(tert-butoxy)carbohydrazide

• ChemBase ID: 69919
• Molecular Formular: C5H12N2O2
• Molecular Mass: 132.16098
• Monoisotopic Mass: 132.08987763
• SMILES: C(=O)(NN)OC(C)(C)C
• Canonical SMILES: NNC(=O)OC(C)(C)C
• InChI: InChI=1S/C5H12N2O2/c1-5(2,3)9-4(8)7-6/h6H2,1-3H3,(H,7,8)
• InChIKey: DKACXUFSLUYRFU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (tert-butoxy)carbohydrazide
• IUPAC Traditional name: tert-butoxycarbohydrazide
• Synonyms: tert-Butoxycarbonyl hydrazide; Boc-hydrazide; tert-Butyl carbazate; tert-butyl hydrazinecarboxylate; tert-Butyl carbazate; Boc-hydrazine; tert-Butoxycarbonylhydrazine; Boc-肼; 叔丁氧羰基肼; 肼基甲酸叔丁酯

Database IDs

• CAS Number: 3346-63-2; 870-46-2
• EC Number: 212-795-3
• MDL Number: MFCD00007593
• Beilstein Number: 1756967
• PubChem SID: 162035644; 24851826; 24892122
• PubChem CID: 70091

CALCULATED PROPERTIES

• Acid pKa: 13.11165
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.3457911
• LogD (pH = 7.4): 0.34647724
• Log P: 0.34648678
• Molar Refractivity: 34.3792 cm^3
• Polarizability: 13.3093605 Å^3
• Polar Surface Area: 64.35 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 37-41°C; 38-42 °C; 39-42 °C(lit.)
• Boiling Point: 63-65 °C/0.1 mmHg(lit.); 63-65°C/0.1mm
• Flash Point: 197.6 °F; 91°C(195°F); 92 °C

Safety Information

• Storage Warning: IRRITANT; Moisture Sensitive
• European Hazard Symbols: Flammable (F)
• UN Number: UN1325
• German water hazard class: 3
• Hazard Class: 4.1
• Packing Group: III
• Risk Statements: 11
• Safety Statements: 33
• TSCA Listed: false; 是
• GHS Pictograms: GHS02
• GHS Hazard statements: H228
• GHS Precautionary statements: P210-P241-P280-P240-P370+P378A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (GC); 95+%; 97%; 98%; 98+%
• Grade: purum
• Linear Formula: (CH3)3COCONHNH2

DETAILS

Sigma Aldrich - B91005

Packaging
5, 25, 100, 500 g in poly bottle
Application
Employed in a palladium-catalyzed cross-coupling with vinyl halides leading to N-Boc-N-alkenylhydrazines.1Reagent used in solid phase peptide synthesis2 and in α-amino aldehyde optical purity determinations.3 Condenses with aldehydes to form hydrazones which are intermediates in the synthesis of HIV-1 protease inhibitors.4

Sigma Aldrich - 19740

Other Notes
Starting material for preparing BOC-azide, a reagent to introduce the BOC amino protection; E. Wünsch in Houben-Weyl, Vol. 15/1, Synthese von grossen Peptiden, p. 112.; Reagent for the synthesis of sulfonic and carboxylic hydrazides1

REFERENCES

• Monoalkylhydrazines can be prepared via reduction of Boc-hydrazones with borane-THF, and cleavage with HCl: J. Org. Chem., 46, 5413 (1981).
• Protected hydrazine derivative, permitting selective reaction at one N atom, followed by mild acidic cleavage of the Boc group. For preparation of, e.g. N-aminosuccinimide, free from the cyclic hydrazide, see: J. Org. Chem., 37, 2040 (1972). Similarly, reaction with carbonyl or sulfonyl halides, followed by cleavage with HCl, provides a route to monoacyl hydrazides: Synthesis, 244 (1980). It is also commonly used in the synthesis of aza-amino acids; see, for example: Synthesis, 141 (1991) and references therein.
• Precursor of the somewhat unstable tert-butyl azidoformate, useful for introduction of the Boc protecting group, see: Org. Synth. Coll., 5, 157 (1973). Caution! Possible violent decomposition of this azide on heating.