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N-(2-Chlorobenzyloxycarbonyloxy)succinimide

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Name

N-(2-Chlorobenzyloxycarbonyloxy)succinimide

EINECS N/A
CAS No. 65853-65-8 Density 1.48 g/cm3
PSA 72.91000 LogP 1.99510
Solubility N/A Melting Point 102-105 °C(lit.)
Formula C12H10ClNO5 Boiling Point 397.4 °C at 760 mmHg
Molecular Weight 283.668 Flash Point 194.2 °C
Transport Information N/A Appearance Very faintly beige powder
Safety 22-24/25-26 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 65853-65-8 (N-(2-Chlorobenzyloxycarbonyloxy)succinimide) Hazard Symbols IrritantXi
Synonyms

2,5-Pyrrolidinedione,1-[[[(2-chlorophenyl)methoxy]carbonyl]oxy]- (9CI);2-Chlorobenzyl succinimidylcarbonate;2-Cl-Z-Osu;

 

N-(2-Chlorobenzyloxycarbonyloxy)succinimide Standards and Recommendations

Chemical Stability:
Stable under normal temperatures and pressures.
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Strong oxidants.
Hazardous Decomposition Products:
Hydrogen chloride, carbon monoxide, oxides of nitrogen, carbon
dioxide.
Hazardous Polymerization: Has not been reported.

N-(2-Chlorobenzyloxycarbonyloxy)succinimide Specification

The IUPAC name of Z(2-Cl)-OSu is (2-chlorophenyl)methyl (2,5-dioxopyrrolidin-1-yl) carbonate . With the CAS registry number 65853-65-8, it is also named as 1-({[(2-Chlorobenzyl)oxy]carbonyl}oxy)-2,5-pyrrolidinedione ; 2,5-Pyrrolidinedione, 1-[[[(2-chlorophenyl)methoxy]carbonyl]oxy]- ; N-(2-Chlorobenzyloxycarbonyloxy)succinimide ; 2-Chlorobenzyl succinimidyl carbonate .

The Z(2-Cl)-OSu is very faintly beige powder which should be stored at RT.. The product's categories are Peptide coupling agents, Amino Acid Derivatives, Medical Intermediates, N-Protecting Reagents, Biochemistry, N-Substituted Maleimides, Succinimides & Phthalimides and Z-Amino acid series.  

This product is used as amino acid protective agent. It is irritating to eyes, respiratory system and skin. So people should not breathe dust and avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

The Z(2-Cl)-OSu can be obtained by di(succinimido) carbonate and 2-chloro-benzyl alcohol with DMAP in the solvent acetonitrile and CH2Cl2 . The reaction time is 6 hour(s) and the yield is 55%.
  

This product also can be used to prepare other chemicals. For example: 1. It  can react with (3S)-trans-1-methoxy-3-[(tert-butoxycarbonyl)amino]-4-methyl-2-azetidinone to get 2-(N-tert-butoxycarbonyl)-3-(N-2-chlorobenzyloxycarbonyl-N-methoxy)-2,3-diaminobutanoic acid . 2. It reacts with N-methyl-hydroxylamine; hydrochloride to obtain N-(2-chlorobenzyloxycarbonyl)-N-methylhydroxylamine .

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.02 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): 1.02 ; (4)ACD/LogD (pH 7.4): 1.02 ; (5)ACD/BCF (pH 5.5): 3.49 ; (6)ACD/BCF (pH 7.4): 3.49 ; (7)ACD/KOC (pH 5.5): 85.17 ; (8)ACD/KOC (pH 7.4): 85.17 ; (9)#H bond acceptors: 6 ; (10)#H bond donors: 0 ; (11)#Freely Rotating Bonds: 5 ; (12)Index of Refraction: 1.596 ; (13)Molar Refractivity: 65.03 cm3 ; (14)Molar Volume: 191 cm3 ; (15)Polarizability: 25.78×10-24 cm3 ; (16)Surface Tension: 61.1 dyne/cm ; (17)Enthalpy of Vaporization: 64.79 kJ/mol ; (18)Vapour Pressure: 1.59E-06 mmHg at 25°C.

People can use the following data to convert to the molecule structure. SMILES: O=C2N(OC(=O)OCc1ccccc1Cl)C(=O)CC2; InChI: InChI=1/C12H10ClNO5/c13-9-4-2-1-3-8(9)7-18-12(17)19-14-10(15)5-6-11(14)16/h1-4H,5-7H2.

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