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[ CAS No. 54231-41-3 ]

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Chemical Structure| 54231-41-3
Chemical Structure| 54231-41-3
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Product Details of [ 54231-41-3 ]

CAS No. :54231-41-3 MDL No. :MFCD00490113
Formula : C5H6BrN3 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :188.03 g/mol Pubchem ID :-
Synonyms :

Safety of [ 54231-41-3 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P264-P270-P271-P280-P301+P310+P330-P302+P352-P304+P340+P312-P305+P351+P338+P310-P332+P313-P403+P233-P405-P501 UN#:2811
Hazard Statements:H301-H315-H318-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 54231-41-3 ]

  • Downstream synthetic route of [ 54231-41-3 ]

[ 54231-41-3 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 719274-57-4 ]
  • [ 54231-41-3 ]
  • [ 1140898-99-2 ]
YieldReaction ConditionsOperation in experiment
47% Stage #1: 4-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]bicyclo[2.2.2]octane-1-carboxylic acid With 4-methyl-morpholine; chloroformic acid ethyl ester In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: 3-bromo-2-hydrazinylpyridine In tetrahydrofuran at 0 - 20℃; for 3h; 17 To a solution of compound 17B (1.0 g, 3.2 mmol) in 25 mL of dry tetrahydrofuran was added NMM (0.65 mL, 5.9 mmol) at room temperature. Upon completion of addition, the solution was cooled to 0° C. and ethyl carbonochloridate (0.38 mL, 3.95 mmol) was added dropwise. The resulting mixture was stirred at 0° C. for 30 min, and then 3-bromo-2-hydrazinylpyridine (compound 1A, 1.49 g, 3.95 mmol) was added in one portion. The reaction mixture was stirred at 0° C. for 30 min, and then at room temperature for 2.5 h. After this time, the reaction mixture was quenched with water. The organic layer was separated, dried over MgSO4 and concentrated in vacuo. The resulting crude residue was purified by flash chromatography over 120 g of silica gel (gradient elution with 0-40% ethyl acetate in hexanes) to give compound 17C (0.73 g, 1.5 mmol, 47%) as a white solid. LCMS (m/z)=488 (M+H)+.
  • 2
  • [ 72934-37-3 ]
  • [ 54231-41-3 ]
  • [ 1140898-81-2 ]
YieldReaction ConditionsOperation in experiment
63% A stirred solution of 1-(4-chlorophenyl)cyclopropanecarboxylic acid (8.71 g, 44.3 mmol) and NMM in THF (200 mL) was cooled 0° C. Once at the prescribed temperature, isobutyl chloroformate was added dropwise over 10 min, and the resulting white suspension was stirred for 1h. After this time, a solution of compound 1A (8.33g, 44.3 mmol) in THF (250 mL) was added over 10 min. Upon completion of addition, the reaction mixture was stirred for 15 min. At the conclusion of this period, the reaction mixture was warmed to RT, where it was stirred for 2 h. After this time, the reaction mixture was partitioned between ethyl acetate and water. The organic phase was separated, dried over Na2SO4, and then concentrated in vacuo to afford compound 1B (10.2 g, 27.8 mmol, 63percent yield) as an off-white solid. LC/MS (m/z)=366 (M+H)+.
A mixture of l-(4-chlorophenyl)cyclopropanecarboxylic acid (2.650 g, 13.48 mmol) and N-methylmorpholine (2.65 ml, 24.12 mmol) in 106 mL of THF was cooled to 0 °C. To this was added isobutyl chloroformate (2.212 ml, 16.85 mmol) dropwise over a period of 10 min. The mixture was allowed to stir at 0 °C for 1 h, and then a solution of 3-bromo-2-hydrazinylpyridine (3.17 g, 16.85 mmol) in 20 mL of THF was added. The reaction mixture was warmed to RT and stirred for 16 h. TLC analysis on silica gel using 5/95 ( v/v) MeOH/ CH2C12 and LC/MS analysis showed the reaction to be completed. The reaction was quenched with water. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic extracts were dried over anhydrous MgS04, filtered and concentrated in vacuo to give a light brown solid. This solid was triturated with 1/1 (v/v) ether/hexane (2 x 4 mL) to remove some of the light brown color. The solvents were decanted and the resulting solid was dried under vacuum to give 4.5 g (82percent yield) of a light yellow white solid. 1H-NMR (DMSO-d6, 400 MHz) delta 9.09 (d, J=2.0 Hz, 1H), 8.09 (dd, J=4.8, 1.5 Hz, 1H), 8.04 (d, J=2.0 Hz, 1H), 7.85 - 7.79 (m, 1H), 7.49 - 7.44 (m, 2H), 7.42 - 7.38 (m, 2H), 6.68 (dd, J=7.6, 4.7 Hz, 1H), 1.45 - 1.38 (m, 2H), 1.11 - 1.05 (m, 2H). LC/MS (ESI) 366.0/368.0/370.0 (M+1/M+3/M+5). The product was used with no further purification in the next step.
  • 3
  • [ 52200-48-3 ]
  • [ 54231-41-3 ]
YieldReaction ConditionsOperation in experiment
91% With hydrazine; In 1,4-dioxane; at 20℃; for 15h;Heating / reflux; To a solution of <strong>[52200-48-3]2-chloro-3-bromopyridine</strong> (14.5 g, 75.1 mmol) in 100 mL of dioxane was added anhydrous hydrazine (35.4 mL, 1130 mmol) at RT. The reaction mixture was heated at reflux for 15 h, and then cooled to RT. After most of the solvent was removed under reduced pressure, the resulting residue was diluted with ethyl acetate, washed with water, dried over Na2SO4, and concentrated to provide a residue. Recrystallization of the residue in ethyl acetate and hexanes gave compound 1A (12.9 g, 91%) as a solid. LC/MS (m/z)=188 (M+H)+.
With pyridine; hydrazine; at 60℃; for 24h; Step A: 3-bromo-2-hydrazinylpyridineTo a stirring solution of <strong>[52200-48-3]3-bromo-2-chloropyridine</strong> (3.74 g, 19.43 mmol) in pyridine (40 mL) was added hydrazine (2 g, 62.4 mmol). The resulting mixture was stirred at 60C for 24 h. After cooled to room temperature and refrigerated, product precipitated out as a white needle solid. The product was filtered and washed with water, dried under high vacuum overnight to afford product 3-bromo-2-hydrazinylpyridine.
With hydrazine; In tetrahydrofuran; for 40h;Reflux; 3- bromo-2-hvdrazinylpyridine (1-4) To <strong>[52200-48-3]3-bromo-2-chloropyridine</strong> (1-3) (12.5 g, 65 mmol) in THF (100 mL) was added hydrazine (10.4 g, 10.2 mL, 325 mmol). The mixture was heated to reflux and stirred vigorously for 16 h. An additional portion of hydrazine (5.1 g, 5.0 mL, 159 mmol) was added and the reaction was heated for another 24 h. After cooling, the mixture was concentrated in vacuo, suspended in water (50 mL), and extracted with EtOAc (1 x 350 mL, 1 x 50 mL). Combined organic layers were washed with brine (50 mL), dried over MgS04, filtered, and concentrated in vacuo. The resulting crude product (1-4) was used in the subsequent step without further purification. LC/MS: m/z (M+H) = 187.9.
  • 4
  • [ 54231-41-3 ]
  • [ 75-36-5 ]
  • [ 1190392-72-3 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at -78 - 20℃; for 0.333333h; 64.A To a solution of 0.800 g (3.38 mmol) of 2,3-dibromopyridine in 10 mL of anhydrous 1,4-dioxane was added 0.325 g (10.1 mmol) of anhydrous hydrazine and the resulting mixture was heated to 85°C for 8 h. The reaction mixture was cooled to ambient temperature then evaporated to dryness in vacuo. The crude residue was dissolved in anhydrous dichloromethane and cooled to -78°C in a dry ice acetone bath under an atmosphere of nitrogen. Next, 1.0 mL (6.8 mmol) of triethylamine was added followed by 0.210 g (2.72 mmol) of acetyl chloride. The resulting mixture was allowed to warm to ambient temperature over 20 min then all volatiles were removed in vacuo. The residue was suspended in 20 mL of water and extracted with ethyl acetate (3 x 10 mL). The combined extracts were washed with brine, dried over magnesium sulfate, filtered and evaporated to afford the title compound (0.18 g, 23%). LC- MS: m/z (ES) 230, 232 (MH)+ and 188, 190 (MH-COCH3)+.
  • 5
  • [ 13534-89-9 ]
  • [ 54231-41-3 ]
YieldReaction ConditionsOperation in experiment
With hydrazine In 1,4-dioxane at 85℃; for 8h; 64.A To a solution of 0.800 g (3.38 mmol) of 2,3-dibromopyridine in 10 mL of anhydrous 1,4-dioxane was added 0.325 g (10.1 mmol) of anhydrous hydrazine and the resulting mixture was heated to 85°C for 8 h. The reaction mixture was cooled to ambient temperature then evaporated to dryness in vacuo. The crude residue was dissolved in anhydrous dichloromethane and cooled to -78°C in a dry ice acetone bath under an atmosphere of nitrogen. Next, 1.0 mL (6.8 mmol) of triethylamine was added followed by 0.210 g (2.72 mmol) of acetyl chloride. The resulting mixture was allowed to warm to ambient temperature over 20 min then all volatiles were removed in vacuo. The residue was suspended in 20 mL of water and extracted with ethyl acetate (3 x 10 mL). The combined extracts were washed with brine, dried over magnesium sulfate, filtered and evaporated to afford the title compound (0.18 g, 23%). LC- MS: m/z (ES) 230, 232 (MH)+ and 188, 190 (MH-COCH3)+.
  • 6
  • [ 54231-41-3 ]
  • [ 153034-82-3 ]
  • [ 1356054-80-2 ]
YieldReaction ConditionsOperation in experiment
74.9% In 1-methyl-pyrrolidin-2-one; at 185℃; for 0.75h;Inert atmosphere; capped; To a dry 15 mL ChemGlass pressure bottle under 2 was added 2-fluoro-4- iodonicotinaldehyde (725 mg, 2.89 mmol), 3-bromo-2-hydrazinylpyridine (543 mg, 2.89 mmol) and anhydrous NMP (Volume: 4.0 mL). The reaction mixture was flushed with argon, securely capped, and heated to 185C for 45 min. The reaction mixture was worked up according to the procedure described in Intermediate 69A and the crude product was purified by Biotage Silica gel chromatography using a 12g Thompson Single Step silica cartridge with a linear gradient from 100% CH2CI2 to 100% ethyl acetate over 11 column volumes to give 867.4mg (74.9%) of the title compound as a yello[0178] w solid. XH NMR (500 MHz, CC13D) delta ppm 8.64 (1 H, dd, J=4.58, 1.53 Hz), 8.09-8.25 (3 H, m), 7.65 (1 H, d, J=4.58 Hz), 7.37 (1 H, dd, J=7.93, 4.58 Hz). LC/MS (Condition B): ret. T = 3.2min, (M+H)+ 400.81, 402.81.
  • 7
  • [ 20576-82-3 ]
  • [ 54231-41-3 ]
  • [ 1357196-12-3 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 18h; Step B: fert-butyl 4- [2- (3 -bromopyr idin-2-yl')hydrazinyl1 carbonyl I benzoateTo a 250 one neck round bottom flask was charged with 4-tert-butoxycarbonylbenzoic acid (1000 mg, 4.50 mmol) along with HOBT (912 mg 6.75 mmol) and EDC (1294 rag, 6.75 mmol) in CH2CI2 (40 ml) before the addition of 3-bromo-2-hydraziiiylpyridine (846 mg, 4.50 mmol). The mixture was stirred at room temperature for 18 hrs overnight. LC-MS showed complete coupling and the mixture was concentrated by rotary evaporation. The residue was then suspended in ethyl acetate (15 mL) and water (50 mL) and stirred for 1 hour. The solid was filtered and washed with water 3 times and dried under vacuum for 4 hours for afford white solid product fert-butyl 4-[2-(3-bromopyridin-2-yl)hydrazinyl]carbonyl}berizoate. LC-MS (Es, m/z): CnHigBrNsOa: 391; Found: 392 [M+H]+.
  • 8
  • [ 54231-41-3 ]
  • [ 530-62-1 ]
  • [ 1207970-25-9 ]
YieldReaction ConditionsOperation in experiment
35% In tetrahydrofuran for 2h; 1 8-bromo-ri.2.41triazolor4.3-alpyridin-3r2H -one ri-5^ To a solution of 1-4 (5.0 g, 26.6 mmol) in THF (50 mL) was added carbonyldiimidazole (5.61 g, 34.6 mmol), and the heterogeneous mixture was stirred for 2 h. The reaction was diluted with water (150 mL) and EtOAc (150 mL), causing a precipitate to form. The mixture was filtered through a sintered glass filter, yielding 2.0 g (35%) of 1-5 as a tan solid. 1H NMR (300 MHz, OMSO-d6) δ 12.73 (s, 1 H), 7.88 (dd, J= 7.2, 0.9 Hz, 1 H), 7.58 (dd, J= 7.2, 0.9 Hz, 1 H), 6.51 (app t, J= 7.2 Hz, 1 H).
  • 9
  • [ 5333-86-8 ]
  • [ 54231-41-3 ]
  • [ 54230-91-0 ]
YieldReaction ConditionsOperation in experiment
91% With sodium acetate; acetic acid In ethanol at 50℃; for 3.5h; 8-Bromo-3-phenyl-[1,2,4]triazolo[4,3-a]pyridine (1f) To a mixture of ethyl benzimidate hydrochloride(5b), 1.00 g, 5.22 mmol, 1 equiv.), 3-bromo-2-hydrazinopyridine(4f), 982 mg, 5.22 mmol,1.00 equiv.) and anhydrous sodium acetate (433 mg, 5.22 mmol, 1.00 equiv) was added absolute ethanol (SDA 3C, 5.00 mL) followed by acetic acid (150 µL, 2.61mmol, 0.50 equiv). The heterogeneous mixture was heated to 50 °C for 3.5 h.The slurry was cooled to room temperature and concentrated in vacuo to afford a yellow residue which was partitioned between dichloromethane (50 mL)and saturated aqueous sodium bicarbonate (25 mL). The layers were separated and the aqueous layer was extracted with dichloromethane (25 mL). The combined organic extracted were dried over sodium sulfate, filtered and concentrated in vacuo to afford a yellow solid. The solid was purified by flash column chromatography over silica gel (0 → 5 % methanol in dichloromethane gradient) to afford 1f as a white solid (1.31 g, 91 %). A duplicate experiment afforded 1.26 g (88 %) of product.1H NMR (500 MHz, DMSO-d6, 23 °C): δ 8.56 (d, J = 6.9 Hz, 1H), 7.89 (app dd, J = 7.8, 1.8, 2H), 7.78 (d, J = 7.2 Hz, 1H), 7.59-7.65 (m, 3H), 6.93(t, J = 6.9 Hz, 1H).13C NMR (125.8 MHz, DMSO-d6, 23 °C): δ 148.3, 147.7,130.4, 130.2, 129.2, 128.2, 126.2, 123.6, 114.7, 108.4.FTIR(thin film) (cm-1):3079(w), 1493 (m), 1303 (w), 1072 (m), 778 (s).HRMS(ESI) (m/z):Calc’dfor C12H9BrN3 [M+H]+: 273.9974,Found:273.9965.Melting Point:181-182°C.
  • 10
  • [ 54231-41-3 ]
  • [ 1140898-82-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / 1.17 h / 0 °C 1.2: 2.42 h / 0 - 20 °C 2.1: triphenylphosphine; N-ethyl-N,N-diisopropylamine; tetrachloromethane / tetrahydrofuran / 16 h / 0 - 20 °C
Multi-step reaction with 2 steps 1.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / 1.17 h / 0 °C 1.2: 16 h / 0 - 20 °C 2.1: trichlorophosphate / toluene / 18 h / Reflux
Multi-step reaction with 2 steps 1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / Inert atmosphere 2: trichlorophosphate / toluene / Inert atmosphere
Multi-step reaction with 2 steps 1.1: 4-methyl-morpholine / tetrahydrofuran / 1 h / 0 °C 1.2: 2.25 h / 0 - 20 °C 2.1: N-ethyl-N,N-diisopropylamine; triethylphosphine / tetrahydrofuran; tetrachloromethane / 0 - 20 °C

  • 11
  • [ 54231-41-3 ]
  • [ 1610951-46-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / 1.17 h / 0 °C 1.2: 2.42 h / 0 - 20 °C 2.1: triphenylphosphine; N-ethyl-N,N-diisopropylamine; tetrachloromethane / tetrahydrofuran / 16 h / 0 - 20 °C 3.1: caesium carbonate / 120 °C
  • 12
  • [ 54231-41-3 ]
  • [ 1610951-50-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / 1.17 h / 0 °C 1.2: 2.42 h / 0 - 20 °C 2.1: triphenylphosphine; N-ethyl-N,N-diisopropylamine; tetrachloromethane / tetrahydrofuran / 16 h / 0 - 20 °C 3.1: caesium carbonate / N,N-dimethyl-formamide / 3 h / 180 °C / Microwave irradiation
  • 13
  • [ 54231-41-3 ]
  • [ 1610951-54-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / 1.17 h / 0 °C 1.2: 2.42 h / 0 - 20 °C 2.1: triphenylphosphine; N-ethyl-N,N-diisopropylamine; tetrachloromethane / tetrahydrofuran / 16 h / 0 - 20 °C 3.1: caesium carbonate / 120 °C
  • 14
  • [ 54231-41-3 ]
  • [ 1610951-60-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / 1.17 h / 0 °C 1.2: 2.42 h / 0 - 20 °C 2.1: triphenylphosphine; N-ethyl-N,N-diisopropylamine; tetrachloromethane / tetrahydrofuran / 16 h / 0 - 20 °C 3.1: caesium carbonate / 120 °C
  • 15
  • [ 54231-41-3 ]
  • [ 1310692-29-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / 1.17 h / 0 °C 1.2: 2.42 h / 0 - 20 °C 2.1: triphenylphosphine; N-ethyl-N,N-diisopropylamine; tetrachloromethane / tetrahydrofuran / 16 h / 0 - 20 °C 3.1: caesium carbonate / 120 °C
  • 16
  • [ 54231-41-3 ]
  • [ 1610951-70-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / 1.17 h / 0 °C 1.2: 2.42 h / 0 - 20 °C 2.1: triphenylphosphine; N-ethyl-N,N-diisopropylamine; tetrachloromethane / tetrahydrofuran / 16 h / 0 - 20 °C 3.1: caesium carbonate / 120 °C
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