2-(Chloromethyl)benzaldehyde

Base Information

• Chemical Name: 2-(Chloromethyl)benzaldehyde
• CAS No.: 108683-62-1
• Molecular Formula: C8H7ClO
• Molecular Weight: 154.596
• Hs Code.: 2913000090
• DSSTox Substance ID: DTXSID20550557
• Nikkaji Number: J2.917.739B
• Mol file: 108683-62-1.mol

Synonyms:2-(CHLOROMETHYL)BENZALDEHYDE;108683-62-1;2-Chloromethyl-benzaldehyde;Benzaldehyde, 2-(chloromethyl)-;chloromethylbenzaldehyde;2-chloromethylbenzaldehyde;SCHEMBL1350340;DTXSID20550557;QQJODMUSGDSKPF-UHFFFAOYSA-N;MFCD19233162;AKOS006385352;SB30597

Chemical Property of 2-(Chloromethyl)benzaldehyde

Chemical Property:

• Boiling Point: 252.0±15.0 °C(Predicted)
• PSA: 17.07000
• Density: 1.200±0.06 g/cm3(Predicted)
• LogP: 2.23790
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 154.0185425
• Heavy Atom Count: 10
• Complexity: 114

Purity/Quality:

97% ^*data from raw suppliers

2-(Chloromethyl)benzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)CCl)C=O
• Uses: 2-(Chloromethyl)benzaldehyde acts as a reagent in the preparation of 2-formylbenzylphosphoric acid derivatives for the treatment of diseases caused by viruses. Reagent for the preparation of isochromanones via N-heterocyclic carbene-catalyzed annulation of in-situ generated o-quinodimethanes with ketones.

Technology Process of 2-(Chloromethyl)benzaldehyde

There total 3 articles about 2-(Chloromethyl)benzaldehyde 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: 87.3%

α,α,α'-trichloro-o-xylene (30293-58-4) → 2-(chloromethyl)benzaldehyde (108683-62-1)

Guidance literature:

With sulfuric acid; In water; at 25 ℃; for 5h;

Reference yield: 53.0%

2-cyanobenzyl chloride (612-13-5) → 2-(chloromethyl)benzaldehyde (108683-62-1)

Guidance literature:

2-cyanobenzyl chloride; With diisobutylaluminium hydride; In hexane; dichloromethane; at 0 - 20 ℃; for 4.41667h; Inert atmosphere;

With hydrogenchloride; water; In hexane; dichloromethane; at 0 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/acs.orglett.6b02335

Reference yield:

2-(chloromethyl)-phenyl methanol (142066-41-9) → 2-(chloromethyl)benzaldehyde (108683-62-1)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane;

DOI:10.1055/s-2007-984526

upstream raw materials:

2-(chloromethyl)-phenyl methanol

α,α,α'-trichloro-o-xylene

2-cyanobenzyl chloride

Downstream raw materials:

2-benzofuran-1(3H)-one

2-benzyl-2H-isoindole

2-(β-Phenylethyl)-2H-isoindol

Refernces

• 1、 Janssen-Müller, Daniel,Singha, Santanu,Olyschl?ger, Theresa,Daniliuc, Constantin G.,Glorius, Frank. "Annulation of o-Quinodimethanes through N-Heterocyclic Carbene Catalysis for the Synthesis of 1-Isochromanones". supporting information. p. 4444 - 4447. Retrieved 2016/09/09.