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Cas Database |
| Name |
6,9-Dichloro-2-methoxyacridine |
EINECS | 201-666-7 |
| CAS No. | 86-38-4 | Density | 1.399 g/cm3 |
| PSA | 22.12000 | LogP | 4.70340 |
| 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 | N/A | Appearance | N/A |
| 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; |
Article Data | 22 |
6,9-Dichloro-2-methoxyacridine Synthetic route
| 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 | 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 | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: Ba(OH)2*8H2O / methanol / 2 h / 80 °C 2: POCl3 View Scheme |
| 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 | 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 |
| 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 |
| 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 |
| 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 |
| 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% |
| 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% |
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.
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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.
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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
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