Home Cart 0 Sign in  
X

[ CAS No. 16932-45-9 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 16932-45-9
Chemical Structure| 16932-45-9
Chemical Structure| 16932-45-9
Structure of 16932-45-9 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 16932-45-9 ]

Related Doc. of [ 16932-45-9 ]

Alternatived Products of [ 16932-45-9 ]

Product Details of [ 16932-45-9 ]

CAS No. :16932-45-9 MDL No. :MFCD07780177
Formula : C8H9BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :VHVYSMMZHORFKU-UHFFFAOYSA-N
M.W : 217.06 Pubchem ID :612296
Synonyms :

Calculated chemistry of [ 16932-45-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.13
TPSA : 18.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.4
Log Po/w (XLOGP3) : 2.2
Log Po/w (WLOGP) : 2.47
Log Po/w (MLOGP) : 2.22
Log Po/w (SILICOS-IT) : 2.49
Consensus Log Po/w : 2.35

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.84
Solubility : 0.311 mg/ml ; 0.00143 mol/l
Class : Soluble
Log S (Ali) : -2.22
Solubility : 1.3 mg/ml ; 0.006 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.51
Solubility : 0.0668 mg/ml ; 0.000308 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.51

Safety of [ 16932-45-9 ]

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 [ 16932-45-9 ]

* 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 [ 16932-45-9 ]
  • Downstream synthetic route of [ 16932-45-9 ]

[ 16932-45-9 ] Synthesis Path-Upstream   1~29

  • 1
  • [ 151-10-0 ]
  • [ 17715-69-4 ]
  • [ 16932-45-9 ]
Reference: [1] Tetrahedron Letters, 1988, vol. 29, # 51, p. 6715 - 6718
[2] Tetrahedron Letters, 1988, vol. 29, # 51, p. 6715 - 6718
  • 2
  • [ 151-10-0 ]
  • [ 17715-69-4 ]
  • [ 16932-45-9 ]
  • [ 20469-65-2 ]
Reference: [1] Tetrahedron, 1982, vol. 38, # 8, p. 1105 - 1112
  • 3
  • [ 151-10-0 ]
  • [ 16932-45-9 ]
YieldReaction ConditionsOperation in experiment
52%
Stage #1: With n-butyllithium In diethyl ether; hexane for 4 h; Inert atmosphere
Stage #2: With bromine In diethyl ether; hexane at -50 - 20℃; for 2 h;
EXAMPLES Production Example (A) Synthesis of Intermediate (A) [Show Image] (A-1) Synthesis of 1-bromo-2,6-dimethoxybenzene In the atmosphere of argon, 19.3g of 1,3-dimethoxybenzene and 500 mL of anhydrous diethyl ether were placed in a flask. 105 mL (1.6M) of a hexane solution of n-butyllithium was added, and the resulting reaction solution was stirred with heating for 4 hours. After cooling to room temperature while stirring, the reaction solution was cooled to -50°C, followed by dropwise addition of 25g of bromine. Then, while heating the reaction solution to room temperature, stirring was conducted for 2 hours. Then, 300 mL of an aqueous 10percent sodium thiosulfate solution was added, and the resulting mixture was stirred for 1 hour. The reaction solution was extracted with ether, and an aqueous phase was removed, and then, an organic phase was washed with saturated saline. The organic phase was dried with magnesium sulfate and concentrated. Residues were purified by means of silica gel column chromatography. The resulting crystals were washed with hexane, whereby 17.9g (yield: 52percent) of white crystals of 1-bromo-2,6-dimethoxybenzene were obtained.
52%
Stage #1: With n-butyllithium In diethyl ether; hexane for 4 h; Heating; Inert atmosphere
Stage #2: With bromine In diethyl ether; hexane at -50 - 20℃; for 2 h;
Under an argon atmosphere 1,3-dimethoxy benzene (19.3g), was charged with anhydrous diethyl ether (500mL) to the flask, added 1.6M n-butyl lithium in hexane solution (105mL), the reaction solution was stirred for 4 hours under heating. After cooling to room temperature with continuous stirring, cooled to -50 ° C., was added dropwise bromine (25 g). The reaction solution was stirred for 2 hours while warming to room temperature. 10percent aqueous solution of sodium thiosulfate (300mL) added, and the mixture was stirred for 1 hour. The reaction solution was extracted with ether, after removing the aqueous layer, the organic layer was washed with saturated brine. The organic layer was dried over magnesium sulfate, concentrated, and the residue was purified by silica gel chromatography. The obtained crystals were washed with hexane to obtain Intermediate 14 (17.9g). The yield was 52percent.
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1995, # 6, p. 611 - 612
[2] Journal of Organic Chemistry, 2006, vol. 71, # 2, p. 775 - 788
[3] Patent: EP2436679, 2012, A1, . Location in patent: Page/Page column 46
[4] Patent: JP2015/7036, 2015, A, . Location in patent: Paragraph 0234; 0236
[5] Helvetica Chimica Acta, 1990, vol. 73, # 1, p. 48 - 62
[6] Tetrahedron, 1999, vol. 55, # 11, p. 3455 - 3466
[7] European Journal of Organic Chemistry, 2011, # 2, p. 341 - 354
[8] Patent: US2017/54086, 2017, A1, . Location in patent: Paragraph 0260
  • 4
  • [ 1466-76-8 ]
  • [ 16932-45-9 ]
YieldReaction ConditionsOperation in experiment
84% With silver carbonate; copper(ll) bromide; palladium dichloride In tetrahydrofuran at 110℃; for 24 h; General procedure: A mixture of carboxylic acid (1 equiv., 0.5 mmol), CuBr2 or CuCl2 (2 equiv., 1 mmol), Ag2CO3 (1 equiv., 0.5 mmol) and PdCl2 (0.1 equiv.) was heated inTHF (3 mL) under reflux at 110 oC for 24 h. After the reaction finished, the mixture was evaporated under vacuum and purified by columnchromatography to afford the desired product.
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 24, p. 3079 - 3081
[2] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 2794 - 2803
[3] Chemical Science, 2018, vol. 9, # 15, p. 3860 - 3865
  • 5
  • [ 558-13-4 ]
  • [ 151-10-0 ]
  • [ 16932-45-9 ]
YieldReaction ConditionsOperation in experiment
57% With n-butyllithium In diethyl ether; hexane; water REFERENCE EXAMPLE 3(1)
In a solution of 1,3-dimethoxybenzene (3.0 g, 21.7 mmol) dissolved in diethyl ether (90 ml), a 1.65M solution of n-butyl lithium in n-hexane (19.8 ml, 32.7 mmol of n-butyl lithium) was added at room temperature, and a reaction mixture was heated to reflux for 4 hours.
After cooling the reaction mixture to 0° C., a solution of carbon tetrabromide (15.8 g, 47.7 mmol) in diethyl ether (60 ml) was added to the mixture, and stirred at room temperature for 20 hours.
A small amount of water was added to the reaction mixture, and then the reaction mixture was diluted with ethyl acetate (90 ml).
The organic layer was washed with water and dried over anhydrous magnesium sulfate.
Thereafter, the solvent was evaporated off, and the residue was purified by column chromatography to obtain 1-bromo-2,6-dimethoxybenzene (2.70 g).
Yield, 57percent.
Elementary analysis: C8 H9 O2 Br Calculated: C, 44.23percent; H. 4.15percent Found: C, 44.02percent; H. 4.23percent.
Reference: [1] Patent: US5621129, 1997, A,
  • 6
  • [ 6751-75-3 ]
  • [ 74-88-4 ]
  • [ 16932-45-9 ]
Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 8, p. 2718 - 2721
  • 7
  • [ 142599-76-6 ]
  • [ 16932-45-9 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1992, vol. 65, # 5, p. 1389 - 1391
  • 8
  • [ 37895-73-1 ]
  • [ 151-10-0 ]
  • [ 1060691-55-5 ]
  • [ 16932-45-9 ]
Reference: [1] European Journal of Organic Chemistry, 2011, # 2, p. 341 - 354
  • 9
  • [ 24932-48-7 ]
  • [ 151-10-0 ]
  • [ 16932-45-9 ]
  • [ 1267964-42-0 ]
Reference: [1] European Journal of Organic Chemistry, 2011, # 2, p. 341 - 354
  • 10
  • [ 151-10-0 ]
  • [ 583-53-9 ]
  • [ 16932-45-9 ]
  • [ 755017-61-9 ]
Reference: [1] European Journal of Organic Chemistry, 2011, # 2, p. 341 - 354
  • 11
  • [ 851231-30-6 ]
  • [ 16932-45-9 ]
Reference: [1] Synthesis, 2005, # 4, p. 547 - 550
  • 12
  • [ 15540-84-8 ]
  • [ 151-10-0 ]
  • [ 16932-45-9 ]
  • [ 1267964-44-2 ]
Reference: [1] European Journal of Organic Chemistry, 2011, # 2, p. 341 - 354
  • 13
  • [ 142599-77-7 ]
  • [ 16932-45-9 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1992, vol. 65, # 5, p. 1389 - 1391
  • 14
  • [ 811711-33-8 ]
  • [ 151-10-0 ]
  • [ 16932-45-9 ]
  • [ 1267964-61-3 ]
Reference: [1] European Journal of Organic Chemistry, 2011, # 2, p. 341 - 354
  • 15
  • [ 104514-49-0 ]
  • [ 151-10-0 ]
  • [ 16932-45-9 ]
  • [ 1267964-61-3 ]
Reference: [1] European Journal of Organic Chemistry, 2011, # 2, p. 341 - 354
  • 16
  • [ 91-10-1 ]
  • [ 16932-45-9 ]
Reference: [1] Synthesis, 2005, # 4, p. 547 - 550
  • 17
  • [ 60319-07-5 ]
  • [ 16932-45-9 ]
Reference: [1] Synthesis, 2005, # 4, p. 547 - 550
  • 18
  • [ 92669-93-7 ]
  • [ 16932-45-9 ]
Reference: [1] Tetrahedron Letters, 1988, vol. 29, # 51, p. 6715 - 6718
  • 19
  • [ 1989-53-3 ]
  • [ 66832-24-4 ]
  • [ 16932-45-9 ]
Reference: [1] Tetrahedron, 1987, vol. 43, # 19, p. 4321 - 4328
  • 20
  • [ 634-36-6 ]
  • [ 16932-45-9 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 19, p. 5386 - 5390
  • 21
  • [ 151-10-0 ]
  • [ 17715-69-4 ]
  • [ 16932-45-9 ]
Reference: [1] Tetrahedron Letters, 1988, vol. 29, # 51, p. 6715 - 6718
[2] Tetrahedron Letters, 1988, vol. 29, # 51, p. 6715 - 6718
  • 22
  • [ 151-10-0 ]
  • [ 17715-69-4 ]
  • [ 16932-45-9 ]
  • [ 20469-65-2 ]
Reference: [1] Tetrahedron, 1982, vol. 38, # 8, p. 1105 - 1112
  • 23
  • [ 151-10-0 ]
  • [ 17715-69-4 ]
  • [ 16932-45-9 ]
  • [ 20469-65-2 ]
Reference: [1] Tetrahedron, 1982, vol. 38, # 8, p. 1105 - 1112
  • 24
  • [ 16932-45-9 ]
  • [ 6751-75-3 ]
Reference: [1] Tetrahedron, 2012, vol. 68, # 35, p. 7217 - 7233
  • 25
  • [ 16932-45-9 ]
  • [ 7051-15-2 ]
Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 46, p. 12886 - 12890
  • 26
  • [ 7321-55-3 ]
  • [ 16932-45-9 ]
  • [ 16932-49-3 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 29, p. 9481 - 9488
  • 27
  • [ 5419-55-6 ]
  • [ 16932-45-9 ]
  • [ 23112-96-1 ]
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
  • 28
  • [ 16932-45-9 ]
  • [ 23112-96-1 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 17, p. 4662 - 4665
  • 29
  • [ 16932-45-9 ]
  • [ 135999-16-5 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 1, p. 42 - 45
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 16932-45-9 ]

Aryls

Chemical Structure| 38603-09-7

[ 38603-09-7 ]

1,3-Dibromo-2-methoxybenzene

Similarity: 0.98

Chemical Structure| 2674-34-2

[ 2674-34-2 ]

1,4-Dibromo-2,5-dimethoxybenzene

Similarity: 0.95

Chemical Structure| 17715-69-4

[ 17715-69-4 ]

1-Bromo-2,4-dimethoxybenzene

Similarity: 0.93

Chemical Structure| 63604-94-4

[ 63604-94-4 ]

2-Bromo-5-methoxyphenol

Similarity: 0.93

Chemical Structure| 102127-34-4

[ 102127-34-4 ]

4-Bromo-3-methoxyphenol

Similarity: 0.93

Bromides

Chemical Structure| 38603-09-7

[ 38603-09-7 ]

1,3-Dibromo-2-methoxybenzene

Similarity: 0.98

Chemical Structure| 2674-34-2

[ 2674-34-2 ]

1,4-Dibromo-2,5-dimethoxybenzene

Similarity: 0.95

Chemical Structure| 17715-69-4

[ 17715-69-4 ]

1-Bromo-2,4-dimethoxybenzene

Similarity: 0.93

Chemical Structure| 63604-94-4

[ 63604-94-4 ]

2-Bromo-5-methoxyphenol

Similarity: 0.93

Chemical Structure| 102127-34-4

[ 102127-34-4 ]

4-Bromo-3-methoxyphenol

Similarity: 0.93

Ethers

Chemical Structure| 38603-09-7

[ 38603-09-7 ]

1,3-Dibromo-2-methoxybenzene

Similarity: 0.98

Chemical Structure| 2674-34-2

[ 2674-34-2 ]

1,4-Dibromo-2,5-dimethoxybenzene

Similarity: 0.95

Chemical Structure| 17715-69-4

[ 17715-69-4 ]

1-Bromo-2,4-dimethoxybenzene

Similarity: 0.93

Chemical Structure| 63604-94-4

[ 63604-94-4 ]

2-Bromo-5-methoxyphenol

Similarity: 0.93

Chemical Structure| 102127-34-4

[ 102127-34-4 ]

4-Bromo-3-methoxyphenol

Similarity: 0.93