Trioctylmethylammonium chloride
Basic information
- CAS
5137-55-3- Standard SMILES
CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC.[Cl-]- InChIKey
XKBGEWXEAPTVCK-UHFFFAOYSA-M- Molecular formula
- C25H54N.Cl
- Average molar mass
- 404.2 g/mol
- Monoisotopic mass
- 403.3944784
Overview
Methyltrioctylammonium chloride is an organic chloride salt having methyltrioctylammonium as the cation. It has a role as a phase-transfer catalyst. It is a quaternary ammonium salt and an organic chloride salt. It contains a methyltrioctylammonium.
Names & identifiers
- Preferred name
- Trioctylmethylammonium chloride
- IUPAC
- methyl(trioctyl)azanium chloride
- English name
- Methyl trioctyl ammonium chloride
- Molecular formula
- C25H54N.Cl
- Molecular weight
- 404.16
Names & synonyms
5137-55-3Methyltrioctylammonium chlorideTrioctylmethylammonium chlorideTOMACCapriquatMethyltricaprylylammonium chlorideTricaprylylmethylammonium chlorideTricaprylmethylammonium chlorideTrioctylmonomethylammonium chlorideN-Methyl-N,N-dioctyl-1-octanaminium chlorideDTXSID1044487AMMONIUM, METHYLTRIOCTYL-, CHLORIDE
Show more names
ALIQUAT 336aliquatADOGEN 464METHYLTRI-N-OCTYLAMMONIUM CHLORIDE
Tricaprylyl methyl ammonium chlorideAliquat 12807Q8S2MJ6ANSC-61369TOMAC 75DTXCID9024487CHEBI:75286TOMAC salt
Database identifiers
- CAS
5137-55-3- PubChem CID
- 21218
- DTXSID
DTXSID1044487- ChEMBL
CHEMBL3188519- ChEBI
CHEBI:75286- UNII
- 07Q8S2MJ6A
- EC Number
- 225-896-2
Properties
Computed structural properties
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 21
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 220
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Quaternary Amines
Density0.884 @25 °C
Boiling Point225 °C @760 [mm Hg]
Melting Point-20 °C
Physical DescriptionYellow viscous liquid; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- -20 °C · -20°C
- Boiling point
- 240 °C · 240°C
- Density
- 0.884 g/mL · 0.884 g/mL at 25 °C(lit.)
- vapor pressure
- 0 Pa · 0Pa at 25℃
- refractive index
- 20 · n20/D 1.4665(lit.)
- Flash point
- 230 °F · >230 °F
- storage temp.
- 2 · under inert gas (nitrogen or Argon) at 2-8°C
- solubility
- soluble in Chloroform, Hexanes
- form
- Viscous Liquid
- color
- Colourless to pale orange
- Odor
- Ammonical
- Viscosity
- 230.945 mm2/s · 230.945mm2/s
- Water Solubility
- Partially insoluble
- Sensitive
- Hygroscopic
- BRN
- 4039255 · 4039255
- Stability
- Stable. Incompatible wth strong oxidizing agents. Hygroscopic.
- InChI
- 1S/C25H54N.ClH/c1-5-8-11-14-17-20-23-26(4,24-21-18-15-12-9-6-2)25-22-19-16-13-10-7-3;/h5-25H2,1-4H3;1H/q+1;/p-1
- InChIKey
- XKBGEWXEAPTVCK-UHFFFAOYSA-M
- SMILES
- [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC
- LogP
- 4.5 at · 4.5 at 25℃
- CAS DataBase Reference
- 5137 · 5137-55-3(CAS DataBase Reference)
- FDA UNII
- 7 Q8S2MJ6A · 07Q8S2MJ6A
- EPA Substance Registry System
- Methyltrioctylammonium chloride (5137-55-3)
- UNSPSC Code
- 12352116 · 12352116
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05,GHS06,GHS08,GHS09
- Signal word
- Danger
- Hazard statements
- 301 · H301-H314-H360FD-H373-H410
- Precautionary statements
- 202 · P202-P273-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- Hazard Codes
- Xn,N,C
- Risk Statements
- 22 · 22-38-41-50/53-36/37/38-20/21/22-34
- Safety Statements
- 26 · 26-39-60-61-36-45-36/37/39
- RIDADR
- 2810 · UN 2810 6.1/PG 3
- WGK Germany
- 3 · 3
- RTECS
- 2997500 · UZ2997500
- F
- 3 · 3-10
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- III
- HS Code
- 29239000 · 29239000
- Storage Class
- 6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard Classifications
- 3 OralAquatic · Acute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Repr. 1BSkin Corr. 1ASTOT RE 2
- REACH Registrations
- Active
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (79.6%): Toxic if swallowed [Danger Acute toxicity, oral]
P260, P264, P264+P265, P270, P273, P280, P301+P316, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P321, P330, P332+P317, P337+P317, P362+P364, P363, P391, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 191 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 1-Octanaminium, N-methyl-N,N-dioctyl-, chloride
REACH registered substance: Methyltrioctylammonium chloride (EC: 225-896-2)
Methyltrioctylammonium chloride: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
A severe skin irritant; Causes muscle weakness in intraperitoneal lethal-dose studies of guinea pigs, mice, and rats; Causes diarrhea and respiratory depression in oral lethal-dose studies of rats; [RTECS] An irritant that may cause serious eye injury; Harmful by ingestion; [Alfa Aesar MSDS]
Hazard Classes and CategoriesAcute Tox. 3 (79.6%)
Safety & protection
Protective Action Criteria (PAC)
0.67 [mg/m3]
7.4 [mg/m3]
44 [mg/m3]
Safety data
- F
- 3-10
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- UZ2997500
- ridadr
- UN 2810 6.1/PG 3
- hs_code
- 29239000
- risk_code
- 22-38-41-50/53-36/37/38-20/21/22-34
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS06,GHS08,GHS09
- hazard_code
- Xn,N,C
- safety_code
- 26-39-60-61-36-45-36/37/39
- hazard_class
- 6.1
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- packing_group
- III
- Hazard statements
- H301-H314-H360FD-H373-H410
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Repr. 1BSkin Corr. 1ASTOT RE 2
- Precautionary statements
- P202-P273-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
Chemistry & industry
Uses & manufacturing
UsesPermitted for use as an inert ingredient in non-food pesticide products; [EPA] Used in high performance liquid chromatography for the separation of tRNA. [ChemIDplus]
General Manufacturing Information1-Octanaminium, N-methyl-N,N-dioctyl-, chloride (1:1): ACTIVE
Applications
DescriptionMethyltrioctylammonium chloride is a water insoluble quaternary ammonium salt, which is widely used as a counter ion in solvent extraction of anionic metal complexes. It is widely used as a phase transfer catalyst for the catalytic oxidation of cyclohexene to 1,6-hexanedioic acid. In comparison to traditional method of oxidizing cyclohexanol or cyclohexanone with nitric acid or potassium permanganate, the usage of methyltrioctylammonium chloride is a more environmentally friendly reaction.
UsesMethyltrioctylammonium chloride can be used:As a catalyst in the synthesis of acridine dione derivatives from aromatic aldehyde, dimedone and amines under ultrasonic irradiations.As a catalyst in the synthesis of extended π-systems using aromatic aldehydes and methyldiazines.As a component of a catalytic system used in the Suzuki-Miyaura cross-coupling reaction of a variety of aryl and heteroaryl chlorides in H2O.
UsesMixture of C8 and C10 chains with C8 predominating. Used as a metal extraction reagent and a phase-transfer catalyst.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: An organic chloride salt having methyltrioctylammonium as the cation.
Related reactions
405 records
Compound notes
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