19829-72-2|2,3-Dihydroxyterephthalic acid| Ambeed

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Quality Control of [ 19829-72-2 ] Purity: 97% SDS Specification

COA

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Product Details of [ 19829-72-2 ]

CAS No. :	19829-72-2
Formula :	C₈H₆O₆
M.W :	198.13
SMILES Code :	O=C(O)C1=CC=C(C(O)=O)C(O)=C1O
MDL No. :	MFCD02181105
InChI Key :	OHLSHRJUBRUKAN-UHFFFAOYSA-N
Pubchem ID :	88273

Safety of [ 19829-72-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 19829-72-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	2
Num. H-bond acceptors	6.0
Num. H-bond donors	4.0
Molar Refractivity	44.41
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	115.06 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.67
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.48
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.49
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.09
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.3
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.49

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.19
Solubility	1.29 mg/ml ; 0.00652 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.5
Solubility	0.0622 mg/ml ; 0.000314 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	0.0
Solubility	198.0 mg/ml ; 1.0 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.46 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.56

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	1.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.28

Application In Synthesis of [ 19829-72-2 ]

* 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 [ 19829-72-2 ]

[ 19829-72-2 ] Synthesis Path-Downstream 1~35

1
[ 3934-96-1 ]
[ 19829-72-2 ]

References: [1]Journal of the Chemical Society,1954,p. 1163.

2
[ 7168-95-8 ]
[ 19829-72-2 ]

References: [1]Arkiv foer Kemi,1941,vol. 14 A,p. 8,9, 17, 18.

3
[ 124-38-9 ]
[ 120-80-9 ]
[ 19829-72-2 ]

Yield	Reaction Conditions	Operation in experiment
95%		2,3-dihydroxyterephthalic acid (1)On a warm, sunny day (28 C., 18% humidity), catechol (TCI, 120.033 g, 1.09 mol) and K2CO3 (316 g, 2.29 mol) were ground together, and the homogeneous mixture was poured into a 500-mL beaker, which was placed in a par-bomb. The bomb was purged three times with 600 psi CO2 before being filled to 860 psi CO2 and placed in an oil bath. The oil bath gradually increased in temperature to 225 C. in 3 h, with an accompanying increase in bomb pressure to 1170 psi. Within 1.25 h, the pressure decreased to 380 psi (250 C.), and the temperature was maintained at 230 C. for 15 hours. The bomb, at 160 psi, was let cool to RT (and placed in the freezer to facilitate opening) and opened. The reaction mixture, a hard gray rock with turquoise and white specks, was combined with 1.5 L water and 1 L conc. HCl. The mixture slowly bubbled and produced beige foam, and after 3 h, the solid chunks were broken apart with a stick and stirred with a magnetic stir bar for 2 h. The beige slurry was then filtered and left to dry on the house vacuum for 14 h. The solid light gray solid was washed with 4 L Millipore water, and left on the house vacuum for 9 days. The dried gray solid was ground to a powder and further dried on the vacuum line for 26 h (95%).1H NMR (400 MHz, MeOD, delta): 7.34 (s, Ar H, 2H).13C NMR (101 MHz, MeOD, delta): 117.8, 120.1, 152.6, 173.2.HRMS-ESI (m/z): [M-H]- calcd for C8HSO6, 197.0092. found, 197.0094.
51%		To catechol (11g, 0.1 mol), dissolved in 300 cm3 of methanol (under nitrogen atmosphere) was added at once sodium hydroxide pellets(8g, 0.2 mol). The resulting solution was allowed to sit overnight and was then evaporated invacuo (105 oC, 32 h) to a light tan, dry powder, which was further treated with excess carbon dioxide (80 atm) at 185 oC(72 h) in a static, stainless-steel bomb. The light tan solid product was acidified with hot aqueous hydrochloric acid (6N), filtered, and washed with hot water. The solid product was dissolved in hot aqueous sodium hydroxide (pH = 9), treated twice with charcoal, and then was acidified again with hydrochloric acid to obtain almost white powder (yield: 51.0 %). Main IR peaks (KBr, cm-1): 3500, nu(OH, str); 1650 nu(C=O, str). 1H NMR chemical shifts (D2O): 7.28 (s, 2H, ArH); 11.3 (s, 2H, OH).

References: [1]Patent: US2015/157746,2015,A1 .Location in patent: Paragraph 0172; 0173; 0174; 0175; 0176; 0177.
[2]Organic Preparations and Procedures International,1999,vol. 31,p. 106 - 109.
[3]Tetrahedron Letters,2001,vol. 42,p. 3567 - 3570.
[4]Polyhedron,2014,vol. 72,p. 135 - 139.
[5]Journal of the Chemical Society. Perkin Transactions 2 (2001),2001,p. 1573 - 1584.
[6]Journal of Medicinal Chemistry,1981,vol. 24,p. 203 - 206.

4
[ 19829-72-2 ]
[ 77-78-1 ]
[ 7168-94-7 ]

References: [1]Justus Liebigs Annalen der Chemie,1966,vol. 694,p. 98 - 109.

5
[ 67-56-1 ]
[ 19829-72-2 ]
[ 75956-62-6 ]

References: [1]Organic Preparations and Procedures International,1999,vol. 31,p. 106 - 109.
[2]Tetrahedron Letters,2001,vol. 42,p. 3567 - 3570.
[3]Angewandte Chemie - International Edition,2010,vol. 49,p. 9730 - 9733.
[4]Journal of the Chemical Society. Perkin Transactions 2 (2001),2001,p. 1573 - 1584.
[5]Journal of Materials Chemistry,2012,vol. 22,p. 909 - 918.
[6]Journal of the American Chemical Society,2014,vol. 136,p. 4965 - 4973.

6
[ 124-38-9 ]
[ 120-80-9 ]
K₂CO₃ [ No CAS ]
[ 19829-72-2 ]

References: [1]Journal of Organic Chemistry,1954,vol. 19,p. 510,512 Anm. c.

7
[ 120-80-9 ]
KHCO₃ [ No CAS ]
[ 303-38-8 ]
[ 19829-72-2 ]

References: [1]Monatshefte fur Chemie,1917,vol. 38,p. 84.
Monatshefte fuer Chemie,1922,vol. 43,p. 61.

9
[ 124-38-9 ]
disodium salt of pyrocatechol [ No CAS ]
[ 19829-72-2 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1891,vol. <2> 44,p. 2.

10
[ 120-80-9 ]
potassium bi carbonate [ No CAS ]
[ 19829-72-2 ]

References: [1]Monatshefte fur Chemie,1917,vol. 38,p. 84.
Monatshefte fuer Chemie,1922,vol. 43,p. 61.

11
potassium salt of/the/ pyrocatechol-carboxylic acid-⁽³⁾ [ No CAS ]
KHCO₃ [ No CAS ]
[ 19829-72-2 ]

References: [1]Monatshefte fur Chemie,1906,vol. 27,p. 1200.

12
[ 15719-64-9 ]
sodium-salt of guaiacol [ No CAS ]
[ 877-22-5 ]
[ 19829-72-2 ]

References: [1]Journal of Organic Chemistry,1944,vol. 9,p. 121.

13
[ 124-38-9 ]
[ 13052-77-2 ]
[ 877-22-5 ]
[ 19829-72-2 ]

References: [1]Journal of Organic Chemistry,1944,vol. 9,p. 121.

14
[ 111-86-4 ]
[ 19829-72-2 ]
2,3-dihydroxy-<i>N</i>,<i>N</i>'-dioctyl-terephthalamide [ No CAS ]

References: [1]Organic Letters,2001,vol. 3,p. 2827 - 2830.

15
[ 19829-72-2 ]
2,3-dihydroxyterephthaloyl chloride [ No CAS ]
[ 364364-86-3 ]

References: [1]Organic Letters,2001,vol. 3,p. 2827 - 2830.

16
[ 19829-72-2 ]
[ 75-04-7 ]
[ 117918-05-5 ]

References: [1]Organic Letters,2001,vol. 3,p. 2827 - 2830.

17
[ 19829-72-2 ]
[ 364364-86-3 ]

References: [1]Organic Letters,2001,vol. 3,p. 2827 - 2830.

18
[ 19829-72-2 ]
[ 80067-65-8 ]