bis((methylsulfanyl)methanimidamide); sulfuric acid

• ChemBase ID: 78049
• Molecular Formular: C4H14N4O4S3
• Molecular Mass: 278.37336
• Monoisotopic Mass: 278.01771795
• SMILES: S(=O)(=O)(O)O.S(C(=N)N)C.S(C(=N)N)C
• Canonical SMILES: OS(=O)(=O)O.CSC(=N)N.CSC(=N)N
• InChI: InChI=1S/2C2H6N2S.H2O4S/c2*1-5-2(3)4;1-5(2,3)4/h2*1H3,(H3,3,4);(H2,1,2,3,4)
• InChIKey: BZZXQZOBAUXLHZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis((methylsulfanyl)methanimidamide); sulfuric acid
• IUPAC Traditional name: bis(methylsulfanylmethanimidamide); sulfuric acid
• Synonyms: S-METHYLISOTHIOUREA SULFATE; S-Methylisothiourea sulfate; 2-Methyl-2-thiopseudourea sulfate; S-Methylisothiouronium sulfate; 2-Methyl-2-thiopseudourea hemisulfate; SMT; 2-Methyl-2-thiopseudourea hemisulfate salt; S-Methyl-ITU; S-Methylthiuronium sulfate; S-Methylisothiourea hemisulfate salt; Methyl carbamimidothioate hemisulphate; S-Methyl-2-isothiourea hemisulphate; bis((methylsulfanyl)methanimidamide); sulfuric acid; S-甲基异硫脲硫酸盐; 2-甲基-2-硫代假脲 半硫酸盐; S-甲基-ITU; S-甲基异硫脲硫酸盐; S-甲基异硫脲 半硫酸盐

Database IDs

• CAS Number: 867-44-7
• EC Number: 212-759-7
• MDL Number: MFCD00013055
• Beilstein Number: 3717365; 3917217
• PubChem SID: 24885362; 162042883; 24897262
• PubChem CID: 13347

CALCULATED PROPERTIES

• Acid pKa: -3.034349
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -2.0011563
• LogD (pH = 7.4): -1.9397736
• Log P: 0.4134605
• Molar Refractivity: 34.9793 cm^3
• Polarizability: 9.368552 Å^3
• Polar Surface Area: 49.87 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear, colorless
• Melting Point: 240-241 °C (dec.)(lit.); 242 - 244°C; ca 235°C dec.
• Density: 1.28
• Hydrophobicity(logP): 0.076

Safety Information

• Storage Warning: Hygroscopic; Irritant/Harmful
• RTECS: UM9200000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36-60
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H301; H302
• GHS Precautionary statements: P264-P270-P301+P310-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (T); 95%; 98%; 98+%
• Grade: purum
• Linear Formula: HN=C(NH2)SCH3 · 1/2H2SO4

DETAILS

MP Biomedicals - 05203501

MP Biomedicals Rare Chemical collection

Sigma Aldrich - M84445

Biochem/physiol Actions
More potent than NMMA as an inhibitor of inducible nitric oxide synthetase (iNOS).
Packaging
100, 500 g in poly bottle

Sigma Aldrich - 67730

Biochem/physiol Actions
More potent than NMMA as an inhibitor of inducible nitric oxide synthetase (iNOS).
Other Notes
For the guanidination of free amino groups1,2

REFERENCES

• Precursor of various pyrimidines by condensation with ?-dicarbonyl and related intermediates. For use as a convenient source of methanethiol in the conversion of alkyl halides to methyl sulfides, see: Org. Synth. Coll., 2, 345 (1943).
• Reagent for the conversion of amines to guanidines: J. Am. Chem. Soc., 71, 2476 (1949).