[ CAS No. 10397-52-1 ] {[proInfo.proName]}

Name: 10397-52-1|5,5'-Methylenediisophthalic acid|98%
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Quality Control of [ 10397-52-1 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 10397-52-1 ]

CAS No. :	10397-52-1	MDL No. :	MFCD19053170
Formula :	C₁₇H₁₂O₈	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RAESDWWKTFZWJA-UHFFFAOYSA-N
M.W :	344.27	Pubchem ID :	15840395
Synonyms :

Safety of [ 10397-52-1 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P272-P273-P280-P302+P352-P333+P313-P362+P364-P391-P501	UN#:
Hazard Statements:	H317-H400	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 10397-52-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 10397-52-1 ]

[ 10397-52-1 ] Synthesis Path-Downstream 1~40

2
[ 10397-51-0 ]
[ 10397-52-1 ]

Yield	Reaction Conditions	Operation in experiment
91%		A mixture of 3,3',5,5'- Tetrakis(methoxycarbonyl)diphenylmethane (19) (1.2g, 3.0 mmol), THF (50 mL) and NaOH (1.92 g, 48 mmol) dissolved in water (50 mL) was refluxed for 1 h. Then, the organic solvent was removed under reduced pressure, and the aqueous solution was refluxed again for 4 h. The reaction mixture was cooled and acidified with 50 % H2SO4. The precipitate was filtered, washed with water, and dried. Yield 91%. M.p. 348-350 C. 1H-NMR (400 MHz, DMSO-d6): δ= 4.29 (s, 2H), 8.08 (d, 4H, J = 1.5 Hz), 8.34 (t, 2H, J = 1.5 Hz), 13.26 (s, 4H). 13C-NMR (100 MHz, DMSO-d6): δ= 39.8, 128.1, 131.5, 133.6, 141.9, 166.5. MS-EI, m/z (%):344 (55) [M+], 299.26 (100), 179 (12), 165 (20).

Reference： [1]European Journal of Organic Chemistry,2007,p. 3271 - 3276
[2]Patent: EP1972338,2008,A1 .Location in patent: Page/Page column 16

3
[ 10397-52-1 ]
[ 949110-27-4 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In tetrahydrofuran; for 3h;Heating / reflux;	A mixture of <strong>[10397-52-1]3,3',5,5'-tetracarboxydiphenylmethane</strong> (0.2g, 0.58 mmol) and thionyl chloride (0.34 mL, 4.65 mmol), in THF (20 mL) was heated under reflux for 3h. The solvent was removed in vacuum. Then, THF (4 x 20 mL) was added and again the solvent was removed in vacuum. The crude product was directly used for further reaction.

Reference： [1]European Journal of Organic Chemistry,2007,p. 3271 - 3276
[2]Patent: EP1972338,2008,A1 .Location in patent: Page/Page column 16

4
[ 121-91-5 ]
[ 10397-52-1 ]

Reference： [1]European Journal of Organic Chemistry,2007,p. 3271 - 3276

5
[ 10397-52-1 ]
N,N',N'',N'''-tetrakis[(2-hydroxy-5-methyl-phenyl)]biphenyl-3,3',5,5'-tetracarboxamide [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2007,p. 3271 - 3276
[2]Patent: EP1972338,2008,A1

6
[ 50-00-0 ]
[ 121-91-5 ]
[ 10397-52-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; sulfur trioxide; at 0 - 118℃; for 6h;Product distribution / selectivity;	Isophthalic acid (18) (33 g, 0.2 mol) was dissolved in 100 mL of 20 % oleum. To the solution, 95 % paraformaldehyde (3.1 g, 0.1 mol) was added. The mixture was maintained at 118C for 6 hours. After cooling down to room temperature, the mixture was poured onto ice water. The precipitate was filtered, washed with water, and dried in a vacuum. The yellow solid was dissolved in methanol (100 mL), saturated with HCl and refluxed for 30 min. The mixture was cooled to 10C and the solid product which appeared was filtered, washed with cold methanol, and dried. To remove last impurities, the solid was recrystallized from benzene and from ethylacetate. Yield 12%. M.p. 197-198 C. 1H-NMR (400 MHz, CDCl3): δ= 3.93 (s, 12H), 4.16 (s, 2H), 8.05 (d, 4H, J = 1.5 Hz), 8.55 (t, 2H, J = 1.5 Hz). 13C-NMR (100 MHz, CDCl3): δ= 41.1, 52.4, 129.1, 131.1, 134.2, 140.8, 166.1. Rf= 0.93 (silica gel, methanol/chloroform, 1:7 v/v). MS-EI, m/z (%): 400 (55) [M+], 369 (100), 341 (22), 281 (18).
	With sulfuric acid; at 118℃; for 6h;	Isophthalic acid (33.0 g, 0.20 mol) and 95% paraformaldehyde (3.1 g, 0.10 mol) were dissolved in 100 mL of 20% fuming sulfuric acid, and the mixture was stirred at 118 C. for 6 hours.After cooling to room temperature, the mixture was poured onto ice-water, the precipitate was filtered, washed with water, and dried in vacuo to give a yellow solid.The obtained yellow solid was dissolved in 100 mL of methanol, and 220 mL of hydrochloric acid was added and refluxed for 30 minutes.The mixture was cooled to 10 C, and the solid product that appeared was filtered, washed with cold methanol and dried.The product was obtained as a white solid 4.40 g in a yield of 11%.

Reference： [1]Patent: EP1972338,2008,A1 .Location in patent: Page/Page column 15-16
[2]Patent: CN110467636,2019,A .Location in patent: Paragraph 0022-0023

7
[ 67-56-1 ]
[ 10397-52-1 ]
[ 10397-51-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; at 10℃; for 0.5h;Heating / reflux;	Isophthalic acid (18) (33 g, 0.2 mol) was dissolved in 100 mL of 20 % oleum. To the solution, 95 % paraformaldehyde (3.1 g, 0.1 mol) was added. The mixture was maintained at 118C for 6 hours. After cooling down to room temperature, the mixture was poured onto ice water. The precipitate was filtered, washed with water, and dried in a vacuum. The yellow solid was dissolved in methanol (100 mL), saturated with HCl and refluxed for 30 min. The mixture was cooled to 10C and the solid product which appeared was filtered, washed with cold methanol, and dried. To remove last impurities, the solid was recrystallized from benzene and from ethylacetate. Yield 12%. M.p. 197-198 C. 1H-NMR (400 MHz, CDCl3): δ= 3.93 (s, 12H), 4.16 (s, 2H), 8.05 (d, 4H, J = 1.5 Hz), 8.55 (t, 2H, J = 1.5 Hz). 13C-NMR (100 MHz, CDCl3): δ= 41.1, 52.4, 129.1, 131.1, 134.2, 140.8, 166.1. Rf= 0.93 (silica gel, methanol/chloroform, 1:7 v/v). MS-EI, m/z (%): 400 (55) [M+], 369 (100), 341 (22), 281 (18).

Reference： [1]Patent: EP1972338,2008,A1 .Location in patent: Page/Page column 15-16

8
copper nitrate hemi(pentahydrate) [ No CAS ]
[ 10397-52-1 ]
[ 67-68-5 ]
[Cu₂(C(2v)-5,5'-methylene-di-isophthalate)(H₂O)3]*3dimethylsulfoxide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 7263 - 7266

9
copper nitrate hemi(pentahydrate) [ No CAS ]
[ 127-19-5 ]
[ 10397-52-1 ]
[Cu₆(C(s)-5,5'-methylene-di-isophthalate)2(C(2v)-5,5'-methylene-di-isophthalate)(H₂O)6]*3dimethylacetamide*6H₂O [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 7263 - 7266

10
[ 821-41-0 ]
[ 10397-52-1 ]
[ 1244029-34-2 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 6708 - 6711

11
zinc(II) acetate hexahydrate [ No CAS ]
[ 10397-52-1 ]
[ 1310-73-2 ]
Zn5(methylenediisophthalate)2(H2O)6(μ3-OH)2*2H2O [ No CAS ]

Reference： [1]Inorganic Chemistry Communications,2010,vol. 13,p. 818 - 821

12
cerium(III) nitrate hexahydrate [ No CAS ]
[ 10397-52-1 ]
[Ce(methylenediisophthalate^(3-))(water)]*water [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 14321 - 14323

13
cerium(III) nitrate hexahydrate [ No CAS ]
[ 10397-52-1 ]
[Ce(methylenediisophthalate^(3-))(water)]*2water [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 14321 - 14323

14
[ 1307-96-6 ]
[ 10397-52-1 ]
[ 7732-18-5 ]
[ 33513-42-7 ]
[H₃O]2[Co₃(methylenediisophthalic acid(-4H))2]*2DMF [ No CAS ]

Reference： [1]Dalton Transactions,2010,vol. 39,p. 9123 - 9130

15
[ 1313-99-1 ]
[ 10397-52-1 ]
[ 7732-18-5 ]
[ 33513-42-7 ]
[Ni2(methylenediisophthalic acid(-3H))(μ2-OH)(H2O)3(DMF)]*8H2O [ No CAS ]

Reference： [1]Dalton Transactions,2010,vol. 39,p. 9123 - 9130

16
copper(II) nitrate trihydrate [ No CAS ]
[ 10397-52-1 ]
[ 7732-18-5 ]
[Cu3(methylenediisophthalic acid(-4H))(μ2-OH)2(H2O)4]*6.5H2O [ No CAS ]

Reference： [1]Dalton Transactions,2010,vol. 39,p. 9123 - 9130

17
nickel(II) nitrate hexahydrate [ No CAS ]
1,1'-(1,4-butanediyl)bis(imidazole) [ No CAS ]
[ 10397-52-1 ]
Ni₄(methylenediisophthalate)2(1,1'-(1,4-butanediyl)bis(imidazole)2tetraaqua*H₂O [ No CAS ]

Reference： [1]Inorganic Chemistry Communications,2010,vol. 13,p. 1239 - 1243

18
zinc(II) nitrate hexahydrate [ No CAS ]
1,1'-(1,4-butanediyl)bis(imidazole) [ No CAS ]
[ 10397-52-1 ]
Zn₂(methylenediisophthalate)2(1,1'-(1,4-butanediyl)bis(imidazole)diaqua*H₂O [ No CAS ]

Reference： [1]Inorganic Chemistry Communications,2010,vol. 13,p. 1239 - 1243

19
[ 5632-13-3 ]
[ 10397-52-1 ]
[ 1248339-38-9 ]

Reference： [1]Dalton Transactions,2010,vol. 39,p. 7727 - 7732

20
cobalt(II) nitrate hexahydrate [ No CAS ]
[ 10397-52-1 ]
[ 69506-92-9 ]
[Co₂(methylenediisophthalic acid)(1,3-bis(imidazole-1-ylmethyl)benzene)₂]*2H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	In water; at 120℃; for 72h;Autoclave; Heating;	General procedure: [Co2(L)(m-bix)2]⋅2H2O (2) 2 was prepared with the similar method as 1, using Co(NO3)2⋅6H2O instead of Ni(NO3)2⋅6H2O, m-bix instead of o-bix. ;Purple single crystals were collected in 63% yield on the basis of cobalt. C45H40Co2N8O10 Elemental analysis calcd. (%) C, 55.68; H, 4.15; N, 11.54. Found: C, 55.65; H, 4.17; N, 11.52. FTIR (KBr cm-1): 3432(s), 3130(m), 3077(w), 2933(w), 2585(w), 1691(m), 1621(s), 1587(m), 1517(m), 1452(m), 1383(vs), 1314(m), 1277(m), 1213(m), 1112(w), 1090(w), 1028(w), 947(w), 910(w), 849(w), 806(w), 766(m), 723(m), 656(w), 624(w), 596(w), 557(w), 466(w).

Reference： [1]Journal of Molecular Structure,2014,vol. 1056-1057,p. 333 - 338

21
nickel(II) nitrate hexahydrate [ No CAS ]
[ 10397-52-1 ]
[ 42032-51-9 ]
[Ni₂(methylenediisophthalic acid)(1,2-bis(imidazole-1-ylmethyl)benzene)₂(H₂O)₂]*H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In water; at 120℃; for 72h;Autoclave; Heating;	General procedure: Synthesis;[Ni2(L)(o-bix)2(H2O)2]⋅H2O (1) 1 was synthesized hydrothermally in a 25 mL Teflon-lined autoclave by heating a mixture of 0.1 mmol H4L, 0.1 mmol o-bix, 0.2 mmol Ni(NO3)2⋅6H2O, and H2O (10 mL) at 120 C for 3 days. Green single crystals were collected in 78% yield on the basis of nickel. C45H42N8Ni2O11 Elemental analysis calcd. (%) C, 54.69; H, 4.28; N, 11.34. Found: C, 54.55; H, 4.30; N, 11.31. FTIR (KBr cm-1): 3410(s), 3125(m), 1616(s), 1561(s), 1524(s), 1445(s), 1402(s), 1356(s), 1228(m), 1105(m), 1090(s), 1032(w), 946(w), 821(w), 804(w), 775(m), 729(s), 683(w), 657(s), 625(w), 596(w), 567(w), 538(w), 530(w), 510(w), 481(w), 463(w), 443(w), 434(w).

Reference： [1]Journal of Molecular Structure,2014,vol. 1056-1057,p. 333 - 338

22
zinc(II) nitrate hexahydrate [ No CAS ]
[ 57654-36-1 ]
[ 10397-52-1 ]
[ 7732-18-5 ]
[ 33513-42-7 ]
[Zn(3,3′,5,5′-tetracarboxylatediphenylmethane)(3,6-di-pyridin-4-yl-[1,2,4,5]tetrazine)]*DMF*2H2O [ No CAS ]

Reference： [1]Dalton Transactions,2014,vol. 43,p. 6100 - 6107

23
zinc(II) nitrate hexahydrate [ No CAS ]
[ 10397-52-1 ]
[ 7732-18-5 ]
[ 113682-56-7 ]
[ 68-12-2 ]
[Zn2(3,3′,5,5′-tetracarboxylatediphenylmethane)(4,4'-bispyridylphenyl)]*3DMF*4H2O [ No CAS ]