Bis(4-nitrophenyl) carbonate

Base Information

• Chemical Name: Bis(4-nitrophenyl) carbonate
• CAS No.: 5070-13-3
• Molecular Formula: C13H8N2O7
• Molecular Weight: 304.216
• Hs Code.: 29209090
• European Community (EC) Number: 225-775-4
• NSC Number: 1730
• UNII: 3VR53CW8U7
• DSSTox Substance ID: DTXSID60198755
• Nikkaji Number: J126.338B
• Wikidata: Q72446594
• Mol file: 5070-13-3.mol

Synonyms:bis(4-nitrophenyl)carbonate

Chemical Property of Bis(4-nitrophenyl) carbonate

Chemical Property:

• Appearance/Colour: white to pale yellow or beige powder
• Vapor Pressure: 3.19E-09mmHg at 25°C
• Melting Point: 136-139 °C(lit.)
• Refractive Index: 1.632
• Boiling Point: 475.9 °C at 760 mmHg
• Flash Point: 217.5 °C
• PSA: 127.17000
• Density: 1.501 g/cm³
• LogP: 4.12720
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Moisture Sensitive
• Solubility.: Soluble in chloroform and tetrahydrofuran.
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 304.03315060
• Heavy Atom Count: 22
• Complexity: 377

Purity/Quality:

99% ^*data from raw suppliers

4-Nitrophenyl carbonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1[N+](=O)[O-])OC(=O)OC2=CC=C(C=C2)[N+](=O)[O-]
• Uses: Bis(4-nitrophenyl) carbonate is used as a reagent for preparation of symmetrical and unsymmetrical urea and 4-nitrophenyl esters of N-protected amino acids. It acts as a peptide coupling reagent. It finds application as a reagent for the preparation of carbamate linked cytosines.

Technology Process of Bis(4-nitrophenyl) carbonate

There total 24 articles about Bis(4-nitrophenyl) 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: 99.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + chloroform (67-66-3,8013-54-5) → bis-(p-nitrophenyl) carbonate (5070-13-3)

Guidance literature:

With oxygen; sodium hydrogencarbonate; triethylamine; In water; for 1h; Irradiation;

DOI:10.1021/ol301356r

Reference yield: 94.0%

bis(phenyl) carbonate (102-09-0) → bis-(p-nitrophenyl) carbonate (5070-13-3)

Guidance literature:

With mixed-acid; sulfuric acid; nitric acid; In cyclohexane; ethyl acetate; nitrobenzene;

Reference yield: 91.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + bis(trichloromethyl) carbonate (32315-10-9) → bis-(p-nitrophenyl) carbonate (5070-13-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; at 0 ℃; for 0.583333h; Inert atmosphere;

DOI:10.1002/anie.200907178

upstream raw materials:

bis(phenyl) carbonate

phosgene

4-nitro-phenol

4-nitrophenol sodium salt

Downstream raw materials:

2-Benzyloxycarbonylamino-propionic acid 4-nitro-phenyl ester

1,3-bis(2-methylcyclohexyl)urea

p-nitrophenyl 4-amino-4-deoxy-N¹⁰-formylpteroate

(S)-2-[(S)-2-tert-Butoxycarbonylamino-6-(2-trimethylsilanyl-ethoxycarbonylamino)-hexanoylamino]-6-(2-trimethylsilanyl-ethoxycarbonylamino)-hexanoic acid 4-nitro-phenyl ester

Refernces

• 1、 Dai, Namin,Eda, Kazuo,Harada, Hidefumi,Hashimoto, Yuka,Hosokawa, Sasuga,Kakiuchi, Toshifumi,Liang, Fengying,Okazoe, Takashi,Suzuki, Yuto,Tana, Gegen,Tsuda, Akihiko. "Photo-on-Demand Base-Catalyzed Phosgenation Reactions with Chloroform: Synthesis of Arylcarbonate and Halocarbonate Esters". . p. 9811 - 9819. Retrieved 2021/07/20.
• 2、 Moon, Hyun Kyung,Sung, Gi Hyeon,Yoon, Yong-Jin,Yoon, Hyo Jae. "Alkyl and aryl 4,5-dichloro-6-oxopyridazin-1(6 H)-carboxylates: A practical alternative to chloroformates for the synthesis of symmetric and asymmetric carbonates". supporting information. p. 1577 - 1581. Retrieved 2016/06/14.