Home Cart 0 Sign in  
X

[ CAS No. 63697-96-1 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 63697-96-1
Chemical Structure| 63697-96-1
Chemical Structure| 63697-96-1
Structure of 63697-96-1 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 63697-96-1 ]

Related Doc. of [ 63697-96-1 ]

Alternatived Products of [ 63697-96-1 ]

Product Details of [ 63697-96-1 ]

CAS No. :63697-96-1 MDL No. :MFCD05664348
Formula : C9H6O Boiling Point : -
Linear Structure Formula :- InChI Key :BGMHQBQFJYJLBP-UHFFFAOYSA-N
M.W :130.14 Pubchem ID :2771645
Synonyms :

Calculated chemistry of [ 63697-96-1 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.76
TPSA : 17.07 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) : -5.94 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.76
Log Po/w (XLOGP3) : 1.63
Log Po/w (WLOGP) : 1.56
Log Po/w (MLOGP) : 2.01
Log Po/w (SILICOS-IT) : 2.62
Consensus Log Po/w : 1.92

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.05
Solubility : 1.16 mg/ml ; 0.00888 mol/l
Class : Soluble
Log S (Ali) : -1.6
Solubility : 3.26 mg/ml ; 0.0251 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.39
Solubility : 0.529 mg/ml ; 0.00406 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.45

Safety of [ 63697-96-1 ]

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 [ 63697-96-1 ]

* 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 [ 63697-96-1 ]
  • Downstream synthetic route of [ 63697-96-1 ]

[ 63697-96-1 ] Synthesis Path-Upstream   1~25

  • 1
  • [ 63697-96-1 ]
  • [ 1791-26-0 ]
  • [ 4748-78-1 ]
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 5, p. 1481 - 1485
[2] Chemistry - A European Journal, 2017, vol. 23, # 25, p. 6019 - 6028
  • 2
  • [ 63697-96-1 ]
  • [ 4748-78-1 ]
Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 42, p. 17037 - 17044
[2] Chemistry - A European Journal, 2017, vol. 23, # 25, p. 6019 - 6028
  • 3
  • [ 63697-96-1 ]
  • [ 768-59-2 ]
  • [ 4748-78-1 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 25, p. 6019 - 6028
  • 4
  • [ 63697-96-1 ]
  • [ 622-96-8 ]
  • [ 768-59-2 ]
  • [ 4748-78-1 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 25, p. 6019 - 6028
  • 5
  • [ 63697-96-1 ]
  • [ 622-96-8 ]
  • [ 768-59-2 ]
  • [ 1791-26-0 ]
  • [ 4748-78-1 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 25, p. 6019 - 6028
  • 6
  • [ 63697-96-1 ]
  • [ 98-80-6 ]
  • [ 57341-98-7 ]
YieldReaction ConditionsOperation in experiment
89% With nickel(II) (2-((3-methylthiophen-2-yl)methylene)hydrazinecarbothioamide)2.; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 100℃; for 5 h; General procedure: In an oven-dried round-bottom flask, a mixture of arylboronic acid (1.0 mmol), phenylacetylene (1.2 mmol), complex 1 (5.0 molpercent), and 1,8-diazabicycloundec-7-ene(DBU) (2.0 mmol) in DMF (5 mL) was taken. The reaction mixture was stirred at 100°C in air for 5 h. At the end of this time, the reaction mixture was diluted with EtOAc(20 mL) and washed with water (3 9 10 mL). The organic layer was dried over anhydrous Na2SO4, filtered and the solvent was stripped off under reduced pressure. The residue was subjected to column chromatography on silica gel using ethyl acetate and n-hexane mixture to afford the desired product. The products were characterized by 1H and 13C NMR analysis.
Reference: [1] Transition Metal Chemistry, 2017, vol. 42, # 7, p. 579 - 585
  • 7
  • [ 591-50-4 ]
  • [ 63697-96-1 ]
  • [ 57341-98-7 ]
YieldReaction ConditionsOperation in experiment
76% at 35 - 40℃; Inert atmosphere General procedure: A mixture of PdCl2(PPh3)2 (11 mg, 0.016 mmol, 0.01 equiv), Et3N (4.7 mL, 34 mmol), 4-ethynylbenzaldehyde (1e)4f,g (201 mg, 1.55 mmol, 1.0 equiv), and iodobenzene derivative (1.63 mmol) was stirred at room temperature for 5 min; CuI (6 mg, 0.03 mmol, 0.02 equiv) was added and the mixture was stirred at 35-40 °C for 17-24 h under an argon atmosphere.4e After being cooled to room temperature, the mixture was diluted with EtOAc and washed with brine. The organic layer was dried over MgSO4, filtered, concentrated, and purified by flash column chromatography to afford 2.
Reference: [1] Tetrahedron, 2013, vol. 69, # 20, p. 4098 - 4104
  • 8
  • [ 66003-78-9 ]
  • [ 63697-96-1 ]
  • [ 57341-98-7 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 19, p. 5454 - 5457
  • 9
  • [ 108-86-1 ]
  • [ 63697-96-1 ]
  • [ 57341-98-7 ]
Reference: [1] Chinese Chemical Letters, 2012, vol. 23, # 2, p. 185 - 188
  • 10
  • [ 63697-96-1 ]
  • [ 108-90-7 ]
  • [ 57341-98-7 ]
Reference: [1] Chinese Chemical Letters, 2012, vol. 23, # 2, p. 185 - 188
  • 11
  • [ 63697-96-1 ]
  • [ 10602-04-7 ]
YieldReaction ConditionsOperation in experiment
90% at 0 - 20℃; for 2 h; A solution of 543 4-ethynylbenzaldehyde (3.8 g, 29.23 mmol) in 124 methanol (80 mL) at 0° C. was charged with 246 sodium borohydride (2.2 g, 58.46 mmol) portionwise. The reaction mixture allowed to attain room temperature and stirred for 2 h. The reaction mixture was concentrated in vacuo, quenched with saturated ammonium chloride solution and extracted with ethyl acetate The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford 3.47 g, 90percent yield, of the title compound as light yellow oil.1H NMR (400 MHz, CDCl3) δ=7.49 (d, J=7.83 Hz, 2H), 7.33 (d, J=7.82 Hz, 2H), 4.71 (s, 2H), 3.07 (s, 1H).
66.7% at 20℃; for 8 h; The p-alkynylbenzaldehyde (390 mg, 3 mmol) was dissolved in 15 mL of dry EtOH.Sodium borohydride (567 mg, 15 mmol) was dissolved in a small amount of dry EtOH, slowly added dropwise to the reaction system, and reacted at room temperature for 8 h.After the reaction was completed, H2O was added dropwise to the system to quench the unreacted sodium borohydride, then the solvent was deconcentrated, extracted with DCM, and washed three times with saturated NaCl.The organic phase was dried over anhydrous Na2SO4, filtered, concentrated and purified by column eluting with MeOH and DCM (volume ratio 1:3) to give 264 mg of compound 1 as a pale yellow solid. The yield was 66.7percent.
61%
Stage #1: With sodium tetrahydroborate In methanol at 0 - 20℃; for 1.08333 h;
Stage #2: With ammonium chloride In methanol
To a solution of 4-Ethynyl-benzaldehyde (1.8 g, 13.8 mmol) in methanol (40 mL) was added NaBH4; (1.04 g, 27.1 mmol) at 0 °C over a period of 5 min. The reaction mixture was allowed to stir at 25 °C over a period of 60 min. The reaction mixture quenched with saturated ammonium chloride and the solvent was evaporated under reduced pressure. The crude product was diluted with ethyl acetate (200 mL) washed with water (2X 50 mL) dried over sodium sulphate and it was evaporated under reduced pressure to give (4-Ethynyl-phenyl)-methanol as a light yellow oil (1.1 g, 61 percent)
61%
Stage #1: With sodium tetrahydroborate In methanol at 0 - 25℃; for 1.08333 h;
Stage #2: With ammonium chloride In methanol
To a solution of 4-Ethynyl-benzaldehyde (1.8 g, 13.8 mmol) in methanol (40 mL) was added NaBH4 (1.04 g, 27.1 mmol) at 0° C. over a period of 5 min.
The reaction mixture was allowed to stir at 25° C. over a period of 60 min.
The reaction mixture quenched with saturated ammonium chloride and the solvent was evaporated under reduced pressure.
The crude product was diluted with ethyl acetate (200 mL) washed with water (2*50 mL) dried over sodium sulphate and it was evaporated under reduced pressure to give (4-Ethynyl-phenyl)-methanol as a light yellow oil (1.1 g, 61percent).

Reference: [1] Chemistry - An Asian Journal, 2018, vol. 13, # 22, p. 3491 - 3500
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 1573 - 1578
[3] Journal of the American Chemical Society, 2009, vol. 131, # 2, p. 634 - 643
[4] Patent: US2017/202970, 2017, A1, . Location in patent: Paragraph 0728; 0733; 0734
[5] Patent: CN107365254, 2017, A, . Location in patent: Paragraph 0115; 0126-0128
[6] Patent: WO2011/21209, 2011, A1, . Location in patent: Page/Page column 35; 36
[7] Patent: US2012/101099, 2012, A1, . Location in patent: Page/Page column 12
[8] Green Chemistry, 2009, vol. 11, # 9, p. 1313 - 1316
[9] ChemMedChem, 2011, vol. 6, # 11, p. 2009 - 2018
[10] Journal of the American Chemical Society, 2014, vol. 136, # 6, p. 2520 - 2528
[11] Chemical Communications, 2017, vol. 53, # 30, p. 4215 - 4218
  • 12
  • [ 38846-64-9 ]
  • [ 63697-96-1 ]
  • [ 10602-04-7 ]
  • [ 10602-08-1 ]
Reference: [1] Journal of the American Chemical Society, 2000, vol. 122, # 19, p. 4817 - 4818
  • 13
  • [ 77123-57-0 ]
  • [ 63697-96-1 ]
YieldReaction ConditionsOperation in experiment
97% With potassium hydroxide In tetrahydrofuran; water at 20℃; for 2 h; Compound 4 (727 mg, 3.6 mmol) was dissolved in 15 mL of anhydrous THF and 2 mL of aqueous KOH solution was added(298 mg, 4 mmol), reacted at room temperature for 2 h. The THF was spin-dried. The reaction was extracted with EA and washed three times with saturated NaCl solution.The organic phase was dried over anhydrous Na2SO4, filtered, concentrated, and purified by column chromatography with PE and DCM (1:1 by volume) to give 450 mg of compound 5 as a pale yellow solid. The yield is 97percent.
94% at 20℃; for 2 h; B. 4-ethynylbenzaldehyde; A degassed solution of 4-bromobezaldehyde (6.0 g, 32.4 mmol) and triphenylphosphine (0.17 g, 0.65 mmol) in 60 mL of anhydrous triethylamine was added ethynyltrimethylsilane (26.7 mL, 48.6 mmol) followed by palladium (II) acetate (0.072 g, 0.32 mmol) at room temperature under argon atmosphere. The reaction mixture was heated at reflux for 2 h in sealed tube. The reaction mass was cooled to room temperature and the precipitated solid was filtered. The filtrate was concentrated to provide crude compound. The crude compound was purified by column chromatography (silica gel, 100-200 mesh) by using 1percent ethyl acetate in pet-ether as mobile phase to provide 4- ((trimethylsilyl)ethynyl)benzaldehyde (5.2 g, 80percent). This compound was taken up in methanol (100 mL), to which potassium carbonate (0.341 g, 2.47 mmol) was added at room temperature. The reaction mass was stirred for 2 h. The solvent was removed under reduced pressure and the residue was diluted with dichloromethane (50 mL). The organic solution was washed with water (50 mL), brine solution (25 mL), dried over anhydrous magnesium sulfate and evaporated under reduced pressure to get 4-ethynylbenzaldehyde as light brown solid (3.0 g, 94percent).LC-MS: [M+H]+ 131.2 Mass: calculated for C9H6O, 130.15IH NMR (400 MHz, δ ppm, CDC13): δ 10.02 (s, IH), 7.85 (d, 2H), 7.65 (d, 2H), 3.29 (s, IH)
90% With potassium hydroxide In methanol; dichloromethane at 20℃; for 6 h; 4-((Trimethylsilyl)ethynyl)benzaldehyde (2.0 g, 10.0 mmol) and KOH (561 mg, 10.0 mmol) were dissolved in the mixed solvents of CH2Cl2 (10 mL) and MeOH (5 mL). The mixture was stirred at room temperature for 6 h, and then the solvent was concentrated under reduced pressure. H2O (20 mL) and CH2Cl2 (20 mL) were added to the obtained residue to afford a two-phase solution. The aqueous layer was extracted with CH2Cl2 (2 × 20 mL), and the combined organic layers were washed with H2O, and then dried over MgSO4. The solution was filtered, and the solvent was removed by rotary evaporation to give a light yellow powder identified as 4-ethynylbenzaldehyde 2 (1.17 g, 90percent). 1H NMR (300 MHz, CDCl3) δ 10.01 (s, 1H), 7.86-7.81 (m, 2H), 7.63 (d, J = 8.2 Hz, 2H), 3.32 (s, 1H). ESI-MS: m/z: 129.17 [M − H].
85.5% With potassium carbonate In methanol; dichloromethane; Petroleum ether This compound (8.00 g, 39.59 mmol) was treated with K2CO3 (0.500 g) in methanol (50 mL) at 25° C. for 2 hours under Argon.
The solvent was removed under vacuum, and the residue was dissolved in dichloromethane (100 mL).
This solution was washed once with a saturated aqueous NaHCO3 solution, and once with water, was then dried over anhydrous Na2SO4, and the solvent was evaporated under vacuum.
The yellow residue was purified by column chromatography using dichloromethane/petroleum ether 1:4, and then recrystallized from cold cyclohexane to give 4.40 g (85.5percent yield) of the title compound; MS (EI) m/e 130.0; (M+).
1H-NMR (CDCl3) δ ppm: 3.30 (s, 1H, CH), 7.64 (d, 2H, ArH, J=8.1 Hz), 7.84 (d, 2H, ArH, J=8.1 Hz), 10.02 (s, 1H, CHO).
85.5% With potassium carbonate In methanol; dichloromethane; Petroleum ether This compound (8.00 g, 39.59 mmol) was treated with K2CO3 (0.500 g) in methanol (50 mL) at 25° C. for 2 hours under Argon.
The solvent was removed under vacuum, and the residue was dissolved in dichloromethane (100 mL).
This solution was washed once with a saturated aqueous NaHCO3 solution, and once with water, was then dried over anhydrous Na2SO4, and the solvent was evaporated under vacuum.
The yellow residue was purified by column chromatography using dichloromethane/petroleum ether 1:4, and then recrystallized from cold cyclohexane to give 4.40 g (85.5percent yield) of the title compound; MS (El) m/e 130.0; (M+).
1H-NMR (CDCl3) δ ppm: 3.30 (s, 1H, CH), 7.64 (d, 2H, ArH, J=8.1 Hz), 7.84 (d, 2H, ArH, J=8.1 Hz), 10.02 (s, 1H, CHO).
85.5% With potassium carbonate In methanol at 25℃; for 2 h; This compound (8.00 g, 39.59 mmol) was treated with K2CO3 (0.500 g) in methanol (50 mL) at 25 C. for 2 hours, under Argon. The solvent was removed under vacuum and the residue dissolved in dichloromethane (100 mL). This solution was washed once with an aqueous saturated solution of NaHCO3 and once with water, before being dried over anhydrous Na2SO4 and the solvent evaporated under vacuum. The yellow residue was purified by column chromatography using dichloromethane/petroleum ether 1:4 for elution and recrystallization from cold cylohexane to give 4.40 g (85.5percent yied) of the title compound; MS (EI) m/e 130.0; (M+). 1H-NMR (CDCl3) ? ppm: 3.30 (s, 1H, CH), 7.64 (d, 2H, ArH, J=8.1 Hz), 7.84 (d, 2H, ArH, J=8.1 Hz), 10.02 (s, 1H, CHO).
85% at 20℃; for 24 h; A deaerated solution of 4-bromobenzaldehyde (3, 4.87 g, 25 mmol),triphenylphosphine (0.33 g, 1.25 mmol), PdCl2 (45 mg, 0.25 mmol), and Cu(OAc)2 (48 mg, 0.25 mmol) inanhydrous triethylamine (60 mL) was treated with trimethylsilylacetylene (5.5 mL, 38 mmol). The mixture wasbrought to reflux for 6 h. After cooling, the precipitated triethylamine hydrobromide was filtered off, and thesolvent was evaporated. The crude material was purified by silica gel column chromatography (silica gel 120 g,hexanes/ethyl acetate = 90/10), affording 4-((trimethylsilyl)ethynyl)benzaldehyde (4.49 g, 89percent yield) as a yellowsolid. 4-((Trimethylsilyl)ethynyl)benzaldehyde (4.05 g, 20 mmol) was treated with K2CO3 (2.28 mg, 2 mol) inMeOH (24 mL) at room temperature for 24 h. The solvent was removed in vacuo. The crude material was purifiedby silica gel column chromatography (silica gel 120 g, hexanes/ethyl acetate = 90/10), affording 4-ethynylbenzaldehyde (5; 2.20 g, 85percent yield) as a yellow solid.
84% With potassium carbonate In methanol at 20℃; for 24 h; To a mixture of PdCl2(PPh3)2 (175 mg, 0.3 mmol) andCuI (190 mg, 1.0 mmol) in THF (30 mL), 4-bromobenzaldehyde (1.85 g, 10 mmol), trimethylsilyl acetylene(1.12 mL, 12 mmol), and NEt3 (10 mL) were added.The resulted mixture was stirred for 24 h at room temperature.The solvent was removed and 30 mL CH2Cl2 wasadded. The mixture was washed with water (3 30 mL). Theorganic phase was dried with MgSO4 and the solvent wasremoved by rotary evaporation. Purification by columnchromatography (Silica gel, CH2Cl2/hexane 1:2) gave 4-(2-(trimethylsilyl)ethynyl) -benzaldehyde derivative as whitesolid (yield 85percent).To a stirred solution of 4-(2-(trimethylsilyl)ethynyl) benzaldehyde(5 mmol) in CH3OH (30 mL), K2CO3 (69 mg, 0.5mmol) was added. The mixture was stirred for 24 h at roomtemperature, and the solvent was removed. The residue wasdiluted with 30 mL Et2O and washed with water (3 30mL). The organic phase was dried over MgSO4 and the solventwas removed by rotary evaporation. Purification by aflash colum chromatography (Silica gel, Et2O) provide 5 aswhite solid (546 mg, yield 84percent).1H NMR (400 MHz, CDCl3) 10.04 (s, 1H), 7.87 (d, J =8.0, 2H), 7.67 (d, J = 8.0, 2H), 3.32 (s, 1H).
81% With potassium carbonate In methanol at 20℃; for 1 h; A solution of 545 4-((trimethylsilyl)ethynyl)benzaldehyde (7.5 g, 37.12 mmol) in 124 methanol (100 mL) was charged with 63 potassium carbonate (512 mg, 3.712 mmol) and stirred at room temperature for 1 h. The reaction mixture was concentrated in vacuo, diluted with ethyl acetate and separated organic layer was washed with water. The separated organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo resulting in the crude 543 compound which was purified by column chromatography on silica gel eluting with 0-20percent ethyl acetate in n-hexane to afford 1.2 g, 81percent yield, of the title compound as light yellow solid. 1H NMR (400 MHz, CDCl3) δ=10.02 (s, 1H), 7.85 (d, J=7.83 Hz, 2H), 7.64 (d, J=8.31 Hz, 2H), 3.30 (s, 1H).
75% at 20℃; for 3 h; A solution of p-bromobenzaldehyde (2 mmol, 370 mg)Was dissolved in 15 ml of anhydrous triethylamine,Vacuum,Replaced with argon three times,Weigh Pd (PPh3) 2Cl2 (0.06 mmol, 43 mg)PPh3 (0.06 mmol, 16 mg),CuI (0.02 mmol, 4 mg) was added.Then, 0.5 ml of trimethylsilylacetylene was injected.Heated to 70 degrees,The reaction was carried out for 6 hours and after cooling to room temperature,Filter out a white solid,Wash the filter cake several times with CH2Cl2.The solvent was removed under reduced pressure.Silica gel column.The resulting brown solid was then dissolved in methanol,K2CO3 (2 mmol, 390 mg)Room temperature reaction for 3 hours,Filter K2CO3,Pressurized to remove methanol,Over silica gel column,EluentFor petroleum ether: dichloromethane (1: 1),To obtain 195 mg,The yield was 75percent.
72% at 25℃; for 1 h; To a solution of 4-Trimethylsilanylethynyl-benzaldehyde (4.0 g, 19.7 mmol) in methanol (50 mL) was added K2CO3 (275 mg, 1.97 mmol) at 25 °C. The reaction mixture stirred at same temperature over a period of 60 min. Methanol was evaporated to the half volume at 35 °C and it was diluted with ethyl acetate (500 mL). The organic layer washed with water (2X100 mL) and dried over sodium sulphate and it was evaporated under reduced pressure to obtain crude product. The crude product was further purified by column chromatography to give 4-Ethynyl-benzaldehyde as a light yellow solid (1.8 g, 72 percent)
72%
Stage #1: With potassium carbonate In methanol at 25℃; for 1 h;
Stage #2: With water In methanol; ethyl acetate
To a solution of 4-Trimethylsilanylethynyl-benzaldehyde (4.0 g, 19.7 mmol) in methanol (50 mL) was added K2CO3 (275 mg, 1.97 mmol) at 25° C.
The reaction mixture stirred at same temperature over a period of 60 min.
Methanol was evaporated to the half volume at 35° C. and it was diluted with ethyl acetate (500 mL).
The organic layer washed with water (2*100 mL) and dried over sodium sulphate and it was evaporated under reduced pressure to obtain crude product.
The crude product was further purified by column chromatography to give 4-Ethynyl-benzaldehyde as a light yellow solid (1.8 g, 72percent).
71% With potassium carbonate In methanol at 20℃; To a solution of 4-((trimethylsilyl)ethynyl)benzaldehyde (1.63 g, 8.06 mmol) in CH3OH (15 mL) was added K2CO3 (112 mg, 0.810 mmol). The reaction mixture was stirred at room temperature overnight and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, petroleum benzine ramping to petroleum benzine:EtOAc = 98:2) to give 10 as a pale yellow solid (750 mg, 71percent). RF (EtOAc:hexane = 1:5) 0.56. m.p. 9192 °C (lit. [7] m.p. 87 °C). IR νmax/cm-1 3223, 2837, 2739, 1695, 1601, 1561, 1388, 1294, 1207, 1165, 829. 1H NMR (400 MHz, CDCl3) δ 3.31 (s, 1H, C≡CH), 7.63 (d, 2H, J 8.0, Ph-H), 7.84 (d, 2H, J 8.0, Ph-H), 10.0 (s, 1H, CHO). 13C NMR (100 MHz, CDCl3) δ 81.2, 82.7, 128.4, 129.6, 132.8, 136.1, 191.5 (two carbon signals overlapping or obscured). MS (GC-EI) 101.0 ([MCHO]+, 41percent), 129.0 (M+, 100percent). The spectroscopic data were in agreement with those in the literature [7].
0.29 g With potassium carbonate In methanol at 20℃; for 1 h; A mixture of 4-((trimethylsilyl)ethynyl)benzaldehyde 4 (1g, 4.94 mmol) and potassium carbonate (1g, 7.41 mmol) were stirred in methanol (25 mL) at room temperature for 1 hour. The reaction mixture was diluted with ethylacetate (20 mL) and washed with water (2 x 20 mL) followed by brine solution. The organic solvent was concentrated under reduced pressure to obtain compound 5. Yellow solid; Yield: 0.29 g (90percent); M.p.: 84-86°C;IR (KBr): Umax 3454, 329, 3220, 2836, 2784, 2739, 2098, 1930, 1699, 1686, 1601, 1560, 1408, 1386, 1364, 1303, 1286, 1206, 1163, 1102, 1012, 975, 954, 924, 844, 829, 739, 679, 581, 530, 508 cm-1;1H NMR (400 MHz, CDCl3): d3.30 (1 H, s), 7.66 (d, J = 8.20 Hz, 2H), 7.86 (d, J = 8.20 Hz, 2H), 10.02 (s, 1H).

Reference: [1] Journal of the American Chemical Society, 2009, vol. 131, # 2, p. 634 - 643
[2] Chemical Communications, 2011, vol. 47, # 4, p. 1282 - 1284
[3] Journal of Materials Chemistry A, 2013, vol. 1, # 34, p. 10008 - 10015
[4] ChemPhysChem, 2016, p. 2066 - 2078
[5] Journal of the American Chemical Society, 2016, vol. 138, # 51, p. 16703 - 16710
[6] Patent: CN107365254, 2017, A, . Location in patent: Paragraph 0115; 0121-0123
[7] Journal of Organic Chemistry, 2003, vol. 68, # 21, p. 8025 - 8036
[8] Chemistry - A European Journal, 2003, vol. 9, # 19, p. 4661 - 4669
[9] Organic Letters, 2008, vol. 10, # 21, p. 4979 - 4982
[10] Journal of the American Chemical Society, 2011, vol. 133, # 33, p. 13036 - 13054
[11] Chemical Communications, 2013, vol. 49, # 17, p. 1717 - 1719
[12] Organic Letters, 2000, vol. 2, # 2, p. 111 - 113
[13] Chemistry - A European Journal, 2001, vol. 7, # 23, p. 5118 - 5134
[14] New Journal of Chemistry, 2011, vol. 35, # 1, p. 127 - 136
[15] European Journal of Organic Chemistry, 2018, vol. 2018, # 15, p. 1756 - 1760
[16] Tetrahedron Letters, 2000, vol. 41, # 7, p. 1015 - 1018
[17] Patent: WO2010/100475, 2010, A1, . Location in patent: Page/Page column 48-49
[18] New Journal of Chemistry, 2005, vol. 29, # 10, p. 1272 - 1284
[19] Journal of the American Chemical Society, 2012, vol. 134, # 40, p. 16671 - 16692
[20] Chemical Communications (Cambridge, United Kingdom), 2012, vol. 48, # 92, p. 11289 - 11291,3
[21] Polymer, 2012, vol. 53, # 26, p. 6033 - 6038
[22] Angewandte Chemie - International Edition, 2017, vol. 56, # 42, p. 13094 - 13098[23] Angew. Chem., 2017, vol. 56, p. 13274 - 13278,5
[24] Patent: US2004/106592, 2004, A1,
[25] Patent: US2004/116385, 2004, A1,
[26] Patent: US2004/14737, 2004, A1, . Location in patent: Page 5
[27] Organic Letters, 2013, vol. 15, # 4, p. 936 - 939
[28] Tetrahedron Letters, 2014, vol. 55, # 11, p. 1946 - 1948
[29] Letters in Organic Chemistry, 2013, vol. 10, # 1, p. 22 - 26
[30] Chemical Communications, 2016, vol. 52, # 13, p. 2843 - 2845
[31] Tetrahedron Letters, 2007, vol. 48, # 33, p. 5817 - 5820
[32] Angewandte Chemie - International Edition, 2017, vol. 56, # 2, p. 568 - 572[33] Angew. Chem., 2017, vol. 129, p. 583 - 587,5
[34] Patent: US2017/202970, 2017, A1, . Location in patent: Paragraph 0738; 0736; 0737
[35] New Journal of Chemistry, 2018, vol. 42, # 1, p. 555 - 563
[36] Chemical Communications, 2015, vol. 51, # 25, p. 5257 - 5260
[37] Patent: CN106946838, 2017, A, . Location in patent: Paragraph 0065; 0066; 0067
[38] Patent: WO2011/21209, 2011, A1, . Location in patent: Page/Page column 35; 36
[39] Patent: US2012/101099, 2012, A1, . Location in patent: Page/Page column 12
[40] Beilstein Journal of Organic Chemistry, 2014, vol. 11, p. 37 - 41
[41] ChemPlusChem, 2014, vol. 79, # 9, p. 1352 - 1360
[42] Tetrahedron, 1998, vol. 54, # 27, p. 7721 - 7734
[43] Journal of Materials Chemistry C, 2016, vol. 4, # 14, p. 2843 - 2853
[44] Chemistry - A European Journal, 2014, vol. 20, # 44, p. 14282 - 14295
[45] Journal of Organic Chemistry, 1981, vol. 46, # 11, p. 2280 - 2286
[46] Tetrahedron Letters, 2000, vol. 41, # 40, p. 7623 - 7627
[47] Patent: US4465833, 1984, A,
[48] Journal of Organic Chemistry, 2009, vol. 74, # 6, p. 2417 - 2424
[49] Advanced Synthesis and Catalysis, 2010, vol. 352, # 14-15, p. 2405 - 2410
[50] Chemistry Letters, 2011, vol. 40, # 2, p. 184 - 185
[51] European Journal of Organic Chemistry, 2011, # 25, p. 4773 - 4787
[52] Tetrahedron, 2012, vol. 68, # 31, p. 6338 - 6342
[53] Organic Letters, 2013, vol. 15, # 4, p. 840 - 843
[54] Chemistry - An Asian Journal, 2011, vol. 6, # 6, p. 1604 - 1612
[55] Journal of Polymer Science, Part A: Polymer Chemistry, 2013, vol. 51, # 24, p. 5248 - 5256
[56] Reactive and Functional Polymers, 2015, vol. 87, p. 46 - 52
[57] Angewandte Chemie - International Edition, 2014, vol. 53, # 31, p. 8216 - 8220[58] Angew. Chem., 2014, vol. 126, # 31, p. 8355 - 8359,5
[59] Journal of Materials Chemistry C, 2014, vol. 2, # 45, p. 9720 - 9736
[60] Chemistry - A European Journal, 2016, vol. 22, # 16, p. 5583 - 5597
[61] Journal of Molecular Structure, 2017, vol. 1128, p. 361 - 367
[62] Oriental Journal of Chemistry, 2016, vol. 32, # 4, p. 2155 - 2161
[63] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 2250 - 2255
[64] Chemical Communications, 2018, vol. 54, # 35, p. 4465 - 4468
  • 14
  • [ 1122-91-4 ]
  • [ 1066-54-2 ]
  • [ 63697-96-1 ]
YieldReaction ConditionsOperation in experiment
85.1%
Stage #1: With triethylamine In tetrahydrofuran for 0.75 h; Inert atmosphere
Stage #2: With copper(l) iodide; triphenylphosphine hydrochloride In tetrahydrofuran for 10 h; Inert atmosphere
Stage #3: With potassium carbonate In methanol at 20℃; for 5 h;
15.0 mmol (2.78 g) of p-bromobenzaldehyde was dissolved in 95 ml of a tetrahydrofuran and triethylamine mixed solution (1: 1 by volume) and placed in a 250 ml single-necked flask,The cells were ventilated for 45 minutes and then 18.0 mmol (1.76 g)Of trimethylsilylacetylene. Adding 97.2 mg of triphenylphosphonium dichloride,46.5mg cuprous iodide. Under argon, the reaction was carried out for 10 hours.After the reaction was stopped, the solvent was removed by distillation under reduced pressure and purified by silica gel column chromatography (developing solvent: dichloromethane: petroleum ether 1: 4), steamed and dried in vacuo to give 2.19 g of a white solid in 72.3percent yield.B: A solution of 8.0 mmol (1.62 g) of a product was dissolved in 30 mlMethanol and 60 ml of tetrahydrofuran, placed in a 250 ml single-necked round bottom flask,Then add anhydrous potassium carbonate,And the mixture was stirred at room temperature for 5 hours. The solvent was distilled off under reduced pressure,Silica gel column (developing solvent for petroleum ether and dichloromethane 1: 1 mixed solvent) crude purification;Dried in vacuo to give 0.88 g of a white solid in 85.1percent
Reference: [1] Patent: CN106588789, 2017, A, . Location in patent: Paragraph 0047-0049
[2] Dalton Transactions, 2013, vol. 42, # 40, p. 14374 - 14379
[3] Journal of Polymer Science, Part A: Polymer Chemistry, 2013, vol. 51, # 19, p. 4070 - 4075
[4] Polyhedron, 2015, vol. 86, p. 10 - 16
[5] Patent: CN107987094, 2018, A, . Location in patent: Paragraph 0038; 0039
  • 15
  • [ 15164-44-0 ]
  • [ 63697-96-1 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 33, p. 5817 - 5820
[2] Chemistry - A European Journal, 2001, vol. 7, # 23, p. 5118 - 5134
[3] Organic Letters, 2000, vol. 2, # 2, p. 111 - 113
[4] Chemical Communications (Cambridge, United Kingdom), 2012, vol. 48, # 92, p. 11289 - 11291,3
[5] Organic Letters, 2013, vol. 15, # 4, p. 936 - 939
[6] Oriental Journal of Chemistry, 2016, vol. 32, # 4, p. 2155 - 2161
  • 16
  • [ 1122-91-4 ]
  • [ 63697-96-1 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 21, p. 8025 - 8036
[2] Russian Chemical Bulletin, 2002, vol. 51, # 1, p. 128 - 134[3] Izvestiya Akademi Nauk, Seriya Khimicheskaya, 2002, # 1, p. 122 - 127
[4] Journal of Organic Chemistry, 1981, vol. 46, # 11, p. 2280 - 2286
[5] Chemical Communications, 2011, vol. 47, # 4, p. 1282 - 1284
[6] Patent: WO2011/21209, 2011, A1,
[7] New Journal of Chemistry, 2011, vol. 35, # 1, p. 127 - 136
[8] Chemistry Letters, 2011, vol. 40, # 2, p. 184 - 185
[9] European Journal of Organic Chemistry, 2011, # 25, p. 4773 - 4787
[10] Patent: US2012/101099, 2012, A1,
[11] Journal of the American Chemical Society, 2012, vol. 134, # 40, p. 16671 - 16692
[12] Polymer, 2012, vol. 53, # 26, p. 6033 - 6038
[13] Chemical Communications, 2013, vol. 49, # 17, p. 1717 - 1719
[14] Letters in Organic Chemistry, 2013, vol. 10, # 1, p. 22 - 26
[15] Chemistry - An Asian Journal, 2011, vol. 6, # 6, p. 1604 - 1612
[16] Journal of Polymer Science, Part A: Polymer Chemistry, 2013, vol. 51, # 24, p. 5248 - 5256
[17] Tetrahedron Letters, 2014, vol. 55, # 11, p. 1946 - 1948
[18] Journal of Materials Chemistry A, 2013, vol. 1, # 34, p. 10008 - 10015
[19] Angewandte Chemie - International Edition, 2014, vol. 53, # 31, p. 8216 - 8220[20] Angew. Chem., 2014, vol. 126, # 31, p. 8355 - 8359,5
[21] Chemistry - A European Journal, 2014, vol. 20, # 44, p. 14282 - 14295
[22] Beilstein Journal of Organic Chemistry, 2014, vol. 11, p. 37 - 41
[23] Chemical Communications, 2015, vol. 51, # 25, p. 5257 - 5260
[24] Reactive and Functional Polymers, 2015, vol. 87, p. 46 - 52
[25] ChemPlusChem, 2014, vol. 79, # 9, p. 1352 - 1360
[26] Chemistry - A European Journal, 2016, vol. 22, # 16, p. 5583 - 5597
[27] Chemical Communications, 2016, vol. 52, # 13, p. 2843 - 2845
[28] ChemPhysChem, 2016, p. 2066 - 2078
[29] Journal of Molecular Structure, 2017, vol. 1128, p. 361 - 367
[30] Journal of the American Chemical Society, 2016, vol. 138, # 51, p. 16703 - 16710
[31] Patent: CN106946838, 2017, A,
[32] Angewandte Chemie - International Edition, 2017, vol. 56, # 42, p. 13094 - 13098[33] Angew. Chem., 2017, vol. 56, p. 13274 - 13278,5
[34] Patent: US2017/202970, 2017, A1,
[35] New Journal of Chemistry, 2018, vol. 42, # 1, p. 555 - 563
[36] Patent: CN107365254, 2017, A,
[37] European Journal of Organic Chemistry, 2018, vol. 2018, # 15, p. 1756 - 1760
[38] Chemical Communications, 2018, vol. 54, # 35, p. 4465 - 4468
  • 17
  • [ 10602-04-7 ]
  • [ 63697-96-1 ]
Reference: [1] Russian Chemical Bulletin, 2002, vol. 51, # 1, p. 128 - 134[2] Izvestiya Akademi Nauk, Seriya Khimicheskaya, 2002, # 1, p. 122 - 127
[3] Chemistry - A European Journal, 2013, vol. 19, # 29, p. 9452 - 9456
  • 18
  • [ 1244044-85-6 ]
  • [ 63697-96-1 ]
Reference: [1] Journal of the American Chemical Society, 2010, vol. 132, # 37, p. 12817 - 12819
  • 19
  • [ 624-38-4 ]
  • [ 63697-96-1 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 33, p. 5817 - 5820
[2] Chemistry - A European Journal, 2001, vol. 7, # 23, p. 5118 - 5134
  • 20
  • [ 117569-57-0 ]
  • [ 63697-96-1 ]
Reference: [1] Russian Chemical Bulletin, 2002, vol. 51, # 1, p. 128 - 134[2] Izvestiya Akademi Nauk, Seriya Khimicheskaya, 2002, # 1, p. 122 - 127
  • 21
  • [ 175203-59-5 ]
  • [ 63697-96-1 ]
Reference: [1] Russian Chemical Bulletin, 2002, vol. 51, # 1, p. 128 - 134[2] Izvestiya Akademi Nauk, Seriya Khimicheskaya, 2002, # 1, p. 122 - 127
  • 22
  • [ 873-75-6 ]
  • [ 63697-96-1 ]
Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 29, p. 9452 - 9456
  • 23
  • [ 275386-60-2 ]
  • [ 63697-96-1 ]
Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 29, p. 9452 - 9456
  • 24
  • [ 1066-26-8 ]
  • [ 1122-91-4 ]
  • [ 63697-96-1 ]
Reference: [1] Liebigs Annales, 1996, # 12, p. 2107 - 2113
  • 25
  • [ 766-96-1 ]
  • [ 68-12-2 ]
  • [ 63697-96-1 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 1573 - 1578
[2] Journal of Organometallic Chemistry, 1986, vol. 311, p. C35 - C38
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 63697-96-1 ]

Aryls

Chemical Structure| 38846-64-9

[ 38846-64-9 ]

2-Ethynylbenzaldehyde

Similarity: 0.91

Chemical Structure| 57341-98-7

[ 57341-98-7 ]

4-(Phenylethynyl)benzaldehyde

Similarity: 0.91

Chemical Structure| 59046-72-9

[ 59046-72-9 ]

2-(Phenylethynyl)benzaldehyde

Similarity: 0.83

Chemical Structure| 189008-33-1

[ 189008-33-1 ]

2-(p-Tolylethynyl)benzaldehyde

Similarity: 0.83

Chemical Structure| 626-19-7

[ 626-19-7 ]

Isophthalaldehyde

Similarity: 0.76

Alkynyls

Chemical Structure| 38846-64-9

[ 38846-64-9 ]

2-Ethynylbenzaldehyde

Similarity: 0.91

Chemical Structure| 57341-98-7

[ 57341-98-7 ]

4-(Phenylethynyl)benzaldehyde

Similarity: 0.91

Chemical Structure| 59046-72-9

[ 59046-72-9 ]

2-(Phenylethynyl)benzaldehyde

Similarity: 0.83

Chemical Structure| 189008-33-1

[ 189008-33-1 ]

2-(p-Tolylethynyl)benzaldehyde

Similarity: 0.83

Chemical Structure| 10602-00-3

[ 10602-00-3 ]

4-Ethynylbenzoic acid

Similarity: 0.74

Aldehydes

Chemical Structure| 38846-64-9

[ 38846-64-9 ]

2-Ethynylbenzaldehyde

Similarity: 0.91

Chemical Structure| 57341-98-7

[ 57341-98-7 ]

4-(Phenylethynyl)benzaldehyde

Similarity: 0.91

Chemical Structure| 59046-72-9

[ 59046-72-9 ]

2-(Phenylethynyl)benzaldehyde

Similarity: 0.83

Chemical Structure| 189008-33-1

[ 189008-33-1 ]

2-(p-Tolylethynyl)benzaldehyde

Similarity: 0.83

Chemical Structure| 626-19-7

[ 626-19-7 ]

Isophthalaldehyde

Similarity: 0.76