4701-10-4

Basic information

• Product Name: 1-nitro-4-phenylbutadiene
• Synonyms: 1-nitro-4-phenylbutadiene
• CAS NO: 4701-10-4
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18
• Mol File: 4701-10-4.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 315.8°Cat760mmHg
• Flash Point: 150.6°C
• Appearance: /
• Density: 1.142g/cm³
• Vapor Pressure: 0.000791mmHg at 25°C
• Refractive Index: 1.605
• CAS DataBase Reference: 1-nitro-4-phenylbutadiene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-nitro-4-phenylbutadiene(4701-10-4)
• EPA Substance Registry System: 1-nitro-4-phenylbutadiene(4701-10-4)

Safety Data

• Hazardous Substances Data: 4701-10-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H9NO2/c12-11(13)9-5-4-8-10-6-2-1-3-7-10/h1-9H/b8-4+,9-5+

Upstream product

• 75-52-5 nitromethane 
• 104-55-2 3-phenyl-propenal 
• 28010-12-0 5-phenylpenta-2,4-dienoic acid 
• 14371-10-9 (E)-3-phenylpropenal 
• 16939-57-4 (E)-buta-1,3-dienylbenzene 
• 108030-46-2 (E,E)-1-(N,N-dimethylamino)-4-nitro-1,3-butadiene 
• 100-58-3 phenylmagnesium bromide 
• 1515-78-2 buta-1,3-dien-1-ylbenzene 
• 1849-29-2 1,1,1-trideuteromethanol 

Downstream Products

• 1171036-86-4 (S)-2-[(S,E)-1-(nitromethyl)-3-phenylprop-2-enyl]cyclohexanone 
• 1065514-96-6 (2R,3R,E)-2-allyl-3-(nitromethyl)-5-phenylpent-4-enal 
• 1241890-44-7 (2R,3R,E)-2-methyl-3-(nitromethyl)-2,5-diphenylpent-4-enal 
• 1065514-92-2 (2R,3R,E)-2-methyl-3-(nitromethyl)-5-phenylpent-4-enal 
• 1065514-94-4 (2R,3R,E)-3-(nitromethyl)-5-phenyl-2-propylpent-4-enal 
• 1241890-59-4 (3R,4R,E)-3-hydroxy-4-(nitromethyl)-6-phenylhex-5-en-2-one 
• 1242146-24-2 (R)-(E)-4-(nitromethyl)-6-phenyl-5-hexen-2-one 
• 1065514-90-0 (2R,3R,E)-2-isopropyl-3-(nitromethyl)-5-phenylpent-4-enal 
• 1228821-13-3 C₂₀H₂₇NO₃ 
• 1228821-10-0 (S)-2-[(S,E)-1-nitro-4-phenylbut-3-en-2-yl]cyclopentanone 

Relevant articles and documents

Palladium-Catalyzed Aminomethylation of Nitrodienes and Dienones via Double C—N Bond Activation

A new strategy for the generation of the active Pd-alkyl species from aminal via C—N bond activation has been established, in which the formation of zwitterionic intermediate through aza-Michael addition of aminal to nitrodienes or dienones is identified as a key step for the activation of the C—N bond. The efficient strategy has enabled a new palladium-catalyzed α-aminomethylation of nitrodienes and dienones via double C—N bond activation. The scope and versatility of the reaction were demonstrated and a broad range of substrates bearing electron-donating and -withdrawing groups on the aromatic rings were all compatible with this reaction to furnish the desired α-aminomethylated products in moderate to good yields with excellent regioselectivities and E/Z selectivities.

Geometrically Selective Denitrative Trifluoromethylthiolation of β-Nitrostyrenes with AgSCF3for (E)-Vinyl Trifluoromethyl Thioethers

An efficient copper(II)-promoted denitrative trifluoromethylthiolation under mild reaction conditions has been developed for vinyl trifluoromethyl thioethers to construct Cvinyl-SCF3 bonds with stable AgSCF3 as a source of the trifluoromethylthio. This reaction system tolerates a broad range of functional groups to commendably achieve a high product yield and excellent stereoselectivity of E/Z.

Dealkenylative Alkenylation: Formal σ-Bond Metathesis of Olefins

The dealkenylative alkenylation of alkene C(sp3)?C(sp2) bonds has been an unexplored area for C?C bond formation. Herein 64 examples of β-alkylated styrene derivatives, synthesized through the reactions of readily accessible feedstock olefins with β-nitrostyrenes by ozone/FeII-mediated radical substitutions, are reported. These reactions proceed with good efficiencies and high stereoselectivities under mild reaction conditions and tolerate an array of functional groups. Also demonstrated is the applicability of the strategy through several synthetic transformations of the products, as well as the syntheses of the natural product iso-moracin and the drug (E)-metanicotine.