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[ CAS No. 28920-43-6 ]

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Chemical Structure| 28920-43-6
Chemical Structure| 28920-43-6
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CAS No. :28920-43-6 MDL No. :MFCD00001138
Formula : C15H11ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :258.70 g/mol Pubchem ID :34367
Synonyms :

Safety of [ 28920-43-6 ]

Signal Word:Danger Class:8,6.1
Precautionary Statements:P260-P261-P264-P270-P271-P280-P301+P312-P301+P330+P331-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P310-P312-P321-P322-P330-P363-P405-P501 UN#:2923
Hazard Statements:H301-H312-H314-H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 28920-43-6 ]

  • Upstream synthesis route of [ 28920-43-6 ]
  • Downstream synthetic route of [ 28920-43-6 ]

[ 28920-43-6 ] Synthesis Path-Upstream   1~27

  • 1
  • [ 1208119-52-1 ]
  • [ 28920-43-6 ]
  • [ 103478-62-2 ]
Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 5, p. 1386 - 1392
  • 2
  • [ 449806-69-3 ]
  • [ 186581-53-3 ]
  • [ 28920-43-6 ]
  • [ 103478-62-2 ]
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 10, p. 3723 - 3728
  • 3
  • [ 56-86-0 ]
  • [ 28920-43-6 ]
  • [ 104091-09-0 ]
Reference: [1] Journal of the Chinese Chemical Society, 2011, vol. 58, # 4, p. 509 - 515
[2] Soft Matter, 2011, vol. 7, # 19, p. 8913 - 8922
  • 4
  • [ 28920-43-6 ]
  • [ 104091-09-0 ]
Reference: [1] Synlett, 2011, # 14, p. 2013 - 2016
  • 5
  • [ 28920-43-6 ]
  • [ 3105-95-1 ]
  • [ 101555-63-9 ]
YieldReaction ConditionsOperation in experiment
1.41 g With sodium carbonate In 1,4-dioxane; water at 0 - 20℃; for 16 h; To a stirred mixture of (S)-piperidine-2-carboxylic acid (1.0 g, 7.75 mmol) and Na2C03 (1.65 g, 15.50 mmol) in water (10 mL) was added a solution of FMOC-C1 (3.0 g, 11.63 mmol) in 1,4-dioxane (10 mL) dropwise at 0°C and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with water (50 mL) and washed with MTBE (25 mL). The aqueous layer was acidified with 1M aqueous HC1 (10 mL) to pH 2 and extracted with EtOAc (3 x 50 mL). The combined organic extracts were washed with brine solution (50 mL), dried over anhydrous a2S04, filtered and concentrated to afford the title compound (1.41 g) as an off-white solid. The crude product was used in the next step without purification
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 4, p. 1111 - 1115
[2] Journal of the American Chemical Society, 2006, vol. 128, # 11, p. 3838 - 3847
[3] Patent: WO2013/148478, 2013, A1, . Location in patent: Page/Page column 23
  • 6
  • [ 28920-43-6 ]
  • [ 15912-30-8 ]
  • [ 101555-63-9 ]
Reference: [1] Journal of Organic Chemistry, 1992, vol. 57, # 16, p. 4394 - 4400
  • 7
  • [ 28920-43-6 ]
  • [ 25691-37-6 ]
  • [ 117106-21-5 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 14, p. 4347 - 4354
  • 8
  • [ 28920-43-6 ]
  • [ 109425-55-0 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2001, vol. 49, # 9, p. 1189 - 1191
  • 9
  • [ 28920-43-6 ]
  • [ 109425-55-0 ]
Reference: [1] Protein and Peptide Letters, 2010, vol. 17, # 7, p. 889 - 898
  • 10
  • [ 42417-72-1 ]
  • [ 28920-43-6 ]
  • [ 117106-20-4 ]
Reference: [1] Tetrahedron, 1988, vol. 44, # 6, p. 1773 - 1782
  • 11
  • [ 28920-43-6 ]
  • [ 13030-09-6 ]
  • [ 122350-52-1 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 9, p. 2707 - 2710
  • 12
  • [ 28920-43-6 ]
  • [ 35146-32-8 ]
  • [ 109425-51-6 ]
Reference: [1] Liebigs Annalen der Chemie, 1987, p. 1025 - 1030
  • 13
  • [ 1208119-51-0 ]
  • [ 28920-43-6 ]
  • [ 103478-58-6 ]
Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 5, p. 1386 - 1392
  • 14
  • [ 186581-53-3 ]
  • [ 28920-43-6 ]
  • [ 270073-00-2 ]
  • [ 103478-58-6 ]
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 10, p. 3723 - 3728
  • 15
  • [ 67-56-1 ]
  • [ 72-18-4 ]
  • [ 28920-43-6 ]
  • [ 103478-58-6 ]
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 42, p. 7307 - 7310
  • 16
  • [ 28920-43-6 ]
  • [ 30845-10-4 ]
  • [ 102971-73-3 ]
YieldReaction ConditionsOperation in experiment
15% With sodium carbonate In tetrahydrofuran The compound 2 (2g, 7.60mmol) was dissolved in 10percent Na2CO3, and the Fmoc-Cl (2.94g, 11.4mmol) was added slowly, which was mixed with THF (7mL). After stirring overnight, 10percent citric acid was added to adjust PH 4 ~ 5. The THF was removed under reduced pressure and the residual solution was extracted by CH2Cl2. After washing successively with saturated NaCl solution, the organic phase was dried over anhydrous Na2SO4 and concentrated, the residue was purified by silica gel column chromatography (550mg, 15percent). 1H NMR (400 MHz, DMSO-d6 ) δ 7.85 (d, J = 7.5 Hz, 2H), 7.77 ~7.61 (m, 3H), 7.37 (t, J = 7.5 Hz, 2H), 7.28 (t, J =7.4 Hz, 2H), 4.32~4.14 (m, 3H), 4.08 (qd, J = 8.8, 4.6 Hz, 1H), 2.86 (dt, J = 24.4, 10.2 Hz, 1H), 2.70(ddd, J = 15.2, 9.6, 5.6 Hz, 1H), 2.55 ~ 2.41 (m, 2H), 2.23 (t, J = 7.3 Hz, 2H), 1.68 (dd, J = 8.4, 6.1 Hz, 2H), 1.33 (s, 9H). 13C-NMR (100 MHz, DMSO-d6 ): δ172.86, 172.31, 156.54, 144.32, 141.26, 141.24, 128.17, 127.59, 125.84, 125.80, 120.64, 80.13, 66.26, 54.58, 47.14, 34.11, 33.05, 33.04, 31.15, 28.24, 25.03.
10% With sodium carbonate In tetrahydrofuran at 20℃; Preparation of Compound 21: Compound 4 (2 g, 7.6 mmol) was dissolved with 10 ml of 10percent Na 2 CO 3 solution, Fmoc-Cl (2.94 g, 11.4 mmol) dissolved in THF was added, reacted overnight at room temperature, and the pH was adjusted with 10percent citric acid. 5, THF was removed under reduced pressure, extracted with CH2Cl2, the organic phase was washed with saturated NaCl solution, and dried under reduced pressure to give a brown yellow oil product 21 (200 mg, yield: 10percent);
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 14, p. 2375 - 2378
[2] Patent: CN107628975, 2018, A, . Location in patent: Paragraph 0142; 0143; 0144; 0145; 0146; 0147
  • 17
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  • [ 25840-83-9 ]
  • [ 111061-56-4 ]
Reference: [1] Liebigs Annalen der Chemie, 1987, p. 1025 - 1030
  • 18
  • [ 28920-43-6 ]
  • [ 45125-00-6 ]
  • [ 104091-08-9 ]
Reference: [1] Journal of Organic Chemistry, 1986, vol. 51, # 24, p. 4590 - 4594
  • 19
  • [ 28920-43-6 ]
  • [ 106719-44-2 ]
  • [ 115186-31-7 ]
Reference: [1] Tetrahedron, 2002, vol. 58, # 27, p. 5427 - 5439
  • 20
  • [ 28920-43-6 ]
  • [ 52-52-8 ]
  • [ 117322-30-2 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 2001, vol. 40, # 1, p. 70 - 74
  • 21
  • [ 28920-43-6 ]
  • [ 141-43-5 ]
  • [ 105496-31-9 ]
YieldReaction ConditionsOperation in experiment
87% at 20℃; for 0.0333333 h; Sonication; Irradiation; Green chemistry General procedure: Amine (1 mmol) and Fmoc-Cl (1.1 mmol) were placed in a glass tube under neat conditions and were sonicated for a suitable time (as indicated in Tables 1, 2 and 3). All reactions were performed in a water bath at room temperature. After completion of the reaction (as indicated by TLC), 5 cm3 of diethyl ether was added to the mixture. The N-Fmoc derivatives were crystallized and were obtained in good to excellent yields. Purification of the product was accomplished by recrystallization from diethyl ether.
Reference: [1] Nucleosides and Nucleotides, 1994, vol. 13, # 1-3, p. 255 - 273
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 2, p. 871 - 882
[3] Journal of Carbohydrate Chemistry, 2012, vol. 31, # 4-6, p. 384 - 419
[4] Russian Journal of Bioorganic Chemistry, 2005, vol. 31, # 4, p. 352 - 356
[5] European Journal of Organic Chemistry, 2008, # 34, p. 5786 - 5797
[6] Green Chemistry, 2011, vol. 13, # 12, p. 3355 - 3359
[7] Journal of the Brazilian Chemical Society, 2016, vol. 27, # 3, p. 546 - 550
[8] Chemical Communications, 2014, vol. 50, # 54, p. 7132 - 7135
[9] Patent: WO2018/149419, 2018, A1, . Location in patent: Paragraph 001283
[10] Tetrahedron Letters, 1993, vol. 34, # 39, p. 6189 - 6192
[11] Tetrahedron Letters, 2002, vol. 43, # 17, p. 3125 - 3128
[12] Patent: US2006/51291, 2006, A1, . Location in patent: Page/Page column 7; 24
[13] Patent: US5599587, 1997, A,
[14] Patent: WO2006/39668, 2006, A2, . Location in patent: Page/Page column 40
[15] Patent: WO2006/105123, 2006, A2, . Location in patent: Page/Page column 50
  • 22
  • [ 28920-43-6 ]
  • [ 56-12-2 ]
  • [ 116821-47-7 ]
Reference: [1] Chemistry - A European Journal, 1998, vol. 4, # 3, p. 425 - 433
[2] Tetrahedron Letters, 1998, vol. 39, # 28, p. 5117 - 5120
[3] Bioorganic Chemistry, 1996, vol. 24, # 1, p. 50 - 58
[4] Tetrahedron Letters, 2004, vol. 45, # 19, p. 3703 - 3706
[5] Patent: US2003/143591, 2003, A1,
[6] Russian Journal of General Chemistry, 2010, vol. 80, # 12, p. 2572 - 2589
  • 23
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  • [ 112883-41-7 ]
Reference: [1] Patent: US5097013, 1992, A,
  • 24
  • [ 28920-43-6 ]
  • [ 210345-89-4 ]
  • [ 1018899-99-4 ]
Reference: [1] Chemical communications (Cambridge, England), 2001, # 22, p. 2330 - 2331
  • 25
  • [ 2280-27-5 ]
  • [ 28920-43-6 ]
  • [ 1217603-41-2 ]
Reference: [1] Nature Chemistry, 2010, vol. 2, # 4, p. 280 - 285
  • 26
  • [ 28920-43-6 ]
  • [ 49606-99-7 ]
  • [ 1212257-18-5 ]
YieldReaction ConditionsOperation in experiment
84% With sodium carbonate In 1,4-dioxane; water at 0 - 25℃; for 8.17 h; (5)-2-((((9/ -fluoren-9-yl)methoxy)carbonyl)amino)-2-cyclopropylacetic acid (43a): To a stirred solution of Na2C03 (2.3 g) in water (34 mL) was added (2C12); FT-IR (neat) 2669, 2335, 2159, 2106, 1785, 1689, 1550, 1489, 1463, 1433, 1369, 1296, 1253, 1172, 1128, 1001 cm"1; NMR: (CDCI3, 600 MHz) δ = 7.76 (d, 2 H, J = 7.2 Hz), 7.60-7.59 (m, 2 H), 7.41-7.39 (m, 2 H), 7.32-7.30 (m, 2 H), 5.36 (d, 1 H, J = 6), 4.45-4.39 (m, 2 H), 4.24-4.21 (m, 1 H), 3.83-3.81 (m, 1 H), 1.14-1.13 (m, 1 H), 0.65-0.46 (m, 5 H) ppm. 13C NMR: (CDCI3, 150 MHz) δ = 176.6, 156.2, 143.9, 143.8, 141.4, 127.9, 127.2, 125.2, 125.1, 120.1, 67.3, 57.4, 47.3, 13.9, 3.4 ppm; HRMS calcd for C20H19NO4 [ +Na+] 360.1206 found 360.1193.
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 5, p. 1698 - 1708
[2] Patent: WO2016/138288, 2016, A1, . Location in patent: Page/Page column 124
  • 27
  • [ 28920-43-6 ]
  • [ 1172579-62-2 ]
Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 21, p. 6526 - 6531
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