tetrabutylazanium boranuide

• ChemBase ID: 150014
• Molecular Formular: C16H39BN
• Molecular Mass: 256.29856
• Monoisotopic Mass: 256.31755565
• SMILES: [BH3-].CCCC[N+](CCCC)(CCCC)CCCC
• Canonical SMILES: CCCC[N+](CCCC)(CCCC)CCCC.[BH3-]
• InChI: InChI=1S/C16H36N.BH4/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H4/q+1;-1
• InChIKey: GMBOFJFPOCGSOI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tetrabutylazanium boranuide
• IUPAC Traditional name: tetrabutylammonium boranuide
• Synonyms: Tetra-n-butylammonium tetrahydridoborate; Tetra-n-butylammonium borohydride; Tetrabutylammonium borohydride; 四正丁基硼氢化铵; 四丁基硼氢化铵

Database IDs

• CAS Number: 33725-74-5
• EC Number: 251-658-2
• MDL Number: MFCD00012035
• Beilstein Number: 4212332
• PubChem SID: 162244176; 24853779
• PubChem CID: 9881569

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 1.3234289
• LogD (pH = 7.4): 1.3234289
• Log P: 1.3234289
• Molar Refractivity: 91.3961 cm^3
• Polarizability: 31.734425 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 124-128 °C(lit.); 125-131°C
• Flash Point: 140°C(284°F)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C); Flammable (F)
• UN Number: 3131; UN3131
• German water hazard class: 3
• Hazard Class: 4.3
• Packing Group: 2; II
• Risk Statements: 15-34
• Safety Statements: 26-36/37/39-43; 7/8-26-36/37/39-43-45
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H261-H314; H261-H314-H318
• GHS Precautionary statements: P231 + P232-P280-P305 + P351 + P338-P310-P422; P280-P303+P361+P353-P305+P351+P338-P310-P370+P378I-P402+P404
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3131 4.3/PG 2

Product Information

• Purity: 98%
• Linear Formula: (CH3CH2CH2CH2)4N(BH4)

DETAILS

Sigma Aldrich - 230170

Packaging
10, 50 g in poly bottle
Application
Selective reducing agent for β-ketoamides,1 β-ketoesters,1 and carbohydrate derivatives.2

REFERENCES

• Organic-soluble borohydride. For references to reduction by borohydride, see Sodium borohydride, 35788. Changing the counter ion permits variation in reactivity and selectivity.
• Amides and nitriles are selectively reduced in dichloromethane: Heterocycles, 14, 1437, 1441 (1980); aryl ester, nitro or halo-substituents are unaffected. For the 1,4-reduction of enones, see: Tetrahedron, 37, 1171 (1981). Carboxylic acids can be reduced to alcohols by refluxing in DCM: Synth. Commun., 30, 941 (2000).
• With reactive halides (e.g. MeI) in DCM, provides a convenient source of diborane: Tetrahedron Lett., 3173 (1972). Hydroboration of alkenes has also been effected by refluxing with the reagent in chloroform: Indian J. Chem., 37B, 1186 (1998).
• Effective regent for cleavage of TMS ethers: Synth. Commun., 26, 1065 (1996).
• See also Benzyltriethylammonium borohydride, B24952.