403-25-8|1-(Difluoromethyl)-3-nitrobenzene| Ambeed

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Quality Control of [ 403-25-8 ] Purity: 95% SDS Specification

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Product Details of [ 403-25-8 ]

CAS No. :	403-25-8
Formula :	C₇H₅F₂NO₂
M.W :	173.12
SMILES Code :	O=[N+](C1=CC(C(F)F)=CC=C1)[O-]
MDL No. :	MFCD18071057
InChI Key :	QOGPXSPKXMNSLH-UHFFFAOYSA-N
Pubchem ID :	21407905

Safety of [ 403-25-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H319
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 403-25-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	2
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	40.33
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	45.82 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.34
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.71
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.05
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.61
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	0.55
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.05

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.86
Solubility	0.24 mg/ml ; 0.00138 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.33
Solubility	0.0818 mg/ml ; 0.000473 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.38
Solubility	0.72 mg/ml ; 0.00416 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.43 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	2.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.67

Application In Synthesis of [ 403-25-8 ]

* 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.

Downstream synthetic route of [ 403-25-8 ]

[ 403-25-8 ] Synthesis Path-Downstream 1~35

1
[ 619-28-3 ]
[ 403-25-8 ]

References: [1]Chemisches Zentralblatt,1914,vol. 85,p. 1565.
[2]Journal of Organic Chemistry USSR (English Translation),1970,vol. 6,p. 1436 - 1439.
Zhurnal Organicheskoi Khimii,1970,vol. 6,p. 1423 - 1426.

2
[ 99-61-6 ]
[ 403-25-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	With diethylamino-sulfur trifluoride; In dichloromethane; at -78 - 20℃;	Step 1 : DAST (16.5 mL, 125 mmol) was added dropwise to a -78 C solution of 3- nitrobenzaldehyde (3.78 g, 25 mmol) in dichloromethane (20 mL). The mixture was stirred for 15 min and then allowed to warm to room temperature. After 4 hrs, TLC showed incomplete conversion, so the mixture was cooled again to -78 C and additional DAST (1 .5 mL, 125 mmol) was added. The mixture was allowed to warm to room temperature and was stirred overnight. The mixture was poured in ice and dilute NH40H(aq) and extracted 2x with dichloromethane. The combined organic extracts were washed with brine and dried over sodium sulfate. Filtration and solvent evaporation gave a residue which was passed over a short plug of silica eluting with 10% ethyl acetate in hexanes to yield 1 -(difluoromethyl)-3-nitrobenzene (4.3 g, 24.8 mmol, 99%).
97.3%	With diethylamino-sulfur trifluoride; In dichloromethane; at -78 - 20℃; for 15h;	Preparation Example 7-1 The synthesis of 1-(difluoromethyl)-3-nitrobenzene DAST (20 ml, 13.23 mmol) diluted in 5 ml of dichloromethane was slowly dropped at -78 C. into 3-nitrobenzaldehyde (1 g, 6.61 mmol) dissolved in 20 ml of dichloromethane and the mixture was stirred for 15 hours at room temperature. After adding 100 ml of water and extraction with 100 ml of dichloromethane, the organic layer was concentrated under vacuum and column chromatography (ethylacetate/n-hexane, 1/15) was carried out to obtain the title compound (1.11 g, 97.3%) as brown oil. 1H-NMR (400 MHz, CDCl3); δ 8.40 (s, 1H), 8.37-8.35 (m, 1H), 7.87 (d, J=7.6 Hz, 1H), 7.69 (t, J=8.0 Hz, 1H), 6.75 (t, J=56.0 Hz, 1H)
79%	With diethylamino-sulfur trifluoride; In dichloromethane; at -78 - 20℃; for 2h;Inert atmosphere;	To a solution of Compound 1 (0.5 g, 3.3 mmol) in anhydrous DCM (10 mL) was added DAST(1.3 g, 7.95 mmol) drop-wise at -78 C under N2. The reaction mixture was stirred at rt for 2 h, and poured into a beaker containing 5 g of ice, decomposing any unreacted DAST. The mixture was extracted twice with DCM (45 mL). The combined organic layer was washed with 50 mL of water, and dried over anhydrous magnesium sulfate. Evaporation to dryness under reduced pressure gives crude product which was purified by silica gel chromatography (eluted with PE: EA=100: 1) to afford Compound 2 (0.45 g, yield: 79%).

78%	With (bis-(2-methoxyethyl)amino)sulfur trufluoride; In dichloromethane; toluene; at 20℃;	To a solution of 2.6 g (17 mmol) of 3-nitrobenzaldehyde in 5 ml_ of dichloromethane is added 11.4 ml_ of 50% bis(2-methoxyethyl)aminosulfurtrifluoride <n="82"/>solution in toluene. The mixture is stirred overnight at room temperature, washed twice with a saturated aqueous sodium hydrogen carbonate solution then with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue is purified over 150 g of silica gel (eluant heptane/ethyl acetate 85/15) to give 2.3 g (78%) of 1-difluoromethyl-3-nitrobenzene as an oil.1H NMR: 8.4 (s, 1 H) ; 8.35 (d, 1 H, J = 7,5) ; 7.9 (d, 1 H, J = 7.5) ; 7,7 (t, 1 H, J = 7.5) ; 7.0 (t, 1 H1 J = 55)
332 mg	With diethylamino-sulfur trifluoride; In dichloromethane; at -78 - 20℃; for 3h;	To a stirred solution of 3-nitrobenzaldehyde (506 mg, 3.35 mmol) in anhydrous dichloromethane (10 mL) was dropwise added DAST (1.32 mL, 10.04 mmol) at -78 C. The mixture was gradually warmed up to RT and stirred for 3 h. The mixture was quenched with saturated sodium bicarbonate solution and extracted twice with ethyl acetate. The combinedorganic extracts were washed with brine and dried over anhydrous sodium sulfate. The solution was filtered and concentrated under reduced pressure and the residue obtained was purified by silica gel column chromatography to yield 332 mg of the desired compound. The compound was as such taken forward to the next step without characterization.
55 g	With diethylamino-sulfur trifluoride; In dichloromethane; at -78 - 20℃; for 2h;	To a solution of 3-nitrobenzaldehyde (50.0 g, 331 mmol) in DCM (800 ml) was added diethylaminosulfur trifluoride (130 ml, 990 mmol) at -78 C. After stirring at rt for 2 h, the reaction mixture was poured into ice-water and extracted with DCM. The organic phase was concentrated and purified by silica gel chromatography (1000 mesh, petroleum ether: ethyl acetate = 1: 0, then 100: 1) to give 1-(difluoromethyl)-3-nitrobenzene (55.0 g) as yellow oil. 1H NMR (400 MHz, DMSO-d6): δ [ppm] = 8.42-8.38 (m, 2H), 8.06 (d, J = 8.0 Hz, 1H), 7.86-7.82 (m, 1H), 7.22 (t, J = 55.2 Hz, 1H).

References: [1]Patent: WO2011/75515,2011,A1 .Location in patent: Page/Page column 262.
[2]Patent: US2013/72482,2013,A1 .Location in patent: Paragraph 0229-0231.
[3]Patent: WO2013/96744,2013,A1 .Location in patent: Page/Page column 227.
[4]Patent: WO2007/148208,2007,A2 .Location in patent: Page/Page column 79-80.
[5]Tetrahedron,1975,vol. 31,p. 391 - 401.
[6]Advanced Synthesis and Catalysis,2017,vol. 359,p. 2222 - 2228.
[7]Patent: WO2018/215668,2018,A1 .Location in patent: Page/Page column 116.
[8]Patent: EP3800188,2021,A1 .Location in patent: Paragraph 0205-0206.

3
[ 403-25-8 ]
[ 368-99-0 ]

Yield	Reaction Conditions	Operation in experiment
50%	With iron; acetic acid; for 1h;Reflux;	Preparation Example 7-2 The synthesis of 3-(difluoromethyl)aniline 100 mg of Fe was added intio 3 ml of acetic acid and refluxed for 15 minutes. After lowering the temperature into room temperature, the mixture was added with <strong>[403-25-8]1-(difluoromethyl)-3-nitrobenzene</strong> (0.2 g, 1.15 mmol) and refluxed again for 1 hour. After addition of 20 ml ethyl acetate, impurities were removed using cellite and the organic layer was concentrated under vacuum. After column chromatography (ethylacetate/n-hexane, 1/15), the title compound (0.16 g, 50%) was obtained. 1H-NMR (600 MHz, CDCl3); δ 7.22 (t, J=7.8 Hz, 1H), 6.86 (d, J=7.8 Hz, 1H), 6.81 (s, 1H), 6.77-6.75 (m, 1H), 6.54 (t, J=56 Hz, 1H), 3.91 (brs, 2H)
	With palladium on activated charcoal; hydrogen; In ethanol;	A solution of Compound 2 (0.45 g, 2.9 mmol) and Pd/C(50 mg) in EtOH (5 mL) was stirred at rt under H2 atmosphere overnight. The Pd/C was removed by filtered. The filtrate was concentrated in vacuo to give the desired product, which was used for the next step directly
0.85 g	With iron; ammonium chloride; In ethanol; water; at 80℃; for 4h;	To a stirred solution of <strong>[403-25-8]1-(difluoromethyl)-3-nitrobenzene</strong> (0.9 g, 5 mmol) in ethanol:water (15:3 mL) was added iron powder (3.0 g, 52 mmol) and ammoniumchloride (0.3 g, 5 mmol) at ambient temperature. The reaction mixture was refluxed at 80 C. for 4 h. Completion of the reaction was confirmed by TLC. The reaction mixture was filtered through bed of celite and the filtrate was concentrated under vacuum to afford 3-(difluoromethyl) aniline (0.85 g) as brown gummy solid. MS (ESI) m/z 144 [M+1]+.

42 g

With iron; ammonium chloride; In methanol; water; at 70℃; for 12h;

To a solution of <strong>[403-25-8]1-(difluoromethyl)-3-nitrobenzene</strong> (55.0 g, 318 mmol) in a mixed solvent of methanol (500 ml) and water (200 ml) were added iron (53.2 g, 953 mmol) and ammonium chloride (85.0 g, 1.59 mol). The reaction mixture was stirred at 70 C for 12 h. The reaction mixture was cooled to rt and filtered. The filtrate was diluted with water and extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to give 3-(difluoromethyl)aniline (42.0 g) as yellow oil. 1H NMR (400 MHz, DMSO-d6): δ [ppm] = 7.11 (t, J = 8.0 Hz, 1H), 6.82 (t, J = 56.4 Hz, 1H), 6.72-6.62 (m, 3H), 5.35 (s, 2H).

References: [1]Patent: US2013/72482,2013,A1 .Location in patent: Paragraph 0229; 0232; 0233.
[2]Journal of Organic Chemistry USSR (English Translation),1970,vol. 6,p. 1436 - 1439.
Zhurnal Organicheskoi Khimii,1970,vol. 6,p. 1423 - 1426.
[3]Journal of Medicinal Chemistry,1995,vol. 38,p. 49 - 57.
[4]Patent: WO2013/96744,2013,A1 .Location in patent: Page/Page column 227.
[5]Patent: US2017/348316,2017,A1 .Location in patent: Paragraph 0423.
[6]Patent: EP3800188,2021,A1 .Location in patent: Paragraph 0207-0208.

4
[ 403-25-8 ]
2-(3-Difluoromethyl-phenylamino)-1,9-dihydro-purin-6-one [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 49 - 57.

5
[ 403-25-8 ]
[ 29848-59-7 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1970,vol. 6,p. 1436 - 1439.
Zhurnal Organicheskoi Khimii,1970,vol. 6,p. 1423 - 1426.

6
[ 403-25-8 ]
[ 26029-52-7 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1970,vol. 6,p. 1436 - 1439.
Zhurnal Organicheskoi Khimii,1970,vol. 6,p. 1423 - 1426.

7
[ 403-25-8 ]
[ 1261670-78-3 ]

Yield	Reaction Conditions	Operation in experiment
56.3%	With N-Bromosuccinimide; sulfuric acid; In water; at 20 - 60℃; for 1.5h;	Step 2: l-(Difluoromethyl)-3-nitrobenzene (866 mg, 5.00 mmol) was added to cold cone.H2SO4 and then NBS (890 mg, 5.00 mmol) was added. The mixture was warmed to room temperature for 30 minutes then 50-60 C for 1 h. The mixture was then poured in water and ice and extracted diethyl ether twice. The organic layer was washed with dilute aqueous NaHC03 and brine. Purification by chromatography on silica gel (0-15% ethyl acetate in hexanes) yielded l-bromo-3-(difluoromethyl)-5-nitrobenzene (710 mg, 2.82 mmol, 56.3%).

References: [1]Patent: WO2011/75515,2011,A1 .Location in patent: Page/Page column 262.

8
[ 403-25-8 ]
[ 1261512-35-9 ]

References: [1]Patent: WO2011/75515,2011,A1 .

9
[ 403-25-8 ]
[ 1312537-07-7 ]

References: [1]Patent: WO2011/75515,2011,A1 .

10
[ 403-25-8 ]
[ 1312537-08-8 ]

References: [1]Patent: WO2011/75515,2011,A1 .

11
[ 403-25-8 ]
[ 1312505-81-9 ]

References: [1]Patent: WO2011/75515,2011,A1 .

Yield	Reaction Conditions	Operation in experiment
60%	With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; hydroquinone; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 110℃; for 48h;Schlenk technique; Inert atmosphere;	General procedure: According to the general method A, the reaction was carried out with 0.3 mmol of arylboronic acid to give 4 (44 mg, yield: 72%).The product was purified by silica gel column chromatography.(n-hexane), a colorless, transparent oil. _: General Method A: Palladium catalyzed difluoromethylation of chlorodifluoroethane and arylboronic acid or ethylene arylborate. Add anhydrous K2CO3 (powder, 4.0 when) to a 25 mL Schlenk back bottle with argon anhydrous and anaerobic protection.Amount), hydroquinone (2.0 equivalents), Pd2 (dba) 3 (2.5 mol%), Xantphos (7.5 mol%) and ArB(OH) 2 (0.3 or 0.5 mmol) or Ar-Beg (0.3 or 0.5 mmol) Level reaction).Then add ClCF2H in 1,4 dioxane solution (2.0M,1.5 mL, 0.3 mmol grade reaction or 2.5 mL, 0.5 mmol grade reaction, 10 equivalents) and freshly distilled 1,4 dioxane (1.0 mL,0.3 mmol level reaction or 2.5 mL, 0.5 mmol level reaction).After the plug was plugged, the reaction mixture was heated to 110 C and stirred for 48 hours.After the completion of the reaction, the column chromatography was concentrated to give the object product.
1.5 g	With diethylamino-sulfur trifluoride; In dichloromethane; at 20℃; for 18h;Inert atmosphere;	General procedure: A solution of 2-fluoro-5-nitrobenzaldehyde (3.0 g, 17 mmol) in DCM (50 mL) was added DAST (3.42 g, 21 mmol) and stirred at RT for 18 h under nitrogen atmosphere. The reaction mass was quenched in ice-water and extracted with DCM. The organic layer was dried and concentrated to afford 2.5 g of desired product. 1H NMR (300 MHz, DMSO 6): δ 7.31 (s, 1H), 7.69 (t, / = 8.7 Hz, 1H), 8.46-8.50 (m, 2H).

13
difluoromethyl copper [ No CAS ]
[ 99-09-2 ]
[ 403-25-8 ]

References: [1]Organic Letters,2014,vol. 16,p. 5984 - 5987.

14
[ 586-36-7 ]
[ 86340-78-5 ]
[ 403-25-8 ]

References: [1]Chemical Communications,2016,vol. 52,p. 5965 - 5968.

15
[ 3718-22-7 ]
[ 403-25-8 ]

References: [1]Advanced Synthesis and Catalysis,2017,vol. 359,p. 2222 - 2228.

16
[ 75-45-6 ]
2-(3-Nitro-phenyl)-[1,3,2]dioxaborolane [ No CAS ]
[ 403-25-8 ]

Yield	Reaction Conditions	Operation in experiment
60%	With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; hydroquinone; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 110℃; for 48h;Inert atmosphere; Sealed tube;	General procedure: To a 25 ml sealed tube were added anhydrous K2CO3 (powder, 4.0 equiv.), hydroquinone (2.0 equiv.), Pd2(dba)3 (2.5 mol%), Xantphos (7.5 mol%) and ArB(OH)2 (0.3 or 0.5 mmol) or Ar-Beg (0.3 or 0.5 mmol) under argon. A solution of ClCF2H in 1,4-dioxane (2.0 M, 1.5 ml for 0.3 mmol scale or 2.5 ml for 0.5 mmol scale, 10 equiv.) and fresh distilled 1,4-dioxane (1.0 ml for 0.3 mmol scale or 2.5 ml for 0.5 mmol scale) were added subsequently. The sealed tube was screw capped and heated to 110 C (oil bath). After stirring for 48 h, the reaction was cooled to room temperature and fluorobenzene (1.0 equiv.) was added. The yield was determined by 19F NMR before working up. The reaction mixture was then diluted with ethyl acetate, filtered through a pad of Celite and concentrated. The residue was purified with silica gel chromatography to provide the desired product.

References: [1]Nature Chemistry,2017,vol. 9,p. 918 - 923.

17
[ 403-25-8 ]
[ 762-72-1 ]
1-(1-fluorobut-3-en-1-yl)-3-nitrobenzene [ No CAS ]

References: [1]Journal of the American Chemical Society,2019,vol. 141,p. 14120 - 14125.

18
[ 403-25-8 ]
2-(1-{6-chloro-1-[3-(difluoromethyl)phenyl]-1H-pyrazolo[3,4-d]-pyrimidin-4-yl}piperidin-4-yl)propan-2-ol [ No CAS ]