[ CAS No. 1109230-25-2 ] {[proInfo.proName]}

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2D 3D

Structure of 1109230-25-2 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 1109230-25-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1109230-25-2 ]

SDS Specification

Alternatived Products of [ 1109230-25-2 ]

Product Details of [ 1109230-25-2 ]

CAS No. :	1109230-25-2	MDL No. :	MFCD11847788
Formula :	C₉H₈BrNO	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	LYXUIQHDUVHEMZ-UHFFFAOYSA-N
M.W :	226.07	Pubchem ID :	21865472
Synonyms :

Calculated chemistry of [ 1109230-25-2 ] Expand+

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 :	53.91
TPSA :	29.1 ?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) :	-6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.85
Log Po/w (XLOGP3) :	1.92
Log Po/w (WLOGP) :	1.35
Log Po/w (MLOGP) :	2.17
Log Po/w (SILICOS-IT) :	2.76
Consensus Log Po/w :	2.01

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.82
Solubility :	0.341 mg/ml ; 0.00151 mol/l
Class :	Soluble
Log S (Ali) :	-2.15
Solubility :	1.58 mg/ml ; 0.007 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.03
Solubility :	0.0212 mg/ml ; 0.000094 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.67

Safety of [ 1109230-25-2 ]

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

Application In Synthesis of [ 1109230-25-2 ]

* 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 [ 1109230-25-2 ]
Downstream synthetic route of [ 1109230-25-2 ]

[ 1109230-25-2 ] Synthesis Path-Upstream 1~1

1
[ 1109230-25-2 ]
[ 190777-77-6 ]

Yield	Reaction Conditions	Operation in experiment
35%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane at 100℃; for 24 h;	[0121] A mixture of 5-bromo-3,4-dihydro-2H-isoquinolin-l-one (4.3 g, 18.9 mmol) and 2,3-dicyano-5,6-dichloro-l,4-benzoquinone (8.6 g, 37.9 mmol) in 1,4-dioxane (76 mL) was stirred at 100 °C for 24 h. The reaction mixture was evaporated and the residue was taken up in ethyl acetate (500 mL) and washed with 10percent aqueous sodium hydroxide (2 x 500 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (4 x 300 mL). The combined organic layers were dried over sodium sulfate, evaporated and purified by flash chromatography eluting with dichloromethane: methanol (99: 1 -^96:4) to give the title compound (1.49 g, 6.65 mmol, 35percent) as a yellow solid. LCMS: 94percent, Rt 1.243, ESMS m/z 224 (M+H)⁺.
35%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane at 100℃; for 24 h;	-1. 5-Bromo-2H-isoquinolin-l-one. [00114] A mixture of 5-bromo-3,4-dihydro-2H-isoquinolin-l -one (Preparation 3-1, 4.3 g, 18.9 mmol) and 2,3-dicyano-5,6-dichloro-l,4-benzoquinone (8.6 g, 37.9 mmol) in 1,4-dioxane (76 mL) was stirred at 100 °C for 24 h. The reaction mixture was evaporated and the residue was taken up in ethyl acetate (500 mL) and washed with 10percent aqueous sodium hydroxide (2 x 500 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (4 x 300 mL). The combined organic layers were dried over sodium sulfate, evaporated and purified by flash chromatography eluting with dichloromethane:methanol (99: 1 -^96:4) to give the title compound (1.49 g, 6.65 mmol, 35percent) as a yellow solid. LCMS: 94percent, Rt 1.243, ESMS m/z 224 (M+H)⁺.
35%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane at 100℃; for 24 h;	[001081 A mixture of 5-bromo-3,4-dihydro-2H-isoquinolin-1-one (Preparation 3-1, 4.3 g, 18.9 mmol) and 2,3-dicyano-5,6-dichloro-1,4-benzoquinone (8.6 g, 37.9 mmol) in 1,4-dioxane (76 mL) was stirred at 100 °C for 24 h. The reaction mixture was evaporated and the residue was taken up in ethyl acetate (500 mL) and washed with 10percent aqueous sodium hydroxide (2 x 500 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (4 x 300 mL). The combined organic layers were dried over sodium sulfate, evaporated and purified by flash chromatography eluting with dichloromethane:methanol (99:1 -96:4) to give the title compound (1.49 g, 6.65 mmol, 35percent) as a yellow solid. LCMS: 94percent, Rt 1.243, ESMS m/z 224 (M+H).

Reference： [1] Patent: WO2014/153055, 2014, A2, . Location in patent: Paragraph 0120-0121
[2] Patent: WO2015/20553, 2015, A1, . Location in patent: Paragraph 00113-00114
[3] Patent: WO2015/50471, 2015, A1, . Location in patent: Paragraph 00107; 00108
[4] Patent: WO2015/50472, 2015, A1, . Location in patent: Paragraph 00111; 00112

[ 1109230-25-2 ] Synthesis Path-Downstream 1~1

1
[ 67-56-1 ]
[ 1109230-25-2 ]
[ 201230-82-2 ]
[ 93258-88-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In N,N-dimethyl-formamide; at 22.0℃; under 760.051 Torr; for 156.0h;	Pd(dppf)Cb DCM (285 mg, 0.35 mmol) was added to a solution of 5-bromo- 3,4-dihydro-2H-isoquinolin-l-one (395 mg, 1.75 mmol) and TEA (1.22 mL, 8.74 mmol) in DMF (6.00 mL) at 22 C. The mixture was evacuated and refilled with CO for 3 cycles. MeOH (3.08 mL) was added, and the mixture was heated to 85 C under a CO atmosphere (1 atm) for 16 h. The mixture was diluted with EA (25 mL) and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure. The residue was diluted with EA (100 mL) and LhO (100 mL). The aq. phase was extracted with EA (3 x 25.0 mL). The combined organic layers were washed with brine (50 mL), dried (NaiSO^, filtered, and concentrated. The residue was purified by S1O2 chromatography (hexanes and EA) to provide 285 mg (80%) of methyl l-oxo-l,2,3,4-tetrahydroisoquinoline-5-carboxylate (INT 58-1). LCMS-ESI (m/z) calculated for C11H11NO3: 205.07; found 205.74 (M+H)+, tR = 1.82 min (Method 13). NMR (400 MHz, CDCh) d 8.30 (dd, J = 7.7, 1.5 Hz, 1H), 8.09 (dd, J = 7.8, 1.5 Hz, 1H), 7.42 (dd, J = 7.8 Hz, 1H), 5.95 (s, 1H), 3.92 (s, 3H), 3.58 - 3.52 (m, 2H), 3.49 - 3.40 (m, 2H).
80%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In N,N-dimethyl-formamide; at 85.0℃; under 760.051 Torr; for 16.0h;	To a stirred solution of 5-bromo-3,4-dihydro-2H-isoquinolin-1-one (395 mg, 1.0 equiv., 1.75 mmol) and Et3N (1.22 mL, 5.0 equiv., 8.74 mmol) in DMF (6 mL) was added Pd(dppf)Cl2·DCM (285 mg, 0.2 equiv., 0.35 mmol). The mixture was evacuated and refilled with CO for 3 cycles. MeOH (3.08 mL, 43.42 equiv., 76.00 mmol) was added, and the mixture was heated to 85 C under a CO atmosphere (1 atm) for 16 h. The mixture was diluted with EA (25 mL) and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure. The residue was diluted with EA (100 mL) and water (100 mL). The aqueous phase was extracted with EA (3 x 25 mL). The combined organic layers were washed with brine (50 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash SiO2 chromatography (0-100% EA/hexanes) to afford 285 mg (80 %) of methyl 1-oxo-1,2,3,4-tetrahydroisoquinoline-5- carboxylate (INT 6-A). MS-ESI calculated for C11H11NO3: 205.07; found 205.74 [M]+, tR = 1.82 min (Method 5). 1H NMR (400 MHz, CDC13) δ 8.30 (dd, J = 7.7, 1.5 Hz, 1H), 8.09 (dd, J = 7.8, 1.5 Hz, 1H), 7.42 (dd, J = 7.8 Hz, 1H), 5.95 (s, 1H), 3.92 (s, 3H), 3.58 - 3.52 (m, 2H), 3.49 - 3.40 (m, 2H).

Reference： [1]Patent: WO2020/198537,2020,A1 .Location in patent: Page/Page column 243-245
[2]Patent: WO2021/211839,2021,A1 .Location in patent: Page/Page column 71; 72

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Technical Information

? Acyl Group Substitution ? Alkyl Halide Occurrence ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bucherer-Bergs Reaction ? Chan-Lam Coupling Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Fischer Indole Synthesis ? General Reactivity ? Grignard Reaction ? Henry Nitroaldol Reaction ? Hiyama Cross-Coupling Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Lawesson's Reagent ? Leuckart-Wallach 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 Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Reformatsky Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Stille Coupling ? Stobbe Condensation ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

Historical Records

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[ 1109230-25-2 ]

Bromides

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7-Bromo-3,4-dihydro-2H-isoquinolin-1-one

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[ 1109230-25-2 ]

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P222	Do not allow contact with air.
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P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
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P308 + P313	IF exposed or concerned: Get medical advice/attention.
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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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[ CAS No. 1109230-25-2 ] {[proInfo.proName]}

Quality Control of [ 1109230-25-2 ]

Related Doc. of [ 1109230-25-2 ]

Product Details of [ 1109230-25-2 ]

Calculated chemistry of [ 1109230-25-2 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1109230-25-2 ]

Application In Synthesis of [ 1109230-25-2 ]

[ 1109230-25-2 ] Synthesis Path-Upstream 1~1

[ 1109230-25-2 ] Synthesis Path-Downstream 1~1

Technical Information

Related Functional Groups of [ 1109230-25-2 ]

Bromides

Amides

Related Parent Nucleus of [ 1109230-25-2 ]

Tetrahydroisoquinolines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1109230-25-2 ]

Related Parent Nucleus of
[ 1109230-25-2 ]