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[ CAS No. 16024-82-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 16024-82-1
Chemical Structure| 16024-82-1
Chemical Structure| 16024-82-1
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Product Details of [ 16024-82-1 ]

CAS No. :16024-82-1 MDL No. :MFCD00041062
Formula : C9H7NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :UNXVHBOJSCWVCD-UHFFFAOYSA-N
M.W : 193.22 Pubchem ID :85243
Synonyms :

Calculated chemistry of [ 16024-82-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.11
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 52.41
TPSA : 70.75 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.39
Log Po/w (XLOGP3) : 3.41
Log Po/w (WLOGP) : 2.21
Log Po/w (MLOGP) : 3.05
Log Po/w (SILICOS-IT) : 3.34
Consensus Log Po/w : 2.88

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.33
Solubility : 0.0904 mg/ml ; 0.000468 mol/l
Class : Soluble
Log S (Ali) : -4.58
Solubility : 0.00514 mg/ml ; 0.0000266 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -2.67
Solubility : 0.409 mg/ml ; 0.00212 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.95

Safety of [ 16024-82-1 ]

Signal Word:Danger Class:8,6.1
Precautionary Statements:P260-P264-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P311-P321-P363-P403+P233-P405-P501 UN#:2922
Hazard Statements:H314-H331-H302+H312 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 16024-82-1 ]

* 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 [ 16024-82-1 ]

[ 16024-82-1 ] Synthesis Path-Downstream   1~21

  • 2
  • [ 16024-82-1 ]
  • [ 765-30-0 ]
  • [ 146381-56-8 ]
YieldReaction ConditionsOperation in experiment
In diethyl ether for 5h;
  • 3
  • [ 13754-19-3 ]
  • [ 16024-82-1 ]
  • 3-(4-amino-pyrimidin-5-yl)-2-thioxo-2,3-dihydro-1H-quinazolin-4-one [ No CAS ]
  • 4
  • [ 16024-82-1 ]
  • [ 56-06-4 ]
  • 2,6-bis(4-oxo-2-thioxo-1,2-dihydro-quinazolin-3-yl)-4-hydroxy-pyrimidine [ No CAS ]
  • 5
  • [ 16024-82-1 ]
  • [ 371-40-4 ]
  • [ 1547-15-5 ]
YieldReaction ConditionsOperation in experiment
80% With triethylamine In 1,4-dioxane for 10h; Heating;
  • 6
  • [ 16024-82-1 ]
  • [ 1547-15-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 85 percent / toluene / 4 h / Heating 2: dimethylformamide / Heating
  • 7
  • [ 16024-82-1 ]
  • [ 329080-15-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 57 percent / SnCl4 / 16 h / 20 °C 2: 100 percent / hydrazine / 0.5 h / Heating
  • 8
  • [ 16024-82-1 ]
  • [ 19062-39-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 79 percent / 16 h / Heating 2: 100 percent / hydrazine / ethanol / 3 h / Heating
Multi-step reaction with 3 steps 1: 79 percent / 16 h / Heating 2: 93 percent / hydrazine / ethanol / 96 h / Ambient temperature 3: 53 percent / hydrazine / ethanol / 2.5 h / Heating
  • 9
  • [ 16024-82-1 ]
  • [ 60421-23-0 ]
  • [ 1033693-52-5 ]
YieldReaction ConditionsOperation in experiment
64% With triethylamine; In methanol; at 20℃; for 20h; EXAMPLE A1; 1'-[4-(4-methylpiperazin-1-yl)benzyl]-2'H-spiro[cyclopentane-1,3'-imidazo[2,1-b]quinazoline]-2',5'(1'H)-dione hydrochloride Stage 1: methyl 1-(4-oxo-2-thioxo-1,4-dihydroquinazolin-3(2H)-yl) cyclopentane carboxylateA mixture of <strong>[60421-23-0]methyl 1-aminocyclopentanecarboxylate hydrochloride</strong> (1 g), methyl 2-isothiocyanatobenzoate (1.18 g) and triethylamine (15 mL) in methanol (60 ml) is stirred at ambient temperature for 20 hours then concentrated under reduced pressure at 40 C. Dichloromethane and water are added to the solid obtained. After decantation and extractions, the combined organic phases are washed with salt water, dried over Na2SO4 then concentrated under reduced pressure at 40 C. Purification by flash chromatography on silica gel (eluent: heptane/ethyl acetate 7:3 to 6:4) produces the expected compound in the form of powder (1.08 g, 64% yield).MS/LC: calculated MM=304.4; m/z=305.2 (MH+)NMR (1H, 400 MHz, DMSO-d6): delta 1.76-1.95 (m, 6H), 2.07 (m, 2H), 3.73 (s, 3H), 7.42 (AB, 1H), 7.60 (m, 1H), 7.74 (m, 1H), 7.99 (AB, 1H), 10.8 (s, 1H).
  • 10
  • [ 16024-82-1 ]
  • [ 144-80-9 ]
  • [ 1221119-39-6 ]
  • 11
  • [ 16024-82-1 ]
  • [ 51940-44-4 ]
  • [ 1206482-71-4 ]
YieldReaction ConditionsOperation in experiment
59% With triethylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
  • 12
  • [ 127-79-7 ]
  • [ 16024-82-1 ]
  • [ 1429294-11-0 ]
  • 13
  • [ 16024-82-1 ]
  • [ 526-08-9 ]
  • methyl 2-(3-(4-(N-(1-phenyl-1H-pyrazol-5-yl)sulfamoyl)phenyl)thioureido)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% In ethanol; at 20℃; for 5.0h; A mixtureof compound 2 (1.93 g, 0.01 mole) and 4-amino-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide (3.14 g, 0.01 mole) in absolute ethanol (30 mL) was stirred at room temperature for 5 h. The reaction mixture was poured onto ice water and the solid obtained was recrystallized from dioxane to give 3. Yield% 88; m.p. 322.9 C; IR (KBr, nmax, Cm-1): 3448, 3275(NH),3039 (CH arom.), 2977, 2863 (CH aliph.), 1662 (C=O), 1620(C=N), 1342, 1168 (SO2), 1261 (C=S). 1H NMR spectrum in(DMSO-d6): 4.21 [s, 3H, OCH3], 6.60, 7.64 [2d, 2H, 2CHpyrazole, J = 7.33 Hz], 7.08- 8.12 [m, 13H, Ar-H], 11.46 [s,1H, SO2NH, D2O-exchangeable], 12.95 [s, 2H, 2NH, D2O exchangeable].13C NMR spectrum (in DMSO-d6): 52.4, 95.6,121.3 (2), 121.8, 127.9 (2), 128.5 (2), 129.0 (2), 131.4, 132.6,134.3, 137.8, 139.6, 141.2, 141.8, 144.9, 168.1, 181.2. Anal.Calc. for C24H21N5O4S2 (508): C, 56.79; H, 4.17; N, 13.80;found: C, 56.42; H, 4.34; N, 13.49.
  • 14
  • [ 16024-82-1 ]
  • [ 526-08-9 ]
  • 4-(4-oxo-2-thioxo-1,2-dihydroquinazolin-3(4H)-yl)-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With triethylamine; In ethanol; for 18.0h;Reflux; A mixture of compound 2 (1.93 g, 0.01 mole) and 4-amino-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide (3.14 g, 0.01 mole) in absolute ethanol (30 mL) containing a catalytic amount of triethylamine was refluxed for 18 h. The reaction mixture was cooled and poured onto ice water and the solid obtained was recrystallized from dioxane to give 4. Yield % 90; m.p. 300.4 C; IR (KBr, nmax, Cm-1): 3307, 3210(NH), 3088 (CH arom.), 1688 (C=O), 1610 (C=N), 1365, 1155(SO2), 1272 (C=S). 1H NMR spectrum (in DMSO-d6): 6.44,7.41 [2d, 2H, 2CH pyrazole, J = 6.97 Hz], 7.05-8.23 [m, 13H,Ar-H], 9.35 [s, 1H, NH, D2O-exchangeable], 11.44 [s, 1H,SO2NH, D2O-exchangeable]. 13C NMR spectrum (in DMSOd6):91.7, 119.8 (2), 120.6 (2), 122.7, 124.6, 125.1, 126.8 (2),127.6, 127.9, 128.5 (2), 130.6, 134.1, 134.7, 140.4, 141.3,141.9, 144.8, 162.7, 187.3. Anal. Calc. for C23H17N5O3S2 (476):C, 58.09; H, 3.60; N, 14.73; found: C, 58.32; H, 3.31; N, 14.51.
  • 15
  • [ 16024-82-1 ]
  • [ 122-11-2 ]
  • [ 1675217-77-2 ]
YieldReaction ConditionsOperation in experiment
84% With triethylamine In ethanol for 15h; Reflux; Synthesis of N-(2,6-dimethoxypyrimidin-4-yl)-4-(4-oxo-2-thioxo-1,2-dihydro-quinazolin-3(4H)-yl)benzenesulfonamide (5) A mixture of compound 2 (1.93 g, 0.01 mole) and 4-amino-N-(3,5-dimethoxy-phenyl)benzenesulfonamide (3.08 g, 0.01 mole) in absolute ethanol (30 mL) containing a catalytic amount of triethylamine was refluxed for 15 h. The reaction mixture was cooled and poured onto ice water and the solid obtained was recrystallized from DMF/ EtOH to give 5. Yield % 84; m.p. 219.1 °C; IR (KBr, nmax, Cm-1): 3216, 3194(NH), 3065 (CH arom.), 1691 (C=O), 1622 (C=N), 1357, 1163(SO2), 1265 (C=S). 1H NMR spectrum (in DMSO-d6): 3.62,3.74 [2s, 6H, 2OCH3], 6.26 [s, 1H, CH pyrimidine], 7.13-8.28[m, 8H, Ar-H], 8.93 [s, 1H, NH, D2O-exchangeable], 10.90[s, 1H, SO2NH, D2O-exchangeable]. 13C NMR spectrum (inDMSO-d6): 56.6 (2), 84.3, 120.8 (2), 122.6, 125.7, 126.3 (2),126.9, 127.8, 129.8, 134.6, 134.9, 138.4, 161.3, 161.7, 163.2,174.1, 187.8. Anal. Calc. for C20H17N5O5S2 (472): C, 50. 95;H, 3.63; N, 14.85; found: C, 50.66; H, 3.29; N, 14.49.
  • 16
  • [ 16024-82-1 ]
  • [ 536-90-3 ]
  • [ 56671-19-3 ]
YieldReaction ConditionsOperation in experiment
91% With triethylamine In 1,4-dioxane at 20℃; for 2h; 3-Phenyl-2-thioxoquinazoline-4-one (10a) General procedure: To a solution of methyl 2-isothiocyanatobenzoate (46.7 mg, 0.242 mmol) and aniline (22.1 μL, 0.242 mmol) in 1,4-dioxane (2.0 mL) was added Et3N (37.4 μL, 0.242 mmol). The mixture was stirred at r.t. for 2 h, and the precipitated white solid was collected by filtration, washed with n-hexane, and recrystallized from CHCl3 and n-hexane to afford the title compound (47.0 mg, 0.185 mmol, 76%) as a white solid.
  • 17
  • [ 16024-82-1 ]
  • [ 7251-09-4 ]
  • 3-(4-cyano-3-methoxyphenyl)-2-thioxoquinazoline-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% With triethylamine; In 1,4-dioxane; at 20℃; for 10h; To a solution of methyl 2-isothiocyanatobenzoate (98.8 mg, 0.511 mmol) and 14b (74.0 mg, 0.499 mmol) in dioxane(2.0 mL) was added Et3N (80 muL, mmol). The mixture was stirred at r.t. for 10 h, and the precipitated white solid was collected by filtration and washed with n-hexane to give the title compound (18.9 mg, 0.0818 mmol, 16%) as a white solid. mp>300C. 1H-NMR (500 MHz, DMSO-d6) delta: 7.98 (1H, dd, J=1.2, 8.0 Hz), 7.88 (1H, d, J=8.1 Hz), 7.83-7.80 (1H, m), 7.47 (1H, d, J=8.0 Hz), 7.39-7.36 (2H, m), 7.12 (1H, dd, J=1.7, 8.0 Hz), 3.89 (3H, s). 13C-NMR (125 MHz, DMSO-d6) delta: 175.30, 161.55, 159.60, 145.42, 139.87, 135.73, 133.91, 127.33, 124.40, 122.48, 116.24, 116.09, 115.94, 113.78, 99.97, 56.63. FAB-MS m/z 310 (MH+). Anal. Calcd for C16H11N3O2S: C, 62.12; H, 3.58; N, 13.58. Found: C, 61.98; H, 3.66; N, 13.47
  • 18
  • [ 16024-82-1 ]
  • [ 95-84-1 ]
  • 9-methyl-12H-benzo[4,5]oxazolo[2,3-b]quinazolin-12-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% Stage #1: methyl 2-isothiocyanatobenzoate; 3-amino-4-hydroxytoluene With potassium carbonate In dimethyl sulfoxide at 25℃; for 0.5h; Green chemistry; Stage #2: With potassium metaperiodate In water; dimethyl sulfoxide at 80℃; Green chemistry; Fused Tetracyclic Quinazolinones 7; General Procedure General procedure: Following the above described general procedure for the synthesis of benzazoles, methyl 2-isothiocyanatobenzoate (2m; 0.0521 g, 0.27mmol) was reacted with amino derivative 1. After completion of thereaction, the mixture was treated with CH2Cl2 (2 mL). The resulting precipitate was filtered, washed with CH2Cl2, and oven-dried at 80 °C.
  • 19
  • [ 16024-82-1 ]
  • [ 63631-09-4 ]
  • N-(2-methoxyphenyl)-5-oxo-1-thioxo-4,5-dihydro-1H-thiazolo[3,4-a]quinazoline-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With sulfur; triethylamine In N,N-dimethyl-formamide at 50℃;
  • 20
  • [ 16024-82-1 ]
  • [ 113604-07-2 ]
  • N-(2,5-dimethoxyphenyl)-5-oxo-1-thioxo-4,5-dihydro-1H-thiazolo[3,4-a]quinazoline-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With sulfur; triethylamine In N,N-dimethyl-formamide at 50℃;
  • 21
  • [ 15386-80-8 ]
  • [ 16024-82-1 ]
  • N-(3,4-dichlorophenyl)-5-oxo-1-thioxo-4,5-dihydro-1H-thiazolo[3,4-a]quinazoline-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With sulfur; triethylamine In N,N-dimethyl-formamide at 50℃;
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