4-Nitrophenyl 2-(trimethylsilyl)ethyl carbonate

Base Information

• Chemical Name: 4-Nitrophenyl 2-(trimethylsilyl)ethyl carbonate
• CAS No.: 80149-80-0
• Molecular Formula: C12H17NO5Si
• Molecular Weight: 283.356
• Hs Code.: 29319090
• European Community (EC) Number: 279-406-7
• DSSTox Substance ID: DTXSID10230093
• Nikkaji Number: J320.237B
• Wikidata: Q72495888
• Mol file: 80149-80-0.mol

Synonyms:80149-80-0;4-Nitrophenyl 2-(trimethylsilyl)ethyl carbonate;4-Nitrophenyl (2-(trimethylsilyl)ethyl) carbonate;TEOC-ONp;(4-nitrophenyl) 2-trimethylsilylethyl carbonate;C12H17NO5Si;2-(trimethylsilyl)ethyl p-nitrophenyl carbonate;4-[2-(Trimethylsilyl)ethoxycarbonyloxy]nitrobenzene;2-(Trimethylsilyl)ethyl 4-nitrophenyl carbonate;EINECS 279-406-7;MFCD00042930;Tec-Onp;Carbonic acid, 4-nitrophenyl 2-(trimethylsilyl)ethyl ester;TEOC-ONP;4-Nitrophenyl-2-(trimethylsilyl)ethyl carbonate;SCHEMBL1161760;C12-H17-N-O5-Si;DTXSID10230093;ZAQWGGKIMQIVGM-UHFFFAOYSA-N;AMY39305;AKOS016003283;AS-11369;SY019076;4-nitrophenyl 2-trimethylsilylethyl carbonate;CS-0017956;FT-0702621;T2872;2-trimethylsilanylethyl 4-nitrophenyl carbonate;4-Nitrophenyl(2-(trimethylsilyl)ethyl)carbonate;C76565;A916078;J-515880;Carbonic acid 4-nitrophenyl 2-(trimethylsilyl)ethyl ester;4-Nitrophenyl 2-(trimethylsilyl)ethyl carbonate, >=95.0% (NMR);carbonic acid 4-nitro-phenyl ester 2-trimethylsilanyl-ethyl ester;Carbonic acid 4-nitro-phenyl ester-2-trimethylsilanyl-ethyl ester

Chemical Property of 4-Nitrophenyl 2-(trimethylsilyl)ethyl carbonate

Chemical Property:

• Vapor Pressure: 1.01E-05mmHg at 25°C
• Melting Point: 35-40 ºC
• Refractive Index: 1.503
• Boiling Point: 371.7 ºC at 760 mmHg
• Flash Point: 178.6 ºC
• PSA: 81.35000
• Density: 1.147 g/cm³
• LogP: 3.97160
• Storage Temp.: 2-8°C
• Sensitive.: Moisture & Light Sensitive
• Water Solubility.: Slightly soluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 283.08759918
• Heavy Atom Count: 19
• Complexity: 315

Purity/Quality:

99% ^*data from raw suppliers

4-Nitrophenyl 2-(trimethylsilyl)ethyl carbonate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[Si](C)(C)CCOC(=O)OC1=CC=C(C=C1)[N+](=O)[O-]
• Uses: It is employed as a reagent for the introduction of the TEOC-amino protecting group which can be cleaved by F-.

Technology Process of 4-Nitrophenyl 2-(trimethylsilyl)ethyl carbonate

There total 2 articles about 4-Nitrophenyl 2-(trimethylsilyl)ethyl carbonate 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: 97.0%

2-(Trimethylsilyl)ethanol (2916-68-9) + 4-Nitrophenyl chloroformate (7693-46-1) → 2-(Trimethylsilyl)ethyl 4-nitrophenyl carbonate (80149-80-0)

Guidance literature:

With triethylamine; In acetonitrile; at 0 ℃;

DOI:10.1016/S0960-894X(98)00114-0

Reference yield:

trimethylsilanyl-acetic acid ethyl ester (4071-88-9) → 2-(Trimethylsilyl)ethyl 4-nitrophenyl carbonate (80149-80-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 78.1 percent / BH₃*THF / tetrahydrofuran / 48 h / Ambient temperature

2: 87 percent / CH₂Cl₂; pyridine / 2 h / Ambient temperature

With borane-THF; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1021/jo00157a034

Reference yield: 94.0%

2-(3-bromophenyl)ethanamine (58971-11-2) + 2-(Trimethylsilyl)ethyl 4-nitrophenyl carbonate (80149-80-0) → 2-(trimethylsilyl)ethyl 3-bromophenylethylcarbamate (1313605-21-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In methanol; Time;

upstream raw materials:

2-(Trimethylsilyl)ethanol

4-Nitrophenyl chloroformate

trimethylsilanyl-acetic acid ethyl ester

Downstream raw materials:

p-nitrophenyl N^α-(9-fluorenylmethyloxycarbonyl)-N^ε-<<2-(trimethylsilyl)ethoxy>carbonyl>-L-lysinate

Methyl ether of 1-(2-trimethylsilylethyloxy)carbonyl-1,2,5,6-tetrahydropyridin-3-carboxaldehyde oxime

(E,E)-N-phenylmethyl-N-(3,7,11-trimethyl-2,6,10-dodecatrienyl)-O-(2-trimethylsilyl)ethyl carbamic acid

[2-(4,5-Dimethoxy-2,3-bis-propylsulfanyl-phenyl)-ethyl]-carbamic acid 2-trimethylsilanyl-ethyl ester

Refernces

• 1、 -. "MACROCYCLIC BROAD SPECTRUM ANTIBIOTICS". Paragraph 001255. . Retrieved 2018/09/12.
• 2、 Kim, Sang Woong,Hong, Chang Yong,Lee, Koo,Lee, Eun Ju,Koh, Jong Sung. "Solid phase synthesis of benzylamine-derived sulfonamide library". . p. 735 - 738. Retrieved 2007/10/03.