1-Fluoro-4-(2-nitrovinyl)benzene

Base Information

• Chemical Name: 1-Fluoro-4-(2-nitrovinyl)benzene
• CAS No.: 5153-69-5
• Molecular Formula: C₈H₆FNO₂
• Molecular Weight: 167.14
• European Community (EC) Number: 211-891-2,637-102-5
• NSC Number: 121154
• DSSTox Substance ID: DTXSID001281213
• Nikkaji Number: J49.495J,J61.357F
• Wikidata: Q76305984
• ChEMBL ID: CHEMBL231217
• Mol file: 5153-69-5.mol

Synonyms:1-fluoro-4-(2-nitrovinyl)benzene;706-08-1;5153-69-5;(E)-1-fluoro-4-(2-nitrovinyl)benzene;4-Fluoro-beta-nitrostyrene;trans-4-fluoro-beta-nitrostyrene;1-fluoro-4-[(E)-2-nitroethenyl]benzene;trans-p-Fluoro-beta-nitrostyrene;4-Fluoro-|A-nitrostyrene;p-Fluoro-beta-nitrostyrene;Styrene, p-fluoro-beta-nitro-;1-fluoro-4-[(E)-2-nitrovinyl]benzene;Benzene, 1-fluoro-4-(2-nitroethenyl)-;EINECS 211-891-2;NSC 121154;AI3-29632;CHEMBL231217;trans p-Fluorophenyl-1 nitro-2 ethylene [French];Styrene, p-fluoro-beta-nitro-, (E)-;trans p-Fluorophenyl-1 nitro-2 ethylene;Benzene, 4-fluoro-1-(2-nitroethenyl)-;1-fluoro-4-[(1E)-2-nitroethenyl]benzene;C8-H6-F-N-O2;1-(4-Fluorophenyl)-2-nitroethylene;MFCD00024824;NSC121154;Bio7F6;4-Fluoro-ss-nitrostyrene;Benzene, 1-fluoro-4-[(1E)-2-nitroethenyl]-;p-Fluoro-.beta.-nitrostyrene;4-Fluoro- beta -nitrostyrene;SCHEMBL102629;SCHEMBL102630;(E)-4-Fluoro-beta-nitrostyrene;4-fluoro-trans-beta-nitrostyrene;Styrene, p-fluoro-.beta.-nitro-;VRFSQVFSQAYHRU-AATRIKPKSA-N;DTXSID001281213;AMY13658;ANM100002;BDBM50561058;AKOS002968710;AKOS017269588;AKOS025310220;NSC-121154;AS-60911;trans-1-(4-fluorophenyl)-2-nitro-ethene;(E)-1-fluoro-4-(2-nitro-vinyl)-benzene;1-fluoro-4-((E)-2-nitro-vinyl)-benzene;4-Fluoro-beta-nitrostyrene(sum of isomers);LS-147220;LS-147221;CS-0031463;Benzene, 1-fluoro-4-[(E)-2-nitroethenyl]-;EN300-724958;Benzene, 4-fluoro-1-(2-nitroethenyl)- (9CI);A836933;A924272;4-Fluoro-beta-nitrostyrene, >=98.5% (sum of isomers, GC);InChI=1/C8H6FNO2/c9-8-3-1-7(2-4-8)5-6-10(11)12/h1-6H/b6-5

Chemical Property of 1-Fluoro-4-(2-nitrovinyl)benzene

Chemical Property:

• Vapor Pressure: 0.0274mmHg at 25°C
• Boiling Point: 254.5°Cat760mmHg
• Flash Point: 107.7°C
• PSA: 45.82000
• Density: 1.276g/cm³
• LogP: 2.59630
• Storage Temp.: 2-8°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 167.03825660
• Heavy Atom Count: 12
• Complexity: 180

Purity/Quality:

99% ^*data from raw suppliers

(E)-1-Fluoro-4-(2-nitrovinyl)benzene 95+% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=C[N+](=O)[O-])F
• Isomeric SMILES: C1=CC(=CC=C1/C=C/[N+](=O)[O-])F
• Uses: (E)-β-Nitro-4-fluorostyrene is used in enantioselective Synthesis of Cyclohexenol derivatives .

Technology Process of 1-Fluoro-4-(2-nitrovinyl)benzene

There total 24 articles about 1-Fluoro-4-(2-nitrovinyl)benzene 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: 92.0%

(E)-4-fluorocinnamic acid (459-32-5) → trans-1-(4-fluorophenyl)-2-nitro-ethene (706-08-1,5153-69-5)

Guidance literature:

With chloro-trimethyl-silane; copper(II) nitrate trihydrate; In acetonitrile; at 100 ℃; for 2h; stereoselective reaction;

DOI:10.1016/j.tetlet.2017.06.017

Reference yield: 90.0%

para-fluorostyrene (405-99-2) → 4-fluoro-β-nitrostyrene (5153-69-5,706-08-1)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; silver nitrate; In 1,2-dichloro-ethane; at 70 ℃; for 12h; Molecular sieve; Inert atmosphere;

DOI:10.1039/d1ob00714a

Reference yield: 84.0%

nitromethane (75-52-5) + para-fluorobenzylamine (140-75-0) → 4-fluoro-β-nitrostyrene (5153-69-5,706-08-1)

Guidance literature:

With 4-(4-fluorophenyl)naphthalene-1,2-dione; oxygen; at 80 ℃; for 12h;

DOI:10.1021/acscatal.9b03442

upstream raw materials:

nitromethane

4-fluorobenzaldehyde

Butyl-[1-(4-fluoro-phenyl)-2-nitro-ethyl]-amine

4-fluorobenzalaniline

Downstream raw materials:

dimethyl <1-(p-fluorophenyl)vinyl>phosphonate

N,N-bis<3-(4-fluorophenyl)-4-(methoxycarbonyl)-5-methyl-2,3-dihydrofuran-2-yl>hydroxylamine

Butyl-[1-(4-fluoro-phenyl)-2-nitro-ethyl]-amine

2-(4-fluorophenyl)-1H-benzoimidazole

Refernces

• 1、 Dill, Maximilian,Grau, Benedikt W.,Hampel, Frank,Jux, Norbert,Kahnt, Axel,Tsogoeva, Svetlana B.. "Four-Step Domino Reaction Enables Fully Controlled Non-Statistical Synthesis of Hexaarylbenzene with Six Different Aryl Groups**". supporting information. p. 22307 - 22314. Retrieved 2021/08/25.
• 2、 Pal, Mrityunjoy,Musib, Dulal,Pal, Maynak,Rana, Gopal,Bag, Gobinda,Dutta, Subrata,Roy, Mithun. "A noncovalent hybrid of [Pd(phen)(OAc)2] and st-DNA for the enantioselective hydroamination of β-nitrostyrene with methoxyamine". supporting information. p. 5072 - 5076. Retrieved 2021/06/21.