[ CAS No. 52568-28-2 ] {[proInfo.proName]}

Name: 52568-28-2|2-(Pyridin-2-yl)propan-2-amine|95%
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3d Animation Molecule Structure of 52568-28-2

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Quality Control of [ 52568-28-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 52568-28-2 ]

SDS Specification

Alternatived Products of [ 52568-28-2 ]

Product Details of [ 52568-28-2 ]

CAS No. :	52568-28-2	MDL No. :	MFCD08729302
Formula :	C₈H₁₂N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DQSQBZXDMHDHEO-UHFFFAOYSA-N
M.W :	136.19	Pubchem ID :	22736922
Synonyms :

Calculated chemistry of [ 52568-28-2 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.38
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	41.41
TPSA :	38.91 Å²

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) :	-6.89 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.69
Log Po/w (XLOGP3) :	0.34
Log Po/w (WLOGP) :	1.17
Log Po/w (MLOGP) :	0.55
Log Po/w (SILICOS-IT) :	1.26
Consensus Log Po/w :	1.0

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.28
Solubility :	7.2 mg/ml ; 0.0529 mol/l
Class :	Very soluble
Log S (Ali) :	-0.72
Solubility :	25.9 mg/ml ; 0.19 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.46
Solubility :	0.474 mg/ml ; 0.00348 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.3

Safety of [ 52568-28-2 ]

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 [ 52568-28-2 ]

* 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 [ 52568-28-2 ]
Downstream synthetic route of [ 52568-28-2 ]

[ 52568-28-2 ] Synthesis Path-Upstream 1~5

1
[ 100-70-9 ]
[ 917-54-4 ]
[ 52568-28-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: With cerium(III) chloride In tetrahydrofuran; diethyl ether at -76 - -60℃; Stage #2: at -76 - 15℃;	Add THF (240 mL) to anhydrous cerium (III) chloride (35 g, 144 mmol) and stir the slurry under nitrogen for 30 minutes. Cool the mixture to -76⁰C in a dry-ice acetone bath. Add a 1.6 M solution of methyl lithium in Et₂O (90 mL, 144 mmol) dropwise maintaining the internal reaction temperature below -60⁰C. Stir for 30 minutes after the addition is complete, cool the reaction to -76⁰C, then add 2-cyanopyridine (5 g, 48 mmol) as a solution in THF (20 mL) controlling the addition to keep the reaction below -60⁰C. Stir the mixture in the dry-ice bath for 15 minutes, then remove the bath and allow the reaction to warm to 15 ⁰C. Cool the reaction in the dry-ice bath then add ammonium hydroxide (90 mL) with stirring. Allow the reaction to warm to room temperature with stirring overnight. Decant the solution from the mixture and wash the solids well with THF. Combine the filtrate and washes, then evaporate to give 1 -methyl- l-pyridin-2-yl- ethylamine in quantitative mass balance. ¹H NMR (400 MHz, CDCl₃): δ 8.52 (d, J= 4.0 Hz, IH), 7.60 (td, J= 7.7, 1.6 Hz, IH), 7.42 (d, J= 7.9 Hz, IH), 7.15-7.08 (m, IH), 1.47 (s, 6H).
73%	Stage #1: With cerium(III) chloride In tetrahydrofuran; diethyl ether at -70℃; for 0.5 h; Stage #2: at -60 - 23℃; for 2.5 h;	Example 121 5-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-(at))thiophene-2-sulfonic acid (1 -methyl-1 - pyridin-2-yl) ethylamide hydrochloride Step 1: 1-methyl-1-pyridm-2-yl) ethylamine: Anhydrous cerium chloride (5.10g, 20.69 mmol) is placed in a flask and vacuum dried for 15 min while being heated with a heat gun, then it is cooled to 0°C and tetrahydrofuran (45 mL) is added. After stirring at room temperature for 2 hr, the mixture is cooled to -70°C and treated with 2.0 M methyl lithium in diethyl ether (10.5 mL, 21 mmol). After stirring for an additional period of 0.5 hrs, 2-cyanopyridine (720 mg, 6.91 mmol) in tetrahydrofuran (1 mL) is added. The reaction temperature is kept below-60°C for 0.5 hr, then the temperature is raised to 23°C while stirring for 2 hr. The reaction is quenched with isopropanol (3 mL), filtered through a pad of Celite that is washed thoroughly with dichloromethane. The combined filtrate and wash is concentrated and the residue is purified by flash chromatography on an ISCO Redisep 35 g cartridge eluting with dichloromethane-10percent methanol to afford 1-methyl-1-pyridin-2-yl)ethylamine (688 mg, 73percent yield) as an oil that solidified on standing to yellow solid. ¹H NMR (No., ppm) : 1.6 (6H, s), 7.42 (1H), 7.64 (1H), 7.90 (1H), 8.2 (2H, br s), 8.65 (1H).

Reference： [1] Patent: WO2009/131814, 2009, A2, . Location in patent: Page/Page column 43
[2] Journal of the American Chemical Society, 2014, vol. 136, # 33, p. 11574 - 11577
[3] Angewandte Chemie - International Edition, 2013, vol. 52, # 51, p. 13588 - 13592[4] Angew. Chem., 2013, vol. 125, # 51, p. 13833 - 13837,5
[5] Patent: WO2005/97750, 2005, A1, . Location in patent: Page/Page column 147-148
[6] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3730 - 3742
[7] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 4, p. 373 - 377

2
[ 100-70-9 ]
[ 75-16-1 ]
[ 52568-28-2 ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: at 0 - 100℃; Stage #2: With hydrogenchloride; water In toluene at 0℃; Stage #3: With sodium hydroxide In water	Synthesis of 1-methyl-1-pyridin-2-yl-ethylamine (217), Scheme 8; To a solution of 2-cyanopyridine (33.0 g, 0.32 mol) in 800 mL of toluene was added MeMgBr (566 mL, 2.5 equiv) slowly at 0° C. The mixture was heated at 100° C. overnight, and then quenched with 2 N HCl in an ice bath. The aqueous layer was collected and basified with 4 N NaOH, and then extracted with ether (500 mL.x.3). The combined organic layer was dried and concentrated to give the title compound (35.0 g, 81percent).

Reference： [1] European Journal of Organic Chemistry, 2016, vol. 2016, # 1, p. 139 - 149
[2] Patent: US2008/207573, 2008, A1, . Location in patent: Page/Page column 80; 87
[3] Chemical Communications, 2014, vol. 50, # 61, p. 8353 - 8355
[4] Chemistry--A European Journal, 2015, vol. 21, # 1, p. 205 - 209
[5] Chemical Communications, 2015, vol. 51, # 19, p. 4069 - 4072
[6] Chemical Communications, 2016, vol. 52, # 27, p. 4934 - 4937
[7] Organic Letters, 2014, vol. 16, # 15, p. 3904 - 3907
[8] Chemical Communications, 2015, vol. 51, # 24, p. 5093 - 5096
[9] Journal of the American Chemical Society, 2015, vol. 137, # 25, p. 8219 - 8226
[10] Organic Letters, 2014, vol. 16, # 21, p. 5644 - 5647
[11] Advanced Synthesis and Catalysis, 2017, vol. 359, # 23, p. 4117 - 4121
[12] Advanced Synthesis and Catalysis, 2017, vol. 359, # 13, p. 2241 - 2246

3
[ 100-70-9 ]
[ 52568-28-2 ]

Reference： [1] Patent: WO2008/4698, 2008, A2, . Location in patent: Page/Page column 129-130

4
[ 1192356-19-6 ]
[ 52568-28-2 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 4, p. 373 - 377

5
[ 100-70-9 ]
[ 917-64-6 ]
[ 52568-28-2 ]

Reference： [1] European Journal of Inorganic Chemistry, 2016, vol. 2016, # 23, p. 3728 - 3743

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P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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P233	Keep container tightly closed.
P234	Keep only in original container.
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P240	Ground/bond container and receiving equipment.
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P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
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P250	Do not subject to grinding/shock/friction.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
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P270	Do not eat, drink or smoke when using this product.
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P313	Get medical advice/attention.
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P320
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P321
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P378
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Yield	Reaction Conditions	Operation in experiment
	With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 16h;	Step 4: Preparation of N-[1-methyl-1-(2-pyridyl)ethyl]-2-methylsulfanyl-2-[(3-vinyl-6-quinolyl)oxy]acetamide (compound No. 133 Table 51) To a solution of 2-methylsulfanyl-2-[(3-vinyl-6-quinolyl)oxy]acetic acid (0.41 mmol, 114 mg) in DMF (2 mL) was sequentially added Et3N (0.52 mmol, 0.072 mL), HOAT (0.52 mmol, 70 mg), 2-(4-methyl-2-pyridyl)propan-2-amine (0.41 mmol, 56 mg) and EDCI (0.52 mmol, 99 mg). The reaction was then stirred for 16 h at RT. The reaction mixture was taken up in EtOAc and washed three times with brine, dried over MgSO4, filtered and evaporated. The crude product was purified by column chromatography over SiO2 (EtOAc/Heptane 1:1) to yield N-[1-methyl-1-(2-pyridyl)ethyl]-2-methylsulfanyl-2-[(3-vinyl-6-quinolyl)oxy]acetamide as an off-white solid. UPLC: rt=0.79 min, m/z=394 ([MH]+); M.p.=95-97 C.; 1H NMR (CDCl3) delta ppm: 9.21 (1H, s), 8.90 (1H, d), 8.53 (1H, d), 8.06 (1H, d), 8.00 (1H, s), 7.72 (1H, t), 7.52 (1H, dd), 7.40 (1H, d), 7.29 (1H, d), 7.23 (1H, t), 6.85 (1H, dd), 5.99 (1H, d), 5.70 (1H, s), 5.49 (1H, d), 2.22 (3H, s), 1.84 (3H, s), 1.79 (3H, s).
	With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 16h;	To a solution of 2-methylsulfanyl-2-[(3-vinyl-6-quinolyl)oxy]acetic acid (0.41 mmol, 1 14 mg) in DMF (2 mL) was sequentially added Et3N (0.52 mmol, 0.072 mL), HOAT (0.52 mmol, 70 mg), 2-(4-methyl-2-pyridyl)propan-2-amine (0.41 mmol, 56 mg) and EDCI (0.52 mmol, 99 mg). The reaction was then stirred for 16 h at RT. The reaction mixture was taken up in EtOAc and washed three times with brine, dried over MgS04, filtered and evaporated. The crude product was purified by column chromatography over Si02 (EtOAc/Heptane 1 :1) to yield A/-[1-methyl-1-(2-pyridyl)ethyl]-2-methylsulfanyl-2-[(3-vinyl- 6-quinolyl)oxy]acetamide as an off-white solid.UPLC: rt = 0.79 min, m/z = 394 ([MH]+); M.p. = 95 -97C; 1 H NMR (CDCI3) delta ppm: 9.21 (1 H, s), 8.90 (1 H, d), 8.53 (1 H, d), 8.06 (1 H, d), 8.00 (1 H, s), 7.72 (1 H, t), 7.52 (1 H, dd), 7.40 (1 H, d), 7.29 (1 H, d), 7.23 (1 H, t), 6.85 (1 H, dd), 5.99 (1 H, d), 5.70 (1 H, s), 5.49 (1 H, d), 2.22 (3H, s), 1.84 (3H, s), 1.79 (3H, s).

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. 52568-28-2 ] {[proInfo.proName]}

Quality Control of [ 52568-28-2 ]

Related Doc. of [ 52568-28-2 ]

Product Details of [ 52568-28-2 ]

Calculated chemistry of [ 52568-28-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 52568-28-2 ]

Application In Synthesis of [ 52568-28-2 ]

[ 52568-28-2 ] Synthesis Path-Upstream 1~5

[ 52568-28-2 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 52568-28-2 ]

Amines

Related Parent Nucleus of [ 52568-28-2 ]

Pyridines

Precautionary Statements-General

Prevention

Response

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Physical hazards

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Environmental hazards

Inquiry

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[ 52568-28-2 ]

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[ 52568-28-2 ]