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Chemistry
Heterocyclic Building Blocks
Benzimidazoles
1H-Benzo[d]imidazole-4-carbaldehyde
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Benzimidazoles
Aldehydes

[ CAS No. 144876-36-8 ]

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Chemical Structure| 144876-36-8
Chemical Structure| 144876-36-8
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COA NMR CNMR HPLC LC-MS

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SDS Specification
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Product Details of [ 144876-36-8 ]

CAS No. :144876-36-8 MDL No. :MFCD10698555
Formula : C8H6N2O Boiling Point : -
Linear Structure Formula :- InChI Key :UNGJRTXGRUDJGM-UHFFFAOYSA-N
M.W :146.15 Pubchem ID :22663482
Synonyms :

Safety of [ 144876-36-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H312-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 144876-36-8 ]

* 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 [ 144876-36-8 ]

[ 144876-36-8 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 65658-13-1 ]
  • [ 144876-36-8 ]
YieldReaction ConditionsOperation in experiment
79% With manganese(IV) oxide; In dichloromethane; N,N-dimethyl-formamide; at 20℃; for 4h; To a solution of <strong>[65658-13-1](1H-benzo[d]imidazol-4-yl)methanol</strong> (0.356 g, 2.40 mmol) in CH2Cl2/DMF (1:1, 50 mL) was added activated MnO2 (2.086 g, 24.00 mmol). The reaction was stirred at room temperature until TLC showed full conversion (4 hours). The reaction was filtered through a tight-packed pad of Celite and the pad was washed with CH2Cl2 (2 × 15 mL). The filtrate was evaporated and the solids were recrystallized from EtOAc/heptanes to give the title compound 4 (0.277 g, 79%) as pale yellow crystals. mp. 163 - 164 C. 1H NMR (300 MHz, DMSO-d6) δ 10.24 (s, 1H), 8.33 (s, 1H), 8.00 (dd, J = 8.0, 1.0 Hz, 1H), 7.83 (dd, J = 7.4, 1.0 Hz, 1H), 7.40 (dd, J = 8.0, 7.4 Hz,, 1H). 13C NMR (75 MHz, DMSO) δ 191.7, 144.2, 142.5, 127.0, 124.6, 122.2, 121.4
33.8% With Dess-Martin periodane; In dichloromethane; at 20℃; for 12h; To a stirred solution of lH-l,3-benzodiazol-4-ylmethanol (1.20 g, 8.10 mmol, 1.00 equiv) in DCM (25.00 mL) was added Dess-Martin (6870.32 mg, 16.20 mmol, 2.00 equiv) at room temperature. After stirring for 12 hours at room temperature, saturated sodium thiosulfate solution (100 mL) was added. The mixture was extracted with DCM and the combined organic layers were washed saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, fdtered and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, eluent: petroleum ether/ethyl acetate 42:58) to give 1H-1,3- benzodiazole-4-carbaldehyde (400 mg, 33.8%) as a white solid.
18% With pyridine-SO3 complex; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 20℃; C. lH-Benzo[d]imidazole-4-carbaldehyde.; (lH-Benzo[d]imidazol-4- yl)methanol (550 mg, 3.72 mmol) was dissolved in dimethylsulfoxide (30 mL). Diisopropylethylamine (1.9 mL, 1 1.1 mmol) and sulfurtrioxide complex of pyridine (1.77 g, 1 1.1 mmol) was added and the solution allowed to stir overnight at room temperature.Poured reaction into water (50 mL) and extracted with ethyl acetate (3x150 mL), dried with sodium sulfate, and concentrated under reduced pressure to give a white solid (100 mg, 18%). MS (ESI) m/z 147.0 [M+l]+.
With sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; 7 g (1 H-Benzoimidazol-4- yl)methanol was dissolved in 350 ml of dimethyl sulfoxide. 36 ml of diisopropylethylamine and 33 g of sulfurtrioxide pyridine complex was added. The reaction was stirred overnight. 800 ml of water was added and the mixture wasextracted with 400 ml of ethyl acetate for five times. The organic layers were washed with brine, dried with sodium sulfate and evaporated. Flash chromatography (100% ethyl acetate) yielded yellowish powder of 1 H-Benzoimidazole-4-carbaldehyde(M+1= 147.1)

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3933 - 3937
[2]Patent: WO2020/210649,2020,A1 .Location in patent: Paragraph 0479
[3]Patent: WO2008/51494,2008,A1 .Location in patent: Page/Page column 132
[4]Patent: WO2017/177026,2017,A1 .Location in patent: Page/Page column 33
  • 2
  • [ 603-81-6 ]
  • [ 144876-36-8 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3933 - 3937
[2]Patent: WO2017/177026,2017,A1
  • 3
  • [ 46006-36-4 ]
  • [ 144876-36-8 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3933 - 3937
[2]Patent: WO2017/177026,2017,A1
  • 4
  • [ 37619-25-3 ]
  • [ 144876-36-8 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3933 - 3937

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