Home Cart 0 Sign in  
X

[ CAS No. 186663-74-1 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 186663-74-1
Chemical Structure| 186663-74-1
Structure of 186663-74-1 * Storage: {[proInfo.prStorage]}

Quality Control of [ 186663-74-1 ]

Related Doc. of [ 186663-74-1 ]

SDS
Alternatived Products of [ 186663-74-1 ]
Alternatived Products of [ 186663-74-1 ]

Product Details of [ 186663-74-1 ]

CAS No. :186663-74-1 MDL No. :MFCD06411300
Formula : C11H15NO3 Boiling Point : 265.6°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :209.24 g/mol Pubchem ID :4935485
Synonyms :

Safety of [ 186663-74-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H317-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 186663-74-1 ]

  • Upstream synthesis route of [ 186663-74-1 ]
  • Downstream synthetic route of [ 186663-74-1 ]

[ 186663-74-1 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 24424-99-5 ]
  • [ 95-55-6 ]
  • [ 186663-74-1 ]
YieldReaction ConditionsOperation in experiment
99% With iron(III) trifluoromethanesulfonate In neat (no solvent) at 20℃; for 0.0833333 h; Green chemistry General procedure: Fe(OTf)3 (1 molpercent) was added to a magnetically stirred mixture of anamine (1 mmol) and Boc2O (1 mmol) at room temperature. The mixturewas stirred until completion of the reaction (TLC), then diluted withEtOAc and washed with water. The organic layer was dried overanhydrous MgSO4, then the solvent was distillated off under vacuum toyield the highly pure N‑Boc derivatives
99% at 20℃; for 0.216667 h; Ionic liquid To the ionic liquid [TPA][Pro] (1 mL) was added amine (1-14; Table-1) (1 mmol) and di-tert-butyl dicarbonate (1.2 mmol). The reaction was stirred at room temperature for an appropriate time (Table-1). After completion of the reaction as monitored by TLC, water was added to the reaction mixture and the product was extracted into ethyl acetate (3 × 20 mL). The combined organic layer was washed with brine solution and concentrated under reduced pressure to give crude product, which was purified over silica gel column to afford corresponding N-tert-butylcarbamate. The ionic liquid [TPA][Pro] in aqueous solution was recovered by removing water under reduced pressure and dried. The recovered ionic liquid was reused for five times without loss of its activity. Finally, all the compounds confirmed by their m.p.’s, IR, 1H NMR, 13C NMR, mass spectral data and elemental analysis wherever needed.
97% for 16 h; 2-Amino phenol (6 g, 55 mmol) was dissolved in 60 mL of THF. (Boc)20 (12 g, 55 mmol) was added to the above mixture and stirred for 16 h. The mixture was concentrated under vacuum to get a gummy mass. Gummy mass was precipitated using 20percent MTBE/Hexane. Precipitated solid was filtered and washed with hexane to afford tert-butyl (2- hydroxyphenyl)carbamate (1 1.2 g, 97percent yield)
96% With guanidine hydrochloride In ethanol at 35 - 40℃; for 0.25 h; General procedure: Amine (1 mmol) was added to a magnetically stirred solution of guanidine hydrochloride (15 molpercent) and di-tert-butyl dicarbonate (1.2 mmol) in EtOH (1 mL), at 35-40°C and stirred for appropriate time (Table 1). After completion of the reaction (followed by TLC or GC), EtOH was evaporated under vacuum and the residue either was washed with water to remove the catalyst or was dissolved in CH2Cl2 (or EtOAc) and filtered off to separate out the catalyst. Evaporation of the organic solvent (if used in work up) gives almost a pure product. In the cases of using an excess (Boc)2O the product was washed with petroleum ether or hexane to recover the residual (Boc)2O. If necessary, the product was further purified either by crystallization (hexane and dichloromethane, or diethyl ether and petroleum ether) or silica gel column chromatography using EtOAc-hexane (1: 6) as eluent.
95% With iron oxide In ethanol at 20℃; for 0.5 h; Green chemistry General procedure: A round-bottom flask (10 mL), which contains EtOH(5 mL), was charged with a solution of diboc (1–2 mmol),nano-Fe3O4 (3 molpercent, 0.007 g) and the amine (1 mmol). The mixture was stirred at room temperature for the appropriate time (Table 3). After completion of the reaction, the catalyst was collected by a magnet and separated from the solution of product and the remaining starting materials.After drying and evaporation of the solvent, the resulting solid was recrystallized from n-hexane or ethyl acetate(5 mL) to give the pure product. The recovered catalyst was washed with EtOH, dried and reused for the next run. The catalyst was recovered and reused for six times without any significant changes in the yield and the reaction time.
95%
Stage #1: With C12H24KO6(1+)*Br3H(1-) In ethanol at 20℃; for 0.0166667 h;
Stage #2: at 20℃; for 0.666667 h;
For the N-boc protection of amines, to solution of diboc (1 mmol) in ethanol (5 ml) was added {K*18-crown-6]Br3}n (0.001 mmol). The solution was stirred at room temperature for 1 min. The amine (1 mmol) was then added and solution as stirred at room temperature for an appropriate time (table 1). After completion of the reaction, the solvent was removed by water bath distillation. To the residue was added ethyl acetate (5 ml) and the mixture was filtered (the catalyst is insoluble in n-hexane and ethyl acetate). The solid was washed with ethyl acetate ()10 ml*2) amd combined filtrates were reduced to dryness to yield the pure products.
94% at 30℃; for 16 h; Inert atmosphere General procedure: The corresponding aminophenol (1 mmol) and Boc2O (1 mmol) were stirred at 30 °C for 16 h undersolvent free conditions. The crude reaction mixture was purified by FC eluting with hexane/EtOAc(8:2).
93% at 20℃; for 0.5 h; Green chemistry General procedure: To (Boc)2O (1.0 mmol), was added an amine (1.0 mmol)and the mixture was stirred at room temperature for the time indicated in Table 1. The progress of the reaction was monitored by TLC. In most cases, the BOC protected product was found to be sufficiently pure and did not require any further purification. In some cases the product was purified by silica gel column chromatography (1:2; EtOAc/ Petrolium ether).All products were characterized by IR, 1H NMR and their physical properties.
92% With 1,3-disulfonic acid imidazolium hydrogen sulfate In neat (no solvent) at 20℃; for 0.133333 h; Green chemistry General procedure: Amine (1 mmol) was added to the mixture of (Boc)2O (1 mmol) and DSIMHS (6.5 mg, ~ 0.02 mmol) with constant stirring at room temperature under solvent-free conditions. After completion of the reaction (monitored by TLC),   ethyl acetate (3 × 5 mL) was added to the reaction mixture and the catalyst was decanted and washed with ethyl acetate (2 × 5 mL) and dried. The product was purified by column chromatography, using   ethyl acetate–petroleum ether (2:8) eluent.
87.7% Inert atmosphere To a stirred solution of 2-aminophenol (5.0 g, 45.87 mmol) in anhydrous THF(50 mL) was added di-t-butyl dicarbonate (10.5 g, 48.17 mmol) dropwise, and thesolution was stirred overnight under argon atmosphere. Then the reaction mixture wasdiluted with ethyl acetate (80 mL) and washed with saturated brine (60 mL), water(60 mL×2), and then dried over anhydrous magnesium sulfate. The crude product waspurified by silica gel column chromatography (petroleum ether/ethyl acetate = 20:1)to afford the title compound as a white solid (8.4 g, 87.7percent); mp 148-150 °C; 1H NMR(400 MHz, Acetone-d6) δ (ppm) 8.86 (s, 1H), 7.73 (d, J = 7.6 Hz, 1H), 7.63 (brs, 1H),6.89-6.82 (m, 3H), 1.51 (s, 9H); HRMS (ESI): m/z, Calcd. for C6H8ON [M+H-Boc]+:110.0600, Found 110.0602.
80% at 20℃; for 15 h; Inert atmosphere Di-tert-butyldicarbonate (11 mmol) was added to a stirred solution of 2-aminophenol (10 mmol) in dry THF (15 mL). The reaction mixture was stirred for 15 hours at room temperature (RT) under a nitrogen atmosphere. Then, the solvent was evaporated under vacuum and the resulting reaction mixture was washed with pentane (20 mL) and dissolved into diethyl ether (30 mL). Diethyl ether portion was washed with diluted HCl (10 mL), then dried over Na2SO4 and filtered. On evaporation under vacuum the targeted compound was obtained as a white solid (80percent). 1H NMR data were: δH (500 MHz; CDCl3) 8.17 (1H, s, H-N), 7.11-6.81 (4H, m, ArH), and 1.52 (9H, s, CH3); and δc (500 MHz; CDCl3) 155.0 (C=O), 147.2 (C), 125.8 (C), 121.6 (CH), 120.7 (CH), 118.6 (CH), 82.0 (C), and 28.35 (CH3).
8.1 g With triethylamine In pyridine at 0 - 25℃; for 12 h; 2-aminophenol (3.93 g, 36 mmol) was stirred with te/t-butoxycarbonyl dicarbonate (8.32 g, 38 mmol) in dry pyridine (30 mL) with triethylamine (4 mL) warming from 0°C to 25°C over 12 h. The volatiles were evaporated and the residue partitioned between diethyl ether and phosphate buffer (pH=10); the ether layer was washed with phosphate buffer then brine, dried on Na2S04, filtered and evaporated to yield 8.1 g of dark crude product which could be purified by column chromatography (20:1->5:1 Hex:EA), or by fractional crystallisations from acetone-hexane followed by hot hexane trituration. NMR spectra matched literature dataC45]: ^-NMR (400 MHz): δ = 8.15 (s br, 1H), 7.08-7.00 (m, 2H), 6.99 (d, 7.9 Hz, 1H), 6.88 (~t, 7.5 Hz, 1H), 6.69 (s, 1H), 1.56 (s, 9H) ppm. 13C-NMR (100 MHz): δ = 155.1, 147.6, 125.7, 125.5, 121.5, 120.7, 119.1, 82.2, 28.3 (x3) ppm. DIMS(+): 210 Th = [MH]+.
180 g at 25 - 40℃; for 10 h; A mixture of dichioromethane (500 ml) and 2-aminophenol (100 gms) were stirred for 15 minutes at 25-30°C. Di-tert-butyl dicarbonate (240 gms) was slowly added to thereaction mixture at 25-30°C. Heated the reaction mixture to 35-40°C and stirred for 10 hours at the same temperature. Distilled off the solvent completely from the reaction mixture under reduced pressure. Petroleum ether (200 ml) was added to the obtained compound at below 40°C and stirred for 15 minutes at the same temperature. Distilled off the solvent completely from the reaction mixture under reduced pressure. Petroleum ether (500 ml) was added to theobtained compound at 25-30°C. Heated the reaction mixture to 50-55°C and stirred for 1 hour at the same temperature. Cooled the reaction mixture to 25-30°C and stirred for 3 hours at the same temperature. Filtered the solid, washed with petroleum ether and dried to get the title compound. Yield: 180 gms; Melting point: 140-144°C

Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 7, p. 1087 - 1091
[2] Journal of Chemical Research, 2013, vol. 37, # 12, p. 757 - 760
[3] Asian Journal of Chemistry, 2017, vol. 29, # 6, p. 1313 - 1316
[4] Journal of Organic Chemistry, 2002, vol. 67, # 14, p. 4882 - 4892
[5] Comptes Rendus Chimie, 2010, vol. 13, # 5, p. 544 - 547
[6] Letters in Organic Chemistry, 2011, vol. 8, # 1, p. 38 - 42
[7] Letters in Organic Chemistry, 2012, vol. 9, # 3, p. 165 - 168
[8] Organic Letters, 2017, vol. 19, # 17, p. 4696 - 4699
[9] Patent: WO2015/79459, 2015, A1, . Location in patent: Paragraph 00226
[10] Tetrahedron, 2000, vol. 56, # 4, p. 605 - 614
[11] Tetrahedron Letters, 2011, vol. 52, # 12, p. 1260 - 1264
[12] Tetrahedron Letters, 2008, vol. 49, # 21, p. 3527 - 3529
[13] Synthesis, 2008, # 19, p. 3126 - 3130
[14] Catalysis Communications, 2011, vol. 12, # 12, p. 1088 - 1094
[15] Comptes Rendus Chimie, 2013, vol. 16, # 11, p. 962 - 966
[16] Chinese Journal of Catalysis, 2013, vol. 34, # 9, p. 1730 - 1733
[17] Heterocycles, 2006, vol. 70, p. 309 - 319
[18] Tetrahedron Letters, 2010, vol. 51, # 49, p. 6388 - 6391
[19] Journal of the Iranian Chemical Society, 2012, vol. 9, # 4, p. 495 - 502
[20] RSC Advances, 2015, vol. 5, # 26, p. 19790 - 19798
[21] Synlett, 2017, vol. 28, # 4, p. 471 - 474
[22] Letters in Organic Chemistry, 2013, vol. 10, # 2, p. 121 - 125
[23] Tetrahedron Letters, 2009, vol. 50, # 46, p. 6244 - 6246
[24] Synthetic Communications, 2011, vol. 41, # 5, p. 715 - 719
[25] Monatshefte fur Chemie, 2012, vol. 143, # 4, p. 631 - 635
[26] Journal of Molecular Liquids, 2013, vol. 177, p. 386 - 393
[27] Journal of the Iranian Chemical Society, 2013, vol. 10, # 2, p. 181 - 188
[28] Synthetic Communications, 2004, vol. 34, # 10, p. 1791 - 1799
[29] Synlett, 2007, # 5, p. 806 - 808
[30] Organic Letters, 2006, vol. 8, # 15, p. 3259 - 3262
[31] Journal of Organic Chemistry, 2006, vol. 71, # 21, p. 8283 - 8286
[32] Tetrahedron Letters, 2007, vol. 48, # 33, p. 5865 - 5868
[33] Tetrahedron Letters, 2007, vol. 48, # 47, p. 8318 - 8322
[34] Journal of Organic Chemistry, 2011, vol. 76, # 17, p. 7132 - 7140
[35] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 2186 - 2197
[36] Tetrahedron Letters, 2006, vol. 47, # 38, p. 6739 - 6742
[37] Journal of the Chinese Chemical Society, 2011, vol. 58, # 4, p. 538 - 543
[38] Polymer, 2011, vol. 52, # 20, p. 4451 - 4455
[39] Synthetic Communications, 2012, vol. 42, # 1, p. 25 - 32
[40] Patent: US2014/323720, 2014, A1, . Location in patent: Paragraph 0050; 0051
[41] RSC Advances, 2015, vol. 5, # 9, p. 6993 - 7000
[42] Heterocycles, 2009, vol. 77, # 2, p. 1123 - 1146
[43] Synthesis, 2006, # 16, p. 2784 - 2788
[44] European Journal of Inorganic Chemistry, 2017, vol. 2017, # 33, p. 3908 - 3918
[45] Journal of Medicinal Chemistry, 2014, vol. 57, # 10, p. 4239 - 4251
[46] Tetrahedron Letters, 2004, vol. 45, # 50, p. 9171 - 9175
[47] European Journal of Organic Chemistry, 2016, vol. 2016, # 35, p. 5887 - 5896
[48] Tetrahedron Letters, 2010, vol. 51, # 16, p. 2102 - 2105
[49] Chemistry - A European Journal, 2017, vol. 23, # 62, p. 15759 - 15765
[50] Tetrahedron Letters, 1998, vol. 39, # 32, p. 5763 - 5764
[51] Patent: US2003/207882, 2003, A1,
[52] Patent: WO2015/166295, 2015, A1, . Location in patent: Page/Page column 69-70
[53] Patent: WO2016/142954, 2016, A2, . Location in patent: Page/Page column 13; 15
[54] Organic and Biomolecular Chemistry, 2017, vol. 15, # 16, p. 3435 - 3443
[55] Organic and Biomolecular Chemistry, 2017, vol. 15, # 33, p. 6892 - 6895
  • 2
  • [ 1095280-61-7 ]
  • [ 186663-74-1 ]
Reference: [1] European Journal of Organic Chemistry, 2008, # 30, p. 5135 - 5143
  • 3
  • [ 1095280-64-0 ]
  • [ 186663-74-1 ]
Reference: [1] European Journal of Organic Chemistry, 2008, # 30, p. 5135 - 5143
  • 4
  • [ 24424-99-5 ]
  • [ 88-75-5 ]
  • [ 186663-74-1 ]
Reference: [1] Synlett, 2002, # 5, p. 771 - 772
  • 5
  • [ 1538-75-6 ]
  • [ 95-55-6 ]
  • [ 186663-74-1 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 2012, vol. 51, # 8, p. 1168 - 1172,5
  • 6
  • [ 93299-48-0 ]
  • [ 186663-74-1 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 9, p. 1071 - 1074
  • 7
  • [ 51779-32-9 ]
  • [ 95-55-6 ]
  • [ 186663-74-1 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 11, p. 2789 - 2792
  • 8
  • [ 3422-01-3 ]
  • [ 186663-74-1 ]
Reference: [1] Tetrahedron, 2003, vol. 59, # 11, p. 1895 - 1900
  • 9
  • [ 1093102-81-8 ]
  • [ 186663-74-1 ]
Reference: [1] European Journal of Organic Chemistry, 2008, # 30, p. 5135 - 5143
Historical Records

Related Functional Groups of
[ 186663-74-1 ]

Amines

Chemical Structure| 54840-15-2

[ 54840-15-2 ]

tert-Butyl (4-hydroxyphenyl)carbamate

Similarity: 0.93

Chemical Structure| 19962-06-2

[ 19962-06-2 ]

tert-Butyl (3-hydroxyphenyl)carbamate

Similarity: 0.92

Chemical Structure| 71026-66-9

[ 71026-66-9 ]

tert-Butyl (4-aminophenyl)carbamate

Similarity: 0.83

Chemical Structure| 68621-88-5

[ 68621-88-5 ]

tert-Butyl (3-aminophenyl)carbamate

Similarity: 0.82

Chemical Structure| 1134328-09-8

[ 1134328-09-8 ]

tert-Butyl (3-(methylamino)phenyl)carbamate

Similarity: 0.82

Aryls

Chemical Structure| 54840-15-2

[ 54840-15-2 ]

tert-Butyl (4-hydroxyphenyl)carbamate

Similarity: 0.93

Chemical Structure| 19962-06-2

[ 19962-06-2 ]

tert-Butyl (3-hydroxyphenyl)carbamate

Similarity: 0.92

Chemical Structure| 71026-66-9

[ 71026-66-9 ]

tert-Butyl (4-aminophenyl)carbamate

Similarity: 0.83

Chemical Structure| 68621-88-5

[ 68621-88-5 ]

tert-Butyl (3-aminophenyl)carbamate

Similarity: 0.82

Chemical Structure| 1134328-09-8

[ 1134328-09-8 ]

tert-Butyl (3-(methylamino)phenyl)carbamate

Similarity: 0.82

Amides

Chemical Structure| 54840-15-2

[ 54840-15-2 ]

tert-Butyl (4-hydroxyphenyl)carbamate

Similarity: 0.93

Chemical Structure| 19962-06-2

[ 19962-06-2 ]

tert-Butyl (3-hydroxyphenyl)carbamate

Similarity: 0.92

Chemical Structure| 71026-66-9

[ 71026-66-9 ]

tert-Butyl (4-aminophenyl)carbamate

Similarity: 0.83

Chemical Structure| 68621-88-5

[ 68621-88-5 ]

tert-Butyl (3-aminophenyl)carbamate

Similarity: 0.82

Chemical Structure| 1134328-09-8

[ 1134328-09-8 ]

tert-Butyl (3-(methylamino)phenyl)carbamate

Similarity: 0.82