53312-78-0

Usage

Uses

Used in Pharmaceutical Industry:
3-Amino-5-chloro-benzonitrile is used as a key intermediate for the synthesis of new drugs and chemical compounds, contributing to the development of innovative treatments and therapies.
Used in Agrochemical Industry:
3-AMINO-5-CHLORO-BENZONITRILE is utilized as an intermediate in the production of agrochemicals, playing a role in the creation of substances that protect crops and enhance agricultural productivity.
Used in Dye and Pigment Industry:
3-Amino-5-chloro-benzonitrile is used as a building block in the synthesis of dyes and pigments, which are essential for coloring textiles, plastics, and other materials.
Used in Organic Synthesis:
As a reagent in organic chemical reactions, 3-amino-5-chloro-benzonitrile is employed to construct heterocyclic compounds, which are important in the development of various chemical products and pharmaceuticals.
Overall, 3-amino-5-chloro-benzonitrile is a significant component in the chemical industry, with applications spanning across multiple sectors due to its unique properties and synthetic potential.

InChI:InChI=1/C7H5ClN2/c8-6-1-5(4-9)2-7(10)3-6/h1-3H,10H2

Synthetic route

1-nitro-3-chloro-5-cyanobenzene (34662-30-1) → 3-amino-5-chloro-benzonitrile (53312-78-0)

Conditions	Yield
With tin(ll) chloride In N,N-dimethyl-formamide at 20℃;	40%

3-amino-5-chloro-benzonitrile (53312-78-0) → 3-chloro-5-cyano-phenylsulphonyl chloride (1131397-77-7)

Conditions	Yield
Stage #1: 3-amino-5-chloro-benzonitrile With hydrogenchloride; sodium nitrite In water at 0℃; for 0.583333h; Stage #2: With sulfur dioxide; acetic acid; copper dichloride In water at 0℃; for 1.25h;	97%

2-isocyano-2-methylbutane (13947-76-7) + 3-amino-5-chloro-benzonitrile (53312-78-0) → N-(3-Chloro-5-cyanophenyl)-N'-tert-pentylcarbodiimide (150596-95-5)

Conditions	Yield
With 4 A molecular sieve; silver(l) oxide; nickel dichloride In benzene for 1h; Heating; effectivity of the other catalysts and oxidants;	86%
With 4 A molecular sieve; silver(l) oxide; nickel dichloride In benzene for 1h; Heating;	86%

2-amino-6-methyl-4-chloropyrimidine (5600-21-5) + 3-amino-5-chloro-benzonitrile (53312-78-0) → 3-((2-amino-6-methylpyrimidin-4-yl)amino)-5-chlorobenzonitrile

Conditions	Yield
With hydrogenchloride In ethanol; water at 140℃; for 1.5h; Microwave irradiation; Sealed tube;	73%

3-(tert-butyloxycarbonylamino)propionic acid (3303-84-2) + 3-amino-5-chloro-benzonitrile (53312-78-0) → tert-butyl (3-((3-chloro-5-cyanophenyl)amino)-3-oxopropyl)carbamate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 25℃; for 1h;	70.8%

tert-butylamine (75-64-9) + 3-amino-5-chloro-benzonitrile (53312-78-0) → N-t-butyl-3-chloro-5-cyano-benzenesulfonamide (1203655-74-6)

Conditions	Yield
Stage #1: 3-amino-5-chloro-benzonitrile With hydrogenchloride; sodium nitrite In water at -5℃; Stage #2: With sulfur dioxide; acetic acid; copper dichloride In water at -10 - 20℃; Stage #3: tert-butylamine With pyridine In tetrahydrofuran at 0 - 20℃;	52%

2-(4-(2-bromo-5-chlorobenzoyl)phenoxy)acetic acid + 3-amino-5-chloro-benzonitrile (53312-78-0) → 2-(4-(2-bromo-5-chlorobenzoyl)phenoxy)-N-(3-chloro-5-cyanophenyl)acetamide

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	25%

8-(bis(4-methoxybenzyl)amino)-6-chloroimidazo[1,2-b]pyridazine-3-carbonitrile (1220631-64-0) + 3-amino-5-chloro-benzonitrile (53312-78-0) → 8-amino-6-((3-chloro-5-cyanophenyl)amino)imidazo[1,2-b]pyridazine-3-carbonitrile (1220628-11-4)

Conditions	Yield
Stage #1: 8-(bis(4-methoxybenzyl)amino)-6-chloroimidazo[1,2-b]pyridazine-3-carbonitrile; 3-amino-5-chloro-benzonitrile With copper(l) iodide; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) In ISOPROPYLAMIDE at 125℃; for 13h; Inert atmosphere; Stage #2: With triethylsilane; trifluoroacetic acid In dichloromethane for 1h;	12.61%

thiophosgene (463-71-8) + 3-amino-5-chloro-benzonitrile (53312-78-0) → 3-Chloro-5-isothiocyanato-benzonitrile (185500-56-5)

Conditions	Yield
In ethyl acetate at 75℃; for 1.5h;

3-amino-5-chloro-benzonitrile (53312-78-0) + 4-methyl-N'-[(1E)-pyridin-2-ylmethylene]benzenesulfonohydrazide → 3-chloro-5-(5-pyridin-2-yl-tetrazol-2-yl)-benzonitrile

Conditions	Yield
Stage #1: 3-amino-5-chloro-benzonitrile With hydrogenchloride; sodium nitrite In ethanol at 0℃; Stage #2: 4-methyl-N'-[(1E)-pyridin-2-ylmethylene]benzenesulfonohydrazide With sodium hydroxide In ethanol at 0℃;

3-amino-5-chloro-benzonitrile (53312-78-0) → (3-Chloro-5-cyano-phenyl)-(1,1,2-trimethyl-propyl)-carbodiimide

Conditions	Yield
Multi-step reaction with 3 steps 3: PPh3, Et3N, CCl4 / CH2Cl2 View Scheme

3-amino-5-chloro-benzonitrile (53312-78-0) → (3-Chloro-5-cyano-phenyl)-(1-ethyl-1-methyl-propyl)-carbodiimide

Conditions	Yield
Multi-step reaction with 3 steps 3: PPh3, Et3N, CCl4 / CH2Cl2 View Scheme

3-amino-5-chloro-benzonitrile (53312-78-0) → 1-(3-Chloro-5-cyano-phenyl)-3-(1-ethyl-1-methyl-propyl)-thiourea

3-amino-5-chloro-benzonitrile (53312-78-0) → 1-(3-Chloro-5-cyano-phenyl)-3-(1,1,2-trimethyl-propyl)-thiourea

3-amino-5-chloro-benzonitrile (53312-78-0) → (3-Chloro-5-cyano-phenyl)-(1,1-diethyl-propyl)-carbodiimide

Conditions	Yield
Multi-step reaction with 3 steps 3: PPh3, Et3N, CCl4 / CH2Cl2 View Scheme

3-amino-5-chloro-benzonitrile (53312-78-0) → 1-(3-Chloro-5-cyano-phenyl)-3-(1,1-diethyl-propyl)-thiourea

3-amino-5-chloro-benzonitrile (53312-78-0) → C15H18ClN5

Conditions	Yield
Multi-step reaction with 4 steps 3: PPh3, Et3N, CCl4 / CH2Cl2 4: iPr2EtN View Scheme

3-amino-5-chloro-benzonitrile (53312-78-0) → C15H18ClN5

Conditions	Yield
Multi-step reaction with 4 steps 3: PPh3, Et3N, CCl4 / CH2Cl2 4: iPr2EtN View Scheme

3-amino-5-chloro-benzonitrile (53312-78-0) → C16H20ClN5

Conditions	Yield
Multi-step reaction with 4 steps 3: PPh3, Et3N, CCl4 / CH2Cl2 4: iPr2EtN View Scheme

3-amino-5-chloro-benzonitrile (53312-78-0) → N-(3-Chloro-5-cyanophenyl)-N'-tert-pentylcarbodiimide (150596-95-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: ethyl acetate / 1.5 h / 75 °C 2: ethyl acetate / 1 h / Ambient temperature 3: Ph3P, Et3N / CH2Cl2; CCl4 / 5 h / Heating View Scheme

3-amino-5-chloro-benzonitrile (53312-78-0) → N-(3-Chloro-5-cyanophenyl)-N'-cyano-N''-tert-pentylguanidine

Conditions	Yield
Multi-step reaction with 4 steps 1: ethyl acetate / 1.5 h / 75 °C 2: ethyl acetate / 1 h / Ambient temperature 3: Ph3P, Et3N / CH2Cl2; CCl4 / 5 h / Heating 4: diisopropylethylamine / dimethylformamide / 15 h / 100 °C View Scheme

3-amino-5-chloro-benzonitrile (53312-78-0) → tert-Butyl-(3-chloro-5-cyano-phenyl)-carbodiimide (1026006-49-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: ethyl acetate / 1.5 h / 75 °C 2: ethyl acetate / 1 h / Ambient temperature 3: Ph3P, Et3N / CH2Cl2; CCl4 / 5 h / Heating View Scheme

3-amino-5-chloro-benzonitrile (53312-78-0) → 1-tert-Butyl-3-(3-chloro-5-cyano-phenyl)-thiourea (185500-53-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethyl acetate / 1.5 h / 75 °C 2: ethyl acetate / 1 h / Ambient temperature View Scheme

3-amino-5-chloro-benzonitrile (53312-78-0) → 1-(3-Chloro-5-cyano-phenyl)-3-(1,1-dimethyl-propyl)-thiourea (144930-87-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethyl acetate / 1.5 h / 75 °C 2: ethyl acetate / 1 h / Ambient temperature View Scheme

3-amino-5-chloro-benzonitrile (53312-78-0) → C13H14ClN5

Conditions	Yield
Multi-step reaction with 4 steps 1: ethyl acetate / 1.5 h / 75 °C 2: ethyl acetate / 1 h / Ambient temperature 3: Ph3P, Et3N / CH2Cl2; CCl4 / 5 h / Heating 4: diisopropylethylamine / dimethylformamide / 15 h / 100 °C View Scheme

3-amino-5-chloro-benzonitrile (53312-78-0) → 3-amino-5-chlorobenzylamine

Conditions	Yield
With dimethylsulfide borane complex In tetrahydrofuran at 20℃; for 3h; Heating / reflux;

2-methyl-4-chlorobenzaldehyde (40137-29-9) + ethyl 2,4-dioxo-5-methylhexanoate (64195-85-3) + 3-amino-5-chloro-benzonitrile (53312-78-0) → 3-chloro-5-[2-(4-chloro-2-methyl-phenyl)-4-hydroxy-3-isobutyryl-5-oxo-2,5-dihydro-pyrrol-1-yl]-benzonitrile (1441737-09-2)

Conditions	Yield
With acetic acid at 120℃; for 16h;	1.8 g

(3R*,4R*)-2-isobutyl-1-oxo-3-(thiophen-2-yl)-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acid + 3-amino-5-chloro-benzonitrile (53312-78-0) → C25H22ClN3O2S

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In dichloromethane; ethyl acetate at 0 - 20℃; for 16h;

3-amino-5-chloro-benzonitrile (53312-78-0) → tert-butyl (3-((3-(aminomethyl)-5-chlorophenyl)amino)-3-oxopropyl)carbamate

Conditions	Yield
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 25 °C 2: hydrogen; ammonium hydroxide / methanol / 4 h / 25 °C View Scheme

3-amino-5-chloro-benzonitrile (53312-78-0) → tert-butyl (3-((3-chloro-5-((6-chloro-2,3,4,9-tetrahydro-1Hpyrido[3,4-b] indole-2-carboxamido) methyl)phenyl)amino)-3-oxopropyl)carbamate

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 25 °C 2.1: hydrogen; ammonium hydroxide / methanol / 4 h / 25 °C 3.1: triethylamine / dichloromethane / 0.5 h / 0 °C 3.2: 3 h / 25 °C View Scheme

Upstream product

• 34662-30-1 1-nitro-3-chloro-5-cyanobenzene 

Downstream Products

• 150596-95-5 N-(3-Chloro-5-cyanophenyl)-N'-tert-pentylcarbodiimide 
• 1220628-11-4 8-amino-6-((3-chloro-5-cyanophenyl)amino)imidazo[1,2-b]pyridazine-3-carbonitrile 
• 1131397-77-7 3-chloro-5-cyano-phenylsulphonyl chloride 
• 1441737-09-2 3-chloro-5-[2-(4-chloro-2-methyl-phenyl)-4-hydroxy-3-isobutyryl-5-oxo-2,5-dihydro-pyrrol-1-yl]-benzonitrile 
• 1203655-74-6 N-t-butyl-3-chloro-5-cyano-benzenesulfonamide 
• 683740-35-4 3-amino-5-chlorobenzylamine 
• 144930-87-0 1-(3-Chloro-5-cyano-phenyl)-3-(1,1-dimethyl-propyl)-thiourea 
• 185500-53-2 1-tert-Butyl-3-(3-chloro-5-cyano-phenyl)-thiourea 
• 1026006-49-4 tert-Butyl-(3-chloro-5-cyano-phenyl)-carbodiimide 

Relevant academic research and scientific papers

Aminoacetamide acyl guanidines as beta-secretase inhibitors

There is provided a series of substituted acyl guanidines of Formula (Ik) or a stereoisomer; or a pharmaceutically acceptable salt thereof, wherein R2, R3, R4, R5, R25, R26 and R27 as defined herein, their pharmaceutical compositions and methods of use. These compounds inhibit the processing of amyloid precursor protein (APP) by β-secretase and, more specifically, inhibit the production of Aβ-peptide. The present disclosure is directed to compounds useful in the treatment of neurological disorders related to β-amyloid production, such as Alzheimer's disease and other conditions affected by anti-amyloid activity.