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[ CAS No. 181139-49-1 ] {[proInfo.proName]}

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Chemical Structure| 181139-49-1
Chemical Structure| 181139-49-1
Structure of 181139-49-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 181139-49-1 ]

CAS No. :181139-49-1 MDL No. :MFCD09038520
Formula : C16H16N2 Boiling Point : -
Linear Structure Formula :- InChI Key :NWDYSRZJOLDMRE-QDIHITRGSA-N
M.W : 236.31 Pubchem ID :2794493
Synonyms :

Safety of [ 181139-49-1 ]

Signal Word:Danger Class:9
Precautionary Statements:P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330 UN#:3077
Hazard Statements:H302-H319-H372-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 181139-49-1 ]

* 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 [ 181139-49-1 ]

[ 181139-49-1 ] Synthesis Path-Downstream   1~28

  • 1
  • [ 37942-07-7 ]
  • [ 181139-49-1 ]
  • [ 1030829-74-3 ]
YieldReaction ConditionsOperation in experiment
80% With sulphate sodium salt In chloroform for 24h; Heating;
  • 2
  • [ 181139-49-1 ]
  • [ 1015-37-8 ]
  • [ 1293394-41-8 ]
YieldReaction ConditionsOperation in experiment
53% With triethylamine In dichloromethane at 0 - 20℃; for 4h;
  • 3
  • [ 181139-49-1 ]
  • C78H70N4O6 [ No CAS ]
  • [ 10534-59-5 ]
  • C94H82N6O4*C2H3O2(1-)*C16H36N(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at 20℃;
  • 4
  • [ 15084-51-2 ]
  • [ 181139-49-1 ]
  • C26H28N2O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 0℃;
  • 5
  • [ 181139-49-1 ]
  • [ 349-88-2 ]
  • C22H19FN2O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 0℃;
  • 6
  • [ 181139-49-1 ]
  • [ 98-59-9 ]
  • C23H22N2O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 0℃;
  • 7
  • [ 181139-49-1 ]
  • [ 2991-42-6 ]
  • C23H19F3N2O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 0℃;
  • 8
  • [ 181139-49-1 ]
  • [ 21286-54-4 ]
  • C26H30N2O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 0℃;
  • 9
  • [ 6553-96-4 ]
  • [ 181139-49-1 ]
  • C31H38N2O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 0℃;
  • 10
  • [ 66715-65-9 ]
  • [ 181139-49-1 ]
  • (R,R)-11-(2-pyridinesulfonamido)-12-amino-9,10-dihydro-9,10-ethanoanthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With triethylamine In dichloromethane at 0 - 20℃; for 1h; 2 4.2. (R,R)-11-(2-Pyridinesulfonamido)-12-amino-9,10-dihydro-9,10-ethanoanthracene 14 A solution of 2-pyridinesulfonyl chloride (0.641 g, 3.61 mmol) in CH2Cl2 (10 mL) was slowly added to a solution of (R,R)-ethanoanthracene diamine (0.853 g, 3.61 mmol) and triethylamine (0.750 mL, 0.547 g, 5.41 mmol) in CH2Cl2 (30 mL) at 0 °C. After the addition was complete, the mixture was warmed to room temperature and stirred for 1 h. The reaction was quenched with water and extracted with CH2Cl2 (3 * 20 mL). The organic phase was dried over anhydrous sodium sulfate and the solvent was removed at reduced pressure. The residue was purified by column chromatography on deactivated silica gel (Et3N/SiO2 = 2.0% v/w, EtOAc/MeOH 9:1) to afford the product (71%) as a white solid. White solid, mp 209-211 °C. [α]D20 = -31.4 (c 1.0, CHCl3). 1H NMR (200 MHz, CDCl3): δ 2.87 (t, J = 2.8 Hz, 1H), 3.33 (t, J = 2.8 Hz, 1H), 4.06 (d, J = 2.8 Hz, 1H), 4.14 (d, J = 2.6 Hz, 1H), 7.05-7.31 (m, 9H), 7.43-7.49 (m, 2H), 7.80-7.99 (m, 2H), 8.61-8.65 (m, 2H). 13C NMR (50 MHz, CDCl3): δ 50.6, 51.9, 60.8, 64.3, 121.7, 124.0, 124.1, 125.7, 125.8, 126.1, 126.2, 126.4, 126.5, 137.3, 137.6, 141.5, 149.4, 157.6. IR (KBr) νmax 3345, 3282, 3023, 2961, 2824, 2791, 2708, 1732, 1581, 1484, 1460, 1426, 1387, 1324, 1281, 1240, 1169, 1127, 1100, 1985, 1060, 1023 cm-1. HRMS (FAB+) m/z calcd for [C21H20N3O2S]: 378.1276, found 378.1266.
  • 11
  • [ 181139-49-1 ]
  • (R,R)-11-(2,4,6-triisopropylbenzenesulfonamido)-12-[(S)-pyrrolidine-2-carboxamido]-9,10-dihydro-9,10-ethanoanthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C 3.1: trifluoroacetic acid / dichloromethane / 24 h / 20 °C
  • 12
  • [ 181139-49-1 ]
  • (R,R)-11-(2-pyridinesulfonamido)-12-[(S)-pyrrolidine-2-carboxamido]-9,10-dihydro-9,10-ethanoanthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C 3.1: trifluoroacetic acid / dichloromethane / 24 h / 20 °C
  • 13
  • [ 181139-49-1 ]
  • (R,R)-11-(N-4-trifluoromethylbenzenesulfonyl-N-methylamino)-12-[(S)-pyrrolidine-2-carboxamido]-9,10-dihydro-9,10-ethanoanthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C 3.1: potassium carbonate / acetone / 4 h / Reflux 4.1: trifluoroacetic acid / dichloromethane / 24 h / 20 °C
  • 14
  • [ 181139-49-1 ]
  • (R,R)-11-[(1S,2)-(7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonamido]-12-[(S)-1-(tert-butoxy carbonyl)pyrrolidine-2-carboxamido]-9,10-dihydro-9,10-ethanoanthracene [ No CAS ]
  • (R,R)-11-[(1S,2)-(7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonamido]-12-[(S)-1-(tert-butoxy carbonyl)pyrrolidine-2-carboxamido]-9,10-dihydro-9,10-ethanoanthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C 3.1: sodium tetrahydroborate / methanol / 1.5 h / 0 °C
  • 15
  • [ 181139-49-1 ]
  • (R,R)-11-(4-trifluoromethylbenzenesulfonamido)-12-[(S)-pyrrolidine-2-carboxamido]-9,10-dihydro-9,10-ethanoanthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C 3.1: trifluoroacetic acid / dichloromethane / 24 h / 20 °C
  • 16
  • [ 181139-49-1 ]
  • (R,R)-11-(4-trifluoromethylbenzenesulfonamido)-12-[(S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxamido]-9,10-dihydro-9,10-ethanoanthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C
  • 17
  • [ 181139-49-1 ]
  • (R,R)-11-(4-methylbenzenesulfonamido)-12-[(S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxamido]-9,10-dihydro-9,10-ethanoanthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C
  • 18
  • [ 181139-49-1 ]
  • (R,R)-11-(4-fluorobenzenesulfonamido)-12-[(S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxamido]-9,10-dihydro-9,10-ethanoanthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C
  • 19
  • [ 181139-49-1 ]
  • (R,R)-11-(4-tert-butylbenzenesulfonamido)-12-[(S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxamido]-9,10-dihydro-9,10-ethanoanthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C
  • 20
  • [ 181139-49-1 ]
  • (R,R)-11-(2,4,6-triisopropylbenzenesulfonamido)-12-[(S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxamido]-9,10-dihydro-9,10-ethanoanthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C
  • 21
  • [ 181139-49-1 ]
  • (R,R)-11-(2-pyridinesulfonamido)-12-[(S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxamido]-9,10-dihydro-9,10-ethanoanthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C
  • 22
  • [ 181139-49-1 ]
  • (R,R)-11-[(S)-(7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonamido]-12-[(S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxamido]-9,10-dihydro-9,10-ethanoanthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C
  • 23
  • [ 181139-49-1 ]
  • (R,R)-11-(N-4-trifluoromethylbenzenesulfonyl-N-methylamino)-12-[(S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxamido]-9,10-dihydro-9,10-ethanoanthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C 3.1: potassium carbonate / acetone / 4 h / Reflux
  • 24
  • [ 181139-49-1 ]
  • (R,R)-11-(4-methylbenzenesulfonamido)-12-[(S)-pyrrolidine-2-carboxamido]-9,10-dihydro-9,10-ethanoanthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C 3.1: trifluoroacetic acid / dichloromethane / 24 h / 20 °C
  • 25
  • [ 181139-49-1 ]
  • (R,R)-11-(4-fluorobenzenesulfonamido)-12-[(S)-pyrrolidine-2-carboxamido]-9,10-dihydro-9,10-ethanoanthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C 3.1: trifluoroacetic acid / dichloromethane / 24 h / 20 °C
  • 26
  • [ 181139-49-1 ]
  • (R,R)-11-(4-tert-butylbenzenesulfonamido)-12-[(S)-pyrrolidine-2-carboxamido]-9,10-dihydro-9,10-ethanoanthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C 3.1: trifluoroacetic acid / dichloromethane / 24 h / 20 °C
  • 27
  • [ 16567-18-3 ]
  • [ 181139-49-1 ]
  • (12R)‐N11,N12‐di(quinolin‐8‐yl)‐9,10‐dihydro‐9,10‐ethanoanthracene‐11,12‐diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 85℃; Schlenk technique; Inert atmosphere; General Procedure (Scheme 2): General procedure: To an oven-dried Schlenk flask were added diamine 3 (1.0 equiv),Pd2(dba)3 (5 mol%), rac-BINAP (10 mol%), NaOtBu (3.0 equiv), and toluene under Ar atmosphere.Then 8-haloqunoline 4 (2.2 equiv) was added directly. The flask was sealed, and the reaction wasstirred at 85 °C until the complete consumption of the starting material 3. The mixture was cooled toroom temperature, filtered through a silica plug, and the plug was washed with EA. The combinedfiltrates were concentrated under reduced pressure, and the residue was purified by silica gelchromatography to give the desired product Ln.
  • 28
  • [ 61047-43-6 ]
  • [ 181139-49-1 ]
  • (11R,12R)-N<SUP>11</SUP>,N<SUP>12</SUP>-bis(2-methylquinolin-8-yl)-9,10-dihydro-9,10-ethanoanthracene-11,12-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 90℃; Inert atmosphere;
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