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[ CAS No. 56-40-6 ]

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Chemical Structure| 56-40-6
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CAS No. :56-40-6 MDL No. :MFCD00008131
Formula : C2H5NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :75.07 g/mol Pubchem ID :750
Synonyms :

Safety of [ 56-40-6 ]

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

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  • Upstream synthesis route of [ 56-40-6 ]
  • Downstream synthetic route of [ 56-40-6 ]

[ 56-40-6 ] Synthesis Path-Upstream   1~52

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Reference: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1983, vol. 37, # 10, p. 879 - 890
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Reference: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1983, vol. 37, # 10, p. 879 - 890
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Reference: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1983, vol. 37, # 10, p. 879 - 890
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  • [ 13925-07-0 ]
  • [ 13925-09-2 ]
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  • [ 13360-64-0 ]
  • [ 15707-34-3 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708
  • 5
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  • [ 302-72-7 ]
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YieldReaction ConditionsOperation in experiment
0.18 mg With ferric sulfate nonahydrate In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
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YieldReaction ConditionsOperation in experiment
0.12 mg With magnesium sulfate In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
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YieldReaction ConditionsOperation in experiment
1.6 mg With copper(II) choride dihydrate In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
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Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
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Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
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Reference: [1] Arkivoc, 2018, vol. 2018, # 3, p. 338 - 352
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YieldReaction ConditionsOperation in experiment
99.34% With sodium carbonate In water for 5 h; General procedure: Sodium carbonate (Na2CO3, 1.590g, 15mmol) was added to a solution of amino acids (2a-h, 12.5mmol) in water (15mL) with continuous stirring until all the solutes had dissolved. The solution was cooled to−5°C and the appropriate benzenesulphonyl chloride (1a-c, 15mmol) was added in four portions over a period of 1h. The slurry was further stirred at room temperature for about 4h. The progress of the reaction was monitored using TLC (MeOH/DCM, 1:9). Upon completion, the mixture was acidified using 20percent aqueous hydrochloric acid to pH 2. The crystals was filtered via suction and washed with pH 2.2 buffer. The pure products (3a-x) were dried over self-indicating fused silica gel in a desiccator. 2.2.1 2-(4-methylphenylsulphonamido) acetic acid (3a) The amino acid was glycine, yield (2.8410g, 99.34percent), mp, 88.4–88.6°C, FTIR (KBr, cm−1): 3448 (OH of COOH), 3277 (NH), 2957 (C-H aliphatic), 1730 (C=O), 1598, 1440 (C=C), 1354, 1321 (2S=O), 1185 (SO2-NH), 1111, 1094 (C-N, C-O). 1H NMR (DMSO-d6)δ: 7.90–7.88 (t, J=6.3Hz, 1H, NH), 7.65–7.63 (d, J=8.6Hz, 2H, ArH), 7.34–7.33 (d, J=8.05Hz, 2H, ArH), 3.52–3.51 (d, J=5.7Hz, CH2), 2.34 (s, 3H, CH3). 13C NMR (DMSO-d6)δ: 170.7 (C=O), 143.1, 138.4, 130.0, 127.1 (aromatic carbons), 44.3 (CH2), 21.5 (CH3). HRMS-ESI (m/z): 228.0412 (M-H)-, calculated, 228.0408.
99.34% With sodium carbonate In water for 4 h; General procedure: Sodium carbonate (Na2CO3, 1.590 g, 15 mmol) was added to a solution of amino acids (6a-h,12.5 mmol) in water (15 mL) with continuous stirring until all the solutes dissolved. The solutionwas cooled to -5°C and an appropriate benzenesulphonyl chloride (5a-c, 15 mmol) wasadded in four portions over a period of 1 h. The slurry was further stirred at room temperaturefor 4 h. The progress of the reaction was monitored by using TLC (MeOH/DCM, 1:9). Uponcompletion, the mixture was acidified using 20percent aqueous hydrochloric acid to pH 2. The crystalswas filtered via suction and washed with pH 2.2 buffer. The pure products (7a-x) weredried over self-indicating fused silica gel in a desiccator. 2-(4-methylphenylsulphonamido) acetic acid (7a). The amino acid was glycine, yield(2.8410 g, 99.34percent), appearance white needles, mp, 88.4-88.6°C, FTIR (KBr, cm-1): 3448 (OHof COOH), 3277 (NH), 2957 (C-H aliphatic), 1730 (C = O), 1598, 1440 (C = C), 1354, 1321(2S = O), 1185 (SO2-NH), 1111, 1094 (C-N, C-O). 1H NMR (500 MHz, DMSO-d6) δ: 7.89 (t,J = 6.3 Hz, 1H, NH), 7.64 (d, J = 8.6 Hz, 2H, ArH), 7.33 (d, J = 8.05 Hz, 2H, ArH), 3.51 (d,J = 5.7 Hz, CH2), 2.34 (s, 3H, CH3). 13C NMR (500 MHz, DMSO-d6) δ: 170.8 (C = O), 143.1, 138.4, 130.0, 127.1 (aromatic carbons), 44.3 (CH2), 21.5 (CH3). HRMS-ESI (m/z): 228.0410(M-H)-, calculated, 228.0408.
86% With sodium hydrogencarbonate In water; acetone at 25℃; for 0.25 h; General procedure: Sulfonyl chloride (0.20 mmol) was dissolved in acetone (2 mL) and the resulting solution was injected in the reagent loop A. An aqueous NaHCO3 0.4 M (1 mL) was added to a solution of the amine (0.22 mmol) dissolved in PEG-400 (1 mL). The H2O/PEG400 solution (2 mL, 1:1,v/v) was then injected in the reagent loop B. A degassed solution of acetone and water were connected with pump A and B, respectively, and the flow rate was fixed at 0.5 mL min−1 (0.25 mL min−1 + 0.25 mL min−1). After switching the sample loops, the mixtures exited were joined in a T-piece, entered in a 10 mL PTFE coil reactor warmed at 25 °C, fitted with the back pressure regulator (100 psi), directed in UV detector and the output was recovered in a fraction collector. The reaction mixture was drooped in a tube containing Et2O/HCl 3 N (5 mL, 4:1, v/v). The two phases were separated, and the organic one was washed with H2O (2 × 1 mL), dried over Na2SO4, and concentrated under reduced pressure to give the desired pure compound.
81% at 20 - 25℃; General procedure: Syntheses of G1 and P1:
To a stirred solution of glycine (0.75 g, 10.0 mmol) or l-phenylalanine (1.65 g, 10.0 mmol) in 20 mL of 1 M NaOH solution at 25 °C, p-toluenesulfonyl chloride (1.91 g, 10.0 mmol) was added.
After overnight stirring at room temperature, the solid residue was filtered off and the aqueous reaction portion was acidified with 1 M HCl.
The obtained solid was filtered and purified by column chromatography on silica with hexane and EtOAc (1:2) to obtain compounds G1 and P1 as white solids. (Yields, 81percent and 76percent, respectively.)
Compound G1: Yield 81percent as white solid. 1H NMR (400 MHz, DMSO-d6): δ 12.66 (broad singlet, 1H, -COOH), 7.93 (t, J = 6.1 Hz, 1H, -NH-), 7.67 (d, J = 8.4 Hz, 2H, ArH), 7.37 (d, J = 8.3 Hz, 2H, ArH), 3.54 (d, J = 6.1 Hz, 2H, -CH2-), 2.37 (s, 3H, -CH3) ppm. 13C NMR (100 MHz, CDCl3): δ 171.1, 143.8, 136.3, 129.9, 127.3, 40.3, 21.6 ppm. Anal. Calcd [C9H11NO4S]: C, 47.15; H, 4.84; N, 6.11; S, 13.99. Found: C, 48.36; H, 5.11; N, 5.93; S, 14.27.
72%
Stage #1: With sodium carbonate In water at 70 - 85℃; for 0.75 h;
Stage #2: With hydrogenchloride In water at 20℃;
General procedure: The nitrogen tosylation was done using a reported procedure. In a round bottom flask, 2.4 equiv. of Na2CO3 was dissolved in 70 °C water (C = 0.66 mol/L). Then 1.0 equiv. of the desired anthranilic acid was added followed by 1.4 equiv. of tosyl chloride. The suspension was stirred at 70 °C for 40 min then at 85 °C for 5 min. The reaction mixture was then directly filtrated and the solid washed with 85 °C water. The filtrate was cooled to room temperature and then acidified to pH = 1 using an aqueous 6M HCl solution. The precipitated solid was collected by suction and dried over vacuum. The resulting tosyl anthranilic acids were used without further purification.
21%
Stage #1: With sodium hydroxide In diethyl ether; water at 20℃; for 3.16667 h;
Stage #2: With hydrogenchloride In water
Glycine (1 g, 13.32 mmol) was dissolved in IN NaOH (aq.) and a solution of tosyl chloride (2.62 g, 13.72 mmol) in diethyl ether (15 ml) was added portion wise with stirring over 10 min. The resulting mixture was allowed to stir at room temperature for 3 h. The ethereal layer was separated and the aqueous layer treated with 2N HCl solution until acidified to pH 5. After cooling the resulting solution to 0 0C, the product began to precipitate from the solution. The solid was collected by filtration and the mother liquor placed in a fridge overnight causing more of the desired product to precipitate. The solid was again collected by filtration and the combined collected solid was dried under high vacuum affording 9 as a white powder (613 mg, 21percent). δH (400 MHz, MeOD) 2.41 (3H, s, CH3), 3.66 (2H, S5 CH2), 7.35 (2H, d, J=8 Hz5 ArH)5 7.73 (2H5 d, J=8 Hz, ArH); δc (100.6 MHz, MeOD) 20.3, 43.6, 127.0, 129.5, 137.6, 143.6, 171.0; MS (ES+) 246.8 (100percent, [M+H20]+); MS (ES') 227.9 (100percent, [M-H]-); HRMS [M-H]' requires 228.03360, found 228.03364.

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  • [ 15707-34-3 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708
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  • [ 13360-65-1 ]
  • [ 17398-16-2 ]
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  • [ 13925-09-2 ]
  • [ 13925-08-1 ]
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  • [ 15707-34-3 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708
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YieldReaction ConditionsOperation in experiment
11.2 g With sodium hydroxide In water at 15 - 26℃; for 1.5 h; To a stirred and cooled (15 °C) solution of glycine (5.0 g, 66.602 mmol) in 10percent aqueous sodium hydroxide solution (50 mL) was added benzoyl chloride (11.8 mL, 92.57 mmol) in portions. The reaction mixture was stirred at RT for 1.5 h. The reaction mixture was poured in to crushed ice and acidified with conc. HC1 till pH 3-4.The obtained precipitate was collected by filtration and dried to yield 11.2 g of thetitle product as a solid. ‘H NMR (300 MHz, DMSO-d6) ö 4.08 (s, 2H), 7.49 (d, J = 8.7Hz, 2H), 7.85 (d, J = 8.1 Hz, 2H), 8.00 (d, J = 8.4 Hz, 1H).
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YieldReaction ConditionsOperation in experiment
86% at 0℃; Reflux Glycine (lg, 13.3 mmol) was dissolved in isopropanol (10 mL) at 0°C. SOCl2 (1.93 mL, 26.6 mmol) was added dropwise. The mixture was stirred at reflux overnight. After cooling, the solvent was evaporated under reduced pressure and hexane was added at 0°C. The suspension was filtered to afford the product (1.76 g, 86percent) as a white solid. NMR (300 MHz, MeOD) δ 5.13 (hept, J = 6.3 Hz, 1H, (CH3)2CHO), 3.81 (s, 2H, CH2), 1.32 (s, 3H, (CH3 2CHO . 1.30 (s, 3H, iCH3}2CHO). 13C NMR (75 MHz, MeOD) δ 168.0 (C), 71.7 ((CH3)2CHO), 41.2 (CH2), 21.9 ((CH3 2CHO . HRMS [M+H]+ C5H12NO2: Calcd. 1 18.0858 found 1 18.0863.
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