[ CAS No. 551-93-9 ] {[proInfo.proName]}

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Quality Control of [ 551-93-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 551-93-9 ]

SDS Specification

Alternatived Products of [ 551-93-9 ]

Product Details of [ 551-93-9 ]

CAS No. :	551-93-9	MDL No. :	MFCD00007717
Formula :	C₈H₉NO	Boiling Point :	-
Linear Structure Formula :	CH₃C(O)C₆H₄(NH₂)	InChI Key :	GTDQGKWDWVUKTI-UHFFFAOYSA-N
M.W :	135.16	Pubchem ID :	11086
Synonyms :		Chemical Name :	1-(2-Aminophenyl)ethanone

Calculated chemistry of [ 551-93-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	41.04
TPSA :	43.09 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.97 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.46
Log Po/w (XLOGP3) :	1.63
Log Po/w (WLOGP) :	1.48
Log Po/w (MLOGP) :	1.12
Log Po/w (SILICOS-IT) :	1.44
Consensus Log Po/w :	1.43

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.08
Solubility :	1.12 mg/ml ; 0.00826 mol/l
Class :	Soluble
Log S (Ali) :	-2.15
Solubility :	0.962 mg/ml ; 0.00712 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.34
Solubility :	0.615 mg/ml ; 0.00455 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 551-93-9 ]

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

Application In Synthesis of [ 551-93-9 ]

* 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 [ 551-93-9 ]
Downstream synthetic route of [ 551-93-9 ]

[ 551-93-9 ] Synthesis Path-Upstream 1~3

1
[ 551-93-9 ]
[ 15873-56-0 ]
[ 6220-93-5 ]

Reference： [1] Monatshefte fuer Chemie, 1949, vol. 80, p. 607,615

2
[ 551-93-9 ]
[ 6141-14-6 ]

Reference： [1] Chemical Communications, 2014, vol. 50, # 33, p. 4302 - 4304

3
[ 551-93-9 ]
[ 107-14-2 ]
[ 109113-72-6 ]

Reference： [1] Molecules, 2016, vol. 21, # 8,
[2] MedChemComm, 2013, vol. 5, # 11, p. 1700 - 1707

[ 551-93-9 ] Synthesis Path-Downstream 1~10

1
[ 551-93-9 ]
[ 100-52-7 ]
[ 16619-14-0 ]
[ 78396-00-6 ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 3396 - 3397

2
[ 551-93-9 ]
[ 16619-14-0 ]

Reference： [1]Synlett,2006,p. 2791 - 2794
[2]Journal of Medicinal Chemistry,1998,vol. 41,p. 1155 - 1162
[3]South African Journal of Chemistry,1994,vol. 47,p. 21 - 25
[4]Journal of Chemical Research, Miniprint,1994,p. 367 - 382
[5]Synthetic Communications,1987,vol. 17,p. 1235 - 1246
[6]Journal of Organic Chemistry,1990,vol. 55,p. 1757 - 1761
[7]Journal of Organic Chemistry,1990,vol. 55,p. 1757 - 1761
[8]Archiv der Pharmazie,2013,vol. 346,p. 7 - 16
[9]Letters in drug design and discovery,2013,vol. 10,p. 327 - 334
[10]Organic Letters,2015,vol. 17,p. 3202 - 3205
[11]Patent: CN108558756,2018,A

3
[ 1189-71-5 ]
[ 551-93-9 ]
[ 1668-54-8 ]
1-(2-methylcarbonylphenylsulfamoyl)-3-(4-methyl-6-methoxy-1,3,5-triazin-2-yl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane;	EXAMPLE I Preparation of: 1-(2-methylcarbonylphenylsulfamoyl)-3-(4-methyl-6-methoxy-1,3,5-triazin-2-yl)urea To a stirred solution of 0.01 mole of chlorosulfonyl isocyanate in methylene chloride maintained at 0°-5° C. via an ice bath was added 1.4 grams (0.01 mole) of <strong>[1668-54-8]2-amino-4-methyl-6-methoxy-1,3,5-triazine</strong>. After two hours reaction time, a methylene chloride solution containing 1.35 grams (0.01 mole) of o-amino acetophenone and 1.0 gram (0.01 mole) of triethylamine is added dropwise. The reaction mixture was stirred rapidly while in the ice bath and was then removed and allowed to warm to room temperature. After standing overnight, the reaction mixture was poured into aqueous sodium carbonate. The aqueous layer was washed once with chloroform and filtered. Acidification with dilute aqueous hydrochloric acid resulted in a white precipitate which after suction filtration and vacuum drying afforded 2.4 grams of material confirmed by NMR analysis as the desired product.
	With triethylamine; In dichloromethane;	Example I Preparation of: 1-(2-methylcarbonylphenylsulfamoyl)-3-(4-methyl-6-methoxy-1,3,5-triazin-2-yl)urea To a stirred solution of 0.01 mole of chlorosulfonyl isocyanate in methylene chloride maintained at 0-5°C. via an ice bath was added 1.4 grams (0.01 mole) of <strong>[1668-54-8]2-amino-4-methyl-6-methoxy-1,3,5-triazine</strong>. After two hours reaction time, a methylene chloride solution containing 1.35 grams (0.01 mole) of o -amino acetophenone and 1.0 gram (0.01 mole) of triethylamine is added dropwise. The reaction mixture was stirred rapidly while in the ice bath and was then removed and allowed to warm to room temperature. After standing overnight, the reaction mixture was poured into aqueous sodium carbonate. The aqueous layer was washed once with chloroform and filtered. Acidification with dilute aqueous hydrochloric acid resulted in a white precipitate which after suction filtration and vacuum drying afforded 2.4 grams of material confirmed by NMR analysis as the desired product.

Reference： [1]Patent: US4622065,1986,A
[2]Patent: EP264467,1988,A1

4
[ 551-93-9 ]
[ 100-52-7 ]
[ 16619-14-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	With C22H48N4O12S4(4+)*4HO4S(1-); In ethanol; water; at 20℃; for 2.1h;Irradiation; Reflux;	1 mmol of benzaldehyde,1 mmol of o-aminoacetophenone and 0.10 mmol of high acidity ionic liquid were separately added to a 50 ml single-necked flask with a condenser tube containing 8 ml of a 94% aqueous ethanol solution and stirred at room temperature.Heating and refluxing, ultrasonic irradiation under the reaction 2.1h, TLC (thin plate chromatography) detection, the raw material disappeared, the end of the reaction to room temperature precipitation of a large number of solid, Into the ice water bath to continue to cool out the solid, the amount of solid is no longer increased when the crushing of the solid, standing, suction, Washed with ethanol (3 ml x 3) and dried in vacuo at 75 C to give 2-phenyl-2,3-dihydro-4 (1H) -quinolinone, The purity was 99.1% and the yield was 92%. The filtrate is directly added with benzaldehyde and o-aminoacetophenone reuse.
88%	With silver trifluoromethanesulfonate; In methanol; for 12h;Reflux; Inert atmosphere;	General procedure: AgOTf (26 mg, 10 mol%) was added to a solution of an o-aminoacetophenone (1.0 mmol) and an aryl aldehyde (1.2 mmol) in MeOH (5mL) at r.t. The reaction mixture was stirred under reflux for 12-24 h. After the reaction was complete, as indicated by TLC, the excess solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (hexanes-EtOAc, 20:1) to yield the desired product.
	With L-proline; In methanol; for 48h;	General procedure: To a solution of L-Proline (0.44 mmol) in methanol (5 mL) was added 2-aminoacetophenone (1.4 mmol) and aldehyde (1.4 mmol) and the mixture was stirred for 48 h. The mixture was treated with 5 mL of saturated ammonium chloride solution and extracted with dichloromethane (3 x 10 mL). The combined organic layer was dried over anhydrous MgSO4, filtered and concentrated. The crude product was purified by column chromatography.

Reference： [1]Patent: CN107162970,2017,A .Location in patent: Paragraph 0041; 0042; 0043
[2]Synthesis,2015,vol. 47,p. 3881 - 3890
[3]Applied Organometallic Chemistry,2019,vol. 33
[4]Synthetic Communications,2010,vol. 40,p. 1391 - 1398
[5]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 645 - 648
[6]Tetrahedron Letters,2012,vol. 53,p. 4059 - 4061
[7]Tetrahedron Letters,2016,vol. 57,p. 5442 - 5445

5
[ 36062-04-1 ]
[ 551-93-9 ]
[ 1408335-41-0 ]

Yield	Reaction Conditions	Operation in experiment
84%	With trifluoroacetic acid; at 100℃; for 0.666667h;	2-Aminoacetophenone (0.675 g, 5 mmol) was taken in a roundbottomed flask along with THC (2.23 g, 6 mmol). To this was added TFA (2?3 mL) and the mixture stirred at 100 C for 40 min. The progress of the reaction was monitored by TLC. Also, the formation of a solid mass was noticed towards completion of the reaction. It was then neutralised with saturated NaHCO3 solution (100 mL). The solid that separated was filtered, washed with water and dried. The resultant crude material was then triturated using ethyl acetate and petroleum ether. The material at this stage was dried in a desiccator over fused CaCl2 for 12 h. Yield: 1.98 g, 84percent. Light yellow solid; m. p. 112?115 C; 1H NMR: d 8.17 (d, J = 8.3 Hz, 1H, H-8), 7.98 (d, J = 8.3 Hz, 1H, H-5), 7.7 (ddd, J1 = 8.6 Hz, J2 = 6.8 Hz, J3 = 1.2 Hz, 1H, H-7), 7.6 (ddd, J1 = 8.3 Hz, J2 = 6.9 Hz, J3 = 1.1 Hz, 1H, H-6), 6.84 (d, J = 8 Hz, 1H, H-26), 6.81 (d, J = 8 Hz, 1H, H-19), 6.75 (d, J = 1.4 Hz, 1H, H-29), 6.73 (d, J = 1.9 Hz, 1H, H-16), 6.70 (dd,J1 = 7.9 Hz, J2 = 1.9 Hz, 1H, H-25), 6.63 (dd, J1 = 8 Hz, J2 = 1.8 Hz, 1H, H-20), 5.79 (br, 2H, Hydroxyls at C-27 & C-18), 3.82 (s, 3H, H-30), 3.78 (s, 3H, H-21), 3.04?3.08 (m, 4H, H-23 & H-14), 3.0?3.04(m, 4H, H-13 & H-22), 2.48 (s, 3H, H-11); 13C NMR: d 207.27(C-12),155.40 (C-2), 146.29 (C-27), 146.20 (C-18), 146.09 (C-10), 143.92(C-28), 143.69 (C-17), 139.87 (C-4), 135.05 (C-3), 133.02 (C-24),131.89 (C-15), 129.89 (C-7), 128.53 (C-8), 126.45 (C-6), 125.82 (C-9), 123.36 (C-5), 120.68 (C-25), 120.66 (C-20), 114.25 (C-26),114.04 (C-19), 111.06 (C-16 & C-29), 55.56 (C-30), 55.50 (C-21),47.16 (C-13), 38.61 (C-14), 35.10 (C-23), 28.69 (C-22), 15.04 (C-11); mass: calculated 471.2046; found; [M+ + 1] = 472.8925.

Reference： [1]Food Chemistry,2013,vol. 136,p. 650 - 658

6
[ 551-93-9 ]
[ 853029-57-9 ]

Reference： [1]MedChemComm,2013,vol. 5,p. 1700 - 1707
[2]Molecules,2016,vol. 21
[3]Patent: CN110590780,2019,A
[4]Patent: CN110590780,2019,A
[5]Patent: CN110590780,2019,A
[6]Patent: WO2020/31040,2020,A1

7
[ 551-93-9 ]
[ 100-52-7 ]
[ 16619-14-0 ]
1-(2-aminophenyl)-3-hydroxy-3-phenylpropan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8%; 13%	With silver trifluoromethanesulfonate; In methanol; for 3h;Reflux; Inert atmosphere;	AgOTf (26 mg, 10 molpercent) was added to a solution of o-aminoacetophenone(1a; 135 mg, 1.0 mmol) and benzaldehyde (2a; 127 mg, 1.2 mmol) in MeOH (5 mL) at r.t. The reaction mixture was stirred under reflux for 3 h only. The excess solvent was removed under reduced pressure and the residue was purified by silica gel gradient column chromatography (hexanes?EtOAc, 20:1?5:1) to yield 1a (104 mg, 77percent, recovered), 3a (17 mg, 8percent), and 4a (31 mg, 13percent).

Reference： [1]Synthesis,2015,vol. 47,p. 3881 - 3890

8
[ 551-93-9 ]
[ 100-52-7 ]
[ 16619-14-0 ]
C₁₅H₁₃NO [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,2016,vol. 52,p. 99 - 103
Khim. Geterotsikl. Soedin.,2016,vol. 52,p. 99 - 103,5

9
[ 62162-97-4 ]
[ 551-93-9 ]
C₂₂H₁₇NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28.2 g	With tri-tert-butyl phosphine; potassium acetate; potassium carbonate; In toluene; for 24h;Reflux;	The reaction flask to <strong>[62162-97-4]2-bromo-phenanthrene</strong> 30.0g (116.7mmol), compound [219-1] 18.9g (140.0 mmol), palladium (II) acetate, 524mg (2.33 mmol), potassium carbonate and 24.2g (175.1 mmol), toluene 500mL, was added to tert-butylphosphine tree 2.2mL (4.66 mmol) was stirred under reflux for 24 hours. After completion of the reaction was poured into a saturated ammonium aqueous solution to the reaction solution and extracted with ethyl acetate. After separation the organic layer was filtered then dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure and, after purification by column chromatography to prepare an intermediate compound of a yellow solid [219-2] 28.2g (78wtpercent).

Reference： [1]Patent: KR2016/55375,2016,A .Location in patent: Paragraph 0148-0152

10
[ 16619-14-0 ]
[ 551-93-9 ]
7-methyl-6-phenyl-5,6-dihydrodibenzo[b,h][1,6]naphthyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In ethyl acetate; at 60℃; for 24h;Inert atmosphere;	General procedure: To a mixture of 2-aminobenzophenone (1.1mmol, 0.22g) and 2-phenyl-2,3-dihydroquinolin-4-one (1.1mmol, 0.25g) was added T3P? (2.2mmol, 0.70g) and the reaction mixture stirred at 60°C for 24h. Water (100mL) was added to dissolve T3P? and the mixture extracted with dichloromethane (3×60mL). The combined organic extracts were washed with brine, dried over Na2SO4 and the solvent removed under reduced pressure. The crude product was recrystallized from methanol to give product 6a as yellow needles (57percent).

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 5442 - 5445

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Technical Information

? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Clemmensen Reduction ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? Grignard Reaction ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? Mannich Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reformatsky Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Specialized Acylation Reagents-Vilsmeier Reagent ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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[ 551-93-9 ]

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[ 334618-23-4 ]

(R)-Piperidin-3-amine dihydrochloride

[ 109113-72-6 ]

2-(Chloromethyl)-4-methylquinazoline

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P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
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. 551-93-9 ] {[proInfo.proName]}

Quality Control of [ 551-93-9 ]

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[ 551-93-9 ] Synthesis Path-Upstream 1~3

[ 551-93-9 ] Synthesis Path-Downstream 1~10

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Aryls

Ketones

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[ 551-93-9 ]

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