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5137-55-3

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5137-55-3 Usage

Description

Methyltrioctylammonium 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.

Reference

N. Pourreza, H. Zavvar Mousavi, Determination of cadmium by flame atomic absorption spectrometry after preconcentration on naphthalene– methyltrioctylammonium chloride adsorbent as tetraiodocadmate (II) ions, Analytica Chimica Acta, 2004, vol. 503, pp. 279-282

Chemical Properties

viscous colourless to pale orange liquid

Uses

Different sources of media describe the Uses of 5137-55-3 differently. You can refer to the following data:
1. Methyltrioctylammonium 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.
2. Mixture of C8 and C10 chains with C8 predominating. Used as a metal extraction reagent and a phase-transfer catalyst.

Definition

ChEBI: An organic chloride salt having methyltrioctylammonium as the cation.

Flammability and Explosibility

Notclassified

Safety Profile

Poison by ingestion and intraperitoneal routes. When heated to decomposition it emits very toxic fumes of NOx, NH3, and Cl-.

Purification Methods

A 30% (v/v) of Aliquat 336 solution in *benzene is washed twice with an equal volume of 1.5M HBr. [Petrow & Allen, Anal Chem 33 1303 1961.] It is purified by dissolving 50g in CHCl3 (100mL) and shaking with 20% NaOH solution (200mL) for 10minutes, and followed by 20% NaCl (200mL) for 10minutes. It is then washed with a small volume of H2O and filtered through a dry filter paper [Adam & Pribil Talanta 18 733 1971]. n-Alkylammonium chloride n=2,4,6. Recrystallise them from EtOH or an EtOH/Et2O mixture. [Hashimoto & Thomas J Am Chem Soc 107 4655 1985, Chu & Thomas J Am Chem Soc 108 6270 1986.] n-Alkyltrimethylammonium bromide n=10,12,16. Recrystallise them from an EtOH/Et2O mixture. [Hashimoto & Thomas J Am Chem Soc 107 4655 1985.]

Check Digit Verification of cas no

The CAS Registry Mumber 5137-55-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,1,3 and 7 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 5137-55:
(6*5)+(5*1)+(4*3)+(3*7)+(2*5)+(1*5)=83
83 % 10 = 3
So 5137-55-3 is a valid CAS Registry Number.
InChI:InChI=1/C25H53N/c1-4-7-10-13-16-19-22-25(26,23-20-17-14-11-8-5-2)24-21-18-15-12-9-6-3/h4-24,26H2,1-3H3/p+1

5137-55-3 Well-known Company Product Price

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  • Aldrich

  • (69485)  Methyltrioctylammoniumchloride  ≥97.0% (AT)

  • 5137-55-3

  • 69485-10G

  • 919.62CNY

  • Detail
  • Aldrich

  • (69485)  Methyltrioctylammoniumchloride  ≥97.0% (AT)

  • 5137-55-3

  • 69485-50G

  • 3,452.67CNY

  • Detail

5137-55-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name methyltrioctylammonium chloride

1.2 Other means of identification

Product number -
Other names ADOGEN 464

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Surface active agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5137-55-3 SDS

5137-55-3Synthetic route

Tri-n-octylamine
1116-76-3

Tri-n-octylamine

dimethyl sulfate
77-78-1

dimethyl sulfate

Aliquat 336
5137-55-3

Aliquat 336

Conditions
ConditionsYield
In toluene at 140℃; for 18h;99%
1-Chlorooctane
111-85-3

1-Chlorooctane

tri-n-octylmethylammonium fluoride
119409-25-5

tri-n-octylmethylammonium fluoride

A

1-Fluoro-octane
463-11-6

1-Fluoro-octane

B

Aliquat 336
5137-55-3

Aliquat 336

Conditions
ConditionsYield
at 80℃; Rate constant; Kinetics; Thermodynamic data; activation energy;
Tri-n-octylamine
1116-76-3

Tri-n-octylamine

methylene chloride
74-87-3

methylene chloride

Aliquat 336
5137-55-3

Aliquat 336

Conditions
ConditionsYield
In acetonitrile at 50℃; for 24h;
Aliquat 336
5137-55-3

Aliquat 336

fluorescein free acid
518-45-6

fluorescein free acid

C20H11O5(1-)*C25H54N(1+)

C20H11O5(1-)*C25H54N(1+)

Conditions
ConditionsYield
With IRA-400(OH) resin In methanol at 20℃;100%
Aliquat 336
5137-55-3

Aliquat 336

fluorescein free acid
518-45-6

fluorescein free acid

C20H10O5(2-)*2C25H54N(1+)

C20H10O5(2-)*2C25H54N(1+)

Conditions
ConditionsYield
With Amberlite IRA-400(OH) resin In methanol at 20℃;100%
Aliquat 336
5137-55-3

Aliquat 336

methyl tri-n-octyl ammonium hydrogen sulfate

methyl tri-n-octyl ammonium hydrogen sulfate

Conditions
ConditionsYield
With sulfuric acid In toluene at 20℃; for 24h;99%
With sulfuric acid In water
C16H23O3(1-)

C16H23O3(1-)

Aliquat 336
5137-55-3

Aliquat 336

tri-n-octylmethylammonium (2-sec-octylphenoxy) acetate

tri-n-octylmethylammonium (2-sec-octylphenoxy) acetate

Conditions
ConditionsYield
With sodium hydroxide In methanol at 60℃; for 2h; Large scale;98.1%
2-chloro-6 fluorobenzyl chloride
55117-15-2

2-chloro-6 fluorobenzyl chloride

Aliquat 336
5137-55-3

Aliquat 336

N-methyladenine
443-72-1

N-methyladenine

9-(2-chloro-6-fluorobenzyl)-6-methylaminopurine
70091-21-3

9-(2-chloro-6-fluorobenzyl)-6-methylaminopurine

Conditions
ConditionsYield
With sodium hydroxide In acetone98%
Aliquat 336
5137-55-3

Aliquat 336

Thiosalicylic acid
147-93-3

Thiosalicylic acid

tricaprylmethylammonium thiosalicylate
1027004-61-0

tricaprylmethylammonium thiosalicylate

Conditions
ConditionsYield
With sodium hydroxide at 60℃; for 4h;98%
With sodium hydroxide In water at 40℃; for 4h; Inert atmosphere;98%
3-methoxy-4-hydroxybenzoic acid
121-34-6

3-methoxy-4-hydroxybenzoic acid

Aliquat 336
5137-55-3

Aliquat 336

tricaprylmethylammonium vanillate
1228997-37-2

tricaprylmethylammonium vanillate

Conditions
ConditionsYield
With sodium hydroxide In water; acetone at 40℃; for 24h; Inert atmosphere;98%
Aliquat 336
5137-55-3

Aliquat 336

trioctylmethylammonium hexafluorophosphate

trioctylmethylammonium hexafluorophosphate

Conditions
ConditionsYield
With potassium hexafluorophosphate In water; butanone at 25℃; for 1h;98%
diethyl 3-(propan-2-yl)-1H-pyrrole-2,4-dicarboxylate
651744-38-6

diethyl 3-(propan-2-yl)-1H-pyrrole-2,4-dicarboxylate

Aliquat 336
5137-55-3

Aliquat 336

diethyl 1-amino-3-(propan-2-yl)-1H-pyrrole-2,4-dicarboxylate
651744-39-7

diethyl 1-amino-3-(propan-2-yl)-1H-pyrrole-2,4-dicarboxylate

Conditions
ConditionsYield
With ammonium hydroxide; sodium hypochlorite; ammonium chloride; sodium hydroxide In tert-butyl methyl ether; water at 20℃; for 72h;98%
Aliquat 336
5137-55-3

Aliquat 336

benzoic acid
65-85-0

benzoic acid

tricaprylmethylammonium benzoate
76312-51-1

tricaprylmethylammonium benzoate

Conditions
ConditionsYield
With sodium hydroxide at 60℃; for 4h;97%
With sodium hydroxide In ethanol; water at 60℃; for 5h; Inert atmosphere;97%
Aliquat 336
5137-55-3

Aliquat 336

hexanoic acid
142-62-1

hexanoic acid

tricaprylmethylammonium hexanoate

tricaprylmethylammonium hexanoate

Conditions
ConditionsYield
With sodium hydroxide at 60℃; for 4h;97%
Aliquat 336
5137-55-3

Aliquat 336

2-(methylthio)benzoic acid
3724-10-5

2-(methylthio)benzoic acid

tricaprylmethylammonium 2-(methylthio)benzoate
1092451-42-7

tricaprylmethylammonium 2-(methylthio)benzoate

Conditions
ConditionsYield
With sodium hydroxide In acetone at 20℃; for 48h; Inert atmosphere;96%
Aliquat 336
5137-55-3

Aliquat 336

tricaprylmethylammonium borohydride

tricaprylmethylammonium borohydride

Conditions
ConditionsYield
With sodium hydroxide; sodium tetrahydroborate In water at 20℃;95%
phosphoric acid
86119-84-8, 7664-38-2

phosphoric acid

Aliquat 336
5137-55-3

Aliquat 336

ortho-tungstic acid

ortho-tungstic acid

tris(methyltri-n-octylammonium) tetrakis(oxodiperoxotungsto)phosphate

tris(methyltri-n-octylammonium) tetrakis(oxodiperoxotungsto)phosphate

Conditions
ConditionsYield
In dihydrogen peroxide; benzene mixing (50°C, 40 min); evapn.;95%
Stage #1: ortho-tungstic acid With dihydrogen peroxide at 60℃;
Stage #2: phosphoric acid; Aliquat 336 In dichloromethane; water
(phenylthio)acetic acid
103-04-8

(phenylthio)acetic acid

Aliquat 336
5137-55-3

Aliquat 336

tricaprylmethylammonium (phenylthio)acetate
1092451-43-8

tricaprylmethylammonium (phenylthio)acetate

Conditions
ConditionsYield
With sodium hydroxide In water; acetonitrile at 60℃; for 24h; Inert atmosphere;95%
Aliquat 336
5137-55-3

Aliquat 336

methyl(tri-n-octyl)ammonium bromide
35675-80-0

methyl(tri-n-octyl)ammonium bromide

Conditions
ConditionsYield
With potassium bromide In water for 3h;95%
sodium tungstate (VI) dihydrate
10213-10-2

sodium tungstate (VI) dihydrate

diprop-2-en-1-yl pentanedioate
41226-64-6

diprop-2-en-1-yl pentanedioate

Aliquat 336
5137-55-3

Aliquat 336

Diglycidyl Glutarate
133548-06-8

Diglycidyl Glutarate

Conditions
ConditionsYield
With phosphoric acid; dihydrogen peroxide In water; toluene94%
lithium aluminium tetrahydride
16853-85-3

lithium aluminium tetrahydride

Aliquat 336
5137-55-3

Aliquat 336

C25H54N(1+)*AlH4(1-)

C25H54N(1+)*AlH4(1-)

Conditions
ConditionsYield
at 50℃; for 2.66667h; Inert atmosphere; Reflux;93.1%
4-methylthiobenzaldehyde
146857-81-0

4-methylthiobenzaldehyde

methyl 5-fluoro-2-methyl-1H-3-indenylacetate
37794-13-1

methyl 5-fluoro-2-methyl-1H-3-indenylacetate

Aliquat 336
5137-55-3

Aliquat 336

sulindac sulfide
61812-45-1

sulindac sulfide

Conditions
ConditionsYield
With hydrogenchloride In water; toluene92%
sodium salicylate
54-21-7

sodium salicylate

Aliquat 336
5137-55-3

Aliquat 336

tricaprylmethylammonium salicylate
82534-59-6

tricaprylmethylammonium salicylate

Conditions
ConditionsYield
In water; acetone at 20℃; for 24h; Inert atmosphere;91%
Aliquat 336
5137-55-3

Aliquat 336

methyltrioctylammonium hydroxide

methyltrioctylammonium hydroxide

Conditions
ConditionsYield
Stage #1: Aliquat 336 With sodium; isopropyl alcohol at 50℃; for 4h;
Stage #2: With water for 1h;
91%
With Amberlite IRA-400-OH In methanol
With sodium hydroxide In water
With sodium hydroxide In chloroform
With sodium hydroxide In chloroform; water for 1h;
2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

2,6-dimethylbenzene boronic acid
100379-00-8

2,6-dimethylbenzene boronic acid

Aliquat 336
5137-55-3

Aliquat 336

2’,2,4-trimethylbiphenyl
76708-74-2

2’,2,4-trimethylbiphenyl

Conditions
ConditionsYield
With palladium diacetate In water; toluene91%
Aliquat 336
5137-55-3

Aliquat 336

tri(octyl)-methylammonium iodide
35675-86-6

tri(octyl)-methylammonium iodide

Conditions
ConditionsYield
With potassium iodide In water for 3h;90.1%
N-cyano-N'-methyl-N

N-cyano-N'-methyl-N"-(1-chloroethyl)guanidine

Aliquat 336
5137-55-3

Aliquat 336

5-methyl-4-mercaptomethylimidazole hydrochloride
70826-45-8

5-methyl-4-mercaptomethylimidazole hydrochloride

N-cyano-N'-methyl-N''-{2-[(4-methyl-5-imidazolyl)-methylthio]-ethyl}guanidine
270574-63-5, 785731-92-2, 752934-25-1, 51481-61-9, 76181-71-0

N-cyano-N'-methyl-N''-{2-[(4-methyl-5-imidazolyl)-methylthio]-ethyl}guanidine

Conditions
ConditionsYield
With sodium hydroxide In methanol; isopropyl alcohol90%
sodium tetraphenyl borate
143-66-8

sodium tetraphenyl borate

Aliquat 336
5137-55-3

Aliquat 336

tricaprylmethylammonium tetraphenylborate

tricaprylmethylammonium tetraphenylborate

Conditions
ConditionsYield
In water; acetone at 20℃; for 12h; Inert atmosphere;90%
(RS)-2-(4-chloro-o-tolyloxy)propionic acid
93-65-2

(RS)-2-(4-chloro-o-tolyloxy)propionic acid

Aliquat 336
5137-55-3

Aliquat 336

trioctylmethylammonium (+/-)-2-(4-chloro-2-methylphenoxy)propionate
1354726-06-9

trioctylmethylammonium (+/-)-2-(4-chloro-2-methylphenoxy)propionate

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; for 2h;90%
11-bromo-undecanoic acid methyl ester
6287-90-7

11-bromo-undecanoic acid methyl ester

Aliquat 336
5137-55-3

Aliquat 336

thioacetic acid
507-09-5

thioacetic acid

methyl 11-thioacetylundecanoate

methyl 11-thioacetylundecanoate

Conditions
ConditionsYield
With caesium carbonate In dichloromethane; water89%
Aliquat 336
5137-55-3

Aliquat 336

sodium 4-methoxybenzenesulfinate
6462-50-6

sodium 4-methoxybenzenesulfinate

2-chloromethyl 3-methyl pyridine hydrochloride
4370-22-3

2-chloromethyl 3-methyl pyridine hydrochloride

4-methoxy benzenesulfonyl 2-methyl 3-methyl pyridine

4-methoxy benzenesulfonyl 2-methyl 3-methyl pyridine

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; toluene85.2%
sodium tungstate (VI) dihydrate
10213-10-2

sodium tungstate (VI) dihydrate

diallyl terephthalate
1026-92-2

diallyl terephthalate

Aliquat 336
5137-55-3

Aliquat 336

terephthalic acid diglycidyl ester
7195-44-0

terephthalic acid diglycidyl ester

Conditions
ConditionsYield
With phosphoric acid; dihydrogen peroxide In water; toluene85%

5137-55-3Relevant articles and documents

IONIC LIQUID COMPOSITION AND SOLVENT CONTAINING THE SAME

-

Paragraph 0052-0054; 0056, (2018/10/16)

PROBLEM TO BE SOLVED: To provide an ionic liquid composition satisfying high flowability and high hydrophobic property. SOLUTION: There is provided the ionic liquid composition containing at least one kind of solid organic salt having a melting point of 70°C or more and at least one kind of liquid organic salt having a melting point of 30°C or less, the solid organic salt and the liquid organic salt having a same cationic part or a same anionic part, the ionic liquid composition has a moisture content of 1 to 50 mass%, a water/n-octanol calculated distribution coefficient (LogP) of 0.5 or more and a viscosity of 3 Pa s or less at 25°C. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

Triphasic liquid systems: Generation and segregation of catalytically active Pd nanoparticles in an ammonium-based catalyst-philic phase

Perosa, Alvise,Tundo, Pietro,Selva, Maurizio,Canton, Patrizia

, p. 4480 - 4482 (2008/09/18)

A triphasic liquid system fabricated from isooctane, aqueous base, and trioctylmethylammonium chloride/decanol promoted the formation of Pd-nanoparticles in the size range of 2-4 nm which remained immobilised in the onium phase, catalysed organic reactions, and could be recycled. The Royal Society of Chemistry 2006.

Process for preparing 2-amino-1, 3-alkanediol or a derivative thereof, process for preparing optically active dihydrosphingosine derivatives and intermediates used in that process

-

, (2008/06/13)

A process for preparing an optically active dihydrosphingosine derivative, comprising reducing a (2R,3R)-2-amino-3-hydroxyalkanoic acid derivative represented by formula (III): wherein R3represents a straight-chain alkyl group having 7 to 21 carbon atoms; and R4represents an amino group protecting group,(e.g., (2R,3R)-2-benzylamino-3-hydroxyoctadecanoic acid) with sodium tetrahydroborate in the presence of an acid. The process of the invention makes it feasible to produce an optically active dihydrosphingosine at high optical purity and provides a simple process that is safe and easy to industrialize.

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