111-95-5

Basic information

• Product Name: BIS(2-METHOXYETHYL)AMINE
• Synonyms: 2-methoxy-n-(2-methoxyethyl)-ethanamin;2-methoxy-N-(2-methoxyethyl)-Ethanamine;2,2'-DIMETHOXYDIETHYLAMINE;BIS(2-METHOXYETHYL)AMINE;Bis(2-methoxyethyl)amine, 98+%;2-Methoxy-N-(2-methoxyethyl)-ethanam;NSC 78431;Bis(2-Methoxyethyl)aMine 98%
• CAS NO: 111-95-5
• Molecular Formula: C₆H₁₅NO₂
• Molecular Weight: 133.19
• EINECS: 203-923-9
• Product Categories: Amino Alcohols;Organic Building Blocks;Oxygen Compounds;Amino Alcohols;Building Blocks;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 111-95-5.mol
• Article Data: 11

Chemical Properties

• Melting Point: <-60°C
• Boiling Point: 170-172 °C(lit.)
• Flash Point: 137 °F
• Appearance: /
• Density: 0.902 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.43mmHg at 25°C
• Refractive Index: n20/D 1.419(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 8.67±0.19(Predicted)
• Water Solubility: Completely miscible in water
• BRN: 1736313
• CAS DataBase Reference: BIS(2-METHOXYETHYL)AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(2-METHOXYETHYL)AMINE(111-95-5)
• EPA Substance Registry System: BIS(2-METHOXYETHYL)AMINE(111-95-5)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2734 8/PG 2
• WGK Germany: 3
• F: 34
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 111-95-5(Hazardous Substances Data)

Usage

General Description

BIS(2-METHOXYETHYL)AMINE, also known as 2-(2-methoxyethoxy)ethylamine, is a chemical compound with the molecular formula C6H15NO2. It is a colorless liquid with a faint amine odor, commonly used as a solvent in various industrial processes, including in the production of pharmaceuticals, agrochemicals, and coatings. BIS(2-METHOXYETHYL)AMINE is also used as a corrosion inhibitor, an intermediate for chemical synthesis, and in the manufacture of textiles and dyes. It is considered to have low acute toxicity but can cause skin and eye irritation upon contact. BIS(2-METHOXYETHYL)AMINE should be handled and used with proper safety precautions to avoid adverse health effects.

InChI:InChI=1/C6H15NO2/c1-8-5-3-7-4-6-9-2/h7H,3-6H2,1-2H3

Synthetic route

N,N-bis(2-methoxyethyl)formamide (89855-74-3) → Bis-(2-methoxyethyl)amine (111-95-5)

Conditions	Yield
With RuCl2[(Ph2PCH2CH2)2NH](t-Bu-NC); potassium tert-butylate; deuterium at 120℃; under 15201 Torr; for 16h;

N,N-bis(2-methoxyethyl)tritylamine → Bis-(2-methoxyethyl)amine (111-95-5)

Conditions	Yield
Stage #1: N,N-bis(2-methoxyethyl)tritylamine With naphthalene; lithium In tetrahydrofuran at 0℃; for 2h; Stage #2: With water In tetrahydrofuran at 0 - 20℃;	90%

bis(2-methoxyethyl)(triphenylsilyl)amine → Bis-(2-methoxyethyl)amine (111-95-5)

Conditions	Yield
With naphthalene; lithium In tetrahydrofuran; methanol at 20℃; for 5h;	97%

N,N-bis(2-methoxyethyl)-4-methylbenzenesulfonamide (343581-97-5) → Bis-(2-methoxyethyl)amine (111-95-5)

Conditions	Yield
Product distribution / selectivity;	86%
Stage #1: N,N-bis(2-methoxyethyl)-4-methylbenzenesulfonamide With Na/K absorbed into silica gel In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: With water In tetrahydrofuran	85%

N,N-bis(2-methoxyethyl)pivalamide → Bis-(2-methoxyethyl)amine (111-95-5)

Conditions	Yield
With naphthalene; lithium In tetrahydrofuran at 0℃; for 1h;	45 % Chromat.

2-Bromoethyl methyl ether (6482-24-2) → Bis-(2-methoxyethyl)amine (111-95-5) + 2-methoxy-ethylamine; hydrobromide

Conditions	Yield
With ammonia In methanol at 130℃; for 2.5h; microwave irradiation;

N,N-bis(2-methoxyethyl)benzenesulfonamide → Bis-(2-methoxyethyl)amine (111-95-5)

Conditions	Yield
Product distribution / selectivity;	75%

2-chloroethyl methyl ether (627-42-9) → Bis-(2-methoxyethyl)amine (111-95-5)

Conditions	Yield
With ammonia In methanol

2-methoxy-ethanol (109-86-4) → Bis-(2-methoxyethyl)amine (111-95-5) + 2-methoxy-ethylamine and tris-<2-methoxy-ethyl>-amine

Conditions	Yield
With ammonia; nickel at 240℃;

2-chloroethyl methyl ether (627-42-9) + 2-methoxyethylamine (109-85-3) → Bis-(2-methoxyethyl)amine (111-95-5)

Upstream product

• 627-42-9 2-chloroethyl methyl ether 
• 109-85-3 2-methoxyethylamine 
• 343581-97-5 N,N-bis(2-methoxyethyl)-4-methylbenzenesulfonamide 
• 89855-74-3 N,N-bis(2-methoxyethyl)formamide 
• 6482-24-2 2-Bromoethyl methyl ether 
• 109-86-4 2-methoxy-ethanol 

Downstream Products

• 29090-94-6 N³,N³-Bis-(2-methoxy-ethyl)-2,4-dinitro-6-trifluoromethyl-benzene-1,3-diamine 
• 5815-11-2 N,N-bis(2-methoxy-ethyl)-hydroxylamine 
• 115178-64-8 Benzoic acid [bis-(2-methoxy-ethyl)-carbamoyl]-methyl ester 
• 118723-51-6 1-<<methyl>dimethylsilyl>-2-(4-methyl-3-cyclohexenyl)-2-propene 
• 138036-53-0 N,N-bis(2-methoxyethyl)-2,2,2-trifluoro-1,1-diphenylethanesulfenamide 
• 96825-95-5 3-(4-Chlorophenyl)-N,N-bis (2-methoxyethyl)pyridazino[4,3-c]isoquinolin-6-amine 
• 96825-88-6 N,N-bis(2-methoxyethyl)-3-(4-methoxyphenyl)pyridazino[4,3-c]isoquinolin-6-amine 
• 77663-81-1 3,4,5-Trimethoxy-N,N-bis-(2-methoxy-ethyl)-thiobenzamide 
• 87540-38-3 Bis-(2-methoxy-ethyl)-(3-m-tolyl-[1,2,4]triazolo[3,4-a]phthalazin-6-yl)-amine 
• 87540-39-4 Bis-(2-methoxy-ethyl)-(3-p-tolyl-[1,2,4]triazolo[3,4-a]phthalazin-6-yl)-amine 
• 87540-37-2 [3-(3-Chloro-phenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]-bis-(2-methoxy-ethyl)-amine 
• 113628-69-6 4-{6-[Bis-(2-methoxy-ethyl)-amino]-[1,2,4]triazolo[3,4-a]phthalazin-3-yl}-phenol 
• 113628-68-5 [3-(4-Fluoro-phenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]-bis-(2-methoxy-ethyl)-amine 
• 87540-36-1 [3-(4-Chloro-phenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]-bis-(2-methoxy-ethyl)-amine 

Relevant articles and documents

TRANSITION METAL ISONITRILE CATALYSTS

The present disclosure relates to new transition metal isonitrile compounds, processes for the production of the compounds and the use of the compounds as catalysts. The disclosure also relates to the use of the metal isonitrile compounds as catalysts for hydrogenation and transfer hydrogenation of compounds containing one or more carbon-oxygen, and/or carbon-nitrogen and/or carbon-carbon double bonds.

Alkali metals in silica gel (M-SG): A new reagent for desulfonation of amines

(Chemical Equation Presented) A novel method for the desulfonation of secondary amines is described. Alkali metals absorbed into nanostructured silica (M-SG) were found to be useful solid-state reagents for the desuffonation of a range of N,N-disubstituted sulfonamides. M-SG reagents are room-temperature- stable free-flowing powders that retain the chemical reactivity of the parent metal, decreasing the danger and associated cost of using reactive metals.

Desilylation procedure via a naphthalene-catalysed lithiation reaction

The reaction of silyl protected alcohols, amines and thiols with lithium powder and a catalytic amount of naphthalene, in THF, at 0°C led, after hydrolysis, to the recovery of the free alcohols, amines and thiols in very good yields. At least a phenyl group was required in the silyl protecting group for the success of the reaction. Some polyfunctionalised starting materials have successfully been deprotected. The stereochemical outcome of the deprotection of a silylated chiral secondary alcohol has also been studied and no racemization was observed. The process has shown to be a good alternative to the acid-catalysed desilylation procedures, the latter being not useful for the deprotection of some silylated tertiary alcohols.