764-09-0

Basic information

• Product Name: 2,2,2-Trichloroethyl Chlorosulfate
• Synonyms: 2,2,2-Trichloroethanol Chlorosulfate;2,2,2-Trichloroethyl Chlorosulfate;2,2,2-Trichloroethylsulfonylchloride;3,3,3-Trichloroethyl Chlorosulfate;Chlorosulfuric Acid 2,2,2-Trichloroethyl Ester;2,2,2-Trichloroethyl sulfurochloridate;1,1-trichloro-2-chlorosulfonyloxyethane
• CAS NO: 764-09-0
• Molecular Formula: C₂H₂Cl₄O₃S
• Molecular Weight: 247.91
• Product Categories: Metal Isotopes;Sulfur & Selenium Compounds;Aliphatics;Sulfonyl Chlorides
• Mol File: 764-09-0.mol

Chemical Properties

• Boiling Point: 32?C/0.4mmHg
• Flash Point: 100.067°C
• Appearance: /
• Density: 1.843g/cm³
• Vapor Pressure: 0.055mmHg at 25°C
• Refractive Index: 1.525
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• CAS DataBase Reference: 2,2,2-Trichloroethyl Chlorosulfate(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,2-Trichloroethyl Chlorosulfate(764-09-0)
• EPA Substance Registry System: 2,2,2-Trichloroethyl Chlorosulfate(764-09-0)

Safety Data

• Hazardous Substances Data: 764-09-0(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Oil

Uses

An alkyl

InChI:InChI=1/C2H2Cl4O3S/c3-2(4,5)1-9-10(6,7)8/h1H2

Upstream product

• 115-20-8 1,1,1-trichloroethanol 

Downstream Products

• 38793-61-2 sulfuric acid 4-nitrophenyl ester 2,2,2-trichloroethyl ester 
• 38793-60-1 Sulfuric acid p-tolyl ester 2,2,2-trichloro-ethyl ester 
• 38793-62-3 Sulfuric acid 2,4,6-trichlorophenyl 2,2,2-trichloroethyl ester 
• 653605-32-4 4-(2,2,2-trichloroethoxysulfonyloxy)benzoic acid benzyl ester 
• 864816-29-5 sulfuric acid 5-methoxy-2-(4-methoxybenzoyl)-1,4-bis-(4-methoxyphenyl)-3-[2-(4-methoxyphenyl)ethyl]-3,6-dihydropyrrolo[2,3-c]carbazol-7-yl ester 2,2,2-trichloroethyl ester 
• 900504-66-7 5-methoxy-2-(4-methoxybenzyl)-3-(4-methoxyphenethyl)-1,4-bis(4-methoxyphenyl)-3,6-dihydropyrrolo[2,3-c]carbazol-7-yl 2,2,2-trichloroethyl sulfate 
• 895632-76-5 sulfuric acid 13-(3-isopropoxy-4-methoxy-phenyl)-2,10,11-trimethoxy-6-oxo-6H-5-oxa-6b-aza-dibenzo[a,i]fluoren-3-yl ester 2,2,2-trichloro-ethyl ester 
• 903587-98-4 1-(2,2,2-trichloroethoxysulfuryl)-imidazole 

Relevant articles and documents

Synthesis of per-sulfated flavonoids using 2,2,2-trichloro ethyl protecting group and their factor Xa inhibition potential

The synthesis of per-sulfated flavonoids, organic compounds with multiple sulfate groups, is challenging. We present here a two-step synthesis of fully sulfated flavonoids in high overall yields using the 2,2,2-trichloroethyl moiety as a protecting group.

Iridium-Catalyzed Aryl C-H Sulfonamidation and Amide Formation Using a Bifunctional Nitrogen Source

A new strategy for the sequential formation of aryl and amidyl C-N bonds is reported. Using trichloroethoxysulfonyl azide as a bifunctional nitrogen source, Ir-catalyzed aryl C-H sulfonamidation and subsequent desulfonative amide formation proceed effectively without any need of oxidants or coupling reagents. This protocol is suitable for readily available benzamides and stable carboxylates including primary, secondary, and tertiary alkyl, alkenyl, and phenyl carboxylates, thereby providing a direct and efficient method for the synthesis of biologically and chemically useful N-arylamides.

Design and synthesis of biphenyl and biphenyl ether inhibitors of sulfatases

Inhibitors of sulfatase-2 are putative anticancer agents, but the discovery of potent small molecules targeting this enzyme has proved challenging. Based on molecular modelling, two series of sulfatase-2 inhibitors have been developed with biphenyl and biphenyl ether scaffolds judiciously substituted with sulfamate, carboxylate and other polar groups (e.g. amino). Inhibition of aryl sulfatase A and B was also determined. The biphenyl ether derivatives were less selective for sulfatase-2 over aryl sulfatase B than the biphenyl series. All biphenyl ether derivatives inhibited aryl sulfatase A, whereas only amino derivatives inhibited aryl sulfatase B significantly. In the biphenyl series few derivatives exhibited activity against aryl sulfatase B. The trichloroethylsulfamate group was identified as a new pharmacophore enabling potent inhibition of all of the sulfatases studied.

A concise and scalable strategy for the total synthesis of dictyodendrin B based on sequential C-H functionalization

A sequential C-H functionalization strategy for the synthesis of the marine alkaloid dictyodendrin B is reported. Our synthesis begins from commercially available 4-bromoindole and involves six direct functionalizations around the heteroarene core as part of a gram-scale strategy towards the natural product.

Sulfation of deoxynivalenol, its acetylated derivatives, and T2-toxin

The synthesis of several sulfates of trichothecene mycotoxins is presented. Deoxynivalenol (DON) and its acetylated derivatives were synthesized from 3-acetyldeoxynivalenol (3ADON) and used as substrate for sulfation in order to reach a series of five different DON-based sulfates as well as T2-toxin-3-sulfate. These substances are suspected to be formed during phase-II metabolism in plants and humans. The sulfation was performed using a sulfuryl imidazolium salt, which was synthesized prior to use. All protected intermediates and final products were characterized via NMR and will serve as reference materials for further investigations in the fields of toxicology and bioanalytics of mycotoxins.

Sulfation of deoxynivalenol, its acetylated derivatives, and T2-toxin

The synthesis of several sulfates of trichothecene mycotoxins is presented. Deoxynivalenol (DON) and its acetylated derivatives were synthesized from 3-acetyldeoxynivalenol (3ADON) and used as substrate for sulfation in order to reach a series of five different DON-based sulfates as well as T2-toxin-3-sulfate. These substances are suspected to be formed during phase-II metabolism in plants and humans. The sulfation was performed using a sulfuryl imidazolium salt, which was synthesized prior to use. All protected intermediates and final products were characterized via NMR and will serve as reference materials for further investigations in the fields of toxicology and bioanalytics of mycotoxins.

Sulfation of β-resorcylic acid esters - First synthesis of zearalenone-14-sulfate

The chemical sulfation of β-resorcylic acid esters was investigated by applying state of the art procedures for the synthesis and deprotection of 2,2,2-trichloroethyl protected sulfates as appropriate intermediates. The selectivity of monosulfation was st

From homogeneous to heterogeneous catalysis of the three-component coupling of oxysulfonyl azides, alkynes, and amines

A reliable procedure for the synthesis of oxysulfonyl azides has been developed and applied to the three-component coupling reactions of azides, alkynes, and amines catalyzed homogeneously by CuI, which led to the formation of N-oxysulfonyl amidines with

ALKENE AZIRIDINATION

A process for the asymmetric aziridination of an alkene comprising treating the alkene with a sulfonyl azide, preferably trichloroethoxysulfonyl azide, in the presence of a cobalt(II) porphyrin.

O- and N-sulfations of carbohydrates using sulfuryl imidazolium salts

(Chemical Equation Presented) A series of sulfuryl imidazolium salts (SISs) were prepared and examined as reagents for incorporating trichloroethyl- protected sulfate esters into carbohydrates. The SIS that contained a 1,2-dimethylimidazolium moiety (SIS