Basic information
- Standard SMILES
CCCC[N+](CCCC)(CCCC)CCCC.O=S(=O)([O-])O- InChIKey
SHFJWMWCIHQNCP-UHFFFAOYSA-M- Molecular formula
- C16H36N.HO4S
- Average molar mass
- 339.5 g/mol
Names & identifiers
- Preferred name
- Tetrabutylammonium hydrogen sulfate
- IUPAC
- hydrogen sulfate;tetrabutylazanium
- English name
- Tetrabutylammonium hydrogen sulfate
- Molecular formula
- C16H37NO4S
- Molecular weight
- 339.53
Names & synonyms
Show more names
Database identifiers
- CAS
32503-27-8- PubChem CID
- 94433
- DTXSID
DTXSID4067690- ChEMBL
CHEMBL1079247- UNII
- KCU8DU7VEL
- EC Number
- 251-068-5
Properties
Computed structural properties
- Topological polar surface area
- 85.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 12
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 192
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 171 · 171-174 °C
- Boiling point
- 213.3 · 213.3-593.92℃[at 101 325 Pa]
- bulk density
- 650 kg/m3 · 650kg/m3
- Density
- 1.01 · 1.01
- vapor pressure
- 0 Pa · 0Pa at 25℃
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 2 O: · H2O: soluble10% (w/v), clear, colorless
- form
- Solution
- color
- White to beige
- Specific Gravity
- 1.01 · 1.01
- Odor
- Amine like
- PH Range
- 1 · 1 - 2
- PH
- 1 · 1-2 (100g/l, H2O, 20℃)
- Water Solubility
- Soluble
- Sensitive
- Hygroscopic
- λmax
- 210 nm · λ: 210 nm Amax: 0.06λ: 220 nm Amax: 0.05λ: 230 nm Amax: 0.03λ: 260 nm Amax: 0.02λ: 500 nm Amax: 0.02
- BRN
- 3599663 · 3599663
- Stability
- Stable, but moisture sensitive. Incompatible with strong oxidizing agents.
- InChI
- 1S/C16H36N.H2O4S/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;1-5(2,3)4/h5-16H2,1-4H3;(H2,1,2,3,4)/q+1;/p-1
- InChIKey
- SHFJWMWCIHQNCP-UHFFFAOYSA-M
- SMILES
- OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC
- LogP
- 0.96 at · 0.96 at 25℃
- CAS DataBase Reference
- 32503 · 32503-27-8(CAS DataBase Reference)
- NIST Chemistry Reference
- Tetrabutylammonium hydrogen sulfate(32503-27-8)
- EPA Substance Registry System
- Tetrabutylammonium sulfate (1:1) (32503-27-8)
- UNSPSC Code
- 12352107 · 12352107
- NACRES
- 21 · NB.21
- Symbol(GHS)
- 5 · GHS05,GHS07
- Signal word
- Danger
- Hazard statements
- 302 · H302-H314-H412
- Precautionary statements
- 260 · P260-P273-P280-P301+P312-P303+P361+P353-P305+P351+P338
- Hazard Codes
- Xn,Xi
- Risk Statements
- 36 · 36/37/38-22
- Safety Statements
- 26 · 26-36-37/39
- WGK Germany
- 3 · 3
- F
- 8 · 8-10
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29239000 · 29239000
- Storage Class
- 8 A · 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- 4 OralAquatic · Acute Tox. 4 OralAquatic Chronic 3Eye Dam. 1Skin Corr. 1
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 0.4% (1 of 231) of reports.
Danger
H302 (90.9%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 231 reports by companies from 28 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 1-Butanaminium, N,N,N-tributyl-, sulfate (1:1)
Status: Active Update: 06-08-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/18908
Tetrabutylammonium hydrogen sulphate: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- F
- 8-10
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29239000
- risk_code
- 36/37/38-22
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07
- hazard_code
- Xn,Xi
- hazard_note
- Irritant
- safety_code
- 26-36-37/39
- Storage Class
- 8A - Combustible corrosive hazardous materials
- Hazard statements
- H302-H314-H412
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralAquatic Chronic 3Eye Dam. 1Skin Corr. 1
- Precautionary statements
- P260-P273-P280-P301+P312-P303+P361+P353-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Purifying or cleansing agents, usually salts of long-chain aliphatic bases or acids, that exert cleansing (oil-dissolving) and antimicrobial effects through a surface action that depends on possessing both hydrophilic and hydrophobic properties.
Uses & manufacturing
Applications
UsesA compound that displays antibacterial properties due to the presence of the quaternary amine and the counter ion. Tetrabutylammonium hydrogen sulfate is an ion pairing reagent that is used in liquid chromatography. It is frequently utilized in the analysis of pharmaceutical compounds and metabolites.
UsesPhase transfer catalyst Tetra-n-butylammonium hydrogen sulfate shows antibacterial properties due to the presence of the quaternary amine and the counter ion. It serves as a phase-transfer catalyst, surface-active agent, solvent, intermediate, active ingredient for conditioners, antistatic agent, detergent sanitizers, softener for textiles and paper products, emulsifying agents and pigment dispersers. Tetrabutylammonium hydrogensulfate is used as a cocatalyst in the synthesis of propionic acid and the ketones by hydrocarboxylation of ethylene. It is also used as an efficient catalyst in the N-alkylation reactions of benzanilides, cyclization of beta-amino acids to beta-lactams, conversion of nitriles to amides, dehydrohalogenation of aryl 2-haloethyl ethers to give vinyl ethers and in the oxidation of alcohols.
General DescriptionTetrabutylammonium hydrogensulfate, a quaternary ammonium salt, is a phase-transfer reagent. It It serves as solvent for the dissolution of ruthenium(II) complex fac-[Ru(CO)2(H2O)3(C(O)C2H5)][CF3SO3]. It participates as a cocatalyst in the reaction medium for the preparation of alternating polyketones and propionic acid.
Preparation methods
PreparationTetrabutylammonium hydrogen sulfate can be prepared from tetrabutylammonium azide by treating it with potassium hydrogen sulfate and 10% aqueous sulfuric acid in aqueous medium or from tetrabutylammonium thiocyanate by treating it with relatively concentrated sulfuric acid (70%) at 75 °C.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Related reactions
Linked notes
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