38945-21-0

Basic information

• Product Name: O-ALLYLHYDROXYLAMINE HYDROCHLORIDE
• Synonyms: O-ALLYLHYDROXYLAMINE HYDROCHLORIDE;O-(2-PROPENYL)HYDROXYLAMINE HYDROCHLORIDE;O-ALLYHYDROXYAMINE HYDROCHLORIDE);(Allyloxy)amine hydrochloride;3-(Aminooxy)prop-1-ene hydrochloride;HydroxylaMine, O-2-propenyl-, hydrochloride;O-Allylhydroxylamine hydrochloride >=98.0% (AT);O-prop-2-enylhydroxylamine hydrochloride
• CAS NO: 38945-21-0
• Molecular Formula: C3H8ClNO
• Molecular Weight: 109.55
• EINECS: 254-203-6
• Product Categories: Hydroxylamines (O-Substituted);Hydroxylamines
• Mol File: 38945-21-0.mol
• Article Data: 18

Chemical Properties

• Melting Point: ~170 °C (dec.)
• Boiling Point: 123.2 °C at 760 mmHg
• Flash Point: 38.7 °C
• Appearance: /
• Density: 0.878g/cm3
• Vapor Pressure: 13.5mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• BRN: 3552394
• CAS DataBase Reference: O-ALLYLHYDROXYLAMINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: O-ALLYLHYDROXYLAMINE HYDROCHLORIDE(38945-21-0)
• EPA Substance Registry System: O-ALLYLHYDROXYLAMINE HYDROCHLORIDE(38945-21-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 3-9
• Hazardous Substances Data: 38945-21-0(Hazardous Substances Data)

Usage

Preparation

To a solution of 86.8 gm (1.55 moles) of potassium hydroxide in 330 ml of absolute ethanol is added a solution of 159 gm (1.52 moles) of ethyl N-hydroxycarbamate in 330 ml of absolute ethanol. With external cooling to maintain an internal temperature of 25°C to this mixture is added 195.5 gm (1.62 moles) of allyl bromide. After the addition has been com-pleted, the mixture is heated under reflux for 2 hr. After separating the potassium bromide formed during the reaction and washing it with abso-lute alcohol, the alcoholic solution is evaporated under reduced pressure. The residue is dissolved in ether and then the ether solution is extracted repeatedly with 10% aqueous sodium hydroxide solution. [From the ether solution, on evaporation 25.5 gm (18%) of ethyl N,O-diallylhydroxycar-bamate, b.p. 91-92°C (8.55 mm Hg) may be isolated.] The aqueous ex-tract is acidified with 10% aqueous sulfuric acid and the ethyl O-allylhy-droxycarbamate is extracted with ether. Upon evaporating the ether off, 134.2 gm (61%) of the intermediate product, b.p. 107°C (12.5 mm Hg), is isolated. In a steam distillation apparatus, 134 gm of ethyl O-allylhydroxy-carbamate is treated with a solution of 120 gm of potassium hydroxide in 280 ml of water. The product is steam-distilled into a receiver containing dilute hydrochloric acid. The steam distillate is evaporated under reduced pressure. The residue is taken up twice in absolute ethanol and dried by evaporation under re-duced pressure. The yield is 91 gm (55%, overall), m.p. 169-170°C. Upon recrystallization from absolute alcohol and dry ether, the melting point is raised to 170.6-170.8°C (172-174°C). Free O-allylhydrox-ylamine has the following reported properties: b.p. 98-99°C, n25D 1.4300. The problems connected with the preparation of O-arylhydroxylamines by this method have been attributed to the instability of the aryl- substituted aminooxy group to the hydrolytic system used in its prepara-tion. This problem has recently been circumvented by substituting for ethyl N-hydroxycarbamate, t-butyl N-hydroxycarbamate.

InChI:InChI=1/C3H7NO.ClH/c1-2-3-5-4;/h2H,1,3-4H2;1H

Upstream product

• 124590-94-9 N-acryloxysuccinimide 
• 6542-54-7 O-Allylhydroxylamine 
• 42832-42-8 N-(allyloxy)acetamide 
• 67160-15-0 ethyl O-allyl acetohydroxamate 
• 542-75-6 E/Z-1,3-Dichloropropene 
• 195708-27-1 N-(prop-2-en-1-yloxy)carbamic acid 1,1-dimethylethyl ester 
• 39020-79-6 2-(allyloxy)isoindoline-1,3-dione 
• 524-38-9 N-hydroxyphthalimide 
• 106-95-6 allyl bromide 
• 42832-36-0 N-Benzoyl-O-allylhydroxylamine 

Downstream Products

• 94058-71-6 O-Allyl ether of pulegone oxime 
• 126759-78-2 3-<1-(allyloximino)ethyl>-4-hydroxy-6-phenylthiomethyl-2-pyrone 
• 115651-38-2 5-<1-(Allyloxyimino)ethyl>-2-amino-4-hydroxy-benzonitril 
• 71350-23-7 4-methylcyclohexanone oxime O-allyl ether 
• 83777-38-2 N-Allyloxy-benzenesulfonamide 
• 717134-65-1 N-allyloxy-2-[3-((E)-2-pyridin-2-yl-vinyl)-1H-indazol-6-ylamino]-benzamide 
• 869089-90-7 N-(O-allylhydroxyl)-4-methoxyphenylacetamide 
• 87820-97-1 2-[1(Allyloxyimino)butyl]-3-hydroxy-5-mesitylcyclohex-2-en-1-one 
• 1012081-07-0 C₁₆H₂₄NO₄P 
• 1001592-25-1 E,E-2-benzylidenecyclopentanone O-allyloxime 

Relevant articles and documents

Design, synthesis and evaluation of wound healing activity for β-sitosterols derivatives as potent Na+/K+-ATPase inhibitors

β-Sitosterols, is a common steroid that can be identified in a variety of plants and their efficacy in promoting wound healing has been demonstrated. Na+/K+-ATPase, more than a pump, its signal transduction function for involvement in cell growth regulation attracts widespread concern. The Na+/K+-ATPase/Src receptor complex can serve as a receptor involved in multiple signaling pathways including promoting wound healing pathways. To finding potent accelerating wound healing small molecular, we choose the high inhibitory activity of Na+/K+-ATPase and non-cardiotoxic natural compound, β-sitosterol as the substrate. A series of β-sitosterol derivatives were designed, synthesized and evaluated as potential Na+/K+-ATPase inhibitors. Among them, compounds 31, 47, 49, showed improved inhibitory activity on Na+/K+-ATPase, with IC50 value of 3.0 μM, 3.4 μM, 2.2 μM, which are more potent than β-sitosterol with IC50 7.6 μM. Especially, compound 49 can induce cell proliferation, migration and soluble collagen production in L929 fibroblasts. Compared to model, compound 49 can accelerate wound healing in SD rats. Further studies indicated that 49 can activate the sarcoma (Src), uptake the protein kinase B (Akt), extracellular signal-regulated kinase (ERK) proteins expression in a concentration dependent manner. Finally, binding mode of compound 49 with Na+/K+-ATPase was studied, which provides insights into the determinants of potency and selectivity. These results proved β-stitosterol derivative 49 can serve as an effective inhibitor of Na+/K+-ATPase and potential candidate for accelerating wound healing agents.

O - substituted hydroxylamine hydrochloride and its preparation method (by machine translation)

The present invention provides a O - substituted hydroxylamine hydrochloride and its preparation, wherein the preparation method comprises the following steps: step S1, to the acetyl hydroximic acid ethyl ester in ethanol solution of adding sodium hydroxide, in addition at the same time instillment halohydrocarbon, chloride or acyl chloride substitution reaction to take place, then added to the water in order to separate out the O - substituted [...]; step S2, the said O - substituted [...] adding hydrochloric acid solution in order to produce reflux reaction O - substituted hydroxylamine hydrochloride. According to the embodiment of the invention of the O - substituted hydroxylamine hydrochloride of the preparation method, high purity of the product can be obtained, and the method is safe, easy to process, the process is simple, and is suitable for industrial production. (by machine translation)

Industrialization method for synthesizing O-chloropropene hydroxylamine by virtue of one-pot method

The invention discloses an industrialization method for synthesizing O-chloropropene hydroxylamine by virtue of a one-pot method and a catalyst utilized in the industrialization method. The industrialization method comprises the following steps: adding acetic ester, hydroxylammonium salt and a catalyst A into a reaction kettle, adding alkali metal hydroxide, and stirring to react at 0-50 DEG C for 0-10 hours so as to generate acetohydroxamic acid; continuing to add a catalyst B and dichloropropene into reaction liquid to generate etherification reaction at 20-80 DEG C for 0-20 hours, so as to obtain N-acetyl-O-chloropropene hydroxylamine; and continuing to add protonic acid to generate acidification at 20-100 DEG C for 0-10 hours, so as to prepare O-chloropropene hydroxylammonium salt, and finally carrying out neutralization, extraction and desolvation, so as to obtain dissociative O-chloropropene hydroxylamine. The product content is higher than 99%, and the total yield is over 90%. An intermediate can be utilized for preparing high-content cyclohexenone herbicides by virtue of further reaction, is applicable to large-scale industrial production, low in cost and high in product purity and yield, and the operation is easy.