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

Uses

N-(2,2,2-Trichloroethoxycarbonyloxy)succinimide was used 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.

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

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

Downstream Products

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

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.