4-nitrophenyl formate

• ChemBase ID: 157819
• Molecular Formular: C7H5NO4
• Molecular Mass: 167.1189
• Monoisotopic Mass: 167.02185765
• SMILES: c1cc(ccc1[N+](=O)[O-])OC=O
• Canonical SMILES: O=COc1ccc(cc1)[N+](=O)[O-]
• InChI: InChI=1S/C7H5NO4/c9-5-12-7-3-1-6(2-4-7)8(10)11/h1-5H
• InChIKey: IEXRKQFZXJSHOB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-nitrophenyl formate
• IUPAC Traditional name: 4-nitrophenyl formate
• Synonyms: Formic acid 4-nitrophenyl ester; 4-Nitrophenyl formate; SC 154301; p-Nitrophenyl Formate; 甲酸对硝基苯酯; 4-硝基苯基甲酸酯; 4-硝基苯酚甲酯

Database IDs

• CAS Number: 1865-01-6
• EC Number: 217-473-6
• MDL Number: MFCD00014713
• Beilstein Number: 1950897
• PubChem SID: 162251956; 24845931
• PubChem CID: 74628

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.4717922
• LogD (pH = 7.4): 1.4717922
• Log P: 1.4717922
• Molar Refractivity: 39.0204 cm^3
• Polarizability: 14.892089 Å^3
• Polar Surface Area: 69.44 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Apperance: Off-White Solid
• Melting Point: 70-74°C; 71-74 °C; 72-74°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Moisture & Light Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥97.0% (HPLC); 98%
• Empirical Formula (Hill Notation): C7H5NO4

DETAILS

Sigma Aldrich - 06554

Other Notes
Selective formylation of terminal amino groups in lysine and ornithine1; Formylation of α-amino groups in peptides2

Toronto Research Chemicals - N503500

A selective formylating agent for one of two amino groups in such basic amino acids as ornithine or lysine.

REFERENCES

• Schiller, P., et al.: J. Med. Chem., 43, 551 (2000)
• Schreiner, E., et al.: Bioorg. Med. Chem. Lett., 14, 4999 (2000)
• Convenient and selective reagent for the formylation of amino groups: Bull. Chem. Soc. Jpn., 36, 754 (1963); Synthesis, 979 (1982); Synth. Commun., 29, 1819 (1999).