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Chemical Structure| 696-40-2 Chemical Structure| 696-40-2

Structure of 3-Iodobenzylamine
CAS No.: 696-40-2

Chemical Structure| 696-40-2

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Product Details of [ 696-40-2 ]

CAS No. :696-40-2
Formula : C7H8IN
M.W : 233.05
SMILES Code : NCC1=CC=CC(I)=C1
MDL No. :MFCD00192227
InChI Key :LQLOGZQVKUNBRX-UHFFFAOYSA-N
Pubchem ID :97012

Safety of [ 696-40-2 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P501-P260-P264-P280-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P405
Class:8
UN#:2735
Packing Group:

Application In Synthesis of [ 696-40-2 ]

* 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.

  • Downstream synthetic route of [ 696-40-2 ]

[ 696-40-2 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 1184-90-3 ]
  • [ 696-40-2 ]
  • [ 80663-96-3 ]
YieldReaction ConditionsOperation in experiment
In methanol; for 16h;Heating / reflux; [0247] 3-Iodobenzylguanidine (3.9). To a solution containing 168 mg (721 mumol) of 3.8 in 1 mL of methanol was added 90.1 mg (726 mumol) of 3.7. The reaction solution was refluxed for 16 h and then concentrated under reduced pressure to give 3.9 as a viscous yellow gum: yield 258 mg. HPLC analysis was preformed using a nucleosil C18 reversed-phase column. A retention time of 24.54 min was generated when the column was eluted with 80% H2O (0.01 M NaH2PO4): 20% CH3CN at a flow rate of 2.0 mL/min and lambda=231 nm. 1H NMR (MeOH, 200 MHz): delta 4.22 (s, 2H), 6.99 (t, 1H), 7.22 (d, 1H), 7.49 (d, 1H), 7.56 (s, 1H). 13C NMR (MeOH, 50.3 MHz): delta 48.95, 99.31, 131.64, 135.72, 141.05, 141.93, 144.30, 162.65. IR (thin film): 3407, 3192, 1653, 1115 cm-1. MS (ESMS, methanol), m/z 276.1 [M+H]+.
  • 2
  • [ 24424-99-5 ]
  • [ 696-40-2 ]
  • [ 263351-43-5 ]
YieldReaction ConditionsOperation in experiment
89% With triethylamine; In dichloromethane; at 20℃; for 4.5h; In a 100 rnL round-bottom flask with magnetic stirrer and balloon (for pressure equalization and exclusion of moisture), a solution of di-tert-buty dicarbonate (0.72 g, 3.3 mmol, 1.2 equiv.) in CH2Cl2 (5 mL) was added all at once at room temperature to a solution of 3-iodobenzylamine (641 mg, 2.75 mmol) and triethylamine (0.57 mL, 4.1 mmol, 1.5 equiv.) in CH2Cl2 (10 mL). The mixture was stirred at room temperature for 4.5 h. TLC after 3.5 h (SiO2, EtOAc/hexane/Et3N 22:78:5) indicated complete conversion of the amine (Rf approx. 0.05), whereas a strongly UV-active impurity (R{ approx. 0.65) remained unchanged, and the product was detected at R{ approx. 0.55. With EtOAc/hexane 1:9 as eluent, product and impurity exhibit R{ values of approx. 0.2 and 0.4, respectively. The reaction mixture was evaporated, and the residue was chromato graphed on SiO2 (26 x 3.8 cm, EtOAc/hexane 6:94 until the nonpolar impurity was completely eluted, then 1:4). Evaporation and drying (40 C/oil pump) furnished 820 mg (89%) of a colorless solid. Mp 53.5-54.5 0C. MS (EI) m/z 333 (M+, 0.2%), 277 (33%), 276 (38%), 232 (6.4%), 217 (11%), 150 (5.4%), 106 (19%), 59 (26%), 57 (100%).
88% In dichloromethane; at 20℃; for 12h; To a stirred solution containing 1 mL (7.5 MMOL) of 3-iodobenzylamine and 15 mL of DICHLOROMETHANE was added 1.7 g (7.87 MMOL) of di-tert-butyl dicarbonate. The reaction mixture was allowed to stir at room temperature for 12 h, then diluted with ether and washed successively with water, 10% aqueous NAOH, 10% aqueous HCI, and brine, and dried over MGS04. The solvents were removed under reduced pressure to give the title compound as a white solid (2.20g, 88%). 1H NMR (300 MHz, CDCI3) 95 1. 45 (s, 9H), 4.26 (d, 2H, J = 6.0 Hz), 4.83 (brs, 1H), 7.05 (dd, 1H, J = 7.5 and 7.5 Hz), 7.24 (d, 1H, J = 7.5 Hz), 7.58 (d, 1 H, J = 7.5 Hz), and 7.62 (s, 1 H).
With triethylamine; In dichloromethane; at 20℃; for 4.5h; Example 25 tert-Butyl [3-[5-[(2(S)-Azetidinyl)methoxy]-3-pyridyl]benzyl]carbamate RRN 394 tert-Butyl 3-Iodobenzylcarbamate [1332] di-tert-butyl dicarbonate (0.72 g, 3.3 mmol, 1.2 equiv.) in CH2Cl2 (5 mL) was added all at once at room temperature to a solution of 3-iodobenzylamine (641 mg, 2.75 mmol) and triethylamine (0.57 mL, 4.1 mmol, 1.5 equiv.) in CH2Cl2 (10 mL). The mixture was stirred at room temperature for 4.5 h. TLC after 3.5 h (SiO2, EtOAc/hexane/Et3N 22:78:5) indicated complete conversion of the amine (Rf approx. 0.05), whereas a strongly UV-active impurity (Rf approx. 0.65) remained unchanged, and the product was detected at Rf approx. 0.55. With EtOAc/hexane 1:9 as eluent, product and impurity exhibit Rf values of approx. 0.2 and 0.4, respectively. The reaction mixture was evaporated, and the residue was chromatographed on SiO2 (26×3.8 cm, EtOAc/ hexane 6:94 until the nonpolar impurity was completely eluted, then 1:4). Evaporation and drying (40 C./oil pump) furnished 820 mg (89%) of a colorless solid. Mp 53.5-54.5 C. MS (EI) m/z 333 (M+, 0.2%), 277 (33%), 276 (38%), 232 (6.4%), 217 (11%), 150 (5.4%), 106 (19%), 59 (26%), 57 (100%).
  • 3
  • [ 60076-09-7 ]
  • [ 696-40-2 ]
 

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