Home Cart 0 Sign in  

[ CAS No. 40138-16-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 40138-16-7
Chemical Structure| 40138-16-7
Structure of 40138-16-7 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 40138-16-7 ]

Related Doc. of [ 40138-16-7 ]

Alternatived Products of [ 40138-16-7 ]
Product Citations

Product Details of [ 40138-16-7 ]

CAS No. :40138-16-7 MDL No. :MFCD00151822
Formula : C7H7BO3 Boiling Point : -
Linear Structure Formula :- InChI Key :DGUWACLYDSWXRZ-UHFFFAOYSA-N
M.W : 149.94 Pubchem ID :292189
Synonyms :

Calculated chemistry of [ 40138-16-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 41.66
TPSA : 57.53 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) : -7.01 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.29
Log Po/w (WLOGP) : -0.82
Log Po/w (MLOGP) : -0.36
Log Po/w (SILICOS-IT) : -0.6
Consensus Log Po/w : -0.3

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.22
Solubility : 8.95 mg/ml ; 0.0597 mol/l
Class : Very soluble
Log S (Ali) : -1.06
Solubility : 13.1 mg/ml ; 0.087 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.22
Solubility : 9.08 mg/ml ; 0.0605 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.23

Safety of [ 40138-16-7 ]

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 [ 40138-16-7 ]

* 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 [ 40138-16-7 ]
  • Downstream synthetic route of [ 40138-16-7 ]

[ 40138-16-7 ] Synthesis Path-Upstream   1~24

  • 1
  • [ 626-55-1 ]
  • [ 40138-16-7 ]
  • [ 176690-44-1 ]
Reference: [1] Organic Letters, 2004, vol. 6, # 19, p. 3337 - 3340
[2] Journal of Organic Chemistry, 2017, vol. 82, # 1, p. 76 - 85
[3] Journal of the Chemical Society - Perkin Transactions 1, 1996, # 6, p. 515 - 518
[4] Patent: WO2005/811, 2005, A1, . Location in patent: Page/Page column 58; 123
  • 2
  • [ 626-60-8 ]
  • [ 40138-16-7 ]
  • [ 176690-44-1 ]
Reference: [1] European Journal of Organic Chemistry, 2012, # 31, p. 6248 - 6259,12
[2] European Journal of Organic Chemistry, 2012, # 31, p. 6248 - 6259
  • 3
  • [ 1003-09-4 ]
  • [ 40138-16-7 ]
  • [ 99902-07-5 ]
YieldReaction ConditionsOperation in experiment
92% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 80℃; for 5 h; Inert atmosphere In a 100-ml three-neck flask, 3.0 g (20 mmol) of compound a-1, 4.24 g (26 mmol) of compound a-2, 10.6 g(100.0 mmol) of sodium carbonate, 30 ml of toluene, 10 ml of ethanol, and 20 ml of water were placed, and in a nitrogen atmosphere, under stirring at room temperature, 693 mg of tetrakis (triphenylphosphine) palladium ( 0 ) was added thereto. The resulting mixture was heated to 80°C, and stirring was performed for 5 hours. After completion of the reaction, the organic layer was extracted with toluene and dried over anhydrous sodium sulfate, followed by purification by silica gel column chromatography (developing solvent:toluene/heptane mixture) to give 3.46 g (yield 92percent) of intermediate a-3 (white oil) .
Reference: [1] Patent: WO2011/132623, 2011, A1, . Location in patent: Page/Page column 28-29
[2] Journal of the Chemical Society - Perkin Transactions 1, 1996, # 6, p. 515 - 518
[3] Tetrahedron, 2008, vol. 64, # 38, p. 9033 - 9043
[4] Journal of Organic Chemistry, 2002, vol. 67, # 17, p. 6264 - 6267
  • 4
  • [ 96-43-5 ]
  • [ 40138-16-7 ]
  • [ 99902-07-5 ]
Reference: [1] European Journal of Organic Chemistry, 2012, # 31, p. 6248 - 6259,12
[2] European Journal of Organic Chemistry, 2012, # 31, p. 6248 - 6259
  • 5
  • [ 188290-36-0 ]
  • [ 40138-16-7 ]
  • [ 99902-07-5 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 2, p. 578 - 580
  • 6
  • [ 83813-73-4 ]
  • [ 40138-16-7 ]
  • [ 28272-96-0 ]
Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 9, p. 3404 - 3410
  • 7
  • [ 40138-16-7 ]
  • [ 26260-02-6 ]
YieldReaction ConditionsOperation in experiment
83% With perfluoroisopropyl iodide; copper; hydroquinone In N,N-dimethyl-formamide at 20℃; for 24 h; General procedure: (4-Nitrophenyl)boronic acid (0.067 g, 0.4 mmol), copper powder (0.0052 g, 0.08 mmol,), (CF3)2CFI (0.178 g, 0.6 mmol), and DMF (2 mL) were placed in a closed tube with a rubber stopper. The mixture was reacted at room temperature equipped with an air balloon for 24 h. The resulting suspension was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and concentrated to dryness. The crude product was purified by flash column chromatography on silica gel using petroleum ether/ethyl acetate = 20: 1 (v/v) as eluent to give 0.086 g of 2j as a light yellow solid (0.35 mmol, 87percent).
Reference: [1] Journal of Fluorine Chemistry, 2016, vol. 189, p. 59 - 67
  • 8
  • [ 380151-85-9 ]
  • [ 40138-16-7 ]
Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 46, p. 7899 - 7903
[2] Chemical Science, 2015, vol. 6, # 6, p. 3329 - 3333
  • 9
  • [ 1229227-01-3 ]
  • [ 68-12-2 ]
  • [ 40138-16-7 ]
YieldReaction ConditionsOperation in experiment
93.0 g
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -80 - 20℃; Inert atmosphere
Stage #2: With hydrogenchloride In tetrahydrofuran; hexane; water at 20℃;
Under nitrogen protection, the above-obtained o-bromobenzeneboronic acid trimer was added to anhydrous tetrahydrofuran (600 ml)After the addition, transfer to a 2 L three-necked flask and add dimethylformamide (87.7 g, 1.2 mol). Then cool the system to -70 ° C to -80 ° C, 520 ml (1.3 moles) of 2.5 M n-butyllithium hexane solution was slowly added dropwise, and the temperatureThe maximum temperature does not exceed -70 ° C, the addition is maintained at the temperature to continue stirring for 1-3 hours, then naturally rose to room temperatureMix 3-5 hours. TLC detection reaction is completed, the system cooled to 0 , adding 15percent hydrochloric acid aqueous solution quenching reaction, adjust the PHTo 1-2 to continue mixing at room temperature for 3-5 hours to ensure complete hydrolysis of the trimer. Distillation of the reaction solution, the organic solvent after distillation, solidAfter filtration, toluene was recrystallized to give 93.0 g of light gray solid o-aldehyde phenylboronic acid, HPLC: 99.0percentRate of 62percent.
Reference: [1] Patent: CN105037408, 2017, B, . Location in patent: Paragraph 0028; 0031; 0032
  • 10
  • [ 34824-58-3 ]
  • [ 121-43-7 ]
  • [ 40138-16-7 ]
Reference: [1] Journal of the American Chemical Society, 1997, vol. 119, # 33, p. 7817 - 7826
  • 11
  • [ 35364-86-4 ]
  • [ 40138-16-7 ]
Reference: [1] Patent: US2004/49050, 2004, A1,
  • 12
  • [ 112627-02-8 ]
  • [ 40138-16-7 ]
Reference: [1] Arkiv foer Kemi, 1957, vol. 10, p. 507,509
[2] Journal of the American Chemical Society, 1958, vol. 80, p. 835,836
  • 13
  • [ 6630-33-7 ]
  • [ 40138-16-7 ]
Reference: [1] European Journal of Organic Chemistry, 2013, # 12, p. 2316 - 2324
  • 14
  • [ 5419-55-6 ]
  • [ 6630-33-7 ]
  • [ 40138-16-7 ]
Reference: [1] Patent: CN104478723, 2016, B, . Location in patent: Paragraph 0021; 0022
  • 15
  • [ 932-31-0 ]
  • [ 40138-16-7 ]
Reference: [1] , Gmelin Handbook: B: B-Verb.13, 4.7.2.5, page 209 - 219,
  • 16
  • [ 7294-50-0 ]
  • [ 40138-16-7 ]
Reference: [1] , Gmelin Handbook: B: B-Verb.13, 4.7.2.5, page 209 - 219,
  • 17
  • [ 7732-18-5 ]
  • [ 40138-16-7 ]
Reference: [1] Arkiv foer Kemi, [2] Arkiv foer Kemi, 1957, vol. 10, p. 507 - 511
[3] , Gmelin Handbook: B: B-Verb.13, 4.7.2.5, page 209 - 219,
  • 18
  • [ 16419-60-6 ]
  • [ 40138-16-7 ]
Reference: [1] Arkiv foer Kemi, 1957, vol. 10, p. 507,509
  • 19
  • [ 40138-16-7 ]
  • [ 124-40-3 ]
  • [ 85107-53-5 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 20, p. 6492 - 6495
  • 20
  • [ 3034-53-5 ]
  • [ 40138-16-7 ]
  • [ 223575-69-7 ]
YieldReaction ConditionsOperation in experiment
38% With sodium carbonate In water; acetonitrile at 160℃; for 0.0833333 h; Microwave irradiation 6.21.
Synthesis of (S)-2-Amino-3-(4-{2-amino-6-[2,2,2-trifluoro-1-(2-thiazol-2-yl-phenyl)-ethoxy]-pyrimidin-4-yl}-phenyl)-propionic acid
To a 40 ml microwave reactor, was added 1.04 g of 2-formyl phenylboronic acid (6.9 mmoles), 1.14 g of 2-bromo thiazole (6.9 mmoles), 240 mg of palladium bistriphenyl-phosphine dichloride (Pd(PPh3)2Cl2, 0.34 mmoles).
Then, 13.8 ml of 1M Na2CO3 (13.8 mmoles) and 10 ml of CH3CN were added to the mixture.
The reactor was sealed, and the reaction was run under microwave at 160° C. for 5 minutes. LCMS shows completion of the reaction with desired product.
The reaction mixture was then poured into a separation funnel.
Then 200 ml of methylene chloride and 100 ml of water were added for extraction.
The methylene chloride layer was dried over MgSO4.
Removal of solvent gave a crude product, which was purified by silica gel column chromatography eluding with hexanes/ethyl acetate mixture (5/1 to 2/1) to give pure 2-thiazol-2-yl-benzaldehyde (0.5 g, yield: 38percent).
38% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In acetonitrile at 160℃; for 0.0833333 h; Sealed tube; Microwave irradiation To a 40 ml microwave reactor was added 1.04 g of 2-formylphenylboronic acid (6.9 mmol) of 1.14 g of 2-bromothiazole(6.9 mmol), 240 mg of bistriphenyl-phosphine palladium dichloride (Pd (PPh3) 2Cl2, 0.34 mmol). then,To the mixture was added 13.8 ml of 1 M Na2CO3 (13.8 mmol) and 10 ml of CH3CN. Sealed reactor,The reaction was run under microwave at 160 ° C for 5 minutes.LCMS shows the desired reaction of the desired product. The reaction mixture was then poured into a separation funnel. Add 200 ml of dichloromethaneAlkane and 100 ml of water for extraction. The dichloromethane layer was dried over MgSO4. The solvent was removed to give the crude product, which was passed through siliconThe column chromatography was eluted with a hexane / ethyl acetate mixture (5/1 to 2/1)To give pure 2-thiazol-2-yl-benzaldehyde (0.5 g, yield: 38percent).
Reference: [1] Patent: US2008/153852, 2008, A1, . Location in patent: Page/Page column 20
[2] Patent: CN104045626, 2017, B, . Location in patent: Paragraph 0240
[3] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 18, p. 8607 - 8618
[4] Patent: EP1392687, 2017, B1, . Location in patent: Paragraph 0133-0136
  • 21
  • [ 3034-53-5 ]
  • [ 40138-16-7 ]
  • [ 223575-69-7 ]
Reference: [1] Patent: US2009/29993, 2009, A1,
  • 22
  • [ 4595-59-9 ]
  • [ 40138-16-7 ]
  • [ 640769-71-7 ]
YieldReaction ConditionsOperation in experiment
220 mg With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 150℃; for 0.0833333 h; Sealed tube; Microwave irradiation The microwave vials (20 ml) were charged with 2-formylphenylboronic acid (290 mg, 2.0 mmol), 5-bromo-pyrimidine (316 mg,2.0 mmol) and 8 ml of acetonitrile. To the mixture was added 4 ml of an aqueous solution of sodium carbonate (1 M), followed by the addition of 100 mg of dichlorobis (triphenylYlphosphine) -palladium (II). The reaction vessel was sealed and heated at 150 & lt; 0 & gt; C for 5 minutes with microwave irradiation. After cooling the reaction mixtureExtracted with ethyl acetate. The organic layer was evaporated to provide a crude material which was purified by ISCO to give 220 mg of 2-pyrimidin-5-yl-benzaldehyde.
Reference: [1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 18, p. 8607 - 8618
[2] Patent: US2008/153852, 2008, A1, . Location in patent: Page/Page column 27
[3] Patent: CN104045626, 2017, B, . Location in patent: Paragraph 0318
  • 23
  • [ 4595-59-9 ]
  • [ 40138-16-7 ]
  • [ 497-19-8 ]
  • [ 640769-71-7 ]
Reference: [1] Patent: US2009/29993, 2009, A1,
  • 24
  • [ 40138-16-7 ]
  • [ 1402836-58-1 ]
Reference: [1] Patent: US2016/75711, 2016, A1,
[2] Tetrahedron, 2018, vol. 74, # 24, p. 3045 - 3051
[3] Tetrahedron, 2018, vol. 74, # 24, p. 3045 - 3051
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 40138-16-7 ]

Organoboron

Chemical Structure| 87199-17-5

[ 87199-17-5 ]

4-Formylphenylboronic acid

Similarity: 0.90

Chemical Structure| 308103-40-4

[ 308103-40-4 ]

(2-Acetylphenyl)boronic acid

Similarity: 0.89

Chemical Structure| 87199-16-4

[ 87199-16-4 ]

(3-Formylphenyl)boronic acid

Similarity: 0.88

Chemical Structure| 870777-33-6

[ 870777-33-6 ]

(3-Formyl-5-methylphenyl)boronic acid

Similarity: 0.88

Chemical Structure| 825644-26-6

[ 825644-26-6 ]

(4-Fluoro-2-formylphenyl)boronic acid

Similarity: 0.83

Aryls

Chemical Structure| 87199-17-5

[ 87199-17-5 ]

4-Formylphenylboronic acid

Similarity: 0.90

Chemical Structure| 308103-40-4

[ 308103-40-4 ]

(2-Acetylphenyl)boronic acid

Similarity: 0.89

Chemical Structure| 87199-16-4

[ 87199-16-4 ]

(3-Formylphenyl)boronic acid

Similarity: 0.88

Chemical Structure| 870777-33-6

[ 870777-33-6 ]

(3-Formyl-5-methylphenyl)boronic acid

Similarity: 0.88

Chemical Structure| 825644-26-6

[ 825644-26-6 ]

(4-Fluoro-2-formylphenyl)boronic acid

Similarity: 0.83

Aldehydes

Chemical Structure| 87199-17-5

[ 87199-17-5 ]

4-Formylphenylboronic acid

Similarity: 0.90

Chemical Structure| 87199-16-4

[ 87199-16-4 ]

(3-Formylphenyl)boronic acid

Similarity: 0.88

Chemical Structure| 870777-33-6

[ 870777-33-6 ]

(3-Formyl-5-methylphenyl)boronic acid

Similarity: 0.88

Chemical Structure| 825644-26-6

[ 825644-26-6 ]

(4-Fluoro-2-formylphenyl)boronic acid

Similarity: 0.83

Chemical Structure| 871126-15-7

[ 871126-15-7 ]

(3-Fluoro-2-formylphenyl)boronic acid

Similarity: 0.79