Home Cart 0 Sign in  

[ CAS No. 1178884-53-1 ]

{[proInfo.proName]}
Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 1178884-53-1
Chemical Structure| 1178884-53-1
Structure of 1178884-53-1 *Storage: {[proInfo.prStorage]}

Quality Control of [ 1178884-53-1 ]

Related Doc. of [ 1178884-53-1 ]

SDS

Product Details of [ 1178884-53-1 ]

CAS No. :1178884-53-1MDL No. :MFCD21364605
Formula : C5H4BrClN2O Boiling Point : -
Linear Structure Formula :-InChI Key :N/A
M.W :223.46Pubchem ID :59216474
Synonyms :

Computed Properties of [ 1178884-53-1 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 1178884-53-1 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1178884-53-1 ]

  • Upstream synthesis route of [ 1178884-53-1 ]

[ 1178884-53-1 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 74-88-4 ]
  • [ 1178884-53-1 ]
YieldReaction ConditionsOperation in experiment
79% With caesium carbonate In N,N-dimethyl-formamide for 3.33 h; Step 3: To a solution of 4-bromo-6-chloropyridazin-3(2H)-one (1.0 equiv.) and Cs2CO3 (1.2 equiv.) in DMF (0.07 M) was added iodomethane (1.5 equiv.) drop-wise over 20 min. The resulting mixture was stirred for 3 h. The reaction mixture was then diluted with ammonium chloride, then extracted with ethyl acetate, dried over MgSO4 and concentrated in vacuo to yield as a brown solid. The oil was further purified via silica gel column chromatography eluting with 100percent heptanes to 80percent ethyl acetate:heptanes to yield 4-bromo-6-chloro-2-methylpyridazin-3(2H)-one as an off-white solid in 79percent yield. LCMS (m/z) (M+H)=222.9/224.9, Rt=0.54 min. 1H NMR (400 MHz, ) δ ppm 3.77-3.86 (m, 3H) 7.56-7.69 (m, 1H).
68%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.17 h; Inert atmosphere
Stage #2: at 20℃; for 1.50 h;
A 250-mL single-necked round bottomed flask equipped with a magnetic stirrer was purged with nitrogen and charged with 4-bromo-6-chloropyridazin-3(2H)-one (1.00 g, 4.77 mmol) and DMF (15 mL). Sodium hydride (60percent by weight in oil, 229 mg, 5.73 mmol) was added in one portion. After stirring at room temperature for 10 minutes, iodomethane (1.02 g, 7.16 mmol) was added and the reaction stirred at room temperature for 1.5 h. The reaction was then quenched with aqueous saturated sodium bicarbonate (10 mL) and the resulting solution poured into water (150 mL). The mixture was then extracted with ethyl acetate (250 mL). The organic layer was dried over sodium sulfate. The drying agent was then removed by filtration, and the filtrate was concentrated under reduced pressure to residue. Purification by column chromatography afforded 103e in a 68percent yield (722 mg) as a white solid: mp 107- 108 °C; ]H NMR (300 MHz, CDC13) δ 7.62 (s, 1H), 3.81 (s, 3H).
68%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.17 h;
Stage #2: at 20℃; for 1.50 h;
A 250-mL single-necked round bottomed flask equipped with a magnetic stirrer was purged with nitrogen and charged with 4-bromo-6-chloropyridazin-3(2H)-one (1.00 g, 4.77 mmol) and DMF (15 mL). Sodium hydride (60percent by weight in oil, 229 mg, 5.73 mmol) was added in one portion. After stirring at room temperature for 10 minutes, iodomethane (1.02 g, 7.16 mmol) was added and the reaction stirred at room temperature for 1.5 h. The reaction was then quenched with aqueous saturated sodium bicarbonate (10 mL) and the resulting solution poured into water (150 mL). The mixture was then extracted with ethyl acetate (250 mL). The organic layer was dried over sodium sulfate. The drying agent was then removed by filtration, and the filtrate was concentrated under reduced pressure to residue. Purification by column chromatography afforded 103a in a 68percent yield (722 mg) as a white solid: mp 107- 108 °C; ]H NMR (300 MHz, CDC13) δ 7.62 (s, 1H), 3.81 (s, 3H).
Reference: [1] Patent: US2014/275003, 2014, A1. Location in patent: Paragraph 0215; 0218
[2] Patent: WO2011/140488, 2011, A1. Location in patent: Page/Page column 128
[3] Patent: WO2012/30990, 2012, A1. Location in patent: Page/Page column 65
[4] Patent: WO2009/98144, 2009, A1. Location in patent: Page/Page column 68-69
[5] Patent: US2010/222325, 2010, A1. Location in patent: Page/Page column 93
Historical Records

Related Functional Groups of
[ 1178884-53-1 ]

Chlorides

Chemical Structure| 933041-13-5

[ 933041-13-5 ]

4-Bromo-6-chloropyridazin-3(2H)-one

Similarity: 0.87

Chemical Structure| 1114563-59-5

[ 1114563-59-5 ]

6-Chloro-2,5-dimethylpyridazin-3(2H)-one

Similarity: 0.72

Chemical Structure| 19064-67-6

[ 19064-67-6 ]

6-Chloro-3-hydroxypyridazine

Similarity: 0.66

Chemical Structure| 1703-07-7

[ 1703-07-7 ]

6-Chloro-5-methylpyridazin-3(2H)-one

Similarity: 0.61

Chemical Structure| 867130-83-4

[ 867130-83-4 ]

4-Amino-6-chloro-2-phenylpyridazin-3(2H)-one

Similarity: 0.60

Bromides

Chemical Structure| 933041-13-5

[ 933041-13-5 ]

4-Bromo-6-chloropyridazin-3(2H)-one

Similarity: 0.87

Chemical Structure| 5788-58-9

[ 5788-58-9 ]

4,5-Dibromopyridazin-3(2H)-one

Similarity: 0.64

Chemical Structure| 954240-46-1

[ 954240-46-1 ]

4-Bromo-6-methylpyridazin-3(2H)-one

Similarity: 0.64

Chemical Structure| 14305-08-9

[ 14305-08-9 ]

4,5-Dibromo-2-phenylpyridazin-3(2H)-one

Similarity: 0.63

Chemical Structure| 1123169-25-4

[ 1123169-25-4 ]

6-Bromo-2-methylpyridazin-3(2H)-one

Similarity: 0.60

Amides

Chemical Structure| 933041-13-5

[ 933041-13-5 ]

4-Bromo-6-chloropyridazin-3(2H)-one

Similarity: 0.87

Chemical Structure| 1114563-59-5

[ 1114563-59-5 ]

6-Chloro-2,5-dimethylpyridazin-3(2H)-one

Similarity: 0.72

Chemical Structure| 19064-67-6

[ 19064-67-6 ]

6-Chloro-3-hydroxypyridazine

Similarity: 0.66

Chemical Structure| 5788-58-9

[ 5788-58-9 ]

4,5-Dibromopyridazin-3(2H)-one

Similarity: 0.64

Chemical Structure| 954240-46-1

[ 954240-46-1 ]

4-Bromo-6-methylpyridazin-3(2H)-one

Similarity: 0.64

Related Parent Nucleus of
[ 1178884-53-1 ]

Pyridazines

Chemical Structure| 933041-13-5

[ 933041-13-5 ]

4-Bromo-6-chloropyridazin-3(2H)-one

Similarity: 0.87

Chemical Structure| 1114563-59-5

[ 1114563-59-5 ]

6-Chloro-2,5-dimethylpyridazin-3(2H)-one

Similarity: 0.72

Chemical Structure| 19064-67-6

[ 19064-67-6 ]

6-Chloro-3-hydroxypyridazine

Similarity: 0.66

Chemical Structure| 5788-58-9

[ 5788-58-9 ]

4,5-Dibromopyridazin-3(2H)-one

Similarity: 0.64

Chemical Structure| 954240-46-1

[ 954240-46-1 ]

4-Bromo-6-methylpyridazin-3(2H)-one

Similarity: 0.64