[ CAS No. 20357-20-4 ] {[proInfo.proName]}

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2D 3D

Structure of 20357-20-4 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 20357-20-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 20357-20-4 ]

SDS Specification

Alternatived Products of [ 20357-20-4 ]

Product Details of [ 20357-20-4 ]

CAS No. :	20357-20-4	MDL No. :	MFCD00456508
Formula :	C₇H₄BrNO₃	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	UFRVBZVJVRHSNR-UHFFFAOYSA-N
M.W :	230.02	Pubchem ID :	97233
Synonyms :

Calculated chemistry of [ 20357-20-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	48.35
TPSA :	62.89 ?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) :	-5.94 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.2
Log Po/w (XLOGP3) :	2.49
Log Po/w (WLOGP) :	2.17
Log Po/w (MLOGP) :	1.02
Log Po/w (SILICOS-IT) :	0.51
Consensus Log Po/w :	1.48

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.07
Solubility :	0.195 mg/ml ; 0.000846 mol/l
Class :	Soluble
Log S (Ali) :	-3.46
Solubility :	0.0805 mg/ml ; 0.00035 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.59
Solubility :	0.597 mg/ml ; 0.00259 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	3.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.82

Safety of [ 20357-20-4 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280	UN#:
Hazard Statements:	H302-H317	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 20357-20-4 ]

* 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 [ 20357-20-4 ]
Downstream synthetic route of [ 20357-20-4 ]

[ 20357-20-4 ] Synthesis Path-Upstream 1~1

1
[ 10601-80-6 ]
[ 20357-20-4 ]
[ 481054-89-1 ]

Yield	Reaction Conditions	Operation in experiment
60%	With tin(II) chloride dihdyrate In ethanol at 20 - 90℃;	Step 1: ethyl 6-bromoquinoline-3-carboxylate To a solution of 5-bromo-2-nitrobenzaldehyde (2 g, 9 mmol) in ethanol (46 mL) was added tin(II) chloride dihydrate (7.95 g, 35.2 mmol) and 3,3-diethoxypropionic acid ethyl ester (4.2 mL, 22 mmol). The reaction was heated to 90° C. for 16 hours. The reaction was then allowed to cool to room temperature and stir overnight. The reaction mixture was concentrated and the residue was dissolved in ethyl acetate. The mixture was poured into saturated aqueous sodium bicarbonate. The resulting emulsion was filtered through Celite, rinsing with ethyl acetate. The layers were separated and the aqueous was extracted with ethyl acetate. The combined organics were washed with brine, dried over magnesium sulfate, filtered, and concentrated. Purification by flash column chromatography (0-50percent ethyl acetate/heptanes) gave the title compound (1.41 g, 60percent) as a solid.

Reference： [1] Journal of Organic Chemistry, 2010, vol. 75, # 10, p. 3488 - 3491
[2] Patent: US2012/270893, 2012, A1, . Location in patent: Page/Page column 32

[ 20357-20-4 ] Synthesis Path-Downstream 1~9

1
[ 20357-20-4 ]
[ 19063-55-9 ]

Reference： [1]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 1796 - 1802

2
[ 10601-80-6 ]
[ 20357-20-4 ]
[ 481054-89-1 ]

Yield	Reaction Conditions	Operation in experiment
60%	With tin(II) chloride dihdyrate; In ethanol; at 20 - 90℃;	Step 1: ethyl 6-bromoquinoline-3-carboxylate To a solution of 5-bromo-2-nitrobenzaldehyde (2 g, 9 mmol) in ethanol (46 mL) was added tin(II) chloride dihydrate (7.95 g, 35.2 mmol) and 3,3-diethoxypropionic acid ethyl ester (4.2 mL, 22 mmol). The reaction was heated to 90 C. for 16 hours. The reaction was then allowed to cool to room temperature and stir overnight. The reaction mixture was concentrated and the residue was dissolved in ethyl acetate. The mixture was poured into saturated aqueous sodium bicarbonate. The resulting emulsion was filtered through Celite, rinsing with ethyl acetate. The layers were separated and the aqueous was extracted with ethyl acetate. The combined organics were washed with brine, dried over magnesium sulfate, filtered, and concentrated. Purification by flash column chromatography (0-50% ethyl acetate/heptanes) gave the title compound (1.41 g, 60%) as a solid.

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 3488 - 3491
[2]Patent: US2012/270893,2012,A1 .Location in patent: Page/Page column 32

3
[ 552-89-6 ]
[ 882772-99-8 ]
[ 5551-12-2 ]
[ 56990-05-7 ]
[ 20357-20-4 ]
[ 20357-21-5 ]
[ 1559060-83-1 ]
3,6-dibromo-2-nitrobenzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8%; 20%; 9%; 8%; 14%; 12%; 13%	With N-Bromosuccinimide; sulfuric acid; at 25℃; for 3h;	Treatment of 1 (504 mg, 3.33 mmol) and NBS (1.48 g, 8.30 mmol) in H2SO4 (3.0 mL) as described above provided after purification by chromatography (hexanes/EtOAc, 85:15) the following fractions in order of elution: (I) 7 (65 mg, 0.21 mmol, 9percent); (II) 2 (153 mg, 20percent), 4 (58 mg, 8percent), and 6 (128 mg, 12percent); (III) 5 (108 mg, 14percent), 8 (129 mg, 13percent), and 1 (17 mg, 3percent); (IV) 3 (57 mg, 0.25 mmol, 8percent).

Reference： [1]Synthetic Communications,2014,vol. 44,p. 954 - 958

4
[ 552-89-6 ]
[ 5551-12-2 ]
[ 56990-05-7 ]
[ 20357-20-4 ]
[ 20357-21-5 ]
[ 1559060-83-1 ]

Yield	Reaction Conditions	Operation in experiment
21%; 1%; 9%; 20%; 5%	With N-Bromosuccinimide; sulfuric acid; at 25℃; for 3h;	N-Bromosuccinimide (NBS) (1.48 g, 8.32 mmol) was added to a solution of 1 (1.01 g, 6.71 mmol) in H2SO4 (concentrated 5.0 mL). The resulting mixture was stirred at ambient temperature (3 h). The reaction was quenched with ice and extracted with ethyl acetate (320mL). The combined organic phases were washed with saturated NaCl (aqueous, 30 mL), dried (MgSO4), and filtered through a silica gel plug, and the solvents were evaporated under reduced pressure. The resulting brown oil was purified by column chromatography (hexanes=EtOAc, 8:2) to afford the following fractions in order of elution: (I) 7 (28 mg, 0.09 mmol, 1percent) as an off-white solid; (II) 2 (328 mg, 21percent), 4 (140 mg, 9percent), and 3,4-dibromo-2-nitrobenzaldehyde (6) (94 mg, 5percent); (III) 5 (310 mg, 20percent), 8 (65 mg, 3percent), 1 (168 mg, 17percent); (IV) 3 (54 mg, 0.23 mmol, 4percent).

Reference： [1]Synthetic Communications,2014,vol. 44,p. 954 - 958

5
[ 552-89-6 ]
[ 5551-12-2 ]
[ 56990-05-7 ]
[ 20357-20-4 ]
[ 20357-21-5 ]

Yield	Reaction Conditions	Operation in experiment
19%; 1%; 12%; 24%	With N-Bromosuccinimide; sulfuric acid; at 25℃; for 3h;	Treatment of 1 (986 mg, 6.53 mmol) with NBS (878 mg, 4.93 mmol) in H2SO4 (conc. 5.0 mL), as described in the paper gave after chromatography (hexanes/EtOAc, 8:2) the following fractions in order of elution: (I) 4-bromo-2-nitrobenzaldehyde (2)1 (216 mg, 19percent), 5-bromo-2-nitrobenzaldehyde (4)2 (134 mg, 12percent), and 4,5-dibromo-2-nitrobenzaldehyde (7) (18 mg, 1percent) as a yellow solid; (II) 6-bromo-2-nitrobenzaldehyde (5) (268 mg, 24percent),3 3,6-dibromo-2-nitrobenzaldehyde (8) (25 mg, 2percent),4 and 1 (409 mg, 41percent) as a yellow oil; (III) 3-bromo-2-nitrobenzaldehyde (3)5 as a yellow solid (60 mg, 0.26 mmol, 4percent).

Reference： [1]Synthetic Communications,2014,vol. 44,p. 954 - 958

6
[ 20357-20-4 ]
[ 74-89-5 ]
[ 465529-56-0 ]

Yield	Reaction Conditions	Operation in experiment
		Into a 500-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen were placed 5-bromo-2-nitrobenzaldehyde (30.0 g, 130.4 mmol, 1.0 equiv.), methanamine (71.5 mL, 1.1 equiv.), and propan-2-ol (300 mL). The resulting solution was stirred for 4 h at 80C. The mixture was cooled to rt and tributylphosphine (98 mL, 3.0 equiv.) was added. The resulting solution was stirred for 12 h at 80C and then extracted with 500 mL of ethyl acetate. The resulting mixture was washed sequentially with 300 mL of NH4CI (aq.) and 300 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1 :4). This resulted in 32 g (crude) of 5- bromo-2-methyl-2H-indazole A as a red oil: MS m/z MH+= 211

Reference： [1]Patent: WO2016/14904,2016,A1 .Location in patent: Page/Page column 21; 22

7
[ 20357-20-4 ]
[ 98-86-2 ]
[ 3894-25-5 ]

Yield	Reaction Conditions	Operation in experiment
64%		General procedure: Iron powder (0.4 eq.) was added to a solution of o-nitrobenzaldehyde (11a-11g, 1.0 eq.) in EtOH(2.0 mL) followed by HCl (0.05 eq.) [19]. The reaction mixture was refluxed for 40 min followedby cooling to room temperature. The corresponding aldehyde or ketone (1.2 eq.) was added to thereaction mixture followed by KOH (1.2 eq.). The reaction mixture was stirred at RT for 30 min andrefluxed for an additional 3 h. The reaction mixture was filtered, the filtrate was neutralized (HCl),extracted with EtOAc, and the combined extracts were dried and concentrated to dryness. The residuewas subjected to FCC (EtOAc-hexane, 3:7) to afford substituted quinolines 5a-7g.

Reference： [1]Molecules,2017,vol. 22

8
[ 20357-20-4 ]
[ 56904-86-0 ]
[ 1075-34-9 ]

Yield	Reaction Conditions	Operation in experiment
45%	With triphenylphosphine; In diphenylether; at 260℃; for 1h;	General procedure: In a 50 ml round bottom flask containing magnetic stir bar was charged with o-nitro benzaldehydes (2 mmol), phosphorane (2.2 mmol), triphenyl phosphine (4.6 mmol) and diphenyl ether (10 mL) and heated at 260 oC for 1 h. The reaction mass was then cooled to room temperature and poured on silica column. Products were isolated by eluting with petrolium ether to 3:1 pet ether: ethyl acetate.

Reference： [1]Tetrahedron Letters,2018,vol. 59,p. 1851 - 1854

9
[ 20357-20-4 ]
[ 3894-25-5 ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 5177 - 5186
[2]Journal of Organic Chemistry,2018,vol. 83,p. 13036 - 13044
[3]Chinese Journal of Chemistry,2020,vol. 38,p. 1691 - 1695

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Technical Information

? Alkyl Halide Occurrence ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Chaykovsky Reaction ? Corey-Fuchs Reaction ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hantzsch Dihydropyridine Synthesis ? Henry Nitroaldol Reaction ? Hiyama Cross-Coupling Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Julia-Kocienski Olefination ? Kinetics of Alkyl Halides ? Knoevenagel Condensation ? Kumada Cross-Coupling Reaction ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mukaiyama Aldol Reaction ? Nozaki-Hiyama-Kishi Reaction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Reformatsky Reaction ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Stetter Reaction ? Stille Coupling ? Stobbe Condensation ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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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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[ CAS No. 20357-20-4 ] {[proInfo.proName]}

Quality Control of [ 20357-20-4 ]

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Product Details of [ 20357-20-4 ]

Calculated chemistry of [ 20357-20-4 ] Expand+

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 20357-20-4 ]

[ 20357-20-4 ] Synthesis Path-Upstream 1~1

[ 20357-20-4 ] Synthesis Path-Downstream 1~9

Technical Information

Related Functional Groups of [ 20357-20-4 ]

Aryls

Bromides

Aldehydes

Nitroes

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[ 20357-20-4 ]