2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetic acid

• ChemBase ID: 146650
• Molecular Formular: C6H7N3O3S
• Molecular Mass: 201.20308
• Monoisotopic Mass: 201.0208121
• SMILES: CO/N=C(/c1csc(n1)N)\C(=O)O
• Canonical SMILES: CO/N=C(/c1csc(n1)N)\C(=O)O
• InChI: InChI=1S/C6H7N3O3S/c1-12-9-4(5(10)11)3-2-13-6(7)8-3/h2H,1H3,(H2,7,8)(H,10,11)
• InChIKey: NLARCUDOUOQRPB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetic acid; (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetic acid
• IUPAC Traditional name: (2-amino-1,3-thiazol-4-yl)(methoxyimino)acetic acid; (2Z)-(2-amino-1,3-thiazol-4-yl)(methoxyimino)acetic acid
• Synonyms: 2-Amino-α-(methoxyimino)-4-thiazoleacetic acid, predominantly syn; 2-(2-Amino-4-thiazolyl)-(Z)-2-methoxyiminoacetic Acid; Thiazoximic Acid; syn-2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetic Acid; syn-Thiazoximic Acid; 2-Amino-α-(methoxyimino)-4-thiazoleacetic Acid; 2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetic acid; 2-(2-AMinothiazol-4-yl)-2-(MethoxyiMino)acetic acid; 2-甲氧氨基-2-(2-氨基噻唑)-4-乙酸，主要为顺式

Database IDs

• CAS Number: 65872-41-5
• EC Number: 265-957-0
• MDL Number: MFCD00010416
• PubChem SID: 162240843; 24856932
• PubChem CID: 5486924

CALCULATED PROPERTIES

• Acid pKa: 1.7195702
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -1.9326149
• LogD (pH = 7.4): -2.7207625
• Log P: -0.67329943
• Molar Refractivity: 45.5698 cm^3
• Polarizability: 16.95046 Å^3
• Polar Surface Area: 97.8 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 180-183°C (dec.); 192 - 194°C; 192 °C (dec.)(lit.)
• Hydrophobicity(logP): -0.133

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95%; 97%
• Empirical Formula (Hill Notation): C6H7N3O3S

DETAILS

Sigma Aldrich - 280143

Packaging
5 g in glass bottle

Toronto Research Chemicals - A611965

Intermediate in the preparation of Cephem compounds.

REFERENCES

• Nukaga, M., et al.: J. Biol. Chem., 279, 9344 (2004)
• Kumar, S., et al.: Biochem., 43, 2664 (2004)