39545-31-8

Basic information

• Product Name: 2-CHLOROBENZYL CHLOROFORMATE
• Synonyms: 2-CL-Z-CL;CHLORAMEISENSAEURE-2-CHLORBENZYLESTER 97;2-CHLOROPHENZYL CHLOROFORMATE;2-Chlorobenzyl carbonochloridate;Carbonochloridic acid,(2-chlorophenyl)methyl ester;2-Chlorobenzyl chloroformate 97%;2-CHLOROBENZYL CHLOROFORMATE
• CAS NO: 39545-31-8
• Molecular Formula: C₈H₆Cl₂O₂
• Molecular Weight: 205.04
• Product Categories: Acid Halides;Carbonyl Compounds;Organic Building Blocks;Acid Halides;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 39545-31-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 50 °C100 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.339 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.36 psi ( 20 °C)
• Refractive Index: n20/D 1.536(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-CHLOROBENZYL CHLOROFORMATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLOROBENZYL CHLOROFORMATE(39545-31-8)
• EPA Substance Registry System: 2-CHLOROBENZYL CHLOROFORMATE(39545-31-8)

Safety Data

• Hazard Codes: T,C
• Statements: 23/24/25-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3277 6.1/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 39545-31-8(Hazardous Substances Data)

Usage

Description

2-Chlorobenzyl Chloroformate is an organic compound that is primarily utilized as a reagent in the synthesis of various pharmaceuticals and bioactive molecules. It is known for its ability to act as a potent inhibitor of Bruton's tyrosine kinase (BTK), making it a valuable compound in the development of treatments for diseases associated with this enzyme.

Uses

Used in Pharmaceutical Industry:
2-Chlorobenzyl Chloroformate is used as a BTK inhibitor for the development of therapeutic agents to prevent and/or treat diseases associated with Bruton’s tyrosine kinase. Its inhibitory action on BTK makes it a promising candidate for the treatment of conditions such as autoimmune diseases, inflammatory disorders, and certain types of cancer.
In the development of BTK inhibitors, 2-Chlorobenzyl Chloroformate is used as a key intermediate in the synthesis of these inhibitors. Its chemical properties allow for the creation of molecules that can effectively target and inhibit the activity of BTK, thereby providing potential therapeutic benefits for patients suffering from related diseases.
Additionally, 2-Chlorobenzyl Chloroformate may also find applications in other industries, such as chemical research and development, where its unique properties can be exploited for the creation of novel compounds and materials. However, the primary use of this compound is within the pharmaceutical industry, where its potential as a BTK inhibitor makes it a valuable asset in the fight against various diseases and conditions.

InChI:InChI=1/C8H6Cl2O2/c9-7-4-2-1-3-6(7)5-12-8(10)11/h1-4H,5H2

Upstream product

• 75-44-5 phosgene 
• 17849-38-6 2-Chlorobenzyl alcohol 
• 500372-17-8 O-(2-chlorobenzyl) S-methyl carbonothioate 

Downstream Products

• 42390-97-6 N^ε-(2-Chlorophenylmethoxycarbonyl)-(S)-lysine 
• 675585-53-2 (2S)-3-((3-((5-carbazol-9-yl)pentyl)isoxazol-5-yl)methoxy)-2-(2-chlorobenzyloxycarbonylamino)propionic acid methyl ester 
• 301346-06-5 t-butyl 5-fluoro-3-(2-chlorobenzyloxycarbonyl-valinamido)-4-hydroxypentanoate 
• 301346-07-6 3-[2-(2-chloro-benzyloxycarbonylamino)-3-methyl-butyrylamino]-5-fluoro-4-oxo-pentanoic acid tert-butyl ester 
• 54613-99-9 Boc-(S)-Lys(2-Cl-Z)-OH 
• 73977-22-7 N^α-t-butyloxycarbonyl-N-2-chlorobenzyloxycarbonyl-L-lysine dicyclohexylammonium salt 
• 857645-69-3 methyl 3-{2-[(2S)-2-[tert-butoxycarbonylamino]-5-[(2-chlorobenzyloxycarbonyl)amino]pentanoylamino]-phenyl}propanoate 
• 1175526-51-8 (2'-{[(2-Chloro-benzyloxycarbonyl)-ethyl-amino]-methyl}-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester 
• 1161776-63-1 {2-[2-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-4-ylmethyl]-2H-[1,2,3]triazol-4-yl}-carbamic acid 2-chloro-benzyl ester 

Relevant articles and documents

SAR development of lysine-based irreversible inhibitors of transglutaminase 2 for huntington's disease

We report a series of irreversible transglutaminase 2 inhibitors starting from a known lysine dipeptide bearing an acrylamide warhead. We established new SARs resulting in compounds demonstrating improved potency and better physical and calculated properties. Transglutaminase selectivity profiling and in vitro ADME properties of selected compounds are also reported.

Dipeptidyl aspartyl fluoromethylketones as potent caspase inhibitors: SAR of the N-protecting group

The synthesis and biological evaluation of a group of N-protected Val-Asp-fmk as caspase inhibitors is reported. This article describes the synthesis and biological evaluation of a group of N-protected Val-Asp-fmk as caspase inhibitors. The protecting group was found to contribute to caspase-3 inhibiting activity, and compounds with a large group such as Cbz are more active than compounds with a small group such as Ac. Compounds with more hydrophobic protecting groups were found to be more active in cell apoptosis protection assays, probably due to increased cell permeability. MX1122, 2,4-di-Cl-Cbz-Val-Asp-fmk, is identified as a potent broad-spectrum caspase inhibitor and is selective for caspases versus other proteases, with good activity in the cell apoptosis protection assays as well as good efficacy in the mouse liver apoptosis model.

Non-phosgene synthesis of benzyl chloroformate (CbzCl)

A novel synthetic method for benzyl chloroformate (CbzCl) using carbon monoxide or carbonyl sulfide as a carbonyl source was established. Benzyl chloroformate was successfully synthesized by the chlorination using sulfuryl chloride of S-methyl O-benzyl carbonothioate, which was prepared by the carbonylation of benzyl alcohol with carbon monoxide and sulfur (or carbonyl sulfide) in the presence of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) followed by esterification using methyl iodide.