrobenzene (3460-18-2) → 4-bromo-2-nitrobenzaldehyde (5551-12-2)

Conditions	Yield
With phenyllithium In tetrahydrofuran; N,N-dimethyl-formamide at -100℃; for 1.5h;	3.53 g

4-bromo-2-nitrobenzaldoxime (408526-96-5) → 4-bromo-2-nitrobenzaldehyde (5551-12-2)

Conditions	Yield
With ammonium iron(III) sulfate dodecahydrate In water for 1.5h; Reflux;

4-bromo-2-nitrobenzoic acid (99277-71-1) → 4-bromo-2-nitrobenzaldehyde (5551-12-2)

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 (34932-07-5) + 4-bromo-2-nitrobenzaldehyde (5551-12-2) → 3-[1-(4-Bromo-2-nitro-phenyl)-meth-(E)-ylidene]-dihydro-furan-2-one

Conditions	Yield
In toluene for 2h; Heating;	100%

4-bromo-2-nitrobenzaldehyde (5551-12-2) + 2-(tri-n-butylstannyl)thiazole (121359-48-6) → 2-nitro-4-(thiazol-2-yl)benzaldehyde (942614-28-0)

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 80℃;	100%

4-bromo-2-nitrobenzaldehyde (5551-12-2) + 2-amino-1-benzylamine (4403-69-4) → 2-(4-bromo-2-nitrophenyl)-1,2,3,4-tetrahydroquinazoline

Conditions	Yield
With ammonium chloride In ethanol at 20℃;	98%

4-bromo-2-nitrobenzaldehyde (5551-12-2) + ethyl 2-cyanoacetate (105-56-6) → ethyl (2Z)-3-(4-bromo-2-nitrophenyl)-2-cyanoprop-2-enoate

Conditions	Yield
With morpholine In water at 20℃; for 1h;	97.3%

4-bromo-2-nitrobenzaldehyde (5551-12-2) → (4-bromo-2-nitrophenyl)methanol (22996-19-6)

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 (193269-78-2) + 4-bromo-2-nitrobenzaldehyde (5551-12-2) → tert-butyl 3-((4-bromo-2-nitrobenzyl)amino)azetidine-1-carboxylate

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 (2508-29-4) + 4-bromo-2-nitrobenzaldehyde (5551-12-2) → 1-pentanol, 5-[[(4-bromo-2-nitrophenyl)methyl]amino]- (807639-63-0)

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%

4-bromo-2-nitrobenzaldehyde (5551-12-2) + 2,2-diethoxy-ethanamine (645-36-3) → (4-bromo-2-nitrobenzalamino)acetaldehyde diethyl acetal

Conditions	Yield
With 4 A molecular sieve In 1,2-dichloro-benzene at 110 - 120℃; for 24h;	92%

ethyl 3,3-diethoxypropanoate (10601-80-6) + 4-bromo-2-nitrobenzaldehyde (5551-12-2) → 7-bromoquinoline-3-carboxylic acid ethyl ester (1226762-74-8)

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;

morpholine (110-91-8) + 4-bromo-2-nitrobenzaldehyde (5551-12-2) → 4-(4-bromo-2-nitrobenzyl)morpholine

Conditions	Yield
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 3h;	92%

4-bromo-2-nitrobenzaldehyde (5551-12-2) + 4-chlorophenylacetic acid sodium salt (25307-03-3) → (2E)-3-(4-bromo-2-nitrophenyl)-2-(4-chlorophenyl)prop-2-enoic acid (929606-23-5)

Conditions	Yield
With acetic anhydride Perkin condensation; Heating;	91%

4-bromo-2-nitrobenzaldehyde (5551-12-2) + 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophene (376584-76-8) → C15H9NO3S

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In toluene Suzuki Coupling;	91%

[4-(pyrrolidin-1-ylcarbonyl)phenyl]boronic acid (389621-81-2) + 4-bromo-2-nitrobenzaldehyde (5551-12-2) → 3-nitro-4'-(pyrrolidine-1-carbonyl)biphenyl-4-carbaldehyde (1268163-44-5)

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 (5551-12-2) + methyl (triphenylphosphoranylidene)acetate (21204-67-1) → (Z)-methyl 2-bromo-3-(4-bromo-2-nitrophenyl)acrylate (1586740-47-7)

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 (5551-12-2) + C35H28NO3PS (1445973-83-0) → (E)-1-(2-(4-bromo-2-nitrostyryl)-1-phenylsulfonyl-1H-indol-3-yl)ethanone

Conditions	Yield
In chloroform for 10h; Wittig Olefination; Inert atmosphere; Reflux;	90%

4-bromo-2-nitrobenzaldehyde (5551-12-2) + methyl 2-cyanoacetate (105-34-0) → methyl 2-amino-7-bromoquinoline-3-carboxylate

Conditions	Yield
With ammonium chloride; zinc In neat (no solvent) for 0.075h; Microwave irradiation;	90%

4-bromo-2-nitrobenzaldehyde (5551-12-2) + 6-amino-1H-indazole (6967-12-0) + 1,3-dimethyl-5-pyrazolone (2749-59-9) → 7',9'-bis(4-bromo-2-nitrophenyl)-1,3-dimethyl-1',6',7',9'-tetrahydrospiro[pyrazole-4,8'-pyrazolo[3,4-f]quinolin]-5(1H)-one

Conditions	Yield
In ethanol Reflux;	89%

4-bromo-2-nitrobenzaldehyde (5551-12-2) + 2-(tri-n-butyltin)benzothiazole (105445-58-7) → C14H8N2O3S

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In toluene Stille Cross Coupling;	89%

4-bromo-2-nitrobenzaldehyde (5551-12-2) + ethyl 3-cyano-2-(triphenylphosphoranylidene)propanoate (174362-09-5) → 2-[1-(4-bromo-2-nitrophenyl)-(E)-methylidene]-3-cyanopropionic acid ethyl ester (926927-55-1)

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 (5551-12-2) + methyl trans-4-amino-cyclohexanecarboxylate (62456-15-9) → methyl (1r,4r)-4-(6-bromo-2H-indazol-2-yl)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%

pyrrolidine (123-75-1) + 4-bromo-2-nitrobenzaldehyde (5551-12-2) → 1-(4-bromo-2-nitrobenzyl)pyrrolidine

Conditions	Yield
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 3h;	85%

4-bromo-2-nitrobenzaldehyde (5551-12-2) + 6-amino-1H-indazole (6967-12-0) + 3-phenyl-4H-isoxazol-5-one (1076-59-1) → 7′,9′-bis(4-bromo-2-nitrophenyl)-3-phenyl-1′,6′,7′,9′-tetrahydro-5H-spiro[isoxazole-4,8′-pyrazolo[3,4-f]quinolin]-5-one

Conditions	Yield
In ethanol at 80℃; for 13h;	84%

4-bromo-2-nitrobenzaldehyde (5551-12-2) + 6-amino-1H-indazole (6967-12-0) + 3-(4-methoxyphenyl)isoxazol-5(4H)-one (31709-47-4) → 7′,9′-bis(4-bromo-2-nitrophenyl)-3-(4-methoxyphenyl)-1′,6′,7′,9′-tetrahydro-5H-spiro[isoxazole-4,8′-pyrazolo[3,4-f]quinolin]-5-one

Conditions	Yield
In ethanol at 80℃; for 10h;	84%

4-bromo-2-nitrobenzaldehyde (5551-12-2) → 6-bromo benzo[c]isoxazole

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 (5551-12-2) + 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6) → 3-nitro-biphenyl-4-carbaldehyde (515878-88-3)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In toluene Suzuki Coupling;	84%

4-bromo-2-nitrobenzaldehyde (5551-12-2) + aniline (62-53-3) + acetophenone (98-86-2) → C21H17BrN2O3

Conditions	Yield
With pentafluorophenyl(2,4,6-trimethylphenyl)iodonium tosylate at 20℃; for 24h; Mannich Aminomethylation;	83%

4-bromo-2-nitrobenzaldehyde (5551-12-2) + (Benzoylmethylene)triphenylphosphorane (20913-05-7) → (E)-3-(4-bromo-2-nitrophenyl)-1-phenylprop-2-en-1-one

Conditions	Yield
In acetonitrile	83%
In toluene at 90℃; Inert atmosphere;

2-(4-chlorophenyl)-3-nitro-2H-chromene (108026-41-1, 57544-16-8) + 4-bromo-2-nitrobenzaldehyde (5551-12-2) → 9-bromo-6-(4-chlorophenyl)-6H-chromeno[3,4-b]quinolin-6-ol + 9-bromo-6-(4-chlorophenyl)-6H-chromeno[3,4-b]quinoline

Conditions	Yield
With iron; acetic acid at 100℃; for 2h;	A 83% B 8%

pyrrolidine (123-75-1) + 4-bromo-2-nitrobenzaldehyde (5551-12-2) → 5-bromo-2-(pyrrolidin-1-ylmethyl)aniline

Conditions	Yield
With iron pentacarbonyl In tetrahydrofuran at 120℃; for 6h; Schlenk technique; Inert atmosphere;	83%

Upstream product

• 959089-98-6 4-amino-2-nitro-benzaldehyde-oxime 
• 10035-10-6 hydrogen bromide 
• 119-32-4 4-Methyl-3-nitroanilin 
• 3460-18-2 1,4-dibromo-2-nitrobenzene 
• 99277-71-1 4-bromo-2-nitrobenzoic acid 
• 552-89-6 2-nitro-benzaldehyde 
• 408526-96-5 4-bromo-2-nitrobenzaldoxime 
• 106-49-0 p-toluidine 
• 60956-26-5 4-bromo-2-nitrotoluene 
• 22996-19-6 (4-bromo-2-nitrophenyl)methanol 
• 99474-21-2 (E)-2-(4-bromo-2-nitrophenyl)-N,N-dimethylethyleneamine 
• 78508-22-2 β-dimethylamino-2-nitrostyrene 
• 82420-34-6 4-bromo-1-(bromomethyl)-2-nitrobenzene 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 6824-80-2 4-bromo-2-nitro-benzaldehyde-semicarbazone 
• 59278-65-8 2-amino-4-bromobenzaldehyde 
• 70557-29-8 4-(4-bromo-2-nitro-phenyl)-4-hydroxy-butan-2-one 
• 19201-53-7 6,6′?di?bromo?indigo 
• 38224-27-0 N-<4-Brom-2-nitro-benzyliden>-4-brom-anilin 
• 19201-53-7 tyrian purple 
• 929606-22-4 (2E)-3-(4-bromo-2-nitrophenyl)-2-(4-bromophenyl)prop-2-enoic acid 
• 780766-43-0 (4-bromo-2-nitrophenyl)(2-dimethylaminomethylphenyl)methanol 
• 929606-23-5 (2E)-3-(4-bromo-2-nitrophenyl)-2-(4-chlorophenyl)prop-2-enoic acid 
• 904328-01-4 5,5'-((4-bromo-2-nitrophenyl)methylene)bis(2-methylfuran) 
• 585533-29-5 6-bromo-2-(4-chloro-phenyl)-benzo[b]thiophene 
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• 942614-31-5 2-(2-nitro-4-(thiazol-2-yl)phenyl)-1H-benzimidazole 
• 942614-35-9 2-(1H-benzimidazol-2-yl)-5-(thiazol-2-yl)phenylamine 

Relevant articles and documents

Novel functionalized indigo derivatives for organic electronics

A series of nine novel indigo derivatives, including diiodoindigo, octahalogenated indigoids and compounds with extended π-conjugated system, were synthesized, characterized and investigated as semiconductor materials in organic field-effect transistors (OFETs). Among them, 6,6′-diiodoindigo demonstrated the ambipolar behavior with balanced p-type and n-type mobilities. The complete substitution of hydrogens at the indigo core with halogen atoms led to low electron mobilities in OFETs. An extension of the conjugated system through the introduction of small aromatic substituents (thiophene and phenyl) resulted in predominant p-type behavior. Fusion of aromatic rings resulted in z-shaped dibenzoindigo, which showed poor charge transport properties due to the non-optimal arrangement of molecules along each other in the crystal lattice. The acquired data fulfilled the previously reported model based on the relationship between the chemical nature of substituents and their positions at the indigo core, optoelectronic properties of materials and their performance in OFETs. The results of this study will be useful for rational design of a new generation of the indigo-based semiconductors for biocompatible organic electronics.

BENZAZEPINE SULFONAMIDE COMPOUNDS

This invention relates to novel benzazepine sulfonamide compounds of the formula (I), wherein R4 or R5 is -SO2-NR7R8 and R1 to R8 and Y are as defined in the description and in the claims, as well as pharmaceutically acceptable salts thereof. These compounds are TLR agonists and may therefore be useful as medicaments for the treatment of diseases such as cancer, autoimmune diseases, inflammation, sepsis, allergy, asthma, graft rejection, graft-versus-host disease, immunodeficiencies, and infectious diseases.

SUBSTITUTED BENZOAZEPINES AS TOLL-LIKE RECEPTOR MODULATORS

Provided are compositions and methods useful for modulation of signaling through the Toll-like receptors TLR7 and/or TLR8. The compositions and methods have use in treating or preventing disease, including cancer, autoimmune disease, fibrotic disease, cardiovascular disease, infectious disease, inflammatory disorder, graft rejection, or graft-versus-host disease.