1482-62-8

Basic information

• Product Name: 1-(4-chlorophenyl)-3-cyanoguanidine
• Synonyms: 1-(4-chlorophenyl)-3-cyanoguanidine;N-(4-Chlorophenyl)-N’-cyanoguanidine;N-(4-Chlorophenyl)-N’4-CHLOROPHENYLCYANOGUANIDINE;(4-chlorophenyl)-dicyanodiamide;P-CHLOROPHENYL-CYANOGUANIDINE;1-CYANO-3-(4-CHLOROPHENYL)-GUANIDINE;GUANIDINE, -(4-CHLOROPHENYL)-N''-CYANO
• CAS NO: 1482-62-8
• Molecular Formula: C₈H₇ClN₄
• Molecular Weight: 194.62098
• EINECS: 216-043-5
• Product Categories: Benzene series;Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 1482-62-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 202-204 °C
• Boiling Point: 340.2 °C at 760 mmHg
• Flash Point: 159.5 °C
• Appearance: /
• Density: 1.34g/cm³
• Vapor Pressure: 8.74E-05mmHg at 25°C
• Refractive Index: 1.626
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.92±0.10(Predicted)
• CAS DataBase Reference: 1-(4-chlorophenyl)-3-cyanoguanidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-chlorophenyl)-3-cyanoguanidine(1482-62-8)
• EPA Substance Registry System: 1-(4-chlorophenyl)-3-cyanoguanidine(1482-62-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1482-62-8(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 1482-62-8 differently. You can refer to the following data:
1. 1-(4-chlorophenyl)-3-cyanoguanidine used in the preparation of antimalarial agents.
2. Halo-aryl substituted guanidine derivative used in the preparation of antimalarial agents. Proguanil USP Related Compound E (1-(4-chlorophenyl)-3-cyanoguanidine).

Synthesis Reference(s)

The Journal of Organic Chemistry, 24, p. 1809, 1959 DOI: 10.1021/jo01093a619

InChI:InChI=1/C8H7ClN4/c9-6-1-3-7(4-2-6)13-8(11)12-5-10/h1-4H,(H3,11,12,13)

Synthetic route

sodium dicyanamide (1934-75-4) + 4-chloro-aniline (106-47-8) → 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8)

Conditions	Yield
oxonium; acetic acid In water at 40℃; Rate constant; Mechanism;	100%
With hydrogenchloride In water at 60℃; for 3h;	87%
Stage #1: sodium dicyanamide; 4-chloro-aniline With hydrogenchloride In water at 50 - 90℃; for 18h; Stage #2: With sodium hydrogencarbonate In water for 0.25h;	78.3%

N-(4-chloro-phenylazo)-N'-cyano-guanidine (3713-20-0) → 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8)

Conditions	Yield
With hydrogenchloride; acetone
With hydrogenchloride; 1-ethoxyethanol

4-chlorophenylbiguanide (5304-59-6) → 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) + 1-(4-chlorophenyl)-3-amidinourea (58247-24-8)

Conditions	Yield
With hydrogenchloride; sodium nitrite

calcium cyanamide (156-62-7) + cyanogen chloride (506-77-4) → 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8)

Conditions	Yield
With water anschliessend mit einer aus 4-Chlor-anilin und wss.Salzsaeure bereiteten Loesung;

3-cyano-2-methylisothiourea (15760-26-6) + 4-chloro-aniline (106-47-8) → 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8)

Conditions	Yield
(i) aq. NaOH, iPrOH, (ii) /BRN= 471359/, aq. HCl; Multistep reaction;

p-chloroaniline hydrochloride (20265-96-7) + sodium dicyanamide (1934-75-4) → 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8)

4-chloro-aniline (106-47-8) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8)

Conditions	Yield
With ammonium hydroxide Multistep reaction;

4-chloro-benzenediazodicyanodiamide → 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8)

Conditions	Yield
With hydrogenchloride Zersetzen des Reaktionsproduktes mit Wasser;

p-chloroaniline hydrochloride (20265-96-7) + sodium-compound of dicyanamide → 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8)

Conditions	Yield
With water

dicyandiamide (127099-85-8, 780722-26-1) + p-chloroaniline hydrochloride (20265-96-7) → 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8)

Conditions	Yield
Stage #1: p-chloroaniline hydrochloride With sodium nitrite In water at 10℃; for 0.5h; Stage #2: dicyandiamide With sodium carbonate In water at 20 - 60℃; for 2h; Temperature;

1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) + phenyl isothiocyanate (103-72-0) → 4-[(4-chlorophenyl)imino]-6-imino-1-phenyl-1,3,5-triazinane-2-thione

Conditions	Yield
With sodium methylate In acetone at 80℃; for 0.0833333h; Microwave irradiation;	90%

2,6-diisopropyl-4-phenoxy-1-isothiocyanobenzene (80058-93-1) + 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) → 4-[(4-chlorophenyl)imino]-1-(2,6-diisopropyl-4-phenoxyphenyl)-6-imino-1,3,5-triazinane-2-thione

Conditions	Yield
With sodium methylate In acetone at 80℃; for 0.0666667h; Microwave irradiation;	89%

8C2H4O2*C36H54N8 + 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) → 8C2H4O2*C84H96Cl6N32

Conditions	Yield
In butan-1-ol for 72h; Heating;	84.5%
In butan-1-ol at 90℃; for 72h;	84.5%

ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (4506-71-2) + 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) → N-(4-Chloro-phenyl)-N'-(4-oxo-3,4,5,6,7,8-hexahydro-benzo[4,5]thieno[2,3-d]pyrimidin-2-yl)-guanidine (86320-01-6)

Conditions	Yield
With hydrogenchloride	75%

1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) + 2-carbomethoxyaniline (134-20-3) → N-(4-Chloro-phenyl)-N'-(4-oxo-3,4-dihydro-quinazolin-2-yl)-guanidine (86327-86-8)

Conditions	Yield
With hydrogenchloride Heating;	67%

piperazine (110-85-0) + 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) → N,N'-bis-(4-chlorophenylamidino)-1,4-piperazinedicarboxamidine (5636-92-0)

Conditions	Yield
With hydrogenchloride In methanol; water at 120℃; for 2h; Microwave irradiation;	46%

piperazine (110-85-0) + 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) + N-(2-chlorophenyl)-N’-cyanoguanidine (41410-43-9) → N-(2-chlorophenylamidino)-N’-(4-chlorophenylamidino)-1,4-piperazinedicarboxamidine

Conditions	Yield
With hydrogenchloride In methanol; water at 120℃; for 1h; Microwave irradiation;	36%

pyrrolidine (123-75-1) + 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) → N-(4-chloro-phenyl)-N'-(pyrrolidine-1-carboximidoyl)-guanidine

Conditions	Yield
With ethanol; copper(II) sulfate
With ethanol; copper(II) sulfate

piperidine (110-89-4) + 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) → N-(4-chloro-phenyl)-N'-(piperidine-1-carboximidoyl)-guanidine

Conditions	Yield
With 2-ethoxy-ethanol; water; copper(II) sulfate Behandeln des Reaktionsproduktes mit wss. Salzsaeure und mit Natriumsulfid;
With 2-ethoxy-ethanol; water; copper(II) sulfate Behandeln des Reaktionsproduktes mit wss. Salzsaeure und mit Natriumsulfid;

morpholine (110-91-8) + 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) → N-(4-chloro-phenyl)-N'-(morpholine-4-carboximidoyl)-guanidine (18413-33-7)

Conditions	Yield
With 2-ethoxy-ethanol; copper(II) sulfate Behandeln des Reaktionsprodukts mit wss. HCl und mit Na2S;

propylamine (107-10-8) + 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) → N1-(p-Chlorophenyl)-N5-n-propylbiguanide (49871-96-7)

Conditions	Yield
With ethanol; copper(II) sulfate

ethylmagnesium iodide (10467-10-4) + 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) → N-(4-chlorophenyl)cyanamide (13463-94-0) + N-(4-chloro-phenyl)-N'-propionimidoyl-guanidine

Conditions	Yield
With diethyl ether

ethylmagnesium iodide (10467-10-4) + 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) → N-(4-chloro-phenyl)-N'-propionyl-guanidine

Conditions	Yield
With diethyl ether anschliessend mit wss.Salzsaeure;

methyl magnesium iodide (917-64-6) + 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) → N-(4-chlorophenyl)cyanamide (13463-94-0) + N-acetimidoyl-N'-(4-chloro-phenyl)-guanidine

Conditions	Yield
With diethyl ether

8-amino-6-chloroquinoline (5470-75-7) + 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) → 1-(6-chloro-[8]quinolyl)-5-(4-chloro-phenyl)-biguanide

Conditions	Yield
With hydrogenchloride

ethanol (64-17-5) + 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) → O-ethyl-N-(4-chloro-phenylcarbamimidoyl)-isourea (69232-13-9)

Conditions	Yield
With hydrogenchloride

N-methylpropan-2-amine (4747-21-1) + 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) → 5-(4-chloro-phenyl)-1-isopropyl-1-methyl-biguanide (6712-59-0)

Conditions	Yield
With ethanol; copper(II) sulfate

N-methyl-N-(2-methoxyethyl)amine (38256-93-8) + 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) → 5-(4-chloro-phenyl)-1-(2-methoxy-ethyl)-1-methyl-biguanide

Conditions	Yield
With ethanol; copper(II) sulfate

N,N,N'-triethylethanediamine (105-04-4) + 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) → 1-ethyl-5-(4-chloro-phenyl)-1-(2-diethylamino-ethyl)-biguanide

Conditions	Yield
With ethanol; copper(II) sulfate

methyl-n-propylamine (627-35-0) + 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) → 5-(4-chloro-phenyl)-1-methyl-1-propyl-biguanide

Conditions	Yield
With ethanol; copper(II) sulfate

1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) + 2-METHYLCYCLOHEXYLAMINE (7003-32-9) → 1-(4-chloro-phenyl)-5-(2-methyl-cyclohexyl)-biguanide

1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) + 3-methylcyclohexan-1-amine (6850-35-7) → 1-(4-chloro-phenyl)-5-(3-methyl-cyclohexyl)-biguanide

1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) + isobutylmagnesium bromide (926-62-5) → N-(4-chlorophenyl)cyanamide (13463-94-0) + N-(4-chloro-phenyl)-N'-isovalerimidoyl-guanidine

Conditions	Yield
With diethyl ether

1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) + ethylmagnesium bromide (925-90-6) → N-(4-chlorophenyl)cyanamide (13463-94-0) + N-(4-chloro-phenyl)-N'-propionimidoyl-guanidine

Conditions	Yield
With diethyl ether

1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) + isopropylmagnesium bromide (920-39-8) → N-(4-chlorophenyl)cyanamide (13463-94-0) + N-(4-chloro-phenyl)-N'-isobutyrimidoyl-guanidine

Conditions	Yield
With diethyl ether

1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) + N-methoxylamine hydrochloride (593-56-6) → 1-(4-chloro-phenyl)-5-methoxy-biguanide

Conditions	Yield
With potassium hydroxide; copper(II) sulfate

1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) + aniline hydrochloride (142-04-1) → 1-(4-chloro-phenyl)-5-phenyl-biguanide (66491-64-3)

Conditions	Yield
With 1,4-dioxane

1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) + N-isopropylaniline hydrochloride (23576-78-5) → 5-(4-chloro-phenyl)-1-isopropyl-1-phenyl-biguanide

Upstream product

• 3713-20-0 N-(4-chloro-phenylazo)-N'-cyano-guanidine 
• 156-62-7 calcium cyanamide 
• 506-77-4 cyanogen chloride 
• 127099-85-8 dicyandiamide 
• 20265-96-7 p-chloroaniline hydrochloride 
• 106-47-8 4-chloro-aniline 
• 10191-60-3 dimethyl N-cyanodithioiminocarbonate 
• 1934-75-4 sodium dicyanamide 
• 15760-26-6 3-cyano-2-methylisothiourea 
• 5304-59-6 4-chlorophenylbiguanide 

Downstream Products

• 13463-94-0 N-(4-chlorophenyl)cyanamide 
• 6712-59-0 5-(4-chloro-phenyl)-1-isopropyl-1-methyl-biguanide 
• 75950-43-5 N¹-(p-Chlorophenyl)-N⁵-n-amylbiguanide 
• 13590-88-0 1,5-bis-(4-chloro-phenyl)-biguanide 
• 7539-37-9 N,N'-dibenzoyl-N''-(4-chloro-phenyl)-guanidine 
• 85125-51-5 (4-chloro-phenylcarbamimidoyl)-urea 
• 14294-16-7 (4-chloro-phenylcarbamimidoyl)-thiourea 
• 80309-99-5 1-p-chlorophenyl 2,4-dithiobiuret 
• 109867-15-4 5,5'-bis-(4-chloro-phenyl)-1,1'-p-phenylene-bis-biguanide; dihydrochloride 
• 55-56-1 chlorhexidine 
• 500-92-5 proguanil 

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