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[ CAS No. 345-24-4 ] {[proInfo.proName]}

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Chemical Structure| 345-24-4

Chemical Structure| 345-24-4

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Quality Control of [ 345-24-4 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 345-24-4 ]

CAS No. :	345-24-4	MDL No. :	MFCD00129166
Formula :	C₆H₂BrF₂NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OOUUWURPSUSDTD-UHFFFAOYSA-N
M.W :	237.99	Pubchem ID :	223078
Synonyms :

Calculated chemistry of [ 345-24-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	42.88
TPSA :	45.82 ?2

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) :	-5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.54
Log Po/w (XLOGP3) :	2.64
Log Po/w (WLOGP) :	3.48
Log Po/w (MLOGP) :	2.49
Log Po/w (SILICOS-IT) :	1.26
Consensus Log Po/w :	2.28

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.28
Solubility :	0.124 mg/ml ; 0.000522 mol/l
Class :	Soluble
Log S (Ali) :	-3.25
Solubility :	0.133 mg/ml ; 0.000559 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.19
Solubility :	0.152 mg/ml ; 0.000638 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	3.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.17

Safety of [ 345-24-4 ]

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 [ 345-24-4 ]

* 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 [ 345-24-4 ]
Downstream synthetic route of [ 345-24-4 ]

[ 345-24-4 ] Synthesis Path-Upstream 1~1

1
[ 345-24-4 ]
[ 124-41-4 ]
[ 935288-20-3 ]
[ 1352244-77-9 ]

Reference： [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 1, p. 449 - 464
[2] Patent: WO2012/125603, 2012, A1, . Location in patent: Page/Page column 33-34
[3] Patent: US2015/111885, 2015, A1, . Location in patent: Paragraph 0510; 0511

[ 345-24-4 ] Synthesis Path-Downstream 1~3

1
[ 345-24-4 ]
[ 452-92-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	With iron; acetic acid; In ethanol; at 80℃; for 2h;	To a stirred solution of 1-bromo-2,4-difluoro-5-nitro-benzene (1) (3.0 g, 0.013 mol) in ethanol (40 mL), iron powder (4.928 g, 0.088 mol) and acetic acid (10.60 mL, 0.176 mol) were added and the reaction mixture was stirred at 80 C. for 2 h. The progress of the reaction was monitored by TLC. The reaction mixture was filtered through a celite bed and the filtrate was concentrated under reduced pressure. The residue was dissolved in water and extracted with ethyl acetate. Combined organic layers were concentrated under reduced pressure to afford the title compound as an off white solid. Yield (2.0 g, 90%). LCMS (ESI positive ion) m/z: calculated: 208.1; observed: 210.1 (M+2).
68.21%	With iron; ammonium chloride; In ethanol; water; for 6h;	5-Bromo-2,4-difluoronitrobenzene (2.36 g, 10 mmol) was dissolved in a mixed solvent of ethanol / water (5/1, 24 mL), and iron powder (1.68 g, 30 mmol) and ammonium chloride ( 1.60g, 30mmol), stir evenly, heat up the reaction after dripping, TLC monitor, the raw materials are completely reacted after 6h, suction filtration under mild heat conditions after stopping the reaction, the filtrate is selected (PE / EA = 10/1), the column is shallow Yellow oil 1.73 g, yield: 68.21%.
59.1%	With water; iron; ammonium chloride; In tetrahydrofuran; ethanol; at 95℃; for 1.5h;Heating / reflux;	A 250-mL RB-flask, charged with 5-bromo-2,4-difluoronitrobenzene (5.04 g, 21.3 [MMOL),] saturated [NH4CL] (25.0 mL), iron powder (5.00 g, 89.5 mmol), ethanol (100 mL), THF (50.0 mL) and water (25.0 mL) was refluxed at [95 C] for 1.5 hours. After cooling to room temperature, saturated [NAHCO3] (100 mL) was added and the mixture was filtered through Celite and the Celite was washed with EtOAc (3 x 50 mL). The combined filtrates were washed with H20 and brine, dried over [MGSO4,] filtered and concentrated in vacuo. The crude product was purified by flash chromatography (EtOAc: hexanes 1: 9) to afford 5- bromor-2, [4-DIFLUOROANILINE] (2.61 g, [59. 1%). 1H] NMR (400 MHz, [CDC13)] 5 6.97 (dd, 1H, J = 7.2, 6.7 Hz), 6.85 (t, 1H, [J] = 8.2 Hz), 3.63 (br, 2H).

Reference： [1]Patent: US2020/102319,2020,A1 .Location in patent: Paragraph 1743-1744
[2]Patent: CN110483366,2019,A .Location in patent: Paragraph 0727; 0733-0735
[3]Journal of Medicinal Chemistry,2007,vol. 50,p. 3870 - 3882
[4]Patent: WO2004/5257,2004,A1 .Location in patent: Page 67-68
[5]Journal of the American Chemical Society,1956,vol. 78,p. 2593,2596

2
[ 345-24-4 ]
[ 124-41-4 ]
[ 935288-20-3 ]
[ 1352244-77-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	In methanol; at 0 - 20℃; for 22.0h;	To a stirred solution of l-bromo-2,4-difluoro-5-nitro-benzene (12.1 g, 50.8 mmol) in MeOH (100 mL) was added 25% sodium methoxide in MeOH (12 mL, 53.4 mmol, 12 mL) at 0 C, and the reaction mixture was stirred at 0C for 2h and then at RT for 20h. Volatile solvent was removed under reduced pressure, and the resultant residue was partitioned between 'PrOAc and water. The organic layer was washed with water and brine, dried over Na2S04. filtered and concentrated in vacuo. The crude product was purified by column chromatography (SiCh:?PrOAc / heptane) to afford 10.9g (86% yield) of a mixture of l-bromo-4-fluoro-2- methoxy-5-nitro-benzene and l-bromo-2-fluoro-4-methoxy-5-nitro-benzene (~2: l ratio). 1- Bromo-4-fluoro-2-methoxy-5-nitrobenzene: ' H NMR (400 MHz, CDCf) d 8.36 (d, J = 8.0 Hz, 1H), 6.77 (d, J = 12.3 Hz, 1H), 4.00 (s, 3H); l-bromo-2-fluoro-4-methoxy-5-nitro-benzene: 'H NMR (400 MHz, CDCf) d 8.16 (d, J = 7.1 Hz, 1H), 6.89 (d, J = 9.8 Hz, 1H), 3.97 (s, 3H);
	In methanol; at 0℃; for 2.0h;	Example 4el-Bromo-2-fluoro-4-methoxy-5-nitro-benzene (10c) and l-Bromo-4-fluoro-2- methoxy-5-nitro-benzene l-Bromo-2,4-difluoro-5-nitro-benzene (960mg, 4.0 mmol) was dissolved in MeOH (20 mL) was cooled to 0C and treated with 0.5M Sodium Methoxide in MeOH solution (8.1 mL, 4 mmol). After 2 hours the reaction solution was concentrated under reduced pressure and the residue was partitioned between EtOAc and water. The organic phase was dried over sodium sulfate (Na2S04), filtered, and concentrated under reduced pressure to give 833mg (83%) of yellowish oil. 1H NMR spectral analysis supported that the product was a mixture of l-Bromo-2-fluoro-4-methoxy-5-nitro-benzene and l-Bromo-4- fluoro-2-methoxy-5-nitro-benzene (~1 :2 ratio). The assignments of the respective regioisomers were determined based on further analysis of a purified l-Bromo-2-fluoro-4- methoxy-5-nitro-benzene analog, generated from the subsequent steps to this reaction. 1H NMR (DMSO- 6) delta 8.41-8.39 (d, 0.63H), 8.36-8.34 (d, 0.26H), 7.57-7.54 (d, 0.30H), 7.45-7.42 (d, 0.70H), 4.01 (s, 2.2H), 3.95 (s, 0.9H).
	In methanol; at 0 - 20℃; for 18.0h;Reflux;	At 0 C., sodium methoxide (344 mg, 6.3 mmol) in dry MeOH (7 mL) was added dropwise to 1-bromo-2,4-dif- luoro-5-nitrobenzene(1 g, 4.2 mmol) in dry MeOH (l8mL). The mixture was stirred at room temperature for 10 hand then refluxed for 8 h. After extractive work up, purification by silica gel chromatography (PE:EA=1:0 to 10:1) gave a mix-ture of the two title compounds (765 mg, 72.9%) in about a 2:1 ratio as a yellow solid. LCMS: 249.9 (M+H)

Reference： [1]Patent: WO2020/51099,2020,A1 .Location in patent: Page/Page column 0395-0400
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 449 - 464
[3]Patent: WO2012/125603,2012,A1 .Location in patent: Page/Page column 33-34
[4]Patent: US2015/111885,2015,A1 .Location in patent: Paragraph 0510; 0511

3
[ 345-24-4 ]
[ 108-59-8 ]
[ 893620-44-5 ]

Yield	Reaction Conditions	Operation in experiment
		c) 6-Bromo-5-fluoroindolin-2-one A suspension of (4-bromo-5-fluoro-2-nitrophenyl)-acetic acid/ (2-bromo-5-fluoro-4-nitro- phenyl)-acetic acid (2.6: 1 mixture, 37.3 g, 134 mmol) and iron (30.0 g, 537 mmol) in acetic acid (671 ml) was heated to 100C for 7 hours and then cooled to room temperature. Remaining elemental iron was removed with a magnetic rod. Ice water (900 ml) was added to the reaction mixture. The precipitate was filtered off, washed four times with water and then suspended in an ice-cold aqueous solution of 25% HC1 (300 ml) and cone. HC1 (50 ml). After stirring for 10 minutes the precipitate was filtered off and washed four times with water. The precipitate was suspended in a mixture of 1 M aqueous Na2C03 (400 ml) solution and 0.1 M NaOH (100 ml) and stirred for 40 minutes. The precipitate was filtered off and washed four times with 0.1 M aqueous NaOH, three times with water and once with diisopropylether to give title compound as light grey solid (20.5 g). MS ESI (m/z): 228.0/ 230.0 [(M-H)"]. 1H NMR (DMSO-D6, 400 MHz): (ppm) = 10.47 (bs, 1H), 7.31-7.28 (m, 1H), 7.01-6.99 (m, 1H), 3.49 (s, 2H).
20.5 g		a) 2-(4-Bromo-5-fluoro-2-nitro-phenyl)-malonic acid dimethyl ester/ 2-(2-Bromo-5-fluoro-4-nitro-phenyl)-malonic acid dimethyl ester A suspension of NaH (60 % in mineral oil, 20.2 g, 504 mmol) in dioxane (233 ml) was cooled to11 C. A solution of 1-bromo-2,4-difluoro-5-nitrobenzene (50 g, 26.5 ml, 210 mmol) anddimethyl malonate (33.3 g, 28.9 ml, 242 mmol) in dioxane (467 ml) was carefully added at 11 - 14 C within 45 minutes (gas evolution). After completion of the addition the reaction mixture was kept at 12 C for another hour and then warmed to room temperature. After 16 hours the reaction mixture was cooled to 10 C and 100 ml saturated aqueous ammonium chloride solutionwas added. The reaction mixture was diluted with tert-butyl methyl ether, water and saturated aqueous ammonium chloride solution. The aqueous phase was extracted with tert-butyl methyl ether, the combined organic phases were washed with saturated aqueous ammonium chloride solution and brine and dried over sodium sulfate. The solvent was evaporated and the residue purified by silica gel chromatography using ethyl acetate heptane as eluent. The title compoundswere obtained as yellow liquid (53.7 g) as a 2.6:1 mixture and used for the next reaction without further purification.. A mixture of 2-(4-bromo-5 -fluoro-2-nitro-phenyl)-malonic acid dimethyl ester 2-(2-bromo-5- fluoro-4-nitro-phenyl)-malonic acid dimethyl ester (2.6:1 mixture, 53.7 g, 153 mmol) and 6 Maqueous hydrochloric acid (767 ml) was heated to reflux for 7 hours and then cooled to 5 C. The precipitate was filtered, washed with water and with n-pentane and then coevaporated 3 times with toluene to give 25.9 g of a mixture of the title compounds as white solid. The mother liquor was extracted with ethyl acetate and the combined organic phases dried over sodium sulfate. The solvent was evaporated and the residue triturated with n-pentane and then coevaporated with toluene to give 11.42 g of a mixture of the title compounds as an off-white solid. This material was combined with the first crop to give a total of 37.32 g of the title compounds as a 2.6 :1 mixture which was used for the next reaction without further purification.A suspension of (4-bromo-5-fluoro-2-nitrophenyl)-acetic acid/ (2-bromo-5-fluoro-4-nitro- phenyl)-acetic acid (2.6:1 mixture, 37.3 g, 134 mmol) and iron (30.0 g, 537 mmol) in acetic acid (671 ml) was heated to 100 C for 7 hours and then cooled to room temperature. Remaining elemental iron was removed with a magnetic rod. Ice water (900 ml) was added to the reaction mixture. The precipitate was filtered off, washed four times with water and then suspended in anice-cold aqueous solution of 25 % HC1 (300 ml) and conc. HC1 (50 ml). After stuffing for 10 minutes the precipitate was filtered off and washed four times with water.The precipitate was suspended in a mixture of 1 M aqueous Na2CO3 (400 ml) solution and 0.1 M NaOH (100 ml) and stirred for 40 minutes. The precipitate was filtered off and washed four times with 0.1 M aqueous NaOH, three times with water and once with diisopropylether to givetitle compound as light grey solid (20.5 g). MS ESI (m/z): 228.0/ 230.0 [(M-H)i.1H NMR (DMSO-D6, 400 MHz): (ppm) = 10.47 (bs, 1H), 7.3 1-7.28 (m, 1H), 7.01-6.99 (m, 1H), 3.49 (s, 2H).

Reference： [1]Patent: WO2014/40969,2014,A1 .Location in patent: Page/Page column 29-30
[2]Patent: WO2014/202493,2014,A1 .Location in patent: Page/Page column 54; 55

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Preparation of Alkylbenzene ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Vilsmeier-Haack Reaction

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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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