Home Cart 0 Sign in  

[ CAS No. 51446-30-1 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 51446-30-1
Chemical Structure| 51446-30-1
Structure of 51446-30-1 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 51446-30-1 ]

Related Doc. of [ 51446-30-1 ]

Alternatived Products of [ 51446-30-1 ]

Product Details of [ 51446-30-1 ]

CAS No. :51446-30-1 MDL No. :MFCD01862084
Formula : C7H5FO3 Boiling Point : -
Linear Structure Formula :- InChI Key :CZNFABVUVHWEJF-UHFFFAOYSA-N
M.W : 156.11 Pubchem ID :2774480
Synonyms :

Calculated chemistry of [ 51446-30-1 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 35.38
TPSA : 57.53 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) : -6.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.76
Log Po/w (XLOGP3) : 1.64
Log Po/w (WLOGP) : 1.65
Log Po/w (MLOGP) : 1.42
Log Po/w (SILICOS-IT) : 1.16
Consensus Log Po/w : 1.33

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.18
Solubility : 1.03 mg/ml ; 0.00663 mol/l
Class : Soluble
Log S (Ali) : -2.46
Solubility : 0.54 mg/ml ; 0.00346 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.46
Solubility : 5.4 mg/ml ; 0.0346 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.16

Safety of [ 51446-30-1 ]

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 [ 51446-30-1 ]

* 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 [ 51446-30-1 ]
  • Downstream synthetic route of [ 51446-30-1 ]

[ 51446-30-1 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 1084801-91-1 ]
  • [ 51446-30-1 ]
YieldReaction ConditionsOperation in experiment
91% With lithium hydroxide monohydrate In tetrahydrofuran; water at 20℃; for 16 h; STEP 1 : 2-FLUORO-5-HYDROXYBENZOIC ACID
[00248] To a solution of methyl 2-fluoro-5-hydroxybenzoate (30.0 g, 176.47 mmol, 1.0 equiv, F-chemicals) in THF:H20 (3: 1, 350 mL) was added LiOH.H20 (22.2 g, 529.41 mmol, 3.0 equiv) at room temperature. The reaction mixture was stirred for 16 h at room temperature. The THF was removed from the reaction mixture, diluted with cold water; pH was adjusted to about 3 with 1.5 N aqueous HC1, extracted with EtOAc (3 x 250 mL). The combined extracts were washed with brine (150 mL), dried over anhydrous Na2S04, filtered and evaporated to afford 2-fluoro-5-hydroxybenzoic acid as an off white solid (25.1 g, 91 percent> yield). MS m/z: [M- 1]"= 155.4.
Reference: [1] Patent: WO2015/51043, 2015, A1, . Location in patent: Paragraph 00248
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 17, p. 7818 - 7839
  • 2
  • [ 367-83-9 ]
  • [ 51446-30-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 4, p. 611 - 626
[2] Patent: US5523475, 1996, A,
[3] Patent: WO2008/57280, 2008, A1, . Location in patent: Page/Page column 34
[4] Patent: WO2005/113494, 2005, A2, . Location in patent: Page/Page column 117
  • 3
  • [ 146328-85-0 ]
  • [ 51446-30-1 ]
YieldReaction ConditionsOperation in experiment
87%
Stage #1: for 1 h; Reflux
Stage #2: Reflux
Na2CO3 (1 eq.) was added to a degassed souUon of water (0.35 M) and the appropriatebromobenzoc acid (1 eq.) and was refluxed for 30 minutes. A further portion of Na2CO3 (1.5eq.) was added to the reaction and refluxed for a further 30 mnutes. Separat&y CuBr2 (0.1 eq.) and trans-N, W-dmethycycohexane-1 ,2-damne (0.2 eq.) were added to degassed water (0.04 M) and an ntense bue coour was observed. This mixture was added to the refluxng aqueous souton and aflowed to sUr at this temperature overnight. The resuWngsouton was aflowed to coo to room temperature and was acid Wed with conc. HC and extracted nto EtOAc. The organcs were dried with MgSO4, ffltered, and the sovent removed in vacuo to give the desired product.The foHowng compounds were made by the Uflmann transformaUon method A Al)H5bromo-2- fluorobenzoc acid (3.5g, 15.98 mmo)Off whte sohd (2.16g, 87percent yed). 1H NMR(400 MHz, DM80) 6 7.18 (dd, J = 6.0, 3.2Hz, 1H), 7,09 (dd, J= 10.5, 8.9 Hz, 1H), 6.98 6.93 (m, 1H). LCM8 B rt 3.19 mn, m/z157.1 [M + H].
Reference: [1] Patent: WO2016/198507, 2016, A1, . Location in patent: Page/Page column 40; 47
  • 4
  • [ 127667-01-0 ]
  • [ 51446-30-1 ]
Reference: [1] Patent: EP2799435, 2014, A1, . Location in patent: Paragraph 0051; 0065; 0066
[2] Patent: US2015/51211, 2015, A1, . Location in patent: Paragraph 0091; 0062
  • 5
  • [ 368422-25-7 ]
  • [ 51446-30-1 ]
Reference: [1] European Journal of Organic Chemistry, 2001, # 15, p. 2911 - 2915
  • 6
  • [ 371-41-5 ]
  • [ 51446-30-1 ]
Reference: [1] European Journal of Organic Chemistry, 2001, # 15, p. 2911 - 2915
  • 7
  • [ 141362-06-3 ]
  • [ 51446-30-1 ]
Reference: [1] European Journal of Organic Chemistry, 2001, # 15, p. 2911 - 2915
  • 8
  • [ 51446-30-1 ]
  • [ 672931-28-1 ]
Reference: [1] Patent: WO2014/52365, 2014, A1,
  • 9
  • [ 67-56-1 ]
  • [ 51446-30-1 ]
  • [ 1084801-91-1 ]
YieldReaction ConditionsOperation in experiment
90% Reflux A solution of 2-fluoro-5-hydroxybenzoic acid (1.5 g, 9.6 mmol) and conc. H2SO4 (0.050 mL, 0.92 mmol) in MeOH (10 mL) was stirred at reflux ON. After evaporation of the solvent, the residue was dissolved in 1N NaOH and extracted 3x with EtOAc. The combined extracts were dried over Na2SO4, filtered and evaporated to give 24B (1.47 g, 90percent yield) as a colorless solid which was used without further purification in the following reaction.1H NMR (500MHz, CDCl3) δ 7.39 (dd, J=5.5, 3.3 Hz, 1H), 7.08 - 7.03 (m, 1H), 7.03 - 6.98 (m, 1H), 3.95 (s, 3H).
833 mg at 0℃; for 2 h; Inert atmosphere; Reflux The obtained 2-fluoro-5-hydroxybenzoic acid (3e) (780 mg, 5 mmol) was dissolved in 100 mL methanol. 1. Thionyl chloride (0.8 mL, 10 mmol) was added dropwise under the condition of ice bath (0°C) and stirring, and then refluxed for two hours. The reaction solution was concentrated, and then column chromatography (petroleum ether : ethyl acetate = 2:1) was performed to isolate methyl 2-fluoro-5-hydroxybenzoate (3f), 833 mg white solid (yield 98percent). 1H NMR (600 MHz, DMSO-d6) δ 9.73 (s, 1H), 7.20-7.18 (m, 1H), 7.13-7.09 (m, 1H), 6.99- 6.97 (m, 1H), 3.80 (s, 3H); ESI-MS m/z: calculated for 170.04, found 171.25 [M+H]+.
833 mg at 0℃; for 2 h; Reflux The obtained 2-fluoro-5-hydroxybenzoic acid (3e) (780 mg, 5 mmol) was dissolved in 100 mL methanol.
Thionyl chloride (0.8 mL, 10 mmol) was added dropwise under the condition of ice bath (0° C.) and stirring, and then refluxed for two hours.
The reaction solution was concentrated, and then column chromatography (petroleum ether:ethyl acetate=2:1) was performed to isolate methyl 2-fluoro-5-hydroxybenzoate (3f), 833 mg white solid (yield 98percent).
1H NMR (600 MHz, DMSO-d6) δ 9.73 (s, 1H), 7.20-7.18 (m, 1H), 7.13-7.09 (m, 1H), 6.99-6.97 (m, 1H), 3.80 (s, 3H); ESI-MS m/z: calculated for 170.04. found 171.25 [M+H]+.
Reference: [1] Patent: WO2018/5336, 2018, A1, . Location in patent: Page/Page column 98
[2] Patent: EP2799435, 2014, A1, . Location in patent: Paragraph 0051; 0065; 0067
[3] Patent: US2015/51211, 2015, A1, . Location in patent: Paragraph 0091; 0093
[4] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 13, p. 3141 - 3147
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 51446-30-1 ]

Fluorinated Building Blocks

Chemical Structure| 65145-13-3

[ 65145-13-3 ]

2-Fluoro-4-hydroxybenzoic acid

Similarity: 0.98

Chemical Structure| 67531-86-6

[ 67531-86-6 ]

2-Fluoro-6-hydroxybenzoic acid

Similarity: 0.93

Chemical Structure| 1084801-91-1

[ 1084801-91-1 ]

Methyl 2-fluoro-5-hydroxybenzoate

Similarity: 0.93

Chemical Structure| 214917-68-7

[ 214917-68-7 ]

2,6-Difluoro-4-hydroxybenzoic acid

Similarity: 0.91

Chemical Structure| 887267-08-5

[ 887267-08-5 ]

3-Fluoro-5-hydroxy-4-methylbenzoic acid

Similarity: 0.91

Aryls

Chemical Structure| 65145-13-3

[ 65145-13-3 ]

2-Fluoro-4-hydroxybenzoic acid

Similarity: 0.98

Chemical Structure| 67531-86-6

[ 67531-86-6 ]

2-Fluoro-6-hydroxybenzoic acid

Similarity: 0.93

Chemical Structure| 1084801-91-1

[ 1084801-91-1 ]

Methyl 2-fluoro-5-hydroxybenzoate

Similarity: 0.93

Chemical Structure| 214917-68-7

[ 214917-68-7 ]

2,6-Difluoro-4-hydroxybenzoic acid

Similarity: 0.91

Chemical Structure| 887267-08-5

[ 887267-08-5 ]

3-Fluoro-5-hydroxy-4-methylbenzoic acid

Similarity: 0.91

Carboxylic Acids

Chemical Structure| 65145-13-3

[ 65145-13-3 ]

2-Fluoro-4-hydroxybenzoic acid

Similarity: 0.98

Chemical Structure| 67531-86-6

[ 67531-86-6 ]

2-Fluoro-6-hydroxybenzoic acid

Similarity: 0.93

Chemical Structure| 214917-68-7

[ 214917-68-7 ]

2,6-Difluoro-4-hydroxybenzoic acid

Similarity: 0.91

Chemical Structure| 887267-08-5

[ 887267-08-5 ]

3-Fluoro-5-hydroxy-4-methylbenzoic acid

Similarity: 0.91

Chemical Structure| 2991-28-8

[ 2991-28-8 ]

2,5-Difluorobenzoic acid

Similarity: 0.89