5-(cyanosulfanyl)-2-nitrobenzoic acid

• ChemBase ID: 104434
• Molecular Formular: C8H4N2O4S
• Molecular Mass: 224.19336
• Monoisotopic Mass: 223.98917762
• SMILES: OC(=O)c1c(ccc(SC#N)c1)[N+](=O)[O-]
• Canonical SMILES: N#CSc1ccc(c(c1)C(=O)O)[N+](=O)[O-]
• InChI: InChI=1S/C8H4N2O4S/c9-4-15-5-1-2-7(10(13)14)6(3-5)8(11)12/h1-3H,(H,11,12)
• InChIKey: NQUNIMFHIWQQGJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(cyanosulfanyl)-2-nitrobenzoic acid
• IUPAC Traditional name: 5-(cyanosulfanyl)-2-nitrobenzoic acid
• Synonyms: NTCB; 2-Nitro-5-thiocyanatobenzoic acid; 2-Nitro-5-thiocyanobenzoic acid; 2-NITRO-5-THIOCYANO-BENZOIC ACID; 2-Nitro-5-thiocyanatobenzoic Acid Potassium Salt; 2-硝基-5-硫氰基苯甲酸; 2-硝基-5-氰硫基苯甲酸

Database IDs

• CAS Number: 30344-83-3; 30211-77-9
• EC Number: 250-093-9
• MDL Number: MFCD00007139
• Beilstein Number: 2124001
• PubChem SID: 162091695; 24897806
• PubChem CID: 92266

CALCULATED PROPERTIES

• Acid pKa: 2.1307614
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -1.2729481
• LogD (pH = 7.4): -1.6534214
• Log P: 1.8682127
• Molar Refractivity: 54.5043 cm^3
• Polarizability: 19.451265 Å^3
• Polar Surface Area: 106.91 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: yellow powder
• Melting Point: 156-157 °C(lit.); 159-163 °C

Safety Information

• Storage Condition: 2-8°C, Desiccate
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• 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
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (T); 98%
• Linear Formula: O2NC6H3(SCN)CO2H

DETAILS

MP Biomedicals - 02155929

Yellow powder.

Sigma Aldrich - N7009

包装
1 g in glass bottle
250 mg in glass bottle
Biochem/physiol Actions
2-nitro-5-thiocyanatobenzoic acid (NTCB) is commonly used to cyanylate and cleave proteins at cysteine residues.

Sigma Aldrich - 74040

Other Notes
Reagent for the selective cyanylation of sulfhydryl groups 1; Modifies and cleaves peptides at cysteine residues 2

Toronto Research Chemicals - N565300

Nitro-thiocyanobenzoic acid (NTCB) reactivity of cysteines β100 and β110 in porcine luteinizing hormone.

REFERENCES

• Xing, Y., et al.: J. Biol. Chem., 279, 35437 (2004)
• Fan, Q., et al.: Nature, 433, 269 (2004)