1-(Benzyloxy)-4-(chloromethyl)-2-methoxybenzene

Base Information

• Chemical Name: 1-(Benzyloxy)-4-(chloromethyl)-2-methoxybenzene
• CAS No.: 33688-50-5
• Molecular Formula: C15H15ClO2
• Molecular Weight: 262.736
• NSC Number: 169519
• DSSTox Substance ID: DTXSID00305163
• Wikidata: Q82051642
• Mol file: 33688-50-5.mol

Synonyms:1-(benzyloxy)-4-(chloromethyl)-2-methoxybenzene;33688-50-5;4-(chloromethyl)-2-methoxy-1-phenylmethoxybenzene;4-(chloromethyl)-2-methoxy-1-(phenylmethoxy)benzene;4-benzyloxy-3-methoxybenzyl chloride;NSC169519;SCHEMBL5387584;DTXSID00305163;RWYQBTIHSCUXJR-UHFFFAOYSA-N;AKOS004903252;NSC-169519

Chemical Property of 1-(Benzyloxy)-4-(chloromethyl)-2-methoxybenzene

Chemical Property:

• Vapor Pressure: 1.16E-05mmHg at 25°C
• Boiling Point: 380.8°C at 760 mmHg
• Flash Point: 141.5°C
• PSA: 18.46000
• Density: 1.163g/cm³
• LogP: 4.01300
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 262.0760574
• Heavy Atom Count: 18
• Complexity: 229

Purity/Quality:

99%min ^*data from raw suppliers

1-(Benzyloxy)-4-(chloromethyl)-2-methoxybenzene 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)CCl)OCC2=CC=CC=C2

Technology Process of 1-(Benzyloxy)-4-(chloromethyl)-2-methoxybenzene

There total 10 articles about 1-(Benzyloxy)-4-(chloromethyl)-2-methoxybenzene 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: 93.5%

4-benzyloxy-3-methoxybenzyl alcohol (33693-48-0) → 1-(benzyloxy)-4-(chloromethyl)-2-methoxybenzene (33688-50-5)

Guidance literature:

With thionyl chloride; In diethyl ether; for 6h;

DOI:10.1016/S0031-9422(97)00242-2

Reference yield:

3-methoxy-4-(phenylmethoxy)benzaldehyde (2426-87-1) → 1-(benzyloxy)-4-(chloromethyl)-2-methoxybenzene (33688-50-5)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄ / methanol / 20 °C

2: SOCl₂ / dioxane / 20 °C

With sodium tetrahydroborate; thionyl chloride; In 1,4-dioxane; methanol;

DOI:10.1016/S0960-894X(01)00403-6

Reference yield:

vanillin (121-33-5,8014-42-4) → 1-(benzyloxy)-4-(chloromethyl)-2-methoxybenzene (33688-50-5)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / acetone / Reflux; Inert atmosphere

2: sodium tetrahydroborate / methanol / 3 h / 20 °C

3: N,N-dimethyl-formamide; thionyl chloride / dichloromethane / 1 h / 0 - 20 °C

With sodium tetrahydroborate; thionyl chloride; potassium carbonate; N,N-dimethyl-formamide; In methanol; dichloromethane; acetone;

DOI:10.1016/j.bmcl.2014.10.092

upstream raw materials:

4-benzyloxy-3-methoxybenzyl alcohol

3-methoxy-4-(phenylmethoxy)benzaldehyde

benzyl bromide

vanillin

Downstream raw materials:

2-(4-(benzyloxy)-3-methoxyphenyl)acetonitrile

4-benzyloxy-3-methoxy-benzylamine

C₂₃H₁₉NO₄

1-(4-(benzyloxy)-3-methoxybenzyl)-6,7-dimethoxyisoquinoline

Refernces

• 1、 Tangdenpaisal, Kassrin,Worayuthakarn, Rattana,Karnkla, Supatra,Ploypradith, Poonsakdi,Intachote, Pakamas,Sengsai, Suchada,Saimanee, Busakorn,Ruchirawat, Somsak,Chittchang, Montakarn. "Designing new analogs for streamlining the structure of cytotoxic lamellarin natural products". . p. 925 - 937. Retrieved 2015/03/31.
• 2、 Badarau, Eduard,Dilly, Sbastien,Wouters, Johan,Seutin, Vincent,Ligeois, Jean-Franois. "Chemical modifications of the N-methyl-laudanosine scaffold point to new directions for SK channels exploration". supporting information. p. 5616 - 5620. Retrieved 2015/01/08.