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[ CAS No. 33994-44-4 ]

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2D
Chemical Structure| 33994-44-4
Chemical Structure| 33994-44-4
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Product Details of [ 33994-44-4 ]

CAS No. :33994-44-4MDL No. :MFCD18399500
Formula : C10H11IO2 Boiling Point : 290.7°C at 760 mmHg
Linear Structure Formula :IC6H4C2H4COOCH3InChI Key :LDCXVBUZHUHPAJ-UHFFFAOYSA-N
M.W :290.10Pubchem ID :554150
Synonyms :

Computed Properties of [ 33994-44-4 ]

TPSA : 26.3 H-Bond Acceptor Count : 2
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.30 Rotatable Bond Count : 4

Safety of [ 33994-44-4 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 33994-44-4 ]

  • Upstream synthesis route of [ 33994-44-4 ]
  • Downstream synthetic route of [ 33994-44-4 ]

[ 33994-44-4 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 67-56-1 ]
  • [ 1643-29-4 ]
  • [ 33994-44-4 ]
YieldReaction ConditionsOperation in experiment
99% at 75℃; for 15.00 h; Inert atmosphere 4-Iodohydrocinnamic acid was prepared from hydrocinnamic acid according to literature procedures using H5IO6/I2 (Kawasaki, et al., Tetrahedron Asymm. 2001, 12(4), 585). To a stirring solution of 4-iodohydrocinnamic acid (12.248, 44.4 mmol, 1.0 equiv) in methanol (75 mL), was added H2SO4 (2.2 mL). A reflux condenser was attached and the reaction mixture was heated to reflux at 75 0C for 15 h under N2. The reaction mixture was cooled to 23 0C and the methanol was removed by rotary evaporation. The crude oil concentrate was diluted with DCM (100 mL) and ethyl acetate (15 mL). The solution was washed with water (100 mL), saturated aqueous sodium bicarbonate (100 mL) and saturated aqueous sodium chloride (100 mL). The organic layer was dried over anhydrous magnesium sulfate. The dried organics were filtered and concentrated to furnish methyl 4-iodohydrocinnamte as an off-white solid (12.898, 99percent). Mp: 46 0C.
98%
Stage #1: at 0℃; Inert atmosphere
Stage #2: at 20℃; Inert atmosphere
lntermediate-2; Methyl 3-(4-iodophenyl)propanoate.; Methanol (5 ml.) under nitrogen at O0C was added AcCI (0.4 ml_, 5.63 mmol). The reaction was stirred for 10 min before slow addition of 3-(4-iodophenyl)propanoic acid (498 mg, 1.80 mmol). The reaction was stirred for additional VA hour at room temperature, before the mixture was concentrated under vacuum, re-dissolved in MeOH and concentrated to give 512 mg (98percent) of a pure white solid. Rf: 0.39 (EtOAc:hexanes, 1 :4); 1HNMR (CDCI3) δ 7.61-7.59 (m, 2H), 6.97- 6.94 (m, 2H), 3.66 (s, 3H), 2.92-2.87 (t, 2H, J = 7.5 Hz), 2.63-2.58 (t, 2H, J = 7.5 Hz); 13CNMR (CDCI3) δ 173.0, 140.1 , 137.5, 130.4, 91.4, 51.7, 35.4, 30.4; EI-MS m/z 290.0 (MH+).
Reference: [1] Organic Letters, 2008, vol. 10, # 12, p. 2597 - 2600
[2] Patent: WO2009/137322, 2009, A2. Location in patent: Page/Page column 15
[3] Journal of the American Chemical Society, 2009, vol. 131, # 47, p. 17500 - 17521
[4] Journal of Medicinal Chemistry, 2008, vol. 51, # 22, p. 7061 - 7064
[5] Patent: WO2010/12650, 2010, A1. Location in patent: Page/Page column 39
[6] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 6, p. 1228 - 1231
[7] Chemistry - A European Journal, 2009, vol. 15, # 10, p. 2278 - 2288
[8] Patent: US2006/111582, 2006, A1. Location in patent: Page/Page column 16; 3/4
  • 2
  • [ 1643-29-4 ]
  • [ 18107-18-1 ]
  • [ 33994-44-4 ]
Reference: [1] Patent: US9408907, 2016, B2. Location in patent: Page/Page column 101
[2] Patent: WO2009/111337, 2009, A1. Location in patent: Page/Page column 209
  • 3
  • [ 186581-53-3 ]
  • [ 1643-29-4 ]
  • [ 33994-44-4 ]
Reference: [1] Journal of the American Chemical Society, 1971, vol. 93, # 19, p. 4845 - 4850
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