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[ CAS No. 1940-57-4 ] {[proInfo.proName]}

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Chemical Structure| 1940-57-4
Chemical Structure| 1940-57-4
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Product Details of [ 1940-57-4 ]

CAS No. :1940-57-4 MDL No. :MFCD00001133
Formula : C13H9Br Boiling Point : -
Linear Structure Formula :- InChI Key :AHCDKANCCBEQJJ-UHFFFAOYSA-N
M.W : 245.12 Pubchem ID :16024
Synonyms :

Safety of [ 1940-57-4 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:1759
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1940-57-4 ]

* 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 [ 1940-57-4 ]
  • Downstream synthetic route of [ 1940-57-4 ]

[ 1940-57-4 ] Synthesis Path-Upstream   1~30

  • 1
  • [ 86-73-7 ]
  • [ 1133-80-8 ]
  • [ 1940-57-4 ]
YieldReaction ConditionsOperation in experiment
41 %Chromat. With N-Bromosuccinimide In acetonitrile at 20℃; for 19 h; General procedure: Reaction conditions: Thiourea (5.1 molpercent, 2 mg, 0.026 mmol) was added to an acetonitrile solution (10 mL) containing NBS (1.15 equiv, 104.4 mg, 0.587 mmol). Anisole (56.3 mg, 0.51 mmol) was added immediately to the resulting stirred solution and allowed to stir at room temperature for 10 min. The reaction was quenched by the addition of 10percent aqueous solution of Na2S2O3 (10 mL) and extracted with ethyl acetate (70 mL). The organic solution was then washed with additional 10percent Na2S2O3 (2 * 10 mL), followed by deionized water (3 * 15 mL) and brine (2 * 10 mL). The organic solution was then dried over anhydrous Na2SO4 and the solvent was evaporated in vacuo. The major product of each reaction was isolated by centrifugal thin-layer chromatography using a 2 mm thick silica gel 60GF254 coated plate (5percent CH2Cl2/hexanes). The products reported herein are known compounds and were characterised by GC-MS, IR, 1H and 13C NMR. Their spectroscopic data are in agreement with those reported in the literature.
Reference: [1] Tetrahedron, 2017, vol. 73, # 46, p. 6564 - 6572
  • 2
  • [ 1689-64-1 ]
  • [ 1940-57-4 ]
Reference: [1] Organic Letters, 2010, vol. 12, # 17, p. 3874 - 3877
[2] Journal of the Chemical Society, 1949, p. 2186
[3] Journal of Organic Chemistry, 1948, vol. 13, p. 339,342
[4] Chemische Berichte, 1925, vol. 58, p. 2230
[5] Journal of the Chemical Society, 1929, p. 2361
[6] Chemische Berichte, 1906, vol. 39, p. 3065
[7] Journal of Organic Chemistry, 1968, vol. 33, # 3, p. 1123 - 1127
[8] Synthesis, 1988, # 11, p. 902 - 904
[9] Chemische Berichte, 1910, vol. 43, p. 2492
[10] Chemische Berichte, 1926, vol. 59, p. 640
[11] Chemical Biology and Drug Design, 2018, vol. 91, # 6, p. 1078 - 1086
  • 3
  • [ 86-73-7 ]
  • [ 1940-57-4 ]
YieldReaction ConditionsOperation in experiment
96% With N-Bromosuccinimide; 1,1-bis(tert-butylperoxy)cyclohexane; nitric acid In dichloromethane at 20℃; for 1 h; Schlenk technique; Inert atmosphere The inventors selected the radical bromination of fluorene 27 by N- bromosuccinimide (NBS) at room temperature as a benchmark reaction to evaluate their inventive initiator system (Scheme 4). NBS (1.1 equiv.) (0075) Scheme 5: Room temperature Wohl-Ziegler bromination of fluorene. All reactions were performed according to the following procedure: In an oven- dried Schlenk flask fluorene 27 (83 mg, 0.5 mmol, 1 eq) and N-bromosuccinimide (98 mg, 0.55 mmol, 1 .1 eq) were dissolved in dichloromethane (5 ml). The desired peroxide (0.025 mmol, 5 mol percent) was introduced and the resulting mixture was degassed by the freeze-pump-thaw method (3 cycles). After warming to room temperature, the acid catalyst was added under a stream of argon and after the desired reaction time, the reaction mixture was quenched with NEt3 (250 μΙ_), CH2Br2 (0.5 mmol) was added as a standard for analytical purposes only and an aliquot taken for direct H NMR analysis. Yield was determined by integrating a reference peak of 28 (5.9 ppm, s, 1 H; determined from an authentic sample) relative to the peak of CH2Br2. The results of the reactions are detailed in (Table 1). The bromination proceeded efficiently using a commercial solution of peroxyketal 1 (Trigonox® 22, 50percent weight in mineral oil) in combination with different Bronsted acids. Control experiments confirmed the requirement for both acid and peroxide, no conversion being observed after 24 hours if either one of these components was omitted. A clear trend following the pKa value of the acid catalyst can be seen : stronger acids give faster conversion. Sulfuric and para-toluene sulfonic acid have similar behaviour with 72percent and 67percent of 28 after one hour, respectively (entries 1 and 2). Methane sulfonic acid gave a slightly lower yield (45percent; entry 3) while acids weaker than trifluoroacetic acid (22percent, entry 5) or trichloroacetic acid (1 8percent, entry 6) failed to give any conversion (entry 7). Nitric acid is more efficient than its pKa value would suggest (96percent; entry 4). Eventually, all reactions gave high yields when allowed to reach full conversion (80-95percent yield of 28 after 24 to 72 hours), showing that the acid catalyst only influences the initiation rate. Scandium (II I) triflate, a Lewis acid, was also found to be competent (69percent; entry 8). Different commercial peroxyketal solutions were evaluated using methane sulfonic acid as a standard catalyst of medium reactivity. 2 (Trigonox® D; 50percent weight) proved to be less efficient than 1 (45percent, entry 3), giving 1 0percent of product 28 after one hour and 76percent after 48 hours (entry 1 1 ). 3 (Trigonox® 301 ; 41 percent weight) showed low conversion after two days of reaction (8percent, entry 15). 4 (Luperox® DHD-9, 32percent weight) was found to be slightly more reactive than 3, giving 12percent product after 48 hours (entry 16). Based on the observation of this strong influence of the peroxyketal structure on its reactivity, the inventors evaluated a series of structurally different peroxides. The effect of the group X of Formula (I) is shown by compounds 11a and 11 b. 11 b proved to be less reactive than 1 (21 percent, entry 9) while 11a was more efficient, giving 47percent of 28 after one hour (entry 10). Aromatic substituents around the peroxide moiety can have significant effects: 5 is more effective than 2 (20percent, entry 12 compared to entry 1 1 ), while 6 was much less efficient (33percent after 48 h, entry 13) 9 was found to be slightly more reactive than 1 (50percent, entry 17) while 10 was the most efficient of the structures evaluated, giving 74percent of 28 after one hour of reaction (entry 18).
88% With tribromo-isocyanuric acid In ethyl acetate for 6 h; Reflux; Green chemistry General procedure: a solution of the arene (2.0 mmol) and TBCA (0.25 g, 0.68 mmol) in EtOAc (20 mL) was refluxed for 6 h with stirring. At the end of the reaction, the precipitated cyanuric acid was then separated by filtration and the filtrate was evaporated to dryness under reduced pressure. The residue was passed through a short chromatographic column (SiO2, eluted with 15:1 hexane–ethyl acetate) to give the purified products.
Reference: [1] Green Chemistry, 2011, vol. 13, # 4, p. 928 - 933
[2] Organic Letters, 2016, vol. 18, # 19, p. 4944 - 4947
[3] Patent: WO2017/108761, 2017, A1, . Location in patent: Page/Page column 15-18
[4] Advanced Synthesis and Catalysis, 2018, vol. 360, # 21, p. 4197 - 4204
[5] Tetrahedron Letters, 2015, vol. 56, # 49, p. 6843 - 6845
[6] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1986, vol. 25, p. 228 - 229
[7] Synthetic Communications, 1999, vol. 29, # 5, p. 763 - 766
[8] Chemische Berichte, 1948, vol. 81, p. 368,371
[9] Journal of Organic Chemistry, 1949, vol. 14, p. 470,472
[10] Journal of the American Chemical Society, 1947, vol. 69, p. 234
[11] Chemische Berichte, 1948, vol. 81, p. 368,371
[12] Journal of Organic Chemistry, 1949, vol. 14, p. 470,472
[13] Journal of the American Chemical Society, 1947, vol. 69, p. 234
[14] Chemische Berichte, 1948, vol. 81, p. 368,371
[15] Journal of Organic Chemistry, 1949, vol. 14, p. 470,472
[16] Journal of the American Chemical Society, 1947, vol. 69, p. 234
[17] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1948, vol. 226, p. 87
[18] Journal of the American Chemical Society, 1948, vol. 70, p. 895
[19] Justus Liebigs Annalen der Chemie, 1944, vol. 555, p. 133,137,144
[20] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1948, vol. 226, p. 87
[21] Journal of the American Chemical Society, 1948, vol. 70, p. 895
[22] Justus Liebigs Annalen der Chemie, 1944, vol. 555, p. 133,137,144
[23] Chemische Berichte, 1948, vol. 81, p. 368,371
[24] Journal of Organic Chemistry, 1949, vol. 14, p. 470,472
[25] Journal of the American Chemical Society, 1947, vol. 69, p. 234
[26] Journal of the Chemical Society, 1961, p. 1291 - 1297
[27] Journal of the American Chemical Society, 1962, vol. 84, p. 3959 - 3962
[28] Tetrahedron Letters, 1984, vol. 25, # 31, p. 3369 - 3372
[29] Chemical Papers, 2013, vol. 67, # 7, p. 751 - 758
[30] Journal of Fluorescence, 2014, vol. 24, # 2, p. 523 - 531
[31] Journal of the Chinese Chemical Society, 2016, vol. 63, # 4, p. 368 - 375
  • 4
  • [ 86-73-7 ]
  • [ 1133-80-8 ]
  • [ 1940-57-4 ]
YieldReaction ConditionsOperation in experiment
41 %Chromat. With N-Bromosuccinimide In acetonitrile at 20℃; for 19 h; General procedure: Reaction conditions: Thiourea (5.1 molpercent, 2 mg, 0.026 mmol) was added to an acetonitrile solution (10 mL) containing NBS (1.15 equiv, 104.4 mg, 0.587 mmol). Anisole (56.3 mg, 0.51 mmol) was added immediately to the resulting stirred solution and allowed to stir at room temperature for 10 min. The reaction was quenched by the addition of 10percent aqueous solution of Na2S2O3 (10 mL) and extracted with ethyl acetate (70 mL). The organic solution was then washed with additional 10percent Na2S2O3 (2 * 10 mL), followed by deionized water (3 * 15 mL) and brine (2 * 10 mL). The organic solution was then dried over anhydrous Na2SO4 and the solvent was evaporated in vacuo. The major product of each reaction was isolated by centrifugal thin-layer chromatography using a 2 mm thick silica gel 60GF254 coated plate (5percent CH2Cl2/hexanes). The products reported herein are known compounds and were characterised by GC-MS, IR, 1H and 13C NMR. Their spectroscopic data are in agreement with those reported in the literature.
Reference: [1] Tetrahedron, 2017, vol. 73, # 46, p. 6564 - 6572
  • 5
  • [ 1989-33-9 ]
  • [ 1940-57-4 ]
Reference: [1] Journal of the American Chemical Society, 1975, vol. 97, # 9, p. 2438 - 2449
  • 6
  • [ 486-25-9 ]
  • [ 1940-57-4 ]
Reference: [1] Dyes and Pigments, 2013, vol. 96, # 3, p. 642 - 652
[2] Chemical Biology and Drug Design, 2018, vol. 91, # 6, p. 1078 - 1086
  • 7
  • [ 506-96-7 ]
  • [ 1689-64-1 ]
  • [ 1940-57-4 ]
Reference: [1] Journal of the American Chemical Society, 1933, vol. 55, p. 2135,2136
[2] Journal of the American Chemical Society, 1940, vol. 62, p. 2687,2689
  • 8
  • [ 31859-93-5 ]
  • [ 1940-57-4 ]
Reference: [1] Chemische Berichte, 1910, vol. 43, p. 2492
[2] , 1967, vol. 3, p. 677 - 679[3] Zhurnal Organicheskoi Khimii, 1967, vol. 3, # 4, p. 709 - 711
  • 9
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Reference: [1] Chemische Berichte, 1910, vol. 43, p. 2492
  • 10
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Reference: [1] Chemische Berichte, 1926, vol. 59, p. 640
  • 11
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Reference: [1] , 1967, vol. 3, p. 677 - 679[2] Zhurnal Organicheskoi Khimii, 1967, vol. 3, # 4, p. 709 - 711
  • 12
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Reference: [1] Chemische Berichte, 1948, vol. 81, p. 368,371
  • 13
  • [ 86-73-7 ]
  • [ 77-48-5 ]
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Reference: [1] Anales de la Asociacion Quimica Argentina (1921-2001), 1949, vol. 37, p. 263,266[2] Anales de la Asociacion Quimica Argentina (1921-2001), 1950, vol. 38, p. 5,10
  • 14
  • [ 861373-58-2 ]
  • [ 467-69-6 ]
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Reference: [1] Chemische Berichte, 1926, vol. 59, p. 640
  • 15
  • [ 86-73-7 ]
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Reference: [1] Anales de la Asociacion Quimica Argentina (1921-2001), 1949, vol. 37, p. 263,266[2] Anales de la Asociacion Quimica Argentina (1921-2001), 1950, vol. 38, p. 5,10
  • 16
  • [ 56-23-5 ]
  • [ 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
  • 17
  • [ 75-15-0 ]
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Reference: [1] Chemische Berichte, 1948, vol. 81, p. 368,371
[2] Journal of the American Chemical Society, 1947, vol. 69, p. 234
  • 18
  • [ 56-23-5 ]
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Reference: [1] Chemische Berichte, 1948, vol. 81, p. 368,371
[2] Journal of the American Chemical Society, 1947, vol. 69, p. 234
  • 19
  • [ 86-73-7 ]
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Reference: [1] Chemische Berichte, 1948, vol. 81, p. 368,371
[2] Journal of the American Chemical Society, 1947, vol. 69, p. 234
  • 20
  • [ 128-08-5 ]
  • [ 86-73-7 ]
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  • [ 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
  • 21
  • [ 1689-64-1 ]
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Reference: [1] Journal of Organic Chemistry, 1948, vol. 13, p. 339,342
  • 22
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Reference: [1] Journal of Organic Chemistry, 1948, vol. 13, p. 339,342
  • 23
  • [ 56-23-5 ]
  • [ 86-73-7 ]
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Reference: [1] Chemische Berichte, 1948, vol. 81, p. 368,371
  • 24
  • [ 31859-93-5 ]
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Reference: [1] Chemische Berichte, 1910, vol. 43, p. 2492
  • 25
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Reference: [1] Chemische Berichte, 1926, vol. 59, p. 640
  • 26
  • [ 861373-58-2 ]
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Reference: [1] Chemische Berichte, 1926, vol. 59, p. 640
  • 27
  • [ 10035-10-6 ]
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Reference: [1] Chemische Berichte, 1926, vol. 59, p. 640
  • 28
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  • [ 108-89-4 ]
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Reference: [1] Zeitschrift fuer Chemie (Stuttgart, Germany), 1985, vol. 25, # 12, p. 438
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  • [ 119-65-3 ]
  • [ 486-25-9 ]
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Reference: [1] Zeitschrift fuer Chemie (Stuttgart, Germany), 1985, vol. 25, # 12, p. 438
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Reference: [1] Zeitschrift fuer Chemie (Stuttgart, Germany), 1985, vol. 25, # 12, p. 438
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