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[ CAS No. 5926-51-2 ] {[proInfo.proName]}

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Chemical Structure| 5926-51-2
Chemical Structure| 5926-51-2
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Product Details of [ 5926-51-2 ]

CAS No. :5926-51-2 MDL No. :MFCD00005519
Formula : C4HBrO3 Boiling Point : -
Linear Structure Formula :- InChI Key :YPRMWCKXOZFJGF-UHFFFAOYSA-N
M.W : 176.95 Pubchem ID :80027
Synonyms :

Calculated chemistry of [ 5926-51-2 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 28.11
TPSA : 43.37 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.83 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.8
Log Po/w (XLOGP3) : 0.77
Log Po/w (WLOGP) : 0.35
Log Po/w (MLOGP) : 0.42
Log Po/w (SILICOS-IT) : 1.32
Consensus Log Po/w : 0.73

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.42
Solubility : 6.69 mg/ml ; 0.0378 mol/l
Class : Very soluble
Log S (Ali) : -1.26
Solubility : 9.7 mg/ml ; 0.0548 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.11
Solubility : 13.8 mg/ml ; 0.078 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.41

Safety of [ 5926-51-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5926-51-2 ]

* 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.

  • Upstream synthesis route of [ 5926-51-2 ]
  • Downstream synthetic route of [ 5926-51-2 ]

[ 5926-51-2 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 108-86-1 ]
  • [ 5926-51-2 ]
  • [ 591-20-8 ]
  • [ 95-56-7 ]
  • [ 583-69-7 ]
Reference: [1] Inorganica Chimica Acta, 2016, vol. 444, p. 159 - 165
  • 2
  • [ 101349-74-0 ]
  • [ 5926-51-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1894, vol. 280, p. 209
[2] Chemische Berichte, 1877, vol. 10, p. 1883[3] Justus Liebigs Annalen der Chemie, 1884, vol. 226, p. 15
[4] Chemische Berichte, 1897, vol. 30, p. 2887
  • 3
  • [ 584-99-6 ]
  • [ 5926-51-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1861, vol. Suppl.1, p. 368
[2] Justus Liebigs Annalen der Chemie, 1928, vol. 461, p. 168
  • 4
  • [ 108-31-6 ]
  • [ 5926-51-2 ]
Reference: [1] Zhurnal Obshchei Khimii, 1954, vol. 24, p. 1216,1219; engl. Ausg. S. 1205, 1206
  • 5
  • [ 644-80-4 ]
  • [ 5926-51-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1879, vol. 195, p. 67
  • 6
  • [ 107523-13-7 ]
  • [ 802294-64-0 ]
  • [ 5926-51-2 ]
  • [ 120-12-7 ]
Reference: [1] Journal of Organic Chemistry, 1956, vol. 21, p. 673,676
[2] Journal of Organic Chemistry, 1956, vol. 21, p. 673,676
  • 7
  • [ 644-80-4 ]
  • [ 5926-51-2 ]
  • [ 7732-18-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1879, vol. 195, p. 67
[2] Chemische Berichte, 1877, vol. 10, p. 1883[3] Justus Liebigs Annalen der Chemie, 1884, vol. 226, p. 15
  • 8
  • [ 608-36-6 ]
  • [ 108-24-7 ]
  • [ 5926-51-2 ]
  • [ 506-96-7 ]
  • [ 64-19-7 ]
Reference: [1] Chemische Berichte, 1877, vol. 10, p. 1883[2] Justus Liebigs Annalen der Chemie, 1884, vol. 226, p. 15
  • 9
  • [ 45669-18-9 ]
  • [ 5926-51-2 ]
  • [ 10035-10-6 ]
Reference: [1] Chemische Berichte, 1880, vol. 13, p. 1670
  • 10
  • [ 608-36-6 ]
  • [ 10026-13-8 ]
  • [ 5926-51-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1894, vol. 280, p. 209
  • 11
  • [ 584-99-6 ]
  • [ 5926-51-2 ]
  • [ 7732-18-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1861, vol. Suppl.1, p. 368
  • 12
  • [ 5926-51-2 ]
  • [ 15456-86-7 ]
YieldReaction ConditionsOperation in experiment
87% With hydrazinium sulfate In water at 100℃; for 19 h; Hydrazine sulfate (2.25 g. 17,2 mmol) was dissolved in boiling water (20 ml.) with stirring. To this solution, bromomaieic anhydride (2.6mL, 28.2 mmol) was added dropwise via addition funnel, the mixture heated ( 100 °C) under reflux for 19 h, then cooled to ambient temperature. The resulting white precipitate was filtered on a medium frit sintered glass funnel, washed with acetone (3 x 5ml), and air dried in vacuo to give the desired product 4-bromo-l,2- dihydropyridazine--3,6-dione (2.85 g) as a white powder in 87percent yield (gravimetric) with a melting point of 262 °C.
83% With hydrazinium sulfate In water at 90℃; for 4 h; To a solution of N2H4·H2SO4 (3.7 g, 28.3 mmol) in H2O (50 mL) was added dropwise compound 1 (5 g, 28.3 mmol), and the mixture was stirred at 90 °C for 4 h. After the reaction, it was filtered to get compound 2 (4.5 g, yield: 83percent). 1H-NMR (DMSO-d6, 400 MHz,) δ 12.47 (s, 1H), 11.17 (s, 1H), 7.62 (s, 1H).
77% With hydrazine hydrate In tetrahydrofuran a
4-Bromo-1,2-dihydropyridazine-3,6-dione
Hydrazine hydrate (28 ml, 576 mmol) was added dropwise to a stirred solution of bromomaleic anhydride (100 g, 565 mmol) in THF (1l) cooled in an ice-bath so that the internal temperature did not exceed 10° C.
After complete addition of the hydrazine the mixture was refluxed for 18 h.
Solvent was removed by evaporation and the residues were dried by azeotroping with toluene.
The residue was triturated and washed with diethyl ether to give the title compound as an orange solid (83 g, 77percent).
1H NMR (250 MHz, d6-DMSO) δ7.68 (1H, br s). MS (ES+) m/e 193 [MH]+, 191 [MH]+.
This material was used without further purification.
77% With hydrazine hydrate In tetrahydrofuran a
4-Bromo-1,2-dihydropyridazine-3,6-dione
Hydrazine hydrate (28 ml, 576 mmol) was added dropwise to a stirred solution of bromomaleic anhydride (100 g, 565 mmol) in THF (1 l) cooled in an ice-bath so that the internal temperature did not exceed 10° C.
After complete addition of the hydrazine the mixture was refluxed for 18 h.
Solvent was removed by evaporation and the residues were dried by azeotroping with toluene.
The residue was triturated and washed with diethyl ether to give the title compound as an orange solid (83 g, 77percent).
1H NMR (250 MHz, d6-DMSO) δ 7.68 (1H, br s). MS (ES+) m/e 193 [MH]+, 191 [MH]+.
This material was used without further purification.
56% With (x)H2O4S*H4N2 In water at 90℃; for 4 h; To a solution of NH2NH2•H2504 (362 mg, 2.8 mmol) in H20 (5 mL) was added dropwise 3-bromofuran-2,5-dione (500 mg, 2.8 mmol), and the mixture was stirred at 90 °C for 4hours. After the reaction, the mixture was filtered to get 4-bromo-1,2-dihydropyridazine-3,6- dione (300 mg, yield: 56percent). ‘H-NMR (DMSO-d6, 400 MHz) 12.47 (s, 1H), 11.17 (s, 1H), 7.62 (s, 1H). MS (M+H): 191 / 193.
56% With hydrazinium sulfate In water at 90℃; for 4 h; To a solution ofNH2NH2•H2S04 (362 mg, 2.8 mmol) in H20 (5 mL) was addeddropwise 3-bromofuran-2,5-dione (500 mg, 2.8 mmol), and the mixture was stirred at 90 °C for 410 hours. After the reaction, the mixture was filtered to get 4-bromo-1,2-dihydropyridazine-3,6-dione (300 mg, yield: 56percent). 1H-NMR (DMSO-d6, 400 MHz) 8 12.47 (s, 1H), 11.17 (s, 1H),7.62 (s, 1H). MS (M+Ht: 191 I 193.
37% With sodium acetate; hydrazine hydrate In water; acetic acid a)
4-Bromo-1,2-dihydropyridazine-3,6-dione
A mixture of bromomaleic anhydride (50 g, 283 mmol) and sodium acetate (76.5 g, 562 mmol) in 40percent acetic acid/water (750 ml) was treated with hydrazine monohydrate (16.5 ml, 339 mmol) at room temperature under nitrogen.
The brown solution was stirred and heated at 100° C. for 18 hours.
Upon cooling the mixture was poured into water (1 l) and extracted with ethyl acetate (6*500 ml).
The combined extracts were dried (MgSO4), filtered and evaporated to afford the title pyridazine (20 g, 37percent) as an orange solid. 1H NMR (250 MHz, d6-DMSO) 7.68 (br s). MS (ES+) 193 [MH]+, 191 [MH]+.
This material was used without further purification.
37% With sodium acetate; hydrazine hydrate In water; acetic acid a
4Bromo-1,2-dihydropyridazine-3,6-dione
A mixture of bromomaleic anhydride (50 g, 283 mmol) and sodium acetate (76.5 g, 562 mmol) in 40percent acetic acid/water (750 ml) was treated with hydrazine monohydrate (16.5 ml, 339 mmol) at room temperature under nitrogen.
The brown solution was stirred and heated at 100° C. for 18 hours.
Upon cooling the mixture was poured into water (1 l) and extracted with ethyl acetate (6*500 ml).
The combined extracts were dried (MgSO4), filtered and evaporated to afford the title compound (20 g, 37percent) as an orange solid. 1H NMR (250 MHz, d6-DMSO) δ 7.68 (1H, br s). MS (ES+) m/e 193 [MH]+, 191 [MH]+.
This material was used without further purification.
37% With sodium acetate; hydrazine hydrate In water; acetic acid a
4-Bromo-1,2-dihydropyridazine-3,6-dione
A mixture of bromomaleic anhydride (50 g, 283 mmol) and sodium acetate (76.5 g, 562 mmol) in 40percent acetic acid/water (750 ml) was treated with hydrazine monohydrate (16.5 ml, 339 mmol) at room temperature under nitrogen.
The brown solution was stirred and heated at 100° C. for 18 hours.
Upon cooling the mixture was poured into water (11) and extracted with ethyl acetate (6*500 ml).
The combined extracts were dried (MgSO4), filtered and evaporated to afford the title compound (20 g, 37percent) as an orange solid. 1H NMR (250 MHz, d6-DMSO) δ7.68 (1H, br s). MS (ES+) m/e 193 [MH]+, 191 [MH]+.
This material was used without further purification.

Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10311 - 10322
[2] Patent: WO2014/145485, 2014, A2, . Location in patent: Paragraph 00207; 00290
[3] Tetrahedron Letters, 2017, vol. 58, # 14, p. 1373 - 1375
[4] Patent: US6579875, 2003, B1,
[5] Patent: US6303605, 2001, B1,
[6] Nucleosides and Nucleotides, 1994, vol. 13, # 1-3, p. 459 - 479
[7] Patent: WO2014/123793, 2014, A1, . Location in patent: Page/Page column 90
[8] Patent: WO2014/121416, 2014, A1, . Location in patent: Page/Page column 90
[9] Patent: US6319924, 2001, B1,
[10] Patent: US6255305, 2001, B1,
[11] Patent: US6699859, 2004, B1,
[12] Zhurnal Obshchei Khimii, 1954, vol. 24, p. 1216,1219; engl. Ausg. S. 1205, 1206
[13] Patent: US6291460, 2001, B1,
[14] Patent: WO2007/71936, 2007, A1, . Location in patent: Page/Page column 72
[15] Patent: WO2008/3690, 2008, A1, . Location in patent: Page/Page column 34
[16] Patent: WO2008/6648, 2008, A1, . Location in patent: Page/Page column 53
[17] Patent: US2010/56502, 2010, A1, . Location in patent: Page/Page column 16-17
[18] Patent: US2008/221110, 2008, A1, . Location in patent: Page/Page column 18
[19] Heterocyclic Communications, 2015, vol. 21, # 4, p. 215 - 218
[20] Patent: WO2007/115947, 2007, A1, . Location in patent: Page/Page column 30
[21] Patent: WO2008/9700, 2008, A1, . Location in patent: Page/Page column 38
[22] Patent: WO2008/128953, 2008, A1, . Location in patent: Page/Page column 31-32
[23] Patent: WO2008/128961, 2008, A1, . Location in patent: Page/Page column 54
[24] Patent: WO2008/128942, 2008, A1, . Location in patent: Page/Page column 123
  • 13
  • [ 5926-51-2 ]
  • [ 10034-93-2 ]
  • [ 15456-86-7 ]
Reference: [1] Patent: EP1980251, 2008, A1,
  • 14
  • [ 5926-51-2 ]
  • [ 1122-12-9 ]
Reference: [1] Zhurnal Obshchei Khimii, 1954, vol. 24, p. 1216,1219; engl. Ausg. S. 1205, 1206
  • 15
  • [ 5926-51-2 ]
  • [ 6082-66-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 10, p. 2464 - 2469
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