824-94-2 Usage
Description
4-Methoxybenzylchloride, also known as p-methoxybenzyl chloride, is an organic compound with the chemical formula C8H9ClO. It is a colorless liquid that serves as an O/N protecting group reagent in organic synthesis. 4-Methoxybenzylchloride is characterized by the presence of a methoxy group (-OCH3) attached to a benzene ring, with a chlorine atom (-Cl) attached to the benzyl group. Its mild oxidative cleavage with ceric ammonium nitrate makes it a versatile reagent in various chemical reactions.
Uses
Used in Organic Synthesis:
4-Methoxybenzylchloride is used as a protecting group reagent for hydroxyl and amine groups in organic synthesis. It provides a temporary shield to these functional groups during chemical reactions, preventing unwanted side reactions. The protecting group can be selectively removed under mild oxidative conditions, such as treatment with ceric ammonium nitrate, to regenerate the original functional group.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Methoxybenzylchloride is used as a key intermediate in the synthesis of various active pharmaceutical ingredients (APIs). Its ability to protect sensitive functional groups during the synthesis process ensures the production of high-quality APIs with desired properties and minimal side effects.
Used in Chemical Research:
4-Methoxybenzylchloride is also utilized in chemical research for the development of new synthetic methods and the study of reaction mechanisms. Its mild oxidative cleavage properties make it an attractive candidate for exploring novel reaction pathways and improving the efficiency of existing synthetic processes.
Used in Material Science:
In material science, 4-Methoxybenzylchloride can be employed as a building block for the synthesis of various functional materials, such as polymers, dendrimers, and self-assembled monolayers. Its versatility as a protecting group reagent allows for the precise control of molecular structures, enabling the development of advanced materials with tailored properties for specific applications.
Synthesis Reference(s)
Journal of Medicinal Chemistry, 20, p. 190, 1977 DOI: 10.1021/jm00212a002The Journal of Organic Chemistry, 53, p. 3634, 1988 DOI: 10.1021/jo00250a048
Purification Methods
Purify 4-anisyl chloride by fractional distillation under vacuum, and the middle fraction is redistilled at 10-6 mm at room temperature by intermittent cooling of the receiver in liquid N2, and the middle fraction is collected. [Mohammed & Kosower J Am Chem Soc 93 2709 1971, Beilstein 6 IV 2137.]
Check Digit Verification of cas no
The CAS Registry Mumber 824-94-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,2 and 4 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 824-94:
(5*8)+(4*2)+(3*4)+(2*9)+(1*4)=82
82 % 10 = 2
So 824-94-2 is a valid CAS Registry Number.
InChI:InChI=1/C8H9ClO/c1-10-8-4-2-7(6-9)3-5-8/h2-5H,6H2,1H3
824-94-2Relevant articles and documents
Facile synthesis of 3,6-diaminopyridazine
Xing, Liyan,Petitjean, Anne,Schmidt, Rolf,Cuccia, Louis
, p. 2349 - 2353 (2007)
An efficient two-step synthesis of 3,6-diaminopyridazine from 3,6-dichloropyridazine is reported. In this synthetic procedure, 4-methoxybenzylamine was used as a nitrogen source to substitute the chloro groups of 3,6-dichloropyridazine to form N,N'-bis-(4-methoxybenzyl)-pyridazine- 3,6-diamine. The 4-methoxybenzyl groups were then removed by treatment with hydrochloric acid to provide the target 3,6-diaminopyridazine with an overall yield of 78%. Copyright Taylor & Francis Group, LLC.
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Graczyk,Taylor
, p. 3255,3257,3258 (1974)
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Mechanism of solvolysis of substituted benzyl chlorides in aqueous ethanol
Denegri, Bernard,Mati?, Mirela,Va?ko, Monika
supporting information, (2021/11/22)
The mechanism of solvolyses of activated ortho-, meta- and para-substituted benzyl chlorides in aqueous ethanol has been studied by using the Hammett-Brown and Yukawa-Tsuno treatments as well as by correlating logarithms of solvolysis rate constants with relative stabilities of corresponding benzyl carbocations in water calculated at the IEFPCM-M06–2X/6-311+G(3df,3pd) level of theory. Benzyl chlorides containing strong conjugative electron-donors in the para-position solvolyze by the SN1 mechanism, whereas other activated benzyl chlorides solvolyze by the SN2 mechanism via loose transition states.
COMPOUNDS AND METHODS FOR TREATING OXALATE-RELATED DISEASES
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Paragraph 0506, (2021/02/26)
Disclosed herein are compounds and compositions for modulating glycolate oxidase, useful for treating oxalate-related diseases, such as hyperoxaluria, where modulating glycolate oxidase is expected to be therapeutic to a patent in need thereof. Methods of modulating glycolate oxidase activity in a human or animal subject are also provided.
Methods of synthesizing ionic liquids from primary alcohol-containing lignin compounds
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Page/Page column 19, (2021/06/09)
Methods and compositions are provided for synthesizing ionic liquids from lignin. Methods and compositions are also provided for treating lignin with ionic liquids.