Home Cart 0 Sign in  

[ CAS No. 99614-64-9 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
Chemical Structure| 99614-64-9
Chemical Structure| 99614-64-9
Structure of 99614-64-9 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 99614-64-9 ]

Related Doc. of [ 99614-64-9 ]

Alternatived Products of [ 99614-64-9 ]

Product Details of [ 99614-64-9 ]

CAS No. :99614-64-9 MDL No. :MFCD08063682
Formula : C14H13NO Boiling Point : -
Linear Structure Formula :- InChI Key :AGQJDIDJKSFVTC-UHFFFAOYSA-N
M.W : 211.26 Pubchem ID :11790505
Synonyms :

Calculated chemistry of [ 99614-64-9 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.21
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 65.39
TPSA : 22.0 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.66 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.32
Log Po/w (XLOGP3) : 2.71
Log Po/w (WLOGP) : 2.86
Log Po/w (MLOGP) : 2.21
Log Po/w (SILICOS-IT) : 3.36
Consensus Log Po/w : 2.69

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.27
Solubility : 0.113 mg/ml ; 0.000533 mol/l
Class : Soluble
Log S (Ali) : -2.83
Solubility : 0.316 mg/ml ; 0.00149 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.24
Solubility : 0.0123 mg/ml ; 0.0000581 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.42

Safety of [ 99614-64-9 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P280 UN#:2811
Hazard Statements:H301-H317 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 99614-64-9 ]

* 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.

  • Upstream synthesis route of [ 99614-64-9 ]
  • Downstream synthetic route of [ 99614-64-9 ]

[ 99614-64-9 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 60498-72-8 ]
  • [ 99614-64-9 ]
  • [ 99614-02-5 ]
YieldReaction ConditionsOperation in experiment
98% for 2.16667 h; Heating / reflux Example 17 5 g of 1, 2,3, 9-tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one prepared in any one of Examples 1 to 7 and 11 g of 2-methyl-l-trimethylsilyl imidazole were suspended in 35 ml of acetonitrile. The solution of 6.2 g of tetra-n- butylammonium fluoride hydrate in 15 ml of acetonitrile was added dropwise for 10 min under reflux, and then the reaction mixture was stirred for 2 hours. After cooling to ambient temperature, the reaction solvent was distilled off. 100 ml of water was added to the residue, and then stirred for 30 min. The resulting solid was filtered and washed with 100 ml of water to give 6.61 g of the title compound as a white solid (yield 98percent).; Example 20 5 g of 1, 2,3, 9-tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one prepared in any one of Examples 1 to 7 and 22 g of 2-methyl-l-trimethylsilyl imidazole were suspended in 35 ml of acetonitrile. The solution of 6.2 g of tetra-n- butylammonium fluoride hydrate in 15 ml of acetonitrile was added dropwise for 10 min under reflux, and then the reaction mixture was stirred for 2 hours. After cooling to ambient temperature, the reaction solvent was distilled off. 100 ml of water was added to the residue, and then stirred for 30 min. The resulting solid was filtered and washed with 100 ml of water to give 6.75 g of the title compound as a white solid (yield 100percent).
96.7% for 2.16667 h; Heating / reflux Example 19 The same procedures as described in Example 17 were repeated, except that ethyl acetate was employed instead of acetonitrile, to give 6.72 g of the title compound (yield 96.7percent).
96.1% at 80℃; for 2 h; Example 21 To the mixture of 5 g of 1, 2,3, 9-tetrahydro-9-methyl-3-methylene-4H- carbazol-4-one prepared in any one of Examples 1 to 7 and 22 g of 2-methyl-1- trimethylsilyl imidazole was added 6.2 g of tetra-n-butylammonium fluoride hydrate at 80 °C, and then the reaction mixture was stirred for 2 hours. After cooling to ambient temperature, 100 ml of water was added to the reaction mixture, and then stirred for 30 min. The resulting solid was filtered and washed with 100 ml of water to give 6.48 g of the title compound as a white solid (yield 96. 1percent).
94.5% for 2.16667 h; Heating / reflux Example 18 The same procedures as described in Example 17 were repeated, except that tetrahydrofuran was employed instead of acetonitrile, to give 6.57 g of the title compound (yield 94.5percent).
92% at 80℃; for 2.16667 h; Heating / reflux Example 15 The mixture of 5 g of 1, 2,3, 9-tetrahydro-9-methyl-3-methylene-4H- carbazol-4-one prepared in any one of Examples 1 to 7 and 11 g of 2-methyl-1- trimethylsilyl imidazole was heated to 80 °C. 23.7 ml of IN tetra-n- butylammonium fluoride solution was added dropwise for 10 min under reflux, and then the reaction mixture was stirred for 2 hours. After cooling to room temperature, 100 ml of water was added to the reaction mixture, and then stirred for 30 min. The resulting solid was filtered and washed with 100 ml of water to give 6.2 g of the title compound as a white solid (yield 92percent). Example 16 The mixture of 5 g of 1, 2,3, 9-tetrahydro-9-methyl-3-methylene-4H- carbazol-4-one prepared in any one of Examples 1 to 7 and 22 g of 2-methyl-1- trimethylsilyl imidazole was heated to 80°C. 2. 37ml of IN tetra-n-butylammonium fluoride solution was added dropwise for 10 min under reflux, and then the reaction mixture was stirred for 2 hours. After cooling to ambient temperature, 100 ml of water was added to the reaction mixture, and then stirred for 30 min. The resulting solid was filtered and washed with 100 ml of water to give 6.61 g of the title compound as a white solid (yield 98percent).
87% for 2.16667 h; Heating / reflux Example 14 5g of 1, 2,3, 9-tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one prepared in any one of Examples 1 to 7 and llg of 2-methyl-l-trimethylsilyl imidazole were suspended in 25 ml of acetonitrile. 1. 9ml of IN tetra-n- butylammonium fluoride solution was added dropwise for 10 min under reflux, and then the reaction mixture was stirred for 2 hours. After cooling to room temperature, 100 ml of water was added to the reaction mixture, and then stirred for 30 min. The resulting solid was filtered and washed with 100 ml of water to give 5.85 g of the title compound as a white solid (yield 87percent).

Reference: [1] Patent: WO2005/37823, 2005, A1, . Location in patent: Page/Page column 14-15
[2] Patent: WO2005/37823, 2005, A1, . Location in patent: Page/Page column 14
[3] Patent: WO2005/37823, 2005, A1, . Location in patent: Page/Page column 15
[4] Patent: WO2005/37823, 2005, A1, . Location in patent: Page/Page column 14
[5] Patent: WO2005/37823, 2005, A1, . Location in patent: Page/Page column 13-14
[6] Patent: WO2005/37823, 2005, A1, . Location in patent: Page/Page column 13
  • 2
  • [ 693-98-1 ]
  • [ 99614-64-9 ]
  • [ 99614-02-5 ]
YieldReaction ConditionsOperation in experiment
99% for 6 h; Heating / reflux Example 8 5 g of 1, 2,3, 9-tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one prepared in any one of Examples 1 to 7,5. 89 g of 2-methyl imidazole and 1 g of montmorillonite K10 were added to 100ml of toluene, and then the reaction mixture was stirred under reflux for 6 hours. After completion of reaction, the solvent was distilled off, and then chloroform was added to the resulting residue and the catalyst was filtered off. The filtrate was washed with water, dried over anhydrous magnesium sulfate, and evaporated. The resulting solid was purified with ethyl acetate to give 6.94 g of the title compound as white solid (yield 99percent).
94% for 3 - 4 h; Heating / reflux Example 4
Synthesis of Ondansetron Without Using Alumina
In this reaction, we examined the feasibility of producing ondansetron from 1,2,3,9-tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one without alumina as a catalyst.
The crude 1,2,3,9-tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one from Example 3 (145 grams, 0.69 mol) and 2-methylimidazole (71 grams; 0.86 mol) were added to toluene (800 mL), and the mixture was heated to reflux temperature.
After about 3-4 hours (TLC indicated that 1,2,3,9-tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one had been substantially consumed), the reaction was cooled to room temperature.
The resulting precipitate was isolated by filtration to provide 190 grams (0.65 mol; 94percent yield) of crude ondansetron.
Accordingly, ondansetron was prepared from 1,2,3,9-tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one in a yield of about 94percent after heating for about 3-4 hours.
Note that alumina was not used as a catalyst.
In addition, the ondansetron was isolated from the reaction mixture quickly and efficiently by filtering the reaction mixture.
91% for 2 h; Heating / reflux Example 13 The same procedures as described in Example 10 were repeated, except that toluene was employed instead of acetonitrile, to give 6.32 g of the title compound (yield 91percent).
90% for 6 h; Heating / reflux Example 9 The suspension of 5 g of 1, 2,3, 9-tetrahydro-9-methyl-3-methylene-4H- carbazol-4-one prepared in any one of Examples 1 to 7,5. 89 g of 2-methyl imidazole and 1 g of montmorillonite KSF in 100ml of toluene was stirred under reflux for 6 hours. After completion of reaction, the reaction solvent was distilled off, and then chloroform was added to the resulting residue, and then the catalyst was filtered off. The filtrate was washed with water, dried over anhydrous magnesium sulfate, and evaporated to dryness. The resulting solid was purified with ethyl acetate to give 6.3 g of the title compound as white solid (yield 90percent).
88.3% for 2 h; Heating / reflux Example 11 The same procedures as described in Example 10 were repeated, except that tetrahydrofuran was employed instead of acetonitrile, to give 6.14 g of the title compound (yield 88.3percent).
84.2% for 2 h; Heating / reflux Example 10 5 g of 1, 2,3, 9-tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one prepared in any one of Examples 1 to 7 and 11 g of 2-methyl-1-trimethylsilyl imidazole was suspended in 25 ml of acetonitrile. 23. 7ml of 1N tetra-n- butylammonium fluoride solution was added dropwise for 10 min under reflux, and then the reaction mixture was stirred for 2 hours. After cooling to room temperature, 100 ml of water was added to the reaction mixture, and then stirred for 30 min. The resulting solid was filtered and washed with 100 ml of water to give 5.85 g of the title compound as a white solid (yield 84.2percent).
80% for 2 h; Heating / reflux Example 12 The same procedures as described in Example 10 were repeated, except that 1.4-dioxane was employed instead of acetonitrile, to give 5.56 g of the title compound (yield 80percent).

Reference: [1] Patent: WO2005/37823, 2005, A1, . Location in patent: Page/Page column 11
[2] Patent: US2006/41004, 2006, A1, . Location in patent: Page/Page column 8
[3] Patent: WO2005/37823, 2005, A1, . Location in patent: Page/Page column 13
[4] Patent: WO2005/37823, 2005, A1, . Location in patent: Page/Page column 12
[5] Patent: WO2005/37823, 2005, A1, . Location in patent: Page/Page column 12
[6] Patent: WO2005/37823, 2005, A1, . Location in patent: Page/Page column 12
[7] Patent: WO2005/37823, 2005, A1, . Location in patent: Page/Page column 12
[8] Heterocycles, 1997, vol. 45, # 10, p. 2041 - 2043
  • 3
  • [ 693-98-1 ]
  • [ 99614-64-9 ]
  • [ 99614-02-5 ]
Reference: [1] Patent: WO2006/46253, 2006, A1, . Location in patent: Page/Page column 18-19
[2] Patent: WO2006/46253, 2006, A1, . Location in patent: Page/Page column 19
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 99614-64-9 ]

Ketones

Chemical Structure| 88368-15-4

[ 88368-15-4 ]

6,9-Dimethyl-2,3-dihydro-1H-carbazol-4(9H)-one

Similarity: 0.89

Chemical Structure| 27387-31-1

[ 27387-31-1 ]

1,2,3,9-Tetrahydro-9-methyl-4H-carbazole-4-one

Similarity: 0.89

Chemical Structure| 50776-26-6

[ 50776-26-6 ]

4-Methyl-2,3-dihydrocyclopenta[b]indol-1(4H)-one

Similarity: 0.87

Chemical Structure| 73825-22-6

[ 73825-22-6 ]

9-Ethyl-2,3-dihydro-1H-carbazol-4(9H)-one

Similarity: 0.85

Chemical Structure| 88368-16-5

[ 88368-16-5 ]

6-Chloro-9-methyl-2,3-dihydro-1H-carbazol-4(9H)-one

Similarity: 0.84

Related Parent Nucleus of
[ 99614-64-9 ]

Other Aromatic Heterocycles

Chemical Structure| 88368-15-4

[ 88368-15-4 ]

6,9-Dimethyl-2,3-dihydro-1H-carbazol-4(9H)-one

Similarity: 0.89

Chemical Structure| 27387-31-1

[ 27387-31-1 ]

1,2,3,9-Tetrahydro-9-methyl-4H-carbazole-4-one

Similarity: 0.89

Chemical Structure| 50776-26-6

[ 50776-26-6 ]

4-Methyl-2,3-dihydrocyclopenta[b]indol-1(4H)-one

Similarity: 0.87

Chemical Structure| 73825-22-6

[ 73825-22-6 ]

9-Ethyl-2,3-dihydro-1H-carbazol-4(9H)-one

Similarity: 0.85

Chemical Structure| 88368-16-5

[ 88368-16-5 ]

6-Chloro-9-methyl-2,3-dihydro-1H-carbazol-4(9H)-one

Similarity: 0.84