| Identification | More | [Name]
tert-Butyl carbazate | [CAS]
870-46-2 | [Synonyms]
AKOS B028820
BOC-HYDRAZIDE
BOC-HYDRAZINE
BOC-NHNH2
+-BUTYL CARBAZATE
CARBAZIC ACID TERT-BUTYL ESTER
CARBAZINIC ACID TERT-BUTYL ESTER
CARBONIC ACID TERT-BUTYL ESTER HYDRAZIDE
HYDRAZINECARBOXYLIC ACID TERT-BUTYL ESTER
LABOTEST-BB LT00053500
N-T-BUTOXYCARBONYL-HYDRAZIDE
T-BOC-HYDRAZIDE
T-BUTOXYCARBONYL HYDRAZIDE
T-BUTYLCARBAZATE
T-BUTYLOXYCARBONYL-HYDRAZIDE
TERT-BOC-HYDRAZIDE
TERT-BUTOXYCARBONYL HYDRAZIDE
TERT-BUTOXYCARBONYLHYDRAZINE
TERT-BUTYLOXYCARBAZATE
tert-butyloxycarbonyl-hydrazide | [EINECS(EC#)]
212-795-3 | [Molecular Formula]
C5H12N2O2 | [MDL Number]
MFCD00007593 | [Molecular Weight]
132.16 | [MOL File]
870-46-2.mol |
| Chemical Properties | Back Directory | [Appearance]
White to pale yellow lumps | [Melting point ]
39-42 °C (lit.) | [Boiling point ]
63-65 °C/0.1 mmHg (lit.) | [density ]
1.02
| [refractive index ]
1.4496 (estimate) | [Fp ]
197 °F
| [storage temp. ]
Store at RT. | [solubility ]
Soluble in ethanol and methanol. | [form ]
Crystalline Lumps | [pka]
10.74±0.20(Predicted) | [color ]
White to slightly yellow | [Sensitive ]
Moisture Sensitive | [BRN ]
1756967 | [InChIKey]
DKACXUFSLUYRFU-UHFFFAOYSA-N | [CAS DataBase Reference]
870-46-2(CAS DataBase Reference) | [EPA Substance Registry System]
870-46-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T-F,T,F | [Risk Statements ]
R48:Danger of serious damage to health by prolonged exposure.
R36/37/38:Irritating to eyes, respiratory system and skin .
R24/25:Toxic in contact with skin and if swallowed .
R11:Highly Flammable. | [Safety Statements ]
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S16:Keep away from sources of ignition-No smoking . | [RIDADR ]
1325 | [WGK Germany ]
3
| [F ]
21 | [TSCA ]
Yes | [HazardClass ]
4.1 | [PackingGroup ]
III | [HS Code ]
29280090 |
| Hazard Information | Back Directory | [Chemical Properties]
White to pale yellow lumps | [Uses]
Starting material for preparing BOC-azide, a reagent to introduce the BOC amino protection. | [Synthesis Reference(s)]
Journal of the American Chemical Society, 82, p. 2725, 1960 DOI: 10.1021/ja01496a018
Chemical and Pharmaceutical Bulletin, 18, p. 217, 1970 DOI: 10.1248/cpb.18.217 | [Synthesis]
General procedure for the synthesis of tert-butyl hydrazinecarboxylate from di-tert-butyl dicarbonate: Hydrazine hydrate (113 mg, 2.26 mmol, 2.26 eq.) was dissolved in isopropanol (IPA, 5 mL) and the solution was cooled to 0 °C. Subsequently, di-tert-butyl dicarbonate (174 mg, 1 mmol, 1 eq.) dissolved in isopropanol (IPA, 1 mL) was added dropwise. The reaction mixture was stirred at 0 °C for 2 hours. After completion of the reaction, the solvent was removed by rotary evaporator. The residue was dissolved in dichloromethane (DCM) and dried with anhydrous magnesium sulfate (MgSO4). After drying, the desiccant was removed by filtration and the solvent was again removed by rotary evaporator to give tert-butylhydrazine carboxylate (10) as a white semi-solid (128 mg, 97% yield). The product was confirmed by nuclear magnetic resonance hydrogen spectrum (1H NMR, 300 MHz, CDCl3): δ 6.73 (s, 1H), 3.83 (s, 2H), 1.46 (s, 9H); nuclear magnetic resonance carbon spectrum (13C NMR, 75 MHz, CDCl3): δ 158.2, 80.1, 28.2. | [Purification Methods]
Distil it in a Claisen flask with a water or oil bath at ca 80o. After a couple of drops have distilled, the carbazate is collected as an oil which solidifies to a snow white solid. It can be crystallised with 90% recovery from a 1:1 mixture of pet ether (b 30-60o) and pet ether (b 60-70o). [Carpino et al. Org Synth Coll Vol V 166 1973, Caprino et al. Org Synth 44 20 1964, Beilstein 3 IV 175.] | [References]
[1] European Journal of Medicinal Chemistry, 2012, vol. 54, p. 33 - 41
[2] Tetrahedron Letters, 2015, vol. 56, # 48, p. 6653 - 6655
[3] Journal of Inorganic Biochemistry, 2013, vol. 127, p. 188 - 202
[4] Organic and Biomolecular Chemistry, 2017, vol. 15, # 43, p. 9071 - 9076
[5] Journal of Materials Chemistry B, 2017, vol. 5, # 19, p. 3565 - 3571 |
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