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5551-12-2 Usage

Uses

4-Bromo-2-nitrobenzaldehyde is used along with in the synthesis of Tyrian Purple as a teaching material, from o-Nitrotoluene via 4-Bromo-2-nitrotoluene and 4-Bromo-2-nitrobenzylidene diacetate;Also, it is used as a starting material in the synthesis of heterocyclyl as HDAC3 inhibitors.

Check Digit Verification of cas no

The CAS Registry Mumber 5551-12-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,5,5 and 1 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 5551-12:
(6*5)+(5*5)+(4*5)+(3*1)+(2*1)+(1*2)=82
82 % 10 = 2
So 5551-12-2 is a valid CAS Registry Number.
InChI:InChI=1/C7H4BrNO3/c8-6-2-1-5(4-10)7(3-6)9(11)12/h1-4H

5551-12-2 Well-known Company Product Price

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  • Aldrich

  • (756628)  4-Bromo-2-nitrobenzaldehyde  97%

  • 5551-12-2

  • 756628-1G

  • 868.14CNY

  • Detail

5551-12-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Bromo-2-nitrobenzaldehyde

1.2 Other means of identification

Product number -
Other names 2-nitro-4-bromobenzaldehyde

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5551-12-2 SDS

5551-12-2Synthetic route

4-bromo-2-nitrobenzylidene diethanoate
135308-80-4

4-bromo-2-nitrobenzylidene diethanoate

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

Conditions
ConditionsYield
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-nitrophenyl)methanol

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

Conditions
ConditionsYield
With manganese(IV) oxide In dichloromethane at 20℃; for 12h;78%
1-[(E)-2-(4-bromo-2-nitrophenyl)vinyl]pyrrolidine

1-[(E)-2-(4-bromo-2-nitrophenyl)vinyl]pyrrolidine

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

Conditions
ConditionsYield
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

1,4-dibromo-2-nitrobenzene

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

Conditions
ConditionsYield
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-1-(bromomethyl)-2-nitrobenzene

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

Conditions
ConditionsYield
With sodium hydrogencarbonate; dimethyl sulfoxide at 80℃; for 12h;68%
2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

Conditions
ConditionsYield
With N-Bromosuccinimide; sulfuric acid at 25℃; for 3h;60%
4-bromo-2-nitrotoluene
60956-26-5

4-bromo-2-nitrotoluene

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

Conditions
ConditionsYield
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

2-nitro-benzaldehyde

A

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

B

4,5-dibromo-2-nitrobenzaldehyde
56990-05-7

4,5-dibromo-2-nitrobenzaldehyde

C

5-bromo-2-nitrobenzaldehyde
20357-20-4

5-bromo-2-nitrobenzaldehyde

D

2-bromo-6-nitrobenzaldehyde
20357-21-5

2-bromo-6-nitrobenzaldehyde

Conditions
ConditionsYield
With N-Bromosuccinimide; sulfuric acid at 25℃; for 3h;A 19%
B 1%
C 12%
D 24%
2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

A

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

B

4,5-dibromo-2-nitrobenzaldehyde
56990-05-7

4,5-dibromo-2-nitrobenzaldehyde

C

5-bromo-2-nitrobenzaldehyde
20357-20-4

5-bromo-2-nitrobenzaldehyde

D

2-bromo-6-nitrobenzaldehyde
20357-21-5

2-bromo-6-nitrobenzaldehyde

E

3,4-dibromo-2-nitrobenzaldehyde
1559060-83-1

3,4-dibromo-2-nitrobenzaldehyde

Conditions
ConditionsYield
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

2-nitro-benzaldehyde

A

3-bromo-2-nitrobenzaldehyde
882772-99-8

3-bromo-2-nitrobenzaldehyde

B

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

C

4,5-dibromo-2-nitrobenzaldehyde
56990-05-7

4,5-dibromo-2-nitrobenzaldehyde

D

5-bromo-2-nitrobenzaldehyde
20357-20-4

5-bromo-2-nitrobenzaldehyde

E

2-bromo-6-nitrobenzaldehyde
20357-21-5

2-bromo-6-nitrobenzaldehyde

F

3,4-dibromo-2-nitrobenzaldehyde
1559060-83-1

3,4-dibromo-2-nitrobenzaldehyde

G

3,6-dibromo-2-nitrobenzaldehyde

3,6-dibromo-2-nitrobenzaldehyde

Conditions
ConditionsYield
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

2-nitro-benzaldehyde

A

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

B

4,5-dibromo-2-nitrobenzaldehyde
56990-05-7

4,5-dibromo-2-nitrobenzaldehyde

C

2-bromo-6-nitrobenzaldehyde
20357-21-5

2-bromo-6-nitrobenzaldehyde

D

3,4-dibromo-2-nitrobenzaldehyde
1559060-83-1

3,4-dibromo-2-nitrobenzaldehyde

Conditions
ConditionsYield
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-nitro-benzaldehyde-oxime

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

Conditions
ConditionsYield
With hydrogenchloride
With iron (III)-ammonium sulfate; sulfuric acid
4-amino-2-nitro-benzaldehyde-oxime
959089-98-6

4-amino-2-nitro-benzaldehyde-oxime

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

Conditions
ConditionsYield
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

4-amino-2-nitro-benzaldehyde-oxime

hydrogen bromide
10035-10-6, 12258-64-9

hydrogen bromide

ferrisulfate

ferrisulfate

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

β-dimethylamino-2-nitrostyrene
78508-22-2

β-dimethylamino-2-nitrostyrene

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

Conditions
ConditionsYield
With sodium periodate In water; N,N-dimethyl-formamide at 20℃;
(E)-2-(4-bromo-2-nitrophenyl)-N,N-dimethylethyleneamine
99474-21-2

(E)-2-(4-bromo-2-nitrophenyl)-N,N-dimethylethyleneamine

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

Conditions
ConditionsYield
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

p-toluidine

C7H9N+H3PO4

C7H9N+H3PO4

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

Conditions
ConditionsYield
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

3-nitro-4-methylphenylammonium hydrogensulfate

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

Conditions
ConditionsYield
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-Methyl-3-nitroanilin

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

Conditions
ConditionsYield
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

1,4-dibromo-2-nitrobenzene

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

Conditions
ConditionsYield
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-nitrobenzaldoxime

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

Conditions
ConditionsYield
With ammonium iron(III) sulfate dodecahydrate In water for 1.5h; Reflux;
4-bromo-2-nitrobenzoic acid
99277-71-1

4-bromo-2-nitrobenzoic acid

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

Conditions
ConditionsYield
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

3-(triphenylphosphoranyliden)dihydro-2(3H)-furanone

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

3-[1-(4-Bromo-2-nitro-phenyl)-meth-(E)-ylidene]-dihydro-furan-2-one

3-[1-(4-Bromo-2-nitro-phenyl)-meth-(E)-ylidene]-dihydro-furan-2-one

Conditions
ConditionsYield
In toluene for 2h; Heating;100%
4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

2-(tri-n-butylstannyl)thiazole
121359-48-6

2-(tri-n-butylstannyl)thiazole

2-nitro-4-(thiazol-2-yl)benzaldehyde
942614-28-0

2-nitro-4-(thiazol-2-yl)benzaldehyde

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 80℃;100%
4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

2-amino-1-benzylamine
4403-69-4

2-amino-1-benzylamine

2-(4-bromo-2-nitrophenyl)-1,2,3,4-tetrahydroquinazoline

2-(4-bromo-2-nitrophenyl)-1,2,3,4-tetrahydroquinazoline

Conditions
ConditionsYield
With ammonium chloride In ethanol at 20℃;98%
4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl (2Z)-3-(4-bromo-2-nitrophenyl)-2-cyanoprop-2-enoate

ethyl (2Z)-3-(4-bromo-2-nitrophenyl)-2-cyanoprop-2-enoate

Conditions
ConditionsYield
With morpholine In water at 20℃; for 1h;97.3%
4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

(4-bromo-2-nitrophenyl)methanol
22996-19-6

(4-bromo-2-nitrophenyl)methanol

Conditions
ConditionsYield
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

3-aminoazetidine-1-carboxylic acid tert-butyl ester

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

tert-butyl 3-((4-bromo-2-nitrobenzyl)amino)azetidine-1-carboxylate

tert-butyl 3-((4-bromo-2-nitrobenzyl)amino)azetidine-1-carboxylate

Conditions
ConditionsYield
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

5-hydroxypentylamine

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

1-pentanol, 5-[[(4-bromo-2-nitrophenyl)methyl]amino]-
807639-63-0

1-pentanol, 5-[[(4-bromo-2-nitrophenyl)methyl]amino]-

Conditions
ConditionsYield
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

4-bromo-2-nitrobenzaldehyde

2,2-diethoxy-ethanamine
645-36-3

2,2-diethoxy-ethanamine

(4-bromo-2-nitrobenzalamino)acetaldehyde diethyl acetal

(4-bromo-2-nitrobenzalamino)acetaldehyde diethyl acetal

Conditions
ConditionsYield
With 4 A molecular sieve In 1,2-dichloro-benzene at 110 - 120℃; for 24h;92%
ethyl 3,3-diethoxypropanoate
10601-80-6

ethyl 3,3-diethoxypropanoate

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

7-bromoquinoline-3-carboxylic acid ethyl ester
1226762-74-8

7-bromoquinoline-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
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

morpholine

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

4-(4-bromo-2-nitrobenzyl)morpholine

4-(4-bromo-2-nitrobenzyl)morpholine

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 3h;92%
4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

4-chlorophenylacetic acid sodium salt
25307-03-3

4-chlorophenylacetic acid sodium salt

(2E)-3-(4-bromo-2-nitrophenyl)-2-(4-chlorophenyl)prop-2-enoic acid
929606-23-5

(2E)-3-(4-bromo-2-nitrophenyl)-2-(4-chlorophenyl)prop-2-enoic acid

Conditions
ConditionsYield
With acetic anhydride Perkin condensation; Heating;91%
4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophene
376584-76-8

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophene

C15H9NO3S

C15H9NO3S

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In toluene Suzuki Coupling;91%
[4-(pyrrolidin-1-ylcarbonyl)phenyl]boronic acid
389621-81-2

[4-(pyrrolidin-1-ylcarbonyl)phenyl]boronic acid

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

3-nitro-4'-(pyrrolidine-1-carbonyl)biphenyl-4-carbaldehyde
1268163-44-5

3-nitro-4'-(pyrrolidine-1-carbonyl)biphenyl-4-carbaldehyde

Conditions
ConditionsYield
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

4-bromo-2-nitrobenzaldehyde

methyl (triphenylphosphoranylidene)acetate
21204-67-1

methyl (triphenylphosphoranylidene)acetate

(Z)-methyl 2-bromo-3-(4-bromo-2-nitrophenyl)acrylate
1586740-47-7

(Z)-methyl 2-bromo-3-(4-bromo-2-nitrophenyl)acrylate

Conditions
ConditionsYield
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

4-bromo-2-nitrobenzaldehyde

C35H28NO3PS
1445973-83-0

C35H28NO3PS

(E)-1-(2-(4-bromo-2-nitrostyryl)-1-phenylsulfonyl-1H-indol-3-yl)ethanone

(E)-1-(2-(4-bromo-2-nitrostyryl)-1-phenylsulfonyl-1H-indol-3-yl)ethanone

Conditions
ConditionsYield
In chloroform for 10h; Wittig Olefination; Inert atmosphere; Reflux;90%
4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

methyl 2-cyanoacetate
105-34-0

methyl 2-cyanoacetate

methyl 2-amino-7-bromoquinoline-3-carboxylate

methyl 2-amino-7-bromoquinoline-3-carboxylate

Conditions
ConditionsYield
With ammonium chloride; zinc In neat (no solvent) for 0.075h; Microwave irradiation;90%
4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

6-amino-1H-indazole
6967-12-0

6-amino-1H-indazole

1,3-dimethyl-5-pyrazolone
2749-59-9

1,3-dimethyl-5-pyrazolone

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

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
ConditionsYield
In ethanol Reflux;89%
4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

2-(tri-n-butyltin)benzothiazole
105445-58-7

2-(tri-n-butyltin)benzothiazole

C14H8N2O3S

C14H8N2O3S

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In toluene Stille Cross Coupling;89%
4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

ethyl 3-cyano-2-(triphenylphosphoranylidene)propanoate
174362-09-5

ethyl 3-cyano-2-(triphenylphosphoranylidene)propanoate

2-[1-(4-bromo-2-nitrophenyl)-(E)-methylidene]-3-cyanopropionic acid ethyl ester
926927-55-1

2-[1-(4-bromo-2-nitrophenyl)-(E)-methylidene]-3-cyanopropionic acid ethyl ester

Conditions
ConditionsYield
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

4-bromo-2-nitrobenzaldehyde

methyl trans-4-amino-cyclohexanecarboxylate
62456-15-9

methyl trans-4-amino-cyclohexanecarboxylate

methyl (1r,4r)-4-(6-bromo-2H-indazol-2-yl)cyclohexanecarboxylate

methyl (1r,4r)-4-(6-bromo-2H-indazol-2-yl)cyclohexanecarboxylate

Conditions
ConditionsYield
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

pyrrolidine

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

1-(4-bromo-2-nitrobenzyl)pyrrolidine

1-(4-bromo-2-nitrobenzyl)pyrrolidine

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 3h;85%
4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

6-amino-1H-indazole
6967-12-0

6-amino-1H-indazole

3-phenyl-4H-isoxazol-5-one
1076-59-1

3-phenyl-4H-isoxazol-5-one

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

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
ConditionsYield
In ethanol at 80℃; for 13h;84%
4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

6-amino-1H-indazole
6967-12-0

6-amino-1H-indazole

3-(4-methoxyphenyl)isoxazol-5(4H)-one
31709-47-4

3-(4-methoxyphenyl)isoxazol-5(4H)-one

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

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
ConditionsYield
In ethanol at 80℃; for 10h;84%
4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

6-bromo benzo[c]isoxazole

6-bromo benzo[c]isoxazole

Conditions
ConditionsYield
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

4-bromo-2-nitrobenzaldehyde

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

3-nitro-biphenyl-4-carbaldehyde
515878-88-3

3-nitro-biphenyl-4-carbaldehyde

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In toluene Suzuki Coupling;84%
4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

aniline
62-53-3

aniline

acetophenone
98-86-2

acetophenone

C21H17BrN2O3

C21H17BrN2O3

Conditions
ConditionsYield
With pentafluorophenyl(2,4,6-trimethylphenyl)iodonium tosylate at 20℃; for 24h; Mannich Aminomethylation;83%
4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

(Benzoylmethylene)triphenylphosphorane
20913-05-7

(Benzoylmethylene)triphenylphosphorane

(E)-3-(4-bromo-2-nitrophenyl)-1-phenylprop-2-en-1-one

(E)-3-(4-bromo-2-nitrophenyl)-1-phenylprop-2-en-1-one

Conditions
ConditionsYield
In acetonitrile83%
In toluene at 90℃; Inert atmosphere;
2-(4-chlorophenyl)-3-nitro-2H-chromene
108026-41-1, 57544-16-8

2-(4-chlorophenyl)-3-nitro-2H-chromene

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

A

9-bromo-6-(4-chlorophenyl)-6H-chromeno[3,4-b]quinolin-6-ol

9-bromo-6-(4-chlorophenyl)-6H-chromeno[3,4-b]quinolin-6-ol

B

9-bromo-6-(4-chlorophenyl)-6H-chromeno[3,4-b]quinoline

9-bromo-6-(4-chlorophenyl)-6H-chromeno[3,4-b]quinoline

Conditions
ConditionsYield
With iron; acetic acid at 100℃; for 2h;A 83%
B 8%
pyrrolidine
123-75-1

pyrrolidine

4-bromo-2-nitrobenzaldehyde
5551-12-2

4-bromo-2-nitrobenzaldehyde

5-bromo-2-(pyrrolidin-1-ylmethyl)aniline

5-bromo-2-(pyrrolidin-1-ylmethyl)aniline

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

5551-12-2Relevant articles and documents

Novel functionalized indigo derivatives for organic electronics

Klimovich, Irina V.,Zhilenkov, Alexander V.,Кuznetsova, Lidiya I.,Frolova, Lubov A.,Yamilova, Olga R.,Troyanov, Sergey I.,Lyssenko, Konstantin A.,Troshin, Pavel A.

, (2020/11/24)

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

-

, (2016/07/05)

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

-

Page/Page column 57-58, (2012/07/28)

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.

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