[ CAS No. 195136-58-4 ] {[proInfo.proName]}

Name: 195136-58-4|2',7'-Difluoro-3',6'-dihydroxy-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one|98+%
Brand: Ambeed
SKU: A756917
Price: 135.0 USD
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2D 3D

Structure of 195136-58-4 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 195136-58-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 195136-58-4 ]

SDS Specification

Alternatived Products of [ 195136-58-4 ]

Product Details of [ 195136-58-4 ]

CAS No. :	195136-58-4	MDL No. :	MFCD01311849
Formula :	C₂₀H₁₀F₂O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FJXJIUHGLVUXQP-UHFFFAOYSA-N
M.W :	368.29	Pubchem ID :	10292443
Synonyms :	Oregon Green™ 488;OG 488;2’,7’-Difluorofluorescein

Calculated chemistry of [ 195136-58-4 ]

Physicochemical Properties

Num. heavy atoms :	27
Num. arom. heavy atoms :	18
Fraction Csp3 :	0.05
Num. rotatable bonds :	0
Num. H-bond acceptors :	7.0
Num. H-bond donors :	2.0
Molar Refractivity :	88.66
TPSA :	75.99 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.59
Log Po/w (XLOGP3) :	3.62
Log Po/w (WLOGP) :	4.68
Log Po/w (MLOGP) :	3.24
Log Po/w (SILICOS-IT) :	4.19
Consensus Log Po/w :	3.66

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.9
Solubility :	0.00467 mg/ml ; 0.0000127 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.9
Solubility :	0.0046 mg/ml ; 0.0000125 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-6.69
Solubility :	0.0000752 mg/ml ; 0.000000204 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	3.5

Safety of [ 195136-58-4 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 195136-58-4 ]

* 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.

Downstream synthetic route of [ 195136-58-4 ]

[ 195136-58-4 ] Synthesis Path-Downstream 1~17

1
[ 1656-44-6 ]
[ 195136-58-4 ]
[ 827020-43-9 ]

Yield	Reaction Conditions	Operation in experiment
67%	With 2,6-dimethylpyridine In dichloromethane at 20℃;

Reference： [1]Maeda, Hatsuo; Yamamoto, Kayoko; Nomura, Yoko; Kohno, Iho; Hafsi, Leila; Ueda, Noritsugu; Yoshida, Shoko; Fukuda, Masako; Fukuyasu, Yuka; Yamauchi, Yuji; Itoh, Norio [Journal of the American Chemical Society, 2005, vol. 127, # 1, p. 68 - 69]

2
[ 195136-58-4 ]
[ 913689-08-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 67 percent / 2,6-lutidine / CH₂Cl₂ / 20 °C 2: aq. hypoxanthine; xanthine oxidase / dimethylsulfoxide; various solvent(s) / 37 °C / pH 7.4

Yield	Reaction Conditions	Operation in experiment
		90 Preparation of 2',7'-difluorofluorescein, tetra-O-acetylgalactoside (90) Example 90 Preparation of 2',7'-difluorofluorescein, tetra-O-acetylgalactoside (90) Using general method O, 2',7'-difluorofluorescein (29, 70 mg, 0.19 mmol, Rf =0.13 (CHCl3 /methanol/acetic acid 50:5:1)) gives Compound 90 as 0.12 g (92%) of a yellow foam: Rf =0.31 (CHCl3 /methanol/acetic acid 50:5:1).

4
[ 85-44-9 ]
[ 103068-41-3 ]
[ 195136-58-4 ]

Yield	Reaction Conditions	Operation in experiment
85%		Example 30 Preparation of 2',7'-difluorofluorescein (29) Following general method H, Compound 29 is obtained from Compound 15 and phthalic anhydride in 85% yield. 1 H-NMR (d6 -DMSO) 7.99 (d, 1H), 7.79 (t, 1H), 7.72 (t, 1H), 7.29 (d, 1H), 6.89 (d, 2H), 6.48 (d, 2H).

Reference： [1]European Journal of Organic Chemistry,2010,p. 3569 - 3573
[2]Patent: US6162931,2000,A

Yield	Reaction Conditions	Operation in experiment
	With oxygen UV-irradiation;

6
[ 358-23-6 ]
[ 195136-58-4 ]
2',7'-difluoro-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-3',6'-diyl bis(trifluoromethanesulfonate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With pyridine In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere;

Reference： [1]Grimm, Jonathan B.; Lavis, Luke D. [Organic Letters, 2011, vol. 13, # 24, p. 6354 - 6357]

7
[ 195136-58-4 ]
3,6-diamino-9-(2-carboxyphenyl)-2,7-difluoroxanthylium trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: pyridine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 18 h / 100 °C / Inert atmosphere 3: dichloromethane / 2 h / 20 °C / Inert atmosphere

Reference： [1]Grimm, Jonathan B.; Lavis, Luke D. [Organic Letters, 2011, vol. 13, # 24, p. 6354 - 6357]

8
[ 195136-58-4 ]
di-tert-butyl (2',7'-difluoro-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-3',6'-diyl)dicarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 18 h / 100 °C / Inert atmosphere

Reference： [1]Grimm, Jonathan B.; Lavis, Luke D. [Organic Letters, 2011, vol. 13, # 24, p. 6354 - 6357]

9
[ 75-36-5 ]
[ 195136-58-4 ]
[ 1027558-93-5 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; dmap In dichloromethane for 1h;

Reference： [1]Chyan, Wen; Kilgore, Henry R.; Gold, Brian; Raines, Ronald T. [Journal of Organic Chemistry, 2017, vol. 82, # 8, p. 4297 - 4304]

10
[ 195136-58-4 ]
2',7'-difluoro-3'-hydroxy-6'-isopropoxy-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 15 h / Inert atmosphere 2: sodium hydroxide / methanol; water / 15 h

Reference： [1]Becker, Katja; Busker, Sander; Felber, Jan G.; Maier, Martin S.; Poczka, Lena; Scholzen, Karoline; Theisen, Ulrike; Thorn-Seshold, Julia; Thorn-Seshold, Oliver; Zeisel, Lukas; Arnér, Elias S. J.; Brandstädter, Christina [Journal of the American Chemical Society, 2021, vol. 143, # 23, p. 8791 - 8803]

11
[ 195136-58-4 ]
cis-2',7'-difluoro-3'-isopropoxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthen]-6'-yl-hexahydro-[1,2]dithiino[4,5-b]pyridine-1(2H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 15 h / Inert atmosphere 2: sodium hydroxide / methanol; water / 15 h 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 4: N-ethyl-N,N-diisopropylamine / dichloromethane / 2.5 h / 0 - 20 °C

12
[ 195136-58-4 ]
cis-2',7'-difluoro-3'-isopropoxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthen]-6'-yl hexahydrofuro[3,4-b]pyridine-1(2H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 15 h / Inert atmosphere 2: sodium hydroxide / methanol; water / 15 h 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 4: N-ethyl-N,N-diisopropylamine / dichloromethane / 2.5 h / 0 - 20 °C

13
[ 195136-58-4 ]
2',7'-difluoro-3'-isopropoxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthen]-6'-yl ((S)-1,2-dithian-4-yl)(methyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 15 h / Inert atmosphere 2: sodium hydroxide / methanol; water / 15 h 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 4: N-ethyl-N,N-diisopropylamine / dichloromethane / 2.5 h / 0 - 20 °C

14
[ 195136-58-4 ]
C₂₄H₁₅ClF₂O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 15 h / Inert atmosphere 2: sodium hydroxide / methanol; water / 15 h 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

15
[ 75-30-9 ]
[ 195136-58-4 ]
C₂₆H₂₂F₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In N,N-dimethyl-formamide for 15h; Inert atmosphere;

16
chloroacetamidomethanol [ No CAS ]
[ 195136-58-4 ]
4'-Aminomethyl Difluoro-Fluorescein [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		29 Synthesis of 4'-Aminomethyl Difluoro-Fluorescein (4-AMDFF) Example 29 Synthesis of 4'-Aminomethyl Difluoro-Fluorescein (4-AMDFF) 4-AMDFF, i.e.: was prepared according to the following synthetic scheme: 0.1 g of chloroacetamidomethanol (CLAM, 0.82 mmol) in concentrated sulfuric acid (1.5 mL) was added to a solution of 2',7'-difluorofluorescein (commercially from Chemodex Ltd. of Switzerland, 0.3 g, 0.82 mmol) in sulfuric acid (4 mL). After stirring protected from light for 18 h, the reaction mixture was poured over ice (25 mL) to form an orange colored precipitate. The orange precipitate was collected from the melted ice via filtration, washed with water, and dried to yield 0.3 g of product.

Reference： [1]Current Patent Assignee: IDEXX LABORATORIES INC - US2022/82501, 2022, A1

17
C₂₉H₂₇N₅O₅ [ No CAS ]
[ 195136-58-4 ]
C₄₉H₃₅F₂N₅O₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2 mg	Stage #1: C₂₉H₂₇N₅O₅ With 4-dimethylaminopyridine In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2',7'-difluorofluorescein In N,N-dimethyl-formamide at 20℃;	11 Production Example 11 Synthesis of Compound 6 12 mg of the compound 1-2, 16 mg of water-soluble carbodiimide, and 3 mg of dimethylaminopyridine were added to 1 mL of N,N-dimethylformamide, and the mixture was stirred at room temperature for 30 minutes. 10 mg of 2′,7′-difluorofluorescein (manufactured by Thermo Fisher Scientific Inc.) was added to the mixture, and the mixture was stirred overnight at room temperature. After the solvent was distilled off, the mixture was purified by silica gel column chromatography. Thus, 2 mg of a red solid was prepared.

Reference： [1]Current Patent Assignee: CANON INC. - US2022/162226, 2022, A1 Location in patent: Paragraph 0074

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Ghs Precautionary Statements

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P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
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P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
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Code	Phrase
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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. 195136-58-4 ] {[proInfo.proName]}

Quality Control of [ 195136-58-4 ]

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[ 195136-58-4 ] Synthesis Path-Downstream 1~17

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Fluorinated Building Blocks

Alcohols

Esters

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[ 195136-58-4 ]

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[ 195136-58-4 ]