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[ CAS No. 952-23-8 ] {[proInfo.proName]}

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Chemical Structure| 952-23-8
Chemical Structure| 952-23-8
Structure of 952-23-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 952-23-8 ]

CAS No. :952-23-8 MDL No. :MFCD00066867
Formula : C13H12ClN3 Boiling Point : -
Linear Structure Formula :- InChI Key :PBBGTVBGXBUVLT-UHFFFAOYSA-N
M.W : 245.71 Pubchem ID :197873
Synonyms :

Calculated chemistry of [ 952-23-8 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 14
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 75.02
TPSA : 64.93 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.93 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.63
Log Po/w (WLOGP) : 3.37
Log Po/w (MLOGP) : 2.06
Log Po/w (SILICOS-IT) : 2.01
Consensus Log Po/w : 2.01

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.63
Solubility : 0.0576 mg/ml ; 0.000235 mol/l
Class : Soluble
Log S (Ali) : -3.64
Solubility : 0.0558 mg/ml ; 0.000227 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.67
Solubility : 0.00531 mg/ml ; 0.0000216 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.58

Safety of [ 952-23-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 952-23-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 952-23-8 ]

[ 952-23-8 ] Synthesis Path-Downstream   1~41

  • 1
  • [ 952-23-8 ]
  • [ 260-94-6 ]
  • [ 581-29-3 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; phosphoric acid; sodium nitrite 1.) 0 deg C, 1 min, 2.) 0 deg C, 48 h; Yield given. Multistep reaction. Yields of byproduct given;
  • 2
  • [ 952-23-8 ]
  • [ 43129-74-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride at 180 - 190℃; for 44h;
  • 3
  • [ 952-23-8 ]
  • [ 78276-16-1 ]
  • [ 57459-61-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium azide; sodium nitrite 1.) 0 deg C, 1 min, 2.) 0 deg C, 30 min; Yield given. Multistep reaction. Yields of byproduct given;
  • 4
  • [ 952-23-8 ]
  • [ 57459-61-7 ]
YieldReaction ConditionsOperation in experiment
85% With sodium azide; trifluoroacetic acid; sodium nitrite at -5 - 0℃; for 1.25h;
With sodium azide; trifluoroacetic acid; sodium nitrite 1.) 0-5 deg C, 5 min; 2.) 15 min; Yield given. Multistep reaction;
  • 5
  • [ 952-23-8 ]
  • 6-Amino-3-acridin-diazonium-ditetrafluoroborat [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; tetrafluoroboric acid; sodium nitrite 1) H2O, 0 deg C, 30 min, 2) H2O, 0 deg C, 2 h; Yield given. Multistep reaction;
  • 6
  • [ 952-23-8 ]
  • [ 74165-93-8 ]
YieldReaction ConditionsOperation in experiment
98% With iodine; potassium iodide
  • 7
  • [ 952-23-8 ]
  • 3,6-Diamino-4,5-dibrom-acridin [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With N-Bromosuccinimide; acetic acid
YieldReaction ConditionsOperation in experiment
Photochem. Verhalten;
  • 11
  • [ 952-23-8 ]
  • [ 122-51-0 ]
  • 3,6-di-1H-tetrazol-1-yl-acridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With sodium azide In acetic acid at 90℃; for 3h;
  • 12
  • [ 952-23-8 ]
  • 3,6-Diamino-2,4,5,7-tetrabrom-acridin [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 82 percent / N-bromosuccinimide, aq. AcOH 2: 28 percent / N-bromosuccinimide, glacial AcOH / Heating
YieldReaction ConditionsOperation in experiment
3 3,6-Di-(β-D-galactopyranosyl-amino)-acridine EXAMPLE 3 3,6-Di-(β-D-galactopyranosyl-amino)-acridine In a round-bottom flask with a volume of 3 l provided with a reflux condenser and a mixer 60.0 g (0.33 mole) of D-galactose and 36.9 g (0.15 mole) of 3,6-diaminoacridine-hydrochloride are suspended in a mixture of 1350 ml of ethanol and 150 ml of water under heavy stirring.
  • 14
  • [ 50-69-1 ]
  • [ 952-23-8 ]
  • [ 84207-96-5 ]
YieldReaction ConditionsOperation in experiment
2.5 g (52.8%) With hydrogenchloride In water; acetone 7 3,6-Di-(α-D-ribopyranosyl-amino)-acridine EXAMPLE 7 3,6-Di-(α-D-ribopyranosyl-amino)-acridine Under stirring 2.46 g (10-2 mole) of 3,6-diamino-acridine-hydrochloride and 3.3 g (2.2*10-2 mole) of D-ribose are suspended in a mixture of 90 ml acetone and 10 ml of water. 0.5 ml of concentrated hydrochloric acid are added to the suspension heated to 45° C. After 2-3 minutes a clear solution is formed and after further 4-5 minutes the precipitate begins to separate. 25 minutes after the addition of the acid and liquid phase is separated, the precipitate is dissolved in 20 ml of water and the solution is poured into 200 ml of acetone. This reprecipitation is repeated twice. The product is filtered and dried. Yield: 2.5 g (52.8%), melting point: 180°-190° C., [α]D =+141° (c=1.20, dimethylformamide);
  • 15
  • [ 952-23-8 ]
  • [ 10030-85-0 ]
  • [ 84207-95-4 ]
YieldReaction ConditionsOperation in experiment
In ethanol; water; EXAMPLE 6 3,6-Di-(alpha-L-rhamnopyranosyl-amino)-acridine 2.46 g (10-2 mole) of 3,6-diamino-acridine-hydrochloride and 4.0 g (2.2*10-2 mole) of <strong>[10030-85-0]L-rhamnose-monohydrate</strong> are suspended in a mixture of 10 ml of water and 90 ml of ethanol. The reaction mixture is stirred intensively and heated to a temperature of 70 C. After the addition of 0.5 ml or concentrated hydrochloric acid the mixture is stirred at the given temperature for another 90 minutes, while shining, flocculent crystals separate. The mixture is left to stand at room temperature for 12 hours and then it is filtered. 3.6 g (71.8%) of product are obtained.
  • 16
  • [ 248928-58-7 ]
  • [ 960126-09-4 ]
  • [ 960126-21-0 ]
  • [ 960126-13-0 ]
  • [ 960126-17-4 ]
  • [ 952-23-8 ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide; nitric acid; iron(II) sulfate In water at 25℃; Darkness;
  • 17
  • [ 952-23-8 ]
  • [ 170302-06-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetone / 72 h / Reflux 2: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 3: potassium carbonate / acetone / 24 h / Reflux
  • 18
  • [ 952-23-8 ]
  • [ 1401297-95-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetone / 72 h / Reflux 2: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere
  • 19
  • [ 952-23-8 ]
  • [1,3-phenylenebis(methylene)]bis[(6-amino-3-acridinyl)carbamic acid methyl ester] [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetone / 72 h / Reflux 2: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere
  • 20
  • [ 952-23-8 ]
  • [2,6-naphthalenediylbis(methylene)]bis[(6-amino-3-acridinyl)carbamic acid methyl ester] [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetone / 72 h / Reflux 2: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere
  • 21
  • [ 952-23-8 ]
  • [1,3-phenylenebis(methylene)]bis[[6-[(methoxycarbonyl)amino]-3-acridinyl]carbamic acid methyl ester] [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetone / 72 h / Reflux 2: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 3: potassium carbonate / acetone / 24 h / Reflux
  • 22
  • [ 952-23-8 ]
  • [ 173093-92-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: acetone / 72 h / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 2 h
  • 23
  • [ 952-23-8 ]
  • [ 173093-93-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: acetone / 72 h / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 2 h 3.1: potassium carbonate / acetone / 5 h / Reflux
  • 24
  • [ 952-23-8 ]
  • [ 173093-89-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: acetone / 72 h / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 2 h 3.1: potassium carbonate / acetone / 5 h / Reflux 4.1: pyridine; copper(II) acetate monohydrate / methanol / 96 h / 45 °C
  • 25
  • [ 952-23-8 ]
  • [ 173093-95-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: acetone / 72 h / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 2 h 3.1: potassium carbonate / acetone / 5 h / Reflux 4.1: pyridine; copper(II) acetate monohydrate / methanol / 96 h / 45 °C 5.1: sodium hydroxide / N,N-dimethyl-formamide; toluene / 1.5 h / 20 °C
  • 26
  • [ 952-23-8 ]
  • [1,2-phenylenebis(methylene)]bis[(6-amino-3-acridinyl)carbamic acid methyl ester] [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetone / 72 h / Reflux 2: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere
  • 27
  • [ 952-23-8 ]
  • [ 1401297-96-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetone / 72 h / Reflux 2: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 3: potassium carbonate / acetone / 24 h / Reflux
  • 28
  • [ 952-23-8 ]
  • C50H42N6O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: acetone / 72 h / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / acetone / 24 h / Reflux 4.1: sodium hydride / N,N-dimethyl-formamide / 40 °C / Inert atmosphere 4.2: 20 °C / Inert atmosphere
  • 29
  • [ 952-23-8 ]
  • C50H42N6O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: acetone / 72 h / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / acetone / 24 h / Reflux 4.1: sodium hydride / N,N-dimethyl-formamide / 40 °C / Inert atmosphere 4.2: 20 °C / Inert atmosphere
  • 30
  • [ 952-23-8 ]
  • [ 1401298-03-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: acetone / 72 h / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / acetone / 24 h / Reflux 4.1: sodium hydride / N,N-dimethyl-formamide / 40 °C / Inert atmosphere 4.2: 20 °C / Inert atmosphere
  • 31
  • [ 952-23-8 ]
  • [ 79-22-1 ]
  • [ 170302-05-3 ]
YieldReaction ConditionsOperation in experiment
69% Stage #1: proflavine hydrochloride; methyl chloroformate In acetone for 72h; Reflux; Stage #2: With sodium methylate In methanol 2 General information 4.2 (6-Amino-3-acridinyl)carbamic acid methyl ester To a suspension of 3,6-diaminoacridine hydrochloride (3 g, 12.21 mmol) in dry acetone (100 mL), freshly distilled methyl chloroformate (9.4 mL, 122.1 mmol) was added. The reaction mixture was refluxed for 72 h and then concentrated up to dryness. The residue thus obtained was dissolved in methanol and the solution was basified with sodium methoxide in methanol. The crude product obtained after concentrating the solution in vacuo was purified by flash column (Ø=6 cm) chromatography by using acetone-ethyl acetate-triethylamine (5/5/1, v/v/v) as eluent, affording 2.25 g (69%) of product; mp 163-165 °C (hexane-dichloromethane). Found: C, 67.52; H, 4.85; N, 15.91. C15H13N3O2 requires C, 67.41; H, 4.90; N, 15.72; IR (KBr): ν 3334, 3215, 1717, 1645, 1551, 1488, 1462, 1398, 1318 cm-1; 1H NMR (DMSO-d6) δ 10.00 (s, 1H, NH), 8.51 (s, 1H, H-9), 8.06 (d, J=2.1 Hz, 1H, H-4), 7.83 (d, J=9.1 Hz, 1H, H-8), 7.72 (d, J=9.1 Hz, 1H, H-1), 7.41 (dd, J=9.1, 2.1 Hz, 1H, H-7), 6.99 (dd, J=9.1, 2.1 Hz, 1H, H-2), 6.84 (d, J=2.1 Hz, 1H, H-5), 6.22 (br s, 2H, NH2), 3.72 (s, 3H, CO2CH3); 13C NMR (DMSO-d6): δ 154.2, 151.6, 151.1, 149.8, 140.5, 135.0, 129.6, 129.3, 120.7, 120.2, 117.6, 112.4, 103.0, 52.0; MS (EI) (calcd for C15H13N3O2, 267.28) m/z 267 (M+, 82%), 235 (100), 208 (24), 181 (20), 153 (7).
  • 32
  • [ 952-23-8 ]
  • [ 92-62-6 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate In water at 40℃; 1 Synthesis of 3,6-Diamino-4,5-diiodoacridine DDA was synthesized based on a literature procedure (Martin, R. F., Aust. J. Chem., 1979, 32(12), 2637-2646). A round-bottom flask was charged with Proflavine HCl (1.4 g, 5.70 mmol) in water (150 mL). The solution was heated to 40° C. then solid NaHCO3 was added until a pH of 10 was achieved. The suspension was filtered and a yellow solid was isolated. A round-bottom flask was charged with the yellow solid (1.0 g, 4.79 mmol), potassium iodide (1.982 g, 11.946 mmol), Chloramine-T (3.366 g, 11.946 mmol), and dimethylformamide (20 mL) then reacted at ambient conditions for 1 hour. The resulting suspension was poured into water and the product was extracted with 3×50 mL of ethyl acetate. The ethyl acetate fractions were combined, reacted with sodium thiosulfate (25 mg), dried over anhydrous MgSO4, and evaporated using a rotary evaporator. To remove the p-toluene sulfonamide impurity, the resulting solid was dissolved in 250 mL of dichloromethane and excess ptoluenesulfonic acid monohydrate (1.26 g, 7.34 mmol) was added. After one hour of equilibration a dark red solid was isolated (608 mg 28% yield). 1H NMR spectroscopy verified the spectrum of the isolated solid matched the previously reported spectrum for DDA.
  • 33
  • [ 952-23-8 ]
  • [ 90-02-8 ]
  • C27H19N3O2*ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With triethylamine In ethanol at 79℃; for 8h;
  • 34
  • [ 952-23-8 ]
  • 2C27H17N3O2(2-)*2Co(2+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / ethanol / 8 h / 79 °C 2: triethylamine / acetonitrile / 24 h
  • 35
  • [ 952-23-8 ]
  • 3,6-(chloroethylamino)acridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 6 h / 100 °C 2.1: borane-THF / tetrahydrofuran / 0 - 75 °C / Inert atmosphere 2.2: 75 °C / Inert atmosphere
  • 36
  • [ 952-23-8 ]
  • N,N’-(2-chloroacetamidyl)-N,N’-(ethoxymethyl)-3,6-acridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / 72 h / Inert atmosphere 2: phosphorus pentoxide / 5.5 h / 100 °C / Inert atmosphere
  • 37
  • [ 952-23-8 ]
  • C31H23N11O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 6 h / 100 °C 2: sodium azide; copper(ll) sulfate pentahydrate; sodium L-ascorbate / N,N-dimethyl-formamide; water / 5 h / 20 °C / Inert atmosphere
  • 38
  • [ 952-23-8 ]
  • C37H35N11O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / 72 h / Inert atmosphere 2: sodium azide; copper(ll) sulfate pentahydrate; sodium L-ascorbate / N,N-dimethyl-formamide; water / 5 h / 20 °C / Inert atmosphere
  • 39
  • [ 952-23-8 ]
  • C31H27N11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 6 h / 100 °C 2.1: borane-THF / tetrahydrofuran / 0 - 75 °C / Inert atmosphere 2.2: 75 °C / Inert atmosphere 3.1: sodium azide; copper(ll) sulfate pentahydrate; sodium L-ascorbate / N,N-dimethyl-formamide; water / 80 °C / Inert atmosphere
  • 40
  • [ 952-23-8 ]
  • [ 625-45-6 ]
  • 3,6-(methoxyethylamino)acridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With sodium tetrahydroborate for 72h; Inert atmosphere;
  • 41
  • [ 952-23-8 ]
  • [ 79-04-9 ]
  • [ 51462-38-5 ]
YieldReaction ConditionsOperation in experiment
100% at 100℃; for 6h;
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