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[ CAS No. 65373-52-6 ] {[proInfo.proName]}

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Chemical Structure| 65373-52-6
Chemical Structure| 65373-52-6
Structure of 65373-52-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 65373-52-6 ]

CAS No. :65373-52-6 MDL No. :MFCD03412587
Formula : C4H3NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :TYHOSUCCUICRLM-UHFFFAOYSA-N
M.W : 97.07 Pubchem ID :14786609
Synonyms :

Calculated chemistry of [ 65373-52-6 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 21.89
TPSA : 43.1 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.8 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.96
Log Po/w (XLOGP3) : 0.13
Log Po/w (WLOGP) : 0.49
Log Po/w (MLOGP) : -1.44
Log Po/w (SILICOS-IT) : 1.07
Consensus Log Po/w : 0.24

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.99
Solubility : 10.0 mg/ml ; 0.103 mol/l
Class : Very soluble
Log S (Ali) : -0.59
Solubility : 24.9 mg/ml ; 0.256 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.1
Solubility : 7.66 mg/ml ; 0.0789 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.67

Safety of [ 65373-52-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 65373-52-6 ]

* 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 [ 65373-52-6 ]
  • Downstream synthetic route of [ 65373-52-6 ]

[ 65373-52-6 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 288-42-6 ]
  • [ 68-12-2 ]
  • [ 65373-52-6 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h;
Stage #2: at 20℃;
At -78 °C, a solution of F-1 (800mg, 11.58mmol) in THF was treated with 1.6 M solution of n-BuLi in hexanes (7.2 mL, 11.58 mmol). The reaction was stirred for 1 hour, and then a solution of DMF (0.89 mmol, 1 1.58mmol) in THF (8 mL) was added. The reaction was warmed to room temperature and stirred overnight. The reaction mixture was treated with MeOH, filtered through Dowex 50W x 8-200 resin (H+ form, 1 : 1 ratio to oxazole F-1), and washed with MeOH. The combined filtrate was concentrated to obtain the crude aldehyde F-2a, F-ia . This material was then purified by column chromatography (100-200 mesh silica gel, 2percent Et20/CH2C12) to obtain the purified aldehyde (900mg, 80percent) as a light brown liquid (Rf = 0.7(2percent Et20/CH2C12)). This product was used in the next step without any characterization.
Reference: [1] Patent: WO2011/35009, 2011, A1, . Location in patent: Page/Page column 45-46
[2] Patent: WO2008/61109, 2008, A2, . Location in patent: Page/Page column 62
[3] Patent: WO2005/102998, 2005, A1, . Location in patent: Page/Page column 31
[4] Journal of Photochemistry and Photobiology A: Chemistry, 2016, vol. 316, p. 95 - 103
  • 2
  • [ 288-42-6 ]
  • [ 4394-85-8 ]
  • [ 65373-52-6 ]
Reference: [1] Patent: EP1731513, 2006, A1, . Location in patent: Page/Page column 18
[2] Patent: WO2007/37010, 2007, A1, . Location in patent: Page/Page column 32-34
  • 3
  • [ 68-12-2 ]
  • [ 65373-52-6 ]
Reference: [1] Patent: WO2007/34144, 2007, A1, . Location in patent: Page/Page column 93
  • 4
  • [ 154093-80-8 ]
  • [ 68-12-2 ]
  • [ 65373-52-6 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 1, p. 449 - 452
[2] Journal of Organic Chemistry, 1991, vol. 56, # 1, p. 449 - 452
  • 5
  • [ 65373-52-6 ]
  • [ 130551-92-7 ]
YieldReaction ConditionsOperation in experiment
14% at 0 - 20℃; for 1 h; To a solution of F-2a (90 mg, 9.28 mmol) in MeOH (25 mL) was addedNaBH4 (420mg, 11.14mmol) at -0 °C. The mixture was warmed to room temperature and stirred for 1 hour. The reaction mixture was treated with water (25 mL),extracted with EtOAc, washed with brine solution (50 mL), dried (Na2S04), filtered, and evaporated to obtain crude compound F-2. This material was subjected to column chromatography ( 100-200 mesh size silica gel, 50percent EtO Ac/petroleum ether) to obtain the purified product F-2 (160mg, 14percent) as colorless liquid. Rf = 0.4 (50percentEtOAc/petroleum ether).1H-NMR (400MHz, CDC13,): 7.64 (s, 1H), 7.09 (s, 1H), 4.75 (s, 2H). Mass (m/z, APCI positive mode): 100.3 (M++ 1).
Reference: [1] Patent: WO2011/35009, 2011, A1, . Location in patent: Page/Page column 46
[2] Journal of Organic Chemistry, 1991, vol. 56, # 1, p. 449 - 452
[3] Patent: WO2007/34144, 2007, A1, . Location in patent: Page/Page column 93
[4] Patent: WO2005/102998, 2005, A1, . Location in patent: Page/Page column 31-32
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