99614-64-9

Basic information

• Product Name: 1,2,3,9-TETRAHYDRO-9-METHTYL-3-METHYLENE-4H-CARBAZOL-4-ONE
• Synonyms: Ondansetron impurity D (PhEur);Ondansetron Related Compound D (USP);9-Methyl-3-methylene-1,2,3,9-tetrahydro-4H-carbazol-4-one;Ondansetron EP Impurity D;1,2,3,9-TETRAHYDRO-9-METHYL-3-METHYLENE-4H-CARBAZOL-4-ONE;1,2,3,9-TETRAHYDRO-9-METHTYL-3-METHYLENE-4H-CARBAZOL-4-ONE;4H-Carbazol-4-one,1,2,3,9-tetrahydro-9-Methyl-3-Methylene-;Ondansetron HCl EP IMpurity-D (USP RC D)
• CAS NO: 99614-64-9
• Molecular Formula: C₁₄H₁₃NO
• Molecular Weight: 211.26
• Product Categories: (intermediate of ondansetron);Aromatics;Heterocycles;Impurities;Intermediates
• Mol File: 99614-64-9.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 394℃
• Flash Point: 192℃
• Appearance: white or almost white power
• Density: 1.18
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.633
• Storage Temp.: 2-8°C
• BRN: 7920329
• CAS DataBase Reference: 1,2,3,9-TETRAHYDRO-9-METHTYL-3-METHYLENE-4H-CARBAZOL-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,9-TETRAHYDRO-9-METHTYL-3-METHYLENE-4H-CARBAZOL-4-ONE(99614-64-9)
• EPA Substance Registry System: 1,2,3,9-TETRAHYDRO-9-METHTYL-3-METHYLENE-4H-CARBAZOL-4-ONE(99614-64-9)

Safety Data

• Hazard Codes: T
• Statements: 25-43
• Safety Statements: 36/37-45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 99614-64-9(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

1,2,3,9-Tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one is an impurity of Ondansetron (O655000).

InChI:InChI=1/C14H13NO/c1-9-7-8-12-13(14(9)16)10-5-3-4-6-11(10)15(12)2/h3-6H,1,7-8H2,2H3

Upstream product

• 50-00-0 formaldehyd 
• 27387-31-1 9-methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one 
• 153139-56-1 3-[(dimethylamino)methyl]-1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one 
• 108-74-7 1,3,5-trimethyl-1,3,5-triazacyclohexane 
• 51-80-9 bis-(dimethylamino)methane 
• 68922-17-8 1,1'-methylenebis(3-methylpiperidine) 
• 102-53-4 bis-(diethylamino)methane 
• 880-09-1 di(N-piperidinyl)methane 
• 110-91-8 morpholine 
• 506-59-2 N,N-dimethylammonium chloride 
• 99614-02-5 ondanserton 
• 603-76-9 1-methylindole 
• 27421-51-8 1-methyl-1H-indole-2-carboxaldehyde 
• 88221-09-4 ethyl 3-(1-methyl-1H-indol-2-yl)acrylate 

Downstream Products

• 99614-02-5 ondanserton 

Relevant articles and documents

C(sp2)-H Bond Multiple Functionalization in Air for Construction of Tetrahydrocarbazoles with Continuous Quaternary Carbons and Polycyclic Diversification

The C(sp2)-H function of indole ketone with diazo compound via a rhodium(II)-catalyzed intramolecular electrophilic trapping reaction under mild conditions in air was demonstrated. The established methodology provided a highly efficient approach for direct synthesis of mutisubstituted tetrahydrocarbazoles with continuous quaternary carbons. The resulting products facilitate further modification to conveniently construct tetrahydrocarbazoles with additional fused heterocyclic rings. By phenotypic screening, several products exhibit good anticancer bioctivities in osteosarcoma cell lines.

A ONE-POT PROCESS FOR THE PREPARATION OF ANTIEMETIC AGENT, 1,2,3,9-TETRAHYDRO-9-METHYL-3[(2-METHYL)-1H-IMIDAZOLE-1-YL)METHYL]-4H-CARBAZOL-4-O

A one-pot industrial process for preparing 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazole-1-yl)methyl]-4H-carbazol-4-one of Formula-(I) from 1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one of Formula-(IV) involves reaction of Formula (IV) with HNR1R2 salt and paraformaldehyde, where R1,R2 are independently alkyl groups or together forms a cyclic alkyl group, in a solvent system of acetic acid and hydrocarbon solvent to form a crude mixture of intermediate compounds of Formula (III) and (VIII), which is converted to ondansetron (Formula (I)) without isolation by reaction with 2-methyimidazole in a suitable solvent system in the same pot.

PROCESS FOR PREPARING 1,2,3,9-TETRAHYDRO-9-METHYL-3-[(2-METHYL-1H-IMIDAZOLE-1-YL)METHYL]-4H-CARBAZOL-4-ONE OR ITS SALT

The present invention provides an improved process for preparing 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one or its salt, which is useful as an anti-vomiting agent, in a high yield under a mild condition, so as to be favorably applied to a large-scale mass production thereof.