38936-60-6

Basic information

• Product Name: 1-[(AMMONIOOXY)METHYL]-4-CHLOROBENZENE CHLORIDE
• Synonyms: o-(p-chlorobenzyl)-hydroxylaminhydrochloride;O-(4-CHLOROBENZYL)HYDROXYLAMINE HYDROCHLORIDE;1-[(AMINOOXY)METHYL]-4-CHLOROBENZENE HYDROCHLORIDE;1-[(AMMONIOOXY)METHYL]-4-CHLOROBENZENE CHLORIDE;O-(p-Chlorobenzyl)hydroxylamine hydrochloride;O-(4-chlorobenzyl) hydroxylaMine;4-Chlorobenzyloxyamine hydrochloride;O-(4-Chlorobenzyl)hydroxylamine hydrochloride 4-Chlorobenzyloxyamine hydrochloride
• CAS NO: 38936-60-6
• Molecular Formula: C₇H₈ClNO*ClH
• Molecular Weight: 194.06
• Mol File: 38936-60-6.mol
• Article Data: 12

Chemical Properties

• Melting Point: 230°C
• Boiling Point: 274 °C at 760 mmHg
• Flash Point: 119.5 °C
• Appearance: /
• Vapor Pressure: 0.00555mmHg at 25°C
• CAS DataBase Reference: 1-[(AMMONIOOXY)METHYL]-4-CHLOROBENZENE CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(AMMONIOOXY)METHYL]-4-CHLOROBENZENE CHLORIDE(38936-60-6)
• EPA Substance Registry System: 1-[(AMMONIOOXY)METHYL]-4-CHLOROBENZENE CHLORIDE(38936-60-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 38936-60-6(Hazardous Substances Data)

Usage

Preparation

To a solution of 83.7 gm (1.5 moles) of potassium hydroxide in 560 ml of water is added in turn with stirring, 300 gm (0.985 mole) of dipotassium hydroxylaminedisulfonate and 161 gm (1.0 mole) of 4-chlorobenzyl chlo-ride. The stirred mixture is heated on a steam bath for 1.75 hr. After cool-ing, the precipitate is filtered off and refluxed for 3 hr in 1000 ml of 1.5 Ν sulfuric acid. The reaction mixture is then cooled and made strongly alkaline with a 15% aqueous sodium hydroxide solution. The mixture is then extracted with ether repeatedly. The ether extracts are combined and evaporated to dryness. The solid residue (crude free base, 80 gm, i.e., 51.5% of theory, m.p. 35-38°C) is taken up in 1 liter of ether. Anhydrous hydrogen chloride is bubbled through this solution to precipitate the hy-drochloride salt. The yield is 59 gm (31%, overall), m.p. 243-244°C (dec); the free base has b.p. 100°C/1 mm Hg. In this preparation, the hydrolysis of the alkylated dipotassium hydroxyl-aminedisulfonate with only 1 liter of 1.5 Ν sulfuric acid seems somewhat skimpy. We suggest that a higher level of sulfuric acid be considered at that stage of the reaction, if the alkylation has indeed gone to completion. Once the O-alkylhydroxylamine has been prepared by this reaction, it may be N-alkylated to produce an N,Ο-dialkylhydroxylamine. The preparation of O-phenylhydroxylamine has been a synthetic chal-lenge for some time since it is quite unstable. Using hydroxylamine-O-sulfonic acid. A small quantity of this compound has been prepared [36]. Reaction conditions probably require further study to improve the yield. Extension of the reaction to the preparation of O-alkylhydroxylamines would be of interest.

InChI:InChI=1/C7H8ClNO.ClH/c8-7-3-1-6(2-4-7)5-10-9;/h1-4H,5,9H2;1H

Upstream product

• 622-95-7 4-chlorobenzyl bromide 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 39030-46-1 2-((4-chlorobenzyl)oxy)isoindoline-1,3-dione 
• 873-76-7 para-Chlorobenzyl alcohol 
• 104-88-1 4-chlorobenzaldehyde 
• 5555-70-4 N-(4-Chlor-benzyloxy)-carbaminsaeure-ethylester 
• 5555-51-1 (4-chlorobenzyl)oxyamine 

Downstream Products

• 98554-22-4 N-(4-Chlor-benzyloxy)-carbamoylchlorid 
• 109448-30-8 4-(4-Chlor-benzyloxycarbamoyl)-allophansaeure-(4-chlor-benzylester) 
• 130907-46-9 4-(4-Chlor-benzyloxy)-allophansaeure-(4-chlor-benzylester) 
• 85661-12-7 6-(4-Chloro-benzyloxy)-5,6,7,8-tetrahydro-pyrimido[4,5-d]pyrimidine-2,4-diamine 
• 244008-95-5 2-[(E)-4-Chloro-benzyloxyimino]-propionic acid ethyl ester 
• 493021-67-3 2-bromo-cyclopent-1-enecarbaldehyde O-(4-chloro-benzyl)-oxime 
• 929224-80-6 N-4-chlorobenzyloxy-4-methoxybenzenesulfonamide 
• 929225-00-3 2-(4-chlorobenzyloxyamino)hexanoic acid 
• 929225-07-0 2-(4-chlorobenzyloxyamino)-N-(tert-butyldimethylsilyloxy)acetamide 
• 929224-89-5 {4-chlorobenzyloxy[(4-methoxyphenyl)sulfonyl]amino}acetic acid 
• 929224-84-0 tert-butyl {4-chlorobenzyloxy[(4-methoxyphenyl)sulfonyl]amino}acetate 
• 929224-95-3 2-{4-chlorobenzyloxy[(4-methoxyphenyl)sulfonyl]amino}acetic acid (tert-butyldimethylsilyl)hydroxyamide 

Relevant articles and documents

Synthesis and anti-tumor activity evaluation of salinomycin C20-O-alkyl/benzyl oxime derivatives

Seventeen C20-O-alkyl/benzyl oxime derivatives were synthesized by a concise and effective method. Most of these derivatives showed tens to several hundred nanomolar IC50 values against HT-29 colorectal, HGC-27 gastric and MDA-MB-231 breast cancer cells, whose antiproliferative activity is 15-240 fold better than that of salinomycin. The C20-oxime etherified derivatives can coordinate potassium ions, and further adjust the cytosolic Ca2+ concentrations in HT-29 cells. The significant improvement of the potency should be attributed to the better ion binding and transport ability of the modified derivatives. In addition, the C20-O-alkyl/benzyl oxime derivatives showed much better selectivity indexes (SI) than salinomycin, indicating that they present lower neurotoxic risk.

Preparation method of benzyloxyamine hydrochloride

The invention discloses a preparation method of benzyloxyamine hydrochloride. The preparation method comprises the following steps: (1) dispersing ketoxime 2 and alkali metal hydroxide into a mixed solvent of dimethylacetamide and water at the temperature of 50-55 DEG C and the stirring speed of 100-120 rpm; (2) dropwise adding a benzyl halide compound 1 into a dispersion body obtained in the step (1), reacting for 130-140 minutes at the temperature of 60-65 DEG C after dropwise adding is completed, then cooling to room temperature, adding water, extracting by using normal hexane, and distilling an organic phase under reduced pressure to obtain a product 3; and (3) adding the product 3 obtained in the step (2) into a mixed solution of methanol and a hydrochloric acid solution with the mass concentration of 38% , reacting for 200-220 minutes at the temperature of 35-40 DEG C and at the stirring speed of 80-100 rpm, distilling under reduced pressure until a solid is separated out, cooling to room temperature, washing the solid with petroleum ether, and drying to obtain the target product 4-benzyloxyamine hydrochloride. According to the preparation method, the total yield can reach 95% or above, and the product purity can reach 99% or above.

Synthesis and antibacterial evaluation of (E)-1-(1H-indol-3-yl) ethanone O-benzyl oxime derivatives against MRSA and VRSA strains

Infections caused due to multidrug resistant organisms have emerged as a constant menace to human health. Even though numerous antibiotics are currently available for treating infectious diseases, a great number of bacterial strains have acquired resistance to many of them. Among these, infections caused due to Staphylococcus aureus are predominant in adult and paediatric population. Indole is a prominent chemical scaffold found in many pharmacologically active natural products and synthetic drugs. A number of oxime ether containing compounds have attracted attention of researchers owing to their interesting biological properties. Current work details the synthesis of indole containing oxime ether derivatives and their evaluation for antimicrobial activity against a panel of bacterial and mycobacterial strains. Synthesized compounds demonstrated good to moderate activity against drug-resistant S. aureus including resistant to vancomycin. Among all, compound 5h was found to possess potent activity against susceptible as well as MRSA and VRSA strains of S. aureus with MIC of 1 μg/mL and 2–4 μg/mL respectively. In addition, compound 5h was found to be non-toxic to Vero cells and exhibited good selectivity index of >40. Further, 5h, E-9a and E-9b possessed good biofilm inhibition against S. aureus. With these assuring biological properties, synthesized compounds could be potential prospective antimicrobial agents.