tetrabutylazanium bromide

• ChemBase ID: 70077
• Molecular Formular: C16H36BrN
• Molecular Mass: 322.36774
• Monoisotopic Mass: 321.20311216
• SMILES: [N+](CCCC)(CCCC)(CCCC)CCCC.[Br-]
• Canonical SMILES: CCCC[N+](CCCC)(CCCC)CCCC.[Br-]
• InChI: InChI=1S/C16H36N.BrH/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H/q+1;/p-1
• InChIKey: JRMUNVKIHCOMHV-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: tetrabutylazanium bromide
• IUPAC Traditional name: tetrabutylammonium ion bromide; tetrabutylammonium bromide
• Synonyms: Aliquat 100; Tetra-n-butylammonium bromide; Tetrabutylammonium bromide solution; Tetrabutylammonium bromide; Tetrabutylammonium bromide; Aliquat® 100; Tetra-n-butylammonium bromide; Tetrabutylammonium bromide; TBAB; Tetra-N-Butylammonium Bromide; 四正丁基溴化铵; 四丁基溴化铵 溶液; 四丁基溴化铵; 四丁基溴化铵

Database IDs

• CAS Number: 1643-19-2
• EC Number: 231-791-2; 216-699-2
• MDL Number: MFCD00011633
• Beilstein Number: 3570983; 6882753
• PubChem SID: 24866693; 24888772; 24869946; 24888786; 24851583; 162035802
• PubChem CID: 74236
• CHEBI ID: 51993
• CHEMBL: 60696
• Chemspider ID: 66843
• Wikipedia Title: Tetra-n-butylammonium_bromide

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

• Solubility: ethanol: soluble100 mg/mL, clear, colorless; ethanol: soluble50 mg/mL, clear, colorless to light yellow; H2O: soluble0.1 g/mL, clear, colorless
• Apperance: White solid
• Melting Point: 101-105 °C; 101-105°C; 102-106 °C; 102-106 °C(lit.); 103 °C; 103-104°C
• Boiling Point: 102 °C
• Density: 1.039 g/mL at 25 °C; 1.15
• Refractive Index: n20/D 1.422
• Absorption Wavelength: λ: 240 nm Amax: 0.04; λ: 250 nm Amax: 0.03; λ: 260 nm Amax: 0.02; λ: 500 nm Amax: 0.02

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Hygroscopic; IRRITANT; Irritant
• European Hazard Symbols: X; Irritant (Xi)
• German water hazard class: 2; 3
• Risk Statements: 22-36/37/38; 36/37/38; R20 R22 R36 R37 R38
• Safety Statements: 26; 26-36; 26-36/37-60; S26 S36
• TSCA Listed: false; 是
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• Main Hazard: Harmful
• GHS Hazard statements: H301-H315-H319-H335; H315-H319-H335
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Gloves

Product Information

• Purity: >98%; ≥98.0%; ≥98.0% (AT); ≥99.0%; ≥99.0% (AT); 95+%; 98%; 98+%
• Concentration: ~50% in H2O; 50 wt. % in H2O
• Grade: ACS reagent; for electrochemical analysis; for ion pair chromatography; p.a.; puriss.; puriss. p.a.; purum; ReagentPlus®
• Suitability: corresponds to standard for filter test
• Impurities: ≤0.5% tributylamine; ≤0.5% tributylamine hydrobromide
• Quality Level: PREMIUM
• Quality: ampule
• λ: 10 % in H2O; in concentrate
• Linear Formula: (CH3CH2CH2CH2)4N(Br)

DETAILS

MP Biomedicals - 02152101

Purity: >98% Phase transfer catalyst C16H36NBr MW 322.4

Sigma Aldrich - 462144

Packaging
1 L in poly bottle

Sigma Aldrich - 86846

Packaging
concentrate in ampules for 6x1 l 0.005 M ready-to-use solution

Sigma Aldrich - 86836

General description
Visit our Sensor Applications portal to learn more.

Sigma Aldrich - 81789

Legal Information
Aliquat is a registered trademark of BASF

Sigma Aldrich - 193119

Packaging
25, 100, 500 g in poly bottle
5 kg in fiber drum
5 kg, 25 kg packaged in open-head fiber drums; 25 g, 100 g, 500 g packaged in poly bottles
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 426288

Packaging
100 g in poly bottle
25 g in glass bottle

REFERENCES

• K salts of ω-bromocarboxylic acids can be cyclized to lactones under effectively "high-dilution" conditions by extracting into toluene in the presence of a small amount of catalyst. The 16-membered ring lactone was formed in 92% yield: J. Org. Chem., 48, 1533 (1983).
• Primary alkyl chlorides can be converted to alcohols in excellent yield by phase-transfer reaction with sodium formate and hydrolysis of the resulting formate esters: Synthesis, 763 (1986).
• Has been used as an "ionic liquid" in the regioselective O-alkylation of ambident nucleophiles: Tetrahedron Lett., 33, 4435 (1992). A method is described whereby the "solvent" can be recovered quantitatively. A semi-molten mixture with KF or CsF has been found to be an effective system for fluorodehalogenation of, e.g., benzyl bromide: J. Fluorine Chem., 73, 185 (1995).
• Effective catalyst for amination reactions of alkyl or activated aryl halides, by increasing the solubility of ammonia in organic media: J. Chem. Soc., Chem. Commun., 267 (1987).
• An improved procedure for the Curtius rearrangement involves reaction of acid chlorides with azide ion under phase-transfer conditions: Synthesis, 38 (1983).
• Aromatic carboxamides undergo N-alkylation with alkyl halides using KOH under solvent-free conditions: Synth. Commun., 22, 1661 (1992).
• Phase-transfer catalyst of wide application. Some illustrative examples are given below. See also Appendix 2.
• ?-Lactones are formed by the cyclization of ?-bromoacids under phase-transfer conditions: Chem. Pharm. Bull., 29, 1063 (1981).