4-Methoxybenzyl chloride

Base Information

• Chemical Name: 4-Methoxybenzyl chloride
• CAS No.: 824-94-2
• Molecular Formula: C8H9ClO
• Molecular Weight: 156.612
• Hs Code.: 29093090
• European Community (EC) Number: 212-540-6
• NSC Number: 172955
• UNII: Q500ZS03TI
• DSSTox Substance ID: DTXSID20231718
• Nikkaji Number: J32.082J
• Wikidata: Q27287004
• Mol file: 824-94-2.mol

Synonyms:4-Methoxybenzyl chloride;824-94-2;4-methoxybenzylchloride;1-(Chloromethyl)-4-methoxybenzene;p-Methoxybenzyl chloride;p-Anisyl chloride;Benzene, 1-(chloromethyl)-4-methoxy-;alpha-Chloro-4-methoxytoluene;p-(Chloromethyl)anisole;Anisole, p-(chloromethyl)-;4-(Chloromethyl)anisole;4-Methyloxybenzyl chloride;1-Chloromethyl-4-methoxy-benzene;MFCD00000915;CCRIS 5108;.alpha.-Chloro-4-methoxytoluene;4-(chloromethyl)-1-methoxybenzene;1-(chloromethyl)-4-methoxy-benzene;EINECS 212-540-6;para-methoxybenzyl chloride;NSC 172955;1-CHLOROMETHYL-4-METHOXYBENZENE;UNII-Q500ZS03TI;Q500ZS03TI;4-(chloromethyl)phenyl methyl ether;NSC-172955;1-(chloromethyl)-4-(methyloxy)benzene;4-Chloromethyl anisole;PMBCl;p-methoxybenzylchlorid;p-methoxybenzylchoride;p-methoxybenzylchloride;PMB-Cl;4-methoxybenzylchlorine;4methoxybenzyl chloride;4-Methyoxybenzylchloride;4-methoxy benzylchloride;4-methoxybenzyl-chloride;4-Methoxy-benzylchloride;para-methoxybenzylchloride;paramethoxybenzyl chloride;4-methoxylbenzyl chloride;4-methyoxybenzyl chloride;p-methoxy benzyl chloride;4-methoxy benzyl chloride;4-methoxy-benzyl chloride;a-chloro-4-methoxytoluene;para-methoxy benzylchloride;4-methoxyl benzyl chloride;Para methoxy benzylchloride;4-(methoxy)benzyl chloride;para-Methoxy benzyl chloride;para-methoxyl benzyl chloride;SCHEMBL13096;4-methoxyphenylmethyl chloride;(4-methoxyphenyl)methyl chloride;DTXSID20231718;l-(chloromethyl)-4-methoxybenzene;4-Methoxybenzylchloride, stabilized;BCP25855;STR01214;1-(chloro methyl)-4-methoxybenzene;NSC172955;AKOS000262023;.ALPHA.-CHLORO-P-METHOXYTOLUENE;CS-W017991;AM101321;LS-188201;AM20041208;FT-0618924;M0676;EN300-49219;W-104172;Q27287004;F0001-2114;4-Methoxybenzyl chloride, contains potassium carbonate as stabilizer, 98%

Chemical Property of 4-Methoxybenzyl chloride

Chemical Property:

• Appearance/Colour: Colorless liquid
• Vapor Pressure: 0.0495mmHg at 25°C
• Melting Point: -1 °C(lit.)
• Refractive Index: n20/D 1.548(lit.)
• Boiling Point: 243.6 °C at 760 mmHg
• Flash Point: 109.4 °C
• PSA: 9.23000
• Density: 1.109 g/cm³
• LogP: 2.43400
• Storage Temp.: 2-8°C
• Water Solubility.: slowly decomposes
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 156.0341926
• Heavy Atom Count: 10
• Complexity: 87.3

Purity/Quality:

99% ^*data from raw suppliers

4-MethoxybenzylChloride(Stabilized) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)CCl
• Uses: O/N protecting group reagent which can be mildly oxidatively cleaved, e.g., with ceric ammonium nitrate.

Technology Process of 4-Methoxybenzyl chloride

There total 59 articles about 4-Methoxybenzyl chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

4-Methoxybenzyl alcohol (105-13-5) → p-methoxybenzyl chloride (824-94-2)

Guidance literature:

With 1,2,3-Benzotriazole; thionyl chloride; In dichloromethane; at 20 ℃;

DOI:10.1055/s-1999-2943

Reference yield: 98.0%

Methyl-thiocarbamic acid S-(4-methoxy-benzyl) ester (27979-81-3) → p-methoxybenzyl chloride (824-94-2)

Guidance literature:

With hydrogenchloride; N-chloro-succinimide; In acetonitrile; at 10 ℃;

DOI:10.1055/s-2006-950353

Reference yield: 82.0%

methanol (67-56-1) + 4-Methoxybenzyl alcohol (105-13-5) → 1-methoxy-4-(methoxymethyl)benzene (1515-81-7) + p-methoxybenzyl chloride (824-94-2)

Guidance literature:

4-Methoxybenzyl alcohol; With titanium tetrachloride; In chloroform; at 20 ℃; for 0.0166667h; Molecular sieve;

methanol; In chloroform; for 9h; Reflux;

DOI:10.1016/j.tet.2010.06.046

upstream raw materials:

p-methylanizole

chloromethyl methyl ether

methoxybenzene

formaldehyd

Downstream raw materials:

1-(4-methoxy-benzyl)-piperidine

N-(4-methoxybenzyl)pyrimidin-2-amine

2-{4-[2-(4-methoxy-benzyloxy)-ethyl]-piperazino}-ethanol

N-(4-methoxy-benzyl)-phenothiazine

Refernces

Highly selective total synthesis of enantiomerically pure (-)-anisomycin

10.1021/jo00357a023

The research focuses on the highly selective total synthesis of enantiomerically pure (-)-anisomycin, an antibiotic with significant activity against pathogenic protozoa and fungi, which has been used in the treatment of amebic dysentery and trichomonas vaginitis. The study's purpose was to achieve a chiral total synthesis of optically pure (-)-anisomycin through a series of virtually complete regio- and stereocontrolled reactions, without the need for isomer separation. The synthesis began with 4-O-benzyl-2,3-O-bis(methoxymethyl)-L-threose derived from diethyl L-tartrate as the chiral building block and involved several key steps, including a-chelation-controlled addition of hydride, stereospecific cyclization, and selective introduction of the acetyl group with complete regiochemical control. The process utilized various chemicals such as diethyl L-tartrate, 4-methoxybenzyl chloride, benzyl chloroformate, and protecting groups like tert-butyldimethylsilyl and methoxymethyl groups. The successful synthesis was confirmed by comparing the synthesized (-)-anisomycin with authentic samples through melting point, specific optical rotation, and NMR and mass spectrometry analysis, proving 100% enantiomeric purity. The study concluded with the investigation of the antiprotozoal and antifungal activities of the synthetic (-)-anisomycin.

Synthetic studies of incednine: synthesis of C1-C13 pentaenoic acid segment

10.1016/j.tetlet.2009.02.203

The research focuses on the stereoselective synthesis of the C1–C13 pentaenoic acid segment (4) of the novel antibiotic incednine (1), which was isolated from Streptomyces sp. and exhibits significant inhibitory activity against anti-apoptotic oncoproteins Bcl-2 and Bcl-xL. The purpose of this study is to contribute to the development of novel anti-tumor drugs and to provide a useful tool for further study of the Bcl-2 and Bcl-xL functions. The researchers achieved the synthesis through a series of chemical reactions, including olefination, Sharpless asymmetric epoxidation, and Horner–Wadsworth–Emmons olefination. Key chemicals used in the process include ethylene glycol (6), PMBCl, KOH and various other reagents and conditions necessary for the complex series of reactions that led to the final product, the C1–C13 pentaenoic acid segment 4. The successful synthesis of this key segment brings the researchers closer to the total synthesis of incednine (1), which could have significant implications in cancer treatment and research.

A chemoenzymatic asymmetric synthesis of (9S,12S,13S)- and (9S,12RS,13S)-pinellic acids

10.1016/j.tetlet.2009.06.069

The study presents a chemoenzymatic asymmetric synthesis of (9S,12S,13S)- and (9S,12RS,13S)-pinellic acids, which are significant due to their adjuvant activity for influenza vaccines. The synthesis involves several key steps and chemicals. Initially, 1,9-nonanediol is monoprotected with para-methoxybenzyl chloride (PMBCl) to form compound 3, which is then oxidized with pyridinium chlorochromate (PCC) to yield aldehyde 4. The reaction of 4 with vinylmagnesium bromide produces allylic alcohol 5. A crucial step involves Novozyme 435-catalyzed acetylation of 5 with vinyl acetate, yielding (S)-acetate 6 and (R)-alcohol 5 with high enantiomeric excesses. Another significant component, (R)-cyclohexylideneglyceraldehyde 7, is reacted with CH3(CH2)4Li to form the anti-triol derivative 8, which is then protected with tert-butyldiphenylsilyl chloride (TPSCl) to form silyl derivative 9. The acetal function of 9 is removed to yield diol 10, which is cleaved with NaIO4 to form aldehyde 11. The reaction of 11 with vinylmagnesium bromide produces allylic alcohol 12. A cross-metathesis reaction between (S)-5 and 12, catalyzed by Grubbs 2nd generation catalyst, yields diol 13. Further steps involve silylation, oxidative removal of PMB protection, oxidation to form acid 16, and final desilylation to obtain the target pinellic acids. This method highlights the use of biocatalysis and chiral templates for efficient asymmetric synthesis, offering a simpler and more efficient route to these biologically active compounds.