5332-73-0

Basic information

• Product Name: 3-Methoxypropylamine
• Synonyms: 3-METHOXYPROPYLAMINE FOR SYNTHESIS;3-MethoxypropylaMine, 99+%, 99+%;.gamma.-Methoxypropaneamine;1-Propanamine,3-methoxy-;3-methoxy-1-propanamin;3-Methoxy-1-propylamine;3-Methoxy-n-propylamine;3-methoxy-propylamin
• CAS NO: 5332-73-0
• Molecular Formula: C₄H₁₁NO
• Molecular Weight: 89.14
• EINECS: 226-241-3
• Product Categories: Oxygen Compounds;Amino Alcohols;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 5332-73-0.mol
• Article Data: 13

Chemical Properties

• Melting Point: -65 °C
• Boiling Point: 117-118 °C733 mm Hg(lit.)
• Flash Point: 73 °F
• Appearance: Clear colorless to faintly colored/Liquid
• Density: 0.874 g/mL at 25 °C(lit.)
• Vapor Density: 3.07 (vs air)
• Vapor Pressure: 20 mm Hg ( 30 °C)
• Refractive Index: n20/D 1.417(lit.)
• Storage Temp.: Flammables area
• PKA: 9.73±0.10(Predicted)
• Explosive Limit: 2.3-12.3%(V)
• Water Solubility: miscible
• BRN: 878144
• CAS DataBase Reference: 3-Methoxypropylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methoxypropylamine(5332-73-0)
• EPA Substance Registry System: 3-Methoxypropylamine(5332-73-0)

Safety Data

• Hazard Codes: C
• Statements: 10-34-35
• Safety Statements: 26-36/37/39-45-16
• RIDADR: UN 2734 8/PG 2
• WGK Germany: 1
• RTECS: UI3335000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 5332-73-0(Hazardous Substances Data)

Usage

Description

3-Methoxypropylamine (MOPA) is a liquid C3-Aminoether, characterized by its clear, colorless to faintly colored appearance and an ammonia-like odor. It possesses properties typical of primary amines and is miscible with various solvents such as water, ethanol, toluene, acetone, and hexane. MOPA is primarily used as a corrosion inhibitor and an organic intermediate in the production of amine soaps.

Uses

Used in Chemical Industry:
3-Methoxypropylamine is used as an organic intermediate for the synthesis of various chemicals and compounds.
Used in Corrosion Inhibition:
3-Methoxypropylamine is used as a corrosion inhibitor to protect metals from degradation and wear in industrial applications.
Used in Coatings and Wax Formulations:
3-Methoxypropylamine is used as an emulsifier in anionic coatings and wax formulations, enhancing the stability and performance of these products.
Used in Dispersions and Emulsions:
3-Methoxypropylamine is used in making amine soaps that can be used in dispersions and emulsions of natural and synthetic waxes. This application is particularly relevant in industries such as flowing, textiles, and water-based paints.
Used in Textile Industry:
In the textile industry, 3-Methoxypropylamine is used as a component in the formulation of treatments and finishes that improve the quality and durability of fabrics.
Used in Water-Based Paints:
3-Methoxypropylamine is used in the production of water-based paints to improve their emulsifying properties and overall performance.

Hazard

Flammable, moderate fire risk. Toxic by ingestion and inhalation.

Flammability and Explosibility

Flammable

Safety Profile

Poison by intravenous route. Irritating to skin, eyes, and mucous membranes. Dangerous fire hazard when exposed to heat or flame; can react with oxidizing materials. To fight fire, use CO2, dry chemical. When heated to decomposition it emits toxic fumes of NOx. See also AMINES.

InChI:InChI=1/C4H11NO/c1-6-4-2-3-5/h2-5H2,1H3/p+1

Synthetic route

C6H5CHNCH2CH2CH2OCH3 (105427-51-8) → 3-methoxypropylamine (5332-73-0)

Conditions	Yield
Stage #1: C6H5CHNCH2CH2CH2OCH3 With hydrogenchloride In cyclohexane at -10 - 0℃; for 14h; Stage #2: With sodium carbonate In dichloromethane at -10 - 0℃; for 12h;	99.42%

3-Methoxypropionitrile (110-67-8) → 3-methoxypropylamine (5332-73-0)

Conditions	Yield
With hydrogen In methanol at 105 - 110℃; under 15001.5 - 22502.3 Torr; for 0.5h; Temperature; Pressure; Solvent; Autoclave;	97.2%
With hydrogen at 60 - 98℃; under 1500.15 - 22502.3 Torr; for 6h; Temperature;	95%
With hydrogenchloride; platinum(IV) oxide; hydrogen In ethanol under 2280 Torr; for 4h;	30%
With ammonia; hydrogen; Rh catalyst under 51485.6 Torr;

3-Methoxypropionitrile (110-67-8) → bis-(3-methoxy-propyl)-amine (14676-58-5) + 3-methoxypropylamine (5332-73-0)

Conditions	Yield
With ammonia; nickel at 90℃; Hydrogenation.unter Druck;
With nickel at 110℃; Hydrogenation.unter Druck;

(3-Methoxy-propyl)-[2-methyl-prop-(Z)-ylidene]-amine (22483-13-2) → 3-methoxypropylamine (5332-73-0)

Conditions	Yield
In water at 35℃; Equilibrium constant;

2-<(3-methoxy)propyl>-isoindole-1,3(2H)-dione (41081-98-5) → 3-methoxypropylamine (5332-73-0)

Conditions	Yield
With hydrazine

dimethyl sulfate (77-78-1) + propan-1-ol-3-amine (156-87-6) → 3-(Dimethylamino)-1-propyl Methyl Ether (20650-07-1) + N-[3-(methoxy)propyl]-N-methylamine (55612-03-8) + 3-methoxypropylamine (5332-73-0)

Conditions	Yield
With calcium hydride 1.) THF, room temp., 1 h; 2.) room temp., 1 h; Yield given. Multistep reaction;
With sodium hydride 1.) THF, room temp., 1 h; 2.) room temp., 1 h; Yield given. Multistep reaction;

di-tert-butyl dicarbonate (24424-99-5) + 3-methoxypropylamine (5332-73-0) → tert-butyl (3-methoxypropyl)carbamate (911300-60-2)

Conditions	Yield
In chloroform for 16h; Heating / reflux;	100%

2-hydroxy-3-(1-methyl-1-phenylethyl)benzaldehyde (165450-61-3) + 3-methoxypropylamine (5332-73-0) → C20H25NO2 (1096704-38-9)

Conditions	Yield
In ethanol at 20℃; for 6h;	100%

thiophene-2-carbaldehyde (98-03-3) + 3-methoxypropylamine (5332-73-0) → 3-methoxy-N-(thiophen-2-ylmethylene)propanamine (1227253-60-2)

Conditions	Yield
at 60℃; for 6h; Inert atmosphere;	100%

6-chloro-3H-purine (87-42-3) + 3-methoxypropylamine (5332-73-0) → (3-methoxypropyl)(3H-purin-6-yl)amine

Conditions	Yield
In butan-1-ol at 100℃; for 16h;	100%

(*S)-3-(3-((7'-chloro-1',1'-dioxidospiro[cyclopropane-1,4'-pyrido[2,3-b][1,4,5]oxathiazepin]-2'(3'H)-yl)methyl)-4-methylphenyl)-3-(8-methyl-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl)propanoic acid + 3-methoxypropylamine (5332-73-0) → ethyl (*S)-3-(3-((7'-((3-methoxypropyl)amino)-1‘,1‘-dioxidospiro[cyclopropane-1,4’-pyrido[2,3-b] [1 ,4,5]oxathiazepin]-2’(3’H)-yl)methyl)-4-methylphenyl)-3- (8-methyl-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a] pyridine-7-yl)propanoate

Conditions	Yield
In dimethyl sulfoxide at 110℃; for 1h; Microwave irradiation;	100%

4-fluoro-N-methyl-3-nitrobenzamide (475216-25-2) + 3-methoxypropylamine (5332-73-0) → 4-(3-methoxypropylamino)-3-nitrophenyl-N-methylbenzamide (658700-24-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	99%

(1R,2S)-2-{[(3aR,4R,9bR)-4-phenyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexylamine dihydrochloride + 3-methoxypropylamine (5332-73-0) → N-(3-methoxypropyl)-N'-((1R,2S)-2-{[(3aR,4R,9bR)-4-phenyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexyl)urea

Conditions	Yield
Stage #1: (1R,2S)-2-{[(3aR,4R,9bR)-4-phenyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexylamine dihydrochloride; 1,1'-carbonyldiimidazole With triethylamine In DMF (N,N-dimethyl-formamide) at 0℃; for 1h; Stage #2: 3-methoxypropylamine With triethylamine In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 14h;	99%

2,4-bis(benzyloxy)-5-bromobenzoic acid (912545-10-9) + 3-methoxypropylamine (5332-73-0) → 2,4-bis-benzyloxy-5-bromo-N-(3-methoxypropyl)benzamide (1143623-80-6)

Conditions	Yield
Stage #1: 2,4-bis(benzyloxy)-5-bromobenzoic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: 3-methoxypropylamine In N,N-dimethyl-formamide at 20℃; Product distribution / selectivity;	99%

pyridine-2-carbaldehyde (1121-60-4) + 3-methoxypropylamine (5332-73-0) → 3-methoxy-N-((pyridin-2-yl)methylene)propan-1-amine (1603164-14-2)

Conditions	Yield
With sodium sulfate In tetrahydrofuran at 25℃; for 72h; Inert atmosphere; Sealed tube;	99%
In dichloromethane at 20℃; for 24h;	78%
In methanol for 12h; Reflux;

7-(2,2-difluoroethoxy)-3-oxo-2,3-dihydro-1H-indene-4-carbonitrile + 3-methoxypropylamine (5332-73-0) → 7-(2,2-difluoroethoxy)-3-((3-methoxypropyl)imino)-2,3-dihydro-1H-indene-4-carbonitrile

Conditions	Yield
With trifluoroacetic acid In benzene for 6h; Reflux; Dean-Stark;	99%

methyl 2-((3,4-dichlorophenyl)amino)pyrimidine-4-carboxylate + 3-methoxypropylamine (5332-73-0) → N-(3-methoxypropyl) 2-((3,4-dichlorophenyl)amino)pyrimidine-4-carboxamide

Conditions	Yield
With ammonium nitrate at 20℃; for 20h;	99%

acetylacetone (123-54-6) + 3-methoxypropylamine (5332-73-0) → (CH3OC3H6)NHC(CH3)CHC(CH3)O

Conditions	Yield
at 130℃; for 0.0833333h; microwave irradiation;	98%
In ethanol for 24h; Heating;	98%

acetylacetone (123-54-6) + 3-methoxypropylamine (5332-73-0) → 4-((3-methoxypropyl)amino)pent-3-en-2-one (124747-45-1)

Conditions	Yield
at 20 - 130℃; for 0.0833333h; Microwave irradiation;	98%
at 20 - 130℃; Inert atmosphere; Microwave irradiation;	98%
In diethyl ether for 1h; Inert atmosphere; Schlenk technique; Reflux;	97%
With toluene-4-sulfonic acid In ethanol Reflux;
In diethyl ether

4-Nitrobenzenesulfonyl chloride (98-74-8) + 3-methoxypropylamine (5332-73-0) → N-(3-methoxypropyl)-4-nitro-benzenesulfonamide (349397-17-7)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 1h;	97.8%
With potassium carbonate In acetonitrile at 30℃; for 4h;

carbon monoxide (201230-82-2) + 3-methoxypropylamine (5332-73-0) → N,N'-bis(3-methoxypropyl)urea (82138-38-3)

Conditions	Yield
Stage #1: carbon monoxide; 3-methoxypropylamine With sulfur at 80℃; under 760.051 Torr; for 4h; Stage #2: With oxygen at 20℃; under 760.051 Torr; for 1h; Further stages.;	97%
With sulfur at 120℃;

tert-butyl (3R)-6-cyclohexyl-3-[3-({[(4-methylphenyl)sulfonyl]oxy}methyl)-1,2,4-oxadiazol-5-yl]hexanoate (348623-96-1) + 3-methoxypropylamine (5332-73-0) → tert-butyl (3R)-6-cyclohexyl-3-{3-[(methylamino)methyl]-1,2,4-oxadiazol-5-yl}hexanoate (438630-56-9) + tert-butyl (3R)-6-cyclohexyl-3-(3-{[(3-methoxypropyl)amino]methyl}-1,2,4-oxadiazol-5-yl)hexanoate

Conditions	Yield
	A n/a B 97%

C19H16FN3O4 (1373257-36-3) + 3-methoxypropylamine (5332-73-0) → C23H26N4O5 (1373257-44-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	97%

aniline (62-53-3) + 3-methoxypropylamine (5332-73-0) → N-(3-methoxypropyl)cyclohexanamine

Conditions	Yield
With hydrogen In neat (no solvent) at 50℃; under 760.051 Torr; for 38h;	97%

4-chloro-7-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidine (169516-55-6) + 3-methoxypropylamine (5332-73-0) → 4-(3-methoxypropylamino)-9-(2'-deoxy-2'-β-fluoro-β-D-ribofuranosyl)pyrrole[2,3-d]pyrimidine

Conditions	Yield
Stage #1: 4-chloro-7-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidine; 3-methoxypropylamine In tetrahydrofuran at 90℃; for 12h; Sealed tube; Stage #2: With ammonia In methanol	96.59%

2-amino-3-hydroxy-propionaldehyde (21228-53-5) + 3-methoxypropylamine (5332-73-0) → 3-methoxypropylformamide (71172-42-4)

Conditions	Yield
In carbon monoxide	96%

1-tert-butyl 3-methyl (3R,5S)-5-{[(2-tert-butyl-4-chloropyrimidin-5-yl)carbonyl](2-methylpropyl)amino}piperidine-1,3-dicarboxylate (1145745-34-1) + 3-methoxypropylamine (5332-73-0) → 1-tert-butyl 3-methyl (3R,5S)-5-[({2-tert-butyl-4-[(3-methoxypropyl)amino]pyrimidin-5-yl}carbonyl)(2-methylpropyl)amino]piperidine-1,3-dicarboxylate (1145745-37-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃; for 1.5h;	96%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃; for 1.5h;

2-chloro-3-nitrobenzoic acid methyl ester (53553-14-3) + 3-methoxypropylamine (5332-73-0) → methyl 2-(3-methoxypropylamino)-3-nitrobenzoate (958032-64-9)

Conditions	Yield
With triethylamine In tetrahydrofuran for 12h; Reflux;	96%

N4-p-bromobenzoyl-2',3'-O-isopropylidene-O2,5'-cyclocytidine (1386977-60-1) + 3-methoxypropylamine (5332-73-0) → N4-p-bromobenzoyl-N2-(3-methoxypropyl)amino-N1-(2',3'-O-isopropylidene-β-D-ribofuranosyl)-2(1H)-pyrimidinamine hydrochloride (1386977-61-2)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride In tetrahydrofuran at 0℃; for 0.75h;	96%

3,5-di-tert-butyl-2-hydroxybenzaldehyde (37942-07-7) + 3-methoxypropylamine (5332-73-0) → C19H31NO2

Conditions	Yield
In methanol at 20℃; Inert atmosphere; Schlenk technique;	96%

3-methoxy-2-hydroxybenzaldehyde (148-53-8) + 3-methoxypropylamine (5332-73-0) → C12H17NO3

Conditions	Yield
In methanol for 4h; Reflux;	96%

4-chloro-6,7-dihydro-5H-pyrimido<5,4-d><1>benzazepine (105895-97-4) + 3-methoxypropylamine (5332-73-0) → (6,7-Dihydro-5H-benzo[b]pyrimido[4,5-d]azepin-4-yl)-(3-methoxy-propyl)-amine

Conditions	Yield
at 65 - 70℃; for 2h;	95%

3,5-di-tert-butyl-2-hydroxybenzaldehyde (37942-07-7) + 3-methoxypropylamine (5332-73-0) → (E)-2,4-di-tert-butyl-6-(((3-methoxypropyl)imino)methyl)phenol

Conditions	Yield
In methanol for 18h; Inert atmosphere; Schlenk technique; Reflux;	95%

1-[4-(i-propyl)phenyl]-pentane-1,4-dione (1033280-93-1) + 3-methoxypropylamine (5332-73-0) → 2-(4-isopropylphenyl)-1-(3-methoxypropyl)-5-methyl-1H-pyrrole

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 160℃; under 7757.43 Torr; for 0.5h; Sealed tube; Microwave irradiation;	95%

Upstream product

• 105427-51-8 C₆H₅CHNCH₂CH₂CH₂OCH₃ 
• 110-67-8 3-Methoxypropionitrile 
• 7664-41-7 ammonia 
• 77-78-1 dimethyl sulfate 
• 156-87-6 propan-1-ol-3-amine 
• 41081-98-5 2-<(3-methoxy)propyl>-isoindole-1,3(2H)-dione 
• 22483-13-2 (3-Methoxy-propyl)-[2-methyl-prop-(Z)-ylidene]-amine 

Downstream Products

• 120208-62-0 (3-methoxy-propyl)-(4-nitro-benzyl)-amine; hydrochloride 
• 1709-03-1 N-(3-methoxypropyl)-chloroacetamide 
• 20926-49-2 2-(3-Methoxypropylamino)-5-methyl-5-nitro-1,3,2-dioxaphosphorinan-2-oxid 
• 14121-47-2 2-(3-methoxy-propyl)-thioxantheno[2,1,9-def]isoquinoline-1,3-dione 
• 17702-11-3 3-methoxypropyl isothiocyanate 
• 56224-20-5 (5-Chloro-2,4-dinitro-phenyl)-(3-methoxy-propyl)-amine 
• 56224-50-1 N,N'-Bis-(3-methoxy-propyl)-4,6-dinitro-benzene-1,3-diamine 
• 35812-32-9 (3-Methoxy-propyl)-phosphoramidic acid diisopropyl ester 
• 16191-75-6 N-<2-(4-Methyl-phenylsulfonyl)-aethyl>-3-methoxy-propylamin 
• 40093-11-6 C₁₃H₁₈ClN₃O₂ 
• 92723-19-8 N-(3-Methoxy-propyl)-N-(4-methylsulfonyl-benzyl)-amin 
• 63448-58-8 (3,4-Dimethyl-2,6-dinitro-phenyl)-(3-methoxy-propyl)-amine 
• 40487-48-7 (4-Chloro-3-methyl-2,6-dinitro-phenyl)-(3-methoxy-propyl)-amine 
• 18030-16-5 2-[(2-Acetylamino-3,5-dibromo-benzyl)-methyl-amino]-N-(3-methoxy-propyl)-acetamide 

Relevant articles and documents

Preparation method of 3-methoxypropylamine

The invention discloses a preparation method of 3-methoxylpropylamine. The method comprises the following steps: carrying out addition on methanol and acrylonitrile to prepare a 3-methoxylpropionitrile crude product, and then carrying out catalytic hydrogenation on the crude product by using a Raney catalyst to prepare the 3-methoxylpropylamine. In the addition reaction, through air protection and gradient temperature reaction control, the acrylonitrile conversion rate of the addition reaction can be increased, generation of hydrogenation reaction by-products is reduced, the acrylonitrile conversion rate is larger than 99.6%, the yeild of the 3-methoxylpropylamine is larger than 99.1% and residual quantity of acrylonitrile in the crude product is smaller than 0.3%; and the hydrogenation reaction raw materials do not need to be refined, an alkaline auxiliary agent does not need to be additionally added, the average yield of MOPA can reach 96.5%, and the catalyst can be recycled for more than 30 batches.

Method for preparing amino ether compounds

The invention belongs to the technical field of organic synthesis and relates to a method for preparing amino ether compounds. The method comprises the following steps: by taking amino alcohol as a raw material, protecting amino in the amino alcohol so as to obtain Schiff base; carrying out an etherification reaction on the hydroxyl group in the Schiff base; and finally, performing amino deprotection, thereby obtaining corresponding amino ethers. The method disclosed by the invention has high regio-selectivity, the substrates of higher than 99.9% are subjected to etherification reaction, the reaction conversion ratio of each step is higher than 99.8%, and the total yield is higher than 95%; when amino alcohol is chiral, the amino ethers with retention of configuration can be obtained; and moreover, each step of the method is a conventional operation, the process cost is low, and three wastes are few, the energy consumption is low, an environment-friendly effect is achieved, and large-scale industrial production is easily realized.

2-aminopyridine derivatives and combinatorial libraries thereof

The present invention relates to novel 2-aminopyridine derivative compounds of the following formula: wherein R1to R5have the meanings provided herein. The invention further relates to combinatorial libraries containing two or more such compounds, as well as methods of preparing 2-aminopyridine derivative compounds.