[ CAS No. 608-30-0 ] {[proInfo.proName]}

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2D 3D

Structure of 608-30-0 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 608-30-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 608-30-0 ]

SDS Specification

Alternatived Products of [ 608-30-0 ]

Product Details of [ 608-30-0 ]

CAS No. :	608-30-0	MDL No. :	MFCD00007638
Formula :	C₆H₅Br₂N	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	XIRRDAWDNHRRLB-UHFFFAOYSA-N
M.W :	250.92	Pubchem ID :	69098
Synonyms :

Calculated chemistry of [ 608-30-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	1.0
Molar Refractivity :	46.25
TPSA :	26.02 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.97 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.1
Log Po/w (XLOGP3) :	2.62
Log Po/w (WLOGP) :	2.8
Log Po/w (MLOGP) :	2.99
Log Po/w (SILICOS-IT) :	2.5
Consensus Log Po/w :	2.6

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.54
Solubility :	0.0724 mg/ml ; 0.000289 mol/l
Class :	Soluble
Log S (Ali) :	-2.82
Solubility :	0.383 mg/ml ; 0.00153 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.75
Solubility :	0.0448 mg/ml ; 0.000179 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.32

Safety of [ 608-30-0 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:
Hazard Statements:	H315-H317-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 608-30-0 ]

* 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 [ 608-30-0 ]
Downstream synthetic route of [ 608-30-0 ]

[ 608-30-0 ] Synthesis Path-Upstream 1~1

1
[ 608-30-0 ]
[ 1435-54-7 ]

Yield	Reaction Conditions	Operation in experiment
29%	Stage #1: at 0 - 10℃; for 1 h; Stage #2: at 0 - 220℃; for 3 h;	Step 1: 1,3-dibromo-2-fluorobenzene To a mixture of 2,6-dibromoaniline (5.0 g, 20 mmol) and HCl (12 N, 10 mL) was added NaNO₂ (2.1 g, 30 mmol) at 0° C. The reaction mixture was stirred at 0-10° C. for 1 h, and then NH₄BF₄ solution (4.2 g, 40 mmol) was added dropwise. The reaction mixture was stirred at 0-10° C. for 1 h. The precipitate was filtered and dried. The residue obtained was heated to 220° C. for 2 h, cooled to rt and dissolved with EA (150 mL), washed with NaOH (2 N, 200 mL). The organic layer was dried over Na₂SO₄, filtered and concentrated under reduced pressure to give 1,3-dibromo-2-fluorobenzene (1.45 g, yield 29percent).

Reference： [1] Patent: US2013/131016, 2013, A1, . Location in patent: Paragraph 0352; 0353
[2] Acta Chimica Academiae Scientiarum Hungaricae, 1957, vol. 10, p. 227,229

[ 608-30-0 ] Synthesis Path-Downstream 1~11

1
[ 608-30-0 ]
[ 608-21-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 60℃; for 1h;	In a 500-mL round-bottom flask was dissolved 5.78 g (25.9 mmol) of CuBr2 in 200 mL of dry CH3CN and the mixture heated to 60 C. To this warm solution was added 3.80 mL (31.9 mmol) tert-butyl nitrite, followed by a solution of 5.01 g (19.9 mmol) of commercially available 2,6-dibromoaniline 22 in 50 mL CH3CN. The mixture was stirred at 60 C for 1 h, then cooled to room temperature and poured into 200 mL 20% aqueous ammonia. The mixture was extracted with hexane (2 x 200 mL) and the combined organic phase was washed sequentially with 20% aqueous ammonia (100 mL), water (100 mL), brine (50 mL), and then dried over anhydrous magnesium sulfate. The contents were filtered and concentrated under reduced pressure. The resulting crude material was recrystallized from ethanol to give 5.12 g (80%) of 1,2,3-tribromobenzene 23 as an off-white solid, mp = 88-90 C. 1H NMR (CDCl3): d 7.58 (d, J = 8.0 Hz, 2 H), 7.03 (t, J = 8.0 Hz, 1H); 13C NMR (CDCl3): d 132.6, 129.2, 127.7, 126.2. The physical and spectral data is consistent with that which was previously reported for this compound: (1) Menzel, K.; Fisher, E. L.; DiMichele, L.; Frantz, D. E.; Nelson, T. D.; Kress, M. H. J. Org. Chem. 2006, 71, 2188-2191; (2) Teclechiel, D.; Sundstroem, M.; Marsh, G. Chemosphere 2009, 74, 421-427. The second reference includes low resolution mass spectral data.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 913 - 917
[2]Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti,1908,vol. <5> 17 I,p. 473

2
[ 608-30-0 ]
[ 1435-54-7 ]

Yield	Reaction Conditions	Operation in experiment
29%		Step 1: 1,3-dibromo-2-fluorobenzene To a mixture of 2,6-dibromoaniline (5.0 g, 20 mmol) and HCl (12 N, 10 mL) was added NaNO2 (2.1 g, 30 mmol) at 0° C. The reaction mixture was stirred at 0-10° C. for 1 h, and then NH4BF4 solution (4.2 g, 40 mmol) was added dropwise. The reaction mixture was stirred at 0-10° C. for 1 h. The precipitate was filtered and dried. The residue obtained was heated to 220° C. for 2 h, cooled to rt and dissolved with EA (150 mL), washed with NaOH (2 N, 200 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to give 1,3-dibromo-2-fluorobenzene (1.45 g, yield 29percent).

Reference： [1]Patent: US2013/131016,2013,A1 .Location in patent: Paragraph 0352; 0353
[2]Acta Chimica Academiae Scientiarum Hungaricae,1957,vol. 10,p. 227,229

3
[ 39150-45-3 ]
[ 608-30-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; In water; at 170℃; for 3.0h;	To a mixture of 50.0 g sulfanilamide, 850 mL water and 200 mL 48% HBr solution, 90.0 g sodium perborate was added at 85 C. The mixture was stirred at 80-85 C for 30 min and then was cooled to room temperature and filtered. The residue was washed to be neutral by water. The solid was desulfonated by reacting with 70% sulfuric acid solution for 3 h under reflux. Crude product was obtained by steam distillation and further purified by recrystallization in ethanol. 1H NMR (500 MHz, CDCl3, delta in ppm): 7.35-7.40 (d, 2H, Ar-Hm), 6.5 (t, 1H, Ar-Hp).

Reference： [1]Organic Syntheses,1944,vol. 24,p. 48
[2]Monatshefte fur Chemie,1915,vol. 36,p. 132
[3]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1989,vol. 28,p. 472 - 476
[4]Journal of Molecular Catalysis A: Chemical,2014,vol. 390,p. 76 - 82

4
[ 7664-93-9 ]
[ 39150-45-3 ]
[ 608-30-0 ]

Reference： [1]Monatshefte fur Chemie,1915,vol. 36,p. 132

5
[ 7664-93-9 ]
[ 39150-45-3 ]
[ 608-30-0 ]
[ 147-82-0 ]

Reference： [1]Archiv der Pharmazie,1943,vol. 281,p. 193,200

6
[ 608-30-0 ]
[ 89694-46-2 ]
[ 1257236-13-7 ]

Yield	Reaction Conditions	Operation in experiment
47%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 150℃; for 1h;Microwave irradiation;	<strong>[89694-46-2]2-chloro-5-methoxyphenylboronic acid</strong> (1.25 g, 6.71 mmol), 2,6-dibromoaniline (1.851 g, 7.38 mmol), sodium carbonate (6.71 mL, 13.41 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.465 g, 0.40 mmol) were dissolved in dioxane (10 mL), degassed and sealed into a microwave tube. The reaction was heated to 1500C for 1 hour in the microwave reactor and cooled to room temperature.The reaction mixture was poured into saturated aqueous NH4CI solution (100 mL), extracted with EtOAc (100 mL), and the organic layer was washed with water (50 mL) and saturated brine (50 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford an orange oil. The crude product was purified by flash silica chromatography, elution gradient 0 to 10percent EtOAc in isohexane. Pure fractions were evaporated to dryness to afford 3-bromo-2'- chloro-5'-methoxybiphenyl-2-amine (0.993 g, 47 percent) as a white solid; 1H NMR (400 MHz, CDCI3) delta 3.73 (3H, s), 3.95 (2H, s), 6.61 (1 H, t), 6.73 - 6.78 (1 H, m), 6.83 (1 H, d), 6.92 - 6.94 (1 H, m), 7.31 - 7.34 (1 H, m), 7.38 - 7.40 (1 H, m)

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 6066 - 6074
[2]Patent: WO2010/136778,2010,A1 .Location in patent: Page/Page column 43

7
[ 608-30-0 ]
[ 331646-99-2 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 676 - 679

8
[ 608-30-0 ]
[ 219735-99-6 ]
[ 1332939-47-5 ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 6066 - 6074

9
[ 1122-12-9 ]
[ 608-30-0 ]
3,4-dibromo-1-(2,6-dibromophenyl)-1H-pyrrole-2,5-dione [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 8094 - 8096

10
[ 608-30-0 ]
[ 172732-52-4 ]
[ 946147-06-4 ]

Yield	Reaction Conditions	Operation in experiment
36.7%	With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate monohydrate; In toluene; at 100℃; for 6h;Inert atmosphere;	Step 1: Synthesis of 4-bromo-6-aminophenanthridine A three neck 1 L round bottom flask was charged with 2,6-dibromoaniline (143.51 g, 0.57 mole), 2-cyanophenylbornic acid trimethylene ester (34.35 g, 0.19 mole), K3PO4. H2O (43.89 g, 0.1906 mole), PdCl2(PPh3)2 (6.67 g, 9.5 mmole) and anhydrous toluene (700 ml). The reaction mixture was heated to 100° C. under nitrogen for 6 hrs. The reaction mixture was then concentrated to dryness and subjected to column chromatography to obtain the title compound (19.11 g, 36.7percent).

Reference： [1]Patent: US9281483,2016,B2 .Location in patent: Page/Page column 86; 87

11
[ 870119-58-7 ]
[ 608-30-0 ]
C₄₂H₂₉N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water;Reflux;	15.0 g (59.8 mmol) of Intermediate (2,6-dibromoaniline), 53.0 g (143 mmol) of <strong>[870119-58-7]9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole</strong>, 6.91 g (5.98 mmol) of tetrakistriphenylphosphine palladium(0) (Pd(PPh3)4), and 41.3 g (299 mmol) of potassium carbonate were added to a solution of 260 ml of THF and 130 ml of water and mixed. The mixed solution was stirred under reflux. After completion of the reaction, the resulting reaction solution was cooled to room temperature, and an extraction process was performed thereon to remove an aqueous solution layer therefrom. The obtained residue was filtered through silica gel under reduced pressure, and the filtrate was concentrated under reduced pressure. The resulting residue was then separated by silica gel column chromatography, thereby providing 14.8 g (yield: 43%) of a desired compound, Intermediate (AA). LC-Mass (cald: 575.24 g/mol, found: M+1=576 g/mol).

Reference： [1]Patent: US2017/369439,2017,A1 .Location in patent: Paragraph 0549-0552

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Leuckart-Wallach Reaction ? Mannich Reaction ? Petasis Reaction ? Preparation of Alkylbenzene ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Specialized Acylation Reagents-Vilsmeier Reagent ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Ugi Reaction ? Vilsmeier-Haack Reaction

Historical Records

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[ 608-30-0 ]

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Ghs Precautionary Statements

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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. 608-30-0 ] {[proInfo.proName]}

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Product Details of [ 608-30-0 ]

Calculated chemistry of [ 608-30-0 ] Expand+

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Druglikeness

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Medicinal Chemistry

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[ 608-30-0 ] Synthesis Path-Upstream 1~1

[ 608-30-0 ] Synthesis Path-Downstream 1~11

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Aryls

Bromides

Amines

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[ 608-30-0 ]