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

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Chemical Structure| 608-30-0
Chemical Structure| 608-30-0
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Product Details of [ 608-30-0 ]

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

Calculated chemistry of [ 608-30-0 ]

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 Ų

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:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H317-H319-H335 Packing Group:N/A
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   1~33

  • 1
  • [ 608-30-0 ]
  • [ 19821-80-8 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 11, p. 2772 - 2775
[2] Tetrahedron Letters, 2009, vol. 50, # 24, p. 2860 - 2864
[3] Organic Letters, 2004, vol. 6, # 10, p. 1589 - 1592
[4] Chemistry - A European Journal, 2017, vol. 23, # 25, p. 6029 - 6033
[5] Angewandte Chemie - International Edition, 2008, vol. 47, # 5, p. 888 - 890
[6] Journal of Organic Chemistry, 1986, vol. 51, # 16, p. 3162 - 3165
  • 2
  • [ 608-30-0 ]
  • [ 601-84-3 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1984, # 12, p. 3485 - 3497
[2] Chemische Berichte, 1894, vol. 27, p. 1584
[3] Justus Liebigs Annalen der Chemie, 1892, vol. 269, p. 219
[4] Australian Journal of Chemistry, 1974, vol. 27, p. 2209 - 2228
  • 3
  • [ 39150-45-3 ]
  • [ 608-30-0 ]
Reference: [1] Organic Syntheses, 1944, vol. 24, p. 48
[2] Monatshefte fuer Chemie, 1915, vol. 36, p. 132
[3] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1989, vol. 28, # 6, p. 472 - 476
[4] Journal of Molecular Catalysis A: Chemical, 2014, vol. 390, p. 76 - 82
  • 4
  • [ 615-36-1 ]
  • [ 615-57-6 ]
  • [ 608-30-0 ]
Reference: [1] Synthetic Communications, 2000, vol. 30, # 20, p. 3669 - 3675
[2] Tetrahedron Letters, 2000, vol. 41, # 13, p. 2083 - 2085
  • 5
  • [ 601-84-3 ]
  • [ 608-30-0 ]
Reference: [1] Organic Letters, 2009, vol. 11, # 5, p. 1051 - 1054
  • 6
  • [ 62-53-3 ]
  • [ 608-30-0 ]
Reference: [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 40, p. 8568 - 8575
  • 7
  • [ 615-36-1 ]
  • [ 615-57-6 ]
  • [ 608-30-0 ]
  • [ 147-82-0 ]
Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 13, p. 2083 - 2085
  • 8
  • [ 3282-10-8 ]
  • [ 608-30-0 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 11, p. 3210 - 3222
  • 9
  • [ 619-45-4 ]
  • [ 608-30-0 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 11, p. 3210 - 3222
  • 10
  • [ 78824-10-9 ]
  • [ 608-30-0 ]
Reference: [1] Chemische Berichte, 1877, vol. 10, p. 1539
[2] Journal fuer Praktische Chemie (Leipzig), 1905, vol. <2> 71, p. 562
[3] Justus Liebigs Annalen der Chemie, 1889, vol. 253, p. 285
[4] Journal of the Chemical Society, 1908, vol. 93, p. 735
[5] Recueil des Travaux Chimiques des Pays-Bas, 1912, vol. 31, p. 338
  • 11
  • [ 121-57-3 ]
  • [ 608-30-0 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1889, vol. 253, p. 285
[2] Journal of the Chemical Society, 1908, vol. 93, p. 735
  • 12
  • [ 4123-72-2 ]
  • [ 608-30-0 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 11, p. 3210 - 3222
  • 13
  • [ 99-09-2 ]
  • [ 608-30-0 ]
Reference: [1] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1908, vol. <5> 17 I, p. 473
[2] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1908, vol. <5> 17 I, p. 473
  • 14
  • [ 96237-91-1 ]
  • [ 608-30-0 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1921, vol. 40, p. 347
  • 15
  • [ 59870-37-0 ]
  • [ 608-30-0 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1921, vol. 40, p. 347
  • 16
  • [ 53324-38-2 ]
  • [ 608-30-0 ]
Reference: [1] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1908, vol. <5> 17 I, p. 473
  • 17
  • [ 1159339-39-5 ]
  • [ 217662-69-6 ]
  • [ 608-30-0 ]
Reference: [1] Russian Journal of General Chemistry, 2008, vol. 78, # 5, p. 892 - 897
  • 18
  • [ 13402-32-9 ]
  • [ 608-30-0 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1892, vol. 269, p. 219
[2] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1908, vol. <5> 17 I, p. 473
  • 19
  • [ 7664-93-9 ]
  • [ 171002-36-1 ]
  • [ 608-30-0 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1922, vol. 41, p. 471
  • 20
  • [ 7664-93-9 ]
  • [ 78824-10-9 ]
  • [ 608-30-0 ]
Reference: [1] Chemische Berichte, 1877, vol. 10, p. 1539
[2] Journal fuer Praktische Chemie (Leipzig), 1905, vol. <2> 71, p. 562
[3] Justus Liebigs Annalen der Chemie, 1889, vol. 253, p. 285
[4] Journal of the Chemical Society, 1908, vol. 93, p. 735
  • 21
  • [ 7664-93-9 ]
  • [ 39150-45-3 ]
  • [ 608-30-0 ]
Reference: [1] Monatshefte fuer Chemie, 1915, vol. 36, p. 132
  • 22
  • [ 7664-93-9 ]
  • [ 39150-45-3 ]
  • [ 608-30-0 ]
  • [ 147-82-0 ]
Reference: [1] Archiv der Pharmazie (Weinheim, Germany), 1943, vol. 281, p. 193,200
  • 23
  • [ 608-30-0 ]
  • [ 1435-54-7 ]
YieldReaction ConditionsOperation 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
  • 24
  • [ 608-30-0 ]
  • [ 13402-32-9 ]
Reference: [1] Organic Letters, 2009, vol. 11, # 5, p. 1051 - 1054
[2] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 11, p. 3210 - 3222
[3] Journal of Materials Chemistry, 1999, vol. 9, # 3, p. 661 - 672
  • 25
  • [ 608-30-0 ]
  • [ 19230-27-4 ]
YieldReaction ConditionsOperation in experiment
49% With copper(l) chloride; isopentyl nitrite In acetonitrile at 65℃; for 2 h; Step 1:
1,3-dibromo-2-chlorobenzene
To a mixture of isoamyl nitrite (585 mg, 5 mmol) and CuCl (396 mg, 4 mmol) in acetonitrile (10 mL) was slowly added 2,6-dibromoaniline (502 mg, 2 mmol) at 65° C.
The reaction mixture was stirred at 65° C. for 2 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, cooled to rt, concentrated under reduced pressure, dissolved with EA (30 mL), washed with water (20 mL).
The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure.
The residue was purified by column chromatography eluted with PE to give 1,3-dibromo-2-chlorobenzene (270 mg, yield 49percent) as solid.
Reference: [1] Patent: US2013/131016, 2013, A1, . Location in patent: Paragraph 0331; 0332
[2] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1908, vol. <5> 17 I, p. 473
[3] Journal of the Chemical Society, 1901, vol. 79, p. 1303
  • 26
  • [ 608-30-0 ]
  • [ 544-92-3 ]
  • [ 6575-12-8 ]
YieldReaction ConditionsOperation in experiment
38% With tert.-butylnitrite In dimethyl sulfoxide at 50℃; for 1.08333 h; EXAMPLE 42; N-[(2-(2,6-Dibromolphenyl)-1-[4-(1,1-dimethylethyl)phenyl]methyl}-4-hydroxy-6-oxo-1,6-dihydro-5-pyrimidinyl)carbonyl]glycine; 42a) 2,6-Dibromobenzonitrile; 2,6-Dibromoaniline (0.251 g, 1.00 mmol) was added to a stirred solution of copper (I) cyanide (0.116 g, 1.30 mmol) in dimethylsulfoxide (10 mL) at 50° C. under nitrogen. tert-Butyl nitrite (0.357 mL, 3.00 mmol) was injected over 5 min and the mixture stirred for 1 h at 50° C., then cooled and poured into 1 M aqueous hydrochloric acid (100 mL). The mixture was extracted with ethyl acetate and the extracts washed with water, brine, then dried (MgSO4). The solvent was evaporated under reduced pressure and the residue chromatographed (silica gel, 1-9percent methanol/dichloromethane) to give the title compound (0.100 g, 38percent). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.33 (t, J=8.08 Hz, 1 H) 7.67 (d, J=8.08 Hz, 2 H).
Reference: [1] Patent: US2008/171756, 2008, A1, . Location in patent: Page/Page column 30
[2] Australian Journal of Chemistry, 1974, vol. 27, p. 2209 - 2228
  • 27
  • [ 608-30-0 ]
  • [ 6575-12-8 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1892, vol. 269, p. 219
[2] Chemische Berichte, 1894, vol. 27, p. 1584
  • 28
  • [ 608-30-0 ]
  • [ 151-50-8 ]
  • [ 6575-12-8 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1984, # 12, p. 3485 - 3497
  • 29
  • [ 608-30-0 ]
  • [ 6575-12-8 ]
Reference: [1] Chemical Science, 2016, vol. 7, # 7, p. 4355 - 4363
  • 30
  • [ 608-30-0 ]
  • [ 114344-60-4 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 4, p. 676 - 679
  • 31
  • [ 608-30-0 ]
  • [ 182344-57-6 ]
Reference: [1] Patent: WO2016/197078, 2016, A1,
  • 32
  • [ 608-30-0 ]
  • [ 331647-05-3 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 4, p. 676 - 679
  • 33
  • [ 608-30-0 ]
  • [ 331646-99-2 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 4, p. 676 - 679
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