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[ CAS No. 35344-95-7 ] {[proInfo.proName]}

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Chemical Structure| 35344-95-7
Chemical Structure| 35344-95-7
Structure of 35344-95-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 35344-95-7 ]

CAS No. :35344-95-7 MDL No. :MFCD02179514
Formula : C4H4N2O Boiling Point : -
Linear Structure Formula :- InChI Key :LRGBDJBDJXZTTD-UHFFFAOYSA-N
M.W : 96.09 Pubchem ID :5130673
Synonyms :

Calculated chemistry of [ 35344-95-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 23.98
TPSA : 45.75 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) : -7.56 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.23
Log Po/w (XLOGP3) : -0.95
Log Po/w (WLOGP) : 0.22
Log Po/w (MLOGP) : -1.04
Log Po/w (SILICOS-IT) : 1.2
Consensus Log Po/w : -0.07

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.3
Solubility : 48.2 mg/ml ; 0.501 mol/l
Class : Very soluble
Log S (Ali) : 0.47
Solubility : 286.0 mg/ml ; 2.98 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -1.1
Solubility : 7.69 mg/ml ; 0.08 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 35344-95-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 35344-95-7 ]

* 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 [ 35344-95-7 ]
  • Downstream synthetic route of [ 35344-95-7 ]

[ 35344-95-7 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 35344-95-7 ]
  • [ 74-88-4 ]
  • [ 25016-11-9 ]
YieldReaction ConditionsOperation in experiment
87% With caesium carbonate In N,N-dimethyl-formamide at 60℃; To a solution of lH-pyrazole-4-carbaldehyde (1.00 g, 10.4 mmol) in DMF (40 mL) was added iodomethane (1.48 g, 10.4 mmol) and CS2CO3 (10 g, 31.2 mmol). After stirring at 60°C overnight, the reaction mixture was added water (20 mL) and extracted with EtOAc (50 mL x 3). The organic phase was washed with brine, dried over Na2S04 and concentrated to give intermediate 48 (1.00 g, 87percent yield).
Reference: [1] Patent: WO2018/50684, 2018, A1, . Location in patent: Page/Page column 67
  • 2
  • [ 25222-43-9 ]
  • [ 35344-95-7 ]
Reference: [1] Patent: WO2017/40449, 2017, A1, . Location in patent: Paragraph 00175
  • 3
  • [ 37622-90-5 ]
  • [ 35344-95-7 ]
Reference: [1] European Journal of Organic Chemistry, 2012, # 2, p. 260 - 263
  • 4
  • [ 68-12-2 ]
  • [ 591-86-6 ]
  • [ 35344-95-7 ]
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 152, p. 235 - 252
  • 5
  • [ 18655-47-5 ]
  • [ 35344-95-7 ]
Reference: [1] Journal of Materials Chemistry, 2006, vol. 16, # 26, p. 2736 - 2745
[2] Bulletin de la Societe Chimique de France, 1990, # 5, p. 660 - 666
[3] Bulletin de la Societe Chimique de France, 1990, # 5, p. 660 - 666
[4] European Journal of Organic Chemistry, 2004, # 11, p. 2367 - 2374
  • 6
  • [ 153687-35-5 ]
  • [ 35344-95-7 ]
Reference: [1] Patent: WO2005/813, 2005, A1, . Location in patent: Page 36
  • 7
  • [ 2075-45-8 ]
  • [ 68-12-2 ]
  • [ 35344-95-7 ]
Reference: [1] Journal of Materials Chemistry, 2006, vol. 16, # 26, p. 2736 - 2745
  • 8
  • [ 824-94-2 ]
  • [ 35344-95-7 ]
  • [ 153687-35-5 ]
YieldReaction ConditionsOperation in experiment
93.3% With potassium carbonate In acetonitrile for 1 h; Reflux To a mixture of 1H-pyrazole-4-carbaldehyde (100 mg, 1.04 mmol) and 1- (chloromethyl)-4-methoxybenzene (162 mg, 1.04 mmol) in CH3CN (6 mL) was added potassium carbonate (287 mg, 2.08 mmol), the resulting mixture was stirred at reflux for 1 h. The mixture was poured into water (20 mL) and extracted with EtOAc (3×20 mL). The organic layer was dried over Na2SO4and concentrated to give 1-(4-methoxybenzyl)- 1H-pyrazole-4-carbaldehyde (220 mg, 93.3 percent) as a colorless oil
Reference: [1] Patent: KR2017/45749, 2017, A, . Location in patent: Paragraph 1087; 1090-1092
  • 9
  • [ 24424-99-5 ]
  • [ 35344-95-7 ]
  • [ 821767-61-7 ]
YieldReaction ConditionsOperation in experiment
76% at 20℃; for 0.5 h; 4-FORMYL-PYRAZOLE-1-CARBOXYLIC acid tert-butyl ester (56). To a solution of 55 (0.31 g, 3.26 mmol) in acetonitrile (30 ml) was added BOC anhydride (0.71 g, 3.26 mmol) followed by DMAP (0.02 g). After 30 minutes of stirring at room temperature, the solvent was evaporated, water and EtOAc were added. Organic layer was separated, washed with 0.5 N HCl (10 ml) and brine (15 ml), dried (NA2S04) and concentrated to give 0.41 g (76percent yield) of the desired product which was used in the next step to prepare di-Boc-protected 2 without purification.
71% With dmap In acetonitrile at 20℃; 1003831 Step A: Boc2O (2183 mg, 10.0 mmol) was added to a stirred solution of iHpyrazole-4-carbaldehyde (961 mg, 10.0 mmol) in acetonitrile (30 mL) at room temperature, followed by 4-dimethylaminopyridine (“DMAP”) (61.1 mg, 0.500 mmol). After stirring overnight, the reaction was concentrated to dryness and partitioned between ethyl acetate (30 mL) and water (30 mL). The organics were isolated and washed with 0.5N HCL (30 mL) and with brine (30 mL). The organics were isolated, dried (Mg504), filtered and concentratedan oil, which was loaded onto a Biotage 40M column with 4/1 hexanes/ethyl acetate and eluted with the same solvent. Product containing fractions were pooled and concentratedan oil, which eventually solidified to a solid, tert-butyl 4-formyl-1H-pyrazole-1-carboxylate(1.4 g, 71percent).
Reference: [1] Patent: WO2005/813, 2005, A1, . Location in patent: Page 36
[2] Patent: WO2013/130976, 2013, A1, . Location in patent: Paragraph 00383
  • 10
  • [ 35344-95-7 ]
  • [ 6482-24-2 ]
  • [ 304693-70-7 ]
YieldReaction ConditionsOperation in experiment
65% With caesium carbonate In N,N-dimethyl-formamide at 60℃; To a solution of lH-pyrazole-4-carbaldehyde (500 mg, 5.20 mmol) in DMF (20 mL) was added l-bromo-2-methoxyethane (713 mg, 5.2 mmol) and CS2CO3 (3.40 g, 10.4 mmol). After stirring at 60 °C overnight, water (20 mL) was added to the mixture and the mixture was extracted with EtOAc (50 ml x 3). The organic phase was washed with brine, dried over Na2S04 and concentrated to yield intermediate 50 (520 mg, 65percent> yield).
55% With caesium carbonate In acetonitrile for 2 h; Reflux 1H-pyrazole-4-carbaldehyde (0.5 g; 5.2 mmol) and cesium carbonate (3.39 g; 10.4mmol) were diluted in ACN (10 mL). Then, 2-bromoethyl methyl ether (0.636 mL; 6.77 mmol) was added and the reaction mixture was refluxed for 2 hours. The reaction mixture was partitionned between a saturated solution of NaHCO3 and EtOAc. The organic layer was separated, dried over MgSO4, filtered and concentrated.The residue was purified by silica gel chromatography (irregular Si02, 120 g, DCM/MeOH: 100/0 to 95/5). The fractions containing the product were mixed andconcentrated to afford 439 mg (55percent) of intermediate 35.
Reference: [1] Patent: WO2018/50684, 2018, A1, . Location in patent: Page/Page column 68
[2] Patent: WO2018/50686, 2018, A1, . Location in patent: Page/Page column 72; 73
  • 11
  • [ 4333-56-6 ]
  • [ 35344-95-7 ]
  • [ 1082066-00-9 ]
Reference: [1] Patent: WO2008/141020, 2008, A1, . Location in patent: Page/Page column 61
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