4-[2-(1,3-benzothiazol-2-ylsulfanyl)-1-(methoxyimino)-2-oxoethyl]-1,3-thiazol-2-amine

• ChemBase ID: 137698
• Molecular Formular: C13H10N4O2S3
• Molecular Mass: 350.4391
• Monoisotopic Mass: 349.99658858
• SMILES: CO/N=C(/c1csc(n1)N)\C(=O)Sc1nc2ccccc2s1
• Canonical SMILES: CO/N=C(/c1csc(n1)N)\C(=O)Sc1nc2c(s1)cccc2
• InChI: InChI=1S/C13H10N4O2S3/c1-19-17-10(8-6-20-12(14)15-8)11(18)22-13-16-7-4-2-3-5-9(7)21-13/h2-6H,1H3,(H2,14,15)
• InChIKey: COFDRZLHVALCDU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[2-(1,3-benzothiazol-2-ylsulfanyl)-1-(methoxyimino)-2-oxoethyl]-1,3-thiazol-2-amine; 4-[(1Z)-2-(1,3-benzothiazol-2-ylsulfanyl)-1-(methoxyimino)-2-oxoethyl]-1,3-thiazol-2-amine
• IUPAC Traditional name: 4-[2-(1,3-benzothiazol-2-ylsulfanyl)-1-(methoxyimino)-2-oxoethyl]-1,3-thiazol-2-amine; 4-[(1Z)-2-(1,3-benzothiazol-2-ylsulfanyl)-1-(methoxyimino)-2-oxoethyl]-1,3-thiazol-2-amine
• Synonyms: S-2-Benzothiazolyl-2-amino-α-(methoxyimino)-4-thiazolethiolacetate; (αZ)-2-Amino-α-(methoxyimino)-4-thiazoleethanethioic Acid S-2-Benzothiazolyl Ester; (Z)-2-Amino-α-(methoxyimino)-4-thiazoleethanethioic Acid S-2-Benzothiazolyl Ester; (Z)-2-[Methoxyimino]-2-(2-aminothiazol-4-yl)acetic Acid S-2-Benzothiazole Ester; S-(Benzothiazol-2-yl) (Z)-(2-Aminothiazol-4-yl)(methoxyimino)thioacetate; S-2-Benzothiazolyl-2-amino-α-(methoxyimino)-4-thiazolethiolacetate; AE-活性酯

Database IDs

• CAS Number: 80756-85-0
• EC Number: 279-540-6
• MDL Number: MFCD00129148
• PubChem SID: 162231960; 24862004
• PubChem CID: 5702580

CALCULATED PROPERTIES

• Acid pKa: 16.336939
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 4.1089473
• LogD (pH = 7.4): 4.114046
• Log P: 4.1141114
• Molar Refractivity: 87.1038 cm^3
• Polarizability: 34.296062 Å^3
• Polar Surface Area: 90.46 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 125-127°C; 128-130 °C(lit.)

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere
• RTECS: XJ4664500
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• 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: 97%
• Empirical Formula (Hill Notation): C13H10N4O2S3

DETAILS

Sigma Aldrich - 360856

Packaging
25 g in glass bottle

Toronto Research Chemicals - B206760

Reagent used in the synthesis of Cefotaxime and related derivatives, such as: Ceftriaxone (C245000).

REFERENCES

• Heinze-Krauss, I., et al.: J. Med. Chem., 39, 1864 (1996)
• Bharathi, C., et al.: J. Pharm. Biomed. Anal., 43, 733 (1996)
• Gupta, V., et al.: Anal. Bioanal. Chem., 390, 2171 (1996)