35082-00-9

Basic information

• Product Name: N-butyl-N-phenylformamide
• Synonyms: Formamide, N-butyl-N-phenyl-; Formanilide, N-butyl-
• CAS NO: 35082-00-9
• Molecular Formula: C₁₁H₁₅NO
• Molecular Weight: 177.2429
• Mol File: 35082-00-9.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 291.2°C at 760 mmHg
• Flash Point: 127.1°C
• Density: 1.017g/cm³
• Vapor Pressure: 0.00198mmHg at 25°C
• Refractive Index: 1.539
• CAS DataBase Reference: N-butyl-N-phenylformamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-butyl-N-phenylformamide(35082-00-9)
• EPA Substance Registry System: N-butyl-N-phenylformamide(35082-00-9)

Safety Data

• Hazardous Substances Data: 35082-00-9(Hazardous Substances Data)

Upstream product

• 64-18-6 formic acid 
• 1126-78-9 N-(n-butyl)aniline 
• 109-65-9 1-bromo-butane 
• 6780-49-0 ethyl N-phenylformimidate 
• 71-43-2 benzene 
• 124-38-9 carbon dioxide 
• 109-94-4 formic acid ethyl ester 
• 667-27-6 Ethyl bromodifluoroacetate 
• 613-29-6 N-Dibutylaniline 
• 1077-18-5 N-benzylidenebutan-1-amine 

Relevant articles and documents

Catalyst-free photoinduced selective oxidative C(sp3)-C(sp3) bond cleavage in arylamines

Due to the directional nature of sp3-hybridized orbitals and the absence of π-orbitals, the oxidative cleavage of the kinetically and thermodynamically stable C(sp3)-C(sp3) bond is extremely difficult and remains scarcely explored. In this work, under the double argument of quantum mechanics (QM) computations and meticulous experiments on our well-designed C-C single bond cleavage mechanism, we discovered a means of photoinduced selective oxidative C(sp3)-C(sp3) bond cleavage in arylamines, easily achieved by simple visible light irradiation using O2as a benign oxidant under very mild conditions. The utility of our methodology was demonstrated by the C(sp3)-C(sp3) bond cleavage in morpholine/piperazine arylamines with excellent functional group tolerance. Importantly, our methodology is noteworthy, not only in that it does not require any catalysts, but also in that it provides valuable possibilities for the scalable functionalization of clinical drugs and natural products.

Direct Synthesis of N,N-Disubstituted Formamides by Oxidation of Imines Using an HFIP/UHP System

The straightforward synthesis of N,N-disubstituted formamides using a combination of 1,1,1,3,3,3-hexafluoroispropanol (HFIP) and H2O2 is described. The unique features of HFIP allowed the utilization of a green oxidant such as H2O2, and the products, arising from an oxidation-rearrangement sequence, were obtained in good to high yields under smooth reaction conditions.

Tetracoordinate borates as catalysts for reductive formylation of amines with carbon dioxide

We report sodium trihydroxyaryl borates as the first robust tetracoordinate organoboron catalysts for reductive functionalization of CO2. These catalysts, easily synthesized from condensing boronic acids with metal hydroxides, activate main group element-hydrogen (E-H) bonds efficiently. In contrast to BX3 type boranes, boronic acids and metal-BAr4 salts, under transition metal-free conditions, sodium trihydroxyaryl borates exhibit high reactivity of reductive N-formylation toward a variety of amines (106 examples), including those with functional groups such as ester, olefin, hydroxyl, cyano, nitro, halogen, MeS-, ether groups, etc. The over-performance to catalyze formylation of challenging pyridyl amines affords a promising alternative method to the use of traditional formylation reagents. Mechanistic investigation supports electrostatic interactions as the key for Si/B-H activation, enabling alkali metal borates as versatile catalysts for hydroborylation, hydrosilylation, and reductive formylation/methylation of CO2.