4747-28-8

Basic information

• Product Name: O,N-Diethylhydroxylamine
• Synonyms: O,N-Diethylhydroxylamine;EthanaMine, N-ethoxy-
• CAS NO: 4747-28-8
• Molecular Formula: C₄H₁₁NO
• Molecular Weight: 89.14
• Mol File: 4747-28-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 69.9°C at 760 mmHg
• Flash Point: 10.4°C
• Appearance: /
• Density: 0.812g/cm³
• Vapor Pressure: 132mmHg at 25°C
• Refractive Index: 1.388
• PKA: 5.16±0.70(Predicted)
• CAS DataBase Reference: O,N-Diethylhydroxylamine(CAS DataBase Reference)
• NIST Chemistry Reference: O,N-Diethylhydroxylamine(4747-28-8)
• EPA Substance Registry System: O,N-Diethylhydroxylamine(4747-28-8)

Safety Data

• Hazardous Substances Data: 4747-28-8(Hazardous Substances Data)

Usage

General Description

O,N-Diethylhydroxylamine is a chemical compound that is primarily used as a reducing agent and an antioxidant in several industrial applications. It is an aliphatic amine that typically exists as a colourless liquid, albeit with a somewhat fishy odor. The compound is often used in the manufacturing of pharmaceuticals, agricultural chemicals, rubber, and certain polymers. It's also widely used for photographic processing. Its chemical structure is characterized by the presence of an amine group (-NH2) and two ethyl groups (-C2H5) attached to a single oxygen atom. It is flammable and can react dangerously with strong oxidizing agents. Therefore, handling, storage, and disposal should be managed with caution.

InChI:InChI=1/C4H11NO/c1-3-5-6-4-2/h5H,3-4H2,1-2H3

Synthetic route

ethanol (64-17-5) + ethoxy-ethyl-carbamic acid ethyl ester (67549-00-2) → N,O-diethylhydroxylamine (4747-28-8)

Conditions	Yield
With potassium hydroxide

N,O-diethyl-N-thiocyanato-hydroxylamine (857812-32-9) → N,O-diethylhydroxylamine (4747-28-8)

Conditions	Yield
With hydrogenchloride

ethoxy-ethyl-carbamic acid ethyl ester (67549-00-2) → N,O-diethylhydroxylamine (4747-28-8)

Conditions	Yield
With hydrogenchloride
With phosphorus pentachloride; water bei aufeinanderfolgender Behandlung;
With potassium hydroxide at 100℃;

ethyl bromide (74-96-4) + O-ethyl hydroxylamine (624-86-2) → N,O-diethylhydroxylamine (4747-28-8)

Conditions	Yield
man zersetzt die gebildeten Salze durch KOH,stellt aus den freien Basen das saure Oxalat des O,N-Diaethyl-hydroxylamins her und zerlegt es durch Destillation mit KOH;

C5H11NO3 → N,O-diethylhydroxylamine (4747-28-8)

Conditions	Yield
With potassium hydroxide

N-ethoxy-N-ethyl-N'-phenyl-urea (15941-86-3) → N,O-diethylhydroxylamine (4747-28-8)

Conditions	Yield
With aniline at 150℃;

ethyl N-hydroxylcarbamate (589-41-3) + ethyl iodide (75-03-6) → N,O-diethylhydroxylamine (4747-28-8)

Conditions	Yield
With hydrogenchloride; hydroxide 1.) Jones method, 2.) alkylation in basic media; Multistep reaction;

hydrogenchloride (7647-01-0) + ethoxy-ethyl-carbamic acid ethyl ester (67549-00-2) → N,O-diethylhydroxylamine (4747-28-8)

ethoxy-ethyl-carbamic acid ethyl ester (67549-00-2) + alcoholic KOH-solution → N,O-diethylhydroxylamine (4747-28-8)

ethoxy-ethyl-carbamic acid ethyl ester (67549-00-2) + KOH-solution → N,O-diethylhydroxylamine (4747-28-8)

Conditions	Yield
at 100℃;

ethoxy-ethyl-carbamic acid ethyl ester (67549-00-2) + phosphorus pentachloride (10026-13-8, 874483-75-7) + water (7732-18-5) → N,O-diethylhydroxylamine (4747-28-8) + ethoxy-ethyl-carbamoyl chloride

Conditions	Yield
bei aufeinanderfolgender Behandlung;

hydrogenchloride (7647-01-0) + N,O-diethyl-N-thiocyanato-hydroxylamine (857812-32-9) → N,O-diethylhydroxylamine (4747-28-8) + HSCN + HCN + H2SO4

Conditions	Yield
Hydrolysis;

hydrogenchloride (7647-01-0) + N-ethoxy-N-ethyl-N'-phenyl-urea (15941-86-3) → N,O-diethylhydroxylamine (4747-28-8) + methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) + aniline (62-53-3)

C6H13NO2 → N,O-diethylhydroxylamine (4747-28-8)

Conditions	Yield
With sulfuric acid at 80℃; for 3h;

2-(2-bromoethyl)isoindoline-1,3-dione (574-98-1) + N,O-diethylhydroxylamine (4747-28-8) → N-<2-(N-ethoxy-N-ethylamino)ethyl>phthalimide

Conditions	Yield
With sodium iodide In dimethyl sulfoxide at 65℃; for 7h;	39%

4-chloro-5,6,7,8-tetrahydroquinazoline-2-ylamine (111896-77-6) + N,O-diethylhydroxylamine (4747-28-8) → N-(2-Amino-5,6,7,8-tetrahydroquinazoline-4-yl)-N-(2-ethoxyethyl)amine (259272-73-6)

Conditions	Yield
With triethylamine In N-methyl-acetamide	32.4%

oxirane (75-21-8) + N,O-diethylhydroxylamine (4747-28-8) → 2-(ethoxy-ethyl-amino)-ethanol (98961-83-2)

diethyl ether (60-29-7) + N,O-diethylhydroxylamine (4747-28-8) + thiocyanogen (505-14-6) → N,O-diethyl-N-thiocyanato-hydroxylamine (857812-32-9)

Conditions	Yield
analog verlaeuft die Einw. von O.N-Dibenzyl-hydroxylamin;

N,O-diethylhydroxylamine (4747-28-8) + 1,3-bis-chlorocarbonyloxy-2,2-dimethyl-propane (6892-17-7) → 1,3-bis-(ethoxy-ethyl-carbamoyloxy)-2,2-dimethyl-propane (109726-23-0)

N,O-diethylhydroxylamine (4747-28-8) + 3,3-bis-chlorocarbonyloxymethyl-pentane (109096-62-0) → 3,3-bis-[(ethoxy-ethyl-carbamoyloxy)-methyl]-pentane (109596-15-8)

N,O-diethylhydroxylamine (4747-28-8) + 3,3-bis-chlorocarbonyloxymethyl-heptane (112442-62-3) → 3,3-bis-[(ethoxy-ethyl-carbamoyloxy)-methyl]-heptane (109647-61-2)

N,O-diethylhydroxylamine (4747-28-8) + 4-amino-benzoic acid-(2-chloro-ethyl ester) (3535-22-6) → 4-amino-benzoic acid-[2-(ethoxy-ethyl-amino)-ethyl ester]

Conditions	Yield
at 100℃; im Rohr;

N,O-diethylhydroxylamine (4747-28-8) + sodium allyloxide (20907-32-8) → 3-(ethoxy-ethyl-amino)-propan-1-ol (98433-80-8)

N,O-diethylhydroxylamine (4747-28-8) → ethylamine (75-04-7)

Conditions	Yield
With potassium hydroxide at 180℃;

N,O-diethylhydroxylamine (4747-28-8) → acetaldehyde (75-07-0)

Conditions	Yield
With potassium hydroxide at 180℃;

N,O-diethylhydroxylamine (4747-28-8) + benzoyl chloride (98-88-4) → N-ethoxy-N-ethylbenzamide (26893-77-6)

Conditions	Yield
With diethyl ether

N,O-diethylhydroxylamine (4747-28-8) + isopropyl alcohol (67-63-0) → ethanamine hydrochloride (557-66-4)

Conditions	Yield
at 150℃; Das Hydrochlorid reagiert;

N,O-diethylhydroxylamine (4747-28-8) + 3-Methylbenzoyl chloride (1711-06-4) → 3-methyl-benzoic acid-(ethoxy-ethyl-amide) (106269-96-9)

Conditions	Yield
With benzene

diethyl ether (60-29-7) + N,O-diethylhydroxylamine (4747-28-8) + methyl iodide (74-88-4) → N,O-diethyl-N-methyl-hydroxylamine

N,O-diethylhydroxylamine (4747-28-8) + methyl iodide (74-88-4) → N,O-diethyl-N-methyl-hydroxylamine

Conditions	Yield
With diethyl ether

formaldehyd (50-00-0) + N,O-diethylhydroxylamine (4747-28-8) → N,N'-Diaethoxy-N,N'-diaethyl-methylendiamin (6919-50-2)

potassium cyanate (590-28-3) + N,O-diethylhydroxylamine (4747-28-8) → N-Aethyl-N-aethoxy-harnstoff (15941-93-2)

Conditions	Yield
With hydrogenchloride

N,O-diethylhydroxylamine (4747-28-8) → N-Ethoxy-N-ethylamino-Radikal (34291-49-1)

Conditions	Yield
With di-tert-butyl peroxide In benzene Irradiation;

N,O-diethylhydroxylamine (4747-28-8) + isobutyraldehyde (78-84-2) → N,N'-Diaethoxy-N,N'-diaethyl-isobutyliden-diamin (6919-51-3)

formaldehyd (50-00-0) + N,O-diethylhydroxylamine (4747-28-8) + N-cyclohexyl-cyclohexanamine (101-83-7) → Aethoxy-aethyl-dicyclohexylaminomethyl-amin (6919-56-8)

Conditions	Yield
(i), (ii) /BRN= 605923/; Multistep reaction;

N,O-diethylhydroxylamine (4747-28-8) + diethylsulfone (597-35-3) → O,N,N-triethylhydroxylamine (4432-80-8)

Conditions	Yield
With potassium hydroxide

N,O-diethylhydroxylamine (4747-28-8) → N-nitroso-O,N-diethyl hydroxylamine (56235-95-1)

Conditions	Yield
With nitrosating agent

Upstream product

• 7647-01-0 hydrogenchloride 
• 67549-00-2 ethoxy-ethyl-carbamic acid ethyl ester 
• 857812-32-9 N,O-diethyl-N-thiocyanato-hydroxylamine 
• 15941-86-3 N-ethoxy-N-ethyl-N'-phenyl-urea 
• 10026-13-8 phosphorus pentachloride 
• 7732-18-5 water 
• 589-41-3 ethyl N-hydroxylcarbamate 
• 75-03-6 ethyl iodide 
• 74-96-4 ethyl bromide 
• 624-86-2 O-ethyl hydroxylamine 
• 64-17-5 ethanol 

Downstream Products

• 75-04-7 ethylamine 
• 75-07-0 acetaldehyde 
• 6919-56-8 Aethoxy-aethyl-dicyclohexylaminomethyl-amin 
• 417720-40-2 4-(4-(3-Ethylureido)-3-fluorophenoxy)-7-methoxyquinoline-6-carboxylic acid (2-ethoxyethyl)-amide 
• 75-00-3 chloroethane 
• 64-17-5 ethanol 
• 56235-95-1 N-nitroso-O,N-diethyl hydroxylamine 
• 91644-70-1 Phenoxyessigsaeure- 
• 93149-03-2 (2-Methoxy-4-allyl-phenoxy)-essigsaeure-(N-ethoxy-N-ethyl-amid) 
• 93146-61-3 (2-Methoxy-4-propyl-phenoxy)-essigsaeure-(N-ethoxy-N-ethyl-amid) 
• 97804-99-4 <3-Methyl-6-isopropyl-phenoxy>-essigsaeure- 
• 97804-98-3 <2-Methyl-5-isopropyl-phenoxy>-essigsaeure- 
• 106269-96-9 3-methyl-benzoic acid-(ethoxy-ethyl-amide) 
• 557-66-4 ethanamine hydrochloride 

Relevant articles and documents

One-pot method for preparing O-alkyl hydroxylamine hydrochloride and N,O-dialkyl hydroxylamine hydrochloride

The invention relates to the field of organic synthesis, in particular to a one-pot method for preparing O-alkyl hydroxylamine hydrochloride and N,O-dialkyl hydroxylamine hydrochloride. The method comprises the following steps: S1, acetylation: mixing hydroxylamine hydrochloride with water and methyl acetate, and dropwise adding a sodium hydroxide solution while stirring at room temperature to obtain an intermediate acetyl hydroxylamine; S2, alkylation: dropwise adding an alkylation reagent into the reaction kettle at normal temperature, and then heating the reactants for reaction; S3, hydrolysis and purification: after the reaction is qualified, adding concentrated sulfuric acid, performing heating hydrolysis, after the reaction is qualified, adding caustic soda flakes or liquid caustic soda to adjust the pH value to 12, carrying out atmospheric distillation and hydrochloric acid acidification, cooling the product for crystallization, and centrifuging and drying the crystal to obtaina final product. According to the invention, methyl acetate is used as an acetyl protective agent, and compared with ethyl acetate, methyl acetate has the advantages of good water solubility, small reaction steric hindrance, sufficient protection, few impurities, low price and cost and the like; therefore, the method has the advantages of high product purity, simple process operation, accessible raw materials, simple wastewater components and environment friendliness, and is suitable for industrial production.