Home Cart 0 Sign in  
X

[ CAS No. 74733-25-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 74733-25-8
Chemical Structure| 74733-25-8
Chemical Structure| 74733-25-8
Structure of 74733-25-8 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 74733-25-8 ]

Related Doc. of [ 74733-25-8 ]

Alternatived Products of [ 74733-25-8 ]

Product Details of [ 74733-25-8 ]

CAS No. :74733-25-8 MDL No. :MFCD16036860
Formula : C9H7FO3 Boiling Point : -
Linear Structure Formula :- InChI Key :GJYBURAJRAHKAW-UHFFFAOYSA-N
M.W : 182.15 Pubchem ID :18766342
Synonyms :

Calculated chemistry of [ 74733-25-8 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.11
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 43.07
TPSA : 43.37 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) : -6.46 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.81
Log Po/w (XLOGP3) : 1.34
Log Po/w (WLOGP) : 1.85
Log Po/w (MLOGP) : 1.71
Log Po/w (SILICOS-IT) : 2.29
Consensus Log Po/w : 1.8

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.96
Solubility : 2.01 mg/ml ; 0.011 mol/l
Class : Very soluble
Log S (Ali) : -1.85
Solubility : 2.56 mg/ml ; 0.014 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.7
Solubility : 0.363 mg/ml ; 0.00199 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.51

Safety of [ 74733-25-8 ]

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 [ 74733-25-8 ]

* 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 [ 74733-25-8 ]
  • Downstream synthetic route of [ 74733-25-8 ]

[ 74733-25-8 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 87808-48-8 ]
  • [ 128577-47-9 ]
  • [ 74733-25-8 ]
Reference: [1] Patent: US2012/258982, 2012, A1, . Location in patent: Page/Page column 53
  • 2
  • [ 350-28-7 ]
  • [ 128577-47-9 ]
  • [ 74733-25-8 ]
Reference: [1] Patent: US2012/258982, 2012, A1,
  • 3
  • [ 193290-80-1 ]
  • [ 74-88-4 ]
  • [ 74733-25-8 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With sodium hydride In N,N-dimethyl-formamide for 0.5 h;
Stage #2: at 20℃; for 15 h;
To a solution of compound 14C (0.25 g, 1.49 mmol) in DMF (4.5 mL) was added sodium hydride (60 percent in oil, 0.069 g, 1.73 mmol). The reaction was placed under N2, stirred <n="146"/>for 30 minutes, then iodomethane (0.11 mL, 1.74 mmol) was added and reaction was stirred at room temperature for about 15 hours. The reaction mixture was then poured onto IN HCl and extracted with EtOAc several times. The organics were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to provide compound 14D as a wet residue which solidified upon standing (0.23 g, 85percent).
65.9%
Stage #1: With sodium hydride In N,N-dimethyl-formamide for 0.5 h;
Stage #2: for 5 h;
To a solution of 3-fluoro-4-formylbenzoic acid (.350 g, 2.08 mmol) inDMF was added NaH (0.0916 g, 2.29 mmol). The mixture stirred for 30 minutes and iodomethane (0.325 g, 2.29 mmol) was added. This mixture stirred 5 hours. The mixture was poured into IN HCl and extracted with ethyl acetate. The organic layer was washed with sodium bicarbonate and brine. The organics were dried over MgSC^ and concentrated in vacuo. The crude material was purified by chromatography using Ethyl Acetate/Hexanes to give methyl 3-fluoro 4-formyl benzoate (0.25 g, 65.9percent).
Reference: [1] Patent: WO2008/130584, 2008, A1, . Location in patent: Page/Page column 144-145
[2] Patent: WO2013/74641, 2013, A1, . Location in patent: Paragraph 00382
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 17, p. 4804 - 4807
[4] Patent: WO2004/89916, 2004, A1, . Location in patent: Page 22-23
[5] Journal of Medicinal Chemistry, 2009, vol. 52, # 19, p. 5950 - 5966
[6] Patent: EP2526945, 2012, A1, . Location in patent: Page/Page column 35
  • 4
  • [ 128577-47-9 ]
  • [ 74733-25-8 ]
YieldReaction ConditionsOperation in experiment
48% With dimethyl sulfoxide In hexane; dichloromethane; water; ethyl acetate (1)
Methyl 3-fluoro-4-bromomethylbenzoate (80 mg, 0.32 mmol), described in J. Med. Chem., 35(5) 877 (1992), was dissolved in a mixture of anhydrous dimethyl sulfoxide (4.5 ml) and anhydrous dichloromethane (3 ml).
To the solution cooled to 0° C. was added dropwise with stirring triethylamine N-oxide dihydrate (180 mg, 1.62 mmol) and the mixture was stirred at room temperature for 2 hours.
Water was added to the reaction mixture and this mixture was partitioned between a mixture of ethyl acetate and hexane (1:1) and water.
The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure.
The residue was chromatographed on a silica gel column using ethyl acetate-hexane (1:10) as the eluant to give methyl 3-fluoro-4-formylbenzoate (29 mg, yield 48percent) as a white solid. NMR spectrum (400 MHz, CDCl3) δ ppm: 3.97 (3H, s), 7.85 (1H, d, J=11 Hz), 7.9-8.0 (2H, m), 10.43 (1H, s).
Mass spectrum m/z (EI): 182 (M+, 100percent).
Reference: [1] Patent: US2003/176480, 2003, A1,
  • 5
  • [ 87808-48-8 ]
  • [ 128577-47-9 ]
  • [ 74733-25-8 ]
Reference: [1] Patent: US2012/258982, 2012, A1, . Location in patent: Page/Page column 53
  • 6
  • [ 849758-12-9 ]
  • [ 141-53-7 ]
  • [ 74733-25-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2334 - 2356
  • 7
  • [ 74733-29-2 ]
  • [ 74733-25-8 ]
Reference: [1] Patent: US4478849, 1984, A,
  • 8
  • [ 350-28-7 ]
  • [ 74733-25-8 ]
Reference: [1] Bioorganic and medicinal chemistry, 2002, vol. 10, # 9, p. 3013 - 3021
[2] Patent: EP2526945, 2012, A1,
  • 9
  • [ 87808-48-8 ]
  • [ 74733-25-8 ]
Reference: [1] Bioorganic and medicinal chemistry, 2002, vol. 10, # 9, p. 3013 - 3021
  • 10
  • [ 777074-51-8 ]
  • [ 74733-25-8 ]
Reference: [1] Patent: EP2526945, 2012, A1,
  • 11
  • [ 153556-42-4 ]
  • [ 74733-25-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2334 - 2356
  • 12
  • [ 350-28-7 ]
  • [ 128577-47-9 ]
  • [ 74733-25-8 ]
Reference: [1] Patent: US2012/258982, 2012, A1,
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 74733-25-8 ]

Fluorinated Building Blocks

Chemical Structure| 394-35-4

[ 394-35-4 ]

Methyl 2-fluorobenzoate

Similarity: 0.98

Chemical Structure| 2967-93-3

[ 2967-93-3 ]

Methyl 2-fluoro-5-methylbenzoate

Similarity: 0.98

Chemical Structure| 180636-50-4

[ 180636-50-4 ]

Methyl 4-fluoro-3-methylbenzoate

Similarity: 0.98

Chemical Structure| 362601-90-9

[ 362601-90-9 ]

Methyl 2,5-difluorobenzoate

Similarity: 0.96

Chemical Structure| 403-33-8

[ 403-33-8 ]

Methyl 4-fluorobenzoate

Similarity: 0.96

Aryls

Chemical Structure| 394-35-4

[ 394-35-4 ]

Methyl 2-fluorobenzoate

Similarity: 0.98

Chemical Structure| 2967-93-3

[ 2967-93-3 ]

Methyl 2-fluoro-5-methylbenzoate

Similarity: 0.98

Chemical Structure| 180636-50-4

[ 180636-50-4 ]

Methyl 4-fluoro-3-methylbenzoate

Similarity: 0.98

Chemical Structure| 362601-90-9

[ 362601-90-9 ]

Methyl 2,5-difluorobenzoate

Similarity: 0.96

Chemical Structure| 403-33-8

[ 403-33-8 ]

Methyl 4-fluorobenzoate

Similarity: 0.96

Aldehydes

Chemical Structure| 1415124-73-0

[ 1415124-73-0 ]

Methyl 3,5-difluoro-4-formylbenzoate

Similarity: 0.89

Chemical Structure| 85070-58-2

[ 85070-58-2 ]

Methyl 2-fluoro-4-formylbenzoate

Similarity: 0.85

Chemical Structure| 1640117-38-9

[ 1640117-38-9 ]

Ethyl 3-fluoro-4-formylbenzoate

Similarity: 0.84

Chemical Structure| 467442-12-2

[ 467442-12-2 ]

tert-Butyl 3,5-difluoro-4-formylbenzoate

Similarity: 0.82

Chemical Structure| 1639042-39-9

[ 1639042-39-9 ]

(E)-Methyl 3-(3,5-difluoro-4-formylphenyl)acrylate

Similarity: 0.80

Esters

Chemical Structure| 394-35-4

[ 394-35-4 ]

Methyl 2-fluorobenzoate

Similarity: 0.98

Chemical Structure| 2967-93-3

[ 2967-93-3 ]

Methyl 2-fluoro-5-methylbenzoate

Similarity: 0.98

Chemical Structure| 180636-50-4

[ 180636-50-4 ]

Methyl 4-fluoro-3-methylbenzoate

Similarity: 0.98

Chemical Structure| 362601-90-9

[ 362601-90-9 ]

Methyl 2,5-difluorobenzoate

Similarity: 0.96

Chemical Structure| 403-33-8

[ 403-33-8 ]

Methyl 4-fluorobenzoate

Similarity: 0.96