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

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

Uses

Used in Pharmaceutical Industry:
BIS(2-METHOXYETHYL)AMINE is used as a solvent for the production of pharmaceuticals, aiding in the manufacturing process by facilitating the dissolution of various compounds.
Used in Agrochemical Industry:
BIS(2-METHOXYETHYL)AMINE is used as a solvent in the production of agrochemicals, enabling the formulation of effective agricultural products.
Used in Coatings Industry:
BIS(2-METHOXYETHYL)AMINE is used as a solvent in the manufacturing of coatings, contributing to the production of high-quality paint and varnish products.
Used as a Corrosion Inhibitor:
BIS(2-METHOXYETHYL)AMINE is used to prevent corrosion in various industrial applications, protecting materials from damage and extending their lifespan.
Used as an Intermediate for Chemical Synthesis:
BIS(2-METHOXYETHYL)AMINE serves as an intermediate in the synthesis of other chemical compounds, playing a crucial role in the production of various products.
Used in Textile and Dye Industry:
BIS(2-METHOXYETHYL)AMINE is used in the manufacture of textiles and dyes, contributing to the production of vibrant and durable fabrics.
It is important to handle and use BIS(2-METHOXYETHYL)AMINE with proper safety precautions due to its potential to cause skin and eye irritation upon contact. Despite its low acute toxicity, it is essential to minimize exposure and ensure the well-being of individuals working with this chemical compound.

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

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 
• 53516-49-7 Cyclohexen-1-yl-di-(2-methoxyethyl)amin 
• 35232-90-7 N¹-Ethyl-N³,N³-bis-(2-methoxy-ethyl)-4-nitro-6-trifluoromethyl-benzene-1,3-diamine 
• 69540-85-8 3-Bis(2-methoxyethyl)amino-3-oxopropanoic acid ethyl ester 
• 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 

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.

METHOD FOR DEPROTECTING ARYL OR ALKYL SULFONAMIDES OF PRIMARY OR SECONDARY AMINES

The invention relates to a method for removing an alkyl sulfonyl or aryl sulfonyl protecting group from a primary or secondary amine by contacting an alkyl sulfonamide or an aryl sulfonamide with a Stage 0 or Stage I alkali metal-silica gel material in the presence of a solid proton source under conditions sufficient to form the corresponding amine. The invention also relates to a method for removing an alkyl sulfonyl or aryl sulfonyl protecting group from a primary or secondary amine by a) reacting an alkyl sulfonamide or an aryl sulfonamide with a Stage 0 or Stage I alkali metal-silica gel material, and b) subsequently reacting the reaction product from step a) with an electrophile or a proton source. Preferred Stage 0 or Stage I alkali metal-silica gel materials include Na, K2Na, and Na2K.

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.

Deacylation of esters, thioesters and amides by a naphthalene-catalysed lithiation

The reaction of different esters, thioesters and amides derived from pivalic, benzoic and 4-tert-butylbenzoic acids with an excess of lithium and a catalytic amount of naphthalene (8 mol%) led, after methanolysis, to the corresponding alcohols, thiols and amines, respectively, through a reductive non-hydrolytic procedure. This methodology represents a reasonable alternative to other non-reductive protocols. Georg Thieme Verlag Stuttgart.

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.

Amine compounds, resist compositions and patterning process

Amine compounds having a cyano group are useful in resist compositions for preventing a resist film from thinning and also for enhancing the resolution and focus margin of resist.

Detritylation of N-tritylamines via a naphthalene-catalyzed lithiation process

The reaction of aliphatic and aromatic secondary and tertiary N-tritylamines 1 with lithium powder and a catalytic amount of naphthalene led to reductive detritylation, affording the corresponding amines 2 in good to excellent yields. The trityl group could selectively be removed in the presence of an allyl or a benzyl group. The detritylation process could successfully be extended to several hydroxy, alkoxy and amino functionalized N-tritylamines. The chemoselectivity between the trityl-nitrogen and the trityl-oxygen bond cleavages was also studied. This methodology represents an efficient deprotection of N-tritylamines under nonacidic reaction conditions.

Microwave-assisted synthesis of primary amine HX salts from halides and 7 M ammonia in methanol

The atom economical synthesis of hydrogen halide salts of primary amines, directly from the corresponding halides, avoids the production of significant amounts of secondary amine side products, and requires only evaporation of the solvent to access the products in yields generally greater than 90%. The procedure uses microwave irradiation in 7 M ammonia in methanol (Aldrich) at 130°C from 0.5 to 2.5h and works on a variety of alkyl halides, as well as mesylates and tosylates. Benzylamines are obtained from benzyl halides without significant amounts of the secondary amine side products that result without microwave heating. Direct isolation of even highly volatile primary amines as their hydrogen halide salts makes the method ideal for use in parallel synthesis.

METHOD FOR TREATING CHRONIC PAIN USING MEK INHIBITORS

The invention features a method for treating chronic pain using a compound selected from formulae (I), (II)A, (I)B and (I)C.

Benzenesulfonamide derivatives and their use as MEK inhibitors

Benzenesulfonamides of formula (I), in which W is OR1, NR2OR1, NRARB, NR2NRARB, or NR2(CH2)2-4NRARBand the other variables as defined in the claims, are inhibitors of MEK and are effective in the treatment of proliferative diseases, cancer, stroke, heart failure, xenograft rejection, arthritis, cystic fibrosis, hepatomegaly, cardiomegaly, Alzheimer's disease, complications of diabetes, septic shock, and viral infection.