ethyl N-carbothioylcarbamate

• ChemBase ID: 7819
• Molecular Formular: C4H5NO2S
• Molecular Mass: 131.153
• Monoisotopic Mass: 131.00409941
• SMILES: C(=O)(N=C=S)OCC
• Canonical SMILES: CCOC(=O)N=C=S
• InChI: InChI=1S/C4H5NO2S/c1-2-7-4(6)5-3-8/h2H2,1H3
• InChIKey: BDTDECDAHYOJRO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl N-carbothioylcarbamate
• IUPAC Traditional name: ethyl N-carbothioylcarbamate
• Synonyms: Ethoxycarbonyl isothiocyanate; ethyl N-(sulfanylidenemethylidene)carbamate; Carbethoxyisothiocyanate; Carbonic Acid Ethyl Ester Isothiocyanate; Ethoxycarbonyl Mustard Oil; NSC 158480; Carbon(isothiocyanatidic)acid Ethyl Ester; Ethoxycarbonyl isothiocyanate; Ethyl isothiocyanatoformate; Ethoxycarbonyl isothiocyanate; Ethyl carbonisothiocyanatidate; 异硫氰酰甲酸乙酯; 乙氧羰基异硫氰酸酯; 异硫氰酸乙氧羰酯

Database IDs

• CAS Number: 16182-04-0
• EC Number: 240-318-9
• MDL Number: MFCD00004814
• Beilstein Number: 606091
• PubChem SID: 160971126; 24851737
• PubChem CID: 85320

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.3585781
• LogD (pH = 7.4): 1.3585781
• Log P: 1.3585781
• Molar Refractivity: 32.1705 cm^3
• Polarizability: 12.773131 Å^3
• Polar Surface Area: 38.66 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ether
• Apperance: Light Yellow Oil
• Boiling Point: 44-46°C/10mm; 51-55°C @13mm; 56 °C/18 mmHg(lit.); 56°C/18mm
• Flash Point: 122 °F; 50 °C; 50°C; 50°C(122°F)
• Density: 1.110; 1.112; 1.112 g/mL at 25 °C(lit.)
• Refractive Index: 1.5000; 1.5030; n20/D 1.500(lit.)
• Hydrophobicity(logP): 1.938

Safety Information

• Storage Warning: Flammable/Toxic/Harmful/Irritant/Corrosive/Lachrymatory/Moisture Sensitive/Keep Cold/Store under Argon; IRRITANT, LACHRYMATOR; Moisture Sensitive
• European Hazard Symbols: Corrosive (C); Toxic (T); X
• UN Number: 2929; UN2924
• German water hazard class: 3
• Hazard Class: 3; 6.1
• Packing Group: 2; III
• Risk Statements: 10-20/21/22-34; 23-36/37/38-42
• Safety Statements: 23-26-36/37/39-45; 9-20-23-26-36/37/39-45-60
• TSCA Listed: false; 否
• GHS Pictograms: GHS02; GHS05; GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H315-H317-H319-H331-H334-H335; H301-H311-H332-H314-H318-H226
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P305+P351+P338-P361-P405-P501A; P261-P280-P305 + P351 + P338-P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2929 6.1/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (GC); 95%; 97%; 98%
• Grade: purum
• Linear Formula: SCNCOOCH2CH3

DETAILS

Sigma Aldrich - 196126

Packaging
5, 25 g in glass bottle
Application
Versatile reagent used to synthesize thiocarbamides from stannylarenes,1 1,3,5-triazin-2-one-4-thiones from 2-amino-2-oxazolines,2 and N-acylthioureas fromaminodeoxy sugars.3

REFERENCES

• Useful building block in the synthesis of various heterocycles. For a review, see: Synthesis, 301 (1975). For use in synthesis of 1,2,4-oxadiazolidine-3,5-dione, see: Synthesis, 265 (1991):