[ CAS No. 70478-63-6 ] {[proInfo.proName]}

Name: 70478-63-6|4-Bromoisoindoline-1,3-dione|95%
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SKU: A114382
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3d Animation Molecule Structure of 70478-63-6

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Quality Control of [ 70478-63-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 70478-63-6 ]

SDS Specification

Alternatived Products of [ 70478-63-6 ]

Product Details of [ 70478-63-6 ]

CAS No. :	70478-63-6	MDL No. :	MFCD15144658
Formula :	C₈H₄BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ANENLORAJJKWAA-UHFFFAOYSA-N
M.W :	226.03	Pubchem ID :	22607307
Synonyms :

Calculated chemistry of [ 70478-63-6 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	49.52
TPSA :	46.17 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) :	-6.68 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.24
Log Po/w (XLOGP3) :	1.41
Log Po/w (WLOGP) :	0.95
Log Po/w (MLOGP) :	1.99
Log Po/w (SILICOS-IT) :	2.19
Consensus Log Po/w :	1.56

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.5
Solubility :	0.715 mg/ml ; 0.00316 mol/l
Class :	Soluble
Log S (Ali) :	-1.98
Solubility :	2.35 mg/ml ; 0.0104 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.64
Solubility :	0.0521 mg/ml ; 0.000231 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.62

Safety of [ 70478-63-6 ]

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 [ 70478-63-6 ]

* 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 [ 70478-63-6 ]
Downstream synthetic route of [ 70478-63-6 ]

[ 70478-63-6 ] Synthesis Path-Upstream 1~2

1
[ 2518-24-3 ]
[ 70478-63-6 ]

Reference： [1] Journal of the Chemical Society, 1939, p. 836

2
[ 116-69-8 ]
[ 70478-63-6 ]

Reference： [1] Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences and Medicine, 1949, vol. 18/5 A, p. 17

[ 70478-63-6 ] Synthesis Path-Downstream 1~15

1
[ 2518-24-3 ]
[ 70478-63-6 ]

Reference： [1]Journal of the Chemical Society,1939,p. 836

2
[ 70478-63-6 ]
[ 108-24-7 ]
2-acetyl-4-bromo-isoindoline-1,3-dione [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 1631,1633

3
[ 116-69-8 ]
[ 70478-63-6 ]

Reference： [1]Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences and Medicine,1949,vol. 18/5 A,p. 17

4
[ 900517-08-0 ]
[ 70478-63-6 ]
[ 552330-85-5 ]

Yield	Reaction Conditions	Operation in experiment
55%	With triethylamine;tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine; In N,N-dimethyl-formamide; at 75℃; for 6h;	Example 32B tert-butyl (1S)-2-[5-(1,3-dioxo-2,3-dihydro-1H-isoindol-5-yl)pyridin-3-yl]oxy}-1-(1H-indol-3-ylmethyl)ethylcarbamate A solution of Example 32A (0.2 g, 0.31 mmol) and <strong>[70478-63-6]6-bromophthalimide</strong> (0.084 g, 0.4 mmol) in DMF (2 mL) was treated with Pd2 dba3 (0.04 g, 0.02 mmol), tri-o-tolylphosphine (0.02 g, 0.01 mmol), and triethylamine (0.06 mL, 0.4 mmol). The reaction was heated to 75° C. for 6 hours in a sealed tube and concentrated. The residue was purified by flash column chromatography on silica gel with 1:1 hexanes/ethyl acetate to provide the desired product (0.116 g, 55percent).

Reference： [1]Patent: US2003/199511,2003,A1 .Location in patent: Page/Page column 26

5
[ 70478-63-6 ]
[ 74-88-4 ]
[ 90224-73-0 ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of <strong>[70478-63-6]3-bromophthalimide</strong> (10.0 g, 44.2 mmol), potassium carbonate (12.2 g, 88.5 mmol) and potassium iodide (50 mg, 0.30 mmol) are stirred in 80 mL DMF for 15 min. The reaction mixture is cooled to 0 0C, methyl iodide (3.04 mL, 48.7 mmol) is added <n="39"/>and the reaction mixture is stirred overnight at RT. The reaction mixture is filtered, the solids are washed with DMF and the filtrate is poured in water. The mixture is extracted with ethyl acetate and the combined organic phases are washed several times with water, dried over MgSO4 and concentrated in vacuo. Yield: 7.10 g.

Reference： [1]Patent: WO2009/112565,2009,A1 .Location in patent: Page/Page column 37; 38

6
[ 70478-63-6 ]
4-bromo-1-methylisoindoline [ No CAS ]

Reference： [1]Patent: WO2017/158388,2017,A1

7
[ 70478-63-6 ]
tert-butyl 4-bromo-1-methylisoindoline-2-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/158388,2017,A1

8
[ 70478-63-6 ]
[ 75-16-1 ]
4-bromo-3-hydroxy-3-methylisoindolin-1-one [ No CAS ]
7-bromo-3-hydroxy-3-methylisoindolin-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; dichloromethane; at 0 - 20℃; for 2h;Inert atmosphere;	Step a. To a solution of 4-bromoisoindoline-l,3-dione (CAS Number 70478-63-6, 15.00 g, 66.4 mmol) in DCM (150 ml) was dropwise added methyl magnesium bromide (1 M in THF) (199 ml, 199 mmol) at 0°C under N2 atmosphere. The reaction mixture was stirred at rt for 2 h. The reaction mixture was combined with three other batches prepared on the same scale by an identical method. The resulting reaction mixture was poured in to NH4C1 solution (500 ml) and extracted with the DCM (3 x 1 L). The combined organic phases was dried over Na2S04, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography (30-32 percent EtOAc in hexane) yielding a mixture of 7-bromo-3-hydroxy-3-methylisoindolin-1-one and 4-bromo-3-hydroxy- 3-methylisoindolin-1-one (37.00 g, 153.6 mmol). LCMS: Method A, 1.435 min, MS: ES+ 242.33, 244.33.

Reference： [1]Patent: WO2017/158388,2017,A1 .Location in patent: Page/Page column 178

9
[ 70478-63-6 ]
[ 75-16-1 ]
7-bromo-3-methylisoindolin-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
9.2 g		Step b. A mixture of 7-bromo-3-hydroxy-3-methylisoindolin-l-one and 4-bromo-3-hydroxy-3 -methyl isoindolin-l-one (12.00 g, 49.8 mmol) in DCM (100 ml) was cooled to -40°C. Triethylsilane (80.4 ml, 498 mmol) was added to the reaction mixture at -40°C under N2 atmosphere. Boron trifluoride diethyletherate (18.7 ml, 149.4 mmol) was added to the reaction mixture at -40°C under N2 atmosphere. The reaction mixture was stirred at 0°C for 1 h. The resulting reaction mixture was combined with two other batches prepared on the same scale by an identical method. The resulting reaction mixture was poured into NaHC03 solution (500 ml) and extracted with the DCM (3 x 1000 ml). The combined organic phase was dried over Na2S04, filtered and concentrated under reduced pressure. The crude material obtained was purified by column chromatography (3percent EtOAc in DCM) yielding 7-bromo-3-methylisoindolin-l-one (9.200 g, 40.9 mmol). LCMS: Method A, 1.521 min, MS: ES+ 226.11, 228.11; NMR (400 MHz, CDC13) delta ppm 7.61 (dd, J=7.2, 1.2 Hz, 1 H), 7.43 - 7.38 (m, 3 H), 7.68 - 7.63 (m, 1 H), 1.52 (d, J=6.8 Hz, 3 H).

Reference： [1]Patent: WO2017/158388,2017,A1 .Location in patent: Page/Page column 178

10
[ 70478-63-6 ]
[ 74-88-4 ]
[ 64954-16-1 ]

Yield	Reaction Conditions	Operation in experiment
92%		[00290] To a solution of 4-bromoisoindole-l,3-dione 1 (226 mg, 1.0 mmol) in MeCN (5 mL) was added CS2CO3 (652 mg, 2.0 mmol). The reaction mixture was stirred at rt for 15 min then cooled to 0-5 °C. lodomethane (0.2 mL, 3.0 mmol) added dropwise and the reaction mixture was allowed to warm to rt and stirred for a further 16 h. The mixture was partitioned between EtOAc and water and the aqueous layer extracted with EtOAc. The combined organic layers were washed with water, brine, then dried (Na2S04), filtered and concentrated under reduced pressure. The residue was purified (silica gel; eluting with 20percent EtOAc in hexanes) to afford the compound 2 (220 mg, 92percent) as a yellow solid. 1H MR (400 MHz, DMSO-i): delta 7.97 (m, 1H), 7.86 (m, 1H), 7.70 (m, 1H), 3.03 (s, 3H).

Reference： [1]Patent: WO2019/70742,2019,A1 .Location in patent: Paragraph 00290

11
[ 70478-63-6 ]
[ 2746-25-0 ]
4-bromo-2-(4-methoxybenzyl)isoindoline-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With caesium carbonate; In N,N-dimethyl-formamide; at 0 - 20℃; for 16h;	[00287] To a solution of 4-bromoisoindole-l,3-dione 1 (226 mg, 1.0 mmol) in DMF (8 mL) was added Cs2C03 (652 mg, 2.0 mmol). The mixture was cooled to 0-5 °C and PMB-Br (302 mg, 1.5 mmol) was added dropwise. The reaction was allowed to warm to rt and stirred for 16 h. The mixture was partitioned between water and EtOAc, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with water and brine, dried (Na2S04), filtered and concentrated under reduced pressure. The residue was purified (silica gel; eluting with 20percent EtOAc in hexanes) to afford compound 2 (208 mg, 74percent) as a yellow solid. 1H NMR (400 MHz, CDC13): delta 7.80 - 7.83 (m, 2H), 7.60 (m, 1H), 7.53 - 7.57 (m, 2H), 6.85 - 6.90 (m, 2H), 4.80 (s, 2H), 3.79 (s, 3H).

Reference： [1]Patent: WO2019/70742,2019,A1 .Location in patent: Paragraph 00287

12
[ 64954-16-1 ]
[ 1448427-99-3 ]
[ 70478-63-6 ]

Yield	Reaction Conditions	Operation in experiment
51%	With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; XPhos; In 1,4-dioxane; at 100℃; for 16h;Inert atmosphere;	[00291] To a mixture of Int-A (82 mg, 0.4 mmol) and compound 2 (120 mg, 0.5 mmol) in 1,4- dioxane (5.0 mL) was added Pd2(dba)3 (18 mg, 0.02 mmol), xantphos (23 mg, 0.04 mmol) and K2C03 (110 mg, 0.8 mmol). The reaction mixture was heated at 100 °C under a N2 atmosphere for 16 h. The mixture was cooled to rt and partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc and the combined organic layers washed with water, brine, then dried (Na2S04), filtered and concentrated under reduced pressure. The residue was purified by preparative TLC (eluting with 5percent MeOH in DCM) to afford compound 3 (75 mg, 51percent) as a yellow solid. 1H MR (400 MHz, DMSO-i): delta 9.24 (s, 1H), 8.89 (s, 1H), 8.35 (m, 1H), 7.89 (m, 1H), 7.72 (m, 1H), 7.65 (m, 1H), 7.42 (m, 1H), 7.27 (m, 1H), 5.33 (m, 1H), 3.02 (s, 3H), 1.36 - 1.37 (m, 6H); LCMS Mass: 363.1 (M++l).

Reference： [1]Patent: WO2019/70742,2019,A1 .Location in patent: Paragraph 00291

13
[ 70478-63-6 ]
4-((6-(4-isopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-yl)amino)-2-(4-methoxybenzyl)isoindoline-1,3-dione [ No CAS ]

Reference： [1]Patent: WO2019/70742,2019,A1

14
[ 70478-63-6 ]
4-((6-(4-isopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-yl)amino)isoindoline-1,3-dione [ No CAS ]

Reference： [1]Patent: WO2019/70742,2019,A1

15
[ 82-73-5 ]
[ 70478-63-6 ]

Yield	Reaction Conditions	Operation in experiment
89%	With formamide at 200℃; for 2h; Inert atmosphere;	19.3 Step 3: 4-bromo-2H-isoindole-1,3-dione. A mixture of 4-bromo-2-benzofuran-1,3- dione (500.00 mg, 2.203 mmol, 1.00 equiv) and formamide (793.63 mg, 17.620 mmol, 8.00 equiv) was stirred for 2 h at 200 oC under nitrogen atmosphere. The reaction was monitored by LCMS. The mixture was allowed to cool down to room temperature. The reaction was quenched with water/ice at 0 oC. The precipitated solids were collected by filtration and washed with water (4 x 2 mL). The resulting solid was dried in an oven under reduced pressure. This resulted in 4-bromo- 2H-isoindole-1,3-dione (443.8 mg, 89%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) d 11.52 (s, 1H), 7.97 (dd, J = 8.0, 0.9 Hz, 1H), 7.81 (dd, J = 7.3, 0.8 Hz, 1H), 7.70 (t, J = 7.7 Hz, 1H). LC/MS (ESI, m/z): [(M- 1)]- = 223.85, 225.85.

Reference： [1]Current Patent Assignee: KYMERA THERAPEUTICS INC - WO2021/11631, 2021, A1 Location in patent: Paragraph 00384; 00386

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Ghs Precautionary Statements

Precautionary Statements-General
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Code	Phrase
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P220	Keep/Store away from clothing/combustible materials.
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Code	Phrase
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P321
P322
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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
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. 70478-63-6 ] {[proInfo.proName]}

Quality Control of [ 70478-63-6 ]

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[ 70478-63-6 ] Synthesis Path-Upstream 1~2

[ 70478-63-6 ] Synthesis Path-Downstream 1~15

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Bromides

Amides

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Indolines

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[ 70478-63-6 ]

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[ 70478-63-6 ]