[ CAS No. 13246-46-3 ]

Name: 13246-46-3|2,4-Dibenzyloxy benzaldehyde|96%
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Quality Control of [ 13246-46-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 13246-46-3 ]

SDS Specification

Alternatived Products of [ 13246-46-3 ]

Product Details of [ 13246-46-3 ]

CAS No. :	13246-46-3	MDL No. :	MFCD00022024
Formula :	C₂₁H₁₈O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DMYYTMVFUMDOGC-UHFFFAOYSA-N
M.W :	318.37 g/mol	Pubchem ID :	1809080
Synonyms :

Calculated chemistry of [ 13246-46-3 ]

Physicochemical Properties

Num. heavy atoms :	24
Num. arom. heavy atoms :	18
Fraction Csp3 :	0.1
Num. rotatable bonds :	7
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	93.79
TPSA :	35.53 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.18 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.35
Log Po/w (XLOGP3) :	4.31
Log Po/w (WLOGP) :	4.35
Log Po/w (MLOGP) :	3.43
Log Po/w (SILICOS-IT) :	5.1
Consensus Log Po/w :	4.11

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.62
Solubility :	0.0076 mg/ml ; 0.0000239 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.77
Solubility :	0.00541 mg/ml ; 0.000017 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-7.65
Solubility :	0.00000713 mg/ml ; 0.0000000224 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.49

Safety of [ 13246-46-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338-P304+P340-P405	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 13246-46-3 ]

* 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 [ 13246-46-3 ]
Downstream synthetic route of [ 13246-46-3 ]

[ 13246-46-3 ] Synthesis Path-Upstream 1~2

1
[ 13246-46-3 ]
[ 52085-14-0 ]

Yield	Reaction Conditions	Operation in experiment
72%	With zinc(II) chloride In 1,2-dichloro-ethane at 80℃;	General procedure: A clean, oven dried 2 dram screw cap vial was charged with ZnCl2 (1.05 equiv) and DCE (1 mL). A solution of ortho-protected phenol (0.15 mmol, 1 equiv) in DCE (0.5 mL) was added via syringe and the reaction stirred at the indicated temperature until starting material was consumed as determined by TLC analysis. The reaction was then diluted with saturated aqueous NH4Cl (20 mL), the layers were separated,and the aqueous phase extracted with CH2Cl2 (3 x 10 mL). The combined organic fractions were washed with saturated aqueous NaCl (20 mL), dried (MgSO4), and concentrated under reduced pressure. The resulting crude material was purified by flash chromatography eluting with hexanes/EtOAc to give the ortho-deprotected phenol 33 mg (72percent) as white solid

Reference： [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1986, vol. 40, # 5, p. 400 - 401
[2] Chemical and Pharmaceutical Bulletin, 1998, vol. 46, # 2, p. 222 - 230
[3] Tetrahedron Letters, 2012, vol. 53, # 40, p. 5376 - 5379

2
[ 100-44-7 ]
[ 95-01-2 ]
[ 13246-46-3 ]
[ 52085-14-0 ]

Reference： [1] Synthetic Communications, 1996, vol. 26, # 3, p. 593 - 601

[ 13246-46-3 ] Synthesis Path-Downstream 1~41

1
[ 100-39-0 ]
[ 95-01-2 ]
[ 13246-46-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With caesium carbonate; In acetone; at 20℃;	General procedure: In a typical experiment: 5-chlorosalicylaldehyde (20) (1.0 g/6.4 mmol) was placed in a two-necked round-bottom flask and then it was added Cs2CO3 (3.13 g/9.6 mmol), benzyl bromide (1.64 g/9.6 mmol) and 50 mL of acetone. The mixture was allowed to stir at room temperature overnight. The product was then filtered and washed with acetone. The solvent was evaporated and the crude product purified by column chromatography (silica gel, n-hexane/ethyl acetate 95:5). Compound 24a was obtained as white solid (1.42 g/90%).
98%	With potassium carbonate; In acetonitrile; at 20℃;Reflux;	General procedure: Benzyl bromide (0.11 mol) was added to a mixture of resorcinol derivative (0.045 mol) and potassium carbonate (0.11 mol) in acetonitrile (200 mL). The mixture was heated at reflux for 5 h and stirred overnight at room temperature. The mixture was filtered and the solid filter cake was washed with CH2Cl2 (200 mL). The combined organic fractions were evaporated in vacuo to leave the product. The crude product was triturated with hexane and filtered to give the pure product.
95%	With potassium carbonate; In acetonitrile; for 24h;Reflux;	General procedure: Benzaldehydes 20-24 (5.00g), benzyl bromide (1.0 equiv.), potassium carbonate (1.0 equiv.) and acetonitrile (50mL) were added to a 250mL round-bottom flask and the reaction mixture was refluxed for 24h. Acetonitrile was evaporated on completion of the reaction and the residues were partitioned between dichloromethane and water. The dichloromethane layer was dried with anhydrous MgSO4 and evaporated in vacuo to give benzyl-protected benzaldehydes 25-29 as a white or grey solid in yields of 95-97%.

95%	With potassium carbonate; In acetonitrile; for 24h;Reflux;	General procedure: Benzaldehydes 11-15 (5.00 g), benzyl bromide (1.0 equiv.), potassiumcarbonate (1.0 equiv.) and acetonitrile (50 mL) were added to a250 mL round-bottom flask and the reaction mixture was refluxed for24 h. Acetonitrile was evaporated on completion of the reaction and theresulting residues were partitioned between dichloromethane andwater. The dichloromethane layer was dried with MgSO4, filtered, andevaporated under reduced pressure to give the products 16-20 as awhite or grey solid in yields of 95 - 97%.
95%	With potassium carbonate; In acetonitrile; for 15h;Reflux;	To a solution of compound 1 (3.0 g, 20.0 mmol) in 120 ml of MeCN are added K2C03 (13.8 g, 100.0 mmol) and BnBr (15.05 g, 88.0 mmol). The reaction mixture is refluxed for 15 hours. After cooling to room temperature, the mixture is filtered and the filtrate is concentrated to dryness. The resulting residue is purified by chromatography on a column of silica gel using dichloro methane, to give 12.1 g of compound 2 in the form of a white powder in a yield of 95%.
95%	With potassium carbonate; In acetonitrile; for 24h;Reflux;	General procedure: Benzaldehyde 21 - 25 (5.00 g), benzyl bromide (1.0 equiv.), potassiumcarbonate (1.0 equiv.) and acetonitrile (50 mL) were added to a250 mL round-bottom flask and the reaction mixture was refluxed for24 h. Volatiles were evaporated on completion of the reaction and the resultant residues were partitioned between dichloromethane andwater. The organic layer was dried with anhydrous MgSO4 and evaporatedin vacuo to provide the products 26-30 as a white solid in yieldsof 95 - 97%. Spectroscopic data can be found in SI.
91.5%	With potassium carbonate;Reflux;	A mixture of compound A (200 g, 1.44 mol), BnBr (345 mL, 2.88 mol) and K2CO3 (300 g, 2.16 mol) in acetone was refluxed over night. The reaction mixture was filtered and the filtrate was concentrated to give compound B (421 g, 91.5%). 85% meta-perchlorobenzoic acid (348 g, 1.72 mol) was added, with stirring, at ambient temperature to a solution of compound B (421 g, 1.32 mol) in 4000 mL anhydrous methylene chloride. After stirring for 30 minutes, the mixture was filtered and the filtrate was washed with a solution of sodium bicarbonate, then with a solution of NaHSO3 and finally with water. After drying on sodium sulphate, the solvent was evaporated, the residue were taken up in methanol (2000 mL) and water (2000 mL), NaOH (263.8 g, 6.60 mol) was added and stirring was carried out for 30 minutes after which the mixture was acidified with concentrated HCl. One extracts with methylene chloride and then washed with water until neutral. After drying on sodium sulphate, the solvent was evaporated, compound C (300 g, 74%) was obtained. A mixture of compound C (22 g, 71.89 mmol), 1-bromo-2-methoxyethane (13.4 mL, 14.38 mmol) and K2CO3 (30 g, 21.57 mmol) in DMF was stirred at 80 C. over night. The reaction mixture was filtered and filtrate was concentrated to give compound D (20 g, 84%). A slurry of compound D (20 g, 54.94 mmol) and Pd/C (4.0 g) in methanol (500 mL) was stirred at ambient temperature for 4 hours under 2 atm H2 (30 PSI). The mixture was filtered and filtrate was concentrated, the residue was purified by column chromatogram to give compound 1 (9.7 g, 95%).
90%	With potassium carbonate; In acetonitrile; for 2h;Reflux;	Potassium carbonate (25.0 g, 181 mmol) and benzyl bromide (27.3 g, 160 mmol) were added to a solution of 2,4-dihydroxybenzaldehyde (10.0 g, 72.5 mmol) in 100 ml of acetonitrile. The reaction mixture was refluxed for 2 hours. After cooling, the mixture was filtered and the filtrate was concentrated to dryness under vacuum. 100 ml of hexane were then added and the mixture was stirred at room temperature for 30 minutes. The resulting white solid was collected by filtration to give 20.7 g of compound B in a yield of 90%.
88%	With potassium carbonate; at 60℃; for 3h;	2,4-Dihydroxybenzaldehyde (1.0 g, 7.2 mmol) was dissolved in 5 mL of DMF, BnBr (2.15 mL, 18 mmol) and K2CO3 (3.0 g, 22 mmol) were added and stirred at 60 C. for 3 hours. Ethyl acetate (50 mL) was added to the reaction solution, and the obtained organic layer was washed three times each with water (10 mL) and saturated brine (10 mL). The aqueous layers were combined and further extracted three times with ethyl acetate (10 mL), and all the obtained organic layers were dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was filtered off, and the filtrate was concentrated to give a crude product. Hexane was added to this product to crystallize to obtain 2.0 g of white crystal 2,4-dibenzyloxybenzaldehyde (yield: 88%) represented by the following formula.
84%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 3.5h;	To a solution of 2,4-dihydroxybenzaldehyde (5.00 g, 36.2 mmol) in N,N-dimethylformamide (30 ml) were added potassium carbonate (12.0 g, 86.9 mmol) and benzyl bromide (9.48 ml, 79.6 mmol). After stirring at room temperature for 3 hr 30 min, water (100 ml) and hexane (50 ml) were added, and the precipitated solid was collected by filtration. The solid was washed with water (3 ml×3) and hexane (5 ml) and dried under reduced pressure to give 2,4-bisbenzyloxybenzaldehyde (9.67 g, yield 84%). 1H-NMR (400 MHz, deltappm, DMSO-d6) 10.23(1H, s), 7.68(1H, d, J=8.4 Hz), 7.50-7.32(10H, m), 6.92(1H, d, J=2.0 Hz), 6.75(1H, dd, J=8.8, 2.0 Hz), 5.27(2H, s), 5.21(2H, s).
10.03%		Intermediate 128: 2, 4-Bis (benzyloxy) benzaldehydeTo a 250 mL RB flask fitted with magnetic stirrer was charged 100 mL of acetonitrile.To the stirred solvent was added 2, 4-dihydroxybenzaldehyde (10.0 g, 72.0 mmol) and K2C03 (19.87 g, 144.0 mmol). Then it was stirred for 15 min, slowly was added benzylbromide (12.38 g, 72.0 mmol), the RM was heated to 80 "C fo r 3 h. Then, the solvent was removed under reduced pressure and the compound was extracted with ethyl acetate (50 mL X 3). The organic layer washed with water and saturated brine solution and dried over anhydrous Na2S04 and evaporated to dryness to get the crude product. The crude material was purified by silica gel column chromatography using ethyl acetate and petroleum ether as elutants to obtain the product (2.3 g, yield: 10.03%).
	With potassium carbonate; In butanone;	In the following scheme, 2,4-dihydroxybenzaldehyde is converted to the corresponding dibenzyl ether (8A) upon treatment with benzyl bromide and potassium carbonate in methyl ethyl ketone. Treatment of 8A with 4-cyanoaniline (9A) results in the formation of imine 1OA in good yield, hi the next step, 7b A is treated with titanium tetrachloride and N-ethyldiisopropylamine followed by treatment with 1OA to effect enantiospecific condensation to provide HA. Treatment of HA with excess N,O- bistrimethylsilyl-acetamide followed by a catalytic amount of tetrabutylammonium fluoride hydrate results in ring closure to the desired beta-lactam (12aA) while maintaining the TBS protecting group on the benzylic alcohol. Reduction of the nitrile is EPO <DP n="248"/>then accomplished by treatment with hydrogen in ethanol catalyzed by raney nickel to provide 12bA.
	With potassium carbonate; In ice-water; N,N-dimethyl-formamide;	EXAMPLE 14 Compound AM A mixture of 2,4-dihydroxybenzaldehyde (17.5 g), potassium carbonate (42 g) and benzyl bromide (35 mL) in dimethyl formamide (100 mL) is stirred at room temperature for 18 hours. The reaction mixture is poured into vigorously stirred ice-water (300 mL) and stirring is continued for 30 minutes. The resulting brown solid is filtered and dried to give 2,4-dibenzyloxybenzaldehyde (28.5 g), m.p. 80-81 C. [Elemental analysis:- C,79.5; H,6.10%. Calculated:- C,79.2; H,5.70%].
	With potassium carbonate; In butanone;	In the following scheme, 2,4-dihydroxybenzaldehyde was converted to the corresponding dibenzyl ether (11) upon treatment with benzyl bromide and potassium carbonate in methyl ethyl ketone. Treatment of 11 with aniline (2) resulted in the formation of the corresponding imine 12 in good yield. Treatment of 4 with triphosgene [(Cl3CO)2CO] and triethylamine in the presence of 12 provides the beta-lactam 13. A solution of ketal 13 is dissolved in tetrahydrofuran and water with a catalytic amount of /?alphar°-toluenesulfonic acid to effect hydrolysis to the alcohol 14. The alcohol 14 is then treated with sodium methoxide in methanol to effect conversion to the methyl ester with beta-lactam ring opening. Reaction of the resulting alcohol with triphosgene in the EPO <DP n="252"/>presence of diisopropylethylamine and NN-dimethylaminopyridine gives the oxazolidinone 15. The ester moiety of 15 is then converted into the corresponding hydroxymethyl substituent upon treatment with sodium cyanoborohydride. Swern oxidation converts the hydroxymethyl substituent into the corresponding aldehyde which is then reacted with the Wittig reagent l-(4-fluorophenyl)-2-triphenyl-lambda5-phosphanylidene)-ethanone to give the ketone 16. Catalytic hydrogenation of 16 over palladium on carbon removes the benzyl protecting groups and reduces the double bond to give ketone 17 which is reduced with borane dimethylsulfide complex in the presence of a catalytic amount of tetrahydro-1- methyl-3,3-diphenyl-lH,3H-pyrrolo[l,2-c][l,3,2]oxazaborole, (R-CBS) to give the desired compound 18.; In the following scheme, 2,4-dihydroxybenzaldehyde was converted to the corresponding dibenzyl ether (11) upon treatment with benzyl bromide and potassium carbonate in methyl ethyl ketone. Treatment of 11 with aniline (2) resulted in the formation of the corresponding imine 12 in good yield. Treatment of 175 with triphosgene [(Cl3CO)2CO] and triethylamine in the presence of 12 provides the beta-lactam 182. A solution of thioketal 182 is dissolved in tetrahydrofuran and water with a catalytic amount of palphara-toluenesulfonic acid to effect hydrolysis to the thiol 183. The thiol 183 is then EPO <DP n="282"/>treated with sodium methoxide in methanol to effect conversion to the methyl ester with beta-lactam ring opening. Reaction of the resulting thiol with triphosgene in the presence of diisopropylethylamine and N,N-dimethylaminopyridme gives the l,3-thiazolidin-2-one 184. The ester moiety of 184 is then converted into the corresponding hydroxymethyl substituent upon treatment with sodium cyanoborohydride. Swern oxidation converts the hydroxymethyl substituent into the corresponding aldehyde which is then reacted with the Wittig reagent l-(4-fluorophenyl)-2-triphenyl-lambda5-phosphanylidene)-ethanone to give the ketone 185. Catalytic hydrogenation of 185 over palladium on carbon removes the ben2yl protecting groups and reduces the double bond to give ketone 186 which is reduced with borane dimethylsulfide complex in the presence of a catalytic amount of tetrahydro-1- methyl-3,3-diphenyl-lH,3H-pyrrolo[l,2-c][l,3,2]oxazaborole, (R-CBS) to give the desired compound 187.
	With potassium carbonate; In acetone; for 10.5h;Reflux;	One eq 2',4'-dihydroxybenzaldehyde was dissolved in acetone and2.4 eq potassium carbonate were added under reflux, followed by the dropwise addition of 2.1 eqbenzyl bromide over 30 min. The mixture was reuxed for 10 h and cooled down to room temperature.After removal of the precipitated salts by filtration, the filtrate was evaporated to dryness. The crudeproduct was then recrystallized from acetone (97.8% purity as determined by GC).

Reference： [1]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 1429 - 1437
[2]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 2941 - 2959
[3]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6055 - 6068
[4]Journal of Natural Products,2017,vol. 80,p. 1294 - 1301
[5]Tetrahedron Letters,2002,vol. 43,p. 291 - 293
[6]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3151 - 3153
[7]MedChemComm,2013,vol. 4,p. 1613 - 1618
[8]European Journal of Medicinal Chemistry,2019,vol. 161,p. 78 - 92
[9]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 5672 - 5681
[10]Patent: WO2019/63710,2019,A1 .Location in patent: Page/Page column 18
[11]Bioorganic Chemistry,2019,vol. 87,p. 43 - 55
[12]Patent: JP2015/214548,2015,A .Location in patent: Paragraph 1145; 1146
[13]Journal of Natural Products,2008,vol. 71,p. 275 - 277
[14]Patent: WO2018/210933,2018,A1 .Location in patent: Page/Page column 15-18; 22-29
[15]Patent: JP5893442,2016,B2 .Location in patent: Paragraph 0062; 0063; 0064
[16]Journal of Organic Chemistry,2003,vol. 68,p. 5992 - 5999
[17]Patent: US2006/167246,2006,A1 .Location in patent: Page/Page column 155
[18]European Journal of Medicinal Chemistry,1997,vol. 32,p. 409 - 423
[19]Patent: WO2012/11125,2012,A1 .Location in patent: Page/Page column 160
[20]Rikagaku Kenkyusho Iho,1940,vol. 19,p. 802,803
Chem.Abstr.,1940,p. 5842
[21]Patent: WO2006/86562,2006,A2 .Location in patent: Page/Page column 246-247
[22]Patent: US6211234,2001,B1
[23]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 6707 - 6714
[24]Journal of Enzyme Inhibition and Medicinal Chemistry,2011,vol. 26,p. 643 - 648
[25]Archives of Pharmacal Research,2011,vol. 34,p. 1065 - 1070
[26]Patent: WO2006/102674,2006,A2 .Location in patent: Page/Page column 250-252; 280-281
[27]Molecules,2020,vol. 25

2
[ 100-44-7 ]
[ 95-01-2 ]
[ 13246-46-3 ]

Yield	Reaction Conditions	Operation in experiment
60%	With sodium carbonate; In ethanol;	(i) 2,4-Dihydroxybenzaldehyde (14.5 g) was dissolved in ethanol (60 ml) and then thereto were added benzyl chloride (30 ml) and sodium carbonate (1.7 g), followed by reflux under heating for 5 hours. Insoluble matters were removed by filtration. The filtrate was allowed to stand for cooling and then the produced solid was collected by filtration and recrystallized from ethanol to obtain 2,4-dibenzyloxybenzaldehyde (20 g, yield 60%). Melting point: 89-90 C.
		General procedure: The hydroxyl group in aldehyde A was protected by etherizing with benzyl chloride before used in the following synthesis. Briefly, hydroxyl-substituted benzaldehyde (10mmol) and K2CO3 (2.07g, 15mmol) were refluxed in 10mL of 95% ethanol for 0.5h, then, benzyl chloride (1.55g, 12mmol) was added and refluxed for 6h. The reaction mixture was cooled to room temperature and filtered to remove inorganic salt. The organic solvent was removed under vacuum to yield benzoxyl-substituted benzaldehyde (>90%).
		General procedure: In brief, the preparation of 2-phenylmethoxylbenzaldehyde was taken as an example. 2-Hydroxybenzaldehyde (1.22 g, 10 mmol) and K2CO3 (2.07 g, 15 mmol) were refluxed in 10 mL of 95% ethanol for 0.5 h, then benzyl chloride (1.55 g, 12 mmol) was added and refluxed for 6 h. The reaction mixture was cooled to room temperature and filtered to remove inorganic salt. The organic solvent was removed under vacuum to yield 2-phenylmethoxylbenzaldehyde. The yields of this reaction were generally >90%.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 6758 - 6763
[2]Russian Journal of Bioorganic Chemistry,2009,vol. 35,p. 752 - 758
[3]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 439 - 443
[4]Tetrahedron,2010,vol. 66,p. 197 - 207
[5]Tetrahedron Letters,1987,vol. 28,p. 3511 - 3514
[6]Journal of Heterocyclic Chemistry,2001,vol. 38,p. 1007 - 1009
[7]Patent: US5047430,1991,A
[8]Helvetica Chimica Acta,1935,vol. 18,p. 816,826
[9]European Journal of Medicinal Chemistry,2013,vol. 68,p. 385 - 393
[10]Tetrahedron,2014,vol. 70,p. 8397 - 8404

3
[ 552-41-0 ]
[ 13246-46-3 ]
[ 67685-25-0 ]

Reference： [1]Journal of Natural Products,2008,vol. 71,p. 275 - 277
[2]Journal of Heterocyclic Chemistry,2001,vol. 38,p. 1007 - 1009
[3]Journal of the Chemical Society. Perkin transactions I,1986,p. 1561 - 1564

4
[ 13246-46-3 ]
[ 6195-80-8 ]

Yield	Reaction Conditions	Operation in experiment
74%		A mixture of compound A (200 g, 1.44 mol), BnBr (345 mL, 2.88 mol) and K2CO3 (300 g, 2.16 mol) in acetone was refluxed over night. The reaction mixture was filtered and the filtrate was concentrated to give compound B (421 g, 91.5%). 85% meta-perchlorobenzoic acid (348 g, 1.72 mol) was added, with stirring, at ambient temperature to a solution of compound B (421 g, 1.32 mol) in 4000 mL anhydrous methylene chloride. After stirring for 30 minutes, the mixture was filtered and the filtrate was washed with a solution of sodium bicarbonate, then with a solution of NaHSO3 and finally with water. After drying on sodium sulphate, the solvent was evaporated, the residue were taken up in methanol (2000 mL) and water (2000 mL), NaOH (263.8 g, 6.60 mol) was added and stirring was carried out for 30 minutes after which the mixture was acidified with concentrated HCl. One extracts with methylene chloride and then washed with water until neutral. After drying on sodium sulphate, the solvent was evaporated, compound C (300 g, 74%) was obtained. A mixture of compound C (22 g, 71.89 mmol), 1-bromo-2-methoxyethane (13.4 mL, 14.38 mmol) and K2CO3 (30 g, 21.57 mmol) in DMF was stirred at 80 C. over night. The reaction mixture was filtered and filtrate was concentrated to give compound D (20 g, 84%). A slurry of compound D (20 g, 54.94 mmol) and Pd/C (4.0 g) in methanol (500 mL) was stirred at ambient temperature for 4 hours under 2 atm H2 (30 PSI). The mixture was filtered and filtrate was concentrated, the residue was purified by column chromatogram to give compound 1 (9.7 g, 95%).
72%		Under argon atmosphere,Dissolve <strong>[13246-46-3]2,4-dibenzyloxybenzaldehyde</strong> (2.0 g, 6.3 mmol) and mCPBA (3.6 g, 16 mmol) in 30 mL of dichloromethane,Refluxed overnight.Ethyl acetate (50 mL) is added to the reaction solution,The organic layer is 5% aqueous sodium thiosulfate (10 mL),Water (10 mL),It was washed with 5% aqueous sodium hydrogen carbonate solution (10 mL) and saturated brine (10 mL).Anhydrous sodium sulfate is added to the obtained organic layer and it is dried,After filtering out sodium sulfate,The filtrate was concentrated under reduced pressure.To the concentrate was added 20 mL of methanol and 8 mL of 6 M aqueous NaOH solution, and the resulting solution was stirred at room temperature for 3 hours. The reaction was acidified with 2 M hydrochloric acid and ethyl acetate (50 mL) was added. The organic layer was washed three times with water (10 mL) and saturated brine (10 mL). The aqueous layers were combined and further extracted three times with ethyl acetate (10 mL), and all the obtained organic layers were dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was filtered off, and the filtrate was concentrated to give a crude product. The crude product was purified by silica gel column chromatography (20 to 30% ethyl acetate / hexane) to obtain 1.4 g of 2,4-dibenzyloxyphenol as white crystals represented by the following compound (yield:72%).

Reference： [1]Journal of Natural Products,2017,vol. 80,p. 1294 - 1301
[2]Patent: JP2015/214548,2015,A .Location in patent: Paragraph 1145; 1146
[3]Patent: JP5893442,2016,B2 .Location in patent: Paragraph 0065; 0066; 0067
[4]European Journal of Medicinal Chemistry,1997,vol. 32,p. 409 - 423
[5]Journal of the Chemical Society. Perkin transactions I,1993,p. 1153 - 1160
[6]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3151 - 3153
[7]Tetrahedron Letters,2002,vol. 43,p. 291 - 293
[8]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 6707 - 6714

5
[ 13246-46-3 ]
[ 33617-58-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium borohydrid; In methanol; water;	(ii) 2,4-Dibenzyloxybenzaldehyde (20 g) was dissolved in methanol (700 ml) and then thereto was added sodium borohydride (3.6 g) and this was left to stand at room temperature (20 C.) for 1.5 hours. To the reaction mixture was added water (1.5 l) and the resulting precipitate was collected by filtration and recrystallized from ethanol to obtain 2,4-dibenzyloxybenzyl alcohol (19.8 g, yield 98%). Melting point; 84-85 C.
	With sodium borohydrid; In methanol; water; Petroleum ether;	EXAMPLE 15 Compound AN A solution of <strong>[13246-46-3]2,4-dibenzyloxybenzaldehyde</strong> (2.26 g) in methanol (20 mL) is treated portionwise with sodium borohydride (0.268 g) over 5 minutes. Water (5 mL) is added dropwise to the reaction mixture. The resulting white solid is filtered, dried and crystallized from a mixture of ether and petroleum ether to give 2,4-dibenzyloxybenzyl alcohol as a white solid, m.p. 87 C. [Elemental analysis:- C,79.0; H,6.42%. Calculated:- C,78.7; H,6.29%].

Reference： [1]Tetrahedron Letters,1987,vol. 28,p. 3511 - 3514
[2]Patent: US5047430,1991,A
[3]Russian Journal of Bioorganic Chemistry,2009,vol. 35,p. 752 - 758
[4]European Journal of Medicinal Chemistry,1997,vol. 32,p. 409 - 423
[5]Justus Liebigs Annalen der Chemie,1971,vol. 750,p. 109 - 127
[6]Patent: US6211234,2001,B1

7
[ 22877-01-6 ]
[ 13246-46-3 ]
2,4,2',4'-tetrabenzyloxychalcone [ No CAS ]

Reference： [1]Phytochemistry,1995,vol. 39,p. 575 - 580
[2]Journal of Enzyme Inhibition and Medicinal Chemistry,2011,vol. 26,p. 643 - 648

8
[ 495-69-2 ]
[ 13246-46-3 ]
4-(2,4-dibenzyloxybenzylidene)-2-phenyl-4H-oxazol-5-one [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1997,vol. 32,p. 409 - 423

9
[ 558-13-4 ]
[ 13246-46-3 ]
[ 170281-92-2 ]

Reference： [1]European Journal of Medicinal Chemistry,1997,vol. 32,p. 409 - 423

10
[ 13246-46-3 ]
[ 142570-65-8 ]
[ 170282-04-9 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In tetrahydrofuran;	Reference Example 13 A stirred solution of triethyl 2-phosphono-3-phenylpropionate (5.17 g) in dry tetrahydrofuran (50 mL) is treated with a solution of n-butyl lithium in hexanes (8 mL, 2.5 M) at -78 C. After stirring for 15 minutes a solution of <strong>[13246-46-3]2,4-dibenzyloxybenzaldehyde</strong> (5 g) in dry tetrahydrofuran (50 mL) is added dropwise over 5 minutes at -78 C. The reaction mixture is stirred at -78 C. for 1 hour and allowed to warm to room temperature. After standing at room temperature for 18 hours the reaction mixture is evaporated and the residue partitioned between ethyl acetate (120 mL) and water (75 mL). The organic phase is washed with brine (50 mL), dried over magnesium sulphate and evaporated. The residue is purified by flash chromatography on silica eluding with dichloromethane. Fractions homogeneous in the required product are evaporated to give ethyl (E)-2-benzyl-3-(2,4-dibenzyloxyphenyl)acrylate (1.5 g) as a yellow oil.

Reference： [1]European Journal of Medicinal Chemistry,1997,vol. 32,p. 409 - 423
[2]Patent: US6211234,2001,B1

11
[ 13246-46-3 ]
[ 3162-51-4 ]
[ 204591-00-4 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1998,vol. 46,p. 222 - 230

12
[ 13246-46-3 ]
[ 208581-35-5 ]
[ 208581-36-6 ]

Reference： [1]Angewandte Chemie - International Edition,1998,vol. 37,p. 938 - 941
[2]Journal of the American Chemical Society,1999,vol. 121,p. 7318 - 7329

13
[ 1816-92-8 ]
[ 13246-46-3 ]
[ 420137-04-8 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 901 - 914
[2]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3859 - 3861

14
[ 13246-46-3 ]
[ 6147-11-1 ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 291 - 293

15
[ 56921-01-8 ]
[ 13246-46-3 ]
[ 886973-12-2 ]

Yield	Reaction Conditions	Operation in experiment
82%	With pyrrolidine; In ethanol; for 1h;Heating / reflux;	To a solution of methyl 4-nitro-5-methylthiophene-2-carboxylate (1.50 g, 7.46 mmol) in ethanol (7.5 ml) were added <strong>[13246-46-3]2,4-bisbenzyloxybenzaldehyde</strong> (2.49 g, 7.83 mmol) and pyrrolidine (0.65 ml, 7.83 mmol). After stirring for 1 hr with heating under reflux, the reaction mixture was allowed to cool to room temperature. The precipitated solid was collected by filtration. The solid was washed with ethanol (3 ml×3), and dried under reduced pressure to give methyl (E)-5-[2-(2,4-bisbenzyloxyphenyl)vinyl]-4-nitrothiophene-2-carboxylate (3.08 g, yield 82%). 1H-NMR (400 MHz, deltappm, DMSO-d6) 8.08(1H, s), 8.04(1H, d, J=16.0 Hz), 7.64(1H, d, J=8.8 Hz), 7.60(1H, d, J=16.0 Hz), 7.50-7.32(10H, m), 6.87(1H, d, J=2.0 Hz), 6.73(1H, dd, J=8.8, 2.4 Hz), 5.26(2H, s), 5.17(2H, s), 3.86(3H, s).

Reference： [1]Patent: US2006/167246,2006,A1 .Location in patent: Page/Page column 155

16
1-(5-benzyloxy-2-methoxy-3,4,6-trimethyl-phenyl)-ethanone [ No CAS ]
[ 13246-46-3 ]
3-(2,4-dibenzyloxy-phenyl)-1-(5-benzyloxy-2-methoxy-3,4,6-trimethyl-phenyl)-propenone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With hydrogenchloride; sodium hydroxide; In tetrahydrofuran; ethanol;	PREPARATION 2 Synthesis of 3-(2,4-dibenzyloxy-phenyl)-1-(5-benzyloxy-2-methoxy-3,4,6-trimethyl-phenyl)-propenone STR16 0.23 g(0.77 mmol) of 1-(5-benzyloxy-2-methoxy-3,4,6-trimethyl-phenyl)-ethanone and 0.62 g(1.94 mmol) of <strong>[13246-46-3]2,4-dibenzyloxybenzaldehyde</strong> were dissolved in 7 ml of a solvent mixture of ethanol and tetrahydrofuran(1/1, v/v) and then 1.5 ml of 50% aqueous sodium hydroxide solution was slowly added dropwise thereto. After the addition was completed, the mixture was stirred for 16 hours at normal temperature. The solvent contained therein was removed, the residue was diluted with water and neutralized to pH 7 using 10% aqueous hydrochloric acid solution. This solution was extracted with ethylacetate and the solvent was removed by distillation under reduced pressure. The residue having a high viscosity was subjected to a silica gel column chromatography (eluent: n-hexane/ethylacetate=7/1, v/v) to obtain 0.30 g(Yield 65%) of the title compound.

Reference： [1]Patent: US6093836,2000,A

17
1-(2-benzyloxy-5-ethoxy-3,4,6-trimethyl-phenyl)-ethanone [ No CAS ]
[ 13246-46-3 ]
3-(2,4-dibenzyloxy-phenyl)-1-(2-benzyloxy-5-ethoxy-3,4,6-trimethyl-phenyl)-propenone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With hydrogenchloride; sodium hydroxide; In tetrahydrofuran; ethanol;	PREPARATION 4 Synthesis of 3-(2,4-dibenzyloxy-phenyl)-1-(2-benzyloxy-5-ethoxy-3,4,6-trimethyl-phenyl)-propenone STR22 310 mg(1 mmol) of 1-(2-benzyloxy-5-ethoxy-3,4,6-trimethyl-phenyl)-ethanone and 650 mg(2.1 mmol) of <strong>[13246-46-3]2,4-dibenzyloxy-benzaldehyde</strong> were dissolved in 15 ml of a solvent mixture of ethanol and tetrahydrofuran(1/1, v/v), to which was slowly added dropwise 5 mg of 50% aqueous sodium hydroxide solution. After the addition was completed, the mixture was stirred for 24 hours at normal temperature. The solvent contained in the reaction solution was removed by distillation under reduced pressure, the resulting residue was diluted with 10 ml of water and then neutralized to pH 7 using 10% aqueous hydrochloric acid solution. This solution was extracted with ethylacetate and the solvent contained in the extract was removed by distillation under reduced pressure. The residue was subjected to a silica gel column chromatography (eluent: n-hexane/ethylacetate=7/1, v/v) to obtain 440 mg(Yield 72%) of the title compound.

Reference： [1]Patent: US6093836,2000,A

18
1-(6-benzyloxy-2,2,7,8-tetramethyl-chroman-5-yl)-ethanone [ No CAS ]
[ 13246-46-3 ]
3-(2,4-dibenzyloxy-phenyl)-1-(6-benzyloxy-2,2,7,8-tetramethyl-chroman-5-yl)-propenone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With hydrogenchloride; sodium hydroxide; In tetrahydrofuran; ethanol; water;	PREPARATION 5 Synthesis of 3-(2,4-dibenzyloxy-phenyl)-1-(6-benzyloxy-2,2,7,8-tetramethyl-chroman-5-yl)-propenone STR24 1.69 g(5 mmol) of 1-(6-benzyloxy-2,2,7,8-tetramethyl-chroman-5-yl)-ethanone and 3.2 g(10.5 mmol) of <strong>[13246-46-3]2,4-dibenzyloxy-benzaldehyde</strong> were dissolved in 50 ml of a solvent mixture of ethanol and tetrahydrofuran(1/1, v/v), to which was slowly added dropwise 10 ml of 50% aqueous sodium hydroxide solution. After the addition was completed, the mixture was stirred for 16 hours at normal temperature. After the solvent contained in the reaction solution was removed by distillation under reduced pressure, the residue was diluted with 50 ml of water and then neutralized to pH 7 using 10% aqueous hydrochloric acid solution. This solution was extracted with ethylacetate and the solvent contained in the extract was removed by distillation under reduced pressure. The residue was subjected to a silica gel column chromatography(eluent: n-hexane/ethylacetate=7/1, v/v) to obtain 2.13 g(Yield 68%) of the title compound.

Reference： [1]Patent: US6093836,2000,A

19
2,4-dihydroxybenzaldehyde [IV] [ No CAS ]
[ 100-44-7 ]
[ 13246-46-3 ]

Yield	Reaction Conditions	Operation in experiment
60%	With sodium carbonate; In ethanol;	(i) 2,4-Dihydroxybenzaldehyde [IV] (14.5 g) was dissolved in ethanol (60 ml) and then thereto were added benzyl chloride (30 ml) and sodium carbonate (1.7 g), followed by reflux under heating for 5 hours. Insoluble matters were removed by filtration. The filtrate was allowed to stand for cooling and then the produced solid was collected by filtration and recrystallized from ethanol to obtain 2,4-dibenzyloxybenzaldehyde [V] (20 g, yield 60%). Melting point: 89-90 C.
60%	With sodium carbonate; In ethanol;	(i) 2,4-Dihydroxybenzaldehyde [IV] (14.5 g) was dissolved in ethanol (60 ml) and then thereto were added benzyl chloride (30 ml) and sodium carbonate (1.7 g), followed by reflux under heating for 5 hours. Insoluble matters were removed by filtration. The filtrate was allowed to stand for cooling and then the produced solid was collected by filtration and recrystallized from ethanol to obtain 2,4-dibenzyloxybenzaldehyde [V] (20 g, yield 60%). Melting point: 89-90 C.

Reference： [1]Patent: US4918107,1990,A
[2]Patent: US4990614,1991,A

20
[ 558-13-4 ]
[ 13246-46-3 ]
[ 791-28-6 ]
[ 170281-92-2 ]

Yield	Reaction Conditions	Operation in experiment
67%	With triphenylphosphine; In dichloromethane; pentane;	Reference Example 3 A mixture of triphenylphosphine (15.7 g) and carbon tetrabromide (9.93 g) in dry dichloromethane (100 mL) is cooled to 0 C. and stirred for 30 minutes. A solution of <strong>[13246-46-3]2,4-dibenzyloxybenzaldehyde</strong> (4.76 g) in dichloromethane (30 mL) is added and the solution stirred at 0 C. for 2 hours. The solution is treated with pentane to precipitate triphenylphosphine oxide. The filtrate is evaporated to give 1-(2,4-dibenzyloxyphenyl)-2,2-dibromoethylene as a yellow oil (4.85 g, 67%).

Reference： [1]Patent: US6211234,2001,B1

21
[ 13246-46-3 ]
[ 33670-32-5 ]
C₂₃H₂₂O₃ [ No CAS ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 197 - 207

22
[ 13246-46-3 ]
[ 1779-49-3 ]
[ 1092064-97-5 ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 197 - 207

23
[ 329-89-5 ]
[ 931-53-3 ]
[ 13246-46-3 ]
[ 1251607-07-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With montmorillonite clay K10; In 1,4-dioxane; at 110℃; for 40h;	6-Aminonicotinamide (0.500 g, 3.64 mmol), 2,4-bis(benzyloxy)benzaldehyde (1.160 g, 3.64 mmol), cyclohexyl isocyanide (0.398 g, 3.64 mmol) and K10 (0.50 g) was dissolved in 1,4-dioxane (20 mL) at rt. The reaction mixture was refluxed for 40 h at 110 °C while monitoring the reaction progress with TLC. After work-up of the reaction as described previously, the residue obtained was subjected column chromatography on silica gel (ethyl acetate) to furnish a yellow compound which was crystallized from hexane to give pure desired product 2-(2,4-bis(benzyloxy)phenyl)-3-(cyclohexylamino)imidazo[1,2-a]pyridine-6-carboxamide 7 (1.70 g, 85percent) as a yellow solid. Mp = 112-115 °C; IRnumax (cm-1) = 2924, 1667, 1607, 1504, 1452, 1366; 1H NMR (300 MHz, CDCl3) delta 8.75 (s, 1H), 7.80 (d, J = 9.1, 1H), 7.49-7.27 (m, 12H), 6.81-6.72 (m, 2H), 6.52 (br s, 1H), 5.08 (s, 2H), 5.05 (s, 2H), 3.88 (d, J = 8.1, 1H), 2.71-2.55 (m, 1H), 1.68-1.40 (m, 5H), 1.13-0.83 (m, 5H); 13C NMR (75 MHz, CDCl3) delta 167.8, 159.9, 156.2, 141.7, 136.7, 136.0, 135.0, 132.6, 128.8, 128.7, 128.5, 128.2, 127.8, 127.7, 124.9, 121.6, 118.3, 117.2, 116.4, 107.4, 101.6, 71.7, 70.3, 56.6, 34.0, 25.7, 24.8; HRMS (m/z) calculated for C34H35N4O3, (M + H), 547.2709, found 547.2707.

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 4573 - 4583

24
[ 13246-46-3 ]
[ 22013-33-8 ]
[ 1344729-71-0 ]

Yield	Reaction Conditions	Operation in experiment
90.5%	In ethanol; for 3h;Reflux;	General procedure: The appropriate amine (10 mmol) was heated at reflux with the appropriate aldehyde (10 mmol) in ethanol (50 mL) for 3 h. The reaction mixture was cooled and then the solvent evaporated in vacuo. The resulting solid product was recrystallised from ethanol.

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6055 - 6068

25
[ 867-13-0 ]
[ 13246-46-3 ]
[ 1356601-48-3 ]

Yield	Reaction Conditions	Operation in experiment
82.14%		Intermediate 129: Ethyl (2£)-3-[2, 4-bis (benzyloxy) phenyl] prop-2-enoateTo a 100 mL RB flask fitted with magnetic stirrer was charged with 25 mL of tetrahydrofuran. To the stirred solvent was added sodium hydride (0.35 g, 14.0 mmol) portion wise at 0 C, followed by triethyl phosphonoacetate (3.23 g, 14.0 mmol). The reaction mixture was stirred at 0 C for 30 minutes. To the stirring solution, 2, 4-bis (benzyloxy) benzaldehyde (2.3 g, 7.2 mmol) in tetrahydrofuran (2 mL) was added drop wise and stirred at room temperature 16 h. After completion of the reaction, the reaction mixture was poured into ice and extracted with ethyl acetate (50 mL). The organic layer was washed with water (25 mL) and saturated brine solution (25 mL). The organic layer was dried over anhydrous Na2S04 and the solvent was removed under reduced pressure. The crude material was purified by silica gel column chromatography using ethyl acetate and petroleum ether as elutants. The product was obtained as colourless oil (2.3 g, yield: 82.14%).
	With potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; N,N-dimethyl-formamide; at 70℃;	General procedure: To a stirred solution of compounds 25-29 (2.00g), triethyl phosphonoacetate (1.1 equiv.), and potassium carbonate (2.0 equiv.) in dichloromethane/N,N-dimethylformamide (2:1, 15mL) was added a catalytic amount of DBU (0.03 equiv.). The reaction mixture was stirred at room temperature (compounds 25, 27, and 29) or 70C (26, and 28) for 24-36h. After removal of dichloromethane by evaporation, ice water was added to the reaction mixture which was then stirred for 30min to give precipitates. After filtration, the filter cake was washed with plenty of water, and dried to produce ethyl cinnamates 30-34 as a white or grey solid in yields of 95-98%. The ethyl cinnamates were used directly in the next reaction without characterization.
	With potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; N,N-dimethyl-formamide; at 70℃;	General procedure: To a stirred solution of compounds 16-20 (2.00 g), triethyl phosphonoacetate(1.1 equiv.), and potassium carbonate (2.0 equiv.) in dichloromethane/N,N-dimethylformamide (2:1, 15 mL) was added acatalytic amount of DBU (0.03 equiv.). The reaction mixture was stirredat room temperature (compounds 11, 13, and 15) or 70 C (12, and 14)for 24-36 h. After evaporation of dichloromethane, ice water was addedto the reaction mixture which was then stirred for 30 min to give precipitates.After filtration, the filter cake was washed with a plenty ofwater, and dried to produce ethyl cinnamates 21-25 as a white or graysolid in yields of 95-98%. The ethyl cinnamates were used directly inthe next reaction without characterization.

With potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; N,N-dimethyl-formamide; at 70℃;

General procedure: To a stirred solution of compounds 26 - 30 (2.00 g), triethyl phosphonoacetate(1.1 equiv.), and potassium carbonate (2.0 equiv.) indichloromethane/N,N-dimethylformamide (15 mL, 2:1) was added acatalytic amount of DBU (0.03equiv., 1,8-diazabicyclo[5.4.0]undec-7-ene). The reaction mixture was stirred at room temperature (compounds26, 28, and 30) or 70 C (compounds 27, and 29) for 24 - 36 h.After removing volatiles, ice water was added to the reaction mixturewhich was then stirred at room temperature for 30 min. After thegenerated precipitates were filtered, the filter cake was washed withexcess water, and dried to provide ethyl cinnamates 31 - 35 as a whiteor grey solid in yields of 95 - 98%. The cinnamates 31 - 35 were used inthe next step without characterization.

Reference： [1]Patent: WO2012/11125,2012,A1 .Location in patent: Page/Page column 160-161
[2]European Journal of Medicinal Chemistry,2019,vol. 161,p. 78 - 92
[3]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 5672 - 5681
[4]Bioorganic Chemistry,2019,vol. 87,p. 43 - 55

26
[ 13246-46-3 ]
[ 85593-77-7 ]

Reference： [1]MedChemComm,2013,vol. 4,p. 1613 - 1618
[2]Archives of Pharmacal Research,2011,vol. 34,p. 1065 - 1070

27
[ 13246-46-3 ]
[ 1435265-53-4 ]
(2,4-bis(benzyloxy)phenyl)(8-((tert-butyldimethylsilyl)oxy)-7-methoxy-2,2-dimethyl-3,4-dihydrobenzopyran-6-yl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.2 g		General procedure: In a typical experiment: Compound 9 (1.5 g/3.74 mmol) was placed in an oven-dried three-necked round-bottom flask and solubilized in 50 mL of anhydrous THF. The mixture was then placed at -78 C and nBuLi (1.6 M, 5.6 mmol) was added dropwise. The mixture was allowed to react for 15 min at -78 C. Then the 2-benzyloxy-5-chlorosalicylaldehyde (24a) (1.38 g/5.6 mmol) solubilized in anhydrous THF was added dropwise and allowed to react for 15 min at -78 C and slowly warm to room temperature. The reaction was quenched by a saturated solution of NH4Cl, extracted with 3 × 100 mL of ethyl acetate. The organic phase was washed 2 × 100 mL of brine, dried over sodium sulfate anhydrous, filtered and the organic solvent evaporated. The crude product was then purified by silica gel flash chromatography (n-hexane/ethyl acetate 8:2) and compound 33e was obtained as light yellow oil (1.62 g/76%).

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 2941 - 2959

28
[ 13246-46-3 ]
[ 67-64-1 ]
[ 104898-57-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium hydroxide; In ethanol; water; at 0 - 20℃; for 3h;	Aqueous NaOH solution (1.25 M, 5.8 mL, 7.25 mmol) was added dropwise to a stirred suspension of 13 (1.89 g, 5.94 mmol) in acetone (5.8 mL, 77.2 mmol) and EtOH (40 mL) at 0 C. After being stirred for 2 h at 0 C, the resultant solution was stirred for 1 h at room temperature. The reaction mixture was adjust to pH 4 with 1 M aqueous HCl solution at 0 C and diluted with H2O (100 mL). The resultant mixture was extracted with EtOAc (200 mL). The organic layer was washed with 1% aqueous HCl solution (50 mL * 3) and brine (50 mL * 2). The combined aqueous layers were extracted with EtOAc (30 mL) and the combined organic layers were dried over Na2SO4. Filtration and concentration followed by recrystallization from EtOAc in hexane gave the titled compound 14 (1.99 g, 94%) as a yellow-green needle, mp 119 C. IR (film) numax 1654, 1602, 1276, 1248 cm-1. 1H NMR (400 MHz, CDCl3) delta 7.85 (d, J = 16.4 Hz, 1H, H-4), 7.49 (d, J = 8.4 Hz, 1H, H-6'), 7.40-7.33 (m, 10H, Bn), 6.67 (d, J = 16.4 Hz, 1H, H-3), 6.00-6.58 (m, 2H, H-3", H-5"), 5.10 (s, 2H, Bn), 5.04 (s, 2H, Bn), 2.30 (s, 3H, H-1).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 122 - 125
[2]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 6650 - 6658

29
[ 1273-94-5 ]
[ 13246-46-3 ]
C₅₆H₄₆FeO₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium hydroxide; In ethanol; at 20 - 23℃; for 24h;	General procedure: A mixture of 0.033 mol of 1,1'-diacetylferrocene I, 0.01 mol of benzaldehyde or substituted alkoxybenzaldehyde II, and 0.005 mol of NaOH in 50 mL of 96% ethanol was stirred at 20-23C during 24 h. The reaction mixture was diluted with 150 mL of water, and the precipitate was filtered off, washed with large amount of distilled water (1.5-2 L), and dried at 35-40C in air. Compounds III-XXXV were purified via low-temperature recrystallization from 80% ethanol.

Reference： [1]Russian Journal of General Chemistry,2015,vol. 85,p. 1870 - 1875
Zh. Obshch. Khim.,2015,vol. 85,p. 1313 - 1318,6

30
[ 1660-94-2 ]
[ 13246-46-3 ]
C₂₆H₂₉O₅P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In water; at 50 - 100℃; for 24h;Alkaline conditions;	The diphosphonate B (15.6 g, 0.054 mol) and sodium carbonate (9 g, 0.065 mol) are stirred in 10 ml of water. The mixture is heated to a nominal temperature of 50C. After dissolution, the benzyl derivative is added (6.9 g, 0.022 mol) and the reaction mixture is heated at a nominal temperature of 100C for 24 hours. After cooling, a large volume of water is added and the mixture is then extracted twice with dichloromethane. The organic phases are combined and then concentrated to dryness. After triturating the crude product in a small volume of water, the solid is washed with diisopropyl ether. Product C is obtained after filtration in the form of a beige-coloured powder in a yield of 81%.

Reference： [1]Patent: WO2018/210933,2018,A1 .Location in patent: Page/Page column 15-17

31
[ 13246-46-3 ]
[ 756-79-6 ]
C₂₄H₂₇O₆P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%		2.5 ml of BuLi (24 ml, 60 mmol) was added slowly to a solution of dimethyl methylphosphonate (6.2 g, 50 mmol) in 200 ml of anhydrous THF at -78C under nitrogen. The mixture was stirred at -78C for 1 hour. A solution of B (19.1 g, 60 mmol) in anhydrous THF was then added dropwise at -78C. The resulting mixture was allowed to warm to room temperature with stirring for 3 hours. The reaction was quenched by addition of aqueous NH4C1 solution and extracted three times with ethyl acetate. The combined extracts were successively washed with brine, dried over sodium sulfate and evaporated. The resulting residue was purified by chromatography on silica gel (eluent: 1/2 petroleum ether/ethyl acetate) to give 15.7 g of (a") in the form of a white solid in a yield of 71%.

Reference： [1]Patent: WO2018/210933,2018,A1 .Location in patent: Page/Page column 20; 21

32
[ 2404-73-1 ]
[ 13246-46-3 ]
C₃₀H₃₉O₆P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		5.0 mL of 2.5 M n-BuLi in THF were added to a solution of compound (A) (2.44 g, 11.7 mmol) in 20 ml of THF at -78C. After stirring for 30 minutes, a solution of compound B (4.48 g, 14.1 mmol) in 30 ml of THF was added. The reaction mixture was gradually warmed to room temperature and stirred for 3 hours. The reaction was quenched by adding 200 ml of saturated NH4C1 and extracted three times with EtOAc. The combined organic phases were washed with water and then concentrated to dryness under vacuum. The crude product was purified by chromatography on a column of silica gel, eluting with 5/1 PE/EtOAc to give 4.7 g of compound (c) in the form of a white solid in a yield of 76%.

Reference： [1]Patent: WO2018/210933,2018,A1 .Location in patent: Page/Page column 17; 18

33
[ 77304-63-3 ]
[ 13246-46-3 ]
C₃₄H₄₇O₆P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%		6.5 mL of 2.5 M n-BuLi in THF were added to a solution of (a') (3.6 g, 13.6 mmol) in 40 ml of THF at -78C. After stirring for 30 minutes, a solution of B (5.2 g, 16.3 mmol) in 30 ml of THF was added. The reaction mixture was gradually warmed to room temperature and stirred for 3 hours. The reaction was quenched by addition of 400 ml of saturated NH4C1 and extracted three times with EtOAc. The combined organic layers were washed with water and then concentrated to dryness under vacuum. The crude product was further purified by chromatography on a column of silica gel, eluting with 5/1 PE/EtOAc to give 5.9 g of intermediate (c') in the form of a white solid in a yield of 75%.

Reference： [1]Patent: WO2018/210933,2018,A1 .Location in patent: Page/Page column 19; 20

34
[ 13246-46-3 ]
C₅H₁₁O₃P [ No CAS ]
C₂₆H₂₉O₆P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20.5%		9.0 mL of 2.5 M n-BuLi in THF were added to a solution of (b'") (3.0 g, 20.0 mmol) in 40 ml of THF at -78C. After stirring for 30 minutes, a solution of B (7.0 g, 22.0 mmol) in 30 ml of THF was added. The reaction mixture was gradually warmed to room temperature and stirred for 3 hours. The reaction was quenched by addition of 200 ml of saturated NH4C1 and extracted three times with EtOAc. The combined organic layers were washed with water and then concentrated to dryness under vacuum. The crude product was purified by chromatography on a column of silica gel, eluting with 5/1 PE/EtOAc to give 1.92 g of (c'") in the form of a white solid in a yield of 20.5%.

Reference： [1]Patent: WO2018/210933,2018,A1 .Location in patent: Page/Page column 22-24

35
[ 873-97-2 ]
[ 13246-46-3 ]
C₂₇H₃₁O₆P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%		5.2 mL of 2.5 M n-BuLi in THF were added to a solution of 3 (2.0 g, 12.2 mmol) in 50 ml of THF at -78C. After stirring for 30 minutes, a solution of compound B (3.88 g, 12.2 mmol) in 20 ml of THF was added. The reaction mixture was gradually warmed to room temperature and stirred for 3 hours. The core was quenched by adding 200 ml of saturated NH4C1 and extracted three times with EtOAc. The combined organic phases were washed with water and then concentrated to dryness under vacuum. The crude product was further purified by chromatography on a column of silica gel, eluting with 100/2 CH2C12/CH30H to give 5.18 g of c-4 in the form of a white solid in a yield of 71%.

Reference： [1]Patent: WO2018/210933,2018,A1 .Location in patent: Page/Page column 24-26

36
[ 13246-46-3 ]
[ 35026-66-5 ]
C₂₆H₂₉O₆P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%		9.0 ml of 2.5 M n-BuLi in THF were added to a solution of b-5 (3.0 g, 20.0 mmol) in 40 ml of THF at -78C. After stirring for 30 minutes, a solution of compound 2 (7.0 g, 22.0 mmol) in 30 ml of THF was added. The reaction mixture was gradually warmed to room temperature and stirred for 3 hours. The reaction was quenched by adding 200 ml of saturated NH4C1 and extracted three times with EtOAc. The combined organic phases were washed with water and then concentrated to dryness under vacuum. The crude product was purified by chromatography on a column of silica gel, eluting with 5/1 PE/EtOAc to give 3.75 g of c-5 in the form of a white solid in a yield of 40%.

Reference： [1]Patent: WO2018/210933,2018,A1 .Location in patent: Page/Page column 26-28

37
[ 13246-46-3 ]
C₈H₁₇O₃P [ No CAS ]
C₂₉H₃₅O₆P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37.7%		4.2 ml of 2.5 M n-BuLi in THF was added to a solution of b-6 (2.0 g, 10.4 mmol) in 40 ml of THF at -78C. After stirring for 30 minutes, a solution of 2 (3.3 g, 10.4 mmol) in 30 ml of THF was added. The reaction mixture was gradually warmed to room temperature and stirred for 3 hours. The reaction was quenched by adding 200 ml of saturated NH4C1 and extracted three times with EtOAc. The combined organic phases were washed with water and then concentrated to dryness under vacuum. The crude product was further purified by chromatography on a column of silica gel, eluting with 5/1 PE/EtOAc to give 2.0 g of c-6 in the form of a white solid in a yield of 37.7%.

Reference： [1]Patent: WO2018/210933,2018,A1 .Location in patent: Page/Page column 28-30

38
[ 3581-87-1 ]
[ 13246-46-3 ]
C₂₅H₂₃NO₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%		To a solution of compound 3 (1.98 g, 20.0 mmol) in 60 ml of THF are added 10.0 ml of 2.0 M LDA in THF at -78C. After stirring for 30 minutes, a solution of compound 2 (6.36 g, 20.0 mmol) in 30 ml of THF is added. The reaction mixture is gradually warmed to room temperature and stirred for 2 hours. The reaction is quenched by adding 400 ml of saturated NH4C1 and extracted three times with EtOAc. The combined organic phases are washed with water and then concentrated to dryness under vacuum. The crude product is then purified by chromatography on a column of silica gel, eluting with 5/1 PE/EtOAc to give 5.5 g of compound 4 in the form of a white solid in a yield of 66%.

Reference： [1]Patent: WO2019/63710,2019,A1 .Location in patent: Page/Page column 19

39
[ 13246-46-3 ]
[ 67093-27-0 ]
[ 4721-07-7 ]

Reference： [1]Patent: CN109970517,2019,A

40
[ 13246-46-3 ]
[ 67093-27-0 ]
C₄₂H₃₆O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium carbon (20 wt%); In toluene; at 60℃; for 9h;	67.7 g of 3,5-dibenzyloxybenzyl chloride, 63.6 g of <strong>[13246-46-3]2,4-dibenzyloxybenzaldehyde</strong>,0.64 g 20wt%Palladium carbon catalyst mixed with 400 grams of toluene,Heat toAfter reacting at 60 C for 9 hours,WillThe reaction solution is cooled to below 25 C;Inside the reaction vesselThe gas is replaced by hydrogen and then hydrogen is introduced to a pressure of 15 kg·f/cm 2 .Then warm to 80 C,Continue to react for 12 hours;The obtained reaction liquid is filtered to recover the catalyst.The filtrate is evaporated to dryness.The solid obtained by evaporation to dryness was heated to 80 C with 50 g of toluene to dissolve.Then cooled to 15 C and filtered to dry.Got 40.1Oxidized resveratrol,The yield is 82.2%,The purity was 99.8% by liquid chromatography

Reference： [1]Patent: CN109970517,2019,A .Location in patent: Paragraph 0061; 0062

41
[ 23428-77-5 ]
[ 13246-46-3 ]
C₃₇H₃₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In ethanol; for 12h;Reflux;	One eq 16A and one eq 16B were dissolved in ethanol and 0.5 eqpotassium hydroxide was added at room temperature. During refluxing for 12 h, precipitation couldalready be observed. Ethanol/H2O (1:1, v/v) was added and the mixture was vacuum filtered. Theprecipitate was washed 4 times with Ethanol/H2O (1:1, v/v) and dried at 70 C. One eq of precipitatewas then dissolved in anhydrous tetrahydrofuran, cooled to 10 C under inert gas, and 0.5 eq of lithiumaluminium hydride dissolved in tetrahydrofuran was added dropwise, while keeping the reactiontemperature under 20 C. After stirring for 3 h at room temperature, the reaction mixture was thenagain cooled to 0 C, and the reaction was quenched by adding H2O and sodium hydroxide solution(15%, v/w). After the addition of sodium sulfate, the mixture was stirred for another half hour. Thereaction mixture was filtered and the filtrate was evaporated to dryness.

Reference： [1]Molecules,2020,vol. 25

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
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.
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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

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

[ CAS No. 13246-46-3 ]

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Application In Synthesis of [ 13246-46-3 ]

[ 13246-46-3 ] Synthesis Path-Upstream 1~2

[ 13246-46-3 ] Synthesis Path-Downstream 1~41

Related Functional Groups of [ 13246-46-3 ]

Aryls

Aldehydes

Ethers

Precautionary Statements-General

Prevention

Response

Storage

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[ 13246-46-3 ]