[ CAS No. 83229-23-6 ]

Name: 83229-23-6|8-Chloro-3,4-dihydroquinolin-2(1H)-one|95%
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SKU: A317528
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Quality Control of [ 83229-23-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 83229-23-6 ]

Product Details of [ 83229-23-6 ]

CAS No. :	83229-23-6	MDL No. :	MFCD19276419
Formula :	C₉H₈ClNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JXNDVVMVKPPSCD-UHFFFAOYSA-N
M.W :	181.62	Pubchem ID :	13104914
Synonyms :

Calculated chemistry of [ 83229-23-6 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	51.55
TPSA :	29.1 Å²

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) :	-6.21 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.93
Log Po/w (XLOGP3) :	1.69
Log Po/w (WLOGP) :	1.65
Log Po/w (MLOGP) :	2.02
Log Po/w (SILICOS-IT) :	2.73
Consensus Log Po/w :	2.0

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.4
Solubility :	0.722 mg/ml ; 0.00397 mol/l
Class :	Soluble
Log S (Ali) :	-1.92
Solubility :	2.2 mg/ml ; 0.0121 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.78
Solubility :	0.0299 mg/ml ; 0.000165 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.56

Safety of [ 83229-23-6 ]

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 [ 83229-23-6 ]

* 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 [ 83229-23-6 ]
Downstream synthetic route of [ 83229-23-6 ]

[ 83229-23-6 ] Synthesis Path-Upstream 1~4

1
[ 201230-82-2 ]
[ 104-15-4 ]
[ 83229-23-6 ]

Reference： [1] ACS Catalysis, 2018, vol. 8, # 11, p. 10340 - 10348

2
[ 95-51-2 ]
[ 625-36-5 ]
[ 83229-23-6 ]
[ 21261-72-3 ]

Reference： [1] Patent: US5478842, 1995, A,

3
[ 21261-72-3 ]
[ 83229-23-6 ]

Reference： [1] Chemische Berichte, 1927, vol. 60, p. 861

4
[ 7446-70-0 ]
[ 21261-72-3 ]
[ 83229-23-6 ]

Reference： [1] Chemische Berichte, 1927, vol. 60, p. 860

[ 83229-23-6 ] Synthesis Path-Downstream 1~9

2
[ 21261-72-3 ]
[ 83229-23-6 ]

Reference： [1]Chemische Berichte,1927,vol. 60,p. 861

3
[ 83229-23-6 ]
[ 142944-48-7 ]
8-Chloro-1-{3-[4-(3-chloro-phenyl)-piperazin-1-yl]-propyl}-3,4-dihydro-1H-quinolin-2-one [ No CAS ]

Reference： [1]Pharmazie,1997,vol. 52,p. 423 - 428

4
[ 7446-70-0 ]
[ 21261-72-3 ]
[ 83229-23-6 ]

Reference： [1]Chemische Berichte,1927,vol. 60,p. 860

5
8-chloro-6-mercapto-1,2,3,4-tetrahydroquinolin-2-one [ No CAS ]
[ 95-51-2 ]
[ 625-36-5 ]
[ 83229-23-6 ]
[ 21261-72-3 ]

Yield	Reaction Conditions	Operation in experiment
86%; 90%	In dichloromethane;	The 8-chloro-6-mercapto-1,2,3,4-tetrahydroquinolin-2-one used as a starting material was obtained as follows: A solution of 3-chloropropionyl chloride (19.1 ml) in methylene chloride (80 ml) was added dropwise during 45 minutes to a stirred solution of 2-chloroaniline (43 ml) in methylene chloride (20 ml) which had been cooled to 0 C. The mixture was stirred at 0 C. for 2 hours. Methylene chloride (100 ml) was added and the mixture was washed with water, dried (Na2 SO4) and evaporated. The residue was triturated under hexane. There was thus obtained 3,2'-dichloropropionanilide (39.1 g, 90%), m.p. 79-80 C. The material so obtained was added portionwise to aluminium chloride (71.4 g) and the mixture was stirred and heated to 120 C. When the addition was complete, the mixture was heated to 120 C. for 4 hours. The mixture was cooled to 80 C. and poured onto crushed ice. The resultant mixture was extracted with methylene chloride. The organic solution was washed with a saturated aqueous sodium bicarbonate solution, dried (Na2 SO4) and evaporated. There was thus obtained 8-chloro-1,2,3,4-tetrahydroquinolin-2-one (28.1 g, 86%), m.p. 107-109 C.

Reference： [1]Patent: US5478842,1995,A

6
[ 83229-23-6 ]
8-chloro-6-nitro-3,4-dihydro-2(1H)-quinolinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With nitric acid; In acetic anhydride; acetic acid;	PREPARATION 1 To a solution of <strong>[83229-23-6]8-chloro-3,4-dihydro-2(1H)-quinolinone</strong> (5.08 g) in acetic anhydride (50 ml) was dropwise added a solution of nitric acid (d=1.40, 2.97 g) in acetic acid (20 ml) over the period of 10 minutes with stirring under ice-cooling. The mixture was stirred for 2 hours at ambient temperature and then for 6 hours at 50 C., and was allowed to stand for 60 hours at ambient temperature. The resulting precipitates were collected, washed with acetic anhydride and ethyl acetate successively and dried to give 8-chloro-6-nitro-3,4-dihydro-2(1H)-quinolinone (3.83 g). mp: 208-209 C. IR (Nujol): 3100, 1695, 1685, 1615 cm-1 NMR (DMSO-d6, delta): 2.5-2.8 (2H, m), 3.0-3.3 (2H, m), 8.18 (2H, s), 10.17 (1H, s)

Reference： [1]Patent: US4988698,1991,A

7
[ 83229-23-6 ]
[ 7440-44-0 ]
[ 563-76-8 ]
[ 70386-54-8 ]

Yield	Reaction Conditions	Operation in experiment
	aluminium trichloride; In carbon disulfide; chloroform;	REFERENCE EXAMPLE 11 To a solution of alpha-bromopropionyl bromide (60 g) and aluminum chloride (40 g) in carbon disulfide (100 ml) was added <strong>[83229-23-6]8-chloro-3,4-dihydrocarbostyril</strong> (10 g). After refluxing the mixture for 5 hours, carbon disulfide was evaporated and heated at 70 to 80 C. for 5 hours. The reaction mixture was poured into ice water and allowed to stand overnight. The mixture was extracted with chloroform and the chloroform layer was washed with water, dried and treated with activated carbon followed by evaporating chloroform. The residue was washed with diethyl ether and collected by filtration. The residue gave uniform crude crystals upon TLC. The crystals thus obtained were re-crystallized from methanol to give 12 g of 8-chloro-6-alpha-bromopropionyl-3,4-dihydrocarbostyril. m.p. 180-182 C., pale yellow needles

Reference： [1]Patent: US4414390,1983,A

8
[ 83229-23-6 ]
potassium ferrocyanide [ No CAS ]
8-cyano-3,4-dihydro-1H-quinolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With t-BuBrettPhos; [(2-di-tert-butylphosphino-3,6-dimethoxy-2?,4?,6?-triisopropyl-1,1?-biphenyl)-2-(2?-amino-1,1?-biphenyl)]palladium(II) methanesulfonate; potassium acetate; In 1,4-dioxane; water; at 100.0℃; for 1.5h;Inert atmosphere;	8-Chloro-3,4-dihydro-lH-quinolin-2-one (0.500 g, 2.75 mmol) was dissolved in dioxane (2.5 mL) and water (2.5 mL). Potassium acetate (0.034 g, 0.344 mmol), tBuBrettPhos Pd G3 (0.235 g, 0.275 mmol), tButBrettPhos (0.133 g, 0.275 mmol) and potassium hexacyanoferrate(II) trihydrate (0.507 g, 1.37 mmol) in water (0.5 mL) were added. The reaction miture was degased with N2, and heated to 100C and stirred for 90 min. Water was added and the reaction mixture was extracted with ethyl acetate (3x20 mL). The combined organic layers were washed with brin, dired amd concentrated. The crude mixture was purified by flash chromatography to give 8-cyano-3,4-dihydro-lH-quinolin-2-one (0.317 g, 67%); l NMR (CHLOROFORM-d) delta: 7.81 (br s, IH), 7.45 (d, IH), 7.39 (d, IH), 7.05 (t, IH), 2.99-3.06 (t, 2H), 2.66-2.72 (t, 2H).

Reference： [1]Patent: WO2017/34982,2017,A1 .Location in patent: Paragraph 0164

9
[ 201230-82-2 ]
C₈H₆ClNO₂ [ No CAS ]
[ 104-15-4 ]
[ 83229-23-6 ]
C₁₆H₁₄ClNO₄S [ No CAS ]

Reference： [1]ACS Catalysis,2018,vol. 8,p. 10340 - 10348

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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
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P234	Keep only in original container.
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Response
Code	Phrase
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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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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:
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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.
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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
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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. 83229-23-6 ]

Quality Control of [ 83229-23-6 ]

Related Doc. of [ 83229-23-6 ]

Product Details of [ 83229-23-6 ]

Calculated chemistry of [ 83229-23-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 83229-23-6 ]

Application In Synthesis of [ 83229-23-6 ]

[ 83229-23-6 ] Synthesis Path-Upstream 1~4

[ 83229-23-6 ] Synthesis Path-Downstream 1~9

Related Functional Groups of [ 83229-23-6 ]

Chlorides

Amides

Related Parent Nucleus of [ 83229-23-6 ]

Tetrahydroquinolines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 83229-23-6 ]

Related Parent Nucleus of
[ 83229-23-6 ]