tetrabutylazanium; tribroman-2-uide

• ChemBase ID: 129772
• Molecular Formular: C16H36Br3N
• Molecular Mass: 482.17574
• Monoisotopic Mass: 479.03978616
• SMILES: Br[Br-]Br.CCCC[N+](CCCC)(CCCC)CCCC
• Canonical SMILES: CCCC[N+](CCCC)(CCCC)CCCC.Br[Br-]Br
• InChI: InChI=1S/C16H36N.Br3/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;1-3-2/h5-16H2,1-4H3;/q+1;-1
• InChIKey: XXSLZJZUSYNITM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tetrabutylazanium; tribroman-2-uide
• IUPAC Traditional name: tetrabutylammonium; tribroman-2-uide
• Synonyms: TBABr3; Tetrabutylammonium bromide perbromide; Tetrabutylammonium tribromide; TBAB; Tetra-n-butylammonium tribromide; Tetrabutylammonium tribromide; N,N,N,N-Tetrabutylammonium tribromide; 四丁基溴化胺二溴; 四丁基三溴化铵; 四正丁基三溴化铵

Database IDs

• CAS Number: 38932-80-8
• MDL Number: MFCD00012110
• Beilstein Number: 3746114
• PubChem SID: 162224060; 24888816; 24858199
• PubChem CID: 2723680
• Chemspider ID: 2005880
• Wikipedia Title: Tetrabutylammonium_tribromide

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

• Apperance: Crystalline; pale orange solid
• Melting Point: 71-76 °C; 71-76 °C(lit.); 74-76°C

Safety Information

• European Hazard Symbols: Corrosive (C); Irritant (Xi)
• UN Number: UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: III
• Risk Statements: 34; 36/37/38
• Safety Statements: 26-36; 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H314-H318; H315-H319-H335
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (RT); 95+%; 98%
• Grade: purum
• Linear Formula: (CH3CH2CH2CH2)4NBr3

DETAILS

Sigma Aldrich - 301590

Packaging
25, 100 g in glass bottle

Sigma Aldrich - 86902

Other Notes
Brominating agent1,2,3,4; Hofmann degradation of amides to ureas and carbamates5

REFERENCES

• Mild brominating agent. Alkenes are converted to vic-dibromides in high yields. In ethylene glycol, ketones can be converted directly to ɑ-bromo ethylene acetals in good yield, providing convenient access to ɑ,?-unsaturated ketones: Bull. Soc. Chim. Belg., 93, 157 (1984); Synth. Commun., 15, 213 (1985). Aromatic amines and phenols are selectively brominated in the p-position: Synth. Commun., 16, 1641 (1986); Can. J. Chem., 67, 2061 (1989); J. Chem. Res. (Synop.), 381 (1986); Tetrahedron Lett., 39, 8163 (1998).
• For Hofman rearrangemt of amides to ureas and carbamates, See: Bull. Chem. Soc. Jpn., 61, 1401 (1988).
• In catalytic amounts promotes dithioacetalization of aldehydes and ketones, and transthioacetalization of 1,3-dioxolanes and dioxanes with ethane- or propanedithiol: Org. Biomol. Chem., 2, 1670 (2004); the cleavage of dithioacetals to the corresponding carbonyl compounds with stoichiometric amounts of the reagent has also been described: Synlett, 785 (2001). Also catalyzes both the protection and deprotection of carbonyl compounds to 1,3-dithiolanes: Tetrahedron. Lett., 43, 2843 (2002), of aldehydes to 1,1-diacyloxy derivatives: Eur. J. Org. Chem., 441 (2005), and alcohols to tetrahydropyranyl (THP) ethers: Tetrahedron Lett., 42, 7679 (2001). In methanol, t-butyldimethylsilyl (TBDMS), THP, and 4,4'-dimethoxytrityl ethers undergo catalytic deprotection. The reaction is chemoselective, permitting, e.g. selective deprotection of primary DMT, TBDMS, and THP ethers in the presence of other ether protecting groups: Org. Lett., 2, 4177 (2000).
• For a brief feature on uses of this reagent in Organic synthesis, see: Synlett, 2681 (2006).