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[ CAS No. 13675-18-8 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 13675-18-8
Chemical Structure| 13675-18-8
Structure of 13675-18-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 13675-18-8 ]

CAS No. :13675-18-8 MDL No. :MFCD05663888
Formula : B2H4O4 Boiling Point : -
Linear Structure Formula :- InChI Key :SKOWZLGOFVSKLB-UHFFFAOYSA-N
M.W : 89.65 Pubchem ID :10986154
Synonyms :
Hypodiboric acid

Calculated chemistry of [ 13675-18-8 ]

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 0
Fraction Csp3 : None
Num. rotatable bonds : 1
Num. H-bond acceptors : None
Num. H-bond donors : None
Molar Refractivity : 20.38
TPSA : 80.92 Ų

Pharmacokinetics

GI absorption : None
BBB permeant : None
P-gp substrate : None
CYP1A2 inhibitor : None
CYP2C19 inhibitor : None
CYP2C9 inhibitor : None
CYP2D6 inhibitor : None
CYP3A4 inhibitor : None
Log Kp (skin permeation) : None cm/s

Lipophilicity

Log Po/w (iLOGP) : None
Log Po/w (XLOGP3) : None
Log Po/w (WLOGP) : None
Log Po/w (MLOGP) : None
Log Po/w (SILICOS-IT) : None
Consensus Log Po/w : None

Druglikeness

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

Water Solubility

Log S (ESOL) : None
Solubility : None mg/ml ; None mol/l
Class : None
Log S (Ali) : None
Solubility : None mg/ml ; None mol/l
Class : None
Log S (SILICOS-IT) : None
Solubility : None mg/ml ; None mol/l
Class : None

Medicinal Chemistry

PAINS : None alert
Brenk : None alert
Leadlikeness : None
Synthetic accessibility : None

Safety of [ 13675-18-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 13675-18-8 ]

* 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 [ 13675-18-8 ]
  • Downstream synthetic route of [ 13675-18-8 ]

[ 13675-18-8 ] Synthesis Path-Upstream   1~104

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Reference: [1] Organic Process Research and Development, 2017, vol. 21, # 11, p. 1859 - 1863
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Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
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Reference: [1] Chemical Science, 2016, vol. 7, # 6, p. 3676 - 3680
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Reference: [1] Organic Process Research and Development, 2017, vol. 21, # 11, p. 1859 - 1863
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Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
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Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1842 - 1851
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Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
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Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
[2] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
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Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1842 - 1851
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Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1842 - 1851
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Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
[2] Organic Process Research and Development, 2017, vol. 21, # 11, p. 1859 - 1863
[3] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1842 - 1851
  • 18
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Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
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Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
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Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1842 - 1851
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Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1842 - 1851
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Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1842 - 1851
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Reference: [1] Organic Process Research and Development, 2017, vol. 21, # 11, p. 1859 - 1863
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
[2] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
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Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
[2] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
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Reference: [1] Organic Process Research and Development, 2017, vol. 21, # 11, p. 1859 - 1863
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Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1842 - 1851
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Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
[2] Organic Process Research and Development, 2017, vol. 21, # 11, p. 1859 - 1863
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
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Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
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Reference: [1] Chemical Science, 2016, vol. 7, # 6, p. 3676 - 3680
[2] Organic Process Research and Development, 2017, vol. 21, # 11, p. 1859 - 1863
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Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
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Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
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Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
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Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
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Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
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Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
[2] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
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Reference: [1] Organic Process Research and Development, 2017, vol. 21, # 11, p. 1859 - 1863
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Reference: [1] Organic Process Research and Development, 2017, vol. 21, # 11, p. 1859 - 1863
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Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 34, p. 10999 - 11003[2] Angew. Chem., 2018, # 130, p. 11165 - 11169,5
[3] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
[4] Organic Process Research and Development, 2017, vol. 21, # 11, p. 1859 - 1863
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Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 34, p. 10999 - 11003[2] Angew. Chem., 2018, # 130, p. 11165 - 11169,5
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Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
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Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
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Reference: [1] Organic Process Research and Development, 2017, vol. 21, # 11, p. 1859 - 1863
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
[2] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
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Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1842 - 1851
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Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1842 - 1851
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
[2] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
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Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
[2] Organic Process Research and Development, 2017, vol. 21, # 11, p. 1859 - 1863
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
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Reference: [1] Chemical Science, 2016, vol. 7, # 6, p. 3676 - 3680
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
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Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
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Reference: [1] Organic Letters, 2016, vol. 18, # 20, p. 5248 - 5251
[2] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1842 - 1851
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
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Reference: [1] Organic Process Research and Development, 2017, vol. 21, # 11, p. 1859 - 1863
[2] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1842 - 1851
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
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Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1842 - 1851
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YieldReaction ConditionsOperation in experiment
42% With chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II); potassium acetate; XPhos In ethanol at 80℃; for 0.75 h; Inert atmosphere General procedure: A glass vial equipped with a magnetic stir bar and fitted with a Teflon screw cap was charged with BBA (90 mg, 1.0 mmol), KOAc (98 mg, 1.0 mmol) and the aryl halide (0.50 mmol). To this vessel was added EtOH (2.5 mL) and the reaction media was degassed with Argon for 5 minutes. XPhos Pd G2 (79 mg, 10 molpercent) was then added, and the solution was stirred (750 rpm) and heated at 80°C until full conversion was observed. The reaction media was filtered over celite and the crude filtrate was purified using Teledyne Isco Combiflash device (silica gel column chromatography 15 μm) and Hept:DCM (90:10 to 0:100) as solvent.
Reference: [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 14, p. 2757 - 2761
[2] Tetrahedron Letters, 2017, vol. 58, # 39, p. 3757 - 3759
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Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
[2] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
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Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 46, p. 6230 - 6235,6
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Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
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Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
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Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 28, p. 11667 - 11673
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Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
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  • [ 877399-74-1 ]
YieldReaction ConditionsOperation in experiment
10.1 g
Stage #1: With boron trifluoride diethyl etherate In tolueneReflux; Inert atmosphere
Stage #2: With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); N-ethyl-N,N-diisopropylamine; triphenylphosphine In ethanol at 80℃; for 4 h; Inert atmosphere
Stage #3: Inert atmosphere
In a 250 ml reaction flask equipped with a magnetic stir and refluxing device, followed by the addition of N-Boc-4-piperidine hydrazine crude, 5.2 grams of 2-chloro-malondialdehyde, 0.4 g of boron trifluoride diethyl ether and 100 ml of toluene, heated to reflux dehydration condensation, detection reaction is no longer done. under nitrogen protection, after the reaction solution is cooled, the solvent is dried. Add 50 ml of absolute ethanol, 6.0 g tetrahydroxy diboron, 17.1 g of diisopropylethylamine, 0.24 g of NiCl2 (dppp) and 0.23 g of PPh3 were added and, after stirring, 80 °C for 4 hours, After cooling the generated inorganic salt, the filtrate is evaporated to dryness, after adding 80 ml of ethyl acetate, washed, the organic layer was added with 7.2 grams of pinacol, after the reaction is complete, washed, organic layer of diatomite filter steaming, N-hexane / ethyl acetate (1:10), after filtration, 10.1 g of a white crystalline solid product was obtained, Yield 61percent, GC: 98.5percent, HNMR (400 MHz, CDCl3): 7.79 (S, 1H), 7.73 (s, 1H), 4.28 (m, 3H), 2.88 (m, 2H), 2.10 (m, 2H), 1.88 (m, 2H), 1.47 (s, 9H) S, 12H).
Reference: [1] Patent: CN105153211, 2017, B, . Location in patent: Paragraph 0020; 0023-0024
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YieldReaction ConditionsOperation in experiment
8.8 g
Stage #1: With boron trifluoride diethyl etherate In tolueneReflux; Inert atmosphere
Stage #2: With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); N-ethyl-N,N-diisopropylamine; triphenylphosphine In ethanol at 20℃; for 12 h; Inert atmosphere
Stage #3: Inert atmosphere
In a 250 ml reaction flask equipped with a magnetic stir and refluxing device, followed by the addition of N-Boc-4-piperidine hydrazine crude, 6.4 grams of 2-bromomalondialdehyde, 0.5 g of boron trifluoride diethyl ether with 120 ml of toluene, heated to reflux dehydration condensation, detection reaction is no longer done. under nitrogen protection, after the reaction solution is cooled, the solvent is dried. Add 50 ml of absolute ethanol, 5.8 g of tetrahydroxy diboron, 16.5 g of diisopropylethylamine, 0.23 g of NiCl2 (dppp) and 0.22 g of PPh3 were added and, after stirring, room temperature reaction for 12 hours, Filter out the resulting inorganic salt, The filtrate is evaporated to dryness, After adding 80 ml of ethyl acetate, washed, the organic layer was added with 6.0 grams of pinacol, after the reaction is complete, washed, organic layer of diatomite filter steaming, N-hexane / acetone (1: 9) and filtered to give 8.8 g of a white solid product in 55percent yield, GC: 98.2percent, HNMR (400 MHz, CDCl3): 7.80 (s, 1H), 7.72 (s, 4.28 (m, 3H), 2.87 (m, 2H), 2.10 (m, 2H), 1.88 (m, 2H), 1.46 (s, 9H), 1.32 (s, 12H).
Reference: [1] Patent: CN105153211, 2017, B, . Location in patent: Paragraph 0015; 0018-0019
  • 85
  • [ 7732-18-5 ]
  • [ 158752-98-8 ]
  • [ 13675-18-8 ]
YieldReaction ConditionsOperation in experiment
8.5 g at 100℃; Inert atmosphere Under nitrogen protection, tetrakis (tetrahydropyrrole) boron (0.1) was added to a three-necked flask equipped with a dropping and refluxing unitMole) and 50-60 times deionized water, and the temperature was raised to 100 ° C. After refluxing for 1.5 hours, the mixture was replaced by an atmospheric distillation unit,The reaction process to generate tetrahydropyrrole distillation, no longer with tetrahydropyrrole distilled, the reaction solution is cooled to room temperature, at this time a solid precipitation,Filtered and dried to give 8.5 g of whitesolidTetrahydroxy boron, HNMR purity of more than 98percent, consistent with the literature.Add 45 ml of methanol, stir at room temperature until completely dissolved (about 10-15 minutes), then add KHF2 aqueous solution (0.38 mol), stirring at room temperature for 1 hour, the system after standing and layered, carefully separated from the lower, Distilled to dry. After addition of acetone, the mixture was filtered to give 15.8 g of potassium boron trifluoride as a white solid, the total yield was 74percent
Reference: [1] Patent: CN104945426, 2017, B, . Location in patent: Paragraph 0026; 0027; 0028
  • 86
  • [ 1630-79-1 ]
  • [ 13675-18-8 ]
  • [ 506-59-2 ]
Reference: [1] Journal of the American Chemical Society, 1961, vol. 83, p. 4750 - 4754
[2] , Gmelin Handbook: B: B-Verb.4, 9.1, page 268 - 279,
  • 87
  • [ 7732-18-5 ]
  • [ 13701-67-2 ]
  • [ 13675-18-8 ]
  • [ 11113-50-1 ]
Reference: [1] New Journal of Chemistry, 2003, vol. 27, # 5, p. 773 - 775
  • 88
  • [ 7318-94-7 ]
  • [ 13675-18-8 ]
  • [ 11113-50-1 ]
Reference: [1] Ber., 1937, vol. 70, p. 1393 - 1402
[2] Ber., 1937, vol. 70, p. 1393 - 1402
[3] , Gmelin Handbook: B: SVol.1, 4.2.3, page 136 - 144,
[4] , Gmelin Handbook: B: SVol.1, 4.2.3, page 136 - 144,
  • 89
  • [ 1630-79-1 ]
  • [ 7732-18-5 ]
  • [ 13675-18-8 ]
  • [ 124-40-3 ]
Reference: [1] Journal of the American Chemical Society, 1961, vol. 83, p. 4750 - 4754
[2] Journal of the American Chemical Society, 1961, vol. 83, p. 1766 - 1767
[3] , Gmelin Handbook: B: B-Verb.7, 3.2.1, page 19 - 19,
[4] Chemische Berichte, 1961, vol. 94, p. 509 - 514
  • 90
  • [ 13701-67-2 ]
  • [ 13675-18-8 ]
Reference: [1] Ber., 1937, vol. 70, p. 1393 - 1402
[2] , Gmelin Handbook: B: SVol.1, 4.2.3, page 136 - 144,
  • 91
  • [ 7732-18-5 ]
  • [ 13701-67-2 ]
  • [ 7647-01-0 ]
  • [ 13675-18-8 ]
Reference: [1] Journal of the American Chemical Society, 1958, vol. 80, p. 6155 - 6158
[2] , Gmelin Handbook: B: B-Verb.7, 3.2.1, page 19 - 19,
  • 92
  • [ 67183-19-1 ]
  • [ 7732-18-5 ]
  • [ 13675-18-8 ]
  • [ 11113-50-1 ]
Reference: [1] New Journal of Chemistry, 2003, vol. 27, # 5, p. 773 - 775
  • 93
  • [ 64541-76-0 ]
  • [ 13675-18-8 ]
Reference: [1] Zeitschrift fuer Naturforschung, 1962, vol. 17b, p. 714 - 718
[2] , Gmelin Handbook: B: B-Verb.4, 9.1, page 268 - 279,
  • 94
  • [ 7360-75-0 ]
  • [ 13675-18-8 ]
Reference: [1] Zeitschrift fuer Naturforschung, 1962, vol. 17b, p. 714 - 718
[2] , Gmelin Handbook: B: B-Verb.4, 9.1, page 268 - 279,
  • 95
  • [ 1630-79-1 ]
  • [ 13675-18-8 ]
  • [ 124-40-3 ]
Reference: [1] Chemische Berichte, 1961, vol. 94, p. 509 - 514
[2] , Gmelin Handbook: B: B-Verb.4, 9.1, page 268 - 279,
  • 96
  • [ 7318-94-7 ]
  • [ 13675-18-8 ]
Reference: [1] Ber., 1937, vol. 70, p. 1393 - 1402
[2] , Gmelin Handbook: B: SVol.1, 4.8.5, page 226 - 230,
  • 97
  • [ 7318-94-7 ]
  • [ 7732-18-5 ]
  • [ 67-56-1 ]
  • [ 13675-18-8 ]
Reference: [1] , Gmelin Handbook: B: B-Verb.7, 3.2.1, page 19 - 19,
[2] Chemische Berichte, 1961, vol. 94, p. 509 - 514
  • 98
  • [ 13675-18-8 ]
  • [ 2924-09-6 ]
  • [ 873566-75-7 ]
YieldReaction ConditionsOperation in experiment
62.5% With N-ethyl-N,N-diisopropylamine; triphenylphosphine; nickel dichloride In ethanol at 65℃; for 6 h; Inert atmosphere 98percent of 2-fluoro-5-bromonitrobenzene (211 g, 0.96 mol) and iron powder (212 g, 3.8 mol) were mixed, 1200 ml of ethanol was added and glacial acetic acid (456 g, 7.6 mol) was added dropwise at room temperature. The reaction solution was treated with an oil bath at 60 ° CThe reaction solution was completed by a gas phase controlled reaction. The reaction solution was filtered through a Buchner funnel pad and the filtrate was evaporated to dryness and extracted with ethyl acetateN-heptane (volume ratio 1: 4) was purified by column and evaporated to give pure product 122.5 g, 98percent GC, yield 62.5percent
Reference: [1] Patent: CN104530107, 2016, B, . Location in patent: Paragraph 0031
  • 99
  • [ 13675-18-8 ]
  • [ 1040745-70-7 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 10, p. 2770 - 2773
  • 100
  • [ 13675-18-8 ]
  • [ 22876-17-1 ]
  • [ 1016644-38-4 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
  • 101
  • [ 13675-18-8 ]
  • [ 345965-52-8 ]
  • [ 1159489-46-9 ]
Reference: [1] Organic Process Research and Development, 2017, vol. 21, # 11, p. 1859 - 1863
  • 102
  • [ 76-09-5 ]
  • [ 13675-18-8 ]
  • [ 1048970-17-7 ]
Reference: [1] Patent: WO2018/189157, 2018, A1, . Location in patent: Page/Page column 6-7
  • 103
  • [ 76-09-5 ]
  • [ 13675-18-8 ]
  • [ 13826-27-2 ]
  • [ 1048970-17-7 ]
Reference: [1] Patent: WO2018/189157, 2018, A1, . Location in patent: Page/Page column 6
  • 104
  • [ 13675-18-8 ]
  • [ 202865-66-5 ]
  • [ 1061223-45-7 ]
YieldReaction ConditionsOperation in experiment
62% With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); N-ethyl-N,N-diisopropylamine; triphenylphosphine In ethanol for 4 h; Inert atmosphere; Reflux To a solution of (2-bromo-5-fluorophenyl) methanol (10.05 g, 0.049 mol) in Ethanol 100 mL), NiCI2(dppp) (2.67 g, 0.0049 mol), (HO)2B-B(OH)2 (6.62g, 0.074 mol), PPh3 (0.01 mol), (DIPEA (25.7 mL, 0.148 mol) are added. The resulting mixture is degassed using a stream of nitrogen. The reaction mixture is stirred at reflux for 4 hrs, then cooled to room temperature, diluted with H20 and extracted with EtOAc. The organic layer is dried over Na2S04 and evaporated in vacuo to yield (4-fluoro-2-(hydroxymethyl)phenyl)boronic acid (6) that is used in the next reaction step without further purification (Yield: 62percent).
Reference: [1] Patent: WO2017/183043, 2017, A1, . Location in patent: Page/Page column 33
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