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[ CAS No. 13750-81-7 ]

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CAS No. :13750-81-7 MDL No. :MFCD01321308
Formula : C5H6N2O Boiling Point : 70-74°C at 1 mmHg
Linear Structure Formula :- InChI Key :-
M.W :110.11 g/mol Pubchem ID :139575
Synonyms :

Safety of [ 13750-81-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
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Application In Synthesis of [ 13750-81-7 ]

  • Upstream synthesis route of [ 13750-81-7 ]
  • Downstream synthetic route of [ 13750-81-7 ]

[ 13750-81-7 ] Synthesis Path-Upstream   1~19

  • 1
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  • [ 17334-08-6 ]
YieldReaction ConditionsOperation in experiment
87% With sodium tetrahydroborate In methanol; diethyl ether; water Synthesis of (1-Methyl-1H-imidazol-2-yl)methanol (BB6)
To a solution of compound (BB5) (40.5 g, 368 mmol) in MeOH (300 mL) at 0° C. was added NaBH4 (20.89 g, 551 mmol) portion wise.
The reaction mixture was slowly warmed to room temperature and stirred for 5 h.
The reaction mixture was cooled to 0° C., H2O (150 mL) was added and the mixture was stirred for 30 min at room temperature then concentrated in vacuo.
The crude residue was dissolved in H2O (150 mL) and extracted with CHCl3 (4*200 mL).
The combined organic layers were dried over Na2SO4 and concentrated.
The residue was stirred with Et2O (150 mL) and filtered to afford (BB6) (36 g, 87percent) as a white solid. Rf: 0.4 (15percent MeOH/CHCl3).
1H NMR (400 MHz, CDCl3): δ 6.89 (1H, app d), 6.83 (1H, app d), 4.66 (2H, s), 3.72 (31-1, s); m/z 113 (MH)+.
42%
Stage #1: With sodium tetrahydroborate In ethanol at 20℃; for 2 h;
Stage #2: With methanol In ethanol
Sodium borohydride (380 mg, 10 mmol) was added to a solution of 1-methyl-1H-imidazole-2-carbaldehyde (1.1 g, 10 mmol) in ethanol (25 .ml). The mixture was stirred atroom temperature for 2 hours. The reaction was quenched by addition of methanol (20ml). The mixture was partitioned between water and dichloromethane. The combinedorganic extracts were dried over magnesium sulfate and concentrated to give the productas a white solid (480 mg, 42percent yield). ]H-NMR (400 MHz, CDC13): 3.73 (3H, s, Me),4.32 (1H, bs, OH), 4.67 (2H, s, CH2), 6.84 (1H, s, CH), 6.90 (1H, s, CH).
Reference: [1] Tetrahedron, 2000, vol. 56, # 4, p. 645 - 657
[2] Patent: US2012/322722, 2012, A1,
[3] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 2, p. 363 - 386
[4] Tetrahedron, 1996, vol. 52, # 48, p. 15171 - 15188
[5] South African Journal of Chemistry, 2012, vol. 65, p. 231 - 238
[6] Patent: WO2006/24820, 2006, A1, . Location in patent: Page/Page column 127
[7] Patent: WO2007/42545, 2007, A1, . Location in patent: Page/Page column 18
[8] Patent: US2008/125467, 2008, A1, . Location in patent: Page/Page column 19-20
[9] Patent: EP1422228, 2004, A1, . Location in patent: Page 222
[10] Patent: WO2006/34277, 2006, A1, . Location in patent: Page/Page column 60
[11] Patent: US2007/185136, 2007, A1, . Location in patent: Page/Page column 67
  • 2
  • [ 13750-81-7 ]
  • [ 20485-43-2 ]
YieldReaction ConditionsOperation in experiment
100% With dihydrogen peroxide In water at 20℃; for 72 h; First, 1-methylimidazole-2-carboxaldehyde was prepared according to the literature procedure[23]. The synthesis procedure then followed that of Im2COOH (1b) above and the yield was also quantitative after the removal of water under high vacuum (no washing with diethylether/water was necessary). Note: heating causes decarboxylation. Yield: 100percent. Mp=99–101°C. δH (400MHz, D2O): 7.42, 7.39 (2H, s, Im-H) and 4.08ppm (3H, s, NCH3); δC (400MHz, D2O): 158.67, 139.68, 125.83, 118.46, 36.73ppm. IR ν (KBr): 3347(m) 3119(m), 2663(w), 1641(s), 1683(m), 1507(s), 1449(m), 1388(s), 1338(s), 1285(s), 1173(m), 1123(s), 961(m) 910(m), 776(s), 685(s) cm−1. Anal. Calc. for C5H8N2O3 (144.12); C, 41.67; H, 5.59; N, 19.44percent. Found: C, 41.28; H, 5.23; N, 19.12percent.
Reference: [1] South African Journal of Chemistry, 2010, vol. 63, p. 95 - 104
[2] Journal of Inorganic Biochemistry, 2015, vol. 145, p. 11 - 18
[3] South African Journal of Chemistry, 2012, vol. 65, p. 231 - 238
  • 3
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  • [ 67-56-1 ]
  • [ 68-12-2 ]
  • [ 62366-53-4 ]
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YieldReaction ConditionsOperation in experiment
79%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5 h;
Stage #2: at -78 - 20℃; for 2 h;
General procedure: n-BuLi (1.67 M solution in hexane, 1.3 mL, 2.2 mmol) was added dropwise into a solution of p-bromoanisole (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, DMF (0.22 mL, 2.2 mmol) was added to the mixture and the obtained mixture was stirred at rt. After 2 h at the same temperature, THF was removed. Then, MeOH (3 mL) was added to the residue and the mixture was stirred at room temperature. After 30 min, I2 (1523 mg, 6 mmol) and K2CO3 (829 mg, 6 mmol) were added at 0 °C and the obtained mixture was stirred for 22 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3.x.20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide methyl 4-methoxy-1-benzoate in 82percent yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure methyl 4-methoxybenzoate as a colorless oil.
Reference: [1] Tetrahedron, 2012, vol. 68, # 24, p. 4701 - 4709
  • 4
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YieldReaction ConditionsOperation in experiment
68%
Stage #1: With n-butyllithium In tetrahydrofuran at -70℃; for 0.5 h;
Stage #2: at -70 - 0℃; for 2 h;
To a solution of 1- methylimidazole (8.2 g, 100 mmol) in dry THF (100 mL) cooled to -70 0C, was added dropwise a solution of nBuLi in THF. After stirring for 30 min at the same temperature, the solution was treated with freshly distilled DMF (7.3 g, 100 mmol). The resultant yellow suspension was stirred at 0 0C for 2 h, and quenched with ice- water. The mixture was extracted with EtOAc, and the organic extracts dried (Na2SO4) before evaporation to afford an oily residue, which was distilled under reduced pressure to afford the title product (68percent yield). 1H-NMR (CDCl3) 69.76 (s, EPO <DP n="82"/>IH, CHO), 7.22 (s, IH, Im-CH), 7.07 (s, IH, Im-CH), 3.96 (s, 3H, CH3). EI-HRMS: m/z calcd for C5H6N2O 110.0480, found 110.0481 (100percent), 82.0493 (60percent).
Reference: [1] Inorganica Chimica Acta, 2011, vol. 375, # 1, p. 213 - 219
[2] Dalton Transactions, 2015, vol. 44, # 17, p. 8013 - 8020
[3] Chemistry - A European Journal, 2015, vol. 21, # 36, p. 12735 - 12740
[4] Dalton Transactions, 2011, vol. 40, # 40, p. 10416 - 10433
[5] Tetrahedron, 2000, vol. 56, # 4, p. 645 - 657
[6] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 8, p. 2379 - 2386
[7] Monatshefte fur Chemie, 2016, vol. 147, # 12, p. 2209 - 2220
[8] New Journal of Chemistry, 2018, vol. 42, # 13, p. 10467 - 10471
[9] Patent: WO2007/45096, 2007, A1, . Location in patent: Page/Page column 41; 79-80
[10] Organic and Biomolecular Chemistry, 2009, vol. 7, # 8, p. 1633 - 1641
[11] European Journal of Organic Chemistry, 2011, # 30, p. 6092 - 6099
[12] Journal of Organometallic Chemistry, 1990, vol. 385, # 3, p. 417 - 427
[13] Journal of Medicinal Chemistry, 1991, vol. 34, # 4, p. 1363 - 1368
[14] Journal of Medicinal Chemistry, 1984, vol. 27, # 11, p. 1431 - 1438
[15] Tetrahedron, 1996, vol. 52, # 48, p. 15171 - 15188
[16] European Journal of Inorganic Chemistry, 2005, # 17, p. 3513 - 3523
[17] CrystEngComm, 2013, vol. 15, # 47, p. 10157 - 10160
[18] Croatica Chemica Acta, 2014, vol. 87, # 2, p. 153 - 160
  • 5
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YieldReaction ConditionsOperation in experiment
59% With potassium carbonate In ethanol; N,N-dimethyl-formamide at 50℃; for 5 h; Stir at room temperature To a solution of 1H-imidazole-2-carbaldehyde (250 mg, 2.6 mmol) and K2CO3 (431 mg, 3.12 mmol) in DMF (2.5 mL) was added methyl iodide (442 mg, 3.12 mmol). The mixture was stirred at 50° C. for 5 h and allowed to cool to remove solids. Water was added to the filtrate and extracted three times with ethyl acetate. The combined extracts were washed with saturated saline and dried over anhydrous sodium sulfate. The mixture was concentrated by suction and filtered to give 1-methyl-1H-imidazole-2-carboxaldehyde as a pale yellow oil (168 mg, yield 59percent).
Reference: [1] Patent: CN103570683, 2018, B, . Location in patent: Paragraph 0711; 0715-0717
[2] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 2, p. 363 - 386
[3] Chemico-Biological Interactions, 2016, vol. 259, p. 85 - 92
  • 6
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  • [ 68-12-2 ]
  • [ 62366-53-4 ]
  • [ 13750-81-7 ]
YieldReaction ConditionsOperation in experiment
79%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5 h;
Stage #2: at -78 - 20℃; for 2 h;
General procedure: n-BuLi (1.67 M solution in hexane, 1.3 mL, 2.2 mmol) was added dropwise into a solution of p-bromoanisole (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, DMF (0.22 mL, 2.2 mmol) was added to the mixture and the obtained mixture was stirred at rt. After 2 h at the same temperature, THF was removed. Then, MeOH (3 mL) was added to the residue and the mixture was stirred at room temperature. After 30 min, I2 (1523 mg, 6 mmol) and K2CO3 (829 mg, 6 mmol) were added at 0 °C and the obtained mixture was stirred for 22 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3.x.20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide methyl 4-methoxy-1-benzoate in 82percent yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure methyl 4-methoxybenzoate as a colorless oil.
Reference: [1] Tetrahedron, 2012, vol. 68, # 24, p. 4701 - 4709
  • 7
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YieldReaction ConditionsOperation in experiment
53% With sodium dihydrogenphosphate; diisopropylamine In tetrahydrofuran; water; ethyl acetate; N,N-dimethyl-formamide Synthesis of 1-Methyl-1H-imidazole-2-carbaldehyde (BB5)
To a solution of 1-methyl imidazole (57 g, 0.7 mmol) in THF (250 mL) was added LDA (2 M solution in THF, 348 mL) at -60° C. and the stirred for 3 h.
The reaction mixture was cooled -78° C., DMF (75 mL) was added rapidly, and the reaction mixture was slowly allowed to room temperature and stirred at ambient temperature overnight.
The reaction mixture was cooled to 0° C., a solution of NaH2PO4 (100 g in 350 mL H2O) was added and the resulting mixture was stirred for 30 min.
The mixture was filtered to remove insoluble material and the filtrate was extracted with DCM (4*400 mL).
The combined organic extracts were concentrated in vacuo and the crude residue was purified by column chromatography (silica gel, 100-200 mesh, 30percent EtOAc/pet. ether) to provide (BB5) (41 g, 53percent) as a yellow solid. Rf: 0.3 (15percent MeOH/CHCl3).
1H NMR (400 MHz, CDCl3): δ 9.82 (1H, s), 7.28 (1H, app d), 7.13 (1H, app d), 4.04 (3H, s); m/z 111 (MH)+.
Reference: [1] Patent: US2012/322722, 2012, A1,
[2] Liebigs Annalen der Chemie, 1980, # 4, p. 542 - 556
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Reference: [1] Organic Letters, 2011, vol. 13, # 23, p. 6264 - 6267
  • 9
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Reference: [1] Tetrahedron Asymmetry, 1999, vol. 10, # 2, p. 281 - 295
[2] Patent: EP150984, 1991, B1,
[3] Patent: US4826833, 1989, A,
  • 10
  • [ 51081-36-8 ]
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Reference: [1] Synthetic Communications, 1990, vol. 20, # 3, p. 321 - 331
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Reference: [1] Bioconjugate Chemistry, 2010, vol. 21, # 6, p. 1032 - 1042
[2] Inorganica Chimica Acta, 2012, vol. 389, p. 168 - 175
  • 12
  • [ 288-32-4 ]
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Reference: [1] South African Journal of Chemistry, 2012, vol. 65, p. 231 - 238
  • 13
  • [ 616-47-7 ]
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991, # 11, p. 2691 - 2698
  • 14
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991, # 11, p. 2691 - 2698
  • 15
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Reference: [1] Archives of Toxicology, 1998, vol. 72, # 5, p. 289 - 295
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  • [ 124312-73-8 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 29, p. 5581 - 5583
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 8, p. 2379 - 2386
  • 17
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  • [ 74-88-4 ]
  • [ 111851-98-0 ]
YieldReaction ConditionsOperation in experiment
84% With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 5 h; Example 76A1 -Ethyl- lH-imidazole-2- carbaldehyde[00631] To a suspension of lH-imidazole-2- carbaldehyde (480 mg, 5 mmol) and potassium carbonate (936 mg, 6 mmol) in N, N-dimethylformamide (7 mL) was added iodoethane (829 mg, 6mmol) and the mixture was heated at 50 °C for 5 hrs. Solvent was removed under reduced pressure. The residue was partitioned between water (30 mL) and ethyl acetate (30 mL). The aqueous layer was extracted with ethyl acetate (20 mLx3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give 1 -ethyl- lH-imidazole-2- carbaldehyde as light yellow oil (520 mg, yield 84percent). 1H MR (400 MHz, CDC13) δ (ppm): 1.42- 1.46 (t, J= 7.2 Hz, 3H), 4.42-4.47 (q, 2H), 7.19 (s, IH), 7.29 (s, IH), 9.82 (s, IH). LC-MS (ESI) m/z: 125 (M+l)+.
Reference: [1] Patent: WO2011/130661, 2011, A1, . Location in patent: Page/Page column 133-134
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Reference: [1] Journal of Heterocyclic Chemistry, 1997, vol. 34, # 5, p. 1543 - 1547
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  • [ 78667-04-6 ]
Reference: [1] Tetrahedron, 1996, vol. 52, # 48, p. 15171 - 15188
[2] Patent: US2012/322722, 2012, A1,
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