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[ CAS No. 450-83-9 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}

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Chemical Structure| 450-83-9

Chemical Structure| 450-83-9

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Quality Control of [ 450-83-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 450-83-9 ]

Product Details of [ 450-83-9 ]

CAS No. :	450-83-9	MDL No. :	MFCD00143318
Formula :	C₈H₇FO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PTKRQIRPNNIORO-UHFFFAOYSA-N
M.W :	154.13	Pubchem ID :	2774537
Synonyms :

Calculated chemistry of [ 450-83-9 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	38.28
TPSA :	26.3 Å²

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) :	-5.79 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.83
Log Po/w (XLOGP3) :	2.04
Log Po/w (WLOGP) :	2.07
Log Po/w (MLOGP) :	1.55
Log Po/w (SILICOS-IT) :	2.39
Consensus Log Po/w :	1.98

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.35
Solubility :	0.685 mg/ml ; 0.00444 mol/l
Class :	Soluble
Log S (Ali) :	-2.22
Solubility :	0.928 mg/ml ; 0.00602 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.74
Solubility :	0.282 mg/ml ; 0.00183 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.27

Safety of [ 450-83-9 ]

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 [ 450-83-9 ]

* 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 [ 450-83-9 ]
Downstream synthetic route of [ 450-83-9 ]

[ 450-83-9 ] Synthesis Path-Upstream 1~14

1
[ 2591-86-8 ]
[ 456-49-5 ]
[ 458-50-4 ]
[ 331-64-6 ]
[ 450-83-9 ]

Reference： [1] Archiv der Pharmazie, 1994, vol. 327, # 9, p. 547 - 561

2
[ 450-83-9 ]
[ 345-29-9 ]

Reference： [1] Journal of the Chemical Society, 1929, p. 1639

3
[ 2591-86-8 ]
[ 456-49-5 ]
[ 458-50-4 ]
[ 331-64-6 ]
[ 450-83-9 ]

Reference： [1] Archiv der Pharmazie, 1994, vol. 327, # 9, p. 547 - 561

4
[ 2591-86-8 ]
[ 456-49-5 ]
[ 331-64-6 ]
[ 450-88-4 ]
[ 450-83-9 ]

Reference： [1] Archiv der Pharmazie, 1994, vol. 327, # 9, p. 547 - 561

5
[ 2591-86-8 ]
[ 456-49-5 ]
[ 331-64-6 ]
[ 450-88-4 ]
[ 450-83-9 ]

Reference： [1] Archiv der Pharmazie, 1994, vol. 327, # 9, p. 547 - 561

6
[ 348-28-7 ]
[ 74-88-4 ]
[ 450-83-9 ]

Reference： [1] Organic Letters, 2007, vol. 9, # 23, p. 4893 - 4896

7
[ 50-00-0 ]
[ 372-20-3 ]
[ 77-78-1 ]
[ 450-83-9 ]
[ 146137-74-8 ]

Yield	Reaction Conditions	Operation in experiment
15.8 g	Stage #1: With magnesium chloride In acetonitrile for 0.0833333 h; Inert atmosphere; Molecular sieve Stage #2: for 0.5 h; Inert atmosphere; Molecular sieve	The m-fluorophenol (20g, 0.2πο1) was dissolved in acetonitrile (500mL, dried over molecular sieves), protected by argon and anhydrous magnesium chloride (102g, l.lmol) was added with stirring. 5min. Triethylamine (225 mL, 1.6 mol) was added and the mixture was exothermic. After stirring for 30 min, paraformaldehyde (63 g, purchased from aldrich company, the same below) was added and reacted at 50 ° C. for 3 h. Finished reaction. 1N aqueous hydrochloric acid was added to adjust the pH to 4, and the mixture was extracted with ethyl acetate (3 × 150 mL). The combined organic phases were dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure (water chestnut) to give the crude product as a dark red oil B-la and aldehyde by-product) 49.9g, set curing. The crude product was dissolved in tetrahydrofuran (100 mL) and potassium carbonate (81.2 g, 0.6 mol) and dimethyl sulfate (25.4 mL, 0.3 mol) were added and reacted at 40 ° C overnight ), TLC showed the raw material has disappeared. The potassium carbonate was filtered off and the solid was washed with ethyl acetate (3 × 100 mL). The organic phases were combined, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography (using a 15: 1 volume ratio of ro / Et0Ac as eluant) Intermediate B-2a (15.8 g) and by-product 2-fluoro-6-methoxybenzaldehyde (2.8 g) all in the form of a light yellow solid with a total yield of 68percent 0B-2a: Mp: ° C; 6h (300ΜΗζ; CDC13) 10.4 (1Η, s), 7.85 (1Η, dd, J = 8.4Hz, 6.9Ηζ), 6.75-6.67 (2H, m), 3.93 (d, J = 11.0Ηζ), 130.9 (d, J = 11.6Ηζ), 121.6 (d, J = , J = 2.7Hz), 108.1 (d, J = 22.1Ηζ), 99.7 (d, J = 25.7Ηζ), 56.0.2-Fluoro-6-methoxy- benzaldehyde: Μρ: 60-61 ° C ; 6H (300 MΗζ; CDC13) 10.3 (1H, s), 7.41 (1H, dd, J = 15.0Ηζ, 8.4Ηζ), 6.71-6.61 (2H, m), 3.85 (3H, s) CDC13) 187.4 (d, J = 3.4 Hz), 163.3 (dJc, F = 260.5 Hz), 162.2 (d, J = 5.4Ηζ), 136.2 (d, J = 12.0Ηζ), 114.0 ), 108.6 (d, J = 21.3 Hz), 107.3 (d, J = 3.5Ηζ), 56.3.

Reference： [1] European Journal of Organic Chemistry, 2016, vol. 2016, # 7, p. 1429 - 1438
[2] Patent: CN104557654, 2017, B, . Location in patent: Paragraph 0086-0088

8
[ 348-28-7 ]
[ 74-88-4 ]
[ 303043-87-0 ]
[ 450-83-9 ]

Reference： [1] Patent: US6376672, 2002, B1,

9
[ 372-20-3 ]
[ 450-83-9 ]

Reference： [1] Journal of the Chemical Society, 1929, p. 1639

10
[ 348-28-7 ]
[ 77-78-1 ]
[ 450-83-9 ]

Reference： [1] Journal of the Chemical Society, 1929, p. 1639

11
[ 2591-86-8 ]
[ 456-49-5 ]
[ 458-50-4 ]
[ 331-64-6 ]
[ 450-83-9 ]

Reference： [1] Archiv der Pharmazie, 1994, vol. 327, # 9, p. 547 - 561

12
[ 2591-86-8 ]
[ 456-49-5 ]
[ 331-64-6 ]
[ 450-88-4 ]
[ 450-83-9 ]

Reference： [1] Archiv der Pharmazie, 1994, vol. 327, # 9, p. 547 - 561

13
[ 450-83-9 ]
[ 395-82-4 ]

Reference： [1] Journal of the Chemical Society, 1929, p. 1639

14
[ 50-00-0 ]
[ 372-20-3 ]
[ 77-78-1 ]
[ 450-83-9 ]
[ 146137-74-8 ]

Yield	Reaction Conditions	Operation in experiment
15.8 g	Stage #1: With magnesium chloride In acetonitrile for 0.0833333 h; Inert atmosphere; Molecular sieve Stage #2: for 0.5 h; Inert atmosphere; Molecular sieve	The m-fluorophenol (20g, 0.2πο1) was dissolved in acetonitrile (500mL, dried over molecular sieves), protected by argon and anhydrous magnesium chloride (102g, l.lmol) was added with stirring. 5min. Triethylamine (225 mL, 1.6 mol) was added and the mixture was exothermic. After stirring for 30 min, paraformaldehyde (63 g, purchased from aldrich company, the same below) was added and reacted at 50 ° C. for 3 h. Finished reaction. 1N aqueous hydrochloric acid was added to adjust the pH to 4, and the mixture was extracted with ethyl acetate (3 × 150 mL). The combined organic phases were dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure (water chestnut) to give the crude product as a dark red oil B-la and aldehyde by-product) 49.9g, set curing. The crude product was dissolved in tetrahydrofuran (100 mL) and potassium carbonate (81.2 g, 0.6 mol) and dimethyl sulfate (25.4 mL, 0.3 mol) were added and reacted at 40 ° C overnight ), TLC showed the raw material has disappeared. The potassium carbonate was filtered off and the solid was washed with ethyl acetate (3 × 100 mL). The organic phases were combined, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography (using a 15: 1 volume ratio of ro / Et0Ac as eluant) Intermediate B-2a (15.8 g) and by-product 2-fluoro-6-methoxybenzaldehyde (2.8 g) all in the form of a light yellow solid with a total yield of 68percent 0B-2a: Mp: ° C; 6h (300ΜΗζ; CDC13) 10.4 (1Η, s), 7.85 (1Η, dd, J = 8.4Hz, 6.9Ηζ), 6.75-6.67 (2H, m), 3.93 (d, J = 11.0Ηζ), 130.9 (d, J = 11.6Ηζ), 121.6 (d, J = , J = 2.7Hz), 108.1 (d, J = 22.1Ηζ), 99.7 (d, J = 25.7Ηζ), 56.0.2-Fluoro-6-methoxy- benzaldehyde: Μρ: 60-61 ° C ; 6H (300 MΗζ; CDC13) 10.3 (1H, s), 7.41 (1H, dd, J = 15.0Ηζ, 8.4Ηζ), 6.71-6.61 (2H, m), 3.85 (3H, s) CDC13) 187.4 (d, J = 3.4 Hz), 163.3 (dJc, F = 260.5 Hz), 162.2 (d, J = 5.4Ηζ), 136.2 (d, J = 12.0Ηζ), 114.0 ), 108.6 (d, J = 21.3 Hz), 107.3 (d, J = 3.5Ηζ), 56.3.

Reference： [1] European Journal of Organic Chemistry, 2016, vol. 2016, # 7, p. 1429 - 1438
[2] Patent: CN104557654, 2017, B, . Location in patent: Paragraph 0086-0088

[ 450-83-9 ] Synthesis Path-Downstream 1~88

1
[ 2591-86-8 ]
[ 456-49-5 ]
[ 458-50-4 ]
[ 331-64-6 ]
[ 450-83-9 ]

Reference： [1]Archiv der Pharmazie,1994,vol. 327,p. 547 - 561

2
4-fluoro-thiobenzoic acid hydrazide hydrochloride [ No CAS ]
[ 450-83-9 ]
C₁₅H₁₂F₂N₂SO [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4255 - 4259

3
[ 348-28-7 ]
[ 74-88-4 ]
[ 450-83-9 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 4893 - 4896
[2]ChemMedChem,2019,vol. 14,p. 1173 - 1184

4
[ 450-83-9 ]
5-bromo-4-fluoro-2-methoxybenzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With N-Bromosuccinimide; In acetonitrile; at 70℃; for 12h;	The intermediate B-2a (21.5g, 0.14mol) was dissolved in acetonitrile (100mL), N-bromosuccinimide (27. Og, 0.17mo 1) was added and reacted at 70 C overnight 12h). TLC showed that the raw material had been reacted. 200mL of water was added and the mixture was stirred for 15min and extracted with ethyl acetate (3X50mL). The combined organic phases were dried over anhydrous magnesium sulfate and separated by column chromatography (15: 1 PE / EtOAc as eluent to give the bromo product (Intermediate B-3a) as a light yellow solid (30.7 g, yield 95%). B-3a: Mp: 80-82 C .; SH ) 10.2 (1H, s), 7.96 (1H, d, J = 8.1Etazeta), 6.72 (1H, d, J = 10.2Hz), 3.86 (3H, s)
94%	With N-Bromosuccinimide; In acetonitrile; at 70℃; for 18h;Inert atmosphere;	[0538] To a solution of <strong>[450-83-9]4-fluoro-2-methoxybenzaldehyde</strong> (5.0 g, 32.45 mmol) in acetonitrile (100 mL) N-bromosuccinimide (7.22 g, 40.56 mmol) was added and the reaction mixture was stirred at 70 oC under an atmosphere of nitrogen for 18 hours. It was partitioned with ethyl acetate (350 mL) and water (100 mL), the organic phase was washed with 1M aqueous hydrochloric acid (2x 150 mL) and brine (150 mL), dried over anhydrous sodium sulfate and concentrated. The resulting crude was purified by gradient silica gel flash chromatography (0-25% ethyl acetate in hexanes) to give 5-bromo-<strong>[450-83-9]4-fluoro-2-methoxybenzaldehyde</strong> (R-1.2.) (7.1 g, 94%). 1H-NMR (300 MHz, d6-DMSO): 10.28 (s, 1H), 7.98 (d, 1H), 6.86 (d, 1H), 3.90 (s, 3H). MS (EI) for C8H6BrFO2: 234 [M+H].
	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 60℃; for 3h;	To a mixture of <strong>[450-83-9]4-fluoro-2-methoxybenzaldehyde</strong> (12 g, 77.85 mmol, 1.00 equiv) in DMF (200 ml) was added NBS (69.4 g, 389.93 mmol, 5.01 equiv). The reaction mixture was stirred for 3 h at 60C. Water was added and the mixture was extracted with EtOAc thrice. The combined extracts were washed with brine and dried over Na2S04, then concentrated and purified by chromatography on silica gel (5: 1 PE/EA) to 5-bromo-4-fluoro-2- methoxybenzaldehyde as a colorless oil.

Reference： [1]European Journal of Organic Chemistry,2016,vol. 2016,p. 1429 - 1438
[2]Patent: CN104557654,2017,B .Location in patent: Paragraph 0086; 0087; 0089
[3]Patent: WO2017/223516,2017,A1 .Location in patent: Paragraph 0538
[4]Organic Letters,2007,vol. 9,p. 4893 - 4896
[5]Patent: WO2018/89449,2018,A1 .Location in patent: Page/Page column 113-115

5
[ 372-20-3 ]
[ 450-83-9 ]

Reference： [1]Journal of the Chemical Society,1929,p. 1639

6
[ 450-83-9 ]
[ 345-29-9 ]

Reference： [1]Journal of the Chemical Society,1929,p. 1639

7
[ 348-28-7 ]
[ 74-88-4 ]
[ 303043-87-0 ]
[ 450-83-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetone;	(a) 1-(3-Chloro-propoxymethyl)-4-fluoro-2-methoxy-benzene To a solution of 1.3 g (9.3 mmol) of 4-fluoro-2-hydroxy-benzaldehyde, obtained following the method described by R. Alfred et al. in J. Chem. Soc., Perkin Trans. (1994), 1823, in 20 ml of acetone were added 0.87 ml (13.4 mmol) of methyliodide and 1.9 g (13.4 mmol) of powdered potassium carbonate. The dispersion was stirred at 45 C. for 2 hours. Subsequently, the reaction mixture was evaporated, the residue extracted with dichloromethane and water, the organic phase separated and concentrated under reduced pressure. There was obtained 1.1 g (77% of theory) of 4-fluoro-2-methoxy-benzaldehyde as a yellow solid; M: 154 (M)+.

Reference： [1]Patent: US6376672,2002,B1

8
[ 450-83-9 ]
[ 157068-03-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium borohydrid; potassium hydrogencarbonate; In methanol; water;	(b) An ice-cold solution of 5.6 g of <strong>[450-83-9]4-fluoro-2-methoxy-benzaldehyde</strong> in 75 ml of methanol was treated portionwise (5 portions within 50 minutes) with 1.51 g (40 mmol) of sodium borohydride and the reaction mixture was stirred for another 1 hour at room temperature. A dispersion of 7 g of potassium hydrogencarbonate in 20 ml of water was added and the mixture stirred for 30 minutes at room temperature. Thereupon, most of the methanol was evaporated under reduced pressure and the residue extracted with dichloromethane. The organic phase was separated, dried and concentrated under reduced pressure to yield 5.15 g (91% of theory) of (4-fluoro-2-methoxy-phenyl)-methanol as a white solid; MS: 156 (M)+.

Reference： [1]Patent: US6376672,2002,B1

9
[ 450-83-9 ]
[ 204707-29-9 ]

Yield	Reaction Conditions	Operation in experiment
95%		3 alpha-(4-fluoro-2-methoxyphenyl)-N-t-butylnitrone The title compound (405.7 mg; 95%) was prepared by the same method as that described in Example 1, using <strong>[450-83-9]4-fluoro-2-methoxybenzaldehyde</strong> (293.3 mg, 1.90 mmol). 1H-NMR(CDCl3) 9.44 (dd, 1H, J=8.9, 7.3 Hz), 7.95 (s, 1H), 6.71 (td, 1H, J=8.9, 2.3 Hz), 6.60 (dd, 1H, J=10.8, 2.3 Hz), 3.87 (m, 3H), 1.54 (s, 9H)

Reference： [1]Patent: US6194461,2001,B1

10
[ 1036942-53-6 ]
[ 450-83-9 ]
[ 1202692-33-8 ]

Yield	Reaction Conditions	Operation in experiment
62%		Example 4 (Compound No. 8 of table 2) (+/-)-10-[(4-Fluoro-2-methoxy-phenyl)-hydroxy-methyl]-2-pyrimidin-4-yl-7,8,9,10-tetrahydro-6H-pyrimido[1,2-a]azepin-4-one; To a solution of 0.500g (2.06 mmol) of 2-pyrimidin-4-yl-7,8,9,10-tetrahydro-6H-pyrimido[1,2-a]azepin-4-one (step 4.1) in dry tetrahydrofuran (20 mL) under argon at - 40 C was added 2.48 mL (2.48 mmol) of lithium bis(trimethylsilyl)amide (1 M in tetrahydrofuran). The solution was stirred at - 40C for 10 min and 0.636g of <strong>[450-83-9]4-fluoro-2-methoxy-benzaldehyde</strong> (4.13 mmol) diluted in 5 ml of dry tetrahydrofuran was added. The reaction was allowed to increase to room temperature for 2h. The mixture was quenched with the addition of a saturated solution of ammonium chloride and extracted with dichloromethane. The organic phase was dried over sodium sulfate and concentrated. The residue was purified by flash chromatography (dichloromethane with 2% of methanol and 0.2 % of ammonia) to afford 0.505g of a white solid (62%). Mp : 235-237C. RMN 1H (DMSO-d6; 400 MHz) delta (ppm) : 9.30 (s, 1H), 9.05 (d, 1H), 8.15 (d, 1H), 7.52 (m, 1H), 7.18 (s, 1H), 6.88 (d, 1H), 6.72 (m, 1H), 5.58 (m, 1H), 5.28 (m, 1H), 4.88 (m, 1H), 3.92 (m, 1H), 3.85 (s, 3H), 3.60 (m, 1H), 2.12 (m, 1H), 1.92 (m, 2H), 1.58 (m, 2H), 1.42 (m, 1H).

Reference： [1]Patent: EP2138494,2009,A1 .Location in patent: Page/Page column 12-13

11
[ 1189777-88-5 ]
[ 450-83-9 ]
C₂₈H₃₇FN₄O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5063 - 5066

12
[ 870-64-4 ]
[ 450-83-9 ]
[ 213682-44-1 ]
[ 1015077-84-5 ]

Yield	Reaction Conditions	Operation in experiment
36%	In isopropyl alcohol;Reflux;	150 mg (0.973 mmol) of <strong>[450-83-9]4-fluoro-2-methoxybenzaldehyde</strong>, 151 mg (0.973 mmol) of the compound from example 4A and 80 mg (0.973 mmol) of 3-aminocrotononitrile are dissolved in 4 ml of isopropanol and stirred at the reflux temperature overnight. After cooling to room temperature, the volatile components are removed in a rotary evaporator, and the crude product is purified by flash chromatography (silica gel, mobile phase: cyclohexane/ethyl acetate 1:1). After removal of the solvent, the product is obtained by crystallization from diisopropyl ether. Drying under high vacuum results in 123 mg (36% of theory) of the title compound.LC-MS (Method 1): Rt=2.43 min; (Elpos): m/z=356 [M+H]+ 1H-NMR (300 MHz, DMSO-d6): delta [ppm]=1.97 (s, 3H), 2.26 (s, 3H), 2.39 (s, 3H), 3.83 (s, 3H), 5.04 (s, 1H), 6.68 (dt, 1H), 6.87 (dd, 1H), 6.95 (s, 1H), 7.07 (dd, 1H), 9.00 (s, 1H).

Reference： [1]Patent: US2010/240620,2010,A1 .Location in patent: Page/Page column 23-24

13
[ 6294-93-5 ]
[ 450-83-9 ]
[ 1354963-00-0 ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium carbonate; In dimethyl sulfoxide; at 80℃; for 18h;	A solution of 4-chloro-3-(trifluoromethyl)phenol (0.383 g, 1.95 mmol) and <strong>[450-83-9]4-fluoro-2-methoxybenzaldehyde</strong> (0.300 g, 1.95 mmol) in DMSO (5 mL) was prepared. Potassium carbonate (0.538 g, 3.90 mmol) was added and the reaction mixture was heated at 80-° C. for 18 hours. The reaction was cooled to room temperature, diluted with ethyl acetate (30 mL) and washed with water (3.x.60 mL). The organic layer was dried over magnessium sulfate and the filtrate was concentrated in vacuo to give the title product as a cream solid (0.479 g, 74percent).LCMS Rt=3.62 minutes MS m/z 331 [MH]+ 1HNMR (400 MHz, CDCl3): delta 3.85 (s, 3H), 6.45 (d, 1H), 6.55 (s, 1H), 7.10 (d, 1H), 7.35 (s, 1H), 7.45 (d, 1H), 7.80 (d, 1H), 10.30 (s, 1H).

Reference： [1]Patent: US2012/10207,2012,A1 .Location in patent: Page/Page column 57-58

14
[ 6294-93-5 ]
[ 450-83-9 ]
[ 1354957-04-2 ]

Reference： [1]Patent: US2012/10207,2012,A1

15
[ 5382-16-1 ]
[ 450-83-9 ]
[ 1374859-10-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

16
[ 5382-16-1 ]
[ 450-83-9 ]
[ 1374858-29-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

17
[ 39888-51-2 ]
[ 450-83-9 ]
[ 1374859-11-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

18
[ 39888-51-2 ]
[ 450-83-9 ]
[ 1374858-30-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

19
[ 5625-67-2 ]
[ 450-83-9 ]
[ 1374859-15-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

20
[ 1126-09-6 ]
[ 450-83-9 ]
[ 1374859-12-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

21
[ 21987-29-1 ]
[ 450-83-9 ]
[ 1374859-14-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

22
[ 21987-29-1 ]
[ 450-83-9 ]
[ 1374858-37-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

23
[ 45347-82-8 ]
[ 450-83-9 ]
[ 1374859-09-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

24
[ 450-83-9 ]
[ 1374858-31-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

25
[ 450-83-9 ]
[ 1374858-33-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

26
[ 450-83-9 ]
[ 1374858-96-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

27
[ 450-83-9 ]
[ 1374858-34-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

28
[ 450-83-9 ]
[ 1374858-98-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

29
[ 450-83-9 ]
[ 1374858-99-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

30
[ 450-83-9 ]
[ 1374858-35-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

31
[ 450-83-9 ]
[ 1374858-58-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

32
[ 450-83-9 ]
C₂₈H₃₇N₅O₅ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

33
[ 450-83-9 ]
[ 1374858-43-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

34
[ 450-83-9 ]
[ 1374858-24-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

35
[ 450-83-9 ]
[ 1374858-25-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

36
[ 450-83-9 ]
[ 1374858-26-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

37
[ 450-83-9 ]
[ 1374858-27-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

38
[ 450-83-9 ]
[ 1374858-28-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

39
[ 450-83-9 ]
[ 122536-76-9 ]
[ 1374859-07-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

40
[ 450-83-9 ]
[ 122536-76-9 ]
[ 1374858-97-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

41
[ 450-83-9 ]
[ 73874-95-0 ]
[ 1374859-08-1 ]

Yield	Reaction Conditions	Operation in experiment
64%	With potassium carbonate; In dimethyl sulfoxide; at 80℃; for 24h;	To a solution of <strong>[450-83-9]4-fluoro-2-methoxybenzaldehyde</strong> (292 mg, 1.89 mmol) in DMSO (3 mL) were added potassium carbonate (392 mg, 2.84 mmol) and tert-butyl piperidin-4-yl carbamate (378 mg, 1.89 mmol). The reaction mass was stirred at 80 C for 24 h. The reaction mass was quenched with water and was extracted with ethyl acetate. The organic layer was dried, filtered and concentrated to afford the title product (410 mg, 64%). 1H NMR (300 MHz, DMSO-d6): delta 10.02 (s, 1H), 7.51 (d, J = 8.7 Hz, 1H), 6.86 (br s, 1H), 6.57 (d, J = 8.4 Hz, 1H), 6.44 (s, 1H), 3.97-3.92 (m, 2H), 3.87 (s, 3H), 3.51 (br s, 1H), 3.32 (s, 2H), 3.03-2.95 (t. J =11.7 Hz, 2H), 1.81-1.77 (m, 2H), 1.38 (s, 9H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 6286 - 6291
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

42
[ 450-83-9 ]
[ 112275-50-0 ]
[ 1374858-57-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium carbonate; In dimethyl sulfoxide; at 80℃; for 24h;	To a solution of <strong>[450-83-9]4-fluoro-2-methoxybenzaldehyde</strong> (310 mg, 2.01 mmol) in DMSO (4 mL) were added potassium carbonate (417 mg, 3.02 mmol) and tert-butyl 1,4-diazepane-1-carboxylate (403 mg, 2.01 mmol). The reaction mass was stirred at 80 C for 24 h. The reaction mass was quenched with water and was extracted with ethyl acetate. The organic layer was dried, filtered and concentrated to afford the title product (470 mg, 70%). 1H NMR (300 MHz, CDCl3): d 10.14 (s, 1H), 7.72 (d, J = 9.0 Hz, 1H), 6.34 (d, J = 8.7 Hz, 1H), 6.12 (s, 1H), 3.89 (s, 3H), 3.62 (br s, 6H), 3.36 (br s, 1H), 3.26 (br s, 1H), 2.00-1.98 (m, 2H), 1.43 (s, 9H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 6286 - 6291
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

43
[ 450-83-9 ]
[ 57260-71-6 ]
[ 1374859-06-9 ]

Yield	Reaction Conditions	Operation in experiment
58%	With potassium carbonate; In dimethyl sulfoxide; at 80℃; for 12h;	To a solution of <strong>[450-83-9]4-fluoro-2-methoxybenzaldehyde</strong> (0.100 g, 0.65 mmol) in DMSO (2 mL), were added K2CO3 (0.391 g, 2.83 mmol) and tert-butyl piperazine-1-carboxylate (0.386 g, 2.08 mmol). The reaction mass was stirred at 80C for 12 h before it was quenched with water and was extracted with EtOAc. The organic layer was dried and concentrated to afford 0.120 g (Yield: 58%) of the title product.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

44
[ 450-83-9 ]
[ 57260-71-6 ]
[ 1374858-95-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3223 - 3228

45
[ 450-83-9 ]
[ 1404065-37-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 6286 - 6291

46
[ 450-83-9 ]
[ 1404065-58-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 6286 - 6291

47
[ 450-83-9 ]
[ 1404065-55-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 6286 - 6291

48
[ 450-83-9 ]
[ 1404065-57-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 6286 - 6291

49
[ 450-83-9 ]
[ 1404065-69-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 6286 - 6291

50
[ 450-83-9 ]
[ 1404065-70-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 6286 - 6291

51
[ 450-83-9 ]
[ 1404065-71-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 6286 - 6291

52
[ 450-83-9 ]
[ 1404065-72-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 6286 - 6291

53
[ 450-83-9 ]
[ 1404065-73-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 6286 - 6291

54
[ 450-83-9 ]
[ 1404065-65-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 6286 - 6291

55
[ 450-83-9 ]
[ 1404065-66-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 6286 - 6291

56
[ 450-83-9 ]
[ 1404065-68-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 6286 - 6291

57
[ 450-83-9 ]
[ 1404065-67-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 6286 - 6291

58
[ 450-83-9 ]
[ 1404065-64-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 6286 - 6291

59
[ 450-83-9 ]
[ 1409950-64-6 ]

Reference： [1]Patent: US2013/115190,2013,A1
[2]Patent: US2015/284409,2015,A1
[3]Patent: US9527885,2016,B2

60
[ 450-83-9 ]
[ 913699-84-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	With malonic acid; In pyridine;	Step 1 A solution of <strong>[450-83-9]4-fluoro-2-methoxybenzaldehyde</strong> (1.0 g, 6.49 mmol) and malonic acid (1.350 g, 12.98 mmol) in pyridine (10 mL) was refluxed for 16 h. After concentration the residue was taken into water. The solid was filtered, washed with water, then dried to give (E)-3-(4-fluoro-2-methoxyphenyl)acrylic acid (1.22 g, 96% yield). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.03 (d, J=16.1 Hz, 1H), 7.53 (dd, J=8.5, 6.8 Hz, 1H), 6.75-6.65 (m, 2H), 6.52 (d, J=16.1 Hz, 1H), 3.92 (s, 3H).

Reference： [1]Patent: US2013/115190,2013,A1 .Location in patent: Page/Page column

61
[ 450-83-9 ]
[ 1409950-65-7 ]

Reference： [1]Patent: US2013/115190,2013,A1
[2]Patent: US2015/284409,2015,A1
[3]Patent: US9527885,2016,B2

62
[ 450-83-9 ]
[ 1409950-66-8 ]

Reference： [1]Patent: US2013/115190,2013,A1
[2]Patent: US2015/284409,2015,A1
[3]Patent: US9527885,2016,B2

63
[ 450-83-9 ]
[ 1409950-67-9 ]

Reference： [1]Patent: US2013/115190,2013,A1
[2]Patent: US2015/284409,2015,A1
[3]Patent: US9527885,2016,B2

64
[ 450-83-9 ]
[ 68498-54-4 ]
[ 16617-46-2 ]
[ 1578067-10-3 ]

Yield	Reaction Conditions	Operation in experiment
33%	With perchloric acid; In methanol; at 20℃; for 15h;Inert atmosphere;	To a clear light yellow solution of 5-amino-1H-pyrazole-4- carbonitrile (169 mg, 1.56 mmol) and <strong>[450-83-9]4-fluoro-2-methoxybenzaldehyde</strong> (240 mg, 1.56 mmol) in methanol (3 mL) was added cyclopentane isonitrile (150 mg, 174 jiL, 1.56 mmol) followed by perchloric acid (31.3 mg, 28.0 jiL, 0.312 mmol) at RT under nitrogen atmosphere. The resulting light brown suspension was stirred for 15 h and during this period (within 1 minute) lot of solidswere formed. The solids were collected by filtration and washed with methanol. After air drying,175 mg (33% yield) of 3 -(cyclopentylamino)-2-(4-fluoro-2-methoxyphenyl)- 1H-imidazo [1,2- b]pyrazole-7-carbonitrile was isolated as an off-white solid. LC/MS calcd. for C18H18FN50 (m/e) 339.37, obsd. 340.0 (M+H, ES+).

Reference： [1]Patent: WO2014/37303,2014,A1 .Location in patent: Page/Page column 13; 14

65
[ 450-83-9 ]
[ 68498-54-4 ]
[ 1578066-60-0 ]

Reference： [1]Patent: WO2014/37303,2014,A1

66
[ 2033-24-1 ]
[ 450-83-9 ]
[ 1261573-10-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With formic acid; triethylamine; at 0 - 100℃; for 2h;	To a solution of formic acid (3.7 mL) was added triethylamine (5.4 mL) at 0 C. followed by compound 33-5 (1.85 g. 12 mmol) and 2.2-dimethyl-l.3-dioane-4.6-dione (1.73 g. 12 mmol). At the end of the addition, the mixture was stirred at 100 C for 2.0 hrs. A ter the reaction was completed.20 mL of ice water was added to the mixture, and the resulting mixture was adjusted to pH 1 with hydrochloric acid (2 M) and extracted with EtOAc (25 mL x 3). The combined organic layers were dried over anhydrous and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 3/1) to give the title compound as a white solid (2.02 g.85%). The compound was characterized by the following spectroscopic data: MS (ESI, pos.ion) mlz: 199.5 [M+H] '; and NMR (400 MHz. CDCh) delta (ppm) : 9.60 (brs.1H ).7.13-7.09 (m.1 H), 6.82-6.81.6.79-6.77 (m. m, 1H). 6.76-6.71 (m.1H).3.79 (d, 3H).2.90-2.85 (m.211).2.62.2.60.2.58 (d. d. d.2H).

Reference： [1]Patent: WO2014/82379,2014,A1 .Location in patent: Page/Page column 225; 226; 227

67
[ 450-83-9 ]
[ 1092347-59-5 ]

Reference： [1]Patent: WO2014/82379,2014,A1

68
[ 450-83-9 ]
[ 1612855-13-6 ]

Reference： [1]Patent: WO2014/82379,2014,A1

69
[ 450-83-9 ]
[ 1612855-14-7 ]

Reference： [1]Patent: WO2014/82379,2014,A1

70
[ 450-83-9 ]
[ 1612855-15-8 ]

Reference： [1]Patent: WO2014/82379,2014,A1

71
[ 450-83-9 ]
[ 1612855-16-9 ]

Reference： [1]Patent: WO2014/82379,2014,A1

72
[ 450-83-9 ]
[ 1612855-17-0 ]

Reference： [1]Patent: WO2014/82379,2014,A1

73
[ 450-83-9 ]
[ 1612855-18-1 ]

Reference： [1]Patent: WO2014/82379,2014,A1

74
[ 450-83-9 ]
[ 1612855-19-2 ]

Reference： [1]Patent: WO2014/82379,2014,A1

75
[ 450-83-9 ]
[ 1612855-20-5 ]

Reference： [1]Patent: WO2014/82379,2014,A1

76
(1S,3S,4R)-4-[(3aS,4R,5S,7aS)-4-(aminomethyl)-7a-methyl-1-methylidene-octahydro-1H-inden-5-yl]-3-(hydroxymethyl)-4-methylcyclohexan-1-ol [ No CAS ]
[ 450-83-9 ]
(1S,3S,4R)-4-((3aS,4R,5S,7aS)-4-((4-fluoro-2-methoxybenzylamino)methyl )-7a-methyl-1-methyleneoctahydro-1H-inden-5-yl)-3-(hydroxymethyl)-4-methylcyclohexanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%		A solution of (1 S,35,4R)-4-((3a5,4R,55,7a5)-4-(arninornethyl)-7a-rnethyl-1 - rnethyleneoctahydro-1 H-inden-5-yl)-3-(hyd roxyrnethyl)-4-rnethylcyclohexanol (Cornpound No. 22, 61 rng, 0.19 rnrnol) and 4-fluoro-2-rnethoxybenzaldehyde (35 rng, 0.23 rnrnol) in MeOH (3.8 rnL) was heated to reflux under argon for 0.5 h then allowedto cool to roorn ternperature. NaBH4 (14 rng, 0.37 rnrnol) was added and stirred at roorn ternperature for 5 h. The rnixture was concentrated, and the residue was dissolved in 1:9 MeOHCH2CI2 (15 rnL) then washed with 1 N NaOH(aq) (10 rnL). The aqueous layer was extracted with CH2CI2 (2X10 rnL), and the cornbined organic layers were dried (Mg504) and concentrated. The residue was purified by chrornatographyon silica gel (10:90 MeOHCH2CI2) to give (1S,35,4R)-4-((3a5,4R,55,7a5)-4-((4-fluoro-2-rnethoxybenzylarnino)rnethyl)-7a-rnethyl-1 -rnethyleneoctahyd ro-1 H-inden-5-yl)-3- (hydroxyrnethyl)-4-rnethylcyclohexanol (Cornpound No. 78, 80 rng, 92%) as a colourless foarn. 1H NMR(CD3OD): 67.23 (rn, 1H), 6.80 (dd, J= 11,2.1 Hz, 1H), 6.65 (rn, 1H), 4.63 (s, 2H), 3.85 (s, 3H), 3.73 (rn, 3H), 3.41 (rn, 1H), 3.12 (rn, 1H), 2.87 (rn,1H), 2.64 (rn, 1H), 2.49 (rn, 1H), 2.10-2.31 (rn, 2H), 1.18-1.83 (rn, 15H), 0.96 (s, 3H),0.79 (s, 3H). ES-MS m/z 460 ([M-f-1]).

Reference： [1]Patent: WO2014/143561,2014,A1 .Location in patent: Page/Page column 128

77
[ 450-83-9 ]
5-fluoro-[1,1'-biphenyl]-2-carbaldehyde [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 14367 - 14372

78
[ 450-83-9 ]
[ 75-64-9 ]
N-(4-fluoro-2-methoxybenzylidene)tert-butylamine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 14367 - 14372

79
[ 450-83-9 ]
[ 1779-49-3 ]
4-fluoro-2-methoxy-1-vinylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
321 mg		Synthesis of 4-fluoro-2-methoxy-1-vinylbenzene. A suspension of 12.73 g of methyl triphenylphosphonium bromide in 100 mL of dry THF was treated at room temperature with 15.6 mL of n-BuLl (2.5 M solution in n-hexane). The resulting orange solution was stirred for 4 hours. Then, a solution of 5.00 g of <strong>[450-83-9]4-fluoro-o-anisaldehyde</strong> in 25 mL of dry THF was added dropwise. Upon addition a white precipitate formed. The suspension was stirred for 1 hour and concentrated in vacuo to give aviscous orange oil that was purified by passing through a short column of Si02 (heptane) then vacuum distillation to yield 321 mg of 4-fluoro-2-methoxy-1-vinylbenzene as a colorless liquid. 1H-NMR (300MHz, CDCI3): 63.76 (s, 3H), 5.15 (dd, Ji=11.1 Hz, J2=1.4 Hz, IH), 5.69 (dd, J1=17.6 Hz, J2=1.4 Hz,1H), 6.48-6.60 (m, 2H), 6.81-6.94 (m, IH), 7.29-7.37 (m, 1H). GC-MS: 97.5% MS (El): 152.

Reference： [1]Patent: WO2015/155593,2015,A1 .Location in patent: Page/Page column 48; 49

80
[ 50-00-0 ]
[ 372-20-3 ]
[ 77-78-1 ]
[ 450-83-9 ]
[ 146137-74-8 ]

Yield	Reaction Conditions	Operation in experiment
15.8 g; 2.8 g		The m-fluorophenol (20g, 0.2piomicron1) was dissolved in acetonitrile (500mL, dried over molecular sieves), protected by argon and anhydrous magnesium chloride (102g, l.lmol) was added with stirring. 5min. Triethylamine (225 mL, 1.6 mol) was added and the mixture was exothermic. After stirring for 30 min, paraformaldehyde (63 g, purchased from aldrich company, the same below) was added and reacted at 50 C. for 3 h. Finished reaction. 1N aqueous hydrochloric acid was added to adjust the pH to 4, and the mixture was extracted with ethyl acetate (3 × 150 mL). The combined organic phases were dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure (water chestnut) to give the crude product as a dark red oil B-la and aldehyde by-product) 49.9g, set curing. The crude product was dissolved in tetrahydrofuran (100 mL) and potassium carbonate (81.2 g, 0.6 mol) and dimethyl sulfate (25.4 mL, 0.3 mol) were added and reacted at 40 C overnight ), TLC showed the raw material has disappeared. The potassium carbonate was filtered off and the solid was washed with ethyl acetate (3 × 100 mL). The organic phases were combined, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography (using a 15: 1 volume ratio of ro / Et0Ac as eluant) Intermediate B-2a (15.8 g) and by-product 2-fluoro-6-methoxybenzaldehyde (2.8 g) all in the form of a light yellow solid with a total yield of 68% 0B-2a: Mp: C; 6h (300MuEtazeta; CDC13) 10.4 (1Eta, s), 7.85 (1Eta, dd, J = 8.4Hz, 6.9Etazeta), 6.75-6.67 (2H, m), 3.93 (d, J = 11.0Etazeta), 130.9 (d, J = 11.6Etazeta), 121.6 (d, J = , J = 2.7Hz), 108.1 (d, J = 22.1Etazeta), 99.7 (d, J = 25.7Etazeta), 56.0.2-Fluoro-6-methoxy- benzaldehyde: Murho: 60-61 C ; 6H (300 MEtazeta; CDC13) 10.3 (1H, s), 7.41 (1H, dd, J = 15.0Etazeta, 8.4Etazeta), 6.71-6.61 (2H, m), 3.85 (3H, s) CDC13) 187.4 (d, J = 3.4 Hz), 163.3 (dJc, F = 260.5 Hz), 162.2 (d, J = 5.4Etazeta), 136.2 (d, J = 12.0Etazeta), 114.0 ), 108.6 (d, J = 21.3 Hz), 107.3 (d, J = 3.5Etazeta), 56.3.

Reference： [1]European Journal of Organic Chemistry,2016,vol. 2016,p. 1429 - 1438
[2]Patent: CN104557654,2017,B .Location in patent: Paragraph 0086-0088

81
[ 450-83-9 ]
1-(benzyloxy)-5-bromo-4-fluoro-2-methoxybenzene [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2016,vol. 2016,p. 1429 - 1438
[2]Patent: CN104557654,2017,B

82
[ 450-83-9 ]
C₄₀H₄₀FNO₆ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2016,vol. 2016,p. 1429 - 1438

83
[ 450-83-9 ]
C₁₂H₁₆FNO₅ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2016,vol. 2016,p. 1429 - 1438

84
[ 450-83-9 ]
C₈H₆BrFO₃ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2016,vol. 2016,p. 1429 - 1438

85
[ 450-83-9 ]
[ 1364606-67-6 ]

Reference： [1]European Journal of Organic Chemistry,2016,vol. 2016,p. 1429 - 1438
[2]Patent: CN104557654,2017,B

86
[ 141-82-2 ]
[ 450-83-9 ]
[ 913699-84-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	With pyridine; for 16h;Reflux;	A solution of <strong>[450-83-9]4-fluoro-2-methoxybenzaldehyde</strong> (1.0 g, 6.49 mmol) and malonic acid (1.350 g, 12.98 mmol) in pyridine (10 mL) was refluxed for 16 h. After concentration the residue was taken into water. The solid was filtered, washed with water, then dried to give (E)-3-(4-fluoro-2-methoxyphenyl)acrylic acid (1.22 g, 96% yield). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.03 (d, J=16.1 Hz, 1H), 7.53 (dd, J=8.5, 6.8 Hz, 1H), 6.75-6.65 (m, 2H), 6.52 (d, J=16.1 Hz, 1H), 3.92 (s, 3H).
96%	With pyridine; for 16h;Reflux;	A solution of <strong>[450-83-9]4-fluoro-2-methoxybenzaldehyde</strong> (1.0 g, 6.49 mmol) and malonic acid (1.350 g, 12.98 mmol) in pyridine (10 mL) was refluxed for 16 h. After concentration the residue was taken into water. The solid was filtered, washed with water, then dried to give (E)-3-(4-fluoro-2-methoxyphenyl)acrylic acid (1.22 g, 96% yield). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.03 (d, J=16.1 Hz, 1H), 7.53 (dd, J=8.5, 6.8 Hz, 1H), 6.75-6.65 (m, 2H), 6.52 (d, J=16.1 Hz, 1H), 3.92 (s, 3H)

Reference： [1]Patent: US2015/284409,2015,A1 .Location in patent: Paragraph 0291; 0292
[2]Patent: US9527885,2016,B2 .Location in patent: Page/Page column 57

87
2-(furan-2-yl)cyclopropanecarbohydrazide [ No CAS ]
[ 450-83-9 ]
(E)-N'-(4-fluoro-2-methoxybenzylidene)-2-(furan-2-yl)cyclopropanecarbohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With zinc(II) oxide; In ethanol; at 20℃;Green chemistry;	General procedure: A mixture of appropriate aldehyde (10 mmol) from the list a-t, compound 4 (10 mmol), ZnO Nano particles (2 mmol) and ethanol (25 mL) was stirred at rt for 30 min to 1 h. After completion of reaction (monitored by TLC), the reaction mixture was filtered through a nanofiltration membrane (Make: Synder, Model: NFS 100-250Da). The filtrate was evaporated under reduced pressure and dried to obtain crude product 5a-t which was further purified by recrystallization in ethanol to afford pure compounds.

Reference： [1]Journal of Chemical Sciences,2016,vol. 128,p. 929 - 939

88
[ 450-83-9 ]
4-formyl-3-methoxy-N,N,N-trimethylbenzenaminium iodide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 5353 - 5356

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Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Ghs Hazard Statements

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere