1,1-bis(methylsulfanyl)-2-nitroethene

• ChemBase ID: 86942
• Molecular Formular: C4H7NO2S2
• Molecular Mass: 165.23388
• Monoisotopic Mass: 164.99182047
• SMILES: [N+](=O)(C=C(SC)SC)[O-]
• Canonical SMILES: CSC(=C[N+](=O)[O-])SC
• InChI: InChI=1S/C4H7NO2S2/c1-8-4(9-2)3-5(6)7/h3H,1-2H3
• InChIKey: NXGHEDHQXXXTTP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,1-bis(methylsulfanyl)-2-nitroethene
• IUPAC Traditional name: 1,1-bis(methylsulfanyl)-2-nitroethene
• Synonyms: 2,2-Bis(methylthio)-1-nitroethylene; NSC 241513; Bis(methylthio)-2-nitroethylene; 1,1-Bis(methylsulfanyl)-2-nitroethene; 1,1-Bis(methylthio)-2-nitroethene; 1-Nitro-2,2-bis(methylmercapto)ethylene; 1-Nitro-2,2-bis(methylthio)ethene; 1-Nitro-2,2-bis(methylthio)ethylene; 1,1-Bis(methylthio)-2-nitroethylene; 1,1-bis(methylsulfanyl)-2-nitroethene; 1,1-Di(methylthio)-2-nitroeth-1-ene; 1,1-Bis(methylmercapto)-2-nitroethylene; Nitroketene dimethyl mercaptal; 1,1-Bis(methylthio)-2-nitroethylene; 1,1-双(甲基硫代)-2-硝基乙烯; 硝基乙烯酮二甲基缩硫醛; 1,1-双(甲硫基)-2-硝基乙烯

Database IDs

• CAS Number: 13623-94-4
• EC Number: 237-108-4
• MDL Number: MFCD00010443
• Beilstein Number: 1524538
• PubChem SID: 162074058; 24856905
• PubChem CID: 83623

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.0222254
• LogD (pH = 7.4): 2.0222254
• Log P: 2.0222254
• Molar Refractivity: 50.0878 cm^3
• Polarizability: 15.970607 Å^3
• Polar Surface Area: 43.14 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Pale Yellow Solid
• Melting Point: 124-126°C; 124-127°C; 125-127 °C(lit.); 126 - 127°C
• Hydrophobicity(logP): -0.901

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37; 26-37/39
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (S); 95%; 97%; 98%; 99%
• Grade: purum
• Linear Formula: O2NCH=C(SCH3)2

DETAILS

Sigma Aldrich - 279706

Packaging
25 g in glass bottle

Sigma Aldrich - 15097

Other Notes
Versatile building block for the synthesis of carbo- and heterocyclic compounds1,2,3

Toronto Research Chemicals - B497200

Bis(methylthio)-2-nitroethylene is a synthetic intermediate as well as an impurity of the ulcerostatic agent, Ranitidine (R120000).

REFERENCES

• Beaulieu, N. et al.: J. Pharmac. Sci., 77, 889 (1988)
• By Haywood, P. et al.: J. Chem. Soc. Perk. Trans. Org. Bio-Org. Chem., 5, 951 (1988)