2-cyanoethanethioamide

• ChemBase ID: 86624
• Molecular Formular: C3H4N2S
• Molecular Mass: 100.14226
• Monoisotopic Mass: 100.00951914
• SMILES: N#CCC(=S)N
• Canonical SMILES: NC(=S)CC#N
• InChI: InChI=1S/C3H4N2S/c4-2-1-3(5)6/h1H2,(H2,5,6)
• InChIKey: BHPYMZQTCPRLNR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-cyanoethanethioamide
• IUPAC Traditional name: 2-cyanoethanethioamide
• Synonyms: 2-Cyanoethanethioamide; 2-Cyanothioacetamide; 2-Cyanothioacetamide; 2-cyanoethanethioamide; 2-氰基硫代乙酰胺

Database IDs

• CAS Number: 7357-70-2
• MDL Number: MFCD00010025
• Beilstein Number: 1699934
• PubChem SID: 24856473; 162073740
• PubChem CID: 1416277

CALCULATED PROPERTIES

• Acid pKa: 9.697957
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -0.1902684
• LogD (pH = 7.4): -0.19237746
• Log P: -0.19024143
• Molar Refractivity: 27.7802 cm^3
• Polarizability: 10.666736 Å^3
• Polar Surface Area: 49.81 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 114-120°C; 116-118°C; 118 - 120°C; 118-120 °C(lit.)
• Hydrophobicity(logP): -1.103

Safety Information

• Storage Warning: Light Sensitive; Toxic/Harmful/Light Sensitive
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: 3439; UN3439
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Risk Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39; 9-26-36/37
• TSCA Listed: 否
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H319-H332-H335; H331-H302-H312-H315-H319-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 3439 6.1/PG 3

Product Information

• Purity: 95%; 97%; 98%
• Linear Formula: NCCH2CSNH2

DETAILS

Sigma Aldrich - 272469

Packaging
5, 25 g in glass bottle
Application
Building block for 2-pyridothiones.1,2

REFERENCES

• Cyclocondensation with Benzoyl isothiocyanate, L06964 results in the formation of a pyrimidinedithiol: Chem. Ind. (London), 270 (1988):
  
• See also Methyl isothiocyanate, A11757.
• For a review on the utility of cyanothioacetamide in heterocyclic synthesis, see: Heterocycles, 24, 2023 (1986).