ethoxycarbohydrazide

• ChemBase ID: 83109
• Molecular Formular: C3H8N2O2
• Molecular Mass: 104.10782
• Monoisotopic Mass: 104.05857751
• SMILES: O=C(NN)OCC
• Canonical SMILES: CCOC(=O)NN
• InChI: InChI=1S/C3H8N2O2/c1-2-7-3(6)5-4/h2,4H2,1H3,(H,5,6)
• InChIKey: VYSYZMNJHYOXGN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethoxycarbohydrazide
• IUPAC Traditional name: ethoxycarbohydrazide
• Synonyms: Hydrazinocarboxylic acid ethyl ester; Ethyl carbazate; Ethyl carbazate; Ethyl hydrazinecarboxylate; Ethoxycarbonylhydrazine; Ethyl hydrazinocarboxylate; 乙氧基甲酰肼; 肼基甲酸乙酯

Database IDs

• CAS Number: 4114-31-2
• EC Number: 223-903-3
• MDL Number: MFCD00007595
• Beilstein Number: 878265
• PubChem SID: 24878267; 162070228; 24894429
• PubChem CID: 20064

CALCULATED PROPERTIES

• Acid pKa: 12.94085
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.35136285
• LogD (pH = 7.4): -0.35067484
• Log P: -0.35066494
• Molar Refractivity: 25.3222 cm^3
• Polarizability: 9.667854 Å^3
• Polar Surface Area: 64.35 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 44-47 °C(lit.); 44-47°C; 44-47°C; 44-48 °C
• Boiling Point: 108-110 °C/22 mmHg(lit.); 108-110°C; 85-86°C/7mm
• Flash Point: 186.8 °F; 86 °C; 86°C; 86°C(186°F)

Safety Information

• Storage Warning: Irritant; Moisture Sensitive
• RTECS: FE2545000
• European Hazard Symbols: Toxic (T)
• UN Number: UN2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: III
• Risk Statements: 25-36/37/38
• Safety Statements: 26-36/37-45; 26-45
• TSCA Listed: 是
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H315-H319-H335; H301-H315-H319-H335
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338; P280H-P305+P351+P338-P309-P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Purity: ≥97.0% (GC); 97%
• Grade: purum
• Impurities: ≤3% water
• Linear Formula: H2NNHCO2C2H5

DETAILS

Sigma Aldrich - E16503

Packaging
25 g in glass bottle

REFERENCES

• Forms crystalline ethoxycarbonyl hydrazones with aldehydes and ketones. With o-acylphenols, Pb(OAc)₄ treatment of the resulting hydrazone results in replacement of the phenolic OH with ethoxycarbonyl, providing a route to ethyl o-acylbenzoates: Tetrahedron Lett ., 31, 6781 (1990).
• Reaction with methyl ketones, followed by treatment with SOCl₂, leads to 4-substituted 1,2,3-thiadiazoles: J. Am. Chem. Soc., 77, 5359 (1955). In the presence of base, these readily lose N₂ to give alkynethiolates: Can. J. Chem., 46, 1057 (1968):
  
• More recently, this sequence has been used in the synthesis of dendrimers from 1,3,5-triacetylbenzene: J. Chem. Soc., Perkin 1, 2203 (1994).