[ CAS No. 3328-70-9 ] {[proInfo.proName]}

Name: 3328-70-9|4-Hydroxyisophthalaldehyde|98%
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Quality Control of [ 3328-70-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 3328-70-9 ]

Product Details of [ 3328-70-9 ]

CAS No. :	3328-70-9	MDL No. :	MFCD00003334
Formula :	C₈H₆O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FEUATHOQKVGPEK-UHFFFAOYSA-N
M.W :	150.13	Pubchem ID :	165106
Synonyms :

Calculated chemistry of [ 3328-70-9 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	39.24
TPSA :	54.37 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.96 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.65
Log Po/w (XLOGP3) :	0.36
Log Po/w (WLOGP) :	1.02
Log Po/w (MLOGP) :	0.15
Log Po/w (SILICOS-IT) :	1.65
Consensus Log Po/w :	0.77

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.27
Solubility :	8.08 mg/ml ; 0.0538 mol/l
Class :	Very soluble
Log S (Ali) :	-1.07
Solubility :	12.9 mg/ml ; 0.0858 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.7
Solubility :	2.99 mg/ml ; 0.0199 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 3328-70-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 3328-70-9 ]

* 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 [ 3328-70-9 ]
Downstream synthetic route of [ 3328-70-9 ]

[ 3328-70-9 ] Synthesis Path-Upstream 1~3

1
[ 100-97-0 ]
[ 90-02-8 ]
[ 3328-69-6 ]
[ 3328-70-9 ]

Yield	Reaction Conditions	Operation in experiment
10.5%	Stage #1: With copper(I) oxide In trifluoroacetic acid for 5 h; Reflux Stage #2: With hydrogenchloride In water at 20℃; for 1 h;	General procedure: To a solution of substrates (1a–1q, 0.15 mmol) in trifluoroacetic acid (5 ml), hexamethylenetetramine (0.3 mmol) and cuprous oxide (0.15 mmol) were added. The reaction mixture was refluxed for about 5 h, cooled to room temperature, followed by addition of hydrochloric acid (3 N, 5 ml). After stirring for another 1 h, the solution was concentrated under reduced pressure. The products were purified by silica gel column chromatography (200–300 mesh).

Reference： [1] Research on Chemical Intermediates, 2015, vol. 41, # 11, p. 8147 - 8158

2
[ 67-66-3 ]
[ 108-95-2 ]
[ 3328-69-6 ]
[ 3328-70-9 ]
[ 123-08-0 ]
[ 90-02-8 ]

Reference： [1] Synthetic Communications, 1988, vol. 18, # 16-17, p. 2095 - 2102

3
[ 3328-70-9 ]
[ 70-11-1 ]
[ 120973-72-0 ]

Reference： [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 18, p. 4405 - 4418
[2] Tetrahedron Letters, 1996, vol. 37, # 52, p. 9267 - 9270
[3] Tetrahedron Letters, 1996, vol. 37, # 52, p. 9267 - 9270
[4] Heterocycles, 1997, vol. 45, # 7, p. 1363 - 1384
[5] Patent: EP299620, 1989, A1,

[ 3328-70-9 ] Synthesis Path-Downstream 1~65

1
[ 23731-06-8 ]
[ 3328-70-9 ]

Yield	Reaction Conditions	Operation in experiment
60.1%		14.82 g (0.11 mol, 2 eq) of urotropine was dissolved in 90 mL of acetic acid, and 9 g (0.053 mol, 1 eq) of compound 4 was added to the mixture until completely dissolved.The reaction was carried out at 115 C for 1 h. Further, 90 mL of concentrated hydrochloric acid was added dropwise to the mixture and reacted at 115 C for 1 h. After cooling to room temperature, an appropriate amount of carbon dichloride was added and washed twice with saturated brine. Drying with anhydrous magnesium sulfate, suction filtration, spin-drying, and purification of the crude product by silica gel column chromatography.The dichloromethane/methanol system was used as the eluent. Yield 10.88 g of a white solid as product 5 in 60.1% yield.
56%	With hydrogenchloride; hexamethylenetetramine; acetic acid; for 1.08333h;Reflux;	Add 15 mL of 50% acetic acid solution to a 100 mL round bottom flask.Compound 5 (0.85 g, 5 mmol) and hexamethylenetetramine (0.91 g, 6.5 mmol) were added to the reaction flask.The reaction system was heated to reflux for 1 hour, then 3 mL of concentrated hydrochloric acid was added to the reaction flask and reflux was continued for 5 minutes.After the reaction system was cooled, the reaction mixture was poured into ice water toield of pale yellow solid compound intermediate 7 (0.42 g, 56%).
4.41 g	With hydrogenchloride; hexamethylenetetramine; acetic acid; In water; for 2h;Reflux;	A solution of acetic acid (22 ml, 50%) and hexamethylenetetramine (4.0 g) was reflexed at the progress of heating until the solid in these mixture completely dissolved and then recovered to room temperature. Added b (3.80 g, 22 mmol) and concentrated hydrochloric acid (50 mL) to the solution and refluxed it about 2 hours. Stop this reaction and put the reaction flask in refrigerator to gain pale yellow precipitate. These precipitate needed to be washed by water and finally dried and we gained c (4.41g). m.p = 106-108 C. 1H NMR (600 MHz, d6-DMSO) delta 11.76 (s, 1H), 10.32 (s, 1H), 9.87 (s, 1H), 8.19 (d, J = 2.2 Hz, 1H), 8.00 (dd, J = 8.6, 2.2 Hz, 1H), 7.15 (d, J = 8.6 Hz, 1H). 13C NMR (151 MHz, d6-DMSO) delta 191.49, 190.48, 165.87, 136.11, 132.43, 128.81, 122.99.

		In a solution containing 13 mL of 50% acetic acid, 12.5 mmol of product 1 and 16.2 mmol of hexamethylenetetramine were added, respectively, heated to 120 C. The reaction solution was refluxed. After 1 hour, 6 mL of concentrated hydrochloric acid was added and the solution became yellow. The mixture was stirred for 5 minutes. After the ice bath was added, the crude product was precipitated, filtered and dried in vacuo to give a pale yellow product.
66 g	With hexamethylenetetramine; acetic acid; In water; for 1h;Reflux;	A mixture of salicylaldehyde (60g, 0.39mol) and paraformaldehyde (24.2g, 0.64mol) in concentrated hydrochloric acid (390ml) was stirred at room temperature for 1h and then POCl3 (20ml) was added dropwise at 0-10C, large amounts of solids gradually precipitated. After completion of addition, the mixture was stirred at room temperature for another 8h. The solid was separated by filtration as a white powder and dried under vacuum at 40C. The above product was added to a solution of HMTA (74.7g, 0.53mol), H2O (140mL), CH3COOH (140mL) and refluxed for 1h. After completion of the reaction, 140ml of concentrated hydrochloric acid was added and refluxed for 10min. Then, the mixture was poured into ice water and stirred for 30min. The solid was separated by filtration as a yellow powder (66g) in 89.5% yield which was used directly in the next step.

Reference： [1]Applied Organometallic Chemistry,2010,vol. 24,p. 86 - 91
[2]Patent: CN109096170,2018,A .Location in patent: Paragraph 0123; 0136-0138
[3]Chemical Communications,2019,vol. 55,p. 14930 - 14933
[4]Patent: CN110372742,2019,A .Location in patent: Paragraph 0014; 0027; 0029
[5]Journal of the Chemical Society,1950,p. 2114,2142
[6]New Journal of Chemistry,2015,vol. 39,p. 4162 - 4167
[7]Tetrahedron,2017,vol. 73,p. 2938 - 2942
[8]Phosphorus, Sulfur and Silicon and the Related Elements,2017,vol. 192,p. 565 - 569
[9]Patent: CN105038766,2017,B .Location in patent: Paragraph 0018; 0048; 0059; 0069; 0080
[10]European Journal of Medicinal Chemistry,2019,vol. 181

2
[ 67-66-3 ]
[ 108-95-2 ]
[ 3328-69-6 ]
[ 3328-70-9 ]
[ 123-08-0 ]
[ 90-02-8 ]

Reference： [1]Synthetic Communications,1988,vol. 18,p. 2095 - 2102

3
[ 118-12-7 ]
[ 3328-70-9 ]
[ 20200-69-5 ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 3915 - 3917
[2]Russian Journal of Bioorganic Chemistry,2008,vol. 34,p. 252 - 260
[3]Russian Chemical Bulletin,2014,vol. 63,p. 2026 - 2035
Izv. Akad. Nauk, Ser. Khim.,2014,p. 2026 - 2035,10
[4]Tetrahedron,1996,vol. 52,p. 8755 - 8762
[5]Chemical Communications,2002,p. 1398 - 1399

4
[ 100-97-0 ]
[ 123-08-0 ]
[ 3328-70-9 ]

Yield	Reaction Conditions	Operation in experiment
66%	With trifluoroacetic acid; at 90℃; for 24h;	P-hydroxybenzaldehyde (1.2 g, 10 mmol) was dissolved in 10 mL of trifluoroacetic acid.Add urotropine (1.4 g, 10 mmol),After heating to 90 C for 24 hours, add 14 mL of concentrated hydrochloric acid.After the reaction was cooled to room temperature, the solvent was evaporated under reduced pressure.Recrystallization from cold ethanol (about -5 C) gives 1.0 g of a white solid, which is compound 1(Yield, 66%).

Reference： [1]Patent: CN109206351,2019,A .Location in patent: Paragraph 0018; 0019
[2]Heterocycles,1997,vol. 45,p. 1363 - 1384
[3]Tetrahedron Letters,1996,vol. 37,p. 9267 - 9270
[4]Chemical Communications,2007,p. 4686 - 4688

5
[ 3328-70-9 ]
[ 70-11-1 ]
[ 120973-72-0 ]

Yield	Reaction Conditions	Operation in experiment
		Example X2 2-Benzoyl-5-formylbenzofuran This compound was prepared from 5-formylsalicylaldehyde and alpha-bromoacetophenone by a method analogous to that used in Example X1.

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4405 - 4418
[2]Tetrahedron Letters,1996,vol. 37,p. 9267 - 9270
[3]Tetrahedron Letters,1996,vol. 37,p. 9267 - 9270
[4]Patent: EP299620,1989,A1

6
[ 269060-13-1 ]
[ 3328-70-9 ]

Reference： [1]Synthetic Communications,2000,vol. 30,p. 1003 - 1008

7
[ 3328-70-9 ]
potash [ No CAS ]
[ 636-46-4 ]

Reference： [1]Chemische Berichte,1882,vol. 15,p. 2025

8
[ 20200-69-5 ]
[ 3328-70-9 ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 3915 - 3917

9
[ 3328-70-9 ]
5,10-dimesityl-21-oxatripyrrane [ No CAS ]
C₄₀H₃₄N₂O₂ [ No CAS ]

Reference： [1]Chemical Communications,2002,p. 462 - 463

10
[ 37595-74-7 ]
[ 3328-70-9 ]
trifluoro-methanesulfonic acid 2,4-diformyl-phenyl ester [ No CAS ]

Reference： [1]Organic Letters,2002,vol. 4,p. 1231 - 1233

11
[ 3328-70-9 ]
4-dodecyloxy-5-methoxy-2-nitrobenzyl bromide [ No CAS ]
[ 760984-01-8 ]

Reference： [1]Tetrahedron,2004,vol. 60,p. 7261 - 7266

12
[ 3328-70-9 ]
[ 500003-14-5 ]
9,18-diethyl-8,19-dimethyl-24-oxa-2-oxybenziporphyrin hydrochloride [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 6079 - 6093

13
[ 25597-16-4 ]
[ 3328-70-9 ]
[ 215124-06-4 ]

Yield	Reaction Conditions	Operation in experiment
24%	With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 60 - 75℃; for 28h;	[0451] A 50 mL round bottom flask was charged with 5-FORMYLSALICYLALDEHYDE (3.21 g, 21.39 mmol), ethyl 4,4, 4-trifluorocrotonate (3.50 mL, 3.96 g, 23.53 MMOL), DIMETHYLFORMAMIDE (15 mL) and potassium carbonate (2.95 g, 21.39 mmol) and heated to 60 C for 12 hours. Additional ethyl 4,4, 4-trifluorocrotonate (3.50 mL, 3.96 g, 23.53 mmol) was added and the reaction heated for 16 hours at 75 C. After cooling to room temperature, the reaction was partitioned between H20 and diethyl ether. The organic phase was washed with saturated NAHC03 solution, KHS04 solution (0.25 M), brine, treated with decolorizing carbon (warming gently). The resulting black suspension was dried over MgS04, vacuum filtered through diatomaceous earth, and concentrated in vacuo yielding an orange crystalline mass. This material was recrystallized from hot hexanes yielding the ester (1.51 g, 24 %) as orange crystals: mp 84.3-86. 2 C. 1H NMR (acetone-d6/300 MHz) 9.96 (s, 1H), 8.06 (d, 1H, J= 2Hz), 8.02 (s, 1H), 7.99 (dd, 1H, J= 8.5, 2. 0HZ), 7.24 (d, 1H, J= 8.5 Hz), 5.99 (q, 1H, J= 7.1 Hz), 4.43-4. 25 (m, 2H), 1.34 (t, 3H, J= 7.3 Hz). FABLRMS ONLY 301 (M+H). EIHRMS M/Z 300.0605 (M+, CALC D 300.0609). Anal. Calc'd for C14H11F3O4: C, 56.01 ; H, 3.69. Found: C, 56.11 ; H, 3.73.

Reference： [1]Patent: WO2004/87686,2004,A2 .Location in patent: Page 218-219
[2]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 7164 - 7168

14
[ 3328-70-9 ]
[ 1972-28-7 ]
2-(3,5-di-t-butyl-4-hydroxyphenyl)-4-(2-(2,4-bis-formylphenoxy)-ethyl)oxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.3 g (49%)	With triphenylphosphine; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;	A. Preparation of 2-(3,5-di-t-butyl-4-hydroxyphenyl)-4-(2-(2,4-bis-formylphenoxy) ethyl)oxazole In a flask, 4.75 g (15 mmole) of the compound of Example 1 C, 2.36 g (15.75 mmole) of <strong>[3328-70-9]3-formyl-4-hydroxybenzaldehyde</strong>, and 3.93 g (15 mmole) of triphenylphosphine were dissolved in 45 ml tetrahydrofuran with stirring, under nitrogen. The solution was chilled to -10 and a solution of 2.36 ml (15 mmole) diethyl azodicarboxylate in 15 ml. Tetrahydrofuran was added over 10 minutes, with stirring. The reaction exothermed to +1 C. The bath was removed and the reaction stirred under nitrogen for 18 hours. The reaction was then stripped, dissolved in a minimum amount of methylene chloride and placed in the freezer. The diethoxycarbonylhydrazine was then filtered off and the filtrate was chromatographed, Prep 500, two columns, eluding with 0 to 20% ethyl acetate/toluene gradient over 30 minutes. The appropriate fractions were bulked and stripped to give 3.3 g (49%) product which was used without further purification. NMR (CDCl3), delta1.48 (s, 18 H), 3.17 (t, 2 H, J=7 Hz), 4.53 (t, 2 H, J=5 Hz), 5.52 (s, 1 H), 7.19 (d, 1 H, 9 Hz), 7.53 (s, 1 H), 7.84 (s, 2 H), 8.11 (dd, 1 H, J=2 Hz,9 Hz), 8.32 (d, 1 H, J=2 Hz), 9.94 (s, 1 H), 10.48 (s, 1 H)
3.3 g (49%)	With triphenylphosphine; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;	A. Preparation of 2-(3,5-di-t-butyl-4-hydroxyphenyl)-4-(2-(2,4-bis-formylphenoxy)ethyl)oxazole In a flask, 4.75 g (15 mmole) of the compound of Example 1 C, 2.36 g (15.75 mmole) of <strong>[3328-70-9]3-formyl-4-hydroxybenzaldehyde</strong>, and 3.93 g (15 mmole) of triphenylphosphine were dissolved in 45 ml tetrahydrofuran with stirring, under nitrogen. The solution was chilled to -10 and a solution of 2.36 ml (15 mmole) diethylazodicarboxylate in 15 ml. Tetrahydrofuran was added over 10 minutes, with stirring. The reaction exothermed to +1 C. The bath was removed and the reaction stirred under nitrogen for 18 hours. The reaction was then stripped, dissolved in a minimum amount of methylene chloride and placed in the freezer. The diethoxycarbonylhydrazine was then filtered off and the filtrate was chromatographed, Prep 500, two columns, eluding with 0 to 20% ethyl acetate/toluene gradient over 30 minutes. The appropriate fractions were bulked and stripped to give 3.3 g (49%) product which was used without further purification. NMR (CDCl3), delta 1.48 (s, 18H), 3.17 (t, 2H, J=7 Hz), 4.53 (t, 2H, J=5 Hz), 5.52 (s, 1H), 7.19 (d, 1H, 9 Hz), 7.53 (s, 1H), 7.84 (s, 2H), 8.11 (dd, 1H, J=2 Hz,9 Hz), 8.32 (d, 1H, J=2 Hz), 9.94 (s, 1H), 10.48 (s, 1H)
3.3 g (49%)	With triphenylphosphine; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;	A. Preparation of 2-(3,5-di-t-butyl-4-hydroxyphenyl)-4-(2-(2,4-bis-formylphenoxy)ethyl)oxazole In a flask, 4.75 g (15 mmole) of the compound of Example 1 C, 2.36 g (15.75 mmole) of <strong>[3328-70-9]3-formyl-4-hydroxybenzaldehyde</strong>, and 3.93 g (15 mmole) of triphenylphosphine were dissolved in 45 ml tetrahydrofuran with stirring, under nitrogen. The solution was chilled to -10 and a solution of 2.36 ml (15 mmole) diethyl azodicarboxylate in 15 ml. Tetrahydrofuran was added over 10 minutes, with stirring. The reaction exothermed to +1 C. The bath was removed and the reaction stirred under nitrogen for 18 hours. The reaction was then stripped, dissolved in a minimum amount of methylene chloride and placed in the freezer. The diethoxycarbonylhydrazine was then filtered off and the filtrate was chromatographed, Prep 500, two columns, eluding with 0 to 20% ethyl acetate/toluene gradient over 30 minutes. The appropriate fractions were bulked and stripped to give 3.3 g (49%) product which was used without further purification. NMR (CDCl3), delta1.48 (s, 18H), 3.17 (t, 2H, J=7 Hz), 4.53 (t, 2H, J=5 Hz), 5.52 (s, 1H), 7.19 (d, 1H, 9 Hz), 7.53 (s, 1H), 7.84 (s, 2H), 8.11 (dd, 1H, J=2 Hz,9 Hz), 8.32 (d, 1H, J=2 Hz), 9.94 (s, 1H), 10.48 (s, 1H)

3.3g (49%)	With triphenylphosphine; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;	A. Preparation of 2-(3,5-di-t-butyl-4-hydroxyphenyl)-4-(2-(2,4-bis-formylphenoxy)ethyl)oxazole In a flask, 4.75g (15 mmole) of the compound of Example 1 C, 2.36g (15.75 mmole) of <strong>[3328-70-9]3-formyl-4-hydroxybenzaldehyde</strong>, and 3.93 g (15 mmole) of triphenylphosphine were dissolved in 45 ml tetrahydrofuran with stirring, under nitrogen. The solution was chilled to -10 and a solution of 2.36 ml (15 mmole) diethylazodicarboxylate in 15 ml. Tetrahydrofuran was added over 10 minutes, with stirring. The reaction exothermed to +1C. The bath was removed and the reaction stirred under nitrogen for 18 hours. The reaction was then stripped, dissolved in a minimum amount of methylene chloride and placed in the freezer. The diethoxycarbonylhydrazine was then filtered off and the filtrate was chromatographed, Prep 500, two columns, eluding with 0 to 20% ethyl acetate/toluene gradient over 30 minutes. The appropriate fractions were bulked and stripped to give 3.3g (49%) product which was used without further purification. NMR (CDCl3), delta 1.48 (s, 18H), 3.17 (t, 2H, J=7Hz), 4.53 (t, 2H, J=5Hz), 5.52 (s, 1H), 7.19 (d, 1H, 9Hz), 7.53 (s, 1H), 7.84 (s, 2H), 8.11 (dd, 1H, J=2Hz,9Hz), 8.32 (d, 1H, J=2Hz), 9.94 (s, 1H), 10.48 (s, 1H)
3.3g (49%)	With triphenylphosphine; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;	A. Preparation of 2-(3,5-di-t-butyl-4-hydroxyphenyl)-4-(2-(2,4-bis-formylphenoxy)ethyl)oxazole In a flask, 4.75g (15 mmole) of the compound of Example 1 C, 2.36g (15.75 mmole) of <strong>[3328-70-9]3-formyl-4-hydroxybenzaldehyde</strong>, and 3.93 g (15 mmole) of triphenylphosphine were dissolved in 45 ml tetrahydrofuran with stirring, under nitrogen. The solution was chilled to -10 and a solution of 2.36 ml (15 mmole) diethylazodicarboxylate in 15 ml. Tetrahydrofuran was added over 10 minutes, with stirring. The reaction exothermed to +1C. The bath was removed and the reaction stirred under nitrogen for 18 hours. The reaction was then stripped, dissolved in a minimum amount of methylene chloride and placed in the freezer. The diethoxycarbonylhydrazine was then filtered off and the filtrate was chromatographed, Prep 500, two columns, eluding with O to 20% ethyl acetate/toluene gradient over 30 minutes. The appropriate fractions were bulked and stripped to give 3.3g (49%) product which was used without further purification. NMR (CDCl3), delta 1.48 (s, 18H), 3.17 (t, 2H, J=7Hz), 4.53 (t, 2H, J=5Hz), 5.52 (s, 1H), 7.19 (d, 1H, 9Hz), 7.53 (s, 1H), 7.84 (s, 2H), 8.11 (dd, 1H, J=2Hz,9Hz), 8.32 (d, 1H, J=2Hz), 9.94 (s, 1H), 10.48 (s, 1H)
3.3g (49%)	With triphenylphosphine; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;	A. Preparation of 2-(3,5-di-t-butyl-4-hydroxyphenyl)-4-(2-(2,4-bis-formylphenoxy)ethyl)oxazole In a flask, 4.75g (15 mmole) of the compound of Example 1 C, 2.36g (15.75 mmole) of <strong>[3328-70-9]3-formyl-4-hydroxybenzaldehyde</strong>, and 3.93 g (15 mmole) of triphenylphosphine were dissolved in 45 ml tetrahydrofuran with stirring, under nitrogen. The solution was chilled to -10 and a solution of 2.36 ml (15 mmole) diethylazodicarboxylate in 15 ml. Tetrahydrofuran was added over 10 minutes, with stirring. The reaction exothermed to +1C. The bath was removed and the reaction stirred under nitrogen for 18 hours. The reaction was then stripped, dissolved in a minimum amount of methylene chloride and placed in the freezer. The diethoxycarbonylhydrazine was then filtered off and the filtrate was chromatographed, Prep 500, two columns, eluding with 0 to 20% ethyl acetate/toluene gradient over 30 minutes. The appropriate fractions were bulked and stripped to give 3.3g (49%) product which was used without further purification. NMR (CDCl3), delta 1.48 (s, 18H), 3.17 (t, 2H, J=7Hz), 4.53 (t, 2H, J=5Hz), 5.52 (s, 1H), 7.19 (d, 1H, 9Hz), 7.53 (s, 1H), 7.84 (s, 2H), 8.11 (dd, 1H, J=2Hz,9Hz), 8.32 (d, 1H, J=2Hz), 9.94 (s, 1H), 10.48 (s, 1H)

Reference： [1]Patent: US2001/27194,2001,A1
[2]Patent: US5952360,1999,A
[3]Patent: US6156748,2000,A
[4]Patent: EP906755,1999,A2
[5]Patent: EP908186,1999,A2
[6]Patent: EP908180,1999,A2

15
[ 25597-16-4 ]
[ 3328-70-9 ]
[ 7440-44-0 ]
[ 215124-06-4 ]

Yield	Reaction Conditions	Operation in experiment
24%	With potassium carbonate; In N-methyl-acetamide;	Step 1. Preparation of ethyl 6-formyl-2-(trifluoromethyl)-2H-1-benzopyran-3-carboxylate A 50 mL round bottom flask was charged with 5-formylsalicylaldehyde (3.21 g, 21.39 mmol), ethyl 4,4,4-trifluorocrotonate (3.50 mL, 3.96 g, 23.53 mmol), dimethylformamide (15 mL) and potassium carbonate (2.95 g, 21.39 mmol) and heated to 60 C. for 12 hours. Additional ethyl 4,4,4-trifluorocrotonate (3.50 mL, 3.96 g, 23.53 mmol) was added and the reaction heated for 16 hours at 75 C. After cooling to room temperature, the reaction was partitioned between H2O and diethyl ether. The organic phase was washed with saturated NaHCO3 solution, KHSO4 solution (0.25 M), brine, treated with decolorizing carbon (warmed gently). The resulting black suspension was dried over MgSO4, vacuum filtered through diatomaceous earth, and concentrated in vacuo yielding an orange crystalline mass. This material was recrystallized from hot hexanes yielding the ester (1.51 g, 24%) as orange crystals: mp 84.3-86.2 C. 1H NMR (acetone-d6/300 MHz) 9.96 (s, 1H), 8.06 (d, 1H, J=2 Hz), 8.02 (s, 1H), 7.99 (dd, 1H, J=8.5, 2.0 Hz), 7.24 (d, 1H, J=8.5 Hz), 5.99 (q, 1H, J=7.1 Hz), 4.43-4.25 (m, 2H), 1.34 (t, 3H, J=7.3 Hz). FABLRMS m/z 301 (M+H). EIHRMS m/z 300.0605 (M+, Calc'd 300.0609). Anal. Calc'd for C14H11F3O4: C, 56.01; H, 3.69. Found: C, 56.11; H, 3.73.
24%	With potassium carbonate; In N-methyl-acetamide;	EXAMPLE 75 STR97 Step 1. Preparation of ethyl 6-formyl-2-(trifluoromethyl)-2H-1-benzopyran-3-carboxylate. A 50 mL round bottom flask was charged with 5-formylsalicylaldehyde (3.21 g, 21.39 mmol), ethyl 4,4,4-trifluorocrotonate (3.50 mL, 3.96 g, 23.53 mmol), dimethylformamide (15 mL) and potassium carbonate (2.95 g, 21.39 mmol) and heated to 60 C. for 12 hours. Additional ethyl 4,4,4-trifluorocrotonate (3.50 mL, 3.96 g, 23.53 mmol) was added and the reaction heated for 16 hours at 75 C. After cooling to room temperature, the reaction was partitioned between H2 O and diethyl ether. The organic phase was washed with saturated NaHCO3 solution, KHSO4 solution (0.25 M), brine, treated with decolorizing carbon (warmed gently). The resulting black suspension was dried over MgSO4, vacuum filtered through diatomaceous earth, and concentrated in vacuo yielding an orange crystalline mass. This material was recrystallized from hot hexanes yielding the ester (1.51 g, 24%) as orange crystals: mp 84.3-86.2 C. 1 H NMR (acetone-d6 /300 MHz) 9.96 (s, 1H), 8.06 (d, 1H, J=2Hz), 8.02 (s, 1H), 7.99 (dd, 1H, J=8.5, 2.0Hz), 7.24 (d, 1H, J=8.5 Hz), 5.99 (q, 1H, J=7.1 Hz), 4.43-4.25 (m, 2H), 1.34 (t, 3H, J=7.3 Hz). FABLRMS m/z 301 (M+H). EIHRMS m/z 300.0605 (M+, Calc'd 300.0609). Anal. Calc'd for C14 H11 F3 O4: C, 56.01; H, 3.69. Found: C, 56.11; H, 3.73.
24%	With potassium carbonate; In N-methyl-acetamide;	Step 1. Preparation of ethyl 6-formyl-2-(trifluoromethyl)-2H-1-benzopyran-3-carboxylate. A 50 mL round bottom flask was charged with 5-formylsalicylaldehyde (3.21 g, 21.39 mmol), ethyl 4,4,4-trifluorocrotonate (3.50 mL, 3.96 g, 23.53 mmol), dimethylformamide (15 mL) and potassium carbonate (2.95 g, 21.39 mmol) and heated to 60 C. for 12 hours. Additional ethyl 4,4,4-trifluorocrotonate (3.50 mL, 3.96 g, 23.53 mmol) was added and the reaction heated for 16 hours at 75 C. After cooling to room temperature, the reaction was partitioned between H2 O and diethyl ether. The organic phase was washed with saturated NaHCO3 solution, KHSO4 solution (0.25 M), brine, treated with decolorizing carbon (warmed gently). The resulting black suspension was dried over MgSO4, vacuum filtered through diatomaceous earth, and concentrated in vacuo yielding an orange crystalline mass. This material was recrystallized from hot hexanes yielding the ester (1.51 g, 24%) as orange crystals: mp 84.3-86.2 C. 1 H NMR (acetone-d6 /300 MHz) 9.96 (s, 1H), 8.06 (d, 1H, J=2 Hz), 8.02 (s, 1H), 7.99 (dd, 1H, J=8.5, 2.0 Hz), 7.24 (d, 1H, J=8.5 Hz), 5.99 (q, 1H, J=7.1 Hz), 4.43-4.25 (m, 2H), 1.34 (t, 3H, J=7.3 Hz). FABLRMS m/z 301 (M+H). EIHRMS m/z 300.0605 (M+, Calc'd 300.0609). Anal. Calc'd for C14 H11 F3 O4: C, 56.01; H, 3.69. Found: C, 56.11; H, 3.73.

Reference： [1]Patent: US2002/103141,2002,A1
[2]Patent: US6034256,2000,A
[3]Patent: US6077850,2000,A

16
[ 3328-70-9 ]
[ 96-32-2 ]
[ 119658-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile;	Synthesis of methyl 5-formylbenzofuran-2-carboxylate K2CO3 (30 g) was added to a solution of 5-formylsalicyl aldehyde (25 g) and methyl bromoacetate (30 g) in acetonitrile (500 ml), and after heated reflux for 24 hours followed by cooling, the reaction solution was filtered and the mother liquor was concentrated under reduced pressure. A saturated ammonium chloride aqueous solution (100 ml) was added to the residue prior to extraction with AcOEt, and the organic layer was dried with MgSO4 and then filtered and concentrated. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=5/1) to obtain methyl 5-formylbenzofuran-2-carboxylate. Yield: 15 g (y. 44%) Mass analysis: [M++H]=205.2

Reference： [1]Patent: US6589984,2003,B1

17
2-(bromomethyl)-4-(tert-butyl)-1,3-thiazol [ No CAS ]
[ 3328-70-9 ]
4-tert-butyl-2-(2,4-diformylphenoxymethyl)thiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium iodide; potassium carbonate; In ethyl acetate; N,N-dimethyl-formamide; toluene;	PREPARATION 3 A mixture of 2-bromomethyl-4-tert-butylthiazole (1.05 g), <strong>[3328-70-9]5-formyl-2-hydroxybenzaldehyde</strong> (0.74 g), potassium carbonate (0.89 g) and potassium iodide (small mass) in N,N-dimethylformamide was stirred at 50 C. for 5 hours. After being cooled, the resulting solution was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to column chromatography on silica gel and eluted with a mixture of toluene and ethyl acetate. The fractions containing object compound were combined and concentrated under reduced pressure to give 4-tert-butyl-2-(2,4-diformylphenoxymethyl)thiazole (1.0 g). mp: 77.5-78.5 C. IR (Nujol): 1695, 1605, 1580 cm-1 NMR (CDCl3, delta): 1.36 (9H, s), 5.58 (2H, s), 6.99 (1H, s), 7.32 (1H, d, J=8.7 Hz), 8.13 (1H, dd, J=8.7 Hz and 2.2 Hz), 8.37 (1H, d, J=2.2 Hz), 9.97 (1H, s), 10.58 (1H, s)

Reference： [1]Patent: US5296495,1994,A

18
[ 1169945-44-1 ]
[ 3328-70-9 ]
[ 1312698-60-4 ]

Yield	Reaction Conditions	Operation in experiment
66%		Synthesis of Compound 6: Compound 2 (50 mg, 0.33 mmol) was dissolved in 1 ml dry DMF and cooled to 0 C. K2C03 (101 mg, 0.73 mmol) was added and the solution stirred at 0 C for 10 minutes, before Compound 5 (229 mg, 0.66 mmol) was added. The reaction mixture was stirred for 12 hours at room temperature and monitored by TLC (EtO Ac/Hex 30:70). After completion, the reaction mixture was diluted with Et20, and was washed with saturated solution of NH4C1. The organic layer was separated, washed with brine, dried over MgS04, and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel (EtO Ac/Hex 30:70) to give Compound 6 (80 mg, 66 %) as a white solid.1H NMR (400MHz, CDC13): delta = 10.55 (IH, s), 9.93 (IH, s), 8.35 (IH, s), 8.07 (IH, d, 8.7 Hz), 7.86 (2H, d, 7.7 Hz), 7.44 (2H, d, 7.7 Hz), 7.17 (IH, d, 8.7 Hz), 5.32 (2H, s), 1.35 (12H, s).13C NMR (400MHz, CDC13): delta =190.81, 189.19, 165.62, 138.68, 136.31, 136.05, 132.59, 130.59, 127.21, 125.90, 114.40, 84.72, 71.74, 25.59.MS (ESI): m/z calc. for C2iH23B05: 366.2 ; found: 389.2 [M+Na]+.
60%		To a stirred solution of 4-hydroxyisophthalaldehyde (0.1 1 g, 0.73 mmol) in Dimethylformamide (DMF) (5 ml.,), K2C03 (0.3 g, 2.17 mmol) is added and allowed to stir for about 20 minutes. After about 20 minutes, 2-(4-(iodomethyl)phenyl)-4,4,5,5-tetramethyl-l ,3,2-dioxaborolane (2) (0.3 g, 0.87 mmol) is added and stirred overnight at room temperature (RT), The completion of reaction is monitored by TLC. After completion of the reaction, solvent is evaporated and product is extracted with diethyl ether (3x 100 mL). The crude product is purified by column chromatography on silica gel using ethyl acetateMiexane (20:80) as an eluent to obtain compound 3 in good yield (60%). 1H NMR (400 MHz, CDC,) deltarhorhom 10.56 (s, 1H), 9.95 (s, 1H), 8.35 (d, J = 2.4 Hz, 1H), 8.08 (dd, J= 2 Hz, 8.8 Hz, 1H), 7.86 (d, J = 8 Hz, 2H), 7.44 (d, J = 8 Hz, 2H), 7.17 (d, J = 8 Hz, 1H), 5.32 (s, 2H), 1.35 (s, 12H). 13 C NMR (100 MHz, CDC,) deltarhorhom 190.1 , 188.5, 164.9, 137.9, 135.5, 135.3, 131.9, 129.9, 126.5, 125.2, 1 13.7, 84.0, 71.0, 24.9

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 10960 - 10965
[2]Patent: WO2012/123916,2012,A2 .Location in patent: Page/Page column 92-93
[3]Patent: WO2017/33163,2017,A1 .Location in patent: Page/Page column 33; 35
[4]Journal of the American Chemical Society,2011,vol. 133,p. 10960 - 10965

19
[ 3328-70-9 ]
N-(3-sulfonatopropyl)-2,3,3-trimethyl-3H-indolium [ No CAS ]
3-{2-[2-(3-{2-[3,3-dimethyl-1-(3-sulfopropyl)-2,3-dihydro-1H-2-indolyliden]ethylidene}-6-oxo-1,4-cyclohexadienyl)vinyl]-3,3-dimethyl-3H-1-indoliumyl}-1-propanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%		Indolenine 1a(0.5 g, 1.77 mmol) and dicarbaldehyde 2 (110 mg, 0.73 mmol) weredissolved in 2 ml acetic acid. The reaction mixture was heated to 80 Cfor 5 min and sodium acetate (200 mg, 2.43 mmol) was added. Thismixture was stirred for 1 h at 80 C and cooled to RT. Dark-reddishsolution was poured into 50 ml diethyl ether, the raw product was filteredand purified on preparative HPLC giving dye 3a (307 mg,0.45 mmol, 62%). MS m/z (El+) C36H40N2O7S2 calculated [M+H]+677.2, found 676.9.

Reference： [1]Dyes and Pigments,2018,vol. 159,p. 18 - 27
[2]Journal of the American Chemical Society,2011,vol. 133,p. 10960 - 10965

20
[ 3328-70-9 ]
[ 5418-63-3 ]
[ 108-24-7 ]
[ 1384511-92-5 ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium acetate; In acetic anhydride; at 80℃; for 0.5h;Inert atmosphere;	Preparation of Compound 3: A mixture of commercially available Compound 2 (50 mg, 0.33 mmol), NaOAc (83.9 mg, 1.02 mmol), and commercially available l,2,3,3-tetramethyl-3H-indolium iodide (210.6 mg, 0.70 mmol) was dissolved in 2 ml Ac20. The reaction mixture stirred for 30 minutes at 80 C under an Ar atmosphere and monitored by RP-HPLC (grad. 10 %-90 ACN in water, 20 minutes). After completion, the solvent was evaporated under reduced pressure, and the crude product was dissolved in DCM, filtered and concentrated to give compound 3 (210 mg) as a red solid.1H NMR (400MHz, CDC13 + drope of MeOD): delta = 9.63 (1H, s), 8.67 (1H, d, J=16.4 Hz), 8.52 (1H, d J=8.6 Hz), 8.27 (2H, m), 8.05 (1H, d, J=16.4 Hz), 7.62-7.70 (8H, m), 7.52 (1H, d, J=8.6 Hz), 4.54 (3H, s), 4.48 (3H, s), 2.49 (3H, s), 1.98 (6H, s), 1.88 (6H, s).13C NMR (400MHz, CDC13 + drope of MeOD): delta = 183.89, 183.32, 186.77, 154.20, 152.68, 145.82, 144.41, 143.96, 142.03, 136.88, 133.39, 133.23, 131.40, 131.05, 130.56, 130.25, 127.94, 127.94, 124.73, 123.48, 117.40, 115.93, 115.58, 115.53, 53.85, 53.52, 38.40, 37.92, 30.31, 27.38, 27.12, 27.12, 21.93, 0.57.MS (ESI): m/z calc. for C34H36N2022+: 252.2 ; found: 252.2 [M]+.

Reference： [1]Patent: WO2012/123916,2012,A2 .Location in patent: Page/Page column 63-64

21
[ 3328-70-9 ]
N-(3-sulfonatopropyl)-2,3,3-trimethyl-3H-indolium [ No CAS ]
C₃₈H₄₃N₂O₈S₂^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate; In acetic anhydride; at 80℃; for 0.5h;Inert atmosphere;	Synthesis of Compound 9 (also denoted NK-118; generating dye compound Sulfo-QCy7):Compound 9 was synthesized similarly as described for QCy7 (see, Scheme 1 above and Schemes 6 and 7 below) by using indolium-3 -propyl-sulfate (Compound 7) instead of indolium-iodide.A mixture of Compound 2 (20 mg, 0.13 mmol), NaOAc (33.9 mg, 0.41 mmol), and Compound 7 (see, Scheme 7 below; 79 mg, 0.27 mmol) was dissolved in 1 ml Ac20. The reaction mixture stirred for 30 minutes at 80 C under an Argon atmosphere and monitored by RP-HPLC (grad. 10%-90 ACN in water, 20 minutes). After completion, the reaction mixture was concentrated by evaporation under reduced pressure. The acetate derivative was dissolved in 4 ml MeOH. K2C03 (catalytic amount) was added to the suspension and the reaction mixture was stirred at room temperature for 60 minutes, and monitored by RP-HPLC (grad. 10%-90 ACN in water, 20 minutes). After completion, the reaction mixture was diluted with 4 ml H20, 800 AcOH, and purified by preparative RP-HPLC (grad. 10%-90 ACN in water, 20 minutes) to give Sulfo-QCy7 (44 mg, 51 % yield) as a red solid.1H NMR (400MHz, DMSO- 6): delta = 9.20 (1H, s), 8.52-8.59 (3H, m), 8.17 (1H, d, J=16.3 Hz), 8.07 (1H, d, J=7.30 Hz), 8.01 (1H, d, J=7.30 Hz), 7.90 (1H, d, J = 7.2 Hz), 7.86 (1H, d, J = 7.2 Hz), 7.61-7.68 (4H, m), 7.21 (4H, m, J = 8.7 Hz), 4.97 (2H, t, J = 7.6 Hz), 4.92 (2H, t, J = 7.6 Hz), 2.75 (2H, t, J = 6.0 Hz), 2.71 (2H, t, J = 6.0 Hz), 2.23-2.28 (4H, m), 1.86 (6H, s), 1.83 (6H, s).13C NMR (400MHz, DMSO- 6): delta= 183.07, 182.91, 164.26, 154.78, 147.93, 145.07, 144.95, 142.12, 142.05, 137.97, 135.54, 130.36, 130.39, 130.27, 128.28, 124.25, 124.19, 123.41, 116.41, 116.07, 114.54, 112.23, 53.28, 53.21, 48.29, 48.28, 46.83, 46.47, 27.45, 27.20, 25.77.MS (ESI): m/z calc. for : 675.8 ; found: 675.4 [M]~.

Reference： [1]Patent: WO2012/123916,2012,A2 .Location in patent: Page/Page column 65

22
[ 3328-70-9 ]
C₃₅H₄₃IN₄O₆ [ No CAS ]
C₄₃H₄₈N₄O₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide;	The synthesis of probe 34 is illustrated in Scheme 8. Z-Phe-Lys-PABA 35 is reacted with tetra-bromomethane and triphenylphosphine to generate iodide 36. Dialdehyde Compound 2 is alkylated with iodide 36 to give dialdehyde 37, which is then condensed with 2 equivalents of indolium- iodide to yield probe Compound 34.

Reference： [1]Patent: WO2012/123916,2012,A2 .Location in patent: Page/Page column 96

23
[ 3328-70-9 ]
[ 2301-80-6 ]
4,4'-(4-hydroxy-1,3-phenylene)bis(ethene-2,1-diyl)bis(1-methylpyridin-1-ium) iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83.2%	With piperidine In ethanol for 8h; Reflux;	4,4'-(4-Hydroxy-1,3-phenylene)bis(ethene-2,1-diyl))bis(1-methylpyridin-1-ium)iodide(6b) To a mixture solution of compound 3(75.1 mg, 0.5 mmol) and 1,4-dimethylpyridin-1-ium iodide (1.0 mmol, 235.1 mg)in ethanol (10 mL), a drop of piperidine wasadded and then the mixture solution was refluxed for 8 h. After the reaction, the solution was cooled to roomtemperature and washed twice with methanol to obtain a black solid (478.0 mg). Yield: 83.2%, mp 80.5-85.0 °C. IR ν(KBr, cm-1): 3016, 1642, 1585, 1510, 1470, 1421, 1329, 1282, 1192,1170, 1043, 972, 819, 747, 667, 585, 574, 1H NMR (400 MHz, DMSO-d6): δ (ppm) 8.66 (d, J = 8.2 Hz, 2H, 2 × Ar-H) 8.59 (d, J = 7.2 Hz, 2H, 2 × Ar-H),8.06 (d, J = 6.2 Hz, 2H, 2 × Ar-H), 8.05 (d, J =8.2 Hz, 2H, 2 × Ar-H),7.96 (s, 1H, Ar-H), 7.84 (d, J = 7.1 Hz, 2H, 2 × Ar-H), 7.73 (d, J = 11.3 Hz, 1H, CH),7.53 (d, J = 10.6 Hz, 1H, CH)), 7.06 (d, J = 7.1 Hz, 1H, Ar-H),6.63 (d, J = 7.2 Hz, 1H, Ar-H), 4.16 (s, 3H, CH3), 4.14 (s, 3H, CH3),13C NMR (151 MHz, DMSO-d6):δ (ppm) 154.3, 153.6, 144.8, 144.5, 142.4, 139.4, 132.8, 132.3, 123.5, 122.7,121.9, 121.5, 120.5, 116.45, 46.85, 46.65. MS (ESI+): m/z calcd for C22H22N2O2+330.17, this compoundis very easy to attract particles and cannot get mass spectra.
80%	With piperidine In ethanol at 80℃; for 0.5h; Inert atmosphere;

Reference： [1]Zhu, Ming-Sen; Zhang, Xiao-Qing; Wei-Ma; Sun, Ru; Xu, Yu-Jie; Ge, Jian-Feng [Bioorganic and Medicinal Chemistry Letters, 2021, vol. 48]
[2]Karton-Lifshin, Naama; Albertazzi, Lorenzo; Bendikov, Michael; Baran, Phil S.; Shabat, Doron [Journal of the American Chemical Society, 2012, vol. 134, # 50, p. 20412 - 20420]

24
[ 3328-70-9 ]
[ 59643-43-5 ]
C₃₆H₄₈O₃⁽²⁺⁾*2I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With piperidine In ethanol at 80℃; Inert atmosphere;

Reference： [1]Karton-Lifshin, Naama; Albertazzi, Lorenzo; Bendikov, Michael; Baran, Phil S.; Shabat, Doron [Journal of the American Chemical Society, 2012, vol. 134, # 50, p. 20412 - 20420]

25
[ 3328-70-9 ]
[ 16859-86-2 ]
C₃₀H₂₆N₂O⁽²⁺⁾*2I^(1-) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 20412 - 20420

26
[ 3328-70-9 ]
[ 1656-44-6 ]
2,4-dinitrophenyl 2,4-diformylphenyl sulphate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 2098 - 2104

27
[ 3328-70-9 ]
[ 70-34-8 ]
4-(2',4'-dinitrophenoxy)benzene-1,3-dicarbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 1h;	Commercially available 1-fluoro-2,4-dinitro-benzene (300mg, 2mmol) was added to a stirring solution of commercial available <strong>[3328-70-9]4-hydroxybenzene-1,3-dicarbaldehyde</strong> (372mg, 2mmol) and potassium carbonate (414mg, 3mmol) in N,N-dimethylformamide (5mL) at room temperature. After 1h, TLC indicated that the start materials consumed. The mixture was diluted with ethyl acetate (50mL) and washed with water (30×3mL). The organic phase was dried over Na2SO4, evaporated in vacuo and the residue was purified by flash column chromatography eluting with petroleum/EtOAc (3:1) to afford 4-(2?,4?-dinitrophenoxy) benzene-1,3-dicarbaldehyde (537mg, yield: 85%) as pale yellow solid. 1H NMR (400MHz, DMSO-d6) delta=10.33 (s, 1H), 10.10 (s, 1H), 8.97 (d, J=2.8Hz, 1H), 8.56 (dd, J=2.8, 9.2Hz, 1H), 8.50 (d, J=2.2Hz, 1H), 8.26 (dd, J=2.1, 8.5Hz, 1H), 7.57 (d, J=9.2Hz, 1H), 7.46 (d, J=8.6Hz, 1H). 13C NMR (100MHz, DMSO-d6) delta=192.02, 189.01, 160.17, 153.32, 143.61, 140.85, 136.84, 133.82, 132.32, 130.47, 127.48, 122.76, 122.64, 120.98.

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2019,vol. 213,p. 416 - 422
[2]RSC Advances,2014,vol. 4,p. 11147 - 11151

28
[ 14273-90-6 ]
[ 3328-70-9 ]
C₁₅H₁₈O₅ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 9793 - 9796

29
[ 110-53-2 ]
[ 3328-70-9 ]
[ 114515-49-0 ]

Yield	Reaction Conditions	Operation in experiment
72%		Magnesium turnings (0.4g, 16 mmol) and a magnetic bar were introduced to a 100 ml bi-necked round bottom flask equipped with a condenser and an isobaric bulb. Anhydrous tetrahydrofurane, THF, (10 ml) and a small iodine crystal were added to the flask, and the isobaric bulb was filled with bromopentane (2.5 g, 16 mmol) and dissolved in anhydrous THF (10 ml). The mixture was stirred and refluxed under nitrogen gas. When the yellow color of iodine disappeared totally, the bromopentane solution was added drop wise, while stirring under reflux. Stirring was continued until all magnesium disappeared. Vanillin (1g, 6.57 mmol) in anhydrous THF (15 ml) and a magnetic bar were introduced into a 100 ml round bottom flask, the mixture was stirred and the flask flashed with nitrogen gas and cooled in salt-ice bath. Using a syringe, the prepared Grignard (C5H11MgBr) was added drop wise to the mixture in the cooled flask while stirring and cooling. At the end of addition, stirring and cooling were continued for an additional 30 minutes. Hydrolysis using NH4Cl solution, extraction by ethyl acetate and dryness over anhydrous sodium sulfate were done. Filtration and evaporation of solvents were performed. After column chromatography on silica gel, alcohol 3 (1 g, 72% yield) was isolated as white crystals; Melting point: 77-79 C; Rf = 0.28 (Ethyl acetate/ Hexane: 30/70).1H NMR (CDCl3, 300MHz): delta, ppm: 0.89 (t, 3H, J= 6.57 Hz); 1.29-1.46 (m, 6H); 1.64-1.86 (m, 2H); 1.99 (s, 1H); 3.90 (s, 3H); 4.59 (t, 1H, J= 7.02 Hz); 5.71 (s, 1H); 6.78-6.90 (m, 3H); 13C NMR (CDCl3, 75MHz): delta, ppm: 14.0 22.5, 25.6, 31.7, 39.0, 55.9, 74.6, 108.3, 114.1, 118.9, 137.0, 144.9, 146.6.

Reference： [1]European Journal of Pharmacology,2015,vol. 750,p. 66 - 73

30
[ 4930-98-7 ]
[ 3328-70-9 ]
C₁₈H₁₆N₆O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86.2%	With acetic acid; In ethanol; at 80℃; for 6h;	In a 250 mL round bottom flask,Add hydroxyisophthalaldehyde 0.7500g (5mmol), 2-hydrazinopyridine 0.5995g (5.5 mmol),Catalyzed by 5 mL (0.05 mmol) glacial acetic acid,30mL ethanol solvent,Stir at 80C for 6h under refluxThere are brown precipitates,The crude product is recrystallized from ethanol,A dark yellow product is obtained,That is, sensor molecule Y,Yield: 86.2%

Reference： [1]New Journal of Chemistry,2015,vol. 39,p. 4162 - 4167
[2]Patent: CN104610139,2017,B .Location in patent: Paragraph 0041; 0042; 0043

31
[ 3328-70-9 ]
[ 279216-12-5 ]
C₂₇H₂₄N₄O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate; In acetonitrile; at 90℃;	A mixture of <strong>[3328-70-9]4-hydroxy-1,3-benzenedicarboxaldehyde</strong> (221 mg, 1.48 mmol), N4-Cl ligand (500 mg,1.48 mmol) was dissolved in CH3CN (80 mL). K2CO3 (2 g,14.76 mmol) was added and the resulting mixture was refluxed at 90 C for overnight (33). After cooling to room temperature, the mixture was filtered. The residue was washed thoroughly with CH3CN. Then total filtrate was evaporated in vacuo to obtain residue. This residue was dissolved in 50 mL of CH2Cl2 was extracted with 3 x 20 mLof brine solution. Finally, the organic layer was washed with 2 x 20 mL water, dried over Na2SO4, evaporated in vacuo and the residue was purified on neutral alumina column (solvent = CH2Cl2/MeOH: 90/10) to obtain the product(600 mg, yield 90%). 1H NMR (400 MHz, CDCl3) deltappm 3.97 (6H, s), 5.39 (2H, s), 7.16-7.19 (2H, t, J = 6.4 Hz), 7.24 (1H, d, J = 8.8 Hz), 7.36 (1H, d, J = 7.6 Hz), 7.56-7.59 (3H, m), 7.65-7.75 (3H, m), 8.05-8.08 (1H, dd, J = 2 Hz, 6.8 Hz), 8.35 (1H, d, J = 2.4 Hz), 8.54 (2H, d, J = 4 Hz), 9.94 (1H, s), 10.59 (1H, s). 13C NMR (100 MHz, CDCl3) deltappm 29.6, 59.9, 71.5, 113.8, 119.7, 122.2, 122.6, 123.1, 125.0, 129.8, 131.6, 135.9, 136.7, 137.5, 148.7, 154.4, 158.8, 159.1, 164.5, 188.3, 190.0. MS (EI): m/z 453.6 [M + H]+ for C27H24N4O3. Elemental analysis: Found C, 71.65; H, 5.36; N, 12.40; Calcd. C, 71.67; H, 5.35; N, 12.38 for C27H24N4O3.

Reference： [1]Supramolecular Chemistry,2015,vol. 27,p. 589 - 594

32
[ 498-66-8 ]
[ 3328-70-9 ]
C₁₅H₁₆O₃ [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 13791 - 13794

33
[ 100-97-0 ]
[ 90-02-8 ]
[ 3328-69-6 ]
[ 3328-70-9 ]

Yield	Reaction Conditions	Operation in experiment
10.5%; 9.5%		General procedure: To a solution of substrates (1a-1q, 0.15 mmol) in trifluoroacetic acid (5 ml), hexamethylenetetramine (0.3 mmol) and cuprous oxide (0.15 mmol) were added. The reaction mixture was refluxed for about 5 h, cooled to room temperature, followed by addition of hydrochloric acid (3 N, 5 ml). After stirring for another 1 h, the solution was concentrated under reduced pressure. The products were purified by silica gel column chromatography (200-300 mesh).

Reference： [1]Research on Chemical Intermediates,2015,vol. 41,p. 8147 - 8158

34
[ 3328-70-9 ]
[ 137-07-5 ]
3-(benzo[d]thiazol-2-yl)-4-hydroxybenzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 20℃; for 12h;	25 mL of a round bottom flask, 10 mmol of ethanol as a solvent, 5 mmol of 2-aminophenyl mercaptan and 5 mmol of product 2 were added and the mixture was allowed to react at room temperature for 12 hours. The product 3 was isolated and purified by silica gel column chromatography after the dry solvent and the crude product were passed through a silica gel column by a mixed solution of dichloromethane / petroleum ether in a volume ratio of 2: 1.
	In dimethyl sulfoxide; at 60℃; for 6h;	Compound 1 and o-aminothiophenol are dissolved in dimethyl sulfoxide (DMSO).The ratio of the amount of the compound 1 and the o-aminothiophenol is 1:1.The reaction was heated at 60 degrees for 6 hours.TLC was used to monitor the progress of the reaction. After the reaction was completed, the reaction was cooled to room temperature, water was added, and then liquid-extracted, dried, and subjected to column chromatography.Obtaining compound 2;

Reference： [1]Analytical Chemistry,2016,vol. 88,p. 4426 - 4431
[2]Patent: CN105038766,2017,B .Location in patent: Paragraph 0018; 0049; 0060; 0070; 0081
[3]Patent: CN109705111,2019,A .Location in patent: Paragraph 0023

35
[ 3328-70-9 ]
[ 106-93-4 ]
C₁₀H₉BrO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile; at 70℃;	4-Hydroxyisophthalaldehyde (150 mg, 1 mmol) was dissolved in anhydrous acetonitrile (5.0 mL).1,2-Dibromoethane (1.9 g, 10 mmol) was added followed by K2CO3 (276 mg, 2 mmol) at room temperature. Then the reaction was stirred at 70 oC for overnight. After the reaction accomplished, the reaction solution was filtered, and the solvent was removed in vacuo. The residue was dissolved in anhydrous THF (10 mL) at -40 oC. tBuOK (0.5 mmol) was slowly added in 10 mins. Then the reaction was stirred at -40 oC for 30 mins. After the reaction accomplished, the reaction was quenched by water, then the reaction solution was extracted by EtOAc (30 mL ×3). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica column (Hexanes: EtOAc = 25:1) to afford pure 1 (138 mg, yield 78%, 2 steps) as a white solid. [0506] 1H NMR: (500 MHz, methylene chloride-d2) delta 10.46 (d, J = 0.9 Hz, 1H), 9.96 (s, 1H), 8.37- 8.28 (m, 1H), 8.13-8.07 (m, 1H), 7.25 (d, J = 8.6 Hz, 1H), 6.85-6.76 (m, 1H), 5.10-5.05 (m, 1H), 4.82-4.78 (m, 1H). [0507] 13C NMR(126 MHz, methylene chloride-d2) delta 190.52, 188.42, 163.28, 146.39, 135.99, 132.02, 131.64, 126.07, 116.81, 100.43. [0508] HRMS: [M+H]+ m/z calcd. for [C10H9O3]+ 177.0546, found 177.0545

Reference： [1]Patent: WO2016/109733,2016,A1 .Location in patent: Paragraph 0504-0508

36
[ 3328-70-9 ]
[ 38925-99-4 ]
C₂₆H₂₂N₂OS₂⁽²⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%		Piperidine (8 iL) is added to a stirred solution of Nmethyi.-2methylbenzothiazole (1) (0.1 g,0.34 mmoi) in ethanol (8 mL), After about 10 miii, 4-hydroxyisophthalaidehyde (2) (20 mg,0,14 mmoi) in ethanol (2 mL) was added and the reaction mixture is stirred at about 80 C for about 3 hours under nitrogen atmosphere. After completion of reaction, solvent is evaporated and the crude product is purified by preparative RP-HPLC (grad. 50--65 acetonitrile in water, about 12 mm) to obtain the probe QCyDT as a yellow powder.Yield 45%. 1R (neat): 3390, 3065, 3015, 1682, 1667, 1582, 1505, 1121 1H NMR (400MHz, DMSO-d6) dppm: 8.59 (d, J= 2 Hz, iN), 8.42 (d, J= 8.1 Hz, 2H), 8.30 (d, J= 8.2 Hz,IH), 8.26 (d,.J= 3,3 Hz, IH), 8.23 (d,J= 10.7 Hz, 1H), 8.19 (dd,J 2Hz, J 8.7 Hz, IN),8.13 (dd, J= 8.1 Hz, J = 16 Hz, 2K), 7.98-7.89 (m, 3K), 7.86 (dd. J= 1.1 Hz, J= 9.5 Hz,IH), 7.837.78 (m, 2H), 7.22 (d, J= 8,7 Hz, 1H), 4.36 (s, 6H). 1C NMR (100 MHz, DMSO- d6) 172.1, 171,8, 161.8, 147.7, 142.2, 142.1, 142.0, 134.8, 132.6, 129.5, 128.5, 127.8, 127.6, 125.9, 124.1, 121.5, 117.7, 116.9, 116.8, 114.3, 111.8, 36.3, 36.2. FIRMS (ESIMS):found 441.1070, calcd. for C26H22N20S2 [M21H]? mlz = 441.1095 (Figures 23 and 2.4)

Reference： [1]Patent: WO2017/33162,2017,A1 .Location in patent: Page/Page column 28; 29
[2]Nucleic Acids Research,2015,vol. 43,p. 8651 - 8663

37
[ 3328-70-9 ]
[ 14134-81-7 ]
[ 108-24-7 ]
2d Acetyl-QCy₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate; at 80℃; for 0.75h;Inert atmosphere;	To a suspension containing 50.0 mg (0.33 mmol) of isophthalaldehyde, 218 mg (0.69 mmol) of 1-ethyl-2,3,3-trimethyl-3H-indolium iodide and 83.9 mg (1.02 mmol) of sodium acetate in 5 mL of dry acetic anhydride was applied a positive pressure of argon. The resulting reaction mixture was stirred at 80 C for 45 min leading to the precipitation of the desired dye as an orange solid. The solvent was removed by centrifugation and the resulting solid was washed twice with acetic anhydride and with Et20. The solid was then dried under vacuum to afford 2c as an orange solid, which was used directly for the next step: yield 239 mg (92%); 1H MR (CDCl3) delta (1.70 m, 6H), 1.87 (s, 6H), 2.09 (s, 6H), 2.47 (s, 3H), 5.20 (q, 2H, J= 7.4 Hz), 5.28 (q, 2H, J= 7.4 Hz), 7.54-7.71 (m, 9H), 8.19 (d, 1H, J= 16.1 Hz), 8.32 (d, 1H, J= 16.2 Hz), 8.44 (d, 1H, J= 16.2 Hz), 9.07 (d, 1H, J= 16.3 Hz), 9.29 (d, 1H, J= 8.7 Hz) and 10.00 (s, 1H); 13C NMR (CDCl3) £ 15.0, 15.2, 21.4, 27.0, 27.3, 44.8, 45.4, 52.9, 53.5, 114.2, 114.6, 115.1, 115.5, 123.2, 123.3, 124.4, 126.8, 129.6, 130.1, 130.3, 130.8, 133.3, 134.6, 137.6, 140.2, 140.3, 143.8, 144.9, 147.0, 153.8, 154.1, 167.9, 182.0 and 183.0; mass spectrum (MALDI), miz 266.46 (M)2+/2 (theoretical miz 266.15).

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 12009 - 12012
[2]Patent: WO2017/218537,2017,A1 .Location in patent: Paragraph 00078; 00088

38
[ 3328-70-9 ]
[ 3958-60-9 ]
4-(o-nitrobenzyloxy)isophthalaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%		General procedure: A solution containing 50.0 mg (0.33 mmol) of 4-hydroxyisophthalaldehyde and 91.2 mg (0.66 mmol) of K2CO3 in 2 mL of dry DMF was stirred under argon at room temperature for 10 min. The, 85.5 mg (0.40 mmol) of nitrobenzyl bromide was added and the reaction mixture was stirred under argon overnight. After the reaction was completed (monitored by silica gel TLC using 2:1 hexanes-ethyl acetate), the reaction mixture was diluted with 50 mL of EtOAc and then washed with two 50-mL portions of brine and with 50 mL of water. The organic layer was dried (MgSO4) and concentrated under diminished pressure. The crude mixture was solubilized in the minimum amount of CH2Cl2 and hexane was added to effect the precipitation of a colorless solid. The precipitate was isolated by filtration to give the desired compounds 1. The compound was prepared using 85.5 mg (0.40 mmol) of o-nitrobenzyl bromide. Compound la was obtained as a colorless solid: yield 90.0 mg (96%); mp 145 C; silica gel TLC Rf 0.60 (1:1 hexanes-ethyl acetate); NMR (CDCl3) delta 5.73 (s, 2H), 7.24 (d, 1H, J= 8.7 Hz), 7.58 (t, 1H, J= 8.1 Hz), 7.77 (t, 1H, J= 7.5 Hz), 7.92 (t, 1H, J= 7.8 Hz ), 8.14 (m, 1H), 8.24 (d, 1H, J= 8.2 Hz ), 8.39 (m, 1H), 9.97 (d, 1H, J= 0.7 Hz) and 10.58 (d, 1H, J= 1.1 Hz) ; 13C NMR (CDCl3) 68.1, 113.7, 125.4, 125.5, 128.5, 129.3, 130.5, 131.8, 132.7, 134.6, 136.2, 147.0, 164.1, 188.2 and 190.0; mass spectrum (APCI), mlz 286.0711 (M+H)+ (C15H12N requires mlz 286.0715).

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 12009 - 12012
[2]Patent: WO2017/218537,2017,A1 .Location in patent: Paragraph 00078; 00081; 00082

39
[ 3291-00-7 ]
[ 3328-70-9 ]
C₂₂H₁₈N₄O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.09 g	With acetic acid; In ethanol; at 80℃; for 12h;	Added 4-hydroxyisophthalaldehyde (2.94 g, 20 mmol), 2-(hydrazonomethyl)phenol (5.71 g, 42 mmol) and several drops of acetic acid to ethanol as a reaction mixture. Stirred this mixture at 80 C for 12 hours in a dry flask. After the reaction was complete, the reaction solution was evaporated under reduced pressure and extracted with ethyl acetate. The residue was purified by column chromatography on silica gel using progressively more polar 50:1 to 30:1 petroleum ether/ethyl acetate as the mobile phase to give compound L as a buff powder (3.09 g, m.p 270 ~ 273 C). 1H NMR (600 MHz, d6-DMSO) delta 11.52 (s, 1H), 11.34 (s, 1H), 11.10 (s, 2H), 9.03 (d, J = 4.8 Hz, 1H), 8.93 (s, 1H), 8.76 (s, 1H), 8.29 (s, 1H), 7.95 (d, J = 7.7 Hz, 1H), 7.90 (d, J = 8.6 Hz, 1H), 7.73 (d, J = 2.6 Hz, 2H), 7.67 (d, J = 3.2 Hz, 1H), 7.66 (s, 1H), 7.39 (d, J = 7.2 Hz, 2H), 7.10 (d, J = 8.4 Hz, 1H), 6.97 (s, 4H). 13C NMR (151 MHz, d6-DMSO) delta 163.44, 162.97, 161.94, 161.36, 159.09, 133.58, 133.27, 131.68, 131.27, 120.04, 119.56, 118.69, 116.87. The [L - H+]- peak appeared at 385.1021. which is coinciding well with that for the species [C22H17N4O3 - H]- (m/z = 385.1345).

Reference： [1]Tetrahedron,2017,vol. 73,p. 2938 - 2942

40
[ 3328-70-9 ]
[ 615-21-4 ]
2,4-bis[[(2-benzothiazolythio)hydrazinylidene]methyl]phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86.2%	With acetic acid; In ethanol; at 75℃; for 4h;	The compound J can be readily prepared by a simple andlow cost Schi base reaction of 4-hydroxyisophthalaldehydeand 2-hydrazinylbenzothiazole. 4-hydroxyisophthalaldehyde(0.7500 g, 5 mmol), 2-hydrazinylbenzothiazole (0.60 g, 5.5mmol) and a catalytic amount of acetic acid (AcOH) werecombined in hot absolute EtOH (30 mL). The solution wasstirred under reux for 4 h. After cooling to room temperature,the dark yellow precipitate was fltered, washed three timeswith hot absolute ethanol, then recrystallized with EtOH toobtain a yellow powdered product J (4.31 mmol) in 86.2% yield(m.p. > 300C). 1H NMR (DMSO-d6, 400 MHz) delta: 12.24 (s,2H), 10.87 (s, 1H), 8.48-7.01 (m, 13H,) (Figure S1). 13C NMR(DMSO-d6, 100 MHz) delta/ppm: 167.4, 167.1, 162.8, 158.3, 129.2,126.7, 126.5, 126.4, 122.3, 122.1, 121.9, 120.6, 117.3 (Figure S2).ESI-MS calcd for [C18H16N6OS2 + H+]+ 445.08. Found 445.07(Figure S3)

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2017,vol. 192,p. 565 - 569

41
[ 104-92-7 ]
[ 3328-70-9 ]
4-hydroxy-3-(4-methoxybenzoyl)benzaldehyde [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 5080 - 5093

42
[ 3328-70-9 ]
C₁₆H₁₆ClN₃S [ No CAS ]
C₂₄H₁₈ClN₃O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With zinc(II) perchlorate; In dimethyl sulfoxide; at 100℃;	Synthetic Method Reference Example 15, Compound M6 (318 mg, 1 mmol), 4-hydroxyisophthalaldehyde (150 mg, 1 mmol), silver triflate (2.6 mg, 0.01 mmol) and DMSO (3 mL) at a reaction temperature of 100 C to give 280 mg of a yellow solid in 63% yield.;_The compound M6 (318 mg, 1 mmol), 2-methanesulfonamidobenzaldehyde (597 mg, 3 mmol), copper acetate (182 mg, 1 mmol) and NMP (5 mL) were reacted at 120 C for 12 hours. After the completion of the reaction, the mixture was cooled to room temperature, ethyl acetate was added, the organic phase was washed with saturated NH4Cl solution, water and saturated sodium chloride solution successively, dried over anhydrous sodium sulfate, concentrated and purified by flash column chromatography to obtain white solid 300mg, yield 60%

Reference： [1]Patent: CN107383057,2017,A .Location in patent: Paragraph 0063; 0080; 0081

43
[ 3328-70-9 ]
1-(1-methyl-1H-indol-3-yl)-1H-1λ³-benzo[b]iodo-3(2H)-one [ No CAS ]
4-hydroxy-3-(1-methyl-1H-indole-3-carbonyl)benzaldehyde [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 1473 - 1476

44
[ 36429-27-3 ]
[ 3328-70-9 ]
C₃₅H₄₉NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 65℃; for 6h;Inert atmosphere; Reflux;	B. 575 g of 4-hydroxy-1,3-benzenedialdehyde in ethanol solution heated by nitrogen bath(solution containing 25g of ethanol) to reflux, heated to a temperature of 65 C,63 g of ethanol solution containing PS02 (18 g of ethanol in solution) was added dropwise.After the color has turned purple, continue heating and refluxing for 6 hours. After cooling to room temperature, pour the reaction mixture into ice and stir until the ice is completely melted to give a lavender emulsion.After fully standing, the water and ethanol are distilled off, and the viscous material is recrystallized from methanol., filter dry, get a lavender powder,The alkyl spiropyran photochromic compound (I).
	In ethanol; at 65℃; for 6h;Inert atmosphere;	575 g of <strong>[3328-70-9]4-hydroxy-1,3-benzenedicarboxaldehyde</strong> in ethanol (25 g of ethanol in solution) is heated to reflux under nitrogen protection in an oil bath, heated to a temperature of 65C, and 63 g of ethanol solution containing PS02 is added dropwise (in solution Contains 18g of ethanol),After the color has turned purple, continue to heat and reflux for 6 hours. After cooling to room temperature, pour the reaction mixture into ice and stir.After the ice is completely melted, a lavender emulsion is obtained. After fully standing, the water and ethanol are distilled off.The viscous material is recrystallized from methanol, filtered, and dried to give a pale lavender powder.The alkyl spiropyran photochromic compound (I).

Reference： [1]Patent: CN107722028,2018,A .Location in patent: Paragraph 0069; 0071
[2]Patent: CN107722027,2018,A .Location in patent: Paragraph 0063; 0065

45
[ 3328-70-9 ]
N-(3-sulfonatopropyl)-2,3,3-trimethyl-3H-indolium [ No CAS ]
3-{2-[2-(3-{2-[3,3-dimethyl-1-(3-sulfopropyl)-2,3-dihydro-1H-2-indolyliden]ethylidene}-6-oxo-1,4-cyclohexadienyl)vinyl]-3,3-dimethyl-3H-1-indoliumyl}-1-propanesulfonate [ No CAS ]
3-{2-[2-(3-{2-[3,3-dimethyl-1-(3-sulfopropyl)-3H-2-indoliumyl]-1-ethenyl}-4-methylcarbonyl-oxyphenyl)-1-ethenyl]-3,3-dimethyl-3H-1-indoliumyl}-1-propanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%; 6%		Indolenine 1a(1.5 g, 5.33 mmol) and dicarbaldehyde 2 (330 mg, 2.2 mmol) weredissolved in a mixture of 6 ml acetic anhydride and 6 ml acetic acid(50:50 v/v). The reaction mixture was heated to 80 C for 5 min andsodium acetate (700 mg, 8.53 mmol) was added. This mixture wasstirred for 1 h at 80 C and cooled to RT. Dark-reddish solution waspoured into 100 ml diethyl ether. The resulted mixture of 3a-Ac and 3awas filtered and separated on a preparative HPLC giving 3a-Ac(100 mg, 0.138 mmol, 6%) and 3a (760 mg, 1.12 mmol, 42%). 3a-Ac:1H NMR (400 MHz, H2O-CH3CN, 50:50 v/v, ppm): delta 8.97 (d,J=2.2 Hz, 1H), 8.43 (d, J=16.2 Hz, 1H), 8.30 (dd, J=8.6, 2.2 Hz,2H), 7.98 (d, J=16.5 Hz, 1H), 7.87 (m, 3H), 7.72 (m, 2H), 7.61 (m,4H), 7.52 (d, J=8.6 Hz, 1H), 4.86 (m, 4H), 2.98 (m, 4H), 2.44 (s, 3H),2.37 (m, 4H), 1.82 (s, 6H), 1.77 (s, 6H). 13C NMR (400 MHz,H2O-CH3CN, 50:50 v/v, ppm): delta 183.9, 183.5, 170.1, 153.4, 146.3,145.0, 142.0, 136.2, 131.7, 131.0, 130.0, 124.9, 124.0, 116.7, 116.5,116.0, 54.0, 48.0, 46.9, 26.7, 26.5, 25.5, 21.5. HRMS m/z (El+)C38H42N2O8S2 calculated [M+H]+ 719.2461, found 719.2481. 3a: 1HNMR (400 MHz, H2O-CH3CN, 50:50 v/v, ppm): delta 8.79 (s, 1H), 8.59 (d,J=16.5 Hz, 1H), 8.37 (d, J=16.2 Hz, 1H), 8.17 (d, J=8.7 Hz, 1H),7.93 (d, J=16.5 Hz, 1H), 7.82 (1H, second order), 7.78 (1H, secondorder), 7.70 (m, 2H), 7.60 (m, 4H), 7.20 (d, J=8.7 Hz, 1H), 4.77 (ABq,4H), 2.99 (ABq, 4H), 2.35 (m, 4H), 1.79 (d, J=1.4 Hz, 12H). 13C NMR(400 MHz, H2O-CH3CN, 50:50 v/v, ppm) delta=182.1, 163.3, 153.9,148.4, 143.8, 140.5, 136.8, 133.8, 129.4, 127.0, 122.6, 122.0, 117.7,114.8, 112.4, 110.2, 52.3, 47.1, 45.4, 25.9, 23.7. MS m/z (El+)C36H40N2O7S2 calculated [M+H]+ 677.2, found 676.9.

Reference： [1]Dyes and Pigments,2018,vol. 159,p. 18 - 27

46
[ 3328-70-9 ]
3-(5-carboxymethyl-2,3,3-trimethyl-3H-1-indoliumyl)-1-propanesulfonate [ No CAS ]
3-{5-carboxymethyl-2-[2-(3-{2-[5-carboxymethyl-3,3-dimethyl-1-(3-sulfonatopropyl)-3H-2-indoliumyl]-1-ethenyl}-4-methylcarbonyloxyphenyl)-1-ethenyl]-3,3-dimethyl-3H-1-indoliumyl}-1-propanesulfonate [ No CAS ]
3-{5-carboxymethyl-2-[2-(3-{2-[5-carboxymethyl-3,3-dimethyl-1-(3-sulfopropyl)-2,3-dihydro-1H-2-indolyliden]ethylidene}-6-oxo-1,4-cyclohexadienyl)-1-ethenyl]-3,3-dimethyl-3H-1-indoliumyl}-1-propanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6%; 0.5%		Indolenine 1c (180 mg, 0.53 mmol) and dicarbaldehyde 2 (32 mg,0.212 mmol) were dissolved in a mixture of 3 ml acetic anhydride and3 ml acetic acid (50:50 v/v). The reaction mixture was heated to 80 Cfor 5 min and sodium acetate (220 mg, 2.68 mmol) was added, the reactionmixture was stirred for 1 h at 80 C and after cooled to RT. Darkreddishsolution was poured into 100 ml diethyl ether and the obtainedprecipitate was filtered and dried in dessicator. The mixture of compounds3c-Ac and 3c was separated on preparative HPLC giving 3c-Ac(10 mg, 0.012 mmol, 6%) and 3c (0.8 mg, 0.001 mmol, 0.5%). 3c-Ac:1H NMR (400 MHz, DMSO-d6, ppm): delta 9.31 (d, J=1.6 Hz, 1H), 8.67(dd, J=8.8, 1.6 Hz, 1H), 8.61 (d, J=16 Hz, 1H), 8.22 (d, J=5.2 Hz,2H), 8.11 (d, J=16 Hz, 1H), 8.05 (d, J=8.4 Hz, 1H), 8.02 (d,J=8.4 Hz, 1H), 7.76 (dd, J=16, 1.2 Hz, 2H), 7.61 (d, J=8.8 Hz, 1H),7.57 (dd, J=8.4, 1.2 Hz, 1H), 7.54 (dd, J=8.8, 1.6 Hz, 1H), 4.98 (m,4H), 3.78 (s, 4H), 2.71 (m, 4H), 2.48 (s, 3H), 2.27 (m, 4H), 1.86 (s, 6H),1.79 (s, 6H). HRMS m/z (El+) C42H46N2O12S2 calculated [M+H]+835.2570, found mass: 835.2552. 3c: 1H NMR (400 MHz,H2O-CH3CN, 50:50 v/v, ppm): delta 8.71 (d, J=1.7 Hz, 1H), 8.56 (d,J=16.5 Hz, 1H), 8.35 (d, J=16.5 Hz, 1H), 8.15 (dd, J=8.8, 1.7 Hz,1H), 7.86 (d, J=16.5 Hz, 1H), 7.76-7.71 (d, J=8.3 Hz, 2H), 7.60 (bs,2H), 7.58 (d, J=16.5 Hz, 1H), 7.50-7.48 (d, J=8.3 Hz, 2H), 7.18 (d,J=8.8 Hz, 1H), 4.72 (ABq, 4H), 3.78 (bd, J=2.9 Hz, 4H), 2.97 (ABq,4H), 2.33 (m, 4H), 1.78 (s, 12H). 13C NMR (400 MHz, H2O-CH3CN,50:50 v/v, ppm): delta 183.5, 183.3, 175.3, 175.2, 164.2, 155.0, 149.5,145.0, 140.7, 137.8, 137.5, 135.1, 131.8, 125.1, 124.0, 118.7, 115.9,115.6, 113.8, 111.5, 66.6, 53.41, 48.3, 48.1, 46.71, 46.31, 26.9, 26.8,24.65. HRMS m/z (El+) C40H44N2O11S2 calculated [M+H]+793.2465, found mass: 793.2462.

Reference： [1]Dyes and Pigments,2018,vol. 159,p. 18 - 27

47
[ 3328-70-9 ]
3-(5-carboxymethyl-2,3,3-trimethyl-3H-1-indoliumyl)-1-propanesulfonate [ No CAS ]
3-{5-carboxymethyl-2-[2-(3-{2-[5-carboxymethyl-3,3-dimethyl-1-(3-sulfopropyl)-2,3-dihydro-1H-2-indolyliden]ethylidene}-6-oxo-1,4-cyclohexadienyl)-1-ethenyl]-3,3-dimethyl-3H-1-indoliumyl}-1-propanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%		Indolenine 1c (1.21 g,3.56 mmol) and dicarbaldehyde 2 (178 mg, 1.18 mmol) were dissolvedin 2 ml acetic acid. The reaction mixture was heated to 80 C for 5 minand sodium acetate (600 mg, 7.31 mmol) was added. This mixture wasstirred for 1 h at 80 C and cooled to RT. Dark-reddish solution waspoured into 50 ml diethyl ether and the raw dye 3c was filtered andpurified on a preparative HPLC giving 3c (766 mg, 0.96 mmol, 82%).HRMS m/z (El+) C40H44N2O11S2 calculated [M+H]+ 793.2465, foundmass: 793.2462.

Reference： [1]Dyes and Pigments,2018,vol. 159,p. 18 - 27

48
[ 3328-70-9 ]
[ 106-96-7 ]
C₁₁H₈O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78.1%		Take compound 1 (180 mg, 1.2 mmol),K2CO3 (331 mg, 2.4 mmol),3 mL DMF was stirred in a 50 mL round bottom flask for 10 minutes in an ice water bath.Add bromopropyne (110 muL, 1.44 mmol) and stir for 2 minutes in an ice water bath.Stir at 25 C for 12 hours, then separate by column chromatography (eluent: ethyl acetate).The solvent was distilled off and dried in vacuo to give a yellow solid, 176.2 mg, which was Compound 2(Yield, 78.1%).

Reference： [1]Patent: CN109206351,2019,A .Location in patent: Paragraph 0018; 0019

49
[ 3328-70-9 ]
[ 88071-91-4 ]
C₁₇H₁₃NO₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87.2%		1 g (0.0067 mol, 1 eq) of compound 5 was dissolved in 3 mL of dry DMF, and 1.84 g (0.013 mol, 2 eq) of potassium carbonate was added to the above solution while stirring in an ice water bath, and stirring was continued for 10 min. 2.74 g (0.010 mol, 1.5 eq) of the compound 6 solution 3 mL of dry DMF was added dropwise to the above mixture. Under N2 protection, the reaction was carried out at room temperature overnight. After the reaction was completed, an appropriate amount of dichloromethane was added, and the organic phase was washed once with saturated LiCl, NH4Cl, and NaCl. The organic phase was collected and dried over anhydrous sodium sulfate.Using dichloromethane/methanol as eluent,3.3 g of a tan solid was obtained as Compound 7, yield 87.2%.

Reference： [1]Patent: CN109096170,2018,A .Location in patent: Paragraph 0123; 0142-0144

50
[ 3328-70-9 ]
[ 127-09-3 ]
N-(3-sulfonatopropyl)-2,3,3-trimethyl-3H-indolium [ No CAS ]
3-{2-[2-(3-{2-[3,3-dimethyl-1-(3-sulfopropyl)-3H-2-indoliumyl]-1-ethenyl}-4-methylcarbonyl-oxyphenyl)-1-ethenyl]-3,3-dimethyl-3H-1-indoliumyl}-1-propanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetic anhydride; at 80℃; for 1h;Inert atmosphere;	A mixture of<strong>[3328-70-9]4-hydroxybenzene-1,3-dicarbaldehyde</strong> (300 mg, 2.0 mmol), NaOAc (492 mg, 6.0mmol) and 2,3,3-trimethyl-1-(3-sulfopropyl) indolium inner salt (1152 mg, 4.1mmol) in 10 mL Ac2O was stirred for 60 minutes at 80 C under an Aratmosphere and monitored by LC-MS. After completion, the reaction mixture wasconcentrated by evaporation under reduced pressure. The acetate derivative wasdissolved in 20 mL MeOH. K2CO3 (138 mg, 1 mmol) was addedto the suspension and the reaction mixture stirred at room temperature for 60min, and monitored by LC-MS. After completion, the reaction mixture wasconcentrated by evaporation under reduced pressure. The residue was dilutedwith 4 mL H2O, 4 mL AcOH, and purified by preparative-HPLC (grad. 10-90% ACN in water, 20 min) to afford dye 3 (794 mg, 47%).

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2019,vol. 213,p. 416 - 422

51
[ 3328-70-9 ]
[ 23051-44-7 ]
2,2'-(((1E,1'E)-(4-hydroxy-1,3-phenylene)bis(ethene-2,1-diyl))bis(5,5-dimethylcyclohex-2-ene-3-yl-1-ylidene))dipropanedinitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With piperidine; In ethanol;Reflux; Inert atmosphere;	In a 25 mL round bottom flask,4-hydroxyisophthalaldehyde (0.300 g, 2 mmol) was added separately.2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile (A) (0.744 g, 4 mm)Piperidine (2d), absolute ethanol (20 mL),The reaction was refluxed for 4 h under nitrogen. Cool and remove the solvent under reduced pressure.Column chromatography with dichloromethane gave an orange-red solid in 45% yield

Reference： [1]Patent: CN109503435,2019,A .Location in patent: Paragraph 0034; 0039-0041

52
[ 3328-70-9 ]
3-(5-carboxymethyl-2,3,3-trimethyl-3H-1-indoliumyl)-1-propanesulfonate [ No CAS ]
3-(2,3,3,5-tetramethyl-3H-1-indoliumyl)-1-propanesulfonate [ No CAS ]
3-{2-[2-(3-{2-[5-carboxymethyl-3,3-dimethyl-1-(3-sulfopropyl)-2,3-dihydro-1H-2-indolyliden]ethylidene}-6-oxo-1,4-cyclohexadienyl)vinyl]-3,3,5-trimethyl-3H-1-indoliumyl}-1-propanesulfonate [ No CAS ]
3-{5-carboxymethyl-3,3-dimethyl-2-[2-(6-oxo-3-{2-[3,3,5-trimethyl-1-(3-sulfopropyl)-2,3-dihydro-1H-2-indolyliden]ethylidene}-1,4-cyclohexadienyl)vinyl]-3H-1-indoliumyl}-1-propanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%; 31%		4-Hydroxy-1,3-benzenedicarbaldehyde 1 (30 mg, 0.2 mmol) and indolenine 2a (71 mg, 0.21 mmol) and indolenine 2b (62 mg,0.21 mmol) were dissolved in acetic acid (2 mL). The reaction mixture was heated to 80 C for 5 min and sodium acetate (21 mg, 0.266 mmol)was added, the reaction mixture was stirred for 1 h at 80 C and after cooled to RT. Dark-reddish solution was poured into 100 mL diethylether and the obtained precipitate was filtered and dried in desiccator.The crude mixture of compounds D1 and D2 was separated on preparative HPLC giving D1 (35 mg, 0.047 mmol, 23%) and D2 (46 mg,0.061 mmol, 31%). D1: 1H NMR (400 MHz, DMSO-d6) delta 9.16 (d,J=1.6 Hz, 1H), 8.54 (d, J=13.6 Hz, 1H), 8.49 (d, J=13.2 Hz, 1H),8.48 (dd, J=8.8, 1.6 Hz, 1H), 8.13 (d, J=16.4 Hz, 1H), 7.99 (d,J=8.4 Hz, 1H), 7.89 (dd, J=16.4, 8.0 Hz, 2H), 7.76 (d, J=1.2 Hz,1H), 7.66 (s, 1H), 7.54 (dd, J=8.4, 1.2 Hz, 1H), 7.42 (d, J=8.2 Hz,1H), 7.19 (d, J=8.8 Hz, 1H), 4.94 (t, J=7.2 Hz, 2H), 4.87 (t,J=7.2 Hz, 2H), 3.77 (s, 2H), 2.76-2.70 (m, 2H), 2.70-2.64 (m, 2H),2.46 (s, 3H), 2.31-2.23 (m, 2H), 2.22-2.15 (m, 2H), 1.82 (s, 6H), 1.80(s, 6H). 13C NMR (100 MHz, DMSO-d6) delta 181.37, 181.00, 172.33,163.01, 152.90, 146.46, 144.11, 143.81, 139.75, 139.58, 138.77,137.10, 133.99, 130.56, 129.63, 127.12, 124.14, 123.54, 122.29,117.73, 114.98, 114.67, 111.04, 51.96, 47.18, 45.76, 45.37, 40.50,26.40, 26.12, 24.61, 21.20. MS m/z (El+) C39H44N2O9S2 calculated [M+H]+ 749.2566, found mass: 749.2567. D2: 1H NMR (400 MHz,DMSO-d6) delta 9.15 (d, J=1.2 Hz, 1H), 8.51 (d, J=16.4 Hz, 2H), 8.47(dd, J=8.8, 1.6 Hz, 1H), 8.10 (d, J=16.4 Hz, 1H), 7.96-7.88 (m, 3H),7.72 (d, J=1.2 Hz, 1H), 7.70 (s, 1H), 7.50 (dd, J=8.4, 1.2 Hz, 1H),7.46 (d, J=7.6 Hz, 1H), 7.19 (d, J=8.8 Hz, 1H), 4.90 (ABq, 4H), 3.75(s, 2H), 2.69 (ABq, 4H), 2.47 (s, 3H), 2.29-2.16 (m, 4H), 1.83 (s, 6H),1.78 (s, 6H). 13C NMR (100 MHz, DMSO-d6) . 181.50, 180.74, 172.29,163.00, 158.53, 158.15, 153.30, 146.05, 143.96, 143.84, 139.93,139.64, 138.83, 136.78, 136.64, 130.31, 129.75, 127.07, 124.02,123.51, 122.29, 117.66, 116.72, 114.96, 114.58, 113.84, 113.31,111.03, 51.98, 51.83, 47.20, 47.09, 45.69, 45.33, 40.40, 26.31, 26.08,24.67, 24.55, 21.16. MS m/z (El+) C39H44N2O9S2 calculated [M+H]+749.2566, found mass: 749.2567.

Reference： [1]Dyes and Pigments,2019,vol. 171

53
[ 3328-70-9 ]
[ 305-03-3 ]
2,4-diformylphenyl-4-[4-di(2-chloroethyl)aminophenyl]butanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With pyridine; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 5℃; for 1h;	Chlorambucil (50 mg, 0.16 mmol) was dissolved in DCM (5 mL) andDCC (33 mg, 0.16 mmol) was added to the solution. After 10 min of preactivation of CLB, the solution of phenoldialdehyde 1 (25 mg,0.167 mmol) in DCM (1 mL) with pyridine (40 TL) was added to the solution of chlorambucil. The reaction mixture was stirred at 0-5 C for 1 h. The crude conjugate was separated on preparative HPLC to give 1-CLB (25 mg, 0.057 mmol, 36%). 1H NMR (400 MHz, DMSO-d6) 1H NMR(400 MHz, CDCl3) delta 10.16 (s, 1H), 10.06 (s, 1H), 8.40 (d, J=2.0 Hz,1H), 8.16 (dd, J=8.4, 2.0 Hz, 1H), 7.37 (d, J=8.4 Hz, 1H), 7.13 (d,J=8.4 Hz, 2H), 6.68 (d, J=8.4 Hz, 2H), 3.74-3.69 (m, 4H), 3.66-3.60(m, 4H), 2.73-2.66 (m, 2H), 2.14-2.05 (m, 2H). 13C NMR (100 MHz,CDCl3) delta 190.11, 187.76, 171.29, 156.01, 144.36, 135.19, 134.41,133.08, 130.62, 129.95, 128.66, 124.75, 112.79, 53.93, 40.50, 34.00,33.52, 26.42.

Reference： [1]Dyes and Pigments,2019,vol. 171

54
[ 3328-70-9 ]
[ 34133-58-9 ]

Yield	Reaction Conditions	Operation in experiment
54.5%	With formic acid; hydroxylamine hydrochloride; sodium formate; In 1-methyl-pyrrolidin-2-one; for 6h;Reflux;	A solution of 11 (66g,0.44mol), hydroxylamine hydrochloride (91.7g, 1.32mol), HCOONa (110.7g, 1.63mol), NMP (30ml) in HCOOH (400ml) was refluxed for 6h. The reaction mixture was cooled at room temperature and stirred at 10C for 30min. Then the precipitate was filtered and recrystallized from 50% ethanol to give 12 (34.5g, 54.5%) as a gray white solid. mp: degraded at 190C. 1H NMR (600MHz, DMSO-d6) delta 12.42 (s, 1H), 8.27 (s, 1H), 7.93 (d, J=8.8Hz, 1H), 7.15 (d, J=8.8Hz, 1H). ESI-MS: m/z 142.8 [M-H] -.
3.4 g	With hydroxylamine hydrochloride; sodium formate; In 1-methyl-pyrrolidin-2-one; formic acid; for 6h;Reflux;	M-2 (66 g, 0.44 mol), hydroxylamine hydrochloride (91.7 g, 1.32 mol), sodium formate (110.7 g, 1.63 mol), NMP (30 ml) were placed in a reaction flask.Anhydrous formic acid (400 ml), refluxing for 6 h, a large amount of solid precipitated during the reaction.The reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature, stirred at 10 C for 30 min, suction filtered, and the filter cake was washed with water and dried. The obtained crude product was recrystallized from 50% ethanol to give 3.4 g of white solid, yield: 54.5 %

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 181
[2]Patent: CN110156698,2019,A .Location in patent: Paragraph 0059; 0074-0075

55
[ 50-00-0 ]
[ 90-02-8 ]
[ 3328-70-9 ]

Yield	Reaction Conditions	Operation in experiment
		In the reaction flask, salicylaldehyde (60 g, 0.39 mol), concentrated hydrochloric acid (390 ml), paraformaldehyde (24.2 g, 0.64 mol) were added, and the mixture was stirred at room temperature for 1 hour, and then phosphorus oxychloride (20 ml) was added thereto. The temperature was 0-10 C, about 1 hour, and a large amount of solids gradually precipitated, and then kept at 1 hour, and stirred at room temperature overnight. After the reaction was completed, the solid was filtered off, and the cake was washed with a 0.05% sodium hydrogen carbonate solution.The filter cake was taken and dried under vacuum at 40 C. The above crude product, HMTA (74.7 g, 0.53 mol), 280 mL of a 50% aqueous acetic acid solution was added to the reaction flask, and refluxed for 1 hour. The reaction was monitored by TLC. After the reaction was completed, 140 ml of concentrated hydrochloric acid was added and the reaction was continued for 10 min. The reaction solution was slowly poured into crushed ice, stirred for 30 min, suction filtered, and the filter cake was washed with water and dried under vacuum at 50 C to obtain 66 g of a yellow powder. The crude product obtained was used in the next reaction without purification.

Reference： [1]Patent: CN110156698,2019,A .Location in patent: Paragraph 0059; 0072-0073

56
[ 3328-70-9 ]
[ 106-95-6 ]
C₁₁H₁₀O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90.1%	With potassium carbonate; In acetonitrile; for 3h;Reflux;	A mixture of commercially available 4-hydroxyisophthalaldehyde(100 mg, 0.66 mmol), 3-bromoprop-1-ene (68 muL, 0.8 mmol) and potassiumcarbonate (120 mg, 0.86 mmol) in was dissolved in 8 mLacetonitrile and reflux for 3 h. After completion, the solvent was evaporatedunder reduced pressure, and the crude product was subjectedto column chromatography on silica gel to afforded the compound COAas white solid (118 mg, yield 90.1%). 1H NMR (500 MHz, DMSO) delta10.42 (s, 1H), 9.96 (s, 1H), 8.24 (d, J=2.2 Hz, 1H), 8.16 (dd, J=8.7,2.2 Hz, 1H), 7.44 (d, J=8.7 Hz, 1H), 6.15-6.08 (m, 1H), 5.53-5.48 (m,1H), 5.36-5.33 (m, 1H),4.88-4.87 (m, 2H).

Reference： [1]Dyes and Pigments,2019,vol. 171

57
[ 91-02-1 ]
[ 3328-70-9 ]
C₂₀H₁₄N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83.1%	With ammonium acetate; acetic acid; for 10h;Inert atmosphere; Reflux;	4-Hydroxyisophthalaldehyde (0.33 g, 4.37 mmol), ammonium acetate(0.57 g, 7.33 mmol) and phenyl(pyridin-2-yl)methanone (0.27 g,2.91 mmol) were dissolved in a solution of acetic acid (12 mL). Theresulting mixture was stirred and refluxed under argon atmospherefor 10 h. After cooling to the room temperature, the resulting solutionwas poured into 45 mL ice water. The yellow precipitate was collectedby filtration and recrystallized fromcold ethanol to afford a little yellowsolid product IPY-CHO (83.1%). 1H NMR (600 MHz, DMSO-d6) delta 11.62(s, 1H), 9.94 (s, 1H), 8.15 (d, J = 2.1 Hz, 1H), 8.04 (d, J = 9.3 Hz, 1H),7.95 (dd, J = 11.4, 4.9 Hz, 3H), 7.91 (d, J = 7.2 Hz, 1H), 7.48 (t, J =7.7 Hz, 2H), 7.30 (t, J = 7.4 Hz, 1H), 7.25 (d, J = 8.5 Hz, 1H), 7.01 (dd, J = 9.2, 6.3 Hz, 1H), 6.79 (dd, J = 10.0, 3.5 Hz, 1H). 13C NMR(150 MHz, DMSO-d6) delta 191.64, 161.39, 135.47, 135.24, 135.17, 131.92,130.42, 129.26, 129.16, 127.57, 126.68, 126.39, 124.72, 121.36, 118.71,117.86, 117.35, 113.25. HRMS (EI) m/z calcd for [C20H14N2O2-H]+:313.0977, Found: 313.0999.

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2020,vol. 225

58
[ 3328-70-9 ]
[ 99-98-9 ]
(E)-4-((4-(dimethylamino)phenylimino)methyl)-3-hydroxybenzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	In ethanol; at -30℃;	To a solution of compound 2 (0.15 g, 1.0 mmol) in absoluteethanol, add a solution of N,N-dimethylbenzene-1,4-diamine(0.14 g, 1.0 mmol) in ethanol slowly in a drop-wisemanner (within a period of 20 min) at 30 C and allow it tostand for 30e40 min. The course of the reaction was monitored bythin layer chromatography (TLC) assay until completion. A rustsolidwas precipitated, collected, and washed with ethanol to affordcompound 1. Yield: 0.12 g, 45%.1H NMR (CDCl3, 400 MHz) d (ppm)14.9 (s, 1H), 9.90 (s, 1H), 8.70 (s, 1H), 7.93 (d, J 2.0 Hz, 1H), 7.86 (dd,J 2.0 Hz, J 8.0 Hz, 1H), 7.33 (d, J 8.8 Hz, 2H), 7.10 (d, J 8.8 Hz,1H), 6.78 (d, J 8.4 Hz, 2H), 3.04 (s, 6H); 13C NMR (CDCl3, 100 MHz)d (ppm): 190.14, 167.20, 155.80, 150.28, 134.13, 133.42, 128.18,122.29, 119.44, 118.27, 112.67, 40.52. HRMS-ESI: m/z calcd (%) forC16H17N2O2: 269.1290 [MH]; Found: 269.1296 (Figs. S1e2,Supporting information). Crystal data for C16H16N2O2: Crystal:monoclinic, space group P1 21/n1. a 15.21 (5) A, b 4.772 (16) A,c 19.39 (6) A, V 1404 (8) A3, Z 4, T 296.15 K, max 24.25,5920 reflections measured. Final R indices (I > 2s(I)): R1 0.1062(728), wR2 0.3561 (2271). CCDC number: 1902319.

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2020,vol. 226

59
[ 3328-70-9 ]
[ 73289-79-9 ]

Reference： [1]Dyes and Pigments,2020,vol. 172

60
[ 2680-03-7 ]
[ 3328-70-9 ]
4-hydroxy-3-methyl-2-oxo-2H-chromene-6-carbaldehyde [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 9275 - 9279

61
[ 3328-70-9 ]
[ 120506-39-0 ]
C₂₁H₂₆O₄Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%		Intermediate 7 (0.3 g, 2 mmol) and potassium carbonate (0.55 g, 4 mmol) were dissolved in 5 mL dry DMF.After stirring at room temperature for 30 min, the compound 11 was added to the reaction system and allowed to react overnight.After the reaction was completed, the reaction solution was poured into water and extracted with dichloromethane (30 mL×3).The combined organic layers were dried with anhydrous magnesium sulfate, filtered and evaporatedThe crude product obtained was purified by silica gel column chromatography (ethyl acetate: petroleum ether = 1:10)A pale yellow oily liquid 12 (0.40 g, 1.08 mmol, 54%).

Reference： [1]Patent: CN110372742,2019,A .Location in patent: Paragraph 0014; 0027; 0032

62
[ 3328-70-9 ]
[ 84161-87-5 ]
2,4-bis(((4'-(diphenylamino)-[1,1'-biphenyl]-4-yl)imino)methyl)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate; In water; acetonitrile; at 120℃; for 24h;	(1) 1,680 mg of N, N-diphenyl- [1,1'-biphenyl] -4,4'-diamine was dissolved in 500 mL of acetonitrile, and the mixture was stirred with ultrasound to obtain solution 1; (2) Dissolve 150 mg of 4-hydroxyisophthalaldehyde in 100 mL of acetonitrile and stir uniformly with ultrasound to obtain solution 2; (3) Dissolve 1380 mg of potassium carbonate in deionized water and stir with ultrasound to obtain a 6 mol / L potassium carbonate aqueous solution; (4) The solution 1 in step (1) and the solution 2 in step (2) are mixed uniformly, and a 6 mol / L potassium carbonate aqueous solution prepared in step (3) is added dropwise thereto, and the vacuum is filled with nitrogen to carry out The reaction was heated and the reaction temperature was controlled at 120 C. After 24 hours of reaction, the reaction was stopped. After cooling to room temperature, it was separated and purified to obtain 707.4 mg of orange-yellow powder 2,4-bis (((4 '-(diphenylamino)- [1,1'-Biphenyl] -4-yl) imino) methyl) phenol, that is, the fluorescent compound (BTPAP) for isocyanate detection, with a yield of 90%.

Reference： [1]Patent: CN110330444,2019,A .Location in patent: Paragraph 0048-0068

63
[ 3328-70-9 ]
[ 1379114-86-9 ]
C₂₃H₂₃N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72.5%	With potassium carbonate; In N,N-dimethyl-formamide; at 50 - 100℃;	a. The intermediate and p-hydroxy-m-xylene in Example 1 (1: 1 to 3n: n)Mixed with anhydrous potassium carbonate in anhydrous DMF (N, N-dimethylformamide),The reaction was completed at 50-100 C. After cooling to room temperature, the mixture was extracted with an organic solvent, washed, dried, filtered, and the concentrated crude product was purified by silica gel column chromatography to obtain intermediate 5. The yield was 72.5%.

Reference： [1]Patent: CN110305111,2019,A .Location in patent: Paragraph 0057; 0058

64
[ 3328-70-9 ]
C₂₄H₂₇BrN₄O₂ [ No CAS ]
C₃₂H₃₂N₄O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37.5%	With caesium carbonate; In acetonitrile; at 80℃;Inert atmosphere;	Compound 3 (0.24 mmol, 0.1156 g) and 4-hydroxyisophthalaldehyde (0.24 mmol, 0.036 g) were dissolved in 5 mL of acetonitrile, and cesium carbonate (0.36 mmol, 0.117 g) was added.The above mixture was refluxed overnight at 80 C under N2 protection.After the reaction was completed, the solution was concentrated by rotary evaporation, and separated through a column with dichloromethane: methanol = 15: 1.Compound 4 was obtained as a yellow oil with a yield of 37.5%.

Reference： [1]Analytical Chemistry,2020,vol. 92,p. 1245 - 1251
[2]Patent: CN110563702,2019,A .Location in patent: Paragraph 0043; 0057-0059

65
[ 60512-56-3 ]
[ 3328-70-9 ]
4-oxo-2-p-tolyl-4H-chromene-6-carbaldehyde [ No CAS ]

Reference： [1]Organic and biomolecular chemistry,2020,vol. 18,p. 1402 - 1411

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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

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. 3328-70-9 ] {[proInfo.proName]}

Quality Control of [ 3328-70-9 ]

Related Doc. of [ 3328-70-9 ]

Product Details of [ 3328-70-9 ]

Calculated chemistry of [ 3328-70-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 3328-70-9 ]

Application In Synthesis of [ 3328-70-9 ]

[ 3328-70-9 ] Synthesis Path-Upstream 1~3

[ 3328-70-9 ] Synthesis Path-Downstream 1~65

Related Functional Groups of [ 3328-70-9 ]

Aryls

Aldehydes

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 3328-70-9 ]