6,9-Dichloro-2-methoxyacridine supplier

Name
6,9-Dichloro-2-methoxyacridine
EINECS 201-666-7
CAS No. 86-38-4
Article Data22
CAS DataBase
Density 1.399 g/cm³
Solubility Insoluble in water.
Melting Point 163-165 °C
Formula C₁₄H₉Cl₂NO
Boiling Point 444.3 °C at 760 mmHg
Molecular Weight 278.138
Flash Point 222.5 °C
Transport Information
Appearance
Safety 26-37/39
Risk Codes 36/37/38-42/43
Molecular Structure
Hazard Symbols Xn
Synonyms Halocrine;NSC 2095;NSC 2951;2-Methoxy-6,9-dichloroacridine;3,9-Dichloro-7-methoxyacridine;Halocrin;
PSA 22.12000
LogP 4.70340

Synthetic route

: 91-38-3
4-chloro-2-(4-methoxyphenylamino)benzoic acid

: 86-38-4
6,9-dichloro-2-methoxyacridine

Conditions

Conditions	Yield
Stage #1: 4-chloro-2-(4-methoxyphenylamino)benzoic acid With trichlorophosphate at 130℃; for 3h; Stage #2: With ammonia In chloroform; water Cooling with ice;	99%
With trichlorophosphate at 130℃; for 3h;	99%
With trichlorophosphate for 6h; Heating;	77%

: 13161-87-0
6-chloro-2-methoxyacridone

: 86-38-4
6,9-dichloro-2-methoxyacridine

Conditions

Conditions	Yield
With phosphorus pentachloride
With trichlorophosphate
With phosphorus pentachloride
With trichlorophosphate

: 32082-99-8
methyl 4-chloro-2-(4-methoxyphenyl)aminobenzoate

: 86-38-4
6,9-dichloro-2-methoxyacridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Ba(OH)2*8H2O / methanol / 2 h / 80 °C 2: POCl3 View Scheme

: 104-94-9
4-methoxy-aniline

4-[Ph2(AcO)2Bi]-C6H4-OCH2-polystyrene cross-linked with divinylbenzene: 4-[Ph2(AcO)2Bi]-C6H4-OCH2-polystyrene cross-linked with divinylbenzene

: 86-38-4
6,9-dichloro-2-methoxyacridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: BINAP / Pd(OAc)2 2: Ba(OH)2*8H2O / methanol / 2 h / 80 °C 3: POCl3 View Scheme
Multi-step reaction with 2 steps 1: 58 percent / K2CO3; Cu; pyridine / pentan-1-ol / 5 h / Heating 2: 77 percent / POCl3 / 6 h / Heating View Scheme

: 212892-02-9
methyl 4-chloro-2-(((trifluoromethyl)sulfonyl)oxy)benzoate

: 86-38-4
6,9-dichloro-2-methoxyacridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: BINAP / Pd(OAc)2 2: Ba(OH)2*8H2O / methanol / 2 h / 80 °C 3: POCl3 View Scheme

: 50-84-0
2,4 dichlorobenzoic acid

: 86-38-4
6,9-dichloro-2-methoxyacridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 58 percent / K2CO3; Cu; pyridine / pentan-1-ol / 5 h / Heating 2: 77 percent / POCl3 / 6 h / Heating View Scheme
Multi-step reaction with 2 steps 1.1: copper; potassium carbonate / N,N-dimethyl-formamide / 130 °C 2.1: trichlorophosphate / 3 h / 130 °C 2.2: Cooling with ice View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate; copper / N,N-dimethyl-formamide / 130 °C 2: trichlorophosphate / 3 h / 130 °C View Scheme

: 104-94-9
4-methoxy-aniline

: 86-38-4
6,9-dichloro-2-methoxyacridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate; copper / N,N-dimethyl-formamide / 130 °C 2: trichlorophosphate / 3 h / 130 °C View Scheme
Multi-step reaction with 2 steps 1: copper; potassium carbonate / 130 °C 2: trichlorophosphate / 3 h / 130 °C View Scheme
Multi-step reaction with 2 steps 1: copper; potassium carbonate / N,N-dimethyl-formamide / Heating 2: trichlorophosphate / 0.25 h / 140 °C / Microwave irradiation View Scheme

: 74-11-3
para-chlorobenzoic acid

: 86-38-4
6,9-dichloro-2-methoxyacridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium iodide; copper; potassium carbonate / N,N-dimethyl-formamide / Reflux 2: trichlorophosphate / 135 °C View Scheme

: 288-32-4
1H-imidazole

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 6-chloro-9-(1H-imidazol-1-yl)-2-methoxy acridine

Conditions

Conditions	Yield
With indium(III) chloride In acetonitrile at 120℃; for 1h; Microwave irradiation; regioselective reaction;	100%
In toluene Reflux;	79%
With phenol at 120℃; for 0.5h;	64%

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 100-46-9
benzylamine

: 6-chloro-2-methoxy-N-benzylacridin-9-amine

Conditions

Conditions	Yield
With indium(III) chloride In acetonitrile at 120℃; for 1h; Microwave irradiation; regioselective reaction;	100%
With phenol at 120℃; for 0.5h;	98%
Stage #1: benzylamine With potassium carbonate In ethanol at 20℃; for 0.75h; Stage #2: 6,9-dichloro-2-methoxyacridine With potassium iodide In ethanol Reflux;	82%

: 110-91-8
morpholine

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 6-chloro-2-methoxy-9-morpholinoacridinium chloride

Conditions

Conditions	Yield
With indium(III) chloride In acetonitrile at 120℃; for 0.5h; Microwave irradiation; regioselective reaction;	100%

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 98-80-6
phenylboronic acid

: C26H19NO

Conditions

Conditions	Yield
With potassium phosphate In toluene at 100℃; for 24h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;	99%

: 124-09-4
1,6-Hexanediamine

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 121714-48-5
N1-(6-chloro-2-methoxyacridin-9-yl)hexane-1,6-diamine

Conditions

Conditions	Yield
	98%
at 80℃; for 1h;	74%
Substitution;

: 111-26-2
hexan-1-amine

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 77420-97-4
6-chloro-N-hexyl-2-methoxyacridin-9-amine

Conditions

Conditions	Yield
With indium(III) chloride In acetonitrile at 120℃; for 0.5h; Microwave irradiation; regioselective reaction;	98%
With phenol at 120℃; for 0.5h;	88%

: 140-87-4
Cyanoacetohydrazide

: 86-38-4
6,9-dichloro-2-methoxyacridine

: N'-(6-chloro-2-methoxyacridin-9-yl)-2-cyanoacetohydrazide

Conditions

Conditions	Yield
In ethanol at 70℃; for 4h;	98%

: 110-91-8
morpholine

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 72410-84-5
4-(6-chloro-2-methoxyacridin-9-yl)morpholine

Conditions

Conditions	Yield
With phenol at 120℃; for 0.75h;	96%

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 22483-09-6
2,2-dimethoxyethylamine

: 6-chloro-2-methoxy-9-(2,2-dimethoxyethyl)aminoacridine

Conditions

Conditions	Yield
With phenol at 80℃; for 1h;	96%

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 591-27-5
m-Hydroxyaniline

: 1312923-73-1
3-(6-chloro-2-methoxyacridin-9-ylamino)phenol

Conditions

Conditions	Yield
In ethanol	96%
With hydrogenchloride In ethanol; water for 24h; Reflux;	96%
With hydrogenchloride In ethanol; chloroform; water at 20℃;	71%

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 873-74-5
4-Aminobenzonitrile

: 855195-77-6
4-(6-chloro-2-methoxy-acridin-9-ylamino)-benzonitrile

Conditions

Conditions	Yield
In ethanol	96%
With hydrogenchloride In ethanol; water for 24h; Reflux;	96%

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 62-53-3
aniline

: 6-chloro-2-methoxy-N-phenylacridin-9-amine

Conditions

Conditions	Yield
With phenol at 120℃; for 0.5h; Microwave irradiation;	95%
With phenol at 100℃;
Stage #1: 6,9-dichloro-2-methoxyacridine; aniline With hydrogenchloride In ethanol; water for 24h; Reflux; Stage #2: In ethanol; water Alkaline conditions;

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 109-76-2
Trimethylenediamine

: 85363-11-7
N1-(6-chloro-2-methoxy-acridin-9-yl)-propane-1,3-diamine

Conditions

Conditions	Yield
at 70℃; for 1h; Inert atmosphere;	95%
With triethylamine In neat (no solvent)	85%
With triethylamine In neat (no solvent) Heating;	85%

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 3-amino-4-methoxy-6-methanesulfonamidobenzoic acid methyl ester hydrochloride

: 716312-65-1
5-(6-Chloro-2-methoxy-acridin-9-ylamino)-2-methanesulfonylamino-4-methoxy-benzoic acid methyl ester

Conditions

Conditions	Yield
In methanol Ambient temperature;	95%

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 3-amino-4-methoxy-benzoic acid methyl ester; hydrochloride

: 3-(6-Chloro-2-methoxy-acridin-9-ylamino)-4-methoxy-benzoic acid methyl ester; hydrochloride

Conditions

Conditions	Yield
In methanol Ambient temperature;	95%

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 191214-93-4
2-hydroxy-6,9-dichloroacridine

Conditions

Conditions	Yield
With boron tribromide In dichloromethane at -78 - 20℃; for 8h; Inert atmosphere;	95%
With boron tribromide In dichloromethane at 20℃; for 8h; Inert atmosphere;

: 4651-91-6
3-cyano-2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 2-(6-chloro-2-methoxy-acridin-9-ylamino)-4,5,6,7-tetrahydro-benzo[b]-thiophene-3-carbonitrile

Conditions

Conditions	Yield
With acetic acid In ethanol for 4h;	94.9%

: 23917-22-8
2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carbonitrile

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 2-((6-chloro-2-methoxy-acridin-9-yl)amino)-5,6,7,8-tetrahydro-4H-cyclohepta[b]-thiophene-3-carbonitrile

Conditions

Conditions	Yield
With acetic acid In ethanol for 4h;	94.3%

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 99-98-9
4-amino-N,N-dimethylaniline

: N1-(6-chloro-2-methoxyacridin-9-yl)-N4,N4-dimethylbenzene-1,4-diamine

Conditions

Conditions	Yield
With phenol at 120℃; for 0.75h;	94%
With hydrogenchloride In ethanol for 24h; Heating;	70%
With phenol

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 110-60-1
1,4-diaminobutane

: 7657-92-3
N1-(6-chloro-2-methoxyacridin-9-yl)butane-1,4-diamine

Conditions

Conditions	Yield
at 80℃; for 4h;	93%
at 70℃; for 1h;	58%
at 80℃; for 2h;

: 50541-93-0
4-amino-1-benzylpiperidine

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 1062073-61-3
N-(1-benzylpiperidin-4-yl)-6-chloro-2-methoxyacridin-9-amine

Conditions

Conditions	Yield
With phenol at 120℃; for 0.75h;	93%
Stage #1: 6,9-dichloro-2-methoxyacridine With phenol at 100℃; for 1h; Stage #2: 4-amino-1-benzylpiperidine at 120℃; Further stages.;	48%
Stage #1: 4-amino-1-benzylpiperidine; 6,9-dichloro-2-methoxyacridine In phenol at 120℃; for 4h; Stage #2: With sodium hydroxide In phenol

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 95-54-5
1,2-diamino-benzene

: 1610849-74-5
6-chloro-2-methoxy-9-(2-aminoanilino)acridine hydrochloride

Conditions

Conditions	Yield
In methanol at 110℃; for 0.166667h; Microwave irradiation;	93%

: 120-72-9
indole

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 6-chloro-9-(1H-indol-3-yl)-2-methoxyacridinium chloride

Conditions

Conditions	Yield
With indium(III) chloride In acetonitrile at 120℃; for 2h; Microwave irradiation; regioselective reaction;	93%

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 107-15-3
ethylenediamine

: 14446-60-7
N1-(6-chloro-2-methoxyacridin-9-yl)ethane-1,2-diamine

Conditions

Conditions	Yield
at 80℃; for 4h;	92%
at 70℃; for 1h; Inert atmosphere;	89%
With 4-methyl-morpholine at 20℃; for 20h; Reflux;	88%

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 98570-61-7
(6-chloro-2-methoxy-acridin-9-yl)-hydrazine

Conditions

Conditions	Yield
With hydrazine hydrate at 20 - 150℃; for 0.0833333h; microwave irradiation in sealed tube;	92%
With ethanol; hydrazine hydrate
With hydrazine hydrate

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 371-40-4
4-fluoroaniline

: 1594853-59-4
6-chloro-N-(4-fluorophenyl)-2-methoxyacridin-9-amine

Conditions

Conditions	Yield
In ethanol	92%
With hydrogenchloride In ethanol; water for 24h; Reflux;	92%

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 106461-34-1
1-(4-chlorophenethyl)piperidin-4-amine

: N-(1-(4-chlorophenethyl)piperidin-4-yl)-6-chloro-2-methoxyacridin-9-amine dihydrochloride

Conditions

Conditions	Yield
In phenol at 120℃; for 4h;	92%

: 1076-38-6
4-hydroxy[1]benzopyran-2-one

: 86-38-4
6,9-dichloro-2-methoxyacridine

: 6-chloro-9-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-methoxyacridinium chloride

Conditions

Conditions	Yield
With indium(III) chloride In acetonitrile at 140℃; for 1h; Microwave irradiation; regioselective reaction;	92%

6,9-Dichloro-2-methoxyacridine Specification

This chemical is called 6,9-Dichloro-2-methoxyacridine, and it can also be named as Acridine, 6,9-dichloro-2-methoxy-. With the molecular formula of C₁₄H₉Cl₂NO, its molecular weight is 278.13. The CAS registry number of this chemical is 86-38-4.

Other characteristics of the 6,9-Dichloro-2-methoxyacridine can be summarised as followings: (1)ACD/LogP: 4.43; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.43; (4)ACD/LogD (pH 7.4): 4.43; (5)ACD/BCF (pH 5.5): 1366.84; (6)ACD/BCF (pH 7.4): 1372.25; (7)ACD/KOC (pH 5.5): 6104.52; (8)ACD/KOC (pH 7.4): 6128.68; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 22.12 Å²; (13)Index of Refraction: 1.696; (14)Molar Refractivity: 76.49 cm³; (15)Molar Volume: 198.7 cm³; (16)Polarizability: 30.32×10^-24cm³; (17)Surface Tension: 53.4 dyne/cm; (18)Density: 1.399 g/cm³; (19)Flash Point: 222.5 °C; (20)Enthalpy of Vaporization: 67.51 kJ/mol; (21)Boiling Point: 444.3 °C at 760 mmHg; (22)Vapour Pressure: 1.13E-07 mmHg at 25°C.

Production method of this chemical: The 6,9-Dichloro-2-methoxyacridine could be obtained by the reactant of 4-chloro-2-(4-methoxy-anilino)-benzoic acid. This reaction needs the reagent of POCl₃. The yield is 51 %. In addition, this reaction should be taken for 2 hours. The other condition is heating.

Uses of this chemical: The 6-chloro-2-methoxy-acridin-9-ylamine could be obtained by the reactant of 6,9-Dichloro-2-methoxyacridine. This reaction needs the reagents of (NH₄)₂CO₃, phenol. The yield is 70 %. This reaction should be taken for 45 minutes at the temperature of 120 °C.

When you are using this chemical, please be cautious about it as the following: This chemical is irritating to eyes, respiratory system and skin. It may cause sensitization by inhalation and skin contact. Wear suitable gloves and eye/face protection when you use it. In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1.SMILES: Clc1c3c(nc2c1ccc(Cl)c2)ccc(OC)c3
2.InChI: InChI=1/C14H9Cl2NO/c1-18-9-3-5-12-11(7-9)14(16)10-4-2-8(15)6-13(10)17-12/h2-7H,1H3
3.InChIKey: RYRNQWYNHLLOGX-UHFFFAOYAB

Product Name

6,9-Dichloro-2-methoxyacridine

Synthetic route

6,9-Dichloro-2-methoxyacridine Specification

Related Products

Hot Products