4-nitrophenyl chloroformate

• ChemBase ID: 75326
• Molecular Formular: C7H4ClNO4
• Molecular Mass: 201.56396
• Monoisotopic Mass: 200.98288529
• SMILES: [N+](=O)(c1ccc(cc1)OC(=O)Cl)[O-]
• Canonical SMILES: ClC(=O)Oc1ccc(cc1)[N+](=O)[O-]
• InChI: InChI=1S/C7H4ClNO4/c8-7(10)13-6-3-1-5(2-4-6)9(11)12/h1-4H
• InChIKey: NXLNNXIXOYSCMB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-nitrophenyl chloroformate
• IUPAC Traditional name: 4-nitrophenyl chloroformate
• Synonyms: 4-Nitrophenyl carbonochloridoate; 4-[(Chlorocarbonyl)oxy]nitrobenzene; 4-Nitrophenyl chloroformate; 4-Nitrophenyl chloroformate; p-Nitrophenyl chloroformate-activated Agarose; P-NITROPHENYL CHLOROFORMATE; 4-Nitrophenyl carbonochloridate; Chloroformic acid p-nitrophenyl ester; Chloroformic acid 4-nitrophenyl ester; 4-Nitrophenyl chloroformate; p-NITROPHENYLCHLORO-FORMATE; 氯甲酸-4-硝基苯酯; 氯甲酸对硝基苯酯; 对硝基苯基氯甲酸酯

Database IDs

• CAS Number: 7693-46-1
• EC Number: 231-706-9
• MDL Number: MFCD00007321
• Beilstein Number: 518127
• PubChem SID: 24853895; 162040244; 24849861
• PubChem CID: 82129

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.5272176
• LogD (pH = 7.4): 2.5272176
• Log P: 2.5272176
• Molar Refractivity: 44.2239 cm^3
• Polarizability: 16.865992 Å^3
• Polar Surface Area: 69.44 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 75-82°C; 76-82 °C; 77-79 °C(lit.); 77-79°C
• Boiling Point: 159-162 °C/19 mmHg(lit.); 159-162°C @ 19 mm; 159-162°C/19mm; 159-162°C/19mm
• Flash Point: >110°C(230°F)

Safety Information

• Storage Condition: 2-8°C, Desiccate
• Storage Warning: Corrosive/Harmful/Moisture Sensitive/Keep Cold/Store under Argon; Moisture Sensitive
• European Hazard Symbols: Corrosive (C); X; Irritant (Xi)
• UN Number: 1219; 1759; 3261; UN3261
• German water hazard class: 3
• Hazard Class: 3; 8
• Packing Group: 2; II
• Australian Hazchem: 2X
• Risk Statements: 20/22-34; 34-36/37; 36-67; R:34
• Safety Statements: 26; 26-36/37/39-45; S:26-27/28-36/37/39-46-64
• EU Classification: C10
• EU Hazard Identification Number: 8B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06; GHS07
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H301-H332-H314-H318; H314-H335; H319-H336
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A; P261-P280-P305 + P351 + P338-P310; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1219 3/PG 2; UN 3261 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ~97%; ≥97.0% (AT); 95+%; 96%; 97%
• Grade: purum
• Extent of Labeling: 10-30 μmol per mL; 10-40 μmol per mL; 25-50 μmol per mL
• Matrix: 4% beaded agarose; 6% agarose macrobeads, diameter 200-300 μm; Cross-linked 4% beaded agarose
• Matrix Active Group: p-nitrophenyl carbonate
• Matrix Spacer: 1 atom (when ligands are coupled to the carbonyl groups by displacement of p-nitrophenol)
• Linear Formula: ClCO2C6H4NO2

DETAILS

MP Biomedicals - 05202175

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02151761

Crystalline
Purity: ~97%
Amine N-protecting reagent; also used for blocking hydroxyl groups in nucleotides.

Sigma Aldrich - 23240

Other Notes
Reagent for the synthesis of mixed, activated carbonates and thiocarbonates, activated urethanes, and other compounds1

Sigma Aldrich - 160210

Application
Employed in the preparation of poly(oxyethylene) modified dextrans.1
Used to synthesize a cleavable, heterobifunctional cross-linker for reversible conjugation of amines to thiol-modified DNA.
Packaging
5, 25, 100 g in glass bottle

REFERENCES

• Letsinger, R.L., and Ogilvie, K.K., J. Org. Chem., 32: 296 (1967).
• Reagent for protection of nucleoside alcohols. The carbonate derivatives readily undergo aqueous hydrolysis in the presence of imidazole: J. Org. Chem., 33, 3699 (1967). For use in the formation of a carbonate linker in an efficient N-terminal attachment methodology for solid phase peptide synthesis, see: Synlett, 1609 (2000).