66065-85-8

Basic information

• Product Name: N-(2,2,2-TRICHLOROETHOXYCARBONYLOXY)SUCCINIMIDE
• Synonyms: SUCCINIMIDYL 2,2,2-TRICHLOROETHYL CARBONATE;N-(2,2,2-TRICHLOROETHOXYCARBONYLOXY)SUCCINIMIDE;Troc-OSU;Troc-OSU Succinimidyl-2,2,2-trichloroethylcarbonate;N-(2,2,2-Trichloroethoxycarbonyloxy)succiniMide, 98+%;2,5-Dioxopyrrolidin-1-yl (2,2,2-trichloroethyl) carbonate;N-(2,2,2-Trichloroethoxycarbonyloxy)succinimide
• CAS NO: 66065-85-8
• Molecular Formula: C₇H₆Cl₃NO₅
• Molecular Weight: 290.49
• Product Categories: Building Blocks;Carbonates;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 66065-85-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 111-113 °C(lit.)
• Boiling Point: 327.5 °C at 760 mmHg
• Flash Point: 151.9 °C
• Appearance: /
• Density: 1.69 g/cm³
• Vapor Pressure: 0.000201mmHg at 25°C
• Refractive Index: 1.55
• Storage Temp.: 2-8°C
• Solubility: Soluble in dioxane, THF, DMF, CH2Cl2, alcohols, and most common
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: N-(2,2,2-TRICHLOROETHOXYCARBONYLOXY)SUCCINIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2,2,2-TRICHLOROETHOXYCARBONYLOXY)SUCCINIMIDE(66065-85-8)
• EPA Substance Registry System: N-(2,2,2-TRICHLOROETHOXYCARBONYLOXY)SUCCINIMIDE(66065-85-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37
• Safety Statements: 26-27-28-36/37/39-60-36/37-9
• RIDADR: UN 3335
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 66065-85-8(Hazardous Substances Data)

Usage

Description

N-(2,2,2-TRICHLOROETHOXYCARBONYLOXY)SUCCINIMIDE, also known as trichloroethoxycarbonyloxy succinimide, is a chemical compound with the molecular formula C9H8Cl3NO4. It is a derivative of succinimide, featuring a trichloroethoxycarbonyloxy group attached to the nitrogen atom. N-(2,2,2-TRICHLOROETHOXYCARBONYLOXY)SUCCINIMIDE is known for its reactivity and is commonly utilized in organic synthesis as an intermediate for the preparation of various pharmaceuticals and other organic compounds.

Uses

Used in Pharmaceutical Synthesis:
N-(2,2,2-TRICHLOROETHOXYCARBONYLOXY)SUCCINIMIDE is used as a synthetic intermediate for the preparation of complex organic molecules, particularly in the pharmaceutical industry. Its unique reactivity allows for the formation of diverse chemical structures, which can be further modified to create potential drug candidates.
Used in Organic Chemistry:
In the field of organic chemistry, N-(2,2,2-TRICHLOROETHOXYCARBONYLOXY)SUCCINIMIDE is used as a protecting group for amines. The trichloroethoxycarbonyloxy group can be selectively introduced and removed under mild conditions, making it a valuable tool for the synthesis of various organic compounds, including those with potential applications in materials science and chemical research.
Used in Synthesis of Specific Compounds:
N-(2,2,2-TRICHLOROETHOXYCARBONYLOXY)SUCCINIMIDE is used as a key intermediate in the synthesis of methyl [phenyl 5-(2,2,2-trichloroethoxycarbonylamino)-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid]-onate and phenyl 3,4-di-O-benzyl-6-O-(tert-butyl-dimethyl-silyl)-1-selanyl-2-(2,2,2-trichloroethoxycarbonylamine)-β-D-galactopyranoside. These compounds have potential applications in the development of new drugs and pharmaceuticals, showcasing the versatility of N-(2,2,2-TRICHLOROETHOXYCARBONYLOXY)SUCCINIMIDE in organic synthesis.

InChI:InChI=1/C7H6Cl3NO5/c8-7(9,10)3-15-6(14)16-11-4(12)1-2-5(11)13/h1-3H2

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 17341-93-4 2,2,2-Trichloroethyl chloroformate 
• 82911-72-6 dicyclohexylamine salt of N-hydroxysuccinimide 

Downstream Products

• 37888-21-4 2,2,2-Trichloroethyloxycarbonyl-L-Phenylalanine 
• 82911-82-8 (S)-3-(4-Hydroxy-phenyl)-2-(2,2,2-trichloro-ethoxycarbonylamino)-propionic acid benzyl ester 
• 82911-81-7 benzyl N-(2,2,2-trichloroethoxycarbonyl)-L-serine 
• 121903-77-3 [5-(3-{Benzyloxycarbonyl-[4-(2,2,2-trichloro-ethoxycarbonylamino)-butyl]-amino}-propionylamino)-pentyl]-carbamic acid tert-butyl ester 
• 73352-56-4 3,6'-bis-N-benzyloxycarbonyl-1-N-(2,2,2-trichloroethoxycarbonyl)gentamicin B 
• 79310-13-7 3,2',6'-tris-N-(4-methoxybenzyloxycarbonyl)-1-N-(2,2,2-trichloroethoxycarbonyl)sisomicin 
• 253143-27-0 (S)-3-(3-Hydroxy-phenyl)-2-(2,2,2-trichloro-ethoxycarbonylamino)-propionic acid 
• 741702-28-3 N-(2,2,2-trichloroethoxycarbonyl)-(R)-cyclohexylalanine 
• 402948-42-9 methyl [phenyl 5-(2,2,2-trichloroethoxycarbonylamino)-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid]onate 
• 945634-63-9 phenyl 3,4-di-O-benzyl-6-O-(tert-butyl-dimethyl-silyl)-1-seleno-2-deoxy-2-{[(2,2,2-trichloroethoxy)carbonyl]amino}-α-D-galactopyranoside 
• 1037058-94-8 (6E)-5-{allyl[(2,2,2-trichloroethoxy)carbonyl]amino}-5,6,7-trideoxy-7-phenyl-D-gluco-hept-6-enitol 
• 610763-54-7 (2S,4S,5R,6R)-4-Acetoxy-2-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant articles and documents

Development of a facile method for polypeptide synthesis. Synthesis of bovine pancreatic trypsin inhibitor (BPTI)

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Introduction of 9-fluorenylmethyloxycarbonyl, trichloroethoxycarbonyl, and benzyloxycarbonyl amine protecting groups into O-unprotected hydroxyamino acids using succinimidyl carbonates

9-Fluorenylmethyl succinimidyl, pentachlorophenyl, and benzotriazole-1-yl carbonates were prepared and their reactivity with L-serine and L-serine benzyl ester was compared.The most efficient reagent, 9-fluorenylmethyl succinimidyl carbonate, was used for the preparation of 9-flourenylmethyloxycarbonyl derivatives of other hydroxyamino acids and hydroxyamino acid esters in high yields.The use of trichloroethyl and benzyl succinimidyl carbonates for an efficient conversion of hydroxyamino acids and their esters into the corresponding N-trichloroethoxycarbonyl and benzyloxycarbonyl derivatives is described.