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2,2-difluorobenzo[d][1,3]dioxole
(2,2-Difluorobenzo[d][1,3]dioxol-4-yl)boronic acid
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2,2-difluorobenzo[d][1,3]dioxole
dioxol

[ CAS No. 126120-87-4 ] (2,2-Difluorobenzo[d][1,3]dioxol-4-yl)boronic acid

Cat. No.: A503032
Chemical Structure| 126120-87-4
Chemical Structure| 126120-87-4
 Structure of 126120-87-4 * Storage: Inert atmosphere,2-8°C
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* Storage: Inert atmosphere,2-8°C

For Research Only 120K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 126120-87-4 ]

COA NMR CNMR HPLC LC-MS

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Specification
Alternatived Products of [ 126120-87-4 ]
Product Citations

Product Details of [ 126120-87-4 ]

CAS No. :126120-87-4 MDL No. :MFCD08062343
Formula : C7H5BF2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :GCIIKWAIWSFGLA-UHFFFAOYSA-N
M.W : 201.92 Pubchem ID :16427145
Synonyms :

Calculated chemistry of [ 126120-87-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 42.47
TPSA : 58.92 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) : -6.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.41
Log Po/w (WLOGP) : 0.53
Log Po/w (MLOGP) : -0.24
Log Po/w (SILICOS-IT) : -0.28
Consensus Log Po/w : 0.28

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.23
Solubility : 1.19 mg/ml ; 0.00587 mol/l
Class : Soluble
Log S (Ali) : -2.25
Solubility : 1.13 mg/ml ; 0.0056 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.59
Solubility : 5.14 mg/ml ; 0.0255 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.83

Safety of [ 126120-87-4 ]

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

Application In Synthesis of [ 126120-87-4 ]

* 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.

  • Downstream synthetic route of [ 126120-87-4 ]

[ 126120-87-4 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 1583-59-1 ]
  • [ 121-43-7 ]
  • [ 110-18-9 ]
  • [ 126120-87-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; n-butyllithium; sodium chloride; In tetrahydrofuran; Petroleum ether; Step F Preparation of (2,2-difluoro-1,3-benzodioxol-4-yl)boronic acid A solution of n-butyllithium (5.57 mL of a 2.5M solution in hexanes, 13.9 mmol) was added to dry tetrahydrofuran (75 mL) at room temperature under a nitrogen atmosphere. The resulting solution was cooled to -15 C. and N,N,N',N'-tetramethylenediamine (2.10 mL, 13.9 mmol) was added dropwise. The reaction was stirred at -15 C. for 0.5 h and then <strong>[1583-59-1]2,2-difluoro-1,3-benzodioxole</strong> was added dropwise while maintaining the reaction temperature below -10 C. After the addition was complete, the reaction was stirred at -15 C. for 1 h before a solution of trimethylborate (1.58 mL, 13.9 mmol) in dry tetrahydrofuran (5 mL) was added dropwise while maintaining the reaction temperature below -10 C. The reaction mixture was stirred at -10 C. for 1 h and then allowed to come to room temperature while stirring overnight. To the reaction mixture was added a 1N solution of hydrochloric acid and then concentrated hydrochloric acid until the solution was strongly acidic. The acidic solution was poured into water. The resulting mixture was saturated with sodium chloride and extracted with diethyl ether three times. The combined organic extracts were dried (MgSO4), filtered, and concentrated under reduced pressure to give a dark-brown oil. The oil was suspended in boiling petroleum ether and the hot solution filtered to remove a small amount of brown solid. The filtrate was then cooled and filtered to obtain a light-gray solid. The filtrate was concentrated under reduced pressure to give a light-brown solid which was combined with the gray solid obtained from recrystallization to afford the title compound of Step F (1.28 g, 50%). 1 H NMR (CDCl3): delta4.92 (s,2H), 7.15 (m,2H), 7.5 (d, 1H). 19 F NMR (CDCl3): delta-50.33 (s,2F).
Reference： [1]Patent: US5633218,1997,A
  • 2
  • [ 1583-59-1 ]
  • [ 121-43-7 ]
  • [ 126120-87-4 ]
YieldReaction ConditionsOperation in experiment
Intermediate 195(2,2-difluoro-l,3-benzodioxol-4-yl)boronic acid2,2-Difluoro-l,3-benzodioxole (960 mg, 6.1 mmol) was dissolved in THF (8 mL) and cyclohexane (4 mL) and the resulting solution cooled to -78 C. sec-BuLi 1.4M solution in cyclohexane (4.3 mL, 6.1 mmol) was added dropwise and the reaction mixture stirred for 1.5 hours at -78C. Trimethylborate (694 mg, 6.75 mmol) was added and the mixture was allowed to warm slowly to -30 C. The reaction mixture was quenched with a 2N solution of HCI and diluted with ethyl acetate. Two phases were separated and the organic layer was washed twice with brine, dried over Na2S04 and evaporated to dryness affording the title compound as yellow oil which was used in the next step without further purification. 1H-NMR (400 MHz, DMSO-d6 + D20): delta ppm 7.39 (1H, dd), 7.34 (1H, dd), 7.14 (t, 1H, 7=7.90 Hz). 19F-NMR (376 MHz, DMSO-d6 + D20): delta ppm -48.92. 13C-NMR (200 MHz, DMSO-d6 + D20): delta ppm 147.3, 142.8, 131.6 (t, 7=250.7 Hz), 130.1, 124.3, 112.0
2,2-Difluoro-l,3-benzodioxole (960 mg, 6.1 mmol) was dissolved in THF (8 mL) and cyclohexane (4 mL) and the resulting solution cooled to -78 C. sec-BuLi 1.4M solution in cyclohexane (4.3 mL, 6.1 mmol) was added dropwise and the reaction mixture stirred for 1.5 hours at -78C. Trimethylborate (694 mg, 6.75 mmol) was added and the mixture was allowed to warm slowly to -30 C. The reaction mixture was quenched with a 2N solution of HCI and diluted with ethyl acetate. Two phases were separated and the organic layer was washed twice with brine, dried over Na2S04 and evaporated to dryness affording the title compound as yellow oil which was used in the next step without further purification. 1H-NM (400 M Hz, DMSO-d6 + D20): delta ppm 7.39 (1H, dd), 7.34 (1H, dd), 7.14 (t, 1H,7=7.90 Hz). 19F-NMR (376 MHz, DMSO-d6 + D20): delta ppm -48.92. 13C-NMR (200 M Hz, DMSO-d6 + D20): delta ppm 147.3, 142.8, 131.6 (t, 7=250.7 Hz), 130.1, 124.3, 112.0
2,2-Difluoro-1,3-benzodioxole (960 mg, 6.1 mmol) was dissolved in THF (8 mL) and cyclohexane (4 mL) and the resulting solution cooled to -78 C. sec-BuLi 1.4M solution in cyclohexane (4.3 mL, 6.1 mmol) was added dropwise and the reaction mixture stirred for 1.5 hours at -78 C. Trimethylborate (694 mg, 6.75 mmol) was added and the mixture was allowed to warm slowly to -30 C. The reaction mixture was quenched with a 2N solution of HCl and diluted with ethyl acetate. Two phases were separated and the organic layer was washed twice with brine, dried over Na2SO4 and evaporated to dryness affording the title compound as yellow oil which was used in the next step without further purification. 1H-NMR (400 MHz, DMSO-d6+D2O): delta ppm 7.39 (1H, dd), 7.34 (1H, dd), 7.14 (t, 1H, J=7.90 Hz). 19F-NMR (376 MHz, DMSO-d6+D2O): delta ppm -48.92. 13C-NMR (200 MHz, DMSO-d6+D2O): delta ppm 147.3, 142.8, 131.6 (t, J=250.7 Hz), 130.1, 124.3, 112.0
Reference： [1]Patent: WO2012/76877,2012,A1 .Location in patent: Page/Page column 167-168
[2]Patent: WO2013/83994,2013,A1 .Location in patent: Page/Page column 44-45
[3]Patent: US2014/323508,2014,A1 .Location in patent: Paragraph 0304; 0305; 0306
  • 3
  • [ 1583-59-1 ]
  • [ 126120-87-4 ]
YieldReaction ConditionsOperation in experiment
Intermediate 195 (2,2-difluoro-1,3-benzodioxol-4-yl)boronic acid [1074] [1075] 2,2-Difluoro-1,3-benzodioxole (960 mg, 6.1 mmol) was dissolved in THF (8 mL) and cyclohexane (4 mL) and the resulting solution cooled to -78 C. sec-BuLi 1.4M solution in cyclohexane (4.3 mL, 6.1 mmol) was added dropwise and the reaction mixture stirred for 1.5 hours at -78 C. Trimethylborate (694 mg, 6.75 mmol) was added and the mixture was allowed to warm slowly to -30 C. The reaction mixture was quenched with a 2N solution of HCl and diluted with ethyl acetate. Two phases were separated and the organic layer was washed twice with brine, dried over Na2SO4 and evaporated to dryness affording the title compound as yellow oil which was used in the next step without further purification. [1076] 1H NMR (400 MHz, DMSO-d6+D2O): delta ppm 7.39 (1H, dd), 7.34 (1H, dd), 7.14 (t, 1H, J=7.90 Hz). 19F-NMR (376 MHz, DMSO-d6+D2O): delta ppm -48.92. 13C-NMR (200 MHz, DMSO-d6+D2O): delta ppm 147.3, 142.8, 131.6 (t, J=250.7 Hz), 130.1, 124.3, 112.0
Reference： [1]Patent: US2013/267510,2013,A1 .Location in patent: Paragraph 1074-1076
  • 4
  • [ 1583-59-1 ]
  • [ 121-43-7 ]
  • [ 7732-18-5 ]
  • [ 126120-87-4 ]
YieldReaction ConditionsOperation in experiment
84.82% 2,2-Difluoro-1 ,3-benzodioxole (3 g, 18.98 mmol) was dissolved in TBF(60 mL) and the resulting solution cooled to -78 oc. Sec-butyllithium (1.3M, 15 mL) wasadded dropwise and the reaction mixture stirred for 1.5 h at -78 oc. Trimethyl borate (2.44mL, 21.63 mmol) was added and the mixture was allowed to warm slowly to -30 oc for lh.The reaction mixture was quenched with 2N solution of HCl, adjusted to pH .~ 2-3 anddiluted with H20 (30 mL). The reaction was extracted with EA (200 mL), two phases wereseparated and the organic layer was washed with brine (1 00 mL), dried over Na2S04, filteredand evaporated to dryness. Compound 107A (3.25 g, yield 84.82(%) was obtained as a whitesolid, which was used for next step without purification. 1H NMR (400 MHz, DMSO-d6) 88.44 (br s, 2B), 7.42 (del, J "' 7.8, 15.3 Hz, 2H), 7.23-7.12 (m, lEI).
Reference： [1]Patent: WO2019/190885,2019,A1 .Location in patent: Paragraph 0421

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• Alkyl Halide Occurrence • Halogenation • Heat of Combustion • Reactions of Amines
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