149302-83-0

Basic information

• Product Name: 1,3-Dioxolan-2-one, 4-(4-nitrophenyl)-
• CAS NO: 149302-83-0
• Molecular Formula: C9H7NO5
• Molecular Weight: 209.158
• Mol File: 149302-83-0.mol

Chemical Properties

• CAS DataBase Reference: 1,3-Dioxolan-2-one, 4-(4-nitrophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dioxolan-2-one, 4-(4-nitrophenyl)-(149302-83-0)
• EPA Substance Registry System: 1,3-Dioxolan-2-one, 4-(4-nitrophenyl)-(149302-83-0)

Safety Data

• Hazardous Substances Data: 149302-83-0(Hazardous Substances Data)

Upstream product

• 79-37-8 oxalyl dichloride 
• 77977-75-4 p-nitrophenylethylene glycol 
• 6388-74-5 p-Nitrophenyloxirane 
• 124-38-9 carbon dioxide 
• 100-13-0 4-nitrostyrene 
• 75-44-5 phosgene 

Relevant articles and documents

Significant rate acceleration in carbonate synthesis from carbon dioxide and oxiranes using dimethyl carbonate as a recyclable medium

The synthesis of cyclic carbonates by the reaction of oxiranes and carbon dioxide in the presence of catalytic amount of tetrabutylammonium bromide in dimethylcarbonate without any metal catalyst is reported. Significant rate acceleration in the reaction

Hemisquaramide Tweezers as Organocatalysts: Synthesis of Cyclic Carbonates from Epoxides and CO2

Hemisquaramide tweezers, a new family of H-bond donor organocatalysts, are reported. The catalysts could be synthesized within two steps. Among them, H8-binaphthyl-linked hemisquaramide 7 markedly accelerated the synthesis of cyclic carbonates from epoxides and CO2. The reactions proceeded well under mild and solvent-free conditions. Kinetic resolution was also achieved at -20 °C (s = 3.0). The adjustable bite angle and orientation of the two NH groups of the catalysts are important for the high activity.

Unexpected Macrocyclic Multinuclear Zinc and Nickel Complexes that Function as Multitasking Catalysts for CO2 Fixations

Unique self-assembled macrocyclic multinuclear ZnII and NiII complexes with binaphthyl-bipyridyl ligands (L) were synthesized. X-ray analysis revealed that these complexes consisted of an outer ring (Zn3L3 or Ni3L3) and an inner core (Zn2 or Ni). In the ZnII complex, the inner Zn2 part rotated rapidly inside the outer ring in solution on an NMR timescale. These complexes exhibited dual catalytic activities for CO2 fixations: synthesis of cyclic carbonates from epoxides and CO2 and temperature-switched N-formylation/N-methylation of amines with CO2 and hydrosilane.

Synthesis of Cyclic Organic Carbonates Using Atmospheric Pressure CO2 and Charge-Containing Thiourea Catalysts

Cycloadditions of epoxides with CO2 to synthesize cyclic five-membered ring organic carbonates are of broad interest from a synthetic, environmental, and green chemistry perspective, and the development of effective catalysts for these transformations is an ongoing challenge. A series of eight charge-containing thiourea salts that catalyze these reactions under mild conditions (i.e., 60 °C and atmospheric CO2 pressure) are reported. Substrate scope and mechanistic studies were also carried out, isotope effects were measured, and a reactive intermediate was isolated revealing a surprising pathway in which a thiourea catalyst serves as a nucleophile in the cleavage of the epoxide ring.

Reaction of various oxiranes and carbon dioxide. Synthesis and aminolysis of five-membered cyclic carbonates

Various oxiranes reacted with carbon dioxide at 100 °C using lithium bromide as a catalyst under atmospheric pressure to afford the corresponding five-membered cyclic carbonates quantitatively. The rate of the reaction increased as the bulkiness of substituents on the oxirane ring was reduced or an electron-withdrawing group was introduced on the oxirane ring. The stereochemistry of the reaction of oxirane and carbon dioxide was retention without loss of optical purity. When substituted phenylethylene carbonates were reacted with benzylamine, the selectivity to afford secondary alcohol increased as the electron-withdrawing ability of the para-substituent increased.

Cyclocondensation of oxalyl chloride with 1,2-glycols

Oxalyl chloride reacts with a wide range of acyclic 1,2-glycols 1 in the presence of triethylamine to produce 1,3-dioxolan-2-ones 3 together with 1,4-dioxane-2,3-diones 2. Ethylene glycol (1d), monosubstituted ethylene glycols 1e, j-l, and erythro-1,2-disubstituted ethylene glycols 1f, m, o provide the cyclic carbonates 3 as the minor products, while the threo-compounds 1g, i, n, p, q and pinacol (1h) afford 3 as the main products. The formation of 3 may be rationalized in terms of stereoelectronically controlled cleavage of the conjugate base 17- of the tetrahedral intermediates. The rate of the conformational change of 17- into 18- and the equilibrium constant between these conformers are proposed to be the major factors affecting the reaction pattern.

Formation of cyclic carbonates in the reactions of 1,2-glycols with oxalyl chloride

Oxalyl chloride reacts with a wide range of 1,2-glycols in the presence of triethylamine to produce 1,3-dioxolan-2-ones together with 1,4-dioxane-2,3-diones; the ratio of the products largely depends on the structure of the 1,2-glycol. The formation of the cyclic carbonates may be rationalized in terms of stereoelectronically controlled cleavage of the tetrahedral intermediates.