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453-71-4

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453-71-4 Usage

Chemical Properties

white to light yellow crystal powder

Uses

4-Fluoro-3-nitrobenzoic acid was used:as starting reagent in the preparation of novel benzimidazoles having antimycobacterial activityin preparation of series of novel acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors containing benzimidazole core structurein preparation of bis(heterocyclic) skeletal precursors for the Pictet-Spengler reactionin solid-phase synthesis of trisubstituted [1,3,5]triazino[1,2-a]benzimidazole-2,4(3H,10H)-diones

Check Digit Verification of cas no

The CAS Registry Mumber 453-71-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,5 and 3 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 453-71:
(5*4)+(4*5)+(3*3)+(2*7)+(1*1)=64
64 % 10 = 4
So 453-71-4 is a valid CAS Registry Number.
InChI:InChI=1/C7H4FNO4/c8-5-2-1-4(7(10)11)3-6(5)9(12)13/h1-3H,(H,10,11)

453-71-4 Well-known Company Product Price

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  • Alfa Aesar

  • (A10800)  4-Fluoro-3-nitrobenzoic acid, 98%   

  • 453-71-4

  • 5g

  • 284.0CNY

  • Detail
  • Alfa Aesar

  • (A10800)  4-Fluoro-3-nitrobenzoic acid, 98%   

  • 453-71-4

  • 25g

  • 1125.0CNY

  • Detail
  • Alfa Aesar

  • (A10800)  4-Fluoro-3-nitrobenzoic acid, 98%   

  • 453-71-4

  • 100g

  • 3606.0CNY

  • Detail

453-71-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Fluoro-3-nitrobenzoic acid

1.2 Other means of identification

Product number -
Other names 5-Carboxy-2-fluoronitrobenzene

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:453-71-4 SDS

453-71-4Synthetic route

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

Conditions
ConditionsYield
With sulfuric acid; potassium nitrate at 20℃;90%
With sulfuric acid; potassium nitrate at 20℃;88%
With sulfuric acid; nitric acid at 20℃; for 10h;75%
trimethylsilylazide
4648-54-8

trimethylsilylazide

4-fluoro-3-nitrobenzoyl chloride
400-94-2

4-fluoro-3-nitrobenzoyl chloride

A

3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

B

1-(4-fluoro-3-nitrophenyl)-1,4-dihydro-5H-tetrazol-5-one
1309832-87-8

1-(4-fluoro-3-nitrophenyl)-1,4-dihydro-5H-tetrazol-5-one

Conditions
ConditionsYield
at 20 - 90℃; Inert atmosphere;A n/a
B 70%
4-fluoro-3-nitrobenzonitrile
1009-35-4

4-fluoro-3-nitrobenzonitrile

3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

Conditions
ConditionsYield
With sulfuric acid at 120℃; for 8h; Sealed tube;52%
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

Conditions
ConditionsYield
With nitric acid
4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

nitric acid
7697-37-2

nitric acid

3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

nitric acid
7697-37-2

nitric acid

A

3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

B

4-Fluoronitrobenzene
350-46-9

4-Fluoronitrobenzene

p-fluorotoluene
352-32-9

p-fluorotoluene

3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: KMnO4
2: nitric acid
View Scheme
toluene-4-diazonium ; sulfate

toluene-4-diazonium ; sulfate

3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
2: KMnO4
3: nitric acid
View Scheme
C7H3FNO4Pol

C7H3FNO4Pol

3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

Conditions
ConditionsYield
Stage #1: C7H3FNO4Pol With acetic anhydride In dichloromethane for 2h;
Stage #2: With trifluoroacetic acid In 1,2-dichloro-ethane for 1h;
TFAN1,2-dichloroethane

TFAN1,2-dichloroethane

4-fluoro-3-nitrobenzoyl chloride
400-94-2

4-fluoro-3-nitrobenzoyl chloride

isopropyl alcohol
67-63-0

isopropyl alcohol

3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

Conditions
ConditionsYield
With acetic anhydride; N-ethyl-N,N-diisopropylamine In water; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; acetonitrile
4-fluoro-3-nitrotoluene
446-11-7

4-fluoro-3-nitrotoluene

3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

Conditions
ConditionsYield
With potassium dichromate; sulfuric acid; acetic acid Reflux;
3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

4-fluoro-3-nitrobenzoyl chloride
400-94-2

4-fluoro-3-nitrobenzoyl chloride

Conditions
ConditionsYield
With thionyl chloride In 1,2-dichloro-ethane at 80℃; for 12 - 16h; Product distribution / selectivity;100%
With thionyl chloride for 4h; Reflux;100%
With oxalyl dichloride In N,N-dimethyl-formamide; benzene at 0℃; for 6h; Chlorination;99%
3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

aniline
62-53-3

aniline

2-nitrodiphenylamine-4-carboxylic acid
16927-49-4

2-nitrodiphenylamine-4-carboxylic acid

Conditions
ConditionsYield
Stage #1: 3-nitro-4-fluorobenzoic acid; aniline In ethanol for 16h; Reflux;
Stage #2: With hydrogenchloride In ethanol; water
100%
In ethanol at 20℃; for 1h;81%
cetyltrimethylammonim bromide In water at 73℃; Mechanism; Rate constant; or without CTAB-catalysis;
2-[(2-pyridin-2-ylquinoline-4-carbonyl)amino]ethylammonium chloride

2-[(2-pyridin-2-ylquinoline-4-carbonyl)amino]ethylammonium chloride

3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

2-pyridin-2-yl-quinoline-4-carboxylic acid [2-(4-fluoro-3-nitro-benzoylamino)-ethyl]-amide
778647-45-3

2-pyridin-2-yl-quinoline-4-carboxylic acid [2-(4-fluoro-3-nitro-benzoylamino)-ethyl]-amide

Conditions
ConditionsYield
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 66h;100%
3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

4-fluoro-3-nitro-benzoic acid methyl ester
329-59-9

4-fluoro-3-nitro-benzoic acid methyl ester

Conditions
ConditionsYield
100%
Multi-step reaction with 2 steps
1: (COCl)2; DMF / CH2Cl2 / 0 - 25 °C
2: 0 °C
View Scheme
Multi-step reaction with 2 steps
1: oxalyl chloride; N,N-dimethylformamide / CH2Cl2 / 16 h / 22 °C
2: 52.4 g / triethylamine / CH2Cl2 / 16 h / 22 °C
View Scheme
methanol
67-56-1

methanol

3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

4-fluoro-3-nitro-benzoic acid methyl ester
329-59-9

4-fluoro-3-nitro-benzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: methanol; 3-nitro-4-fluorobenzoic acid With thionyl chloride at 0 - 20℃;
Stage #2: With water; sodium hydrogencarbonate In ethyl acetate
100%
With sulfuric acid at 80℃;100%
With sulfuric acid at 65℃; for 36h; Large scale;100%
3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

L-valine methylester hydrochloride
6306-52-1

L-valine methylester hydrochloride

4-((S)-1-(methoxycarbonyl)-2-methylpropylamino)-3-nitrobenzoic acid

4-((S)-1-(methoxycarbonyl)-2-methylpropylamino)-3-nitrobenzoic acid

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20 - 80℃; for 16h;100%
tert-butyl (4-amino-2-methylbutan-2-yl)carbamate
880100-43-6

tert-butyl (4-amino-2-methylbutan-2-yl)carbamate

3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

4-(3-tert-butoxycarbonylamino-3-methyl-butylamino)-3-nitro-benzoic acid
935873-16-8

4-(3-tert-butoxycarbonylamino-3-methyl-butylamino)-3-nitro-benzoic acid

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20 - 60℃; for 168h;100%
3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

(trifluoromethyl)trimethylsilane
81290-20-2

(trifluoromethyl)trimethylsilane

1,1,1,3,3,3-hexafluoro-2-(4-fluoro-3-nitrophenyl)propan-2-ol
35445-59-1

1,1,1,3,3,3-hexafluoro-2-(4-fluoro-3-nitrophenyl)propan-2-ol

Conditions
ConditionsYield
Stage #1: 3-nitro-4-fluorobenzoic acid With thionyl chloride In N,N-dimethyl-formamide for 2h; Reflux;
Stage #2: (trifluoromethyl)trimethylsilane With tetramethylammonium fluoride In 1,2-dimethoxyethane at 20℃; for 12.3333h; Inert atmosphere; Cooling with ice;
100%
3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

ethyl 2-sulfanylacetate
623-51-8

ethyl 2-sulfanylacetate

4-ethoxycarbonylmethylsulfanyl-3-nitrobenzoic acid
204863-51-4

4-ethoxycarbonylmethylsulfanyl-3-nitrobenzoic acid

Conditions
ConditionsYield
With sodium acetate In water at 90℃; for 24h; Inert atmosphere;100%
3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

phenol
108-95-2

phenol

3-nitro-4-phenoxybenzoic acid
202209-14-1

3-nitro-4-phenoxybenzoic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In water at 80℃; for 6h;100%
3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

L-leucine tert-butyl ester hydrochloride
2748-02-9

L-leucine tert-butyl ester hydrochloride

(S)-2-(4-fluoro-3-nitro-benzoylamino)-4-methyl-pentanoic acid tert-butyl ester
1586791-32-3

(S)-2-(4-fluoro-3-nitro-benzoylamino)-4-methyl-pentanoic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: 3-nitro-4-fluorobenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: L-leucine tert-butyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 4h;
100%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 4h;
hexamethylene imine
111-49-9

hexamethylene imine

3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

4-azepan-1-yl-3-nitro-benzoic acid
92109-03-0

4-azepan-1-yl-3-nitro-benzoic acid

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 1h;100%
3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

(4-fluoro-3-nitrophenyl)methanol
20274-69-5

(4-fluoro-3-nitrophenyl)methanol

Conditions
ConditionsYield
Stage #1: 3-nitro-4-fluorobenzoic acid With sodium tetrahydroborate In tetrahydrofuran at 0℃; for 1h;
Stage #2: With boron trifluoride diethyl etherate In tetrahydrofuran at 0 - 20℃; for 3h;
99.1%
Stage #1: 3-nitro-4-fluorobenzoic acid With sodium tetrahydroborate In tetrahydrofuran at 0℃; for 1h;
Stage #2: With boron trifluoride diethyl etherate In tetrahydrofuran at 0 - 20℃; for 3h;
99.1%
Stage #1: 3-nitro-4-fluorobenzoic acid With sodium tetrahydroborate In tetrahydrofuran at 0℃; for 1h;
Stage #2: With boron trifluoride dimethyl etherate In tetrahydrofuran at 0 - 20℃; for 3h;
97.4%
3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

4-fluoro-3-nitro-benzoic acid methyl ester
329-59-9

4-fluoro-3-nitro-benzoic acid methyl ester

Conditions
ConditionsYield
In diethyl ether ice cooling;99%
methanol
67-56-1

methanol

3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

isobutylamine
78-81-9

isobutylamine

ethyl iodide
75-03-6

ethyl iodide

1,1'-Thiocarbonyldiimidazole
6160-65-2

1,1'-Thiocarbonyldiimidazole

2-ethylsulfanyl-1-isobutyl-1H-benzoimidazole-5-carboxylic acid methyl ester

2-ethylsulfanyl-1-isobutyl-1H-benzoimidazole-5-carboxylic acid methyl ester

Conditions
ConditionsYield
Multistep reaction;99%
3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

methylamine
74-89-5

methylamine

4-(methylamino)-3-nitrobenzoic acid
41263-74-5

4-(methylamino)-3-nitrobenzoic acid

Conditions
ConditionsYield
In methanol; ethanol at 20℃; for 2h;99%
In methanol at 20℃; for 18h;99%
In methanol at 20℃; for 10h;98%
3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

4-fluoro-3-nitro-benzoic acid methyl ester
329-59-9

4-fluoro-3-nitro-benzoic acid methyl ester

Conditions
ConditionsYield
With methanol In hexanes; dichloromethane at 0℃; for 1h;99%
In methanol; hexane; toluene at 0 - 20℃; for 0.5h;92%
3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

methyl iodide
74-88-4

methyl iodide

4-fluoro-3-nitro-benzoic acid methyl ester
329-59-9

4-fluoro-3-nitro-benzoic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;99%
With potassium carbonate In acetone
Trimethyl orthoacetate
1445-45-0

Trimethyl orthoacetate

3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

4-fluoro-3-nitro-benzoic acid methyl ester
329-59-9

4-fluoro-3-nitro-benzoic acid methyl ester

Conditions
ConditionsYield
In toluene at 80℃; for 8h; Esterification;98%
methanol
67-56-1

methanol

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

isobutylamine
78-81-9

isobutylamine

allyl bromide
106-95-6

allyl bromide

3-allyl-1-isobutyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid methyl ester

3-allyl-1-isobutyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid methyl ester

Conditions
ConditionsYield
Solid phase reaction;98%
3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

4-(2-hydroxyethylthio)-3-nitrobenzoic acid
124416-06-4

4-(2-hydroxyethylthio)-3-nitrobenzoic acid

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide98%
3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-decanol
678-39-7

3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-decanol

3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl 4-fluoro-3-nitrobenzoate
1390621-27-8

3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl 4-fluoro-3-nitrobenzoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 0.5h; Microwave irradiation; Inert atmosphere;98%
3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

isopropyl alcohol
67-63-0

isopropyl alcohol

3-nitro-4-isopropoxybenzoic acid
156629-52-6

3-nitro-4-isopropoxybenzoic acid

Conditions
ConditionsYield
Stage #1: isopropyl alcohol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.25h; Inert atmosphere;
Stage #2: 3-nitro-4-fluorobenzoic acid In tetrahydrofuran; mineral oil at 0 - 20℃; for 3.5h; Inert atmosphere;
98%
3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

3-nitro-4-(m-tolylamino)benzoic acid
452088-49-2

3-nitro-4-(m-tolylamino)benzoic acid

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one at 90℃; for 16h; Inert atmosphere;98%
3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

3-amino-4-fluorobenzoic acid
2365-85-7

3-amino-4-fluorobenzoic acid

Conditions
ConditionsYield
With hydrogen; 5%-palladium/activated carbon In methanol for 6h;97%
With hydrogen; palladium 10% on activated carbon In methanol under 760.051 Torr; for 3h;96%
With 5%-palladium/activated carbon; hydrogen In ethanol under 12001.2 Torr; Flow reactor;95%
ethanol
64-17-5

ethanol

3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

ethyl 4-fluoro-3-nitrobenzoate
367-80-6

ethyl 4-fluoro-3-nitrobenzoate

Conditions
ConditionsYield
With sulfuric acid97%
With hydrogenchloride for 15h; Heating / reflux;95%
With sulfuric acid for 8h; Reflux;93%
3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

ethanolamine
141-43-5

ethanolamine

4-(2-hydroxy-ethylamino)-3-nitro-benzoic acid
59320-14-8

4-(2-hydroxy-ethylamino)-3-nitro-benzoic acid

Conditions
ConditionsYield
In isopropyl alcohol at 20℃; for 18h;97%
In methanol at 20℃; for 4h;89%
3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

borane tetrahydrofuran

borane tetrahydrofuran

(4-fluoro-3-nitrophenyl)methanol
20274-69-5

(4-fluoro-3-nitrophenyl)methanol

Conditions
ConditionsYield
In tetrahydrofuran; water97%
3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

4-fluoro-3-nitrobenzamide
349-02-0

4-fluoro-3-nitrobenzamide

Conditions
ConditionsYield
With N-hydroxybenzotriazole ammonium salt; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide; acetonitrile at 0 - 20℃; for 4h;97%
With N-hydroxybenzotriazole ammonium salt; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide; acetonitrile at 0 - 20℃; for 4h;97%
Stage #1: 3-nitro-4-fluorobenzoic acid With thionyl chloride at 80℃; for 2h;
Stage #2: With ammonia In tetrahydrofuran; dichloromethane at 0℃; for 1h;
96%
1-amino-3-methylbutane
107-85-7

1-amino-3-methylbutane

ethanol
64-17-5

ethanol

3-nitro-4-fluorobenzoic acid
453-71-4

3-nitro-4-fluorobenzoic acid

ethyl 4-(isopentylamino)-3-nitrobenzoate

ethyl 4-(isopentylamino)-3-nitrobenzoate

Conditions
ConditionsYield
Stage #1: ethanol; 3-nitro-4-fluorobenzoic acid With sulfuric acid Reflux;
Stage #2: 1-amino-3-methylbutane With triethylamine Reflux;
97%

453-71-4Relevant articles and documents

Substituent effects on the isomerization of hydrazone switches driven by the intramolecular hydrogen bond

Lu, Chaocao,Htan, Bu,Fu, Shitao,Ma, Chunmiao,Gan, Quan

, p. 4010 - 4016 (2019/07/03)

In this work, the substituent effects on hydrogen bonding in one kind of hydrazone-based switch are revealed. The E/Z isomerization ratios of these hydrazones and their intramolecular hydrogen bond strengths in the Z form were evaluated using NMR technique. Linear correlations between these parameters and Hammett empirical values for substituent effects are explored as well.

IMINOTETRAHYDROPYRIMIDINONE DERIVATIVES AS PLASMEPSIN V INHIBITORS

-

Page/Page column 53, (2017/07/05)

A series of 2-imino-6-methyltetrahydropyrimidin-4(lH)-one derivatives, substituted in the 6-position by a phenyl moiety which in turn is meta-substituted by an optionally substituted unsaturated fused bicyclic ring system containing at least one nitrogen atom, being selective inhibitors of plasmepsin V activity, are beneficial as pharmaceutical agents, especially in the treatment of malaria.

Stable and easily accessible functional dyes: Dihydrotetraazaanthracenes as versatile precursors for higher acenes

Gampe, Dominique Mario,Kaufmann, Martin,Jakobi, D?rthe,Sachse, Torsten,Presselt, Martin,Beckert, Rainer,G?rls, Helmar

, p. 7571 - 7581 (2015/05/13)

Abstract A series of new dihydrotetraazaanthracenes and one new dihydrotetraazatetracene as substances for applications in organoelectronic devices and as suitable building blocks for higher azaacenes was synthesised. The condensation of aromatic diamines with dichlorodicyanopyrazine led to these tricyclic/tetracyclic compounds. Syntheses of N-substituted phenylenediamines were developed to enable the introduction of multiple functional groups such as ester, amino, or nitro groups on the chromophoric system. Relationships between the structure and the spectroscopic properties could be derived from UV/Vis absorption and fluorescence spectroscopy, as well as by DFT and TD-DFT calculations of molecular and aggregate structures. The absorption spectra are dominated by π-π transitions of the single molecules, whereas aggregation needs to be taken into account to obtain reasonable agreement between theory and experiment in certain cases. Single-crystal X-ray analyses were carried out to examine the morphology and solid packing effects. Finally, a dihydrotetraazaanthracene was used as a building-block to create a mesoionic octaazapentacene. Dihydroazaacenes: A series of dihydrotetraazaanthracenes and one new dihydrotetraazatetracene as substances for applications in organoelectronic devices and as suitable building blocks for higher azaacenes was synthesised. Single-crystal X-ray analyses were carried out to examine the morphology and solid packing effects. Finally, a dihydrotetraazaanthracene was used as a building-block to create a mesoionic octaazapentacene.

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