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Chemical Structure| 151103-09-2
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Product Details of [ 151103-09-2 ]

CAS No. :151103-09-2 MDL No. :MFCD07779381
Formula : C12H12F2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :AHVVCELVGCPYGI-UHFFFAOYSA-N
M.W : 242.22 Pubchem ID :18973698
Synonyms :

Calculated chemistry of [ 151103-09-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.42
Num. rotatable bonds : 6
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 57.22
TPSA : 35.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.68 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.25
Log Po/w (XLOGP3) : 2.96
Log Po/w (WLOGP) : 3.67
Log Po/w (MLOGP) : 1.58
Log Po/w (SILICOS-IT) : 3.33
Consensus Log Po/w : 2.76

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.07
Solubility : 0.205 mg/ml ; 0.000848 mol/l
Class : Soluble
Log S (Ali) : -3.37
Solubility : 0.104 mg/ml ; 0.000428 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.44
Solubility : 0.0869 mg/ml ; 0.000359 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.11

Safety of [ 151103-09-2 ]

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 [ 151103-09-2 ]

* 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 [ 151103-09-2 ]
  • Downstream synthetic route of [ 151103-09-2 ]

[ 151103-09-2 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 7051-34-5 ]
  • [ 151103-08-1 ]
  • [ 151103-09-2 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: With potassium carbonate; potassium iodide In dimethyl sulfoxide at 70℃; for 1 h;
Stage #2: at 70℃; for 4 h;
55 g of 4-(difluoromethoxy)-3-hydroxybenzaldehyde, 42.42 g of K2C03 (1.05 eq), 4.86 g of Kl (0.1 eq) and 220 mL of dimethylsulphoxide (DMSO) were loaded in a reactor. The mixture was heated at 70°C and kept for 1 h. A mixture previously prepared of 42.65 g of bromomethyl cyclopropane (1.08 eq) and 1 10 mL of DMSO was added for 1 hour. The reaction was kept for 3 h at 70°C, and then cooled at room temperature. Once the temperature was reached, 375 mL of toluene was added. The suspension was filtered to remove the remaining K2C03, and then it was cooled at 0-5°C, and 375 mL of deionised water were loaded. The phases were separated and the organic phase was washed twice with 55 mL of deionised water. The solvent was removed at reduced pressure, obtaining 70 g (yield 99percent) of 3-(cyclopropylmethoxy)-4-(difluoromethoxy)- benzaldehyde as a viscous yellowish fluid.
98.5% With trimethylbenzylammonium bromide; potassium carbonate; potassium iodide In tetrahydrofuran at 0℃; Reflux The 50g (266mmol) 4- difluoromethoxy-3-hydroxybenzaldehyde was dissolved was added potassium carbonate 91.9g (665mmol) in tetrahydrofuran 500mL, potassium iodide was added 2.2g (13.3mmol) and benzyl trimethyl ammonium bromide 3.7g, was added and cooled to 0 bromomethyl cyclopropane 50.6g (375mmol) in tetrahydrofuran (150 mL) solution, stirring the reaction mixture was heated to reflux for 1-3 hours, suction filtered, the filtrate was concentrated under reduced pressure, the residue was was added 2mol / L sodium hydroxide solution to pH10, extracted twice with 500mL of dichloromethane, the solvent of the organic layers were dried over sodium sulfate and removed under reduced pressure to give 3-cyclopropyl-methoxy-4-difluoromethoxy methoxybenzaldehyde 63.5g (261mmol), a yield of 98.5percent.
97% With potassium carbonate In tetrahydrofuran at 0℃; for 14 h; Heating / reflux 4-Difluoromethoxy-3-hydroxybenzaldehyde (10 g, 52.8 mmol) was dissolved in tetrahydrofuran (100 ml) added with potassium carbonate (44 g, 105 mmol), cooled to 0° C. and added with a solution of bromomethylcyclopropane (11 ml, 116.6 mmol) in tetrahydrofuran (50 ml).
The reaction mixture was heated to reflux under stirring for 7 hrs, then fresh bromomethylcyclopropane (5.5 ml, 58.3 mmol) was added and the heating continued for further 7 hrs.
The solvent was removed by vacuum distillation, then the mixture was added with 2 N sodium hydroxide (100 ml) and extracted with dichloromethane (2*100 ml).
The combined organic layers were dried over sodium sulphate (5 g) and the solvent removed under reduced pressure to afford 3-cyclopropylmethoxy-4-difluoromethoxybenzaldehyde (12 g, 50 mmol, 97percent yield), that was used without further purification.
96% With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 20 h; a)
3-cyclopropylmethoxy-4-difluoromethoxy-benzaldehyde

4.70 g (24.98 mmol) 4-difluoromethoxy-3-hydroxybenzaldehyde are placed in 50 ml of dimethylformamide, 4.00 g (29.63 mmol) bromomethylcyclopropane and 3.50 g (25.32 mmol) potassium carbonate are added.
The reaction mixture is heated to 100° C. for 20 hours, then the dimethylformamide is concentrated by evaporation.
The residue is extracted with ethyl acetate and water, the organic phase is dried and evaporated to dryness.
Yield: 5.83 g (96percent of theoretical)
87.7% With 4-methyl-morpholine; zinc(II) nitrate In water; acetonitrile at 55℃; 2) Step 1) 3-hydroxy-4-fluoro-methoxybenzaldehyde (37.6g, 200mmol), bromomethyl cyclopropane(29.7g, 220mmol) and N- methylmorpholine (28.3g, 280mmol) and zinc nitrate (22.7g, 120mol)Carried out in acetonitrile mixed reaction, the reaction temperature of the mixture was 55 , after the reaction,The reaction solution was added water,Extracted with dichloromethane, concentrated, and recrystallized from methanol to give 3-cyclopropylmethoxy-4-difluoromethoxy benzaldehyde 42.5g, yield 87.7percent, purity 99.41percent.
82% With potassium carbonate In DMF (N,N-dimethyl-formamide) Step 1: Prepared as described for intermediate 1, using 3-hydroxy-4-25 difluoromethoxy-benzaldehyde (5 g, 26.89 mmol), anhydrous potassium carbonate (7.4 g, 53.62 mmol) and bromomethyl cyclopropane (4.5 g, 33.3 mmol) in dry DMF (50 ml). The reaction yielded 5.5 g (82 percent) of the product as viscous liquid which was used as such for step 2.
22.5 g With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 24 h; To a solution of 4-(difluoromethoxy)-3-hydroxybenzaldehyde (18.4 g, 98 mmol) in DMF (200 ml), potassium carbonate (29.7 g, 215 mmol) and KI (16.3 g, 98 mmol) were added followed by (bromomethyl)cyclopropane (14.28 ml, 148 mmol), and the resulting suspension was stirred at RT for 24 hours. The mixture was poured into water (800 ml) and extracted with diethyl ether (3×300 ml); the combined organic layers were dried over Na2SO4 and the solvent was removed under vacuum affording 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzaldehyde (22.5 g, 93 mmol, 94.8percent yield, MS/ESI+ 243.1 [MH]+). This product was used without purification.
22.5 g With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 24 h; To a solution of 4-(difluoromethoxy)-3-hydroxybenzaldehyde (18.4 g, 98 mmol) in DMF (200 ml), potassium carbonate (29.7 g, 215 mmol) and KI (16.3 g, 98 mmol) were added followed by (bromomethyl)cyclopropane (14.28 ml, 148 mmol) and the resulting suspension was stirred at RT for 24h. The mixture was poured into water (800 ml) and extracted with diethyl ether (3X300 ml); the combined organic layers were dried over Na2S04 and the solvent was removed under vacuum affording 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzaldehyde (22.5 g, 93 mmol, 94.8percent yield, MS/ESI+ 243.1 [MH] +). This product was used without purification.
31 g With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 2 h; Into the reaction flask added 3-hydroxy-4-difluoromethoxybenzaldehyde (21 g, 0.11 mol), cyclopropylmethyl bromide (18. 1 g, 0.13 mol), K2CO3 (18. 5 g) , then dissolved in 199. 5 g DMF and reacted at 85 ° C for 2 h with stirring. TLC monitoring until the reaction was complete. the reaction solution was filtrated , concentrated with CH2Cl2 , then for liquid extraction added CH2Cl2 , H2O into concentrated solution . The organic phase was dried and concentrated with anhydrous MgSO4 to give 31 g of a pale yellow 3-cyclopropylmethylenedioxy-4-(difluoromethoxy)benzaldehyde solution.

Reference: [1] Patent: WO2014/60464, 2014, A1, . Location in patent: Page/Page column 15
[2] Patent: CN105254559, 2016, A, . Location in patent: Paragraph 0041; 0042
[3] Patent: US2008/15226, 2008, A1, . Location in patent: Page/Page column 10
[4] Patent: US2006/116373, 2006, A1, . Location in patent: Page/Page column 6
[5] Organic and Biomolecular Chemistry, 2018, vol. 16, # 38, p. 6900 - 6908
[6] Patent: CN105523922, 2016, A, . Location in patent: Paragraph 0023; 0032
[7] Patent: WO2004/22536, 2004, A1, . Location in patent: Page 36
[8] Patent: US5449686, 1995, A,
[9] Patent: US2013/79313, 2013, A1, . Location in patent: Paragraph 0965
[10] Research on Chemical Intermediates, 2013, vol. 39, # 5, p. 2107 - 2113
[11] Patent: WO2013/45280, 2013, A1, . Location in patent: Page/Page column 244
[12] Journal of Medicinal Chemistry, 2014, vol. 57, # 3, p. 793 - 816
[13] Patent: US2014/275551, 2014, A1, . Location in patent: Paragraph 0053
[14] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 22, p. 7332 - 7339
[15] Patent: CN106146296, 2016, A, . Location in patent: Paragraph 0018
[16] Patent: CN106883118, 2017, A, . Location in patent: Paragraph 0038; 0046-0048
[17] Patent: CN102964297, 2018, B, . Location in patent: Paragraph 0020-0021; 0277; 0279
  • 2
  • [ 2516-33-8 ]
  • [ 151103-09-2 ]
YieldReaction ConditionsOperation in experiment
96.6% With potassium <i>tert</i>-butylate In 1,4-dioxane at 70 - 75℃; for 4 h; 45.5 g (0.631 mol, 1.2 eq) of cyclopropylmethanol and 70.8 g (0.631 mol, 1.2 eq) of potassium t-butoxide were placed in 200 mL of 1,4-dioxane. To the system were added dropwise 3-fluoro Difluoromethoxybenzaldehyde (100 g, 0.526 mol) in 150 mL of 1,4-dioxane.After completion of the dropwise addition, the system was heated to 70-75 ° C for 4h. After consumption of the raw material was monitored by TLC, the temperature was lowered to room temperature and 500 mL of water was added dropwise to the system to quench the reaction. The resulting mixture was extracted with 500 mL of ethyl acetate and the aqueous phase was reused Extract once with 200 mL of ethyl acetate.The organic phases were combined and concentrated under reduced pressure to give 123.1 g of an oil, yield 96.6percent, HPLC purity 99.5percent
Reference: [1] Patent: CN103304408, 2016, B, . Location in patent: Paragraph 0033; 0035-0037
  • 3
  • [ 25934-52-5 ]
  • [ 1895-39-2 ]
  • [ 151103-09-2 ]
YieldReaction ConditionsOperation in experiment
84% With sodium hydroxide In N,N-dimethyl-formamide at 120℃; for 2 h; To a two-necked 100ml flask was added 3-hydroxy-cyclopentyloxy (1.65g, 8.6mmol), chlorodifluoromethane sodium fluoroacetate (2.44g, 16mmol), NaOH solution (20mmol / L, 0.8ml) and N, N- dimethylformamide (DMF, 12ml), the reaction was heated to 120 2h, thin layer chromatography (TLC ) detecting the progress of the reaction, the reaction was complete after the DMF removed at reduced pressure and the residue was purified by silica gel column chromatography as a colorless oil cyclopentyloxy-4-difluoro-3- methoxybenzaldehyde (z-61.75g, yield 84percent)
Reference: [1] Patent: CN105523954, 2016, A, . Location in patent: Paragraph 0025; 0026
  • 4
  • [ 139-85-5 ]
  • [ 151103-09-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 3, p. 793 - 816
[2] Patent: US2014/275551, 2014, A1,
[3] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 22, p. 7332 - 7339
[4] Patent: CN105254559, 2016, A,
[5] Patent: CN105523922, 2016, A,
[6] Patent: CN102964297, 2018, B,
[7] Organic and Biomolecular Chemistry, 2018, vol. 16, # 38, p. 6900 - 6908
[8] Organic and Biomolecular Chemistry, 2018, vol. 16, # 38, p. 6900 - 6908
  • 5
  • [ 4049-39-2 ]
  • [ 151103-09-2 ]
Reference: [1] Patent: CN105523954, 2016, A,
  • 6
  • [ 1381886-14-1 ]
  • [ 151103-09-2 ]
Reference: [1] Patent: CN105523954, 2016, A,
  • 7
  • [ 121-33-5 ]
  • [ 151103-09-2 ]
Reference: [1] Patent: CN106883118, 2017, A,
  • 8
  • [ 162401-70-9 ]
  • [ 151103-09-2 ]
Reference: [1] Patent: CN106883118, 2017, A,
  • 9
  • [ 405-05-0 ]
  • [ 151103-09-2 ]
Reference: [1] Patent: CN103304408, 2016, B,
  • 10
  • [ 151103-09-2 ]
  • [ 162401-62-9 ]
YieldReaction ConditionsOperation in experiment
97% With sodium chlorite; aminosulfonic acid In water; acetic acid at 20℃; for 1 h; 3-cyclopropylmethoxy-4-difluoromethoxybenzaldehyde (12 g, 50 mmol) and sulfamic acid (7.3 g, 75 mmol) were dissolved in glacial acetic acid (50 ml) and the solution added with a solution of sodium chlorite (8.2 g, 75 mmol) in water (15 ml).
The reaction mixture was stirred at room temperature for 1 hr then water (300 ml) was added so obtaining the precipitation of a solid that was filtered and dried at 40° C. under vacuum (12 g, 48 mmol, 97percent yield).
97% With dihydrogen peroxide; potassium hydroxide In methanol at 65℃; for 1 h; At 65 30percent hydrogen peroxide (1ml) was added 3- cyclopropylmethoxy-4-difluoromethoxy benzaldehyde (1.70g, 7mmol), 50percent potassium hydroxide (3.14g, 28mmol) and methanol ( 10ml) was prepared, stirred IH .. After completion of the reaction, water was added to dilute concentrated hydrochloric acid was adjusted to PH 2, there are a lot of white solid precipitated, filtered to give pure 3- cyclopropylmethoxy-4-difluoromethoxy-benzoic acid (z-7,1.75g yield97percent)
97.3% With sodium chlorite; aminosulfonic acid In water; acetic acid at 20℃; for 1 h; 24.2 g (100 mmol) of 3-cyclopropylmethoxy-4-difluoromethoxybenzaldehyde and 14.6 g (150 mmol) of aminoSulfonic acid was dissolved in 200 mL of glacial acetic acid and to the solution was slowly added 13.6 g (150 mmol) of sodium chlorite in 30 mL of water solubleThe reaction mixture was stirred at room temperature for 1 hour and then water was added to give a solid precipitate which was filtered, washed with pure waterDried to give 25.1 g of an off-white solid, yield 97.3percent
97% With sodium chlorite; aminosulfonic acid; acetic acid In water at 0 - 10℃; for 0.5 h; To the reaction flask, 240 mL of glacial acetic acid, 80 g (0.33 mol) of 3-cyclopropylmethoxy-4-difluoromethoxybenzaldehyde and 48 g (0.49 mol, 1.48 eq) of sulfamic acid were added to the reaction flask and cooled to 0-10 with stirring ° C, and then 53.4g (0.59mol, 1.78eq) of aqueous solution of 120mL sodium chlorite was added dropwise to the system. The temperature was controlled at 0-10 .After the addition was completed, the mixture was incubated for 0.5 h. Then 500 mL of water was added to the system and stirred at room temperature for 1 h. The solid was rinsed with water and dried to obtain 82.7 g of a white solid with a yield of 97percent and a purity of 99.8percent.
90.1% With manganese(IV) oxide; hypochloric acid In tetrahydrofuran; water at 48℃; 3) step 2) to give 3-cyclopropyl-methoxy-4-difluoromethoxy benzaldehyde (24.2g, 100mmol) and an oxidant (12.1 g of) the oxidation reaction, the oxidizing agent by a mass ratio of 4 : 1 MnO2 and HClO composition, the oxidationSolvent for the reaction by the volume ratio of 1: 5 composed of water and THF. The reaction temperature of the oxidation was 48 deg.] C, after the reaction, the reactionSolution was poured into ice-water, adjusted to pH 2, the filter cake was recrystallized from methanol to give 3-cyclopropyl-methoxy-4-difluoromethoxy-benzoicAcid, 23.3g, 90.1percent yield, purity of 99.68percent.
85% at 5 - 20℃; 40 g of 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde 160 mL of glacial acetic acid and 32.0 g of sulphamic acid (2.0 eq) were loaded in a reactor. The mixture was cooled at 5-10°C and the temperature was not allowed to exceed 20°C, adding slowly a previously prepared solution of 44.77 g of sodium chloride and 61 mL of deionised water. After the addition, the reaction was kept for 1 hour at 15-20°C. 450 mL of deionised water was loaded and then it was cooled at 0-5°C and kept for 1 h at this temperature. The solid was filtered and washed four times with 200 mL of deionised water. The product was dried for 15 h at 40°C, obtaining 36 g (yield 85percent) of 3- (cyclopropylmethoxy)-4-(difluoromethoxy)-benzoic acid (II) as solid.
85%
Stage #1: at 20℃; for 0.5 h;
Stage #2: With sodium chlorite; aminosulfonic acid; sodium chloride In water at 5 - 20℃;
Acetic acid (20 mL) and 3-cyclopropylmethoxy-4-difluoromethoxybenzaldehyde (5.0 g, 0.02πο1) were added to the reaction flask and stirred at room temperature for 0.5 hour. Then, sulfamic acid (2.4 g, 0.025 mol, the reaction solution was cooled to 5 ° C and then 20 wtpercent aqueous sodium chlorite solution (11.2 g, containing sodium chloride 2.24 g, 0.025 mol) was added and then allowed to react at room temperature. TLC Methoxy-4-difluoromethoxybenzaldehyde was dissolved and quenched by the addition of water (100 mL). After stirring for 1 hour, the filter was washed with water and dried to give a white solid 3-cyclopropylmethoxy-4 - difluoromethoxybenzoic acid (4.5 g, yield 85percent, purity 98.6percent, HPLC chromatogram shown in Figure 4). The product was confirmed to be the target product 3-cyclopropylmethoxy-4-difluoromethoxybenzoic acid as shown in Figure 5
7.6 g With potassium permanganate; potassium carbonate In water; acetone at 60℃; for 1 h; To a solution of 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzaldehyde (8.6 g, 35.5 mmol) in acetone (120 ml) and water (60 ml), KMnO4 (13.1 g, 70.8 mmol) was added and the reaction was heated at 60° C. for 1 h. K2CO3 (9 g, 65.2 mmol) and water (100 ml) were added, and the resulting mixture was filtered through a celite pad. The filtrate was acidified with HCl 37percent (pH=1) and extracted twice with EtOAc. The organic phase was dried over Na2SO4 and the solvent was removed under vacuum affording 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoic acid (7.6 g, 29.4 mmol, 83percent yield). This product was used without any further purification.
7.6 g With potassium permanganate In water; acetone at 60℃; for 1 h; To a solution of 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzaldehyde (8.6 g, 35.5 mmol) in acetone (120 ml) and water (60 ml), KMn04 (13.1 g, 70.8 mmol) was added and the reaction was heated at 60°C for lh. K2CO3 (9 g, 65.2 mmol) and water (100 ml) were added and the resulting mixture was filtered through a celite pad. The filtrate was acidified with HC1 37percent (pH = 1) and extracted twice with EtOAc. The organic phase was dried over Na2S04 and the solvent was removed under vacuum affording 3-(cyclopropylmethoxy)-4- (difluoromethoxy)benzoic acid (7.6 g, 29.4 mmol, 83percent> yield). This product was used without any further purification.
0.51 kg at 70 - 80℃; for 3 h; Large scale 644 g of the compound of formula I and 3.15 kg of glacial acetic acid were added to the reaction flask,Dropping 0.92 kg of 30percent hydrogen peroxide; heating to 70 ° C for 1 hour,And then heated to 80 ° C for 2 hours or more; then cooled to 30 ° C,Slowly pour into 9.00kg of drinking water, precipitation of solid; cooling to 5-10 , adding 0.36kg sodium thiosulfate aqueous solution, stirring crystallization 0.5 hours, pumping, drying, drying,To give 0.51 kg of the compound of formula II.(HPLC purity 99.3percent, 0.1percent single impurities, 3,4 isomers less than 0.03percent).

Reference: [1] Patent: US2008/15226, 2008, A1, . Location in patent: Page/Page column 10
[2] Patent: CN105523954, 2016, A, . Location in patent: Paragraph 0025; 0027
[3] Patent: CN105254559, 2016, A, . Location in patent: Paragraph 0043; 0044
[4] Patent: CN103304408, 2016, B, . Location in patent: Paragraph 0038; 0039
[5] Patent: CN105523922, 2016, A, . Location in patent: Paragraph 0023; 0029; 0033
[6] Patent: WO2014/60464, 2014, A1, . Location in patent: Page/Page column 15
[7] Patent: CN106883118, 2017, A, . Location in patent: Paragraph 0038; 0049-0051
[8] Patent: WO2004/22536, 2004, A1, . Location in patent: Page 36-37
[9] Patent: US2013/79313, 2013, A1, . Location in patent: Paragraph 0966
[10] Research on Chemical Intermediates, 2013, vol. 39, # 5, p. 2107 - 2113
[11] Patent: WO2013/45280, 2013, A1, . Location in patent: Page/Page column 244
[12] Journal of Medicinal Chemistry, 2014, vol. 57, # 3, p. 793 - 816
[13] Patent: US2014/275551, 2014, A1, . Location in patent: Paragraph 0054
[14] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 22, p. 7332 - 7339
[15] Patent: CN106916061, 2017, A, . Location in patent: Paragraph 0037; 0038; 0039; 0040; 0041; 0042
[16] Patent: CN102964297, 2018, B, . Location in patent: Paragraph 0020-0021; 0277; 0280
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3-(Difluoromethoxy)-4-hydroxybenzaldehyde

Similarity: 0.87

Chemical Structure| 127842-54-0

[ 127842-54-0 ]

3,4-Bis(difluoromethoxy)benzaldehyde

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Chemical Structure| 85684-61-3

[ 85684-61-3 ]

3-(Difluoromethoxy)benzaldehyde

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Chemical Structure| 73960-07-3

[ 73960-07-3 ]

4-(Difluoromethoxy)benzaldehyde

Similarity: 0.82