[ CAS No. 2243-47-2 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 2243-47-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 2243-47-2 ]

SDS Specification

Alternatived Products of [ 2243-47-2 ]

Product Details of [ 2243-47-2 ]

CAS No. :	2243-47-2	MDL No. :	MFCD00047846
Formula :	C₁₂H₁₁N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MUNOBADFTHUUFG-UHFFFAOYSA-N
M.W :	169.22	Pubchem ID :	16717
Synonyms :

Calculated chemistry of [ 2243-47-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	0.0
Num. H-bond donors :	1.0
Molar Refractivity :	56.28
TPSA :	26.02 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.27 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.87
Log Po/w (XLOGP3) :	2.9
Log Po/w (WLOGP) :	2.94
Log Po/w (MLOGP) :	3.07
Log Po/w (SILICOS-IT) :	2.85
Consensus Log Po/w :	2.73

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.33
Solubility :	0.0786 mg/ml ; 0.000464 mol/l
Class :	Soluble
Log S (Ali) :	-3.11
Solubility :	0.132 mg/ml ; 0.000782 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.55
Solubility :	0.00479 mg/ml ; 0.0000283 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.24

Safety of [ 2243-47-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 2243-47-2 ]

* 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 [ 2243-47-2 ]
Downstream synthetic route of [ 2243-47-2 ]

[ 2243-47-2 ] Synthesis Path-Upstream 1~1

1
[ 2243-47-2 ]
[ 109221-88-7 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 13, p. 1479 - 1482

[ 2243-47-2 ] Synthesis Path-Downstream 1~12

1
[ 2113-58-8 ]
[ 2243-47-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogen;palladium 10% on activated carbon; In ethanol; for 3h;	Palladium on carbon (10%, 0.70 g, 0.658 mmol) was added to a Parr hydrogenator bottle. The bottle was purged with nitrogen. Next, 3- nitro-l,l'-biphenyl (10 g, 50.2 mmol) and 190 mL ethanol were added to the bottle. The material was hydrogenated on a Parr hydrogenator. After 3 h, the reaction mixture was filtered through Celite and the Celite washed with dichloromethane. The filtrate was evaporated, obtained a brown oil, 8.69 g, assume quantitative yield (8.49 g).
99.7%		Another batch of reaction was effected on the same scale except that 254 g (1.28 mol) of <strong>[2113-58-8]m-nitrobiphenyl</strong> was used, obtaining 215 g of m-aminobiphenyl (yield 99.7%).
94%	palladium; In ethyl acetate;	a) 3-phenylaniline To a stirring solution of <strong>[2113-58-8]3-nitrobiphenyl</strong> (1.2 g, 6.0 mmol) in ethyl acetate (25 mL) was added 10% Palladium on carbon (500 mg, 40% w/w). After stirring under a balloon of hydrogen for 24 h, the mixture was filtered through Celite and concentrated to yield the title compound as a white solid (0.956 g, 94%). MS (ESI): 170.0 (M+H)+.

16 g (95%)	palladium-carbon; In methanol; chloroform;	Example 1 Synthesis of 3-aminobiphenyl (1): The following compound is prepared: STR26 A mixture of <strong>[2113-58-8]3-nitrobiphenyl</strong> (20 g, 100 mmol) and 10% Pd/C (2 g) in MeOH/CHCl3 (300 mL, 1:1) is hydrogenated at 40 psi for 4 hours. The mixture is suction filtered through a layer of diatomaceous earth and washed with MeOH. The filtrate is evaporated to dryness and the solid is further dried under vacuum to give 16 g (95%) of 3-aminobiphenyl.
		(a) In a manner similar to that of Example 7(b), <strong>[2113-58-8]3-nitrobiphenyl</strong> (2.48 g) gives 1.77 g of 3-aminobiphenyl, mp 27.5-28.5 C.
	With hydrogen;palladium 10% on activated carbon; In methanol;	Example 11; 3-aminobiphenyl: <strong>[2113-58-8]3-nitrobiphenyl</strong> (500 mg, 2.5 mmol) and 10% palladium on carbon (267 mg, 2.5 mmol) were dissolved in methanol (1 mL) and purged with nitrogen and placed under an atmosphere of hydrogen overnight. The reaction mixture was filtered and evaporated to yield 326 mg of the desired amine, which was used directly in Example 12.

Reference： [1]Patent: WO2012/121936,2012,A2 .Location in patent: Page/Page column 77
[2]Journal of Medicinal Chemistry,2002,vol. 45,p. 2260 - 2276
[3]Patent: EP666298,1995,A2
[4]Patent: US2002/49316,2002,A1
[5]RSC Advances,2014,vol. 4,p. 33599 - 33606
[6]Catalysis science and technology,2018,vol. 8,p. 1454 - 1467
[7]Journal of Organic Chemistry,2014,vol. 79,p. 9433 - 9439
[8]Catalysis Letters,2014,vol. 144,p. 1258 - 1267
[9]New Journal of Chemistry,2018,vol. 42,p. 1373 - 1378
[10]Journal of the Chemical Society,1958,p. 1184,1187
[11]Chemische Berichte,1903,vol. 36,p. 4083
[12]Chemische Berichte,1904,vol. 37,p. 882
[13]Journal of the Chemical Society,1927,p. 3006
[14]Journal of the American Chemical Society,1954,vol. 76,p. 2997
[15]Bulletin of the Chemical Society of Japan,1975,vol. 48,p. 1868 - 1874
[16]Recueil des Travaux Chimiques des Pays-Bas,1963,vol. 82,p. 5 - 16
[17]Arzneimittel-Forschung/Drug Research,1972,vol. 22,p. 1399 - 1404
[18]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1479 - 1482
[19]Patent: US6004536,1999,A
[20]Patent: US6211220,2001,B1
[21]Patent: WO2008/13791,2008,A2 .Location in patent: Page/Page column 32
[22]Journal of Medicinal Chemistry,2009,vol. 52,p. 3703 - 3715
[23]ChemPlusChem,2020,vol. 85,p. 247 - 253
[24]Journal of Agricultural and Food Chemistry,2021,vol. 69,p. 12039 - 12047

2
[ 2243-47-2 ]
[ 109221-88-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1479 - 1482

3
[ 2243-47-2 ]
[ 53592-10-2 ]

Reference： [1]Journal of the Chemical Society,1927,p. 3006

4
Pd-Cl [ No CAS ]
[ 2113-58-8 ]
[ 2243-47-2 ]

Yield	Reaction Conditions	Operation in experiment
99.9%	In ethanol;	Example 1 A 2-l atmospheric hydrogenation reactor was charged with 250 g (1.26 mol) of <strong>[2113-58-8]m-nitrobiphenyl</strong>, 12.5 g of 5% Pd-Cl, and 1250 ml of ethanol. A theoretical amount of hydrogen gas was absorbed at room temperature. The catalyst was removed by filtration and the filtrate was distilled of the solvent, obtaining 212 g of m-aminobiphenyl (yield 99.9%).

Reference： [1]Patent: EP666298,1995,A2

5
[ 1392620-48-2 ]
[ 2113-58-8 ]
[ 2243-47-2 ]

Yield	Reaction Conditions	Operation in experiment
35%; 25%	With triethylsilane; palladium dichloride; In tetrahydrofuran; for 96h;Inert atmosphere; Reflux;	General procedure: To a solution of aryl alkyl sulfide (0.23 mmol, 1.0 equiv) and PdCl2 (0.007 mmol, 3 mol %, 1.2 mg) in 2 mL of THF was added triethylsilane (amount indicated in Table 3) under argon atmosphere (color of the reaction mixture turned to black). The resulting mixture was stirred at room temperature (or at the indicated temperature in Table 3). After completion of the reaction, to the reaction mixture was added 4 mL of H2O (gas evolves). The aqueous layer was extracted with CH2Cl2 (4 mL × 2), and the combined organic layer was dried over Na2SO4 and evaporated. The residue was purified by silica gel column chromatography using hexane/ethyl acetate as eluent.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 4313 - 4316

6
[ 2243-47-2 ]
[ 3177-24-0 ]
[ 336191-17-4 ]
[ 1570262-37-1 ]

Yield	Reaction Conditions	Operation in experiment
		Step 1 : tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (69 mg, 0.287 mol) was added to a cooled solution of the <strong>[3177-24-0]2,4-dichloropyrimidine-5-carbonitrile</strong> (50 mg, 0.287 mmol) and Hunig's base (50 uL, 0.287 mmol) in CH2CI2 (1.5 mL) and the reaction mixture was stirred for 3 hours at 0 °C. The solvent was removed under reduced pressure, then the mixture was diluted with CH3CN (2 mL) and the biphenyl-3 -amine (97 mg, 0.575 mol) was added. The mixture was then heated to 80 °C overnight. Upon cooling, the reaction mixture was diluted with ethyl acetate, washed with 0 and then brine and the organic extracts were dried ( a2S04), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate/hexanes) provided a mixture of the two possible isomers which was separated by the reverse phase chromatography to afford tert-butyl 8-[2-(biphenyl-3- ylamino)-5-cyanopyrimidin-4-yl]-2,8-diazaspiro[4.5]decane-2-carboxylate. MS ESI calcd. for C3oH35 602 [M + H]+ 511 , found 51 1.

Reference： [1]Patent: WO2014/31438,2014,A2 .Location in patent: Paragraph 00239

7
[ 2243-47-2 ]
[ 3177-24-0 ]
[ 336191-17-4 ]
[ 1570258-91-1 ]

Reference： [1]Patent: WO2014/31438,2014,A2

8
[ 1171919-75-7 ]
[ 2243-47-2 ]
tert-butyl (3R)-3-[(2-sulfanylacetyl)amino]piperidine-1-carboxylate [ No CAS ]
[ 530-62-1 ]
(R)-tert-butyl 3-(5-([1,1’-biphenyl]-3-yl)-4-oxo-4,5-dihydro-3H-1-thia-3,5,8-triazaacenaphthylene-2-carboxamido)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23.2%		To a 2-5 mL Biotage microwave vial with a stir bar were added 3-aminobiphenyl (370.5 mg, 2.189 mmol), 2-chloro-4- iodonicotinonitrile (578 mg, 2.186 mmol), Pd(OAc)2(9.6 mg, 0.043 mmol), DPEPhos (36.1 mg, 0.0671 mmol), and CS2CO3(988 mg, 3.03 mmol). The vial was sealed and treated with dioxane (4.35 mL), evacuated/flushed with argon 4X, and stirred at 150 C under argon for 30. The reaction was then cooled to room temperature, treated with tert-butyl (3R)-3-[(2- sulfanylacetyl)amino]piperidine-l -carboxylate (Intermediate 22) in dioxane (4.05 mL, 0.65 M, 2.63 mmol) via syringe, evacuated/flushed with argon 4X, and stirred at 150 C for 15 min. The reaction was then cooled to room temperature, treated with solid CDI (1.409 g, 8.689 mmol) in one portion under air, resealed and evacuated/flushed with argon 4X, and stirred at 150 C for 15 min. The reaction was diluted with EtOAc (10 mL), and washed with 0.5 M citric acid/brine (2 x 8 mL) and 2 M K2CO3(1 x 5 mL), dried over anhydrous Na2SC>4, filtered, and concentrated to dryness. The reaction mixture was purified by flash column chromatography to give the title compound as a beige foam (289 mg, 23.2% yield).

Reference： [1]Patent: WO2017/100668,2017,A1 .Location in patent: Page/Page column 475

9
[ 1171919-75-7 ]
[ 2243-47-2 ]
tert-butyl (3R)-3-[(2-sulfanylacetyl)amino]piperidine-1-carboxylate [ No CAS ]
(R)-tert-butyl 3-(5-([1,1’-biphenyl]-3-yl)-4-oxo-4,5-dihydro-3H-1-thia-3,5,8-triazaacenaphthylene-2-carboxamido)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23.2%		To a 2-5 mL Biotage microwave vial with a stir bar were added 3-aminobiphenyl (370.5 mg, 2.189 mmol) , <strong>[1171919-75-7]2-chloro-4-iodonicotinonitrile</strong> (578 mg, 2.186 mmol) , Pd (OAc)2(9.6 mg, 0.043 mmol) , DPEPhos (36.1 mg, 0.0671 mmol) , and Cs2CO3(988 mg, 3.03 mmol) . The vial was sealed and treated with dioxane (4.35 mL) , evacuated/flushed with argon 4X, and stirred at 150 under argon for 30. The reaction was then cooled to room temperature, treated with tert-butyl (3R) -3- [ (2-sulfanylacetyl) amino] piperidine-1-carboxylate (Intermediate 22) in dioxane (4.05 mL, 0.65 M, 2.63 mmol) via syringe, evacuated/flushed with argon 4X, and stirred at 150 for 15 min. The reaction was then cooled to room temperature, treated with solid CDI (1.409 g, 8.689 mmol) in one portion under air, resealed and evacuated/flushed with argon 4X, and stirred at 150 for 15 min. The reaction was diluted with EtOAc (10 mL) , and washed with 0.5 M citric acid/brine (2 x 8 mL) and 2 M K2CO3(1 x 5 mL) , dried over anhydrous Na2SO4, filtered, and concentrated to dryness. The reaction mixture was purified by flash column chromatography to give the title compound as a beige foam (289 mg, 23.2yield) .

Reference： [1]Patent: WO2018/103058,2018,A1 .Location in patent: Page/Page column 475

10
[ 2243-47-2 ]
[ 53554-29-3 ]
ethyl 2-([1,1'-biphenyl]-3-ylamino)-4-hydroxypyrimidine-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87.6%	In ethanol; for 24h;Reflux; Sealed tube;	General procedure: To a Radley reaction carousel tube, add 1 equivalent 1, 1.1 equivalents of the amine, a stir bar, and 5 mL 95% ethanol. Reflux while stirring for 24 hours. After cooling to room temperature the resulting precipitate was collected by vacuum filtration, washing with 10 mL deionized water and 5 mL chloroform.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29

11
[ 26608-06-0 ]
[ 2243-47-2 ]
C₂₃H₂₃F₃O₃S [ No CAS ]
C₄₆H₃₉NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%		Under nitrogen protection, 5-((3r, 5r, 7r) -adamantane-1-yl)-[1,1'-biphenyl] -2-yltrifluoromethanesulfonate 82.287mmol 82.287mmol of 3-aminobiphenyl, 720mL of toluene, 246.86mmol of sodium tert-butoxide, stir and heat to 70 C, slowly add Pd2dba3 0.82287mmol, 1.6457mmol of s-PHOS, after the addition, continue to warm to 105 C and reflux After 6 hours of reaction, the temperature was lowered to 70 C., <strong>[26608-06-0]3-bromodibenzofuran</strong> was added to 80.641 mmol, and the temperature was further increased to 105 C. and refluxed for 4 h. After the reaction was completed, the temperature was lowered, and the organic phase was extracted with water, dried, filtered, and concentrated. After passing through the column with a mixed solvent of dichloromethane and n-heptane, it was recrystallized to LC> 99.95%. Compound 18 was dried. Yield: 53%.

Reference： [1]Patent: CN110240546,2019,A .Location in patent: Paragraph 0107-0110

12
[ 26608-06-0 ]
[ 2243-47-2 ]
1-(4'-bromobiphenyl-4-yl)adamantane [ No CAS ]
C₄₆H₃₉NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%		Under nitrogen protection, 4-bromo-4'-adamantyl biphenyl 82.797mmol, 3-aminobiphenyl 82.797mmol, toluene 608mL, sodium tert-butoxide 248.391mmol were added to the reaction flask, stirred, and heated to 70 C Slowly add Pd2dba30.82797mmol and s-PHOS 1.6560mmol. After the addition, continue to warm to 105 C and reflux for 2h, then lower the temperature to 70 C, add <strong>[26608-06-0]3-bromodibenzofuran</strong> 81.141mmol, continue to raise to 105 C and reflux After 8 hours of reaction, the reaction was completed, the temperature was lowered, and the mixture was extracted with dichloromethane. The organic phase was washed with water, dried, filtered, and concentrated. After passing through the column with a mixed solvent of dichloromethane and n-heptane, it was recrystallized to LC> 99.95%. Dried compound 17. Yield: 65%.

Reference： [1]Patent: CN110240546,2019,A .Location in patent: Paragraph 0103-0106

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Technical Information

? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Friedel-Crafts Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Leuckart-Wallach Reaction ? Mannich Reaction ? Petasis Reaction ? Preparation of Alkylbenzene ? Preparation of Amines ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Specialized Acylation Reagents-Vilsmeier Reagent ? Ugi Reaction ? Vilsmeier-Haack Reaction

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P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
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

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[ CAS No. 2243-47-2 ] {[proInfo.proName]}

Quality Control of [ 2243-47-2 ]

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Product Details of [ 2243-47-2 ]

Calculated chemistry of [ 2243-47-2 ] Expand+

Physicochemical Properties

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Lipophilicity

Druglikeness

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Medicinal Chemistry

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Application In Synthesis of [ 2243-47-2 ]

[ 2243-47-2 ] Synthesis Path-Upstream 1~1

[ 2243-47-2 ] Synthesis Path-Downstream 1~12

Technical Information

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Aryls

Amines

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[ 2243-47-2 ]