[ CAS No. 7325-46-4 ] {[proInfo.proName]}

Name: 7325-46-4|2,2'-(1,4-Phenylene)diacetic acid|97%
Brand: Ambeed
SKU: A280934
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Quality Control of [ 7325-46-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 7325-46-4 ]

CAS No. :	7325-46-4	MDL No. :	MFCD00004354
Formula :	C₁₀H₁₀O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SLWIPPZWFZGHEU-UHFFFAOYSA-N
M.W :	194.18	Pubchem ID :	81760
Synonyms :

Calculated chemistry of [ 7325-46-4 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.2
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	49.53
TPSA :	74.6 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.8 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.73
Log Po/w (XLOGP3) :	0.96
Log Po/w (WLOGP) :	0.94
Log Po/w (MLOGP) :	1.28
Log Po/w (SILICOS-IT) :	1.32
Consensus Log Po/w :	1.05

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.7
Solubility :	3.86 mg/ml ; 0.0199 mol/l
Class :	Very soluble
Log S (Ali) :	-2.11
Solubility :	1.49 mg/ml ; 0.00769 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.96
Solubility :	2.14 mg/ml ; 0.011 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.12

Safety of [ 7325-46-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 7325-46-4 ]

* 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 [ 7325-46-4 ]
Downstream synthetic route of [ 7325-46-4 ]

[ 7325-46-4 ] Synthesis Path-Upstream 1~14

1
[ 201230-82-2 ]
[ 623-25-6 ]
[ 7325-46-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: With C₂₈H₁₆N₂O₆Se In butan-1-ol for 2 h; Reflux Stage #2: With tetrabutylammomium bromide; sodium hydroxide In butan-1-ol at 50℃; for 24 h;	General procedure: 1 mmol of the selenium-containing catalyst prepared in Example 1 and 20 mL of n-butanol were placed in the flask, and air was discharged through carbon monoxide. The pressure was 0.1 MPa at a carbon monoxide, and the mixture was heated under reflux for 2 hours to activate the catalyst. After completion of the reaction, 20 mmol of benzyl chloride, 25 mL of 15percent sodium hydroxide solution, 0.05 mmol of tetrabutylammonium bromide, and carbon monoxide were discharged to the air, and the reaction was carried out for one day under the conditions of a carbon monoxide pressure of 0.1 MPa and a temperature of 50 °C. After completion of the reaction, the aqueous phase in the reaction mixture was separated using a sep. funnel, and the organic phase was washed with water (15 mL×3). The aqueous phase and the washing liquid were combined, and concentrated to 15 mL by heating. After cooling, hydrochloric acid was added to adjust the pH of the solution to 2. The resulting solution was frozen at a temperature below 5 ° C for 12 hours, suction filtered, and dried to give phenylacetic acid in a yield of 92percent. With the embodiment 2 similar, the difference lies in that: the raw material benzyl chloride was changed to benzyl dichloride, phenylenediacetic acid to be 2.55 g, yield 90percent.
80%	Stage #1: With C₂₈H₂₂CoN₄O₆ In butan-1-ol at 60℃; for 2 h; Glovebox; High pressure; Green chemistry Stage #2: With tetra-(n-butyl)ammonium iodide; sodium hydroxide In butan-1-ol at 60℃; for 22 h; Glovebox; High pressure; Green chemistry	General procedure: A 100 mL reactor equipped with Teflon-coated magnetic stir bars was charged with n-Butyl alcohol (20 mL) and the catalyst (0.5 mmol). The reactor was then taken out of the glove box and pressured with carbon monoxide (1 atm). The mixture was stirred 2 h at 60 °C, cooled to ambient temperature and slowly vented. After benzyl chloride (10 mmol), NaOH (15 mL, 15percent), and TBAI (0.25 mmol) were added, the reactor was sealed and the reaction mixtures were stirred for 22 h at 60 °C under carbon monoxide (1 atm). After the reaction, the water phase was detached and washing the organic phase three times with H₂O (3×5 mL), the combined water layer was washed with Et₂O, then the resulting solution was cooled to 0 °C and adjusted to pH=1–2 with HCl (6 mol/L). The product was filtered, dried in RT, and then recrystallized.

Reference： [1] Patent: CN108250155, 2018, A, . Location in patent: Paragraph 0019; 0020; 0025; 0026
[2] Tetrahedron, 2013, vol. 69, # 35, p. 7264 - 7268

2
[ 201230-82-2 ]
[ 589-29-7 ]
[ 106-42-3 ]
[ 7325-46-4 ]
[ 622-47-9 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1998, vol. 71, # 3, p. 723 - 734

3
[ 623-24-5 ]
[ 201230-82-2 ]
[ 7325-46-4 ]

Reference： [1] Tetrahedron Letters, 2000, vol. 41, # 40, p. 7601 - 7604

4
[ 622-75-3 ]
[ 7325-46-4 ]

Reference： [1] Monatshefte fur Chemie, 2003, vol. 134, # 8, p. 1159 - 1166
[2] Green Chemistry, 2011, vol. 13, # 10, p. 2888 - 2894
[3] Chemische Berichte, 1876, vol. 9, p. 1767
[4] Chemische Berichte, 1876, vol. 9, p. 1767
[5] Chemische Berichte, 1872, vol. 5, p. 703
[6] Journal of the Chemical Society, 1888, vol. 53, p. 41[7] Chemische Berichte, 1888, vol. 21, p. 42
[8] Bulletin of the Chemical Society of Japan, 1973, vol. 46, # 1, p. 270 - 275

5
[ 201230-82-2 ]
[ 589-29-7 ]
[ 7325-46-4 ]
[ 622-47-9 ]

Reference： [1] Tetrahedron Letters, 1997, vol. 38, # 21, p. 3747 - 3750

6
[ 36076-26-3 ]
[ 113520-36-8 ]
[ 7325-46-4 ]

Reference： [1] Patent: WO2017/132432, 2017, A1, . Location in patent: Paragraph 00183

7
[ 36076-26-3 ]
[ 7325-46-4 ]

Reference： [1] Chemical & Pharmaceutical Bulletin, 1985, vol. 33, # 12, p. 5310 - 5315

8
[ 106-42-3 ]
[ 7325-46-4 ]

Reference： [1] Journal of the American Chemical Society, 1943, vol. 65, p. 1339,1345

9
[ 623-25-6 ]
[ 7325-46-4 ]

Reference： [1] Monatshefte fur Chemie, 2003, vol. 134, # 8, p. 1159 - 1166
[2] Bulletin of the Chemical Society of Japan, 1973, vol. 46, # 1, p. 270 - 275

10
[ 105077-01-8 ]
[ 7325-46-4 ]

Reference： [1] Chemical & Pharmaceutical Bulletin, 1985, vol. 33, # 12, p. 5310 - 5315

11
[ 7398-52-9 ]
[ 7325-46-4 ]

Reference： [1] Journal of Organic Chemistry, 1946, vol. 11, p. 798,800

12
[ 1528-42-3 ]
[ 7325-46-4 ]

Reference： [1] Journal of Organic Chemistry, 1946, vol. 11, p. 798,800

13
[ 111-65-9 ]
[ 106-42-3 ]
[ 1822-71-5 ]
[ 7325-46-4 ]
[ 622-47-9 ]
[ 142-62-1 ]

Reference： [1] Journal of the American Chemical Society, 1943, vol. 65, p. 1339,1345

14
[ 7325-46-4 ]
[ 539-48-0 ]

Reference： [1] Zhurnal Obshchei Khimii, 1956, vol. 26, p. 1130,1132; engl. Ausg. S. 1283, 1285

[ 7325-46-4 ] Synthesis Path-Downstream 1~83

1
[ 622-75-3 ]
[ 7325-46-4 ]

Reference： [1]Monatshefte fur Chemie,2003,vol. 134,p. 1159 - 1166
[2]Green Chemistry,2011,vol. 13,p. 2888 - 2894
[3]Chemische Berichte,1876,vol. 9,p. 1767
[4]Chemische Berichte,1876,vol. 9,p. 1767
[5]Journal of the Chemical Society,1888,vol. 53,p. 41
Chemische Berichte,1888,vol. 21,p. 42
[6]Bulletin of the Chemical Society of Japan,1973,vol. 46,p. 270 - 275

2
[ 7325-46-4 ]
[ 21062-19-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With Vilsmeier reagent; In toluene; at 35 - 40℃; for 0.25h;	5.8 g (45.3 mmol) of Vilsmeier reagent was suspended in 40 mL of toluene, 3.88 g (20 mmol) of 1,4-benzenediacetic acid was added, and the mixture was stirred at 35-40 C. for 15 minutes. The toluene solution was separated, and toluene was distilled off under reduced pressure to obtain pale yellow crystals of the corresponding acid chloride 4.48 g (crude yield 97.4%).This was recrystallized from 40 mL of cyclohexane to obtain 4.0 g (87%) of 1,4-benzenediacetyl chloride.
	With thionyl chloride; for 5h;Reflux;	24.51 g (205.99 mmol) of thionyl chloride was added to 10.0 g (51.50 mmol) of 1 ,4-phenylene acetate, and was stirred for 5 hours with heating under reflux. After thereaction was completed, non-reacted thionyl chloride was distilled oil under reduced pressure to obtain the target di(acid chloride) as a colorless needle. A solution (300 ml) of 11.90 g (51.50 mmol) of the resulting di(acid chloride) in chloroform was cooled to -78 C., and 13.10 g (102.99 mmol) of 2-mercaptopyridine N-oxide was added. 8.35 g (105.57 mmol) of pyridine was added dropwise at the same temperature as above, and yellow crystals were then precipitated during the process to raise the temperature to 0 C. The crystals were separated through filtration, were washed with chloroform, and were dried to obtain 12.66 g of the target bis Barton ester (2 steps, yield: 60%) represented by the above formula (7) as light yellow crystals

Reference： [1]Patent: JP6088890,2017,B2 .Location in patent: Paragraph 0056
[2]Chemische Berichte,1958,vol. 91,p. 1775,1780
[3]Gazzetta Chimica Italiana,1957,vol. 87,p. 215,218, 221
Rend. Ist. super. Sanita,1955,vol. 18,p. 983,986, 990
[4]Bulletin of the Chemical Society of Japan,1973,vol. 46,p. 270 - 275
[5]Journal of the Chemical Society. Perkin Transactions 2 (2001),1996,vol. 0,p. 2297 - 2302
[6]Tetrahedron,2001,vol. 57,p. 4987 - 4993
[7]Journal of Organic Chemistry,2003,vol. 68,p. 8149 - 8156
[8]Journal of Medicinal Chemistry,2007,vol. 50,p. 5655 - 5664
[9]Synthesis,2007,p. 3406 - 3410
[10]Chemistry and Physics of Lipids,2008,vol. 155,p. 98 - 113
[11]Organic and Biomolecular Chemistry,2016,vol. 14,p. 1455 - 1472
[12]MedChemComm,2017,vol. 8,p. 320 - 328
[13]Patent: US2017/130028,2017,A1 .Location in patent: Paragraph 0197
[14]Angewandte Chemie - International Edition,2018,vol. 57,p. 6475 - 6479
Angew. Chem.,2018,vol. 130,p. 6585 - 6589,5

3
[ 7325-46-4 ]
[ 68-12-2 ]
1,4-bis[(1-dimethylamino-3-dimethyliminium)prop-2-en-2-yl]benzene bis(perchlorate) [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2020,vol. 57,p. 2428 - 2432
[2]Chemische Berichte,1969,vol. 102,p. 2301 - 2318
[3]Collection of Czechoslovak Chemical Communications,1965,vol. 30,p. 2783 - 2792

4
[ 7325-46-4 ]
[ 4151-33-1 ]
[ 104595-25-7 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic anhydride Heating;

Reference： [1]Fields, E. K.; Behrend, S. J.; Meyerson, S.; Winzenburg, M. L.; Ortega, B. R.; Hall, H. K. [Journal of Organic Chemistry, 1990, vol. 55, # 17, p. 5165 - 5170]

5
[ 7325-46-4 ]
[ 5140-03-4 ]

Yield	Reaction Conditions	Operation in experiment
87%		To a stirred solution of (4-carboxymethylphenyl)acetic acid (1.0 g, 5.15 mmol) in THF (100 mL) was slowly added borane dimethyl sulfide (2.3 mL, 30.9 mmol) and the resulting mixture was stirred overnight (18 hours). The reaction was then quenched by slowly adding 1N HCl (100 mL). The resulting mixture was then extracted with EtOAc (3×100 mL). The combined organic layers were washed with saturated NaCl (1×100 mL), dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to provide 750 mg of the title intermediate (87% yield), which was used without further purification.
81.8%	With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20℃; for 24h;Inert atmosphere;	Into a 1.0-L round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 2-[4-(carboxymethyl)phenyl]acetic acid (40 g, 200 mmol) in THF (500 mL). This was followed by the addition of BH3-Me2S (60 mL, 600 mmol, 10 M) dropwise with stirring at 0C . The resulting solution was stirred for 24 h at RT. The reaction was then quenched by the addition of 200 mL of water. The resulting solution was extracted with 2x150 mL of ethyl acetate. The organic layers combined and dried over anhydrous Na2S04, then concentrated. The residue was eluted from a silica gel column with ethyl acetate/petroleum ether (1 : 10 to 1 :3). This resulted in 28 g (81.8%) of the title compound as brown oil. MS-ESI: 167 (M+l).

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 1210 - 1217
[2]Patent: US2005/203167,2005,A1 .Location in patent: Page/Page column 21
[3]Patent: WO2019/23147,2019,A1 .Location in patent: Page/Page column 518
[4]Organic Letters,2019,vol. 21,p. 8404 - 8408
[5]Journal of Organic Chemistry,2006,vol. 71,p. 236 - 243
[6]Patent: US8003633,2011,B1
[7]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 4900 - 4910

6
[ 36076-26-3 ]
[ 7325-46-4 ]

Reference： [1]Chemical and pharmaceutical bulletin,1985,vol. 33,p. 5310 - 5315

7
[ 7325-46-4 ]
[ 82072-23-9 ]
[ 191276-45-6 ]

Reference： [1]Tetrahedron,1997,vol. 53,p. 6755 - 6790

8
[ 201230-82-2 ]
[ 589-29-7 ]
[ 7325-46-4 ]
[ 622-47-9 ]

Reference： [1]Tetrahedron Letters,1997,vol. 38,p. 3747 - 3750

9
[ 201230-82-2 ]
[ 589-29-7 ]
[ 106-42-3 ]
[ 7325-46-4 ]
[ 622-47-9 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1998,vol. 71,p. 723 - 734

10
[ 623-24-5 ]
[ 201230-82-2 ]
[ 7325-46-4 ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 7601 - 7604

11
[ 7325-46-4 ]
[ 1143-38-0 ]
{4-[2-(4,5-dihydroxy-10-oxo-9,10-dihydro-anthracen-9-yl)-2-oxo-ethyl]-phenyl}-acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%	With pyridine; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In tetrahydrofuran at 50℃; for 2h;

Reference： [1]Müller; Reindl; Breu [Journal of Medicinal Chemistry, 2001, vol. 44, # 5, p. 814 - 821]

12
[ 7325-46-4 ]
2,3-dihydro-1<i>H</i>-isoindole-5,6-dicarboxylic acid 5-[2-(4-fluoro-phenyl)-ethyl]-amide} 6-(4-methyl-benzylamide) [ No CAS ]
C₆₂H₅₈F₂N₆O₆ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 544 - 555

13
[ 64-17-5 ]
[ 7325-46-4 ]
[ 36076-26-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sulfuric acid; at 80℃;	Step 1: (0447) The reaction flask was charged with 2,2?-(1,4-phenylene)diacetic acid 30-a (9.2 g, 47.4 mmol) and ethanol (50 ml), concentrated sulfuric acid (5 ml, 94.8 mmol) was slowly added dropwise under stirring. The mixture was stirred at 80 C. overnight and then concentrated under reduced pressure to remove ethanol. Dichloromethane was added and the pH value of the aqueous layer was adjusted to 8 with saturated sodium bicarbonate solution. The aqueous phase was separated and extracted again with dichloromethane. The combined organic phase was dried and concentrated to give 30-b as solid (10.3 g, yield: 87%). ESI-MS (m/z): 251.2 [M+H]+.
	acetyl chloride; for 18h;Heating / reflux;	2,2'-(1,4-phenylene)diacetic acid (10.0 g, 51 mmol) was dissolved in ethanol (100 ml) and the solution treated dropwise with catalytic acetyl chloride (2.5 ml). The reaction mixture was stirred at reflux for 18 hours before being allowed to cool and concentrated in vacuo. The residue was taken up in ethyl acetate (100 ml) and extracted with sodium bicarbonate solution (3×50 ml) and brine (3×50 ml). The organic phase was then dried (magnesium sulphate) and concentrated in vacuo. The residue was triturated with pentane to yield the title product, 11.8 g. 1HNMR (CDCl3, 400 MHz) delta: 1.26 (t, 6H), 3.57 (s, 4H), 4.12 (q, 4H), 7.21 (m, 4H) MS (electrospray): m/z 273 [M+H]+

Reference： [1]Organic Letters,2010,vol. 12,p. 4364 - 4367
[2]Patent: US2017/158680,2017,A1 .Location in patent: Paragraph 0445; 0446; 0447
[3]Journal of Organic Chemistry,2006,vol. 71,p. 236 - 243
[4]Patent: US2005/171147,2005,A1 .Location in patent: Page/Page column 19

14
[ 58-27-5 ]
[ 7325-46-4 ]
[ 909778-31-0 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 10784 - 10794

15
[ 909778-29-6 ]
[ 7325-46-4 ]
[4-(3-fluoromethyl-2-ylmethyl-1,4-naphtoquinone)-phenyl]-acetic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 10784 - 10794

16
[ 7325-46-4 ]
[ 1036248-62-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: POCl₃ / 4 h / 90 - 95 °C 1.2: 79.5 percent / NaClO₄; water 2.1: aq. NaOH / Heating 2.2: aq.HCl / 20 °C / pH 5 3.1: 3.22 g / hydrazine hydrate / aq. HCl / 20 °C / pH 5

Reference： [1]Lozan, Vasile; Solntsev, Pavlo Y.; Leibeling, Guido; Domasevitch, Konstantin V.; Kersting, Berthold [European Journal of Inorganic Chemistry, 2007, # 20, p. 3217 - 3226]

17
[ 7325-46-4 ]
[ 39246-00-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylsilane; tris(pentafluorophenyl)borate; In benzene; at 23℃; for 6h;Schlenk technique; Inert atmosphere;	A Schlenk tube equipped with a magnetic stir bar was charged with 1,4-benzenediacetic acid (9.7 g, 50.0 mmol) and tris(pentafluorophenyl)borane (1.3 mg, 2.5 mumol). Then 50 mL of benzene (C6H6) was added under argon. Then, triethylsilane (17.52 g / 28.75 mL, 180.0 mmol) was added dropwise at 23 C.After 6 hours of reaction, all volatiles (including solvent and excess triethylsilane) were removed under vacuum to give a crude material.Add 200 mL of tetrahydrofuran solvent to the crude product, then add 200 mL of hydrochloric acid solution (1 mM).After the completion of the stirring, further stirring was continued at room temperature for 3 hours, and extracted three times with 300 mL of ethyl acetate.The organic phase was washed with brine and dried over magnesium sulfate.The organic layer was dried with anhydrous MgSO4, filtered and evaporated.The concentrated product was purified on a silica gel column (200-300 mesh), eluent, ethyl acetate:hexanehexane = 1:1 (v: v),Concentrate the eluent,A white solid 7.2 g of 1,4-benzenediacetaldehyde was obtained in a yield of 90%.

Reference： [1]Patent: CN109721477,2019,A .Location in patent: Paragraph 0023; 0024; 0025; 0026; 0027
[2]Journal of Organic Chemistry,2006,vol. 71,p. 236 - 243

18
[ 7325-46-4 ]
[ 36076-26-3 ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 8149 - 8156

19
[ 64-17-5 ]
[ 7325-46-4 ]
[ 36076-26-3 ]
[ 113520-36-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; water; In 1,4-dioxane; for 18h;Heating / reflux;	A solution of the diester from preparation 9 (11.8 g, 47.0 mmol) and 2,2'-(1,4-phenylene)diacetic acid (15.73 g, 81.0 mmol) in ethanol (6.14 ml) and dioxan (75 ml) was treated dropwise with 12M hydrochloric acid (1.57 ml, 18.8 mmol). The reaction mixture was stirred at reflux for 18 hours before being allowed to cool and concentrated to low volume. The reaction mixture was diluted with toluene (125 ml) and the resulting slurry filtered. The filtrate was concentrated in vacuo and the residue taken up in water and basified with sodium bicarbonate until pH neutral. The mixture was diluted with ethyl acetate (200 ml) and the organic layer was separated and washed with sodium bicarbonate solution (5×30 ml) and sat. aq. sodium chloride (50 ml). The combined aqueous extracts were acidified to pH 3 with 6M hydrochloric acid and extracted with ether (3×30 ml). The organics were combined, dried (magnesium sulphate) and concentrated in vacuo. The residue was triturated with pentane giving the title compound as a colourless solid 10.8 g. 1HNMR (CD3OD, 400 MHz) delta: 1.23 (t, 3H), 3.56 (m, 2H), 3.60 (m, 2H), 4.10 (q, 2H), 7.22 (m, 4H) ppm. MS (electrospray): m/z 245 [MNa]+

Reference： [1]Patent: US2005/171147,2005,A1 .Location in patent: Page/Page column 20

20
[ 7325-46-4 ]
[ 103-67-3 ]
[ 864846-89-9 ]

Yield	Reaction Conditions	Operation in experiment
		To a 2-L three-necked flask, equipped with a magnetic stir bar, nitrogen gas inlet and addition tunnel, was added <strong>[7325-46-4]1,4-phenylenediacetic acid</strong> (50 g, 257 mmol), PyBOP (127.5 g, 245 mmol) and DCM (700 mL). The reaction mixture was then cooled to 0 C. to 10 C. A solution of benzylmethylamine (34.81 mL, 269.7 mmol) and DIPEA (85.4 mL, 490 mmol) in DCM (300 mL) was then added slowly and the reaction mixture was stirred at ambient temperature overnight (16 hours). The reaction mixture was then washed with water (2×200 mL) and the organic phase was concentrated under reduced pressure. The pH of the resulting mixture was adjusted with 1N NaOH to pH 10 and the mixture was then extracted with MTBE. The aqueous phase was cooled to 0 C. to 5 C. and the pH of the aqueous phase was adjusted to pH 3 by adding 1N HCl. The resulting mixture was extracted with DCM and the combined DCM layers were washed with water (1×100 mL), brine (1×100 mL), dried over sodium sulfate and concentrated under vacuum to afford 38 g of the title intermediate (90% purity). MS m/z: [M+H+] calc'd for C18H19NO3 298.1; found 298.3.

Reference： [1]Patent: US2005/203167,2005,A1 .Location in patent: Page/Page column 18

21
[ 7325-46-4 ]
[ 36076-25-2 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; sodium hydrogencarbonate; In methanol;	(18-1) Dimethyl 1,4-phenylenediacetate Under ice cooling, thionyl chloride (6.6 ml) was added dropwise into methanol (26 ml) and the resultant mixture was stirred for 15 min. Next, <strong>[7325-46-4]1,4-phenylenediacetic acid</strong> (5.0 g) was added thereto and the resultant mixture was stirred at room temperature for 35 hr and then concentrated under reduced pressure. Then it was diluted with ethyl acetate (500 ml) washed with a saturated aqueous solution of sodium bicarbonate and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound as colorless crystals. 1H-NMR (400 MHz, CDCl3): delta(ppm) 3.61(4H, s), 3.69(6H, s), 7.25(4H, d, J=6.4Hz).

Reference： [1]Patent: US2002/19531,2002,A1

22
[ 74124-79-1 ]
[ 7325-46-4 ]
N,N'-Bis[3-(3-((1 R)-1-((2S)-(3,3-dimethyl-1,2-dioxopentyl)piperidine-2-carbonyloxo)-3-phenyl)propylphenoxy)propyl] 1,4-phenylenediacetamide [ No CAS ]
[ 178446-62-3 ]

Yield	Reaction Conditions	Operation in experiment
37%	With pyridine; In acetonitrile;	Example 1 N,N'-Bis[3-(3-((1 R)-1-((2S)-(3,3-dimethyl-1,2-dioxopentyl)piperidine-2-carbonyloxo)-3-phenyl)propylphenoxy)propyl] 1,4-phenylenediacetamide (31) A mixture of <strong>[7325-46-4]1,4-phenylenediacetic acid</strong> (194 mg, 1.0 mmol) and disuccinimidyl carbonate (512 mg, 2.0 mg) in anhydrous acetonitrile (5.0 mL) was treated with pyridine (243 mL, 3.0 mmol). The mixture was stirred at room temperature under nitrogen overnight. The resulting suspension was partitioned between EtOAc (70 mL) and water (50 mL). The organic layer was separated, washed with 1 M Na2 CO3, water, 0.5 N HCl, saturated brine, dried (Na2 SO4), and concentrated in vacuo to give disuccinimidyl 1,4-phenylenediacetate (144 mg, 37%) as a white solid. 1 H NMR (DMSO-d6, 300 MHz) 7.34 (s, 4H), 4.10 (s, 4H), 2.80 (s, 8 H).

Reference： [1]Patent: US6150527,2000,A

23
[ 74124-79-1 ]
[ 7325-46-4 ]
N,N'-Bis[3-(3-((1R)-1-((2S)-(3,3-dimethyl-1,2-dioxopentyl)piperidine-2-carbonyloxo)-3-phenyl)propylphenoxy)propyl] 1,4-phenylenediacetamide [ No CAS ]
[ 178446-62-3 ]

Yield	Reaction Conditions	Operation in experiment
37%	With pyridine; In acetonitrile;	EXAMPLE 1 N,N'-Bis[3-(3-((1R)-1-((2S)-(3,3-dimethyl-1,2-dioxopentyl)piperidine-2-carbonyloxo)-3-phenyl)propylphenoxy)propyl] 1,4-phenylenediacetamide (31) A mixture of <strong>[7325-46-4]1,4-phenylenediacetic acid</strong> (194 mg, 1.0 mmol) and disuccinimidyl carbonate (512 mg, 2.0 mg) in anhydrous acetonitrile (5.0 mL) was treated with pyridine (243 muL, 3.0 mmol). The mixture was stirred at room temperature under nitrogen overnight. The resulting suspension was partitioned between EtOAc (70 mL) and water (50 mL). The organic layer was separated, washed with 1 M Na2 CO3, water, 0.5 N HCl, saturated brine, dried (Na2 SO4), and concentrated in vacuo to give disuccinimidyl 1,4-phenylenediacetate (144 mg, 37%) as a white solid. 1 H NMR (DMSO-d6, 300 MHz) 7.34 (s, 4 H), 4.10 (s, 4 H), 2.80 (s, 8 H).

Reference： [1]Patent: US6133456,2000,A

24
[ 7325-46-4 ]
[ 99469-97-3 ]
4-[(1-(2-Piperidino-phenyl)-1-butyl)-aminocarbonylmethyl]-phenyl-acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; thionyl chloride; In dichloromethane;	Example 75 4-[(1-(2-piperidino-phenyl)-1-butyl)-aminocarbonylmethyl]-phenylacetic acid Three grams (15.45 m mol) of p-phenylene-diacetic acid and 10 ml of thionyl chloride were refluxed for 90 minutes and then concentrated by evaporation in vacuo. The crude diacid chloride was dissolved in 100 ml of methylene chloride. Then, a solution of 3.6 gm (15.45 m mol) of 1-(2-piperidino-phenyl)-1-butylamine was slowly added dropwise to this solution, under stirring, at an internal temperature of 10 to 15 C. After two hours at ambient temperature, the mixture was concentrated by evaporation in vacuo, and the evaporation residue was distributed between 100 ml of ice-cold 5% sodium hydroxide solution and ethyl acetate. It was filtered through kieselguhr, and the organic phase was separated off. The alkaline-aqueous phase was adjusted to a pH of 5.5 with semi-concentrated hydrochloric acid and extracted with ethyl acetate. The extract was dried over sodium sulfate and filtered, and the filtrate was concentrated by evaporation in vacuo. The evaporation residue was purified by column chromatography on silica gel [chloroform/methanol (20:1)]. Yield: 0.10 gm (1.6% of theory), M.p.: 136-140 C. (acetonitrile/ether)

Reference： [1]Patent: US4735959,1988,A

25
[ 67-56-1 ]
[ 7325-46-4 ]
[ 36076-25-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sulfuric acid;Reflux;	2,2'-(1,4-Phenylene)diacetic acid (200 mg, 1.0 mmol), methanol (10 mL), concentrated sulfuric acid (1 mL) were added in a 25 mL single-neck flask, and the mixture was heated to reflux overnight. After the materials had all reacted when being determined by TLC, saturated aqueous solution of sodium carbonate was added to neutralize the solution, and the mixture was extracted with ethyl acetate to obtain a crude product (white solid, 230 mg), with a yield of 100%.
90%	With sulfuric acid; at 80℃; for 94h;Inert atmosphere;	A solution of <strong>[7325-46-4]1,4-phenylenediacetic acid</strong> (13) (10.44 g, 54 mmol) in MeOH (50 mL) was treated dropwise with conc. H2SO4 (5 mL) under N2 atmosphere. The clear solution was stirred at 80 C for 94 h. After evaporation, the residue was dissolved in CH2Cl2 (50 mL). The pH of the solution was adjusted to approximately pH = 7 with a sat. aq. NaHCO3 solution. H2O (20 mL) was added, and the aq. layer was extracted with CH2Cl2 (3 x 50 mL). The combined organic layers were dried over MgSO4, filtered, and evaporated affording 14 (10.8 g, 90%), which was obtained as a white crystalline solid.
	With sulfuric acid;Reflux;	Methyl ester 5 is prepared as reported in the literature by refluxing phenylenediacetic acid with methanol and H/SO4 in catalytic amount (Whitmore, F. C., et al., J. Am. Chem. Soc. 1938, 60, 2790).

Reference： [1]Patent: EP3581561,2019,A1 .Location in patent: Paragraph 0132-0133
[2]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 4900 - 4910
[3]Chemical Science,2018,vol. 9,p. 8930 - 8936
[4]Patent: US8003633,2011,B1 .Location in patent: Page/Page column 19
[5]Angewandte Chemie - International Edition,2018,vol. 57,p. 10357 - 10361
Angew. Chem.,2018,vol. 130,p. 10514 - 10518,5
[6]Patent: WO2006/123725,2006,A1 .Location in patent: Page/Page column 47-48
[7]Organic Letters,2019,vol. 21,p. 3299 - 3303

26
[ 942995-99-5 ]
[ 7325-46-4 ]
C₄₀H₅₆Cl₂N₁₆O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With O-(7-azabenzotriazole-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 1h;	Asolution of <strong>[7325-46-4]1,4-phenylenediacetic acid</strong> (24 mg, 0.125 mmol) in DMF (0.75 mL) and Et3N (0.2 mL) is treated with HATU (95 mg, 0.25 mmol) and stirred at RT for 30 minutes. To this mixture is added Intermediate B (0.1 g, 0.25 mmol) and stirring continued for a further 30 minutes. The reaction mixture is passed through a 1 g AL-B Solid Phase Extraction cartridge, eluting with DMF (1.5 mL). The solvent is removed in vacuo and recrystallisation of the crude residue from MeOH affords the product. [M+H]+ 959.74.

Reference： [1]Patent: WO2007/71396,2007,A2 .Location in patent: Page/Page column 32

27
[ 343876-97-1 ]
[ 7325-46-4 ]
[ 3945-69-5 ]
[ 477219-59-3 ]

Yield	Reaction Conditions	Operation in experiment
	In N-methyl-acetamide; toluene;	EXAMPLE 21 Preparation of N,N'-bis(4-dimethylamino-2-methylquinolin-6-yl)-1,4-phenylenediacetamide 4-(4,6-Dimethoxy-1,3,5-triazine-2-yl)-4-methylmorpholinium chloride (91.3 mg, 0.33 mmol) and then 66.4 mg (0.33 mmol) of 4-dimethylamino-6-amino-quinaldine are successively added to a solution of 29.1 mg (0.15 mmol) of 1,4-phenylenediacetic acid in 2 mL of dimethylformamide, at a temperature in the region of 20 C. The mixture obtained is stirred at a temperature in the region of 20 C. for about 18 hours. The reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) at 40 C. The residue obtained is taken up in 5 mL of toluene and then concentrated to dryness under reduced pressure (2.7 kPa) at 40 C. The yellowish solid thus obtained is purified by FLASH chromatography on a BOND-ELUT cartridge (27 mm in diameter) filled with 25 g of conditioned silica (15-35 mum) and then eluted with a (dichloromethane/2M ammoniacal methanol) (90-10 by volume) mixture at a flow rate of 10 mL per minute. The fractions between 180 and 250 mL are combined and concentrated to dryness under reduced pressure (2.7 kPa) to 40 C. 40 mg of N,N'-bis-(4-dimethylamino-2-methylquinolin-6-yl)-1,4-phenylenediacetamide are thus obtained in the form of a foam whose characteristics are the following: 1H NMR spectrum (300 MHz, (CD3)2SO d6, delta in ppm): 2.51 (s: 6H); 2.93 (s: 12H); 3.69 (s: 4H); 6.76 (s: 2H); 7.04 (s: 4H); 7.71 (dd, J=9 and 2.5 Hz: 2H); 7.77 (d, J=9 Hz: 2H); 8.49 (d, J=2.5 Hz: 2H); 10.40 (broad s: 2H).

Reference： [1]Patent: US2004/138257,2004,A1

28
[ 1080018-71-8 ]
[ 7325-46-4 ]
[ 1080018-65-0 ]

Yield	Reaction Conditions	Operation in experiment
		Benzyl (1 ,1'-(1 ,4-phenylenebis(methylene))bis(azanediyl)bis (oxomethylene) bis(piperidine-4,1-diyl))bis(azanediyl)bis((3,5-diamino-6-chloro pyrazine-2- carboxamido)methan-1-yl-1-ylidene)dicarbamateTo a suspension of (4-carboxymethyl-phenyl)-acetic acid (0.5 g, 2.57 mmol) in dry DCM (10 ml.) under an inert atmosphere of nitrogen is added TEA (0.7 ml_, 5.14 mmol) followed by diphenylphosphoryl azide (1.1 ml_, 5.14 mmol). After stirring at reflux for 2 hours, the mixture is treated with a solution of benzyl (3,5-diamino-6-chloropyrazine-2- carboxamido)(piperidin-4-ylamino)methylenecarbamate (Intermediate C) (1.72 g, 3.9 mmol) and TEA (0.7 ml_, 5.14 mmol) in DCM/DMF (10 ml_). The resulting mixture is heated at 38 C overnight and then allowed to cool to room temperature. The solvent is removed in vacuo and purification of the crude product by chromatography on silica eluting with 9:1 DCIWMeOH affords the title compound.

Reference： [1]Patent: WO2008/135557,2008,A1 .Location in patent: Page/Page column 31-32

29
[ 139024-81-0 ]
[ 7325-46-4 ]
C₃₈H₆₄N₆O₁₀ [ No CAS ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2009,vol. 64,p. 153 - 158

30
[ 259680-82-5 ]
[ 7325-46-4 ]
[ 1158804-24-0 ]

Yield	Reaction Conditions	Operation in experiment
	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In tetrahydrofuran; at 20℃;	(i) {4-[2-({3-[2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]propyl}amino)-2- oxoethyl]phenyl}acetic acidA solution of T3P (1.591ml, 1.57M in THF) was added to a mixture of the product from example 1 step (v) (0.2g), TEA (0.333ml) and 2,2'-(l,4-phenylene)diacetic acid (0.463g) in THF (15mL) and the mixture stirred at rt overnight. The reaction was diluted with EtOAc, washed with water, dried and evaporated under reduced pressure. Used crude in next step. LC-MS m/z 428 APCI+

Reference： [1]Patent: WO2009/67081,2009,A1 .Location in patent: Page/Page column 93

31
[ 7325-46-4 ]
[ 434-13-9 ]
[ 1292814-43-7 ]

Yield	Reaction Conditions	Operation in experiment
25%	With dmap; dicyclohexyl-carbodiimide; In pyridine; dichloromethane; at 120℃; for 2h;Microwave irradiation;	General procedure: LA (0.3 - 0.5 mmol) and DMAP (0.3 - 0.5 mmol) were dissolved in 2 - 4 ml of pyridine. The corresponding carboxylic acid (2.1 - 4.0 mmol) and DCC (1.2 - 1.5 mmol) were dissolved in 0.5 - 1.5 ml dichloromethane. The two reaction solutions were mixed and heated at 120 C for 2 hrs. After cooling, the reaction mixture was filtered and concentrated. The product was purified by ISCO reverse-phase column chromatography. The final product was further purified by HPLC.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1926 - 1928

32
[ 7325-46-4 ]
[ 17833-56-6 ]

Reference： [1]Green Chemistry,2011,vol. 13,p. 2888 - 2894
[2]Patent: WO2006/123725,2006,A1
[3]Chemical Science,2018,vol. 9,p. 8930 - 8936
[4]Patent: EP3581561,2019,A1

33
[ 64479-78-3 ]
cadmium(II) nitrate tetrhydrate [ No CAS ]
[ 7325-46-4 ]
[ 7732-18-5 ]
[Cd₃(1,4-phenylenediacetate)2(isonicotinate)2(H₂O)2] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%	In water High Pressure; Cd compd., 4-pina, and 1,4-phdaH2 (2.7:2.9:4.5 molar ratio) in H2O, sealed, heated at 120°C for 48 h; cooled to room temp., septd., washed (H2O, acetone), dried in air, elem.anal.;

Reference： [1]Uebler, Jacob W.; Laduca, Robert L. [Inorganic Chemistry Communications, 2012, vol. 19, p. 31 - 35]

34
[ 7325-46-4 ]
[ 1449412-39-8 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
44%	With N-Bromosuccinimide; sulfuric acid In water at 25℃; for 16h;

Reference： [1]Sarkar, Parantap; Durola, Fabien; Bock, Harald [Chemical Communications, 2013, vol. 49, # 68, p. 7552 - 7554]

35
[ 201230-82-2 ]
[ 623-25-6 ]
[ 7325-46-4 ]

Yield	Reaction Conditions	Operation in experiment
90%		General procedure: 1 mmol of the selenium-containing catalyst prepared in Example 1 and 20 mL of n-butanol were placed in the flask, and air was discharged through carbon monoxide. The pressure was 0.1 MPa at a carbon monoxide, and the mixture was heated under reflux for 2 hours to activate the catalyst. After completion of the reaction, 20 mmol of benzyl chloride, 25 mL of 15% sodium hydroxide solution, 0.05 mmol of tetrabutylammonium bromide, and carbon monoxide were discharged to the air, and the reaction was carried out for one day under the conditions of a carbon monoxide pressure of 0.1 MPa and a temperature of 50 C. After completion of the reaction, the aqueous phase in the reaction mixture was separated using a sep. funnel, and the organic phase was washed with water (15 mL×3). The aqueous phase and the washing liquid were combined, and concentrated to 15 mL by heating. After cooling, hydrochloric acid was added to adjust the pH of the solution to 2. The resulting solution was frozen at a temperature below 5 C for 12 hours, suction filtered, and dried to give phenylacetic acid in a yield of 92%. With the embodiment 2 similar, the difference lies in that: the raw material benzyl chloride was changed to benzyl dichloride, phenylenediacetic acid to be 2.55 g, yield 90%.
80%		General procedure: A 100 mL reactor equipped with Teflon-coated magnetic stir bars was charged with n-Butyl alcohol (20 mL) and the catalyst (0.5 mmol). The reactor was then taken out of the glove box and pressured with carbon monoxide (1 atm). The mixture was stirred 2 h at 60 C, cooled to ambient temperature and slowly vented. After benzyl chloride (10 mmol), NaOH (15 mL, 15%), and TBAI (0.25 mmol) were added, the reactor was sealed and the reaction mixtures were stirred for 22 h at 60 C under carbon monoxide (1 atm). After the reaction, the water phase was detached and washing the organic phase three times with H2O (3×5 mL), the combined water layer was washed with Et2O, then the resulting solution was cooled to 0 C and adjusted to pH=1-2 with HCl (6 mol/L). The product was filtered, dried in RT, and then recrystallized.

Reference： [1]Patent: CN108250155,2018,A .Location in patent: Paragraph 0019; 0020; 0025; 0026
[2]Tetrahedron,2013,vol. 69,p. 7264 - 7268

36
[ 1915-42-0 ]
copper (II) nitrate tetrahydrate [ No CAS ]
[ 7325-46-4 ]
[Cu(1,4-phenylenediacetate)(4,4′-dipyridylamine)]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium hydroxide; In water; at 120℃; for 24h;Autoclave; High pressure;	Cu(NO3)2·4H2O (86 mg, 0.37 mmol), <strong>[7325-46-4]1,4-phenylenediacetic acid</strong> (71 mg, 0.37 mmol), and dpa (63 mg, 0.37 mmol) were placed in 10 mL of distilled H2O in a 23 mL Teflon-lined Parr acid digestion bomb. An aliquot of NaOH solution (1.0 M, 0.5 mL, 0.5 mmol) was added to basicify the solution. The bomb was sealed and heated at 120C for 24 h, and then cooled to ambient temperature. Purple blocks of 4 (102 mg, 65% yield based on Cu) were isolated after washing with distilled water and acetone and drying in air. Anal. Calc. for C20H17CuN3O4 4: C, 56.27; H, 4.01; N, 9.84. Found: C, 56.01 H, 3.74; N, 9.63%. IR (cm-1): 3049 (w, br), 1737 (w), 1585 (s), 1523 (m), 1488 (w), 1444 (m), 1424 (w), 1357 (s), 1210 (m), 1165 (w), 1106 (w), 1070 (w), 1056 (w), 1020 (m), 910 (w), 851 (m), 822 (m), 812 (m), 767 (m), 727 (w), 702 (w), 669 (m), 661 (m).

Reference： [1]Inorganica Chimica Acta,2013,vol. 407,p. 297 - 305

37
cadmium(II) nitrate tetrhydrate [ No CAS ]
[ 7325-46-4 ]
[ 1338812-80-8 ]
[ 7732-18-5 ]
[Cd(p-phda)(1,4-bis(1,2,4-triazol-1-ylmethyl)-2,3,5,6-tetramethylbenzene)(H₂O)]H₂O}_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	at 160℃; for 72h;High pressure;	A mixture of Cd(NO3)2*4H2O (30.8 mg, 0.1 mmol), btmx (29.8 mg, 0.1 mmol), and p-H2phda (19.4 mg, 0.1 mmol) in 10 mL distilled H2O was sealed in a 25 mL Teflon-lined stainless steel container and heated at 160 C for 3 days. After the mixture was cooled to room temperature at a rate of 5 C/h, colorless crystals of 3 were obtained, yield 63% based on Cd.

Reference： [1]Inorganica Chimica Acta,2013,vol. 405,p. 318 - 325

38
[ 934522-26-6 ]
[ 7325-46-4 ]
[ 5970-45-6 ]
[Zn(1-(4-pyridylmethyl)benzimidazole)(phenylenediacetic acid)]*2H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With ammonium hydroxide; In methanol; ethanol; water; at 20℃;Sonication;	A mixture of Zn(AC)2·2H2O (21.9 mg, 0.1 mmol), pmbm (24.6 mg, 0.1 mmol) and H2tpa (16.6 mg, 0.1 mmol) was stirred in ethanol-water-methanol mixed solvent (7 mL, v/v/v: 3/2/2). The pmbm ligands were bought from the company of Jinan Henghua. Then aqueous NH3 solution (25%, 10 d) was dropped into the mixture to give a clear solution under ultrasonic treatment. The resultant solution was allowed to evaporate slowly in darkness at room temperature for several days to give pale-yellow crystals of 1

Reference： [1]Journal of Molecular Structure,2013,vol. 1048,p. 124 - 129

39
manganese(II) nitrate hexahydrate [ No CAS ]
[ 7325-46-4 ]
[ 7732-18-5 ]
[ 39642-69-8 ]
[Mn(1,4-phenylenedicarboxylate)(3-pyridylisonicotinamide)(H₂O)]*3H₂O}_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8%	With sodium hydroxide; at 100℃; for 24h;High pressure;	Mn(NO3)2.6H2O (66 mg, 0.37 mmol), 3-pina (74 mg, 0.37 mmol),1,4-phenylenedicarboxylic acid (72 mg, 0.37 mmol) and 0.5 mL of1.0 M NaOH solution were mixed with 10 mL of distilled H2O in a23 mL Teflon-lined acid digestion bomb. The bomb was sealed and heated in an oven at 100 C for 24 h, and then was cooled slowly to 25 C. Brownish blocks of 3 (16 mg, 8% yield based on 3-pina) were isolated after washing with distilled water, ethanol, and acetone and drying in air. Anal. Calc. for C21H25MnN3O9 3: C, 48.66; H,4.86; N, 8.11. Found: C, 48.19; H, 4.43; N, 7.98%. IR (cm1):3538(w), 3278 (w), 3042(w), 1670 (m), 1605(w), 1545 (s), 1483(s), 1446 (m), 1405 (s), 1332 (m), 1302 (m), 1238 (w), 1193 (w),1146 (w), 1104 (w), 1064 (w), 1054 (w), 1026 (w), 1009 (w), 953(w), 932 (w), 898 (w), 861 (w), 863 (w), 801 (m), 772 (s), 756 (s),741 (s), 706 (s), 696 (s), 672 (s).

Reference： [1]Inorganica Chimica Acta,2014,vol. 419,p. 26 - 35

40
cadmium(II) nitrate hexahydrate [ No CAS ]
[ 7325-46-4 ]
[ 90824-49-0 ]
Cd⁽²⁺⁾*4H₂O*C₁₀H₈O₄^(2-)*C₈H₁₂N₆O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23.7%	With potassium hydroxide; In water; at 150℃; for 72h;Autoclave;	A mixture of Cd(NO3)2 6H2O (0.0345 g, 0.100 mmol), H2PBEA (0.0195 g, 0.100 mmol), BTE (0.0416 g, 0.200 mmol), and KOH (0.0112 g, 0.200 mmol) in H2O (10 mL) was sealed in a 16 ml Teflon-lined stainless steel container and heated at 150C for 72 h. After cooling to room temperature, white block crystals of complex 1 were collected by filtration and washed by water and ethanol several times. (yield 23.7%, based on H2PBEA). Elemental analysis for C18H28CdN6O9, % (Mr = 584.86): C 36.96, H 4.83, N 14.37; found, %: C 37.04, H 4.85,N 14.41. Selected IR peaks (cm-1): 3437 (m), 1623 (s), 1463 (s), 1245 (s), 831(w), 776 (w), 701 (w).

Reference： [1]Journal of Structural Chemistry,2014,vol. 55,p. 1395 - 1400
Zh. Strukt. Kim.,2014,vol. 55,p. 223 - 228,6

41
cadmium(II) nitrate tetrhydrate [ No CAS ]
[ 7325-46-4 ]
[ 52550-63-7 ]
[Cd₂(1,4-bis(2-methylimidazol-1-yl)butane)(1,4-benzenediacetate)₂]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In water; at 110℃; for 48h;pH 6;Autoclave;	General procedure: A solution of H2bdc (0.2mmol) or H2bda (0.2mmol) in 12mL H2O was adjusted to pH6 with dilute NaOH solution. Then bib (0.2mmol) and Cd(NO3)2·4H2O (0.2mmol) were added with stirring. The mixture was added to a 25mL Teflon-lined stainless autoclave and this was sealed and heated to 110C for 2days and then cooled to room temperature to give the colorless crystals 1 and 2.

Reference： [1]Inorganic Chemistry Communications,2015,vol. 57,p. 84 - 88

42
zinc(II) nitrate hexahydrate [ No CAS ]
[ 7325-46-4 ]
3,6-di(1H-imidazol-1-yl)-9H-carbazole [ No CAS ]
Zn⁽²⁺⁾*C₁₈H₁₃N₅*C₁₀H₈O₄^(2-)*1.5H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	In water; acetonitrile; at 160℃; for 24h;Sealed tube;	General procedure: To a 10mL Pyrex glass tube was added Zn(NO3)*6H2O (30mg,0.1mmol), 1,4-H2bdc (17mg,0.1mmol), 3,6-bmcz (30mg,0.1mmol), 2mL of H2O and 1mL of MeCN. the tube was sealed and heated in an oven to 160 C for 1d and then cooled to ambient temperature at the rate of 5C h-1 to form brown blocks of 1, which were washed with water-methanol and dried in air.

Reference： [1]Journal of Solid State Chemistry,2015,vol. 232,p. 200 - 206

43
[ 7325-46-4 ]
[ 6147-53-1 ]
[ 39642-63-2 ]
[Co(N,N'-di(3-pyridyl)adipoamide)(1,4-pda)]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%	In water; at 120℃; for 48h;Autoclave; High pressure;	General procedure: A mixture of Co(CH3COO)2·4H2O (0.044g, 0.20mmol), L (0.028g. 0.10mmol), 1,2-H2pda (0.037g, 0.20mmol) and 3mL of H2O was sealed in a 23mL Teflon-lined stainless steel autoclave, which was then heated under autogenous pressure at 120C for 2days. Slow cooling of the reaction system afforded pink crystals suitable for single-crystal X-ray diffraction.

Reference： [1]Polyhedron,2016,vol. 106,p. 32 - 39

44
[ 66-71-7 ]
indium(III) nitrate pentahydrate [ No CAS ]
[ 7325-46-4 ]
1.5C₁₀H₈O₄^(2-)*C₁₂H₈N₂*In⁽³⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%		[In(pda)1.5(phen)]n 1: Complex 1 was isolated by mixing In(NO3)3.5H2O (0.2 mmol), phen (0.2 mmol), H2pda (0.2 mmol),and NaOH (0.3 mmol) in 10 ml water and stirred for 30 min in air.Then the mixture was transferred to 25 ml stainless-steel reactors with Teflon liner and heated to 150 C in 3 h. The temperature waskept at 150 C for 4 days and cooled to room temperature during 24 h. Colorless block crystals of 1 was isolated by filtration, washed with distilled water, and dried in air (yield based on In: 32%). Anal.Calcd. for C27H20InN2O6 (583.27): C 55.60, H 3.46, N 4.80; found: C55.52, H 3.21, N 4.77. IR (KBr, cm1): 3220 (m, br), 3063 (w), 1614(vs), 1560 (s), 1432 (s), 1382 (s), 1187 (m), 1112 (w), 1047 (m), 852(m), 756 (m), 690 (m).

Reference： [1]Journal of Molecular Structure,2016,vol. 1118,p. 105 - 109

45
cadmium(II) nitrate tetrhydrate [ No CAS ]
[ 7325-46-4 ]
[ 52550-63-7 ]
Cd⁽²⁺⁾*C₁₀H₈O₄^(2-)*0.5C₁₂H₁₈N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With sodium hydroxide; In water; at 160℃; for 72h;High pressure; Autoclave;	The mixtures of Cd(NO3)2 ¢4H2O (0.5 mmol, 0.145 g), H2pda(0.5 mmol,0.097 g), bib (0.5 mmol, 0.109 g), NaOH(1 mmol, 0.04 g), and 15 mL of water were placed in a25 mL Teflon reactor which was heated to 160 C for threedays and then cooled to room temperature. The yellow crystals were obtained and picked out, washed with distilledwater and dried in air (Yield: 42% based on Cd). ElementalAnal. Calcd. (%) for C16H17CdN2O4: C: 46.45; H, 4.14; N,6.77. Found: C: 46.47; H, 4.15; N, 6.78. IR/cm 1(KBr):1622 s, 1520 s, 1487s, 1317 m, 1267 m, 1150 m, 1097 m,961 m, 830 m, 757 m.

Reference： [1]Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry,2016,vol. 46,p. 1298 - 1301

46
cobalt(II) chloride hexahydrate [ No CAS ]
[ 58954-23-7 ]
[ 7325-46-4 ]
3Co⁽²⁺⁾*6C₈H₇N₂O₄^(3-)*C₁₀H₁₀O₄*6H₂O*12H⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	In ethanol; water; at 130℃; for 78h;pH 6;Autoclave;	Synthesis of Complex (2)H3Pimdc (0.1980 g, 1 mmol), H2PDA (0.1920 g, 1 mmol), andCoCl2.6H2O (0.1188 g, 0.5 mmol) were added to a mixed water(15 mL) and ethanol (10 mL) solution, then the PH of the solution was adjusted to 6, then the mixed solution was put into thein Teflon-lined stainless reactor, then reacted for 78 h at 130Cand cooled to room temperature naturally, with the red crystals fit for X-ray diffraction picked out by washing with distilledwater and dried in air (the yield was 65% based on Co).For C58H76N12O42Co3: Anal. Calcd. (%): C, 38.91; H, 4.25;N, 9.39; O, 37.54; Found (%): C, 38.90; H, 4.28; N, 9.37; O,37.53. IR data (KBr; v, cm1): 3494 m, 3130 m, 1713 m,1651 vs, 1579 vs, 1545 vs,1540 vs, 1485 vs, 1398 s, 1272 m,1110 m, 1054 s, 963 m, 864 m, 780 m, 678 m, 508 w, 493 w.

Reference： [1]Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry,2016,vol. 46,p. 1834 - 1841

47
nickel(II) perchlorate hexahydrate [ No CAS ]
[ 7325-46-4 ]
[ 7732-18-5 ]
[ 39642-93-8 ]
C₁₈H₂₂N₄O₂*Ni⁽²⁺⁾*4H₂O*C₁₀H₈O₄^(2-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With sodium hydroxide; at 120℃; for 48h;Autoclave;	General procedure: ZnBr2 (0.045g, 0.2mmol), H2oba (0.052g, 0.20mmol and L1 (0.060g, 0.20mmol) were placed in a Teflon-lined digestion bomb (internal volume of 23mL) containing 10ml 0.04M NaOH under autogenous pressure. The reaction mixture was then heated at 120C for 2days, followed by slow cooling at a rate of 6Ch-1 to room T. The colorless crystals were then collected, washed with H2O and then dried under vacuum. Yield: 0.061g (46%).

Reference： [1]Polyhedron,2016,vol. 117,p. 777 - 787

48
[ 7325-46-4 ]
[ 7732-18-5 ]
[ 6147-53-1 ]
[ 39642-93-8 ]
C₁₈H₂₂N₄O₂*4H₂O*C₁₀H₈O₄^(2-)*Co⁽²⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With sodium hydroxide; at 120℃; for 48h;Autoclave;	General procedure: ZnBr2 (0.045g, 0.2mmol), H2oba (0.052g, 0.20mmol and L1 (0.060g, 0.20mmol) were placed in a Teflon-lined digestion bomb (internal volume of 23mL) containing 10ml 0.04M NaOH under autogenous pressure. The reaction mixture was then heated at 120C for 2days, followed by slow cooling at a rate of 6Ch-1 to room T. The colorless crystals were then collected, washed with H2O and then dried under vacuum. Yield: 0.061g (46%).

Reference： [1]Polyhedron,2016,vol. 117,p. 777 - 787

49
[ 7325-46-4 ]
[ 7732-18-5 ]
[ 5743-04-4 ]
[ 39642-93-8 ]
C₁₈H₂₂N₄O₂*2H₂O*C₁₀H₈O₄^(2-)*Cd⁽²⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With sodium hydroxide; at 120℃; for 48h;Autoclave;	General procedure: ZnBr2 (0.045g, 0.2mmol), H2oba (0.052g, 0.20mmol and L1 (0.060g, 0.20mmol) were placed in a Teflon-lined digestion bomb (internal volume of 23mL) containing 10ml 0.04M NaOH under autogenous pressure. The reaction mixture was then heated at 120C for 2days, followed by slow cooling at a rate of 6Ch-1 to room T. The colorless crystals were then collected, washed with H2O and then dried under vacuum. Yield: 0.061g (46%).

Reference： [1]Polyhedron,2016,vol. 117,p. 777 - 787

50
[ 7325-46-4 ]
[ 6080-56-4 ]
2C₁₀H₈O₄^(2-)*2Pb⁽²⁺⁾*3H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In water; at 120℃; for 72h;pH 7;Autoclave; High pressure;	General procedure: A mixture of Pb(OAc)2·3H2O (19.0 mg, 0.05 mmol) and 1,2-H2pda (9.7 mg, 0.05 mmol) in 15 mL water was adjusted to pH=7 with 0.5 M KOH solution and then sealed in 25 mL Teflon-lined stainless steel autoclaves. The resulting solution was heated to 160 C for 72 h and then cooled to room temperature at a rate of 0.2 C min-1 and gave some block colorless crystals. Yield: 51%.

Reference： [1]Journal of Solid State Chemistry,2015,vol. 223,p. 131 - 137

51
[ 7325-46-4 ]
[ 6080-56-4 ]
2C₁₀H₈O₄^(2-)*2Pb⁽²⁺⁾*3H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In water; at 160℃; for 72h;pH 7;Autoclave; High pressure;	General procedure: A mixture of Pb(OAc)2·3H2O (19.0 mg, 0.05 mmol) and 1,2-H2pda (9.7 mg, 0.05 mmol) in 15 mL water was adjusted to pH=7 with 0.5 M KOH solution and then sealed in 25 mL Teflon-lined stainless steel autoclaves. The resulting solution was heated to 160 C for 72 h and then cooled to room temperature at a rate of 0.2 C min-1 and gave some block colorless crystals. Yield: 51%.

Reference： [1]Journal of Solid State Chemistry,2015,vol. 223,p. 131 - 137

52
[ 7325-46-4 ]
C₁₇H₂₀N₂O₂*ClH [ No CAS ]
C₄₄H₄₆N₄O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21 mg	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 2h;	Example 47 To a solution of an HC1 salt of Intermediate 4 (40 mg, 0.13 mmol), 2,2'-(l,4- phenylene)diacetic acid (11.5 mg, 0.059 mmol) and DIPEA (0.083 mL, 0.475 mmol) in DMF (0.9 mL) was added HATU (49.7 mg, 0.131 mmol). The reaction mixture was stirred at rt for 2 h and then purified by preparative HPLC to afford the title compound as a white solid (21 mg). LC-MS retention time = 1.27 min; m/z = 727.2 [M+H]+. (Column: Waters Aquity BEH C18 2.1 X 50 mm 1.7^m-particles; Solvent A = 100% Water/ 0.05% TFA; Solvent B = 100% Acetonitrile/0.05% TFA; Flow Rate = 0.8 mL/min. Start % B = 2; Final % B = 98; Gradient Time = 1.5 minutes; Wavelength = 220 nm).

Reference： [1]Patent: WO2016/172425,2016,A1 .Location in patent: Page/Page column 208

53
[ 7325-46-4 ]
[ 288-88-0 ]
1,4-benzene diacetyltriazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%		32.8 g (0.18 mol) of 1,4-benzene-2-acetic acid was suspended in 120 mL of 2-chlorotoluene and 24 mL of DMF (about 0.36 mol) was added. 73 g (0.36 mol) of phthaloyl chloride was added dropwise thereto, followed by stirring at 70 C. to obtain a homogeneous solution in 45 minutes. The solution was cooled to 55 C., and a solution prepared by dissolving 51.6 g (0.75 mol) of 1,2,4-triazole in 180 mL of DMF was added dropwise over 20 minutes. The crystals precipitated by natural cooling to 30 C were collected by filtration, washed twice with 250 mL of water and dried under reduced pressure for 2 hours at 80 C. 35 g of pale yellow crystals of 1,4-benzene diacetyltriazole (66% ).

Reference： [1]Patent: JP6088890,2017,B2 .Location in patent: Paragraph 0059

54
[ 7325-46-4 ]
[ 5970-45-6 ]
[ 42032-51-9 ]
[Zn(μ-1,4-phenylenediacetate)(μ-1,2-bis(imidazol-1-ylmethyl)benzene)]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With potassium hydroxide; In water; at 160℃; for 72h;High pressure; Autoclave;	2.2.1 Synthesis of [Zn(pda)(bib)]n (1) A mixture of H2pda (9.6 mg, 0.05 mmol), bib (11.7 mg, 0.05 mmol), Zn(OAc)2·2H2O (22.0 mg, 0.1 mmol), and KOH (5.6 mg, 0.1 mmol) were added to water (12 mL) in a 25 mL Teflon-lined stainless steel vessel. The mixture was heated at 160 C for 3 days. After the reactive mixture was slowly cooled to room temperature, colorless block crystals of 1 were obtained (yield: 55%, based on Zn). Anal. Calc. (%) for C24H22N4O4Zn: C 58.13, H 4.47, N 11.30; found (%): C 57.66, H 4.32, N 11.24. IR (cm-1): 3479 (m), 3110 (m), 3011 (w), 2966 (w), 2369 (w), 1592 (s), 1522 (s), 1462 (m), 1371 (s), 12775 (m), 1251 (m), 1107 (m), 1018 (w), 949 (m), 858 (m), 747 (m), 723 (s), 659 (m), 625 (m), 539 (w).
	In water; at 170℃; for 72h;Autoclave;	A mixture of H2ppda (0.8 mmol, 0.15 g), Zn(O2CMe)2?2H2O (0.7 mmol, 0.16 g), obix (0.8 mmol, 0.18 g) and H2O (30 mL) was placed in a 45 mL Parr brand teflon-lined acid digestion bomb and sealed then heated at 170 C for 3 days, and then cooled at a rate of 5 C h-1 to room temperature. Colorless crystals of 6 were collected by filtration and washed with water. Anal. calcd. for C24H22N4O4Zn: C 58.08, H 4.43, N 11.29. Found: C 58.14, H 4.38, N 11.20. IR (KBr, cm-1): 3107w, 2902w, 1619m, 1590vs, 1375vs, 1249w, 1110m, 944w, 862m, 717s.

Reference： [1]Journal of Molecular Structure,2017,vol. 1137,p. 606 - 609
[2]Journal of Solid State Chemistry,2017,vol. 252,p. 8 - 21

55
[ 7325-46-4 ]
[ 42032-51-9 ]
[ 10108-64-2 ]
Cd(pda)<SUB>0.5</SUB>(1,2-bis(imidazol-1-ylmethyl)benzene)Cl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In water; at 160℃; for 72h;High pressure; Autoclave;	General procedure: 2.2.1 Synthesis of [Zn(pda)(bib)]n (1) A mixture of H2pda (9.6 mg, 0.05 mmol), bib (11.7 mg, 0.05 mmol), Zn(OAc)2·2H2O (22.0 mg, 0.1 mmol), and KOH (5.6 mg, 0.1 mmol) were added to water (12 mL) in a 25 mL Teflon-lined stainless steel vessel. The mixture was heated at 160 C for 3 days. After the reactive mixture was slowly cooled to room temperature, colorless block crystals of 1 were obtained.

Reference： [1]Journal of Molecular Structure,2017,vol. 1137,p. 606 - 609

56
[ 4916-57-8 ]
zinc(II) nitrate hexahydrate [ No CAS ]
[ 7325-46-4 ]
2Zn⁽²⁺⁾*2C₁₀H₈O₄^(2-)*2C₁₂H₁₂N₂*5H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of H2ppda (1 mmol, 0.2 g), Zn(NO3)26H2O (0.5 mmol,0.15 g), NaOH (0.5 mmol, 0.02 g), bpa (0.5 mmol, 0.09 g) and H2O(10 mL) was stirred at 70 C for half an hour and thenwas heated ina microwave oven for 30 min with the power set at 600 W. Afterirradiation, the flask was allowed to cool to room temperature.Colorless crystals of 1 were collected by filtration and washedseveral times with water. The complex is all air stable at roomtemperature. Analytically calculated for C44H50N4O13Zn2: C 54.28, H5.18, N 5.75. Found: C 54.42, H 5.34, N 5.80. IR (KBr, cm1): 3366 w,3270 w, 3050 w, 2931 w, 1619 s, 1580 vs, 1434 s, 1366 vs, 1229 m,1144 w, 1071 w, 1033 w, 935 w, 837 m, 724 s, 638 m, 547 m.

Reference： [1]Journal of Molecular Structure,2017,vol. 1143,p. 355 - 361

57
[ 7325-46-4 ]
[ 5970-45-6 ]
[ 69506-92-9 ]
[Zn(μ-1,4-phenylenediacetate)(μ-1,3-bis(imidazol-1-ylmethyl)benzene)]*0.5H₂O}_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water at 170℃; for 120h; Autoclave;	7 2.7 Synthesis of [Zn(μ-ppda)(μ-mbix)]·0.5H₂O}_n (7) A mixture of H2ppda (0.7 mmol, 0.15 g), Zn(O2CMe)2·2H2O (0.7 mmol, 0.17 g), mbix (0.8 mmol, 0.21 g) and H2O (30 mL) was placed in a 45 mL Parr brand teflon-lined acid digestion bomb and sealed then heated at 170 °C for 5 days, and then cooled at a rate of 5 °C h-1 to room temperature. Colorless crystals of 7 were collected by filtration and washed with water. Anal. calcd. for C48H46N8O9Zn2: C 52.10, H 4.59, N 11.10. Found: C 52.04, H 4.74, N 8.00. IR (KBr, cm-1): 3471w, 3134w, 1608m, 1530vs, 1443m, 1361vs, 1273m, 1211w, 1107w, 953w, 860m, 705s, 652m, 574m.

Reference： [1]Günay Sezer, Güneş; Zafer Yeşilel, Okan; Şahin, Onur; Burrows, Andrew D. [Journal of Solid State Chemistry, 2017, vol. 252, p. 8 - 21]

58
[ 7325-46-4 ]
[ 5743-04-4 ]
[ 69506-92-9 ]
[Cd(μ₃-1,4-phenylenediacetate)(μ-1,3-bis(imidazol-1-ylmethyl)benzene)]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; N,N-dimethyl-formamide at 120℃; for 168h; Autoclave;	2.11. Synthesis of [Cd(μ3-ppda)(μ-obix)]n (12) General procedure: A mixture of H2ppda (1 mmol, 0.20 g), Cd(O2CMe)22H2O(1 mmol, 0.27 g), obix (1.2 mmol, 0.28 g) and DMF/H2O (32 mL, vv=1:3) was placed in a 45 mL Parr brand teflon-lined acid digestionbomb and sealed then heated at 120 °C for 7 days, and then cooled at arate of 5 °C h-1 to room temperature. Colorless crystals of 12 werecollected by filtration and washed with water.

Reference： [1]Günay Sezer, Güneş; Zafer Yeşilel, Okan; Şahin, Onur; Burrows, Andrew D. [Journal of Solid State Chemistry, 2017, vol. 252, p. 8 - 21]

59
[ 2632-99-7 ]
[ 7325-46-4 ]
[ 5970-45-6 ]
[Zn(μ₄-1,4-phenylenediacetate)(μ-4,4′-azobis(pyridine))_0.5]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	In water; at 70 - 120℃; for 72.5h;	The mixture of H2ppda (0.1 mmol, 0.018 g), Zn(O2CMe)22H2O(0.1 mmol, 0.02 g), abpy (0.2 mmol, 0.018 g) and H2O (10 mL) wasstirred at 70 C for 30 min. Then clear solution was placed in a Pyrextube and heated at 120 C for 72 h. After cooling to room temperature,red crystals of 1 were obtained in 93% yield based on H2ppda(0.018 g). Anal. calcd. for C15H12N2O4Zn: C 51.53, H 3.46, N 8.01.Found: C 51.52, H 3.61, N 8.21. IR (KBr, cm-1): 3045 w, 2939 w, 1620s, 1525 s, 1380 vs, 1299 m, 1230 m, 1059 w, 1019 w, 951 w, 860 m,757 m.

Reference： [1]Journal of Solid State Chemistry,2017,vol. 255,p. 89 - 96

60
[ 36076-26-3 ]
[ 113520-36-8 ]
[ 7325-46-4 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hydroxide monohydrate; water; In tetrahydrofuran; ethanol;	[00183] To a stirred solution of diethyl 2,2'-(l,4-phenylene)diacetate (950 mg, 3.8 mmol) in 3: 1: 1 EtOH/THF/H20 (50 mL) was added LiOH.H20 (200 mg, 4.7 mmol). The mixture was stirred overnight and concentrated. The aq residue was diluted with water (10 mL), washed with ether (60 mL) and acidified with cone HCl. The acidic solution was extracted with ether (2 x 50 mL). These ether extracts were combined, washed with brine (10 mL), dried over Na2S04 and concentrated to leave a white solid. 1H NMR indicated a ~2: 1 mixture of the desired monoester (AC8, R = Et) and diacid (AC9, R = H) which was used without further purification.

Reference： [1]Patent: WO2017/132432,2017,A1 .Location in patent: Paragraph 00183

61
cadmium(II) nitrate tetrhydrate [ No CAS ]
[ 7325-46-4 ]
[ 1569668-28-5 ]
[Cd(PDA)(1-(imidazo-1-yl)-4-(1,2,4-triazol-1-ylmethyl)benzene)]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With sodium hydroxide; In water; at 160℃; for 72h;Autoclave; Sealed tube;	General procedure: [Cd(IPA)(TMB)].0.5(H2O)} (1): The mixture of Cd(NO3)2.4H2O (0.145 g, 0.5 mmol), H2IPA (0.106 g, 0.5 mmol),TMB (0.113 g, 0.5 mmol), NaOH (0.04 g, 1 mmol), and deionized water (15 mL) was sealed in a 25-mL Teflon-lined stainless steel vessel and heated at 160C for 72 h. After cooling to room temperature, yellow crystals were obtained (yield: 44% based on Cd).

Reference： [1]Inorganic and Nano-Metal Chemistry,2017,vol. 47,p. 531 - 535

62
[ 82410-79-5 ]
copper(II) nitrate trihydrate [ No CAS ]
[ 7325-46-4 ]
[ 7732-18-5 ]
[Cu₂(1,4-bis(2-methyl-imidazol-1-ylmethyl)benzene)(1,4-benzenediacatate)₂]*H₂O}_n [ No CAS ]

Reference： [1]RSC Advances,2017,vol. 7,p. 23432 - 23443

63
manganese(II) perchlorate [ No CAS ]
[ 7325-46-4 ]
[ 7732-18-5 ]
[ 69506-92-9 ]
2C₁₀H₈O₄^(2-)*2C₁₄H₁₄N₄*2Mn⁽²⁺⁾*2H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63.5%	With sodium hydroxide; at 20 - 120℃; for 150.3h;Autoclave;	0.25 mmol of 1,3-bis (imidazole-L-methyl) toluene,0.5 mmol 1,4-benzene diacetic acid and 0.5 mmol manganese perchlorate dissolved in 15 mL distilled water, then add 0.5 mmol sodium hydroxide, stirred at room temperature for 20 min,Then transferred to a polytetrafluoroethylene autoclave, which was placed in a 120 C oven for 150 hours, then cooled to room temperature at 4 C / hour and filtered to obtain a three-dimensional coordination polymer C48H48N8O10Mn2 The rate was 63.5% (based on Mn).

Reference： [1]Patent: CN104130290,2016,B .Location in patent: Paragraph 0022; 0023

64
cadmium nitrate dihydrate [ No CAS ]
[ 7325-46-4 ]
[ 7732-18-5 ]
[ 39642-93-8 ]
C₁₈H₂₂N₄O₂*2H₂O*C₁₀H₈O₄^(2-)*Cd⁽²⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With sodium hydroxide; at 120℃; for 96h;Autoclave; High pressure;	General procedure: A mixture of Cd(NO3)2 ·2H2O (0.068 g), H4btec (0.038 g), L(0.035 g), H2O (10 mL) and NaOH (0.016 g) was stirred for 30 min in air, then the suspension was transferred and sealed in a Teflon lined autoclave, which was heated at 120 C and kept for 4 days, then cooled to room temperature leading to the formation of colorless block crystals for compound 1 in 46% yield based on Cd, and manually pick suitable crystal from the precipitation.

Reference： [1]Journal of Chemical Sciences,2018,vol. 130

65
zinc(II) nitrate hexahydrate [ No CAS ]
[ 7325-46-4 ]
[ 7732-18-5 ]
[ 69506-92-9 ]
[Zn(p-pda)(m-1,4-bis(imidazol-1-ylmethyl)benzene)].H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With potassium hydroxide; at 150℃; under 760.051 Torr; for 72h;Autoclave; High pressure;	A mixture of p-pda (0.0096 g, 0.05 mmol), Zn(NO3)26H2O(0.0297 g, 0.1 mmol), m-bib (0.0238 g, 0.1 mmol) and KOH (0.056g, 0.1 mmol) were added to water (12 mL) in a 25 mL Teflon-linedstainless steel vessel. The mixture was heated at 150 C for 72 h.After the reactive mixture was slowly cooled to room temperature,colourless block crystals of 1 were obtained (yield: 40%, based onZn). Anal. Calc. for C24H24N4O5Zn: C, 56.09; H, 4.71; N, 10.90. Found:C, 55.78; H, 4.84; N, 10.76%. IR (KBr pellet, m/cm-1): 3432m, 3128m,1616s, 1449s, 1366s, 1283m, 1102m, 957m, 860m, 728s.

Reference： [1]Polyhedron,2018,vol. 146,p. 180 - 186

66
[ 7325-46-4 ]
[ 1448297-52-6 ]
C₃₂H₃₈N₄O₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; at 0 - 20℃;	To a solution of 2,2?-(1,4-phenylene)diacetic acid (414 mg, 2.13 mmol) in THF (10 ml) were added VHL-1 (217 mg,0.47 mmol), triethylamine (0.21 ml, 1.4 mmol), and EDCI (110mg, 0.S8mmol) sequentially at0 C. The resulting solution was stirred for 2 h at 0 C, before being warmed to roomtemperature (RT). After stirring overnight at RT, the reaction was quenched with water andconcentrated under reduced pressure. The resulting residue was purified by reverse-phasechromatography to yield the intermediate 18 (170 mg, 60%) as white solid. To a stirring solution of intermediate 18 (20 mg, 0.033 mmol) in DMF (1 ml) were added TEA (0.015 mL, 0.11 mmol), palbociclib (12 mg, 0.027 mmol), and TBTU (12.2 mg, 0.038 mmol). After themixture was stirred at RT overnight, the reaction was concentrated under reduced pressure. Theresulting residue was purified by prep-HPLC to yield the title compound (9 mg, 32%) as yellowsolid. ?H NMR (600 MHz, CD3OD) oe 9.08 (s, 1H), 8.95 (s, 1H), 8.15 (dd, J= 9.7, 2.8 Hz, 1H),7.78 (d, J 2.6 Hz, 1H), 7.51 (d, J 11.4 Hz, 1H), 7.46-7.38 (m, 4H), 7.34-7.25 (m, 4H),6.06-5.97 (m, 1H), 4.66-4.61 (m, 1H), 4.59-4.46 (m, 3H), 4.38-4.32 (m, 1H), 3.92-3.83(m, 3H), 3.81 - 3.70 (m, 4H), 3.64 (d, J= 14.4 Hz, 1H), 3.58 (d, J 14.7 Hz, 1H), 3.24- 3.18(m, 1H), 3.16-3.09 (m, 1H), 3.08-3.02 (m, 1H), 2.52 (s, 3H), 2.49 (s, 3H), 2.44 (s, 3H), 2.37-2.31 (m, 2H), 2.26-2.20(m, 1H), 2.15 -2.08 (m, 3H), 1.96- 1.87(m, 2H), 1.76- 1.68 (m, 2H), 0.97 (s, 9H). HRMS (ESI-TOF) m/z: [M+Hj calculated for C56H66N1107S, 1036.4862; found: 1036.4860.

Reference： [1]Patent: WO2018/106870,2018,A1 .Location in patent: Page/Page column 85; 122; 123

67
[ 7325-46-4 ]
[ 71197-71-2 ]
4,17-dioxabicyclo[18.2.2]tetracosa-1⁽²²⁾,8,12,20,23-pentaene-3,18-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With hafnium tetrakis(trifluoromethanesulfonate); In toluene; at 110℃; for 16h;	General procedure: Dicarboxylic acid (0.2 mmol, 1.0 equiv.) and 1Z,5Z-dienediol (0.2 mmol, 1.0 equiv.) were dissolved in toluene (40 mL, 5 mM). Then Hf(OTf)4 (0.02 mmol, 0.1 equiv.) was added to the solution and the reaction mixture heated to 110 C. The reaction mixture was stirred at this temperature for 16-18 h. After cooling to room temperature, silica gel (~1 mL) was added and the slurry was concentrated under reduced pressure and purified by column chromatography (elution with petroleum ether/EtOAc (20/1)) to afford the desired product as a colorless oil.

Reference： [1]Tetrahedron,2018,vol. 74,p. 4606 - 4612

68
[ 7325-46-4 ]
(5Z,9Z)-tetradeca-5,9-diene-1,14-diol [ No CAS ]
4,19-dioxabicyclo[20.2.2]hexacosa-1⁽²⁴⁾,9,13,22,25-pentaene-3,20-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With hafnium tetrakis(trifluoromethanesulfonate); In toluene; at 110℃; for 16h;	General procedure: Dicarboxylic acid (0.2 mmol, 1.0 equiv.) and 1Z,5Z-dienediol (0.2 mmol, 1.0 equiv.) were dissolved in toluene (40 mL, 5 mM). Then Hf(OTf)4 (0.02 mmol, 0.1 equiv.) was added to the solution and the reaction mixture heated to 110 C. The reaction mixture was stirred at this temperature for 16-18 h. After cooling to room temperature, silica gel (~1 mL) was added and the slurry was concentrated under reduced pressure and purified by column chromatography (elution with petroleum ether/EtOAc (20/1)) to afford the desired product as a colorless oil.

Reference： [1]Tetrahedron,2018,vol. 74,p. 4606 - 4612

69
[ 7325-46-4 ]
(7Z,11Z)-octadeca-7,11-diene-1,18-diol [ No CAS ]
4,23-dioxabicyclo[24.2.2]triaconta-1⁽²⁸⁾,11,15,26,29-pentaene-3,24-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With hafnium tetrakis(trifluoromethanesulfonate); In toluene; at 110℃; for 16h;	General procedure: Dicarboxylic acid (0.2 mmol, 1.0 equiv.) and 1Z,5Z-dienediol (0.2 mmol, 1.0 equiv.) were dissolved in toluene (40 mL, 5 mM). Then Hf(OTf)4 (0.02 mmol, 0.1 equiv.) was added to the solution and the reaction mixture heated to 110 C. The reaction mixture was stirred at this temperature for 16-18 h. After cooling to room temperature, silica gel (~1 mL) was added and the slurry was concentrated under reduced pressure and purified by column chromatography (elution with petroleum ether/EtOAc (20/1)) to afford the desired product as a colorless oil.

Reference： [1]Tetrahedron,2018,vol. 74,p. 4606 - 4612

70
zinc(II) sulfate heptahydrate [ No CAS ]
[ 7325-46-4 ]
[ 81942-56-5 ]
catena-(μ₂-phenylene-1,4-diacetato)-(μ₂-1,1'-hexane-1,6-diylbis(1H-benzimidazole))-zinc [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39.4%	With sodium hydroxide; In water; at 140℃; for 72h;pH 6.6;High pressure;	General procedure: A mixture of Zn(NO)3.6H2O (0.2 mmol, 58.2 mg), L1 (0.1 mmol,34.6 mg), H2PA (0.2 mmol, 33.2 mg) and H2O (10 mL) was placed in a 25 mL Teflon-lined high-pressure container. The pH value of the reaction mixture was adjusted to 6.5 by NaOH (0.4 mL, 0.1 mol/L).The mixture was heated at 140 C for 3 days. Cool to room temperature at 10 C/h to obtain colorless block crystal (yield: 48.7%, based on L1 ligand.

Reference： [1]Polyhedron,2019,vol. 167,p. 44 - 50

71
nickel(II) nitrate hexahydrate [ No CAS ]
[ 7325-46-4 ]
[ 794485-43-1 ]
[ 7732-18-5 ]
C₁₂H₁₀N₄*C₁₀H₈O₄^(2-)*H₂O*Ni⁽²⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium hydroxide; at 120℃; for 72h;Sealed tube; Autoclave;	A mixture of L (10.5 mg, 0.05 mmol), Ni(NO3)26H2O (29.1 mg,0.10 mmol), H2pda (9.71 mg, 0.05 mmol) and NaOH (4.0 mg,0.1 mmol) in H2O (10 ml) was sealed in a Teflon-lined stainlesssteel container and heated at 120 C for 3 days. After being cooledto room temperature, green block crystals of 1 were obtained in 88% yield based on L. Anal. Calc. for C22H20N4O5Ni: C, 55.15; H,4.21; N, 11.69%. Found: C, 54.89; H, 4.32; N, 11.42%. IR (KBr pellet,cm1): 3438 (w), 1550 (s), 1479 (m), 1443 (s), 1392 (s), 1130 (m),1074 (m), 962 (w), 887 (w), 832 (w), 751 (w), 691 (m), 658 (w), 497(w).

Reference： [1]Polyhedron,2019,vol. 167,p. 33 - 38

72
cadmium(II) nitrate tetrhydrate [ No CAS ]
[ 7325-46-4 ]
[ 794485-43-1 ]
C₁₂H₁₀N₄*C₁₀H₈O₄^(2-)*Cd⁽²⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With sodium hydroxide; In water; at 120℃; for 72h;Sealed tube; Autoclave;	General procedure: A mixture of L (10.5 mg, 0.05 mmol), Ni(NO3)26H2O (29.1 mg,0.10 mmol), H2pda (9.71 mg, 0.05 mmol) and NaOH (4.0 mg,0.1 mmol) in H2O (10 ml) was sealed in a Teflon-lined stainlesssteel container and heated at 120 C for 3 days. After being cooledto room temperature, green block crystals of 1 were obtained in 88% yield based on L.

Reference： [1]Polyhedron,2019,vol. 167,p. 33 - 38

73
[ 7325-46-4 ]
[ 29640-90-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sulfuric acid; nitric acid / 1 h / 0 °C / Darkness 2: sodium hydroxide / water / 168 h / Darkness 3: methanol / 1 h / Photolysis

Reference： [1]Yan, Jingjing; MacDonald, John C.; Maag, Alex R.; Coudert, François-Xavier; Burdette, Shawn C. [Chemistry - A European Journal, 2019, vol. 25, # 35, p. 8393 - 8400]

74
[ 7325-46-4 ]
[ 89-58-7 ]
[ 29640-90-2 ]
[ 20357-22-6 ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 8393 - 8400

75
[ 123-75-1 ]
[ 7677-24-9 ]
[ 7325-46-4 ]
C₂₀H₂₆N₄ [ No CAS ]

Reference： [1]ACS Catalysis,2019,vol. 9,p. 7588 - 7595

76
[ 7325-46-4 ]
[ 1352790-41-0 ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium metaperiodate; sulfuric acid; iodine; at 25 - 30℃; for 3h;	Compound 8 was synthesized according to a modified literature procedure. ( Kraszkiewicz et al., Synthesis , 2006, 1195-1199) Iodine (1.2 g, 4.73 mmol) and KI04 (0.34 g, 1.59 mmol) were slowly added to 95% H2SO4 (30 mL). After stirring for 3 h at 25-30 C, a dark brown iodinating solution containing I+ intermediate (2.2 equiv.) was obtained. l,4-Phenylenediacetic acid (0.95 g, 5 mmol) was added in one portion to the brown iodinating solution and the resulting solution was stirred at 25-30 C for 3 h. The light brown solution was cooled down to room temperature and poured on ice. The precipitate was collected by filtration, thoroughly washed with ice cold saturated aqueous Na2S2Cb solution and water until the filtrates were neutral and followed by washing with ethanol. The raw product was recrystallized from ethanol (50 mL) to afford the product as a white solid (1.622 g, 3.64 mmol, 70%). NMR (300 MHz, DMSO-d6): d 3.68 (s, 4H), 7.82 (s, 2H), 12.53 (s; 2H). 13C NMR (75 MHz, DMSO-d6, 6ppm): d 44.3, 101.4, 139.2, 140.5, 171.2.

Reference： [1]Patent: WO2019/169169,2019,A1 .Location in patent: Paragraph 0042

77
[ 7325-46-4 ]
[ 4559-70-0 ]
[ 38661-56-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium persulfate; silver carbonate; In acetonitrile; at 80℃;	Add 2,2 '(1,4-phenyldimethylene) diacetic acid (194.2 mg, 1 mmol), diphenylphosphine oxide (202 mg, 1 mmol), and sodium persulfate (476 mg) to the reaction flask. , 2.0 mmol), silver carbonate (55 mg, 0.2 mmol) and acetonitrile (10 mL) at 80 oC;TLC follows the reaction to completion;The crude product obtained after the reaction was separated by column chromatography (dichloromethane: methanol = 95: 5) to obtain the target product (yield 88%).

Reference： [1]Patent: CN110229188,2019,A .Location in patent: Paragraph 0044

78
[ 935-14-8 ]
[ 7325-46-4 ]

Yield	Reaction Conditions	Operation in experiment
		At -78 C, n-butyllithium (4.8mL, 2.5mol / L, 2.4 equivalent) was added dropwise to a tetrahydrofuran solution (15 mL) of 1,4-diethynylbenzene (630.8 mg, 1.0 equivalent) for 1 h, Add isopropyl alcohol pinacol borate (2.4 mL, 2.4 equivalents) dropwise to the mixed solution, The reaction was continued for 2h, quenched by the addition of a 1,4-dioxane solution of hydrogen chloride (3.8mL, 4M indioxane, 3.0 equivalents), and the reaction was warmed to room temperature. After the solvent was rotary evaporated, the solution was prepared into an acetone solution (0.3M), A potassium peroxymonosulfonate solution (0.5M, 9.2214g, 3.0 equivalents) was added, transferred to 50 C and stirred for 12h, and separated and purified to obtain 689.4 mg of 1,4-benzenediacetic acid with a purity of 71%.

Reference： [1]Patent: CN110330420,2019,A .Location in patent: Paragraph 0053-0057

79
[ 7325-46-4 ]
[ 204777-78-6 ]
(S)-6-[(Diphenyl-p-tolyl-methyl)-amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid [ No CAS ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
rink amide 4-methylbenzhydrylamine resin [ No CAS ]
C₄₁H₆₀N₉O₈PolS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: A sidechainand N-terminus fully protected linear tripeptide (i.e.Fmoc-Arg(Pbf)-Lys(ivDde)-(Lys(Mtt) (n=3) or Orn(Mtt)(n=2)) was initially assembled on the Rink amide MBHAresin based on the Fmoc chemistry-based manual solid phasepeptide synthesis (SPPS) with the following technical details:For each amino acid coupling, 4 equivalents of a Nalpha-Fmoc-protected amino acid, 3.8 equivalents of the couplingreagent HBTU, and 3.8 equivalents of the additive HOBtwere used in the presence of 0.4 M NMM/DMF, and thecoupling reaction was allowed to proceed at room temperaturefor 1 h. A 20% (v/v) piperidine/DMF solution was usedfor Fmoc removal. Subsequently, the N-terminal Fmocgroup was removed, and the side chain Mtt protecting groupon Lys(Mtt) (or Orn(Mtt)) was selectively removed with a1% (v/v) TFA/DCM solution. The two exposed free aminogroups on the resin were then acylated with 1 equivalent of adicarboxylic acid (suberic acid (m=1), adipic acid (m=1/2),or succinic acid (m=0)) at room temperature for 1 h in thepresence of 1.9 equivalents of HBTU and 0.4 MNMM/DMF. The resulting peptidyl-resin was then treated with a 2% (v/v) solution of hydrazine (NH2NH2) in DMF toremove the ivDde protecting group on Lys(ivDde) (2 x 1 h atroom temperature). The newly exposed free amino groupwas then reacted with ethyl 3-isothiocyanatopropionate (5equivalents) at room temperature for 2 x 5 h in the presenceof 0.4 M NMM/DMF. The peptidyl-resin thus obtained wassubsequently treated with a TFA-containing solution (90%(v/v) TFA, 5% (v/v) DCM, 5% (v/v) ddH2O) at room temperaturefor 4 h to cleave the ethyl ester intermediate (8a, 9a,10a, or 11a) off of the resin. Specifically, a cleavage mixturewas filtered and the volatiles in the filtrate were removedwith a stream of nitrogen gas in a well-ventilated fuminghood, and from the residue the crude ethyl ester intermediate(8a, 9a, 10a, or 11a) was precipitated out with cold diethylether. The obtained crude ethyl ester intermediates 8a-11awere then each purified by reversed-phase high performanceliquid chromatography (RP-HPLC) on a semi-preparativeC18 column (1 x 25 cm, 5 mum). The column was eluted witha gradient of ddH2O containing 0.05% (v/v) TFA andacetonitrile containing 0.05% (v/v) TFA at 4.5 mL/min andwas monitored at 214 nm. The pooled desired HPLCfractions were concentrated with a rotary evaporator toremove acetonitrile and the remaining aqueous solutions intermediates 8a-11a as puffy white solids. The exact massesof the purified 8a-11a were confirmed by the unit-resolutionelectrospray ionization-mass spectrometry analysis (positiveion mode). 8a: calculated m/z for [M+H]+ 727.43; found727.73. 9a: calculated m/z for [M+H]+ 699.40; found 699.76.10a: calculated m/z for [M+H]+ 671.37; found 671.69. 11a:calculated m/z for [M+H]+ 657.35; found 657.83.

Reference： [1]Medicinal Chemistry,2020,vol. 16,p. 358 - 367

80
[ 121-00-6 ]
[ 7325-46-4 ]
di(2-tert-butyl-4-methoxyphenol) p-phenylenediacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: 3-tert-Butyl-4-hydroxyanisole; 1,4-phenylenediacetic acid With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 0.0833333h; Stage #2: In N,N-dimethyl-formamide at 35 - 40℃;	49 2-tert-butyl-4-methoxyphenol nicotinate (XH2010) General procedure: Dissolve niacin (0.62 g, 5 mmol) in dimethylformamide (20 mL), then add dicyclohexylcarbodimide (1200 mg, 6 mmol) and stir for 5 minutes. Add 2-tert-butyl-4-methoxyphenol (900 mg, 5 mmol) and keep the temperature for 35-40° C., overnight. Remove dimethylformamide under reduced pressure. Then dissolve the residue with ethyl acetate (50 mL) and water (2 mL), stir for 20 minutes. The liquid through suction filtration was purified with column chromatography (the eluent is ethyl acetate:petroleum ether=3:1) to obtain the product. The yield is 73%. 1H NMR (400 MHz, CDCl3) δ: 1.34 (s, 9H), 3.81 (s, 3H), 6.76-6.81 (m, 1H), 6.97-7.03 (m, 2H), 7.46-7.49 (m, 1H), 8.44-8.47 (dt, J1=8.4 Hz, J2=2.0 Hz, 1H), 8.84-8.86 (dd, J1=4.8 Hz, J2=1.6 Hz, 1H), 9.41-9.42 (d, J=2.0 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ: 30.2, 34.7, 55.6, 110.8, 114.1, 123.7, 124.7, 125.9, 137.7, 142.5, 142.7, 151.5, 154.1, 157.3, 164.6.

Reference： [1]Current Patent Assignee: BIOMEDICAL ANALYSIS CENTER; ACADEMY OF MILITARY MEDICAL SCIENCES; BIOMEDICAL ANALYSIS CENTER ACAD OF MILITARY MEDICA - US10786481, 2020, B2 Location in patent: Page/Page column 9-10; 19-20

81
[ 7325-46-4 ]
[ 81496-81-3 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
60.3%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 25℃; for 24h; Inert atmosphere;	4.2.2. Synthesis of compounds 26-29 and 31-33 General procedure: Under an argon atmosphere, DCC (513 mg, 2 mmol) and DMAP(13 mg, 0.1 mmol) were added to a solution of dihydroartemisinin(569 mg, 2 mmol) and dicarboxylic acid analogues (1 mmol) indichloromethane (15 mL) at 0 °C. The mixture was stirred for 24 hat room temperature before being filtered. The filtrate wasconcentrated under reduced pressure, and the residue was purifiedby silica gel column chromatography to obtain the correspondingcompound.Compound 26.
60.3%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 25℃; for 24h; Inert atmosphere;	4.2.2. Synthesis of compounds 26-29 and 31-33 General procedure: Under an argon atmosphere, DCC (513 mg, 2 mmol) and DMAP(13 mg, 0.1 mmol) were added to a solution of dihydroartemisinin(569 mg, 2 mmol) and dicarboxylic acid analogues (1 mmol) indichloromethane (15 mL) at 0 °C. The mixture was stirred for 24 hat room temperature before being filtered. The filtrate wasconcentrated under reduced pressure, and the residue was purifiedby silica gel column chromatography to obtain the correspondingcompound.Compound 26.

Reference： [1]Bian, Hongzhu; Dong, Xun; Fu, Rong; Li, Congcong; Liu, Chang; Shen, Zhengwu; Xu, Wei; Xu, Zhenye; Zhang, Jinghua; Zhao, Xiaozhen; Zou, Xiaosu [European Journal of Medicinal Chemistry, 2021, vol. 225]
[2]Bian, Hongzhu; Dong, Xun; Fu, Rong; Li, Congcong; Liu, Chang; Shen, Zhengwu; Xu, Wei; Xu, Zhenye; Zhang, Jinghua; Zhao, Xiaozhen; Zou, Xiaosu [European Journal of Medicinal Chemistry, 2021, vol. 225]

82
cadmium(II) nitrate tetrhydrate [ No CAS ]
[ 7325-46-4 ]
[ 69506-91-8 ]
C₁₂H₁₀N₄*H₂O*Cd⁽²⁺⁾*C₁₀H₈O₄^(2-) [ No CAS ]

Reference： [1]CrystEngComm,2022,vol. 24,p. 169 - 181

83
[ 496-74-2 ]
[ 7325-46-4 ]
[ 2765133-39-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With indium(III) iodide; Dimethylphenylsilane In toluene at 60℃; for 6h; Inert atmosphere; Sealed tube;	Dithioacetalization of Oxalic Acid with Benzene-1,2-dithiol: General Procedure General procedure: A magnetic stirrer bar, oxalic acid (45 mg, 0.50 mmol), dithiol (2.4 equiv, 1.2 mmol), and InI3 (23 mg, 0.050 mmol) were successively added to a freshly distilled toluene solution (2.0 mL) in a screw capped test tube under an N2 atmosphere. The test tube was sealed with a cap incorporating a PTFE septum and was then heated to 60 °C. Me2PhSiH (156 mg, 4.00 mol) was separately added into the test tube every 15 min via a syringe for a total of eight additions. The mixture was further stirred at 60 °C for 6 h. After the reaction, the resultant mixture was quenched with a saturated NaOH aqueous solution (3 mL). The aqueous layer was extracted with ethyl acetate (3 mL × 3). The combined organic phases were dried over anhydrous Na2SO4, filtered, and then evaporated under reduced pressure. The crude solidwas recrystallized from hexane to give the corresponding dithioacetal.

Reference： [1]Sakai, Norio; Minato, Kohei; Nakata, Shota; Ogiwara, Yohei [Synthesis, 2022, vol. 54, # 11, p. 2661 - 2668]

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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. 7325-46-4 ] {[proInfo.proName]}

Quality Control of [ 7325-46-4 ]

Related Doc. of [ 7325-46-4 ]

Product Details of [ 7325-46-4 ]

Calculated chemistry of [ 7325-46-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 7325-46-4 ]

Application In Synthesis of [ 7325-46-4 ]

[ 7325-46-4 ] Synthesis Path-Upstream 1~14

[ 7325-46-4 ] Synthesis Path-Downstream 1~83

Related Functional Groups of [ 7325-46-4 ]

Aryls

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 7325-46-4 ]