[ CAS No. 385-00-2 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 385-00-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 385-00-2 ]

SDS Specification

Alternatived Products of [ 385-00-2 ]

Product Citations Expand+

Lanthanide Metal–Organic Frameworks Exhibiting Fluoro-Bridged Extended Chains: Synthesis, Crystal Structures, and Magnetic Properties

Marie L. Mortensen ; Shubham Bisht ; Muhammad Abbas , et al. Inorg. Chem.,2024,63(1):219-228. DOI: 10.1021/acs.inorgchem.3c03064

Abstract: Two fluoro-bridged lanthanide-containing metal–organic frameworks (MOFs) were synthesized using 2,2′-bipyridine-4,4′-dicarboxylic acid (BPDC), a fluorinated modulator, and a lanthanide nitrate. The syntheses of MOFs containing Gd3+ or Tb3+ and a closely related MOF structure containing Ho3+, Gd3+, or Tb3+ are presented. The presence of the fluorinated metal chains in these MOFs is shown through single crystal X-ray diffraction, energy dispersion X-ray spectroscopy, 19F nuclear magnetic resonance, and X-ray photoelectron spectroscopy. Magnetic measurements reveal weak antiferromagnetic exchange between the Ln3+ ions mediated by fluoride anions along the zigzag ladder chains present in the crystal structures of these MOFs.

Purchased from AmBeed: 385-00-2

Photophysical Properties of Rare-Earth Cluster-Based Metal–Organic Frameworks

Ajoyan, Zvart ; Concordia University,2021.

Abstract: The work described herein explores the field of metal–organic frameworks (MOFs) with a particular emphasis on rare-earth (RE) cluster-based MOFs. MOFs are materials that are of interest due to their permanent porosity, high surface areas, and tunable structures. This thesis focuses on three different MOFs: RE-UiO-66 (UiO = University of Oslo), RE-CU-10 and RE-CU-27 (CU = Concordia University). The synthesis, characterization, and photophysical properties of these MOFs are presented. Chapter 2 explores tuning of the RE-UiO-66 platform by synthesizing and characterizing mono-, bi- and tri-metal RE-UiO-66 analogues where RE = Tb(III), Gd(III), and Eu(III), ultimately leading to the formation of a white light emitting MOF. Furthermore, a study of the photophysical properties of this series of MOFs is conducted and as a proof of concept, Tb:Gd:Eu-UiO-66 is deposited on a UV light emitting diode (LED), leading to a white light emitting diode (WLED). Chapter 3 describes a facile route for modulating the photoluminescent and radioluminescent properties of Tb(III) cluster-based MOFs. By using Tb(III)-cluster nodes as Xray attenuators, and organic linkers with varying excited state energies as sensitizers, MOFs with metal-based, linker-based, and metal+linker-based photo- and radioluminescence are reported.

Purchased from AmBeed: 385-00-2

Product Details of [ 385-00-2 ]

CAS No. :	385-00-2	MDL No. :	MFCD00002411
Formula :	C₇H₄F₂O₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	ONOTYLMNTZNAQZ-UHFFFAOYSA-N
M.W :	158.10	Pubchem ID :	9796
Synonyms :

Calculated chemistry of [ 385-00-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	33.32
TPSA :	37.3 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.14 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.14
Log Po/w (XLOGP3) :	1.59
Log Po/w (WLOGP) :	2.5
Log Po/w (MLOGP) :	2.47
Log Po/w (SILICOS-IT) :	2.06
Consensus Log Po/w :	1.95

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.16
Solubility :	1.09 mg/ml ; 0.00693 mol/l
Class :	Soluble
Log S (Ali) :	-1.98
Solubility :	1.64 mg/ml ; 0.0104 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.32
Solubility :	0.764 mg/ml ; 0.00483 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.01

Safety of [ 385-00-2 ]

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

Application In Synthesis of [ 385-00-2 ]

* 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.

Upstream synthesis route of [ 385-00-2 ]
Downstream synthetic route of [ 385-00-2 ]

[ 385-00-2 ] Synthesis Path-Upstream 1~1

1
[ 385-00-2 ]
[ 6185-28-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydroxide In ethanol; water at 20℃; for 0.166667 h;	Sodium 2,6-difluorobenzoate; To a solution of 2,6-difluorobenzoic acid (1.0Og₁ 6.3mmol) in EtOH and water (5:1 , 6OmL) was added 1 N aqueous sodium hydroxide solution (6.33mL, 6.3mmol). The reaction mixture was stirred for 10 minutes at room temperature and then solvents were removed in vacuo to yield sodium 2,6-difluorobenzoate (1.22g, 6.3mmol, quantitative) as an off white solid. ¹H NMR (DMSO) δ 6.89 (2H, m), 7.15 (1 H, m).

Reference： [1] Patent: WO2008/139161, 2008, A1, . Location in patent: Page/Page column 89

[ 385-00-2 ] Synthesis Path-Downstream 1~4

1
[ 385-00-2 ]
[ 13671-00-6 ]

Reference： [1]Journal of Medicinal Chemistry,1968,vol. 11,p. 814 - 819

2
[ 67-56-1 ]
[ 18063-02-0 ]
[ 13671-00-6 ]
[ 385-00-2 ]

Reference： [1]Journal of Physical Organic Chemistry,2012,vol. 25,p. 267 - 270

3
[ 67-56-1 ]
[ 385-00-2 ]
[ 13671-00-6 ]

Yield	Reaction Conditions	Operation in experiment
82%	With sulfuric acid; for 6h;Reflux;	General procedure: A catalytic amount of concentrated H2SO4 wasadded to a solution of carboxylic acids 16(a-j) (1.0 mmol)in 50 mL of methanol, and the mixture was refluxed for 6 h. It was allowed to cool. The saturated solution ofNaHCO3 was added to the reaction mixture, and it wasextracted with EtOAc (2 X 50 mL). The combined organiclayer was dried Na2SO4 and concentrated to obtain puremethyl esters 17(a-j).
75.9%	With toluene-4-sulfonic acid;Inert atmosphere; Reflux;	To a suspension of 2,6-difluorobenzoic acid (50 g, 316 mmol) in MeOH (800 mL) was added TsOH ( 6 g, 10%), the mixture was heated to reflux overnight. The solvent was removed under reduced pressure. The residue was dissolved in EtOAc and washed with saturated NaHCO3 and brinesuccessively. The organic layer was separated, dried over Na2SO and concentrated under reduced pressure to give methyl 2,6-difluorobenzoate. 41 g (75.9% yield) 1 H NMR (400 MHz, CDCI3) delta ppm 7.37-7.46 (m, 1 H), 6.91 - 6.98 (m, 2H), 3.95 (s, 3H).
73%		Step 2: methyl 2,6-difluorobenzoateTo a solution of 2,6-difluorobenzoic acid (100 g, 0.63 mol) in sulfurous dichloride (150 mL) and the resulting reaction mixture was heated to refluxing for 2 hrs. Sulfurous dichloride was removed in vacuo, the residue in pyridine (100 ml) was added MeOH (100 mL) slowly and stirred at room temperature for 2 hrs. The solvent was removed in vacuo, the residue was dissolved in EtOAc (200 mL) and washed with aqueous NaOH (IN), HC1 (IN) and brine. The solution was dried over Na2S04, filtered and concentrated to afford the desired product (78.8 g, 73%).1H NMR (CDCI3): ? 7.46-7.38 (1H, m), 6.98-9.93 (2H, m), 3.95 (3H, d, J = 2.0 Hz).

73%		2,6-difluorobenzoic acid (10 (^, 0.63111001) was dissolved in thionyl chloride (1501 ^), and the resulting mixture was heated under reflux for 2 hours. The excess sodium sulfoxide was distilled off and the resulting residue (100 mL) was added dropwise and the methanol was slowly added dropwise (100 mL). The reaction was stirred at room temperature for 2 hours and the solvent was removed in vacuo to remove the solvent. The resulting oil was dissolved in 200 mL of ethyl acetate and treated with IN sodium hydroxide solution, IN hydrochloric acid , Water and saturated salt water. After evaporation of the solvent in vacuo, the title compound (78.8 g, 73%) was obtained as an oil.
71%	With sulfuric acid; at 20℃;Reflux;	To a solution of 2,6-difluorobenzoic acid (30.0 g, 190.0 mmol) in MeOH (100 mL) was added concentrated sulfuric acid (5 mL) dropwise at room temperature. The reaction mixture was heated under reflux overnight. The solvent was removed in vacuo. The residue was dissolved in EtOAc and washed with saturated NaHCO3 and brine. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give 1 (23.2 g, 71%) as a yellow oil. 1H NMR (CDCl3): delta 7.45-7.39 (m, 1H), 6.98-6.93 (m, 2H), 3.96 (s, 3H).

Reference： [1]Organic Process Research and Development,2016,vol. 20,p. 233 - 241
[2]Medicinal Chemistry Research,2016,vol. 25,p. 627 - 643
[3]Patent: WO2011/59610,2011,A1 .Location in patent: Page/Page column 101-102
[4]Patent: WO2013/71865,2013,A1 .Location in patent: Page/Page column 25
[5]Patent: CN103102349,2017,B .Location in patent: Paragraph 0147-0149
[6]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1017 - 1021

4
[ 13671-00-6 ]
[ 125309-34-4 ]
[ 385-00-2 ]

Yield	Reaction Conditions	Operation in experiment
54%	With hydroxylamine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; water; at 20℃; for 2h;	1,8-Diazabicyclo[5.4.0]undec-7-ene (0.43 ml, 2.90 mmol, 5.0 eq) wasadded to a solution of <strong>[13671-00-6]methyl 2,6-difluorobenzoate</strong> (100 mg, 0.58 mmol, 1.0 eq) in methanol (0.35 mL). The resulting solutionwas stirred at room temperature and hydroxylamine in aqueous solution 50% (0.36ml, 5.81 mmol, 10.0 eq) was added. After 2h the reaction was stopped and themixture is adjusted to pH 6 with acetic acid. The aqueous layer was extractedthree times with ethyl acetate. The combined organic layer was dried with MgSO4,concentrated and purified by preparative HPLC to afford 2,6-difluoro-N-hydroxy-benzamide (54 mg, 0.31 mmol, 54 %) as a white solid: MS ES+ m/z 174.1 (M+H)+; 1HNMR (400 MHz, DMSO-d6) delta 11.18 (s, 1H), 9.41 (s, 1H), 7.54 (m, 1H), 7.22 - 7.14 (m, 2H); 13CNMR (101 MHz, DMSO-d6) delta 159.3 (dd, J = 249.9, J = 8.4 Hz), 156.6, 132.2 (t, J = 10.3 Hz), 113.3 (t, J = 23.3 Hz), 112.1 (dd, J = 19.7, J = 5.4 Hz) ; 19FNMR (377 MHz, DMSO-d6) delta -113.6 (t, J = 7.0 Hz).

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 2165 - 2170

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Arndt-Eistert Homologation ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Friedel-Crafts Reaction ? Hunsdiecker-Borodin Reaction ? Hydrogenolysis of Benzyl Ether ? Passerini Reaction ? Preparation of Alkylbenzene ? Preparation of Amines ? Preparation of Carboxylic Acids ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Carboxylic Acids ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Ugi Reaction ? Vilsmeier-Haack Reaction

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[ CAS No. 385-00-2 ] {[proInfo.proName]}

Quality Control of [ 385-00-2 ]

Related Doc. of [ 385-00-2 ]

Product Citations Expand+

Product Details of [ 385-00-2 ]

Calculated chemistry of [ 385-00-2 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 385-00-2 ]

Application In Synthesis of [ 385-00-2 ]

[ 385-00-2 ] Synthesis Path-Upstream 1~1

[ 385-00-2 ] Synthesis Path-Downstream 1~4

Technical Information

Related Functional Groups of [ 385-00-2 ]

Fluorinated Building Blocks

Aryls

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 385-00-2 ]