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Product Details of [ 3034-38-6 ]

CAS No. :3034-38-6 MDL No. :MFCD00005196
Formula : C3H3N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :VYDWQPKRHOGLPA-UHFFFAOYSA-N
M.W : 113.07 Pubchem ID :18208
Synonyms :

Calculated chemistry of [ 3034-38-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 27.41
TPSA : 74.5 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) : 0.05
Log Po/w (XLOGP3) : 0.22
Log Po/w (WLOGP) : 0.32
Log Po/w (MLOGP) : -0.4
Log Po/w (SILICOS-IT) : -0.86
Consensus Log Po/w : -0.13

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.08
Solubility : 9.49 mg/ml ; 0.0839 mol/l
Class : Very soluble
Log S (Ali) : -1.34
Solubility : 5.12 mg/ml ; 0.0453 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.56
Solubility : 31.2 mg/ml ; 0.276 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.04

Safety of [ 3034-38-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P501-P270-P264-P280-P337+P313-P301+P312+P330 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3034-38-6 ]

* 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 [ 3034-38-6 ]
  • Downstream synthetic route of [ 3034-38-6 ]

[ 3034-38-6 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 3034-38-6 ]
  • [ 77-78-1 ]
  • [ 3034-42-2 ]
YieldReaction ConditionsOperation in experiment
82% for 2 h; Reflux 5-Nitroimidazole (2) (1 g, 8.85 mmol) and dimethyl sulfate (1.2 mL) were added in dioxane (5 mL). Reaction mixture was refluxed for 2 h. The solvent was then evaporated under vacuum, and the oily acidic residue was neutralized by a NaHCO3 saturated aqueous solution. The formed solid and the aqueous solution were extracted with dichloromethane (3 x 5 mL). Mixture was dried with magnesium sulfate and organic solvent evaporated on vacuum, crude was purified using flash column chromatography (dichloromethane/ethylacetate; 97:3) to obtained 1-Methyl-5-nitro-1H-imidazole (4a) (0.92 g, 82percent); m.p. 60 °C.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 3, p. 1015 - 1018
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 5, p. 1274 - 1278
[3] Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 427 - 440
  • 2
  • [ 3034-38-6 ]
  • [ 3034-42-2 ]
YieldReaction ConditionsOperation in experiment
82% With dimethyl sulfate In formic acid; water EXAMPLE 2
202 parts of 5-nitroimidazole is dissolved in 600 parts of formic acid (90percent by weight), 250 parts of dimethyl sulfate is added and the whole is heated for 6 hours.
The formic acid is distilled off in vacuo.
420 parts of water is added to the residue, the whole cooled to from 0° to 5° C. and the unreacted 5-nitroimidazole (60 parts) is centrifuged off.
The mixture is adjusted to pH 10 with aqueous ammonia solution (25percent by weight) and the precipitate is separated at 0° to 5° C. 130 parts of 1-methyl-5-nitroimidazole having a melting point of 58° to 60° C. is obtained; this is equivalent to a yield of 82percent of theory based on reacted 4(5)-nitroimidazole.
Reference: [1] Patent: US4021442, 1977, A,
  • 3
  • [ 3034-38-6 ]
  • [ 80-48-8 ]
  • [ 3034-42-2 ]
Reference: [1] Patent: US4010176, 1977, A,
  • 4
  • [ 553-90-2 ]
  • [ 3034-38-6 ]
  • [ 3034-41-1 ]
  • [ 3034-42-2 ]
Reference: [1] Tetrahedron Letters, 1984, vol. 25, # 18, p. 1957 - 1960
  • 5
  • [ 3034-38-6 ]
  • [ 74-88-4 ]
  • [ 3034-42-2 ]
Reference: [1] Chemistry - A European Journal, 2010, vol. 16, # 13, p. 3983 - 3993
  • 6
  • [ 3034-38-6 ]
  • [ 77-78-1 ]
  • [ 3034-41-1 ]
  • [ 3034-42-2 ]
Reference: [1] Liebigs Annalen der Chemie, 1987, p. 77 - 80
[2] Journal of the Chemical Society, 1925, vol. 127, p. 576
[3] Tetrahedron Letters, 1984, vol. 25, # 18, p. 1957 - 1960
  • 7
  • [ 3034-38-6 ]
  • [ 77-78-1 ]
  • [ 3034-42-2 ]
Reference: [1] New Journal of Chemistry, 2006, vol. 30, # 3, p. 349 - 358
[2] Antimicrobial Agents and Chemotherapy, 2003, vol. 47, # 1, p. 302 - 308
[3] Journal of the Chemical Society, 1924, vol. 125, p. 1434
  • 8
  • [ 3034-38-6 ]
  • [ 3034-42-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 2819 - 2828
  • 9
  • [ 186581-53-3 ]
  • [ 60-29-7 ]
  • [ 3034-38-6 ]
  • [ 3034-41-1 ]
  • [ 3034-42-2 ]
Reference: [1] Journal of the Chemical Society, 1925, vol. 127, p. 576
  • 10
  • [ 3034-38-6 ]
  • [ 77-78-1 ]
  • [ 3034-41-1 ]
  • [ 3034-42-2 ]
Reference: [1] Journal of the Chemical Society, 1925, vol. 127, p. 576
  • 11
  • [ 3034-38-6 ]
  • [ 6154-30-9 ]
YieldReaction ConditionsOperation in experiment
88.9% With bromine; sodium hydrogencarbonate In water at 23 - 55℃; for 10 h; A mixture consisting of 4-nitroimidazole (100 g, 884 mmol), sodium bicarbonate (164 g, 1.94 mol), and water (500 ml) was intensively stirred, and thereafter, bromine (106 ml, 2.07 mol) was added dropwise to the mixture at room temperature (23°C to 25°C) over 6 hours (wherein it intensively foamed during the dropping). The thus obtained mixture was further stirred under heating (50°C to 55°C, 4 hours). Thereafter, water (400 ml) and concentrated hydrochloric acid (80 ml) were added thereto under cooling on ice (10°C or lower), and the obtained mixture was stirred for 1 hours. Crystals were collected by filtration. The obtained crystals were washed with water (on a filter paper, with 400 ml of water), dispersedly washed (with 800 ml of water, twice), and air-dried (50°C, 16 hours). Yield: 213 g (Yield: 88. 9percent), pale yellow crystal IR (KBr): 3074,1548, 1468, 1392, 1361,1345, 1310, 1259,1172, 1066,975, 830,667 cm~l.
85.2%
Stage #1: With bromine; sodium hydrogencarbonate In water at 10 - 60℃; for 5 h;
Stage #2: With hydrogenchloride In water at 10℃;
Reference example 1
Preparation of 2,5-dibromo-4-nitroimidazole
To a suspension of water (100 ml), 4-nitroimidazole (25 g) and sodium hydrogencarbonate (40.87 g), was dropwisely added bromine (26.5 ml) at lower than 10°C, the reaction mixture was stirred at 25 to 30°C for 1 hour, and at 50 to 60°C for 4 hours.
Then concentrated hydrochloric acid was added to the reaction mixture at lower than 10°C to adjust pH 1, the crystals separated were collected by filtration, and were washed thoroughly with water.
The crystals were dried at 50°C under a reduced pressure for 24 hours, there was obtained 51.01 g (85.2percent) of 2,5-dibromo-4-nitroimidazole of pale yellow powdery product.
67% With bromine; sodium hydrogencarbonate In water at 40℃; for 2 h; 4-nitroimidazole (25 g, 221 mmol), sodium bicarbonate (37.1 g, 442 mmol) and water (600 mL) for dilution and then bromine (30 mL, 620 mmol) the temperature at the dropwise addition and the reaction mixture was at 40 ° C and reacted for 12 hours. After filtering the solids level of the reaction mixture was washed with toluene three times and dried under reduced pressure to give a yield of 2,5-dibromo-4-nitroimidazole of 39.8 g (67percent). Prepared 2,5-di-bromo-4-nitroimidazole (39.8 g, 149 mmol) and water (450 mL) and then diluted to sodium iodide (223 g, 1486 mmol) was added and stirring under reflux was 12 sigan. Lower the temperature to room temperature, then filtered washing the solids in the reaction mixture with water, dried under reduced pressure to yield 2-bromo-5-iodo of 37.6 g (80percent) was obtained a 4-nitroimidazole. Prepared 2-bromo-5-iodo-4- nitroimidazole (20 g, 63 mmol) in ethanol (190 mL) and then diluted in triethylamine (26.5 mL, 190 mmol) and platinum oxide (108 mg, 0.47 mmol) to give the applied wave after reacting for 3 hours under a hydrogen pressure of 3 bar in the reactor was concentrated under a reduced pressure after filtration with a silica gel and celite. Yield of the reaction mixture with 2-ethyl acetate 10percent washed with hydrochloric acid solution to remove the moisture of the obtained organic layer over anhydrous magnesium sulfate, and then the filtrate was concentrated under reduced pressure and isopropyl alcohol and hexane, to obtain 7.9 g (65percent) and then diluted with to give a-bromo-4-nitroimidazole.
Reference: [1] Patent: WO2005/77913, 2005, A1, . Location in patent: Page/Page column 72-73
[2] Organic Process Research and Development, 2013, vol. 17, # 9, p. 1149 - 1155
[3] Patent: EP1553088, 2005, A1, . Location in patent: Page/Page column 46
[4] Patent: KR101650716, 2016, B1, . Location in patent: Paragraph 0082; 0083
  • 12
  • [ 62-53-3 ]
  • [ 5455-59-4 ]
  • [ 3034-38-6 ]
  • [ 41384-83-2 ]
Reference: [1] Heterocycles, 1994, vol. 37, # 3, p. 1511 - 1520
  • 13
  • [ 3034-38-6 ]
  • [ 98-80-6 ]
  • [ 41384-83-2 ]
YieldReaction ConditionsOperation in experiment
86% With oxygen; sodium hydroxide; copper dichloride In methanol for 18 h; Reflux General procedure: A mixture of 1.6 mmol of C-nitro-NH-azole (1a–e), 2.6 mmol of arylboronic acid (2a-n), 1.6 mmol of sodium hydroxide, 0.2 mmol of CuCl2 and methanol (15 mL) was refluxed while air was bubbled through the reaction mixture. After completion of the reaction, determined on the basis of TLC analysis, the solvent was removed under reduced pressure using a rotary evaporator. The obtained crude product was purified by silica gel column chromatography with 5:95 v/v MeOH/CHCl3 as an eluent to give corresponding N-aryl-C-nitroazole. The product was crystallized from methanol/water.
1.5 g With sodium hydroxide; copper dichloride In methanol at 80℃; for 16 h; To a solution of 4-nitroimidazole (5 g, 44.2 mmol) in MeOH (40 ml) was added phenyl boronic acid (8.77 g, 71.66 mmol) at rt and treated with CuCl2(0.71 g, 5.3 mmol) and NaOH (1.76 g, 44.2 mmol). The reaction mixture was stirred at 80°C for 16 h whilst continuing the slow purging of 02gas throughout the reaction time. The resulting reaction mixture was allowed to cool to rt and the purging of 02gas was removed. The reaction mixture was then concentrated under reduced pressure. The obtained crude material was poured into water (500 ml) and extracted with EtOAc (3 x 150 ml). The combined organic phase was wash with NaHC03solution (200 ml) and dried over Na2S04, filtered and concentrated under reduced pressure to yield 4-nitro-l -phenyl- lH-imidazole (1.5 g, 7.93 mmol), ), LCMS: Method C, 1.76 min, MS: ES+ 191.09.
1.5 g With oxygen; sodium hydroxide; copper dichloride In methanol at 80℃; for 16 h; To a solution of 4-nitroimidazole (5.00 g, 44.2 mmol) in MeOH (40 ml) was added phenylboronic acid (8.77 g, 71.7 mmol), CuC (0.710 g, 5.30 mmol) and NaOH (1.760 g, 44.2 mmol) at rt. The reaction mixture was stirred at 80°C for 16 h whilst slowly purging with O2 gas throughout the reaction time. The resulting mixture was cooled to rt and concentrated under reduced pressure. The obtained crude material was poured into water (500 ml) and extracted with EtOAc (3 x 150 ml). The combined organic phase was wash with NaHCO3 solution (200 ml) and dried over Na2SO4, filtered and concentrated under reduced pressure to yield 4-nitro-1 -phenyl- 1 H-imidazole (1 .500 g, 7.93 mmol). LCMS: Method C, 1 .760 min, MS: ES+ 191 .09.
Reference: [1] Beilstein Journal of Organic Chemistry, 2013, vol. 9, p. 1517 - 1525
[2] Patent: WO2017/109488, 2017, A1, . Location in patent: Page/Page column 41
[3] Patent: WO2018/65768, 2018, A1, . Location in patent: Page/Page column 89
  • 14
  • [ 591-50-4 ]
  • [ 3034-38-6 ]
  • [ 41384-83-2 ]
Reference: [1] Asian Journal of Chemistry, 2013, vol. 25, # 11, p. 6240 - 6242
[2] ChemMedChem, 2015, vol. 10, # 12, p. 2027 - 2041
  • 15
  • [ 62-53-3 ]
  • [ 5455-59-4 ]
  • [ 3034-38-6 ]
  • [ 41384-83-2 ]
Reference: [1] Heterocycles, 1994, vol. 37, # 3, p. 1511 - 1520
  • 16
  • [ 3034-38-6 ]
  • [ 6293-66-9 ]
  • [ 41384-83-2 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 2011, vol. 47, # 1, p. 45 - 54
  • 17
  • [ 62-53-3 ]
  • [ 98-64-6 ]
  • [ 7454-47-9 ]
  • [ 3034-38-6 ]
  • [ 41384-83-2 ]
Reference: [1] Tetrahedron, 1994, vol. 50, # 19, p. 5741 - 5752
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