4-Nitrophenyl chloroformate

Base Information

• Chemical Name: 4-Nitrophenyl chloroformate
• CAS No.: 7693-46-1
• Deprecated CAS: 1269758-59-9,1945216-83-0,2490349-81-8
• Molecular Formula: C7H4ClNO4
• Molecular Weight: 201.566
• Hs Code.: 2915.13. DERIVATION
• European Community (EC) Number: 231-706-9
• DSSTox Substance ID: DTXSID3064772
• Nikkaji Number: J249F
• Wikidata: Q69757750
• Mol file: 7693-46-1.mol

Synonyms:4-Nitrophenyl chloroformate;7693-46-1;4-Nitrophenyl carbonochloridate;Chloroformic acid 4-nitrophenyl ester;Carbonochloridic acid, 4-nitrophenyl ester;p-Nitrophenyl chloroformate;(4-nitrophenyl) carbonochloridate;Chloroformic acid p-nitrophenyl ester;MFCD00007321;Formic acid, chloro-, p-nitrophenyl ester;EINECS 231-706-9;AI3-52204;(4-nitrophenyl) chloroformate;p-nitrophenylchloroformate;4-nitrophenyl choroformate;4-nitrophenol chloroformate;4-nitrophenyl chioroformate;p-nitro-phenyl chloroformate;(4-nitrophenyl)chloroformate;4-nitro-phenyl chloroformate;p-Nitrophenyl chlorocarbonate;4-nitrophenyl chlorocarbonate;p-nitrophenoxycarbonylchloride;SCHEMBL15168;para-nitrophenyl chloroformate;4-(nitro)phenyl chloroformate;4-nitrophenoxycarbonyl chloride;p-Nitrophenoxycarbonyl chloride;para-nitro-phenyl chloroformate;4-Nitrophenyl chloridocarbonate;Chloroformic acid 4-nitrophenyl;4-nitro-phenyl carbonochloridate;4-nitrophenyl carbono-chloridate;DTXSID3064772;SCHEMBL14520259;4-Nitrophenylchloroformate (Npc);(4-nitrophenyl)chloranuidylformate;4-Nitrophenyl chloridocarbonate #;4-Nitrophenyl chloroformate, 96%;STR07035;AKOS000121090;AKOS024438096;AC-5115;CS-W018340;4-Nitrophenyl Chloroformate >90per cent;BP-20362;FT-0600008;EN300-24207;A838902;Q-101208;4-Nitrophenyl chloroformate, purum, >=97.0% (AT);F0001-1970

Chemical Property of 4-Nitrophenyl chloroformate

Chemical Property:

• Appearance/Colour: cream solid
• Vapor Pressure: 0.00312mmHg at 25°C
• Melting Point: 77-79 °C(lit.)
• Refractive Index: 1.577
• Boiling Point: 283.7 °C at 760 mmHg
• Flash Point: 125.3 °C
• PSA: 72.12000
• Density: 1.506 g/cm³
• LogP: 2.85560
• Storage Temp.: 2-8°C
• Sensitive.: Lachrymatory
• Solubility.: Soluble in acetone, chloroform, acetone, toluene and benzene.
• Water Solubility.: decomposes
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 200.9828853
• Heavy Atom Count: 13
• Complexity: 207

Purity/Quality:

99% ^*data from raw suppliers

4-NitrophenylChloroformate>90% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xi,T,F
• Hazard Codes: C,T,Xi,F
• Statements: 34-36/37-23/24/25-41-36/37/38-11-67-36
• Safety Statements: 26-36/37/39-45-38-28A-36-16-27

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Acid Halides
• Canonical SMILES: C1=CC(=CC=C1[N+](=O)[O-])OC(=O)Cl
• Uses: 4-Nitrophenyl Chloroformate is an ester of chloroformic acid used in the immobilization of enzymes and other biomolecules. 4-Nitrophenyl chloroformate is used in the synthesis of poly(oxyethylene) modified dextrans. It is also used to prepare a cleavable, heterobifunctional cross-linker for reversible conjugation of amines to thiol-modified DNA. Further, it is used in the synthesis of mixed, activated carbonates, thiocarbonates and activated urethanes. In addition to this, it is used in the preparation of 4-nitrophenyl diazoacetate with diazomethane. 4-Nitrophenyl chloroformate can be used:As a reagent for the activation of amines, alcohols and thiols.In the synthesis of 4-substituted phenyl derivatives of 1,2,4-triazolidindiones (urazoles).In the solid-phase synthesis of 3-aryl-2,4-quinazolinedione derivatives with potent anti-cancer property.In the preparation of poly(oxyethylene) modified dextrans.To synthesize a cleavable, heterobifunctional cross-linker for reversible conjugation of amines to thiol-modified DNA.

Technology Process of 4-Nitrophenyl chloroformate

There total 10 articles about 4-Nitrophenyl chloroformate 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: 95.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + bis(trichloromethyl) carbonate (32315-10-9) → 4-Nitrophenyl chloroformate (7693-46-1)

Guidance literature:

With N,N-diethylaniline; In toluene; at 0 ℃; for 1h;

DOI:10.1007/s11696-020-01402-z

Reference yield: 92.0%

phosgene (75-44-5) + 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) → 4-Nitrophenyl chloroformate (7693-46-1)

Guidance literature:

With potassium carbonate; In dichloromethane; at 25 ℃; Green chemistry;

DOI:10.1080/00397911.2012.709300

Reference yield: 90.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + trichloromethyl chloroformate (503-38-8) → 4-Nitrophenyl chloroformate (7693-46-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; 1.) 0 deg C, 0.5 h, 2.) reflux, 2 h;

DOI:10.1055/s-1993-25809

upstream raw materials:

phosgene

4-nitro-phenol

4-nitrophenol sodium salt

trichloromethyl chloroformate

Downstream raw materials:

carbamic acid-(1-chloroethynyl-cyclohexyl ester)

carbonic acid-(5-acetyl-[8]quinolyl ester)-(4-nitro-phenyl ester)

tert-Butyl 4-nitrophenyl carbonate

4-nitrophenyl 1H-indole-1-carboxylate

Refernces

• 1、 Sedlak, Milos,Pejchal, Vladimir,Imramovsky, Ales,Hanusek, Jiri. "A safe and efficient route for the preparation of nitro-, dinitro-, and trinitrophenyl chloroformates". supporting information. p. 2365 - 2369. Retrieved 2013/07/26.
• 2、 Austeri, Martina,Linder, David,Lacour, Jerome. "(Cyclopentadienyl)ruthenium-catalyzed regio- and enantioselective decarboxylative allylic etherification of allyl aryl and alkyl carbonates". experimental part. p. 3339 - 3347. Retrieved 2011/02/23.