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[ CAS No. 2969-81-5 ]

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Chemical Structure| 2969-81-5
Chemical Structure| 2969-81-5
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CAS No. :2969-81-5 MDL No. :MFCD00000259
Formula : C6H11BrO2 Boiling Point : 198.3°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :195.05 g/mol Pubchem ID :76300
Synonyms :

Safety of [ 2969-81-5 ]

Signal Word:Danger Class:8
Precautionary Statements:P210-P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P370+P378-P403+P233-P403+P235-P405-P501 UN#:1760
Hazard Statements:H227-H315-H318-H335 Packing Group:
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Application In Synthesis of [ 2969-81-5 ]

  • Upstream synthesis route of [ 2969-81-5 ]
  • Downstream synthetic route of [ 2969-81-5 ]

[ 2969-81-5 ] Synthesis Path-Upstream   1~31

  • 1
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  • [ 50998-74-8 ]
  • [ 24310-36-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 19, p. 8670 - 8692
  • 2
  • [ 67-56-1 ]
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  • [ 4897-84-1 ]
Reference: [1] Angewandte Chemie - International Edition, 2001, vol. 40, # 19, p. 3672 - 3674
  • 3
  • [ 554-12-1 ]
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  • [ 4897-84-1 ]
Reference: [1] Helvetica Chimica Acta, 1982, vol. 65, # 4, p. 1197 - 1201
  • 4
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  • [ 2623-87-2 ]
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Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 2, p. 608 - 626
[2] U.S.Atomic Energy Comm.WADC-TR-56-540 <1957>25,
[3] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1886, vol. 102, p. 369[4] Bulletin de la Societe Chimique de France, 1886, vol. <2>46, p. 65
[5] Journal of the Chemical Society, 1937, p. 1977
[6] Journal of the American Chemical Society, 1933, vol. 55, p. 1233 - 1241
[7] ACS Chemical Neuroscience, 2017, vol. 8, # 9, p. 1949 - 1959
  • 5
  • [ 64-17-5 ]
  • [ 927-58-2 ]
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Reference: [1] Journal of the Chemical Society, 1950, p. 1474,1476
[2] Patent: EP1953148, 2008, A1, . Location in patent: Page/Page column 122
  • 6
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YieldReaction ConditionsOperation in experiment
85.5% With hydrogenchloride In 1,4-dioxane; ethanol; dichloromethane Part A
Preparation of ethyl 4-bromobutyrate
To a solution of 4-bromobutyric acid (3 g, 18 mmol) in ethanol (30 mL) was added 5 mL of 4N HCl in dioxane.
The reaction mixture was stirred for 16 hours at room temperature, and then the volatile components were removed under vacuum.
The concentrated residue was brought up in 150 mL of methylene chloride.
The organic solution was washed with saturated aqueous NaHCO3 (1 x 150 mL), brine (1*150 mL), dried over MgSO4, filtered, and the filtrate was concentrated at reduced pressure.
The concentrated residue was dried in vacuo to give 3 g (85.5percent) of the known product as a yellow oil. 1 H NMR (300 MHz/CDCl3): δ 1.22 (t, 3H, J=7.15 Hz), 2.13 (overlapping t, 2H, J=6.80 Hz), 2.45 (t, 2H, J=7.15 Hz), 3.43 (t, 2H, J=6.44 Hz), 4.10 (q, 2H, J=7.25 Hz).
Reference: [1] Patent: US5753660, 1998, A,
  • 7
  • [ 96-48-0 ]
  • [ 64-17-5 ]
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 336 - 343
[2] Journal of the American Chemical Society, 1952, vol. 74, p. 4960
[3] Journal of the Chemical Society, 1958, p. 3377,3382
[4] Journal of the Chemical Society, 1957, p. 2312
[5] Journal of the Chemical Society, 1953, p. 3502
[6] Org.Synth.Coll.Vol. V <1973>545,
[7] U.S.Atomic Energy Comm.WADC-TR-56-540 <1957>25,
[8] Journal of Organic Chemistry, 1951, vol. 16, p. 1417,1418
[9] Tetrahedron, 1960, vol. 11, p. 154 - 157
[10] Journal of pharmaceutical sciences, 1972, vol. 61, # 12, p. 1936 - 1940
[11] The Journal of organic chemistry, 1972, vol. 37, # 26, p. 4396 - 4399
  • 8
  • [ 1191-95-3 ]
  • [ 1801-77-0 ]
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Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 6, p. 2264 - 2266
  • 9
  • [ 64-17-5 ]
  • [ 5332-06-9 ]
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Reference: [1] Journal of the American Chemical Society, 1956, vol. 78, p. 4030
[2] U.S.Atomic Energy Comm.WADC-TR-56-540 <1957>25,
  • 10
  • [ 58258-01-8 ]
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  • [ 125602-76-8 ]
Reference: [1] Patent: US4929618, 1990, A,
  • 11
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Reference: [1] Patent: US4929618, 1990, A,
  • 12
  • [ 88535-96-0 ]
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Reference: [1] Patent: US4929618, 1990, A,
  • 13
  • [ 125603-01-2 ]
  • [ 125602-78-0 ]
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Reference: [1] Patent: US4929618, 1990, A,
  • 14
  • [ 125603-04-5 ]
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Reference: [1] Patent: US4929618, 1990, A,
  • 15
  • [ 999-10-0 ]
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Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 9, p. 3874 - 3883
  • 16
  • [ 1617-18-1 ]
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Reference:
  • 17
  • [ 64-17-5 ]
  • [ 56489-06-6 ]
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Reference: [1] Collection of Czechoslovak Chemical Communications, 1956, vol. 21, p. 1602,1605
  • 18
  • [ 36847-51-5 ]
  • [ 2969-81-5 ]
  • [ 4606-07-9 ]
  • [ 105-54-4 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1983, # 11, p. 2401 - 2416
  • 19
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  • [ 10035-10-6 ]
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Reference:
  • 20
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  • [ 7425-53-8 ]
YieldReaction ConditionsOperation in experiment
87% With potassium iodide In acetone for 12 h; Reflux In a 100 ml round bottom flask, ethyl4-bromobutyrate (6.0 ml, 40.2 mmol: 1H NMR (300 MHz, CDCl3) δ 4.14(q, J = 7.2 Hz, 2H), 3.47 (t, J = 6.5 Hz, 2H), 2.49 (t, J = 7.2 Hz, 2H), 2.17(m, 2H), 1.26 (t, J = 7.1 Hz, 3H).) was dissolved in 40 ml acetone. Potassium iodide (13.35 g, 80.4 mmol,2.0 equiv.) was added, a reflux condenser was attached, and the reaction was heated at reflux for 12h. Thesolution was cooled, filtered through a course fritted funnel, and concentrated in vacuo. The resultingyellow oil with fine particulates was taken up in ca 50 ml of 1:1 Hex:Et2O and filtered through neutralaluminum to remove color. After flushing with an additional 100 ml 1:1 Hex:Et2O, the solution wasconcentrated to yield 8.44 g (87percent) of ethyl 4-iodobutyrate 12. 1H NMR (300 MHz, CDCl3) δ 4.14 (q, J =7.2 Hz, 2H), 3.24 (t, J = 6.8 Hz, 2H), 2.44 (t, J = 7.1 Hz, 2H), 2.13 (m, 2H), 1.26 (t, J = 7.2 Hz, 3H). A 50ml Schlenk flask was flame dried under vacuum, cooled to 23 °C, and charged with ethyl 4-iodobutyrate(8.4 g, 34.7 mmol) and copper(I) iodide (10 mg, 0.05 mmol). After sealing with a greased ground glassstopper, the flask was evacuated and refilled with Ar. The stopper was replaced with a rubber septum andneat diethyl zinc (14 ml, 137 mmol, 4 equiv) was added via syringe. The reaction was heated at 40 °C for12 h. The excess diethyl zinc and ethyl iodide were removed under vacuum for 2 h into a trap withmethanol cooled to -78 °C with dry ice and acetone. (CAUTION: A trap cooled with liquid nitrogeneasily clogs so dry ice/acetone cooling is preferred. Methanol quenches the excess diethyl zinc, but careshould be taken when cleaning the trap as some diethyl zinc may remain.) After backfilling with Ar, THF(5 ml) was added to the reaction vessel and heated at 40 °C for 1 h under Ar. The reaction vessel wasevacuated for 1 h. This step was repeated another two times. After cooling to 23 °C, the generated bis(4-ethoxy-4-oxobutyl)zinc was diluted with 15 ml of THF and this solution was used directly in thedesymmetrization reaction.
Reference: [1] Synthetic Communications, 2009, vol. 39, # 1, p. 61 - 69
[2] Journal of Organic Chemistry, 2004, vol. 69, # 9, p. 3025 - 3035
[3] Advanced Synthesis and Catalysis, 2007, vol. 349, # 8-9, p. 1533 - 1536
[4] Journal of Organic Chemistry, 2007, vol. 72, # 18, p. 6816 - 6823
[5] Synthesis (Germany), 2018, vol. 50, # 22, p. 4343 - 4350
[6] Tetrahedron, 1996, vol. 52, # 45, p. 14081 - 14102
[7] Journal of the American Chemical Society, 2016, vol. 138, # 24, p. 7528 - 7531
[8] Tetrahedron, 1960, vol. 11, p. 154 - 157
[9] Journal of Organic Chemistry, 1989, vol. 54, # 4, p. 890 - 896
[10] Tetrahedron Letters, 1987, vol. 28, # 37, p. 4243 - 4246
[11] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985, p. 2677 - 2688
[12] Tetrahedron, 1999, vol. 55, # 18, p. 5741 - 5758
[13] Journal of the American Chemical Society, 2000, vol. 122, # 40, p. 9600 - 9609
[14] Synthetic Communications, 2009, vol. 39, # 9, p. 1690 - 1690
[15] Patent: EP1612201, 2006, A1, . Location in patent: Page/Page column 26-28
[16] Advanced Synthesis and Catalysis, 2012, vol. 354, # 13, p. 2521 - 2530,10
[17] Advanced Synthesis and Catalysis, 2012, vol. 354, # 13, p. 2521 - 2530
  • 21
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Reference: [1] Journal of Organic Chemistry, 2002, vol. 67, # 1, p. 79 - 85
  • 22
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  • [ 124-38-9 ]
  • [ 1070-62-8 ]
Reference: [1] Organic Letters, 2009, vol. 11, # 9, p. 2035 - 2037
  • 23
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  • [ 17049-50-2 ]
  • [ 124-06-1 ]
Reference: [1] Advanced Synthesis and Catalysis, 2008, vol. 350, # 10, p. 1484 - 1488
  • 24
  • [ 2969-81-5 ]
  • [ 541-41-3 ]
  • [ 818-38-2 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 3, p. 788 - 790
  • 25
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  • [ 26496-94-6 ]
Reference: [1] Patent: US4804658, 1989, A,
  • 26
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  • [ 106-48-9 ]
  • [ 59227-79-1 ]
YieldReaction ConditionsOperation in experiment
92% With potassium carbonate In acetonitrile for 8 h; Reflux To a solution of 4-chlorophenol (2.0 g, 15.556 mmol, 1 equiv) in acetonitrile (60 mL) was added anhydrous potassium carbonate (4.3 g, 31 .1 13 mmol, 2 equiv) and ethyl 4-bromobutanoate (3.56 mL, 24.891 mmol, 1 .6 equiv). The reaction mixture was heated to reflux and stirred for 8 h. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mixture was allowed to cool to 27 °C, filtered the solid and washed with ethyl acetate (100 mL). The filtrate was concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography using 10percent ethyl acetate in hexane as eluent to obtain the title compound ethyl 4-(4-chlorophenoxy)butanoate (3.5 g, 92 percent yield) as colourless liquid. LCMS (ES) m/z = 242.9 [M+H]+. NMR (400 MHz, CDCI3): δ ppm 1 .25 (t, J = 6.8 Hz, 3 H), 2.06 - 2.06 (m, 2 H), 2.49 (t, J = 6.8 Hz, 2 H), 3.97 (t, J = 6.0 Hz, 2 H), 4.1 1 - 4.17 (m, 2 H), 6.80 (d, J = 8.4 Hz, 2 H), 7.21 (d, J = 8.8 Hz, 2 H).
89% With potassium carbonate In N,N-dimethyl-formamide at 140℃; for 4 h; To a solution of 4-chlorophenol (10 g, 77.784 mmol, 1 equiv) in N,N- dimethylformamide (100 mL) was added anhydrous potassium carbonate (21 .5 g, 1 16.6 mmol, 2 equiv) and ethyl 4-bromobutanoate (16.7 mL, 1 16.677 mmol, 1 .5 equiv). The reaction mixture was heated to 140 °C and stirred for 4 h. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mixture was allowed to cool to 27 °C, filtered the solid and washed with ethyl acetate (700 mL). The filtrate was washed with water (2 x 200 mL), brine solution (100 mL), dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography using 10 percent ethyl acetate in hexane as eluent to obtain ethyl 4-(4-chlorophenoxy)butanoate (17.0 g, 89 percent yield) as white solid. LCMS (ES) m/z = 243.1 [M+H]+. NMR (400 MHz, CDCI3): δ ppm 1 .25 (t, J = 7.2 Hz, 3 H), 2.06 - 2.12 (m, 2 H), 2.49 (t, J = 7.6 Hz, 2 H), 3.97 (t, J = 6.0 Hz, 2 H), 4.1 1 - 4.17 (m, 2 H), 6.80 (d, J = 8.8 Hz, 2 H), 7.21 (d, J = 8.8 Hz, 2 H).
83% With potassium carbonate In acetoneReflux General procedure: General synthetic procedure for phenoxy acetic/butyric acid ethyl ester derivatives (3a-l) A mixture of substituted phenols 1a-f (0.05 mol) and 2a-b (0.075 mol) in dry acetone (40 ml) with anhydrous potassium carbonate (0.075 mol) were refluxed for 8-10 h. The reaction mixture was cooled and solvent removed by distillation. The residual mass was triturated with cold water to remove potassium carbonate, and extracted with ether (3 * 30 ml). The ether layer was washed with 10percent sodium hydroxide solution (3 * 30 ml) followed by water (3 * 30 ml) and then dried over anhydrous sodium sulfate and evaporated to afford compounds 3a-l. 4-(4-Chloro-phenoxy)-butyric acid ethyl ester (3b)
Yield 83percent; FT-IR (cm-1): 1738 (C=O), 1281 (C-O-C); 1H NMR (CDCl3): δ 1.35 (t, 3H, CH3 of ester), 2.26 (m, 2H, CH2), 2.75 (t, 2H, COCH2), 4.07 (t, 2H, OCH2), 4.31 (q, 2H, CH2 of ester), 6.88 (d, J = 8.80 Hz, 2H, Ar-H), 7.27 (d, J = 8.85 Hz, 2H, Ar-H); LC-MS m/z 243 (M + 1). Anal. Calcd. for C12H15ClO3: C, 59.39; H, 6.23. Found: C, 59.50; H, 6.16percent.
Reference: [1] Patent: WO2017/212425, 2017, A1, . Location in patent: Page/Page column 112
[2] Patent: WO2017/212423, 2017, A1, . Location in patent: Page/Page column 126
[3] Bioorganic Chemistry, 2015, vol. 60, p. 136 - 146
[4] Journal of Agricultural and Food Chemistry, 2016, vol. 64, # 37, p. 6911 - 6915
[5] Indian Journal of Heterocyclic Chemistry, 2018, vol. 28, # 3, p. 379 - 384
  • 27
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  • [ 2969-81-5 ]
  • [ 19999-64-5 ]
Reference: [1] Patent: US5102890, 1992, A,
  • 28
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  • [ 52763-21-0 ]
Reference: [1] Organic Process Research and Development, 2003, vol. 7, # 3, p. 418 - 425
  • 29
  • [ 106-41-2 ]
  • [ 2969-81-5 ]
  • [ 55580-08-0 ]
Reference: [1] Patent: US6166006, 2000, A,
  • 30
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  • [ 157245-87-9 ]
YieldReaction ConditionsOperation in experiment
81% With potassium carbonate In acetoneReflux General procedure: General synthetic procedure for phenoxy acetic/butyric acid ethyl ester derivatives (3a-l) A mixture of substituted phenols 1a-f (0.05 mol) and 2a-b (0.075 mol) in dry acetone (40 ml) with anhydrous potassium carbonate (0.075 mol) were refluxed for 8-10 h. The reaction mixture was cooled and solvent removed by distillation. The residual mass was triturated with cold water to remove potassium carbonate, and extracted with ether (3 * 30 ml). The ether layer was washed with 10percent sodium hydroxide solution (3 * 30 ml) followed by water (3 * 30 ml) and then dried over anhydrous sodium sulfate and evaporated to afford compounds 3a-l. 4-(4-Bromo-phenoxy)-butyric acid ethyl ester (3d)
Yield 81percent; FT-IR (cm-1): 1733 (C=O), 1287 (C-O-C); 1H NMR (CDCl3): δ 1.34 (t, 3H, CH3 of ester), 2.26 (m, 2H, CH2), 2.72 (t, 2H, COCH2), 4.05 (t, 2H, OCH2), 4.31 (q, 2H, CH2 of ester), 6.83 (d, J = 8.80 Hz, 2H, Ar-H), 7.35 (d, J = 8.85 Hz, 2H, Ar-H); LC-MS m/z 288 (M + 1). Anal. Calcd. for C12H15BrO3: C, 50.19; H, 5.27. Found: C, 50.29; H, 5.18percent.
Reference: [1] Bioorganic Chemistry, 2015, vol. 60, p. 136 - 146
[2] Journal of Medicinal Chemistry, 2000, vol. 43, # 10, p. 2049 - 2063
[3] Patent: WO2016/25932, 2016, A1, . Location in patent: Page/Page column 150
[4] Chemistry - A European Journal, 2016, vol. 22, # 29, p. 9971 - 9974
[5] Indian Journal of Heterocyclic Chemistry, 2018, vol. 28, # 3, p. 379 - 384
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  • [ 95-01-2 ]
  • [ 152942-06-8 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 44, p. 15114 - 15123
[2] Organic letters, 2000, vol. 2, # 13, p. 1787 - 1790
[3] Patent: US5994378, 1999, A,
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