19771-81-4

Basic information

• Product Name: N-(2-bromophenyl)-2-furamide
• Synonyms: N-(2-bromophenyl)-2-furamide;UKRORGSYN-BB BBV-082403
• CAS NO: 19771-81-4
• Molecular Formula: C₁₁H₈BrNO₂
• Molecular Weight: 266.09
• Mol File: 19771-81-4.mol

Chemical Properties

• Melting Point: 90-91 °C
• Boiling Point: 264°C at 760 mmHg
• Flash Point: 113.4°C
• Appearance: /
• Density: 1.59g/cm³
• Vapor Pressure: 0.00998mmHg at 25°C
• Refractive Index: 1.647
• PKA: 11.97±0.70(Predicted)
• CAS DataBase Reference: N-(2-bromophenyl)-2-furamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-bromophenyl)-2-furamide(19771-81-4)
• EPA Substance Registry System: N-(2-bromophenyl)-2-furamide(19771-81-4)

Safety Data

• Hazardous Substances Data: 19771-81-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H8BrNO2/c12-8-4-1-2-5-9(8)13-11(14)10-6-3-7-15-10/h1-7H,(H,13,14)

Upstream product

• 527-69-5 2-furancarbonyl chloride 
• 615-36-1 2-bromoaniline 

Downstream Products

• 1263914-21-1 2-(furan-2-yl)-1H-1,3-benzazaphosphole 
• 1263914-23-3 N-(2-furyl)-2-phosphinoaniline 
• 1263914-02-8 2-(furan-2-carbonylamido)phenylphosphonic acid diethyl ester 
• 19771-83-6 N-(2-bromophenyl)thiofuran-2-carboxamide 
• 1569-98-8 2-(furan-2-yl)-1,3-benzothiazole 
• 20492-07-3 2-(furan-2-yl)-4H-benzo[d][1,3]oxazin-4-one 

Relevant articles and documents

Pd-Catalyzed Carbonylative Synthesis of 4H-Benzo[d][1,3]Oxazin-4-Ones Using Benzene-1,3,5-Triyl Triformate as the CO Source

A facile synthesis of 4H-benzo[d][1,3]oxazin-4-one derivatives by Pd-catalyzed carbonylative cross-coupling between N-(ortho-bromoaryl)amides and benzene-1,3,5-triyl triformate (TFBen) was developed. This procedure does not require the toxic and flammable gas CO as the carbonyl source and tolerates a wide scope of functional groups. Remarkably, 4H-benzo[d][1,3]oxazin-4-ones incorporated to natural products and drugs can be constructed by this method.

Photocatalyst- And Transition-Metal-Free Visible-Light-Promoted Intramolecular C(sp2)-S Formation

A photocatalyst- and transition-metal-free visible-light-induced cyclization of ortho-halothiobenzanilides has been developed. Upon irradiation with visible light, substrates undergo dehalogenative cyclization to 2-aryl benzothiazoles with high efficiency and selectivity. This photocyclization exhibits a high tolerance to various functional groups, is applicable for the synthesis of 2-alkyl benzothiazoles, and is easy to set up for gram-scale reaction.

Direct Alkoxycarbonylation of Heteroarenes via Cu-Mediated Trichloromethylation and in Situ Alcoholysis

We report an efficient approach for direct alkoxycarbonylation of furans as well as other heteroarenes via a one-step copper-mediated reaction of three components (i.e., heteroarene, alcohol, and CHCl3). The copper additive was confirmed to simultaneously promote the reaction in three pathways: oxidant cracking, single electron transfer, and alcoholysis. By means of this protocol, various functionalized furancarboxylates and other heteroarenecarboxylates were facilely obtained in moderate to good yields.

Iron-Catalyzed Oxidative Decarbonylative α-Alkylation of Acyl-Substituted Furans with Aliphatic Aldehydes as the Alkylating Agents

A protocol for FeCl2-catalyzed oxidative decarbonylative α-alkylation of acyl furans using alkyl aldehydes as the alkylating agents has been developed. This protocol affords α-alkyl-α-acylfurans in moderate to good yields in a practical and sustainable fa

Palladium-catalyzed carbonylative synthesis of benzoxazinones from N -(o -bromoaryl)amides using paraformaldehyde as the carbonyl source

Carbonylation reactions have been widely used in organic synthesis. However, the manipulation of toxic and pressurized carbon monoxide limited their applications in organic laboratories. The search for alternative carbonyl sources as an important method for carbonylative organic synthesis is spreading. Herein, a series of substituted benzoxazinones were synthesized from N-(o-bromoaryl)amides by palladium-catalyzed carbonylation with paraformaldehyde as the carbonyl source, which is inexpensive, stable, and easy to use. Notably, this is the first example of using paraformaldehyde as the CO source in palladium-catalyzed carbonylative synthesis of heterocycles.

PC-N-Heterocycles: Synthesis of biaryl-type 1,3-benzazaphospholes with ortho-substituted phenyl or 2-heteroaryl groups

A facile synthesis of functionally substituted 2-(hetero)aryl 1,3-benzazaphospholes via nickel- or palladium-catalyzed phosphonylation of N-acyl-2-bromoanilides 1a-k with triethyl phosphite is presented. Anilidophosphonates 2a-g with naphthoyl-, o-substituted phenyl, furoyl- or thenoyl groups allow direct reductive cyclization with LiAlH4 to benzazaphospholes 3. The reaction of the o-bromoderivative 2d proceeds with concomitant replacement of bromine by hydrogen, whereas the electron-withdrawing pyridyl group of 2h prevents the synthesis of 3h by this short route. An alternative synthesis of 2-pyridylbenzazaphosphole 3hvia anilidophosphonates succeeded starting from Fmoc-anilinophosphonate 2kvia selective cleavage of the N-protecting group, reduction of the resulting phosphonoaniline to phosphinoaniline and cyclization with pyridine-2-carboxaldehyde via a dihydrobenzazaphosphole 8. N-Substituted pyridylmethylbenzazaphosphole 9 was detected as a side product. The structure elucidation of the new compounds is based on multinuclear NMR data and X-ray crystal structure analyses of a phosphonoanilide, underlining the dominance of N-H...OP hydrogen bonds over N-H...OC type hydrogen bonds, of 3h and a supramolecular associate of 3b and its unprecedented air oxidation product 10.