Methoxycarbonylsulfenyl chloride

Base Information

• Chemical Name: Methoxycarbonylsulfenyl chloride
• CAS No.: 26555-40-8
• Molecular Formula: C2H3 Cl O2 S
• Molecular Weight: 126.564
• Hs Code.: 29309099
• European Community (EC) Number: 247-801-3
• DSSTox Substance ID: DTXSID10181132
• Nikkaji Number: J256.597H
• Wikidata: Q83051754
• Mol file: 26555-40-8.mol

Synonyms:Methoxycarbonylsulfenyl chloride;26555-40-8;methyl chlorosulfanylformate;S-Chloro O-methyl thiocarbonate;(chlorosulfanyl)(methoxy)methanone;EINECS 247-801-3;MFCD00013648;Thiocarbonic acid, anhydrosulphide with methyl thiohypochlorite;hypochlorous (methyl carbonic) thioanhydride;Carbonothioic acid, anhydrosulfide with thiohypochlorous acid, methyl ester;Carbonothioic acid, anhydrosulfide with thiohypochlorous acid (1:1), methyl ester;Methoxycarbonylsulfenylchloride;SCHEMBL126763;C2-H3-Cl-O2-S;(chlorothio)(methoxy)oxomethane;methoxy carbonylsulfenyl chloride;methoxy-carbonylsulfenyl chloride;methoxycarbonyl sulfenyl chloride;DTXSID10181132;(Chlorothio)formic acid methyl ester;(Chlorosulfanyl)(methoxy)oxomethane #;Methoxycarbonylsulfenyl chloride, 97%;AKOS006221860;FS-4443;CS-0313613;FT-0628310;M0979;D91417;A818505;J-016472;Carbonothioic acid anhydrosulfide with thiohypochlorus acid, O-methyl ester

Chemical Property of Methoxycarbonylsulfenyl chloride

Chemical Property:

• Appearance/Colour: CLEAR BRIGHT YELLOW LIQUID
• Vapor Pressure: 8.44mmHg at 25°C
• Refractive Index: n20/D 1.481(lit.)
• Boiling Point: 133.5°Cat760mmHg
• Flash Point: 34.5°C
• PSA: 51.60000
• Density: 1.4g/cm³
• LogP: 1.63980
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Miscible with dichlormethane.
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 125.9542282
• Heavy Atom Count: 6
• Complexity: 55.5

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methoxycarbonylsulfenyl chloride ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C
• Statements: 10-34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)SCl
• Uses: Methoxycarbonylsulfenyl chloride is used to prepare 3-[(methoxycarbonyl)dithio]-L-alanine by reacting with L-cysteine. Further, it is used in the synthesis of 3-2 pyridinyldithio propanoic acid hydrazide (PDPH). It serves as an important heterobifunctional crosslinker, which is a crosslinker used to make macromolecule-drug conjugates. Methoxycarbonylsulfenyl chloride may be used to prepare 3-[(methoxycarbonyl)dithio]-L-alanine, via reaction with L-cysteine. It is suitable for use in the synthesis of 3-2 pyridinyldithio propanoic acid hydrazide (PDPH), an important heterobifunctional crosslinker widely used in bioconjugate techniques for making macromolecule-drug conjugates.

Technology Process of Methoxycarbonylsulfenyl chloride

There total 9 articles about Methoxycarbonylsulfenyl 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: 88.0%

methanol (67-56-1) + chloro(chlorosulfanyl)methanone (2757-23-5) → metgoxycarbonylsulfenyl chloride (26555-40-8)

Guidance literature:

In diethyl ether; for 16h; Heating;

DOI:10.1021/jo00172a056

Reference yield: 20.0%

methanol (67-56-1) + (fluorocarbonyl)sulfenyl chloride (16829-32-6) → metgoxycarbonylsulfenyl chloride (26555-40-8)

Guidance literature:

equimolar amts. of educts;

Reference yield:

bis-methoxycarbonyl-disulfane (26555-39-5) → metgoxycarbonylsulfenyl chloride (26555-40-8)

Guidance literature:

With chlorine;

DOI:10.1002/jlac.19697300112

upstream raw materials:

bis-methoxycarbonyl-disulfane

bis(methoxycarbonyl)sulfide

methanol

chloro(chlorosulfanyl)methanone

Downstream raw materials:

Thiocarbonic acid S-[2-(4-methoxy-phenyl)-2-oxo-ethyl] ester O-methyl ester

O-methyl-S-phenyl thiolcarbonate

methylene chloride

(Ethoxycarbonyl)(methoxycarbonyl)disulfane

Refernces

• 1、 Poras, Hervé,Bonnard, Elisabeth,Fournié-Zaluski, Marie-Claude,Roques, Bernard P.. "Modulation of disulfide dual ENKephalinase inhibitors (DENKIs) activity by a transient N-protection for pain alleviation by oral route". . p. 58 - 67. Retrieved 2015/08/11.
• 2、 -. "NOVEL AMINO ACID DERIVATIVES, METHOD FOR PREPARING SAME, AND THERAPEUTIC USE THEREOF". Page/Page column 7. . Retrieved 2011/04/18.