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[ CAS No. 23112-96-1 ] {[proInfo.proName]}

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Chemical Structure| 23112-96-1
Chemical Structure| 23112-96-1
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Product Details of [ 23112-96-1 ]

CAS No. :23112-96-1 MDL No. :MFCD01318987
Formula : C8H11BO4 Boiling Point : -
Linear Structure Formula :- InChI Key :BKWVXPCYDRURMK-UHFFFAOYSA-N
M.W : 181.98 Pubchem ID :2734343
Synonyms :

Calculated chemistry of [ 23112-96-1 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 49.25
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) : -6.86 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.77
Log Po/w (WLOGP) : -0.62
Log Po/w (MLOGP) : -0.25
Log Po/w (SILICOS-IT) : -0.74
Consensus Log Po/w : -0.17

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.6
Solubility : 4.6 mg/ml ; 0.0253 mol/l
Class : Very soluble
Log S (Ali) : -1.59
Solubility : 4.7 mg/ml ; 0.0258 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.54
Solubility : 5.21 mg/ml ; 0.0286 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.05

Safety of [ 23112-96-1 ]

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

Application In Synthesis of [ 23112-96-1 ]

* 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 [ 23112-96-1 ]
  • Downstream synthetic route of [ 23112-96-1 ]

[ 23112-96-1 ] Synthesis Path-Upstream   1~15

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Reference: [1] Synlett, 1998, # 2, p. 141 - 142
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Reference: [1] Chinese Journal of Chemistry, 2013, vol. 31, # 1, p. 27 - 30
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YieldReaction ConditionsOperation in experiment
96% With sodium hydroxide; hydroxylamine-O-sulfonic acid In water; acetonitrile for 1 h; Sonication General procedure: Reactions facilitated by sonication were performed on a 1.0 mmol scale. Arylboronic acid 3 (1.0 equiv) and MeCN (5.0 mL) were added to a 25 mL microwave vial equipped with a stir bar, followed by HSA (1.5 equiv) and aq 1 M NaOH (5 equiv). The mixture was capped and set to stir for 5 min, then placed in an ultrasonic cleaner for 30 min (35 kHz, 90 W), at which time the vial was removed and a small aliquot was taken for reaction monitoring via HPLC analysis. The mixture was then placed back in the sonication bath for 30 min. This process was repeated until the reaction had gone to completion, or the reaction failed to progress, as monitored by HPLC. The reaction mixture was diluted with H2O (30 mL) and extracted with EtOAc (2 × 30mL). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes) to afford the desired amine product 2.
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 5, p. 2545 - 2553
[2] Synthesis (Germany), 2017, vol. 49, # 11, p. 2555 - 2561
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Reference: [1] Chemical Communications, 2018, vol. 54, # 57, p. 7904 - 7907
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YieldReaction ConditionsOperation in experiment
90%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -40 - 30℃; for 1 h; Inert atmosphere
Stage #2: at -40 - -30℃; for 1 h;
Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water at 20 - 30℃; for 1 h;
41.5g (0.3mol) 1,3-dimethoxybenzene, 170gTHF are placed into a dry 1L three-necked flask. Under nitrogen protection, stirwhile cooling the system temperature to -30 ~ -40 deg.C. Add dropwise 240ml (0.6mol) n-butyllithium n-hexane solution. Dropping complete. Heat to 10 ~ 30 deg.C and maintain temperature for 1h. After maintaining the temperature, cool the system temperature to -30 ~ -40 deg.C. Add dropwise 62.4g (0.6mol)of trimethyl borate. Dropping complete. Maintain temperature for 1h. Maintain temperature was complete. Add 148g concentrated hydrochloric acid and 150g water. Reaction solution was stirred at 20 ~ 30 deg,C and maintain temperature 1h. Maintain temperature was completed, the reaction solution under reduced pressure until solvent-free solvent removal, the product was added to 200g of water, stirred for 20min, suction filtration using a Buchner funnel to give 45g of white solid, a yield of 90.0percent, measured by gas chromatographic purity of 99.0percent .
70%
Stage #1: With n-butyllithium In tetrahydrofuran at 0℃; for 4 h; Inert atmosphere
Stage #2: at -78 - 20℃; for 12 h; Inert atmosphere
It fills with nitrogen to a dried 5L reactor.1,3-dimethoxybenzene 200.0g (1.45 mol), put into a 2000ml tetrahydrofuran and lower to 0 .1.6M n-butyl lithium 1085ml (1.74 mol) of After slowly dropped trim and stirred for 4 hours at 0 °C. After raising to -78 °C After the temperature was reduced to trimethyl borate was added dropwise 225.6g (2.17 mol) slowly at room temperature and stirred 12 hours.After the reaction was completed, the mixture was stirred for 30 minutes at room temperature was added dropwise a 2M hydrochloric acid solution 1000ml. After extraction with ethyl acetate and water and the organic layer was concentrated under reduced pressure and recrystallized from ethyl acetate and hexane to obtain 184 g of a compound represented by Formula 1-a]. (70percent yield)
69%
Stage #1: With n-butyllithium In tetrahydrofuran at -10℃; for 4 h; Inert atmosphere
Stage #2: at -78 - 20℃;
Stage #3: With hydrogenchloride In waterInert atmosphere
Intermediate 1-b was synthesized as illustrated in the following Reaction Scheme 2: In a well-dried 2-L round-bottom flask reactor, 1,3-dimethoxy benzene (100.0 g, 0.724 mol) was dissolved in tetrahydrofuran (800 ml). The solution was chilled to −10° C. in a nitrogen atmosphere and then added slowly with drops of n-butyl lithium (543 ml, 0.868 mol). After 4 hrs of stirring at the same temperature, the temperature was decreased to −78° C. While this temperature was maintained, drops of trimethyl borate (112.8 g, 1.086 mol) were slowly added over 30 min, followed by stirring overnight at room temperature. After completion of the reaction, 2 N HCl was dropwise added for acidification. Extraction was made with water and ethyl acetate, and the organic layer thus formed was dried over magnesium sulfate. Subsequent to vacuum concentration, crystallization was conducted in heptane. The solid thus formed was filtered and washed with heptane to afford . 92.0 g, 69percent)
19 g
Stage #1: With n-butyllithium In tetrahydrofuran at -50℃; for 0.5 h; Inert atmosphere
Stage #2: With 1,4,7,10-tetramethyl-1,4, 7,10-tetraazacyclododecane In tetrahydrofuran at -50 - 20℃; for 4 h;
Stage #3: With hydrogenchloride In tetrahydrofuran; water for 1 h;
Under a nitrogen atmosphere, 250 g of anhydrous tetrahydrofuran was added to the reaction flask, stirring was continued, 19 g of 1,3-dimethoxybenzene was added and cooled to -50 ° C.N-BuLi was slowly added dropwise to 80 mL of 2.0 M, and after stirring for 30 minutes, 14 g of 1,4,7,10-tetramethyl-1,4,7,10-tetraazacyclododecane was slowly added dropwise.After incubation for 2 hours, 30 mL of trimethyl borate was slowly added dropwise at -50 ° C, stirred for 1 hr, slowly rose to room temperature and stirred for 1 hour.And 200 g of concentrated hydrochloric acid was added thereto, followed by stirring for 1 hour to carry out a hydrolysis reaction.The layers were allowed to stand, and the organic layer was washed three times with water (3 x 50 g).The aqueous layers were combined and the aqueous layer was extracted once with 50 ml of petroleum ether. The combined organic layers were dried over 50 g of anhydrous sodium sulfate and filtered.The filtrate was concentrated to dryness to give 19 g of 2,6-dimethoxybenzeneboronic acid.

Reference: [1] Patent: WO2004/24738, 2004, A1, . Location in patent: Page/Page column 13-14
[2] Patent: CN105348240, 2016, A, . Location in patent: Paragraph 0059; 0060
[3] Organic and Biomolecular Chemistry, 2016, vol. 14, # 20, p. 4664 - 4668
[4] Organic Letters, 2012, vol. 14, # 16, p. 4250 - 4253
[5] Patent: KR2016/90242, 2016, A, . Location in patent: Paragraph 0162; 0163; 0164; 0165; 0166; 0167; 0168
[6] Patent: US2018/9776, 2018, A1, . Location in patent: Paragraph 0097-0098
[7] Bulletin de la Societe Chimique de France, 1973, p. 767 - 769
[8] Patent: CN102718785, 2016, B, . Location in patent: Paragraph 0044; 0045
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Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 8, p. 3238 - 3240
[2] Journal of the American Chemical Society, 2010, vol. 132, # 2, p. 777 - 790
[3] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 14, p. 4574 - 4581
[4] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 6, p. 2051 - 2066
[5] Tetrahedron, 2008, vol. 64, # 2, p. 328 - 338
[6] European Journal of Organic Chemistry, 2002, # 19, p. 3294 - 3303
[7] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 814 - 824
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YieldReaction ConditionsOperation in experiment
80%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 3 h; Inert atmosphere
Stage #2: at -78 - 20℃;
A mixture of 2-bromo-1,3-dimethoxybenzene 0.018mol was dissolved in 100ml, dry THF, was added 500ml three dried flask, N2Under the protection of -78 reaction 30min, was slowly added dropwise n-butyl lithium 0.027mol, after the completion of the dropping kept -78 reaction 3h, then slowly dropped triisopropyl borate 0.02mol, after the completion of the dropping reaction was held at - 78 reaction 2h, gradually warming to room temperature, the reaction overnight. after the reaction monitored by TLC, the reaction solution was slowly quenched with water, extracted and evaporated to dryness to give (2,6-dimethoxyphenyl) boronic acid (formula III'-1 shown) 0.0144mol, 80percent yield.
Reference: [1] Patent: CN106146267, 2016, A, . Location in patent: Paragraph 0147-0149
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YieldReaction ConditionsOperation in experiment
69%
Stage #1: With n-butyllithium In tetrahydrofuran at -10℃; for 4 h; Inert atmosphere
Stage #2: at -78 - 20℃;
1,3-dimethoxybenzene (100.0 g, 0.724 mol) was added to a dry 2 L round bottom flask reactor and 800 ml of tetrahydrofuran was added and melted.After cooling the reaction solution to -10 ° C under nitrogen atmosphere, n-butyllithium (543 ml, 0.868 mol) was slowly added dropwise.After stirring at the same temperature for 4 hours, the mixture was cooled to -78 ° C. The same temperature was maintained and trimethyl borate (112.8 g, 1.086 mol) was slowly added dropwise for 30 minutes, after which it was stirred overnight at room temperature.After completion of the reaction, 2N hydrochloric acid was slowly added dropwise and acidified. Water was extracted with magnesium sulfate after extraction and separation of the organic layer with water and ethyl acetate.The material was concentrated under reduced pressure and then crystallized using heptane. The resulting solid was filtered and washed with heptane to obtain intermediate 1-b (92.0 g, 69percent).
Reference: [1] Patent: CN107207454, 2017, A, . Location in patent: Paragraph 0441; 0447; 0448; 0450; 0451
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YieldReaction ConditionsOperation in experiment
20 g
Stage #1: With n-butyllithium In tetrahydrofuran at -30℃; for 0.5 h; Inert atmosphere
Stage #2: With N,N',N''-trimethyl-1,4,7-triazacyclononane In tetrahydrofuran at -30 - 20℃; for 4 h;
Stage #3: With hydrogenchloride In tetrahydrofuran; water for 1 h;
Under a nitrogen atmosphere, 250 g of anhydrous tetrahydrofuran was added to the reaction flask, stirring was continued, 19 g of 1,3-dimethoxybenzene was added and cooled to -50 ° C.N-BuLi was slowly added dropwise to 80 mL of 2.0 M, and after stirring for 30 minutes, 14 g of 1,4,7,10-tetramethyl-1,4,7,10-tetraazacyclododecane was slowly added dropwise.After incubation for 2 hours, 30 mL of trimethyl borate was slowly added dropwise at -50 ° C, stirred for 1 hr, slowly rose to room temperature and stirred for 1 hour.And 200 g of concentrated hydrochloric acid was added thereto, followed by stirring for 1 hour to carry out a hydrolysis reaction.The layers were allowed to stand, and the organic layer was washed three times with water (3 x 50 g).The aqueous layers were combined and the aqueous layer was extracted once with 50 ml of petroleum ether. The combined organic layers were dried over 50 g of anhydrous sodium sulfate and filtered.The filtrate was concentrated to dryness to give 19 g of 2,6-dimethoxybenzeneboronic acid.
Reference: [1] Patent: US6593480, 2003, B2,
[2] Patent: CN102718785, 2016, B, . Location in patent: Paragraph 0046; 0047
[3] Patent: US2001/41802, 2001, A1,
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Reference: [1] Patent: US6521666, 2003, B1,
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Reference: [1] Bioorganic and medicinal chemistry letters, 2002, vol. 12, # 17, p. 2415 - 2418
[2] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 3, p. 747 - 750
[3] European Journal of Organic Chemistry, 2002, # 19, p. 3294 - 3303
[4] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 814 - 824
[5] Organic Letters, 2014, vol. 16, # 17, p. 4662 - 4665
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Reference: [1] Organic Letters, 2014, vol. 16, # 17, p. 4662 - 4665
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  • [ 2785-97-9 ]
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Reference: [1] , Gmelin Handbook: B: B-Verb.13, 4.7.2.6, page 219 - 226,
[2] C. A., 1960, p. 8851
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Reference: [1] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 6, p. 2051 - 2066
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Reference: [1] European Journal of Organic Chemistry, 2012, # 11, p. 2127 - 2131
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