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

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

N-(4-methoxy-benzyl)-phenothiazine

N-(4-methoxy-benzyl)-N-(1-methyl-[4]piperidyl)-aniline

Refernces

• 1、 Rivero,Somanathan,Hellberg. "Triphosgene/triphenylphosphine: A mild reagent for the conversion of alcohols to chlorides". . p. 711 - 714. Retrieved 1993.
• 2、 Mullens, Peter,Cleator, Ed,McLaughlin, Mark,Bishop, Brian,Edwards, John,Goodyear, Adrian,Andreani, Teresa,Jin, Yan,Kong, Jongrock,Li, Hongmei,Williams, Michael,Zacuto, Michael. "Two approaches to the chemical development and large-scale preparation of a pyrimidyl tetrazole intermediate". . p. 1075 - 1087. Retrieved 2016.
• 3、 Cullen, Danica R.,Gallagher, Ashlee,Duncan, Caitlin L.,Pengon, Jutharat,Rattanajak, Roonglawan,Chaplin, Jason,Gunosewoyo, Hendra,Kamchonwongpaisan, Sumalee,Payne, Alan,Mocerino, Mauro. "Synthesis and evaluation of tetrahydroisoquinoline derivatives against Trypanosoma brucei rhodesiense". . . Retrieved 2021/10/07.
• 4、 Elahi-Mohassel, Synah,Girgis, Michael,Paige, Mikell,Petruncio, Greg. "Copper-catalyzed sp3-sp3 cross-coupling of turbo grignards with benzyl halides". supporting information. . Retrieved 2021/11/17.