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[ CAS No. 128-08-5 ] {[proInfo.proName]}

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Excepted Quantity USD 0.00
Limited Quantity USD 15-60
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3d Animation Molecule Structure of 128-08-5
Chemical Structure| 128-08-5
Chemical Structure| 128-08-5
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Product Details of [ 128-08-5 ]

CAS No. :128-08-5 MDL No. :MFCD00005510
Formula : C4H4BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :PCLIMKBDDGJMGD-UHFFFAOYSA-N
M.W : 177.98 Pubchem ID :67184
Synonyms :

Calculated chemistry of [ 128-08-5 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.5
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 34.31
TPSA : 37.38 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.44 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.07
Log Po/w (XLOGP3) : -0.07
Log Po/w (WLOGP) : 0.06
Log Po/w (MLOGP) : 0.11
Log Po/w (SILICOS-IT) : 0.85
Consensus Log Po/w : 0.41

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.9
Solubility : 22.4 mg/ml ; 0.126 mol/l
Class : Very soluble
Log S (Ali) : -0.26
Solubility : 97.0 mg/ml ; 0.545 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.95
Solubility : 19.8 mg/ml ; 0.111 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.45

Safety of [ 128-08-5 ]

Signal Word:Danger Class:8,5.1
Precautionary Statements:P201-P202-P210-P220-P221-P234-P261-P264-P272-P273-P280-P302+P352-P305+P351+P338-P308+P313-P333+P313-P337+P313-P370+P378-P390-P391-P405-P406-P501 UN#:3084
Hazard Statements:H272-H290-H315-H317-H319-H341-H400 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 128-08-5 ]

* 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 [ 128-08-5 ]
  • Downstream synthetic route of [ 128-08-5 ]

[ 128-08-5 ] Synthesis Path-Upstream   1~85

  • 1
  • [ 188290-36-0 ]
  • [ 128-08-5 ]
  • [ 1003-09-4 ]
Reference: [1] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1988, vol. 27, # 6, p. 538 - 539
  • 2
  • [ 128-08-5 ]
  • [ 616-44-4 ]
  • [ 14282-76-9 ]
Reference: [1] Patent: EP308170, 1989, A1,
  • 3
  • [ 56-23-5 ]
  • [ 128-08-5 ]
  • [ 616-44-4 ]
  • [ 14282-76-9 ]
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 4018
[2] Journal of the American Chemical Society, 1949, vol. 71, p. 1201,1203
  • 4
  • [ 554-14-3 ]
  • [ 56-23-5 ]
  • [ 128-08-5 ]
  • [ 94-36-0 ]
  • [ 45438-73-1 ]
Reference: [1] Journal of the American Chemical Society, 1949, vol. 71, p. 1201,1203
  • 5
  • [ 872-31-1 ]
  • [ 128-08-5 ]
  • [ 3140-93-0 ]
Reference: [1] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1988, vol. 27, # 6, p. 538 - 539
  • 6
  • [ 554-14-3 ]
  • [ 56-23-5 ]
  • [ 128-08-5 ]
  • [ 765-58-2 ]
Reference: [1] Journal of the American Chemical Society, 1949, vol. 71, p. 1201,1203
  • 7
  • [ 1003-09-4 ]
  • [ 128-08-5 ]
  • [ 3141-27-3 ]
Reference: [1] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1988, vol. 27, # 6, p. 538 - 539
  • 8
  • [ 1003-09-4 ]
  • [ 56-23-5 ]
  • [ 128-08-5 ]
  • [ 3141-27-3 ]
Reference: [1] Arkiv foer Kemi, 1957, vol. 11, p. 373,379, 380
  • 9
  • [ 128-08-5 ]
  • [ 516-12-1 ]
Reference: [1] Russian Journal of Organic Chemistry, 2001, vol. 37, # 10, p. 1503 - 1504
[2] Journal of the American Chemical Society, 2018, vol. 140, # 19, p. 6039 - 6043
[3] Russian Journal of Organic Chemistry, 2018, vol. 54, # 1, p. 131 - 138[4] Zh. Org. Khim., 2018, vol. 54, # 1, p. 131 - 138,8
  • 10
  • [ 88-15-3 ]
  • [ 128-08-5 ]
  • [ 5370-25-2 ]
Reference: [1] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1988, vol. 27, # 6, p. 538 - 539
  • 11
  • [ 128-08-5 ]
  • [ 95-15-8 ]
  • [ 7342-82-7 ]
Reference: [1] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1988, vol. 27, # 6, p. 538 - 539
  • 12
  • [ 128-08-5 ]
  • [ 5407-87-4 ]
  • [ 89856-44-0 ]
Reference: [1] Patent: US5693812, 1997, A,
  • 13
  • [ 128-08-5 ]
  • [ 274-09-9 ]
  • [ 67-66-3 ]
  • [ 2635-13-4 ]
Reference: [1] Journal of Organic Chemistry, 1958, vol. 23, p. 908
  • 14
  • [ 56-23-5 ]
  • [ 128-08-5 ]
  • [ 493-08-3 ]
  • [ 94-36-0 ]
  • [ 3875-78-3 ]
Reference: [1] Annales de Chimie (Cachan, France), 1954, vol. <12> 9, p. 431,363
  • 15
  • [ 2810-04-0 ]
  • [ 128-08-5 ]
  • [ 5751-83-7 ]
Reference: [1] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1988, vol. 27, # 6, p. 538 - 539
  • 16
  • [ 56-23-5 ]
  • [ 128-08-5 ]
  • [ 21785-09-1 ]
  • [ 94-36-0 ]
  • [ 22395-22-8 ]
Reference: [1] Proceedings - Indian Academy of Sciences, Section A, 1952, # 36, p. 134,137
  • 17
  • [ 56-23-5 ]
  • [ 128-08-5 ]
  • [ 104-93-8 ]
  • [ 94-36-0 ]
  • [ 2746-25-0 ]
Reference: [1] Huaxue Xuebao, 1959, vol. 25, p. 277,285[2] Chem.Abstr., 1960, p. 17306
  • 18
  • [ 128-08-5 ]
  • [ 2835-77-0 ]
  • [ 39859-36-4 ]
YieldReaction ConditionsOperation in experiment
100% at 0 - 20℃; 2-benzoyl-4-bromoaniline
Pathway 2: 2-aminobenzophenone (1 eq., 5 mmol, 0.986 g) is dissolved in dichloromethane at 0° C. N-bromosuccinimide (1 eq., 5 mmol, 0.890 g) is then added in small portions. The temperature of the reaction mixture is allowed to return to ambient temperature over approximately two hours. The reaction mixture is then evaporated and 2-benzoyl-4-bromoaniline is quantitatively obtained.
1H NMR (400 MHz, CDCl3) δ: 7.64-7.63 (d, J=7.2 Hz, 2H, 2′), 7.56 (s, 1H, 6), 7.55-7.54 (d, J=2.4 Hz, 1H, 4′), 7.50-7.47 (t, J=7.6 Hz, 2H, 3′), 7.38-7.35 (q, J=8.8-2.4 Hz, 1H, 4), 6.66-6.64 (d, J=8.4 Hz, 1H, 3), 6.09 (s, 2H, NH2).
MS (ES) m/z 276 (M+H+), 198, 105.
Reference: [1] Patent: US2016/83355, 2016, A1, . Location in patent: Paragraph 0340; 0341; 0342; 0343
  • 19
  • [ 56-23-5 ]
  • [ 128-08-5 ]
  • [ 4744-08-5 ]
  • [ 3400-55-3 ]
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 973
  • 20
  • [ 128-08-5 ]
  • [ 110-83-8 ]
  • [ 18926-24-4 ]
  • [ 3540-84-9 ]
  • [ 82469-57-6 ]
  • [ 1521-51-3 ]
Reference: [1] Journal of the American Chemical Society, 1982, vol. 104, # 25, p. 7267 - 7274
  • 21
  • [ 56-23-5 ]
  • [ 128-08-5 ]
  • [ 110-83-8 ]
  • [ 1521-51-3 ]
Reference: [1] Journal of the Chemical Society, 1958, p. 3727
[2] Justus Liebigs Annalen der Chemie, 1942, vol. 551, p. 115
  • 22
  • [ 128-08-5 ]
  • [ 110-83-8 ]
  • [ 1521-51-3 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1942, vol. 551, p. 115
  • 23
  • [ 128-08-5 ]
  • [ 99-04-7 ]
  • [ 123-56-8 ]
  • [ 6515-58-8 ]
YieldReaction ConditionsOperation in experiment
61% for 2.75 h; Irradiation; Heating / reflux Synthesis of 3-bromomethylbenzoic acid: In a 1 L round bottom flask fitted with a reflux condenser, a stirred suspension of 10.00 g of m-toluic acid and 14.37 g (1.1 eq.) N-bromosuccinimide in 735 mL chloroform was sparged for 0.5 h with nitrogen. The sparging was discontinued, and the suspension was stirred and irradiated under nitrogen atmosphere using a 500 W quartz halogen lamp at 75percent power, causing the solids to dissolve and the chloroform to reflux. The red color of the reaction mixture disappeared after 1.25 h, and 14.37 g of N-bromosuccinimide was added. The reaction mixture was stirred and irradiated under nitrogen atmosphere with a 500 W quartz halogen lamp at 75percent power for another 1.5 h, at which time the solution became colorless. The solvent volume was reduced in vacuo to about 100 mL, and then cooled to-20 °C. The resultant suspension was vacuum filtered through a bed of dry silica. The silica was washed with 800 mL of chloroform. The chloroform filtrate was reduced in vacuo to about 100 mL, and then cooled to-20 °C. The resultant crystals were vacuum filtered, washed with 30 mL of chloroform followed by 50 mL of hexanes, then dissolved in 250 mL chloroform and washed in a separatory funnel with 3 x 300 mL volumes of water followed by one 300 mL volume of brine to remove traces of succinimide. The organic phase was dried with magnesium sulfate, vacuum filtered, and the solvent was removed in vacuo to provide 9.56 g (61percent) of 3- bromomethylbenzoic acid as a white crystalline power.
Reference: [1] Patent: WO2005/97123, 2005, A2, . Location in patent: Page/Page column 79-80
  • 24
  • [ 128-08-5 ]
  • [ 99-04-7 ]
  • [ 6515-58-8 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1994, vol. 31, # 2, p. 457 - 480
  • 25
  • [ 56-23-5 ]
  • [ 128-08-5 ]
  • [ 88-72-2 ]
  • [ 94-36-0 ]
  • [ 3958-60-9 ]
Reference: [1] Journal of the American Chemical Society, 1949, vol. 71, p. 2137,2138,2140
  • 26
  • [ 56-23-5 ]
  • [ 128-08-5 ]
  • [ 90-12-0 ]
  • [ 3163-27-7 ]
Reference: [1] Annales de Chimie (Cachan, France), 1948, vol. <12> 3, p. 62,84
[2] Journal of the Chemical Society, 1946, p. 830
  • 27
  • [ 56-23-5 ]
  • [ 128-08-5 ]
  • [ 78-67-1 ]
  • [ 99-08-1 ]
  • [ 3958-57-4 ]
Reference: [1] Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences, 1953, vol. <B> 56, p. 75,78
  • 28
  • [ 56-23-5 ]
  • [ 103-82-2 ]
  • [ 128-08-5 ]
  • [ 4870-65-9 ]
Reference: [1] Doklady Bolgarskoi Akademii Nauk, 1957, vol. 10, p. 137,139
  • 29
  • [ 103-82-2 ]
  • [ 128-08-5 ]
  • [ 107-06-2 ]
  • [ 4870-65-9 ]
Reference: [1] Doklady Bolgarskoi Akademii Nauk, 1957, vol. 10, p. 137,139
  • 30
  • [ 128-08-5 ]
  • [ 1153-85-1 ]
Reference: [1] Patent: US8231942, 2012, B2,
  • 31
  • [ 3510-66-5 ]
  • [ 128-08-5 ]
  • [ 101990-45-8 ]
Reference: [1] Patent: WO2003/106455, 2003, A1, . Location in patent: Page 55
  • 32
  • [ 128-08-5 ]
  • [ 99-51-4 ]
  • [ 34241-39-9 ]
  • [ 6425-66-7 ]
Reference: [1] Patent: US5936089, 1999, A,
  • 33
  • [ 128-08-5 ]
  • [ 13991-36-1 ]
Reference: [1] Patent: US5270343, 1993, A,
  • 34
  • [ 56-23-5 ]
  • [ 128-08-5 ]
  • [ 623-70-1 ]
  • [ 37746-78-4 ]
Reference: [1] Iowa State College Journal of Science, 1946, vol. 21, p. 44[2] Chem.Abstr., 1947, p. 3045
  • 35
  • [ 128-08-5 ]
  • [ 922-67-8 ]
  • [ 23680-40-2 ]
YieldReaction ConditionsOperation in experiment
88% With silver nitrate In acetone at 20℃; for 6 h; Methyl propiolate (52 ml, 0.583 mol) is combined with recrystallized N- bromo-succinimide (120 g, 0.674 mol) in 1,700 ml acetone under nitrogen. The solution is treated with silver nitrate (9.9 g, 0.0583 mol) neat in a single lot and the reaction is stirred 6 h at RT. The acetone is removed under reduced pressure (25C, bath temperature) to provide a gray slurry. The slurry is washed with 2 x 200 ml hexane, the gray solid is removed by filtration, and the filtrate is concentrated in vacuo to provide 95 g of a pale yellow oily residue. The crude material is distilled via short path under reduced pressure (65C, about 25 mm Hg) into a dry ICE/ACETONE cooled receiver to give 83.7 g (88percent) of methyl-3-bromo-propiolate as a pale yellow oil. Anal. calc'd for C4H3BRO2 : C, 29.48 ; H, 1.86. Found: C, 29.09 ; H, 1.97.
Reference: [1] Patent: WO2004/39815, 2004, A2, . Location in patent: Page 44
  • 36
  • [ 56-23-5 ]
  • [ 128-08-5 ]
  • [ 97-64-3 ]
  • [ 617-35-6 ]
  • [ 70-23-5 ]
Reference: [1] Journal of Organic Chemistry, 1957, vol. 22, p. 1678
[2] Journal of the American Chemical Society, 1954, vol. 76, p. 5796
  • 37
  • [ 56-23-5 ]
  • [ 128-08-5 ]
  • [ 108-67-8 ]
  • [ 94-36-0 ]
  • [ 27129-86-8 ]
Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 4229,4230
  • 38
  • [ 128-08-5 ]
  • [ 140-29-4 ]
  • [ 5798-79-8 ]
Reference: [1] Patent: WO2005/120516, 2005, A2, . Location in patent: Page/Page column 47; 48
  • 39
  • [ 128-08-5 ]
  • [ 99-94-5 ]
  • [ 6232-88-8 ]
YieldReaction ConditionsOperation in experiment
67.7% With dibenzoyl peroxide In tetrachloromethane Third Step
Synthesis of 4-(Bromomethyl)benxoic acid (III) STR18
13.6 g (100 mmol) of p-toluic acid STR19 17.8 g (100 mmol) of N-bromo succinoimide STR20 and 1 g (4.1 mmol) of dibenzoyl peroxide were suspended in 125 ml of carbon tetrachloride, and the mixture was heated under vigorous stirring and reacted under reflux (oil bath 93° C., inner temp. 74° C.) for 2 hours to obtain a reaction mixture of yellow milky liquid.
The reaction mixture was cooled in an ice bath, and the precipitated crystalline product was filtered and washed with hexane.
The crystalline product was further washed with water, and recrystallized from ethanol to obtain 14.6 g of white needle crystals of 4-(bromomethyl)benzoic acid (III).
Yield 67.7percent.
Reference: [1] Patent: US5143644, 1992, A,
  • 40
  • [ 128-08-5 ]
  • [ 120-12-7 ]
  • [ 1564-64-3 ]
Reference: [1] Acta Chimica Academiae Scientiarum Hungaricae, 1958, vol. 15, p. 183,186
  • 41
  • [ 56-23-5 ]
  • [ 128-08-5 ]
  • [ 85-01-8 ]
  • [ 573-17-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1944, vol. 556, p. 1,7
  • 42
  • [ 128-08-5 ]
  • [ 83-32-9 ]
  • [ 2051-98-1 ]
Reference: [1] Dalton Transactions, 2014, vol. 43, # 35, p. 13434 - 13444
  • 43
  • [ 108-32-7 ]
  • [ 128-08-5 ]
  • [ 83-32-9 ]
  • [ 2051-98-1 ]
Reference: [1] Journal of the American Chemical Society, 1958, vol. 80, p. 4327,4329
  • 44
  • [ 128-08-5 ]
  • [ 83-32-9 ]
  • [ 68-12-2 ]
  • [ 2051-98-1 ]
Reference: [1] Journal of the American Chemical Society, 1958, vol. 80, p. 4327,4329
  • 45
  • [ 128-08-5 ]
  • [ 533-18-6 ]
  • [ 704-65-4 ]
YieldReaction ConditionsOperation in experiment
90% With 2,2'-azobis(isobutyronitrile); o-methylphenylacetic acid In cyclohexane at 80℃; for 0.5 h; 60.07 g of [2-(bromoethyl)phenyl] acetate, 400 mmol of 2-methylphenylacetic acid,106.8 g of N-bromosuccinimide and 500 ml of cyclohexane were added to a 1 L flask and added with vigorous stirring3.284 g of azobisisobutyronitrile and stir for 30 minutes,Mixing was stirred at 80C until no further conversion was observed. Work-up after reaction: then cooled to room temperature, the precipitate was removed by filtration and the filtrate was washed with cyclohexane to give compound S6-5 in 90percent yield.
Reference: [1] Patent: CN107573360, 2018, A, . Location in patent: Paragraph 0017; 0019; 0027
  • 46
  • [ 56-23-5 ]
  • [ 128-08-5 ]
  • [ 129-00-0 ]
  • [ 1714-29-0 ]
Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1948, vol. 226, p. 87
  • 47
  • [ 128-08-5 ]
  • [ 129-00-0 ]
  • [ 71-43-2 ]
  • [ 1714-29-0 ]
Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1948, vol. 226, p. 87
  • 48
  • [ 128-08-5 ]
  • [ 95-48-7 ]
  • [ 13319-71-6 ]
Reference: [1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 17, p. 3187 - 3194
  • 49
  • [ 128-08-5 ]
  • [ 100-12-9 ]
  • [ 19935-81-0 ]
YieldReaction ConditionsOperation in experiment
90% With dibenzoyl peroxide In tetrachloromethane for 1 h; Heating / reflux A mixture of 1-ethyl-4-nitro-benzene (3.4 mL, 25 mmol), N-bromosuccinimide (4.38 g, 24.6 mmol) and benzoylperoxide (0.04g, 0.18 mmol) in carbon tetrachloride (30 mL) was refluxed 1h, cooled and filtered, washing with 1:1 ethyl acetate : hexanes. The filtrate was evaporated and purified by flash chromatography (SiO2) eluted with 2:98 ethyl acetate : hexanes to provide 1-(1-bromo-ethyl)-4-nitro-benzene (5.18 g, 90percent yield) as a yellow oil. 1H-NMR (CDCl3, 500 MHz) 8.22 (d, 2H), 7.62 (d, 2H), 5.22 (q, 1H), 2.08 (d, 3H) ppm; HPLC (Method A) 3.837 min.
Reference: [1] Patent: WO2004/46120, 2004, A2, . Location in patent: Page 173;174
  • 50
  • [ 128-08-5 ]
  • [ 100-84-5 ]
  • [ 19614-12-1 ]
Reference: [1] Patent: EP2746301, 2014, A1, . Location in patent: Page/Page column
[2] Patent: US2015/344596, 2015, A1,
  • 51
  • [ 128-08-5 ]
  • [ 86-73-7 ]
  • [ 1133-80-8 ]
Reference: [1] Patent: US6555682, 2003, B1,
  • 52
  • [ 108-32-7 ]
  • [ 128-08-5 ]
  • [ 86-73-7 ]
  • [ 1133-80-8 ]
Reference: [1] Journal of the American Chemical Society, 1958, vol. 80, p. 4327,4329
  • 53
  • [ 128-08-5 ]
  • [ 86-73-7 ]
  • [ 109-63-7 ]
  • [ 71-43-2 ]
  • [ 1133-80-8 ]
Reference: [1] Journal of the American Chemical Society, 1958, vol. 80, p. 4327,4329
  • 54
  • [ 56-23-5 ]
  • [ 128-08-5 ]
  • [ 93-04-9 ]
  • [ 3401-47-6 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1944, vol. 556, p. 1,7
  • 55
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  • [ 128-08-5 ]
  • [ 86-73-7 ]
  • [ 1940-57-4 ]
Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1948, vol. 226, p. 87
[2] Journal of the American Chemical Society, 1948, vol. 70, p. 895
[3] Justus Liebigs Annalen der Chemie, 1944, vol. 555, p. 133,137,144
  • 56
  • [ 128-08-5 ]
  • [ 86-73-7 ]
  • [ 7726-95-6 ]
  • [ 71-43-2 ]
  • [ 1940-57-4 ]
Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1948, vol. 226, p. 87
[2] Journal of the American Chemical Society, 1948, vol. 70, p. 895
[3] Justus Liebigs Annalen der Chemie, 1944, vol. 555, p. 133,137,144
  • 57
  • [ 128-08-5 ]
  • [ 2216-69-5 ]
  • [ 5467-58-3 ]
Reference: [1] Patent: US2011/108827, 2011, A1,
  • 58
  • [ 56-23-5 ]
  • [ 128-08-5 ]
  • [ 2216-69-5 ]
  • [ 5467-58-3 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1944, vol. 556, p. 1,7
  • 59
  • [ 128-08-5 ]
  • [ 121-92-6 ]
  • [ 6307-83-1 ]
Reference: [1] Patent: WO2004/24682, 2004, A2, . Location in patent: Page 15-16
  • 60
  • [ 128-08-5 ]
  • [ 67-66-3 ]
  • [ 121-33-5 ]
  • [ 2973-76-4 ]
  • [ 2092-49-1 ]
Reference: [1] Nippon Kagaku Zasshi, 1956, vol. 77, p. 591,594[2] Chem.Abstr., 1958, p. 305
  • 61
  • [ 56-23-5 ]
  • [ 128-08-5 ]
  • [ 78-67-1 ]
  • [ 591-17-3 ]
  • [ 823-78-9 ]
Reference: [1] Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences, 1953, vol. <B> 56, p. 75,78
  • 62
  • [ 128-08-5 ]
  • [ 615-37-2 ]
  • [ 40400-13-3 ]
Reference: [1] Patent: US5180741, 1993, A,
  • 63
  • [ 128-08-5 ]
  • [ 140-39-6 ]
  • [ 34241-39-9 ]
  • [ 52727-95-4 ]
Reference: [1] Patent: US4645771, 1987, A,
  • 64
  • [ 128-08-5 ]
  • [ 201024-81-9 ]
  • [ 304-88-1 ]
  • [ 89539-42-4 ]
  • [ 89539-42-4 ]
Reference: [1] Tetrahedron, 1983, vol. 39, # 22, p. 3833 - 3842
  • 65
  • [ 128-08-5 ]
  • [ 77324-87-9 ]
  • [ 90725-68-1 ]
Reference: [1] Patent: EP514133, 1992, A1,
  • 66
  • [ 128-08-5 ]
  • [ 81245-24-1 ]
  • [ 74733-27-0 ]
Reference: [1] Patent: US4478849, 1984, A,
  • 67
  • [ 128-08-5 ]
  • [ 16419-60-6 ]
  • [ 91983-14-1 ]
Reference: [1] Russian Chemical Bulletin, 2005, vol. 54, # 11, p. 2602 - 2611
[2] Russian Chemical Bulletin, 2004, vol. 53, # 2, p. 370 - 375
  • 68
  • [ 128-08-5 ]
  • [ 5720-05-8 ]
  • [ 68162-47-0 ]
Reference: [1] Russian Chemical Bulletin, 2004, vol. 53, # 2, p. 370 - 375
  • 69
  • [ 128-08-5 ]
  • [ 17933-03-8 ]
  • [ 51323-43-4 ]
Reference: [1] Russian Chemical Bulletin, 2004, vol. 53, # 2, p. 370 - 375
  • 70
  • [ 128-08-5 ]
  • [ 13756-42-8 ]
  • [ 108052-76-2 ]
Reference: [1] Inorganic Chemistry, 2010, vol. 49, # 11, p. 5072 - 5078
  • 71
  • [ 128-08-5 ]
  • [ 492-97-7 ]
  • [ 3480-11-3 ]
Reference: [1] Patent: US2002/95041, 2002, A1,
[2] Patent: US5962490, 1999, A,
[3] Patent: US5594021, 1997, A,
  • 72
  • [ 128-08-5 ]
  • [ 367-30-6 ]
  • [ 112279-60-4 ]
Reference: [1] Patent: US5888421, 1999, A,
  • 73
  • [ 1468-83-3 ]
  • [ 128-08-5 ]
  • [ 59227-67-7 ]
Reference: [1] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1988, vol. 27, # 6, p. 538 - 539
  • 74
  • [ 128-08-5 ]
  • [ 105942-09-4 ]
Reference: [1] Patent: US5849736, 1998, A,
  • 75
  • [ 128-08-5 ]
  • [ 59382-59-1 ]
  • [ 98475-07-1 ]
Reference: [1] Patent: US2018/334443, 2018, A1,
  • 76
  • [ 128-08-5 ]
  • [ 195062-57-8 ]
  • [ 138500-85-3 ]
YieldReaction ConditionsOperation in experiment
76.1% With 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 14 h; Reflux P-toluene boronic acid pinacol ester (10.91 g, 50.0 mmol),Bromosuccinimide (NBS, 9.91 g, 55.0 mmol),Azobisisobutyronitrile (AIBN, 0.44 g, 2.0 mmol) was dissolved in dry carbon tetrachloride (CCl4, 200 mL).It was stirred at reflux for 14 hours, filtered, the solvent was removed by rotary evaporation, and the ethyl acetate (200 mL) was dissolved.After washing once with distilled water (100 mL) and saturated aqueous sodium chloride solution (100 mL), it was dried over anhydrous sodium sulfate.Spin-steaming, finally using petroleum ether as eluent to cross the column,4-Bromomethylphenylboronic acid pinacol ester (11.30 g, yield 76.1percent) was isolated.
Reference: [1] Patent: CN107417714, 2017, A, . Location in patent: Paragraph 0056; 0057; 0061
[2] Dalton Transactions, 2016, vol. 45, # 35, p. 13726 - 13741
  • 77
  • [ 128-08-5 ]
  • [ 75-18-3 ]
  • [ 222978-02-1 ]
  • [ 222978-03-2 ]
Reference: [1] Patent: US2003/220241, 2003, A1,
[2] Patent: US2003/220241, 2003, A1,
[3] Patent: US2003/220241, 2003, A1,
[4] Patent: US6358985, 2002, B1,
[5] Patent: US6297239, 2001, B1,
[6] Patent: US6316436, 2001, B1,
[7] Patent: US6284755, 2001, B1,
  • 78
  • [ 128-08-5 ]
  • [ 85070-67-3 ]
  • [ 222978-03-2 ]
Reference: [1] Patent: EP1955697, 2008, A1, . Location in patent: Page/Page column 16
  • 79
  • [ 128-08-5 ]
  • [ 195062-59-0 ]
  • [ 377780-72-8 ]
Reference: [1] Chemical Communications, 2017, vol. 53, # 14, p. 2218 - 2221
  • 80
  • [ 128-08-5 ]
  • [ 7424-72-8 ]
  • [ 474688-73-8 ]
Reference: [1] Patent: US2007/152565, 2007, A1,
  • 81
  • [ 128-08-5 ]
  • [ 79669-50-4 ]
  • [ 79670-17-0 ]
YieldReaction ConditionsOperation in experiment
70% With 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 4 h; Heating / reflux Place 5-bromo-2-methyl-benzoic acid (1.0 g, 4.7 mmol) in a 200 mL flask under an N2 atmosphere and add methanol via syringe. Add a 2M solution of diazomethyl- trimethyl-silane in hexane (3.5 mL, 23.0 mmol) drop wise over 10 minutes and stir for 1 hour at room temperature. Add glacial acetic acid (16 mL) and stir for 45 minutes. Dilute with ethyl acetate (100 mL) and wash with 1M aqueous sodium hydroxide solution (30 mL), saturated aqueous sodium bicarbonate solution (30 mL) and brine (30 mL). Dry the organic layer (Na2SO4), filter and concentrate in vacuo to obtain 1.01 g of 5-bromo-2- methyl-benzoic acid methyl ester (99 percent). Place 5-bromo-2-methyl-benzoic acid methyl ester (1.04 g, 4.5 mmol) in a 50 mL flask under a N2 atmosphere and add carbon tetrachloride (15 mL). Add N-bromo- succinamide (1.49 g, 8.3 mmol) and 2,2'-azobisisobutyronitrile (40 mg, 0.2 mmol) and fit flask with a condenser and reflux for 4 hours. Cool to room temperature and filter. Concentrate the filtrate and pre-adsorb the crude product onto silica gel. Chromatograph the residue on a Si02 column eluting with dichloromethane in hexane (0 to 50percent) to obtain 977 mg of 5-bromo-2-bromomethyl-benzoic acid methyl ester (70percent). Using 5-bromo-2-bromomethyl-benzoic acid methyl ester (0. 984 g, 3.20 mmol) and the procedure described in the I st paragraph for the alternative procedure for 5- (4,4, 5, 5-tetramethyl- [1, 3,2] dioxaborolan-2-yl) -2, 3-dihydro-isoindol-1-one, prepare 509 mg of the title compound (75 percent).
Reference: [1] Patent: WO2005/73205, 2005, A1, . Location in patent: Page/Page column 27-28
  • 82
  • [ 128-08-5 ]
  • [ 33332-28-4 ]
  • [ 173253-42-4 ]
Reference: [1] Patent: US6255307, 2001, B1,
  • 83
  • [ 128-08-5 ]
  • [ 2369-13-3 ]
  • [ 952664-69-6 ]
Reference: [1] Patent: US2012/15999, 2012, A1,
  • 84
  • [ 128-08-5 ]
  • [ 214360-70-0 ]
  • [ 942070-22-6 ]
YieldReaction ConditionsOperation in experiment
65% at 20℃; for 14 h; General procedure: To a solution of 3-anisyl pinacol borane (50 mg, 0.21 mmol)in DMF (1 mL) was added N-bromosuccinimide (82 mg, 0.46 mmol). After stirring at room temperature for 14 h, resultant solution was treated with 10percent Na2S2O3aq (10 ml) and was extracted with Et2O (10 ml3). The combined organic phase was washed with H2O (10 ml2) and brine (10 ml1) and dried over MgSO4. After removal of solvent under reduced pressure, the residue was chromatographed on silica gel with Hexane to afford 2-bromo-5-methoxyphenyl pinacol borate (57.3 mg, 87percent yield) as colorless oil
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 30, p. 4245 - 4247
  • 85
  • [ 128-08-5 ]
  • [ 6267-02-3 ]
  • [ 1333316-35-0 ]
Reference: [1] Patent: US2012/319052, 2012, A1,
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