| Identification | More | [Name]
N-P-TOSYLGLYCINE | [CAS]
1080-44-0 | [Synonyms]
(4-METHYLPHENYLSULFONYLAMINO)ACETIC ACID
AURORA 963
N-((4-METHYLPHENYL)SULFONYL)GLYCINE
N-(P-TOLUENE SULFONYL) GLYCINE
N-P-TOSYLGLYCINE
N-TOSYLGLYCINE
OTAVA-BB BB0123400526
P-TOLUENESULFONYLGLYCINE
TOS-GLY-OH
N-4-tosylglycine
N-TOS-Gly-OH
N-(4-Toluenesulfonyl)-glycine
N-(4-TOLUENESULFONYL)-GLYCINE N-P-TOSYLGLYCINE
(Toluene-4-sulfonylamino)-acetic acid
P-toluenesulfonate glycine
Tosylaminoacetic acid | [EINECS(EC#)]
625-711-9 | [Molecular Formula]
C9H11NO4S | [MDL Number]
MFCD00045898 | [Molecular Weight]
229.25 | [MOL File]
1080-44-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
147-149 °C (lit.) | [Boiling point ]
430.0±55.0 °C(Predicted) | [density ]
1.369±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
3.41±0.10(Predicted) | [color ]
White | [CAS DataBase Reference]
1080-44-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [HS Code ]
2935.90.9500 |
| Hazard Information | Back Directory | [Uses]
N-Tosylglycine is a sulfonamide derivative used to synthesize metal complexes which potentially displays antibacterial activity. | [reaction suitability]
reaction type: solution phase peptide synthesis | [Synthesis]
Sodium carbonate (Na2CO3, 1.590 g, 15 mmol) was added to a solution of glycine (12.5 mmol) in water (15 mL) under continuous stirring until completely dissolved. The solution was cooled to -5°C and p-toluenesulfonyl chloride (15 mmol) was added in four batches over 1 hour. The reaction mixture was continued to be stirred at room temperature for about 4 h. The progress of the reaction was monitored using thin layer chromatography (TLC, unfolding agent was MeOH/DCM, 1:9). Upon completion of the reaction, the mixture was acidified with 20% aqueous hydrochloric acid to pH 2. The crystals were collected by diafiltration and washed with pH 2.2 buffer. The pure product 2-(4-methylphenylsulfonamido)acetic acid was dried in a desiccator. The yield was 99.34% (2.8410 g) and the melting point was 88.4-88.6°C. FTIR (KBr, cm-1 ): 3448 (O-H, COOH), 3277 (N-H), 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=6.3 Hz, 1H, NH), 7.65-7.63 (d, J=8.6 Hz, 2H, ArH), 7.34-7.33 (d, J=8.05 Hz, 2H, ArH ), 3.52-3.51 (d, J=5.7 Hz, 2H, CH2), 2.34 (s, 3H, CH3).13C NMR (DMSO-d6) δ: 170.7 (C=O), 143.1, 138.4, 130.0, 127.1 (aryl carbons), 44.3 (CH2), 21.5 (CH3).HRMS-ESI (m/z): 228.0412 ([M-H]-, calculated value: 228.0408). | [References]
[1] European Journal of Medicinal Chemistry, 2017, vol. 135, p. 349 - 369
[2] PLoS ONE, 2018, vol. 13, # 1,
[3] Journal of the American Chemical Society, 2018, vol. 140, # 17, p. 5834 - 5841
[4] Journal of Molecular Catalysis A: Chemical, 2011, vol. 351, p. 41 - 45
[5] Organic and Biomolecular Chemistry, 2018, vol. 16, # 31, p. 5618 - 5625 |
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