No renderable structure data available
C1=CC(=C(C(=C1)F)Cl)CNChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | (2-chloro-3-fluorophenyl)methanamine |
|---|---|
| IUPAC Name | — |
| CAS Number | 72235-54-2 |
| Database ID | 50998690 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
(2-chloro-3-fluorophenyl)methanamine (CAS 72235-54-2) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 50998690
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-939266494c104d3587501cae9c76785cConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-3989267193064ad58af717a0bea5635bConditions: temp:24.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)pent-4-en-2-yl(methyl)carbamate (91.0 g, 242.6 mmol) in DCM (750 mL) was added TMSOTf (87.8 mL, 485.2 mmol) at 0° C. The mixture was stirred for 1 h, and then poured into saturated aq. NH4Cl (1 L) and CH2Cl2 (1 L) (Note: water (700 mL) was added to dissolve salts). The organic layer was then washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was re-dissolved in THF (300 mL) and DIEA (84.5 mL, 485.2 mmol). To this THF solution was added a pre-stirred solution of 4-nitrophenylchloroformate (56.3 g, 279.0 mmol), 2-chloro-3-fluorobenzylamine (46.5 g, 291.1 mmol), and DIEA (50.7 mL, 291.1 mmol) in THF (1.1 L) at 0° C. The reaction mixture was stirred for 2 h allowing the reaction to gradually warm to 24° C. at which point the LCMS analysis revealed reaction completion. The mixture was concentrated under reduced pressure and purified on silica gel column using a mixture of hexanes and EtOAc to give 5-(tert-butyl-dimethyl-silanyloxy)-4-[3-(2-chloro-3-fluoro-benzyl)-1-methyl-ureido]-pentanoic acid methyl ester (73.1 g, 65% over two steps). LRMS (M+H+) m/z 461.1. The organic layer was then washed with brine dried over Na2SO4 concentrated under reduced pressure The resulting residue was re-dissolved in THF (300 mL) The reaction mixture was stirred for 2 h the reaction reaction completion The mixture was concentrated under reduced pressure purified on silica gel column a mixture of hexanes and EtOAc
Source ID: ord-40e68158a3824e7faf89ceb015669861Conditions: temp:24.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of Isoquinolin-3-yl-carbamic acid 2-(tert-butoxycarbonyl-methyl-amino)-3-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-propyl ester (2.9 g, 5.93 mmol) in DCM (200 mL) was added TFA (12 mL) at 0° C. The mixture was stirred for 2 h, concentrated under reduced pressure, and re-dissolved in THF (10 mL) and DIEA (6.6 mL, 37.8 mmol). To this THF solution was added pre-stirred solution of 4-nitrophenylchloroformate (1.33 g, 6.62 mmol), 2-chloro-3-fluorobenzylamine (1.0 g, 6.3 mmol), and DIEA (1.2 mL, 6.9 mmol) in THF (85 mL) at 0° C. The reaction mixture was stirred for 2 h allowing the reaction to gradually warm to 24° C. The mixture was concentrated under reduced pressure, re-dissolved in MeOH, filtered, and purified by RP-HPLC using a mixture of acetonitrile and H2O to give isoquinolin-3-yl-carbamic acid 2-[3-(2-chloro-3-fluoro-benzyl)-1-methyl-ureido]-3-(2,3-dihydroxy-propoxy)-propyl ester (1.1 g, 45% over two steps). LRMS (M+H+) m/z 535.1. concentrated under reduced pressure re-dissolved in THF (10 mL) The reaction mixture was stirred for 2 h the reaction The mixture was concentrated under reduced pressure re-dissolved in MeOH filtered purified by RP-HPLC a mixture of acetonitrile and H2O
Source ID: ord-7fcb34d23e954a1888c53ba25186fef8Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A 5 liter 3-neck RBF was charged with 4-nitrophenylchloroformate (126.3 g, 627 mmol), DCM (3000 mL), under N2 atm and chilled in a 0° C. ice bath. A solution of 2-chloro,3-fluorobenzylamine (100.0 g, 627 mmol) followed by solid Sodium Carbonate (155.0 g, 1460 mmol) was quickly added in one portion into the reaction solution. The reaction mixture was stirred at 0° C. for 1 h and an LC/MS was taken to confirm consumption of the starting material and presence of the nitrophenyl intermediate. The reaction mixture was allowed to warm to room temperature and stirred for approximately 2 h. The mixture was filtered, and the filtrate was concentrated to give a white solid. The solid was redissolved with 600 ml of DCM and heated to 40° C. until all of the material went into solution. The solution was chilled in a 0° C. ice bath to form crystals. The crystals were collected and dried under vacuum to give 4-nitrophenyl 2-chloro-3-fluorobenzylcarbamate. (150 g, 75%). was quickly added in one portion into the reaction solution consumption of the starting material and presence of the nitrophenyl intermediate to warm to room temperature stirred for approximately 2 h The mixture was filtered the filtrate was concentrated to give a white solid heated to 40° C. until all of the material The solution was chilled in a 0° C. ice bath to form crystals The crystals were collected dried under vacuum
Source ID: ord-f2e617242ddf4149b0fa6351534048e3Conditions: temp:24.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)pent-4-en-2-yl(methyl)carbamate (91.0 g, 242.6 mmol) in DCM (750 mL) was added TMSOTf (87.8 mL, 485.2 mmol) at 0° C. The mixture was stirred for 1 h, and then poured into saturated aq. NH4Cl (1 L) and CH2Cl2 (1 L) (Note: water (700 mL) was added to dissolve salts). The organic layer was then washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was re-dissolved in THF (300 mL) and DIEA (84.5 mL, 485.2 mmol). To this THF solution was added a pre-stirred solution of 4-nitrophenylchloroformate (56.3 g, 279.0 mmol), 2-chloro-3-fluorobenzylamine (46.5 g, 291.1 mmol), and DIEA (50.7 mL, 291.1 mmol) in THF (1.1 L) at 0° C. The reaction mixture was stirred for 2 h allowing the reaction to gradually warm to 24° C. at which point the LCMS analysis revealed reaction completion. The mixture was concentrated under reduced pressure and purified on silica gel column using a mixture of hexanes and EtOAc to give 5-(tert-butyl-dimethyl-silanyloxy)-4-[3-(2-chloro-3-fluoro-benzyl)-1-methyl-ureido]-pentanoic acid methyl ester (73.1 g, 65% over two steps). LRMS (M+H+) m/z 461.1. The organic layer was then washed with brine dried over Na2SO4 concentrated under reduced pressure The resulting residue was re-dissolved in THF (300 mL) The reaction mixture was stirred for 2 h the reaction reaction completion The mixture was concentrated under reduced pressure purified on silica gel column a mixture of hexanes and EtOAc
Source ID: ord-90e0c63993f9451c89b5a90d6f420688Conditions: temp:24.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of Isoquinolin-3-yl-carbamic acid 2-(tert-butoxycarbonyl-methyl-amino)-3-(2,2-dimethyl-[1,3]-dioxolan-4-ylmethoxy)-propyl ester (2.9 g, 5.93 mmol) in DCM (200 mL) was added TFA (12 mL) at 0° C. The mixture was stirred for 2 h, concentrated under reduced pressure, and re-dissolved in THF (10 mL) and DIEA (6.6 mL, 37.8 mmol). To this THF solution was added pre-stirred solution of 4-nitrophenylchloroformate (1.33 g, 6.62 mmol), 2-chloro-3-fluorobenzylamine (1.0 g, 6.3 mmol), and DIEA (1.2 mL, 6.9 mmol) in THF (85 mL) at 0° C. The reaction mixture was stirred for 2 h allowing the reaction to gradually warm to 24° C. The mixture was concentrated under reduced pressure, re-dissolved in MeOH, filtered, and purified by RP-HPLC using a mixture of acetonitrile and H2O to give isoquinolin-3-yl-carbamic acid 2-[3-(2-chloro-3-fluoro-benzyl)-1-methyl-ureido]-3-(2,3-dihydroxy-propoxy)-propyl ester (1.1 g, 45% over two steps). LRMS (M+H+) m/z 535.1. concentrated under reduced pressure re-dissolved in THF (10 mL) The reaction mixture was stirred for 2 h the reaction The mixture was concentrated under reduced pressure re-dissolved in MeOH filtered purified by RP-HPLC a mixture of acetonitrile and H2O
Source ID: ord-592e363ca961444a8bf8e71818488c6fConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A 5 liter 3-neck RBF was charged with 4-nitrophenylchloroformate (126.3 g, 627 mmol), DCM (3000 mL), under N2 atm and chilled in a 0° C. ice bath. A solution of 2-chloro,3-fluorobenzylamine (100.0 g, 627 mmol) followed by solid Sodium Carbonate (155.0 g, 1460 mmol) was quickly added in one portion into the reaction solution. The reaction mixture was stirred at 0° C. for 1 h and an LC/MS was taken to confirm consumption of the starting material and presence of the nitrophenyl intermediate. The reaction mixture was allowed to warm to room temperature and stirred for approximately 2 h. The mixture was filtered, and the filtrate was concentrated to give a white solid. The solid was redissolved with 600 ml of DCM and heated to 40° C. until all of the material went into solution. The solution was chilled in a 0° C. ice bath to form crystals. The crystals were collected and dried under vacuum to give 4-nitrophenyl 2-chloro-3-fluorobenzylcarbamate. (150 g, 75%). was quickly added in one portion into the reaction solution consumption of the starting material and presence of the nitrophenyl intermediate to warm to room temperature stirred for approximately 2 h The mixture was filtered the filtrate was concentrated to give a white solid heated to 40° C. until all of the material The solution was chilled in a 0° C. ice bath to form crystals The crystals were collected dried under vacuum
Source ID: ord-5f82b3fc56b24c88ac027fc1fe2d5655Conditions: temp:24.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)pent-4-en-2-yl(methyl)carbamate (91.0 g, 242.6 mmol) in DCM (750 mL) was added TMSOTf (87.8 mL, 485.2 mmol) at 0° C. The mixture was stirred for 1 h, and then poured into saturated aq. NH4Cl (1 L) and CH2Cl2 (1 L) (Note: water (700 mL) was added to dissolve salts). The organic layer was then washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was re-dissolved in THF (300 mL) and DIEA (84.5 mL, 485.2 mmol). To this THF solution was added a pre-stirred solution of 4-nitrophenylchloroformate (56.3 g, 279.0 mmol), 2-chloro-3-fluorobenzylamine (46.5 g, 291.1 mmol), and DIEA (50.7 mL, 291.1 mmol) in THF (1.1 L) at 0° C. The reaction mixture was stirred for 2 h allowing the reaction to gradually warm to 24° C. at which point the LCMS analysis revealed reaction completion. The mixture was concentrated under reduced pressure and purified on silica gel column using a mixture of hexanes and EtOAc to give 5-(tert-butyl-dimethyl-silanyloxy)-4-[3-(2-chloro-3-fluoro-benzyl)-1-methyl-ureido]-pentanoic acid methyl ester (73.1 g, 65% over two steps). LRMS (M+H+) m/z 461.1. The organic layer was then washed with brine dried over Na2SO4 concentrated under reduced pressure The resulting residue was re-dissolved in THF (300 mL) The reaction mixture was stirred for 2 h the reaction reaction completion The mixture was concentrated under reduced pressure purified on silica gel column a mixture of hexanes and EtOAc
Source ID: ord-39273709a5b14a87a2d31da2df07b64cConditions: temp:24.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of Isoquinolin-3-yl-carbamic acid 2-(tert-butoxycarbonyl-methyl-amino)-3-(2,2-dimethyl-[1,3]-dioxolan-4-ylmethoxy)-propyl ester (2.9 g, 5.93 mmol) in DCM (200 mL) was added TFA (12 mL) at 0° C. The mixture was stirred for 2 h, concentrated under reduced pressure, and re-dissolved in THF (10 mL) and DIEA (6.6 mL, 37.8 mmol). To this THF solution was added pre-stirred solution of 4-nitrophenylchloroformate (1.33 g, 6.62 mmol), 2-chloro-3-fluorobenzylamine (1.0 g, 6.3 mmol), and DIEA (1.2 mL, 6.9 mmol) in THF (85 mL) at 0° C. The reaction mixture was stirred for 2 h allowing the reaction to gradually warm to 24° C. The mixture was concentrated under reduced pressure, re-dissolved in MeOH, filtered, and purified by RP-HPLC using a mixture of acetonitrile and H2O to give isoquinolin-3-yl-carbamic acid 2-[3-(2-chloro-3-fluoro-benzyl)-1-methyl-ureido]-3-(2,3-dihydroxy-propoxy)-propyl ester (1.1 g, 45% over two steps). LRMS (M+H+) m/z 535.1. concentrated under reduced pressure re-dissolved in THF (10 mL) The reaction mixture was stirred for 2 h the reaction The mixture was concentrated under reduced pressure re-dissolved in MeOH filtered purified by RP-HPLC a mixture of acetonitrile and H2O
Source ID: ord-920b60c19a304874b899e8a5d216e573Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A 5 liter 3-neck RBF was charged with 4-nitrophenylchloroformate (126.3 g, 627 mmol), DCM (3000 mL), under N2 atm and chilled in a 0° C. ice bath. A solution of 2-chloro,3-fluorobenzylamine (100.0 g, 627 mmol) followed by solid Sodium Carbonate (155.0 g, 1460 mmol) was quickly added in one portion into the reaction solution. The reaction mixture was stirred at 0° C. for 1 h and an LC/MS was taken to confirm consumption of the starting material and presence of the nitrophenyl intermediate. The reaction mixture was allowed to warm to room temperature and stirred for approximately 2 h. The mixture was filtered, and the filtrate was concentrated to give a white solid. The solid was redissolved with 600 ml of DCM and heated to 40° C. until all of the material went into solution. The solution was chilled in a 0° C. ice bath to form crystals. The crystals were collected and dried under vacuum to give 4-nitrophenyl 2-chloro-3-fluorobenzylcarbamate. (150 g, 75%). was quickly added in one portion into the reaction solution consumption of the starting material and presence of the nitrophenyl intermediate to warm to room temperature stirred for approximately 2 h The mixture was filtered the filtrate was concentrated to give a white solid heated to 40° C. until all of the material The solution was chilled in a 0° C. ice bath to form crystals The crystals were collected dried under vacuum
Source ID: ord-0cd58189bae04e9bbca50511f77924a8Conditions: temp:24.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)pent-4-en-2-yl(methyl)carbamate (91.0 g, 242.6 mmol) in DCM (750 mL) was added TMSOTf (87.8 mL, 485.2 mmol) at 0° C. The mixture was stirred for 1 h, and then poured into saturated aq. NH4Cl (1 L) and CH2Cl2 (1 L) (Note: water (700 mL) was added to dissolve salts). The organic layer was then washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was re-dissolved in THF (300 mL) and DIEA (84.5 mL, 485.2 mmol). To this THF solution was added a pre-stirred solution of 4-nitrophenylchloroformate (56.3 g, 279.0 mmol), 2-chloro-3-fluorobenzylamine (46.5 g, 291.1 mmol), and DIEA (50.7 mL, 291.1 mmol) in THF (1.1 L) at 0° C. The reaction mixture was stirred for 2 h allowing the reaction to gradually warm to 24° C. at which point the LCMS analysis revealed reaction completion. The mixture was concentrated under reduced pressure and purified on silica gel column using a mixture of hexanes and EtOAc to give 5-(tert-butyl-dimethyl-silanyloxy)-4-[3-(2-chloro-3-fluoro-benzyl)-1-methyl-ureido]-pentanoic acid methyl ester (73.1 g, 65% over two steps). LRMS (M+H+) m/z 461.1. The organic layer was then washed with brine dried over Na2SO4 concentrated under reduced pressure The resulting residue was re-dissolved in THF (300 mL) The reaction mixture was stirred for 2 h the reaction reaction completion The mixture was concentrated under reduced pressure purified on silica gel column a mixture of hexanes and EtOAc
Source ID: ord-40e68158a3824e7faf89ceb015669861PubChem References
These sources are listed in the compound's public database record.
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