1-(4-Chlorophenyl)-2-nitroethene

Base Information

• Chemical Name: 1-(4-Chlorophenyl)-2-nitroethene
• CAS No.: 5153-70-8
• Molecular Formula: C₈H₆ClNO₂
• Molecular Weight: 183.594
• Hs Code.: 2921490090
• European Community (EC) Number: 628-112-0,673-378-3
• NSC Number: 2547
• DSSTox Substance ID: DTXSID30879307
• Nikkaji Number: J450.246I,J87.168K
• Wikidata: Q72457262
• ChEMBL ID: CHEMBL230690
• Mol file: 5153-70-8.mol

Synonyms:706-07-0;1-(4-chlorophenyl)-2-nitroethene;(E)-1-chloro-4-(2-nitrovinyl)benzene;5153-70-8;1-chloro-4-(2-nitrovinyl)benzene;1-Chloro-4-[(E)-2-nitroethenyl]benzene;trans-4-Chloro-beta-nitrostyrene;4-Chloro-beta-nitrostyrene;Benzene, 1-chloro-4-(2-nitroethenyl)-;p-Chloro-beta-nitro-styrene;Styrene, p-chloro-beta-nitro-;Styrene, p-chloro-.beta.-nitro-;NSC 2547;p-Cloro-beta-nitrostirene;p-Cloro-beta-nitrostirene [Italian];1-Chloro-4-(2-nitro-vinyl)-benzene;BRN 2208373;p-Chloro-.beta.-nitrostyrene;4-Chloro-.beta.-nitrostyrene;CHEMBL230690;Benzene, 1-chloro-4-[(E)-2-nitroethenyl]-;1-chloro-4-(2-nitroethenyl)benzene;1-chloro-4-[(E)-2-nitrovinyl]benzene;C8H6ClNO2;3-05-00-01181 (Beilstein Handbook Reference);1-chloro-4-((E)-2-nitrovinyl)benzene;4-chloro B-nitrostyrene;MFCD00024825;NSC2547;1-((1E)-2-nitrovinyl)-4-chlorobenzene;beta-Nitro-4-chlorostyrene;4'-chloro-beta-nitrostyrene;p-Cloro-.beta.-nitrostirene;SCHEMBL219463;(E)-4-Chloro-beta-nitrostyrene;HMS561B10;DTXSID30879307;AMY13654;NSC-2547;trans-4-Chloro- beta -nitrostyrene;ANM102893;BDBM50561059;CX1346;AKOS001274725;AKOS017278253;CS-W017034;trans-4-Chloro-beta-nitrostyrene, 97%;NCGC00340559-01;AS-19347;AS-82918;1-chloro-4-((E)-2-nitro-vinyl)-benzene;LS-147213;1-Chloro-4-[(E)-2-nitroethenyl]benzene #;EN300-14355;EN300-34407;W18707;AB01122699-03;AB01122699-04;A924273;Z208331660

Chemical Property of 1-(4-Chlorophenyl)-2-nitroethene

Chemical Property:

• Melting Point: 115℃ (ligroine )
• Boiling Point: 299 °C at 760 mmHg
• Flash Point: 134.6 °C
• PSA: 45.82000
• Density: 1.324 g/cm³
• LogP: 3.11060
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 183.0087061
• Heavy Atom Count: 12
• Complexity: 180

Purity/Quality:

98% ^*data from raw suppliers

1-chloro-4-[(E)-2-nitroethenyl]benzene 95%+ ^*data from reagent suppliers

Safty Information:

• Statements: 22-43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=C[N+](=O)[O-])Cl
• Isomeric SMILES: C1=CC(=CC=C1/C=C/[N+](=O)[O-])Cl

Technology Process of 1-(4-Chlorophenyl)-2-nitroethene

There total 50 articles about 1-(4-Chlorophenyl)-2-nitroethene 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: 100.0%

nitromethane (75-52-5) + 4-chlorobenzaldehyde (104-88-1) → 1-chloro-4-(2-nitrovinyl)benzene (706-07-0,5153-70-8)

Guidance literature:

With copper(II) ferrite; In dimethyl sulfoxide; at 120 ℃; for 0.0333333h; Microwave irradiation;

DOI:10.1016/j.tetlet.2018.03.032

Reference yield: 99.9%

nitromethane (75-52-5) + 4-chlorobenzaldehyde (104-88-1) → 1-nitro-2-(4-chlorophenyl)ethylene (101671-01-6,5153-70-8)

Guidance literature:

With hydrogenchloride; N,N-dimethyl acetamide; In water; 1,2-dichloro-ethane; at 88 ℃; for 3.5h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere;

Reference yield: 97.0%

4-vinylbenzyl chloride (1073-67-2,24991-47-7) → 1-nitro-2-(4-chlorophenyl)ethylene (101671-01-6,5153-70-8)

Guidance literature:

With silver(I) nitrite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In 1,2-dichloro-ethane; at 70 ℃; for 12h; stereoselective reaction; Molecular sieve;

DOI:10.1021/ja311942e

upstream raw materials:

nitromethane

4-chlorobenzaldehyde

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

4-vinylbenzyl chloride

Downstream raw materials:

3-(4-Chlorphenyl)-N,N-dimethyl-4-nitrobutyramid

5-(4-chloro-phenyl)-3-methyl-2-thioxo-[1,3,4]thiadiazinan-6-one oxime

3-phenyl-4-nitro-5-(p-chlorophenyl)-1,2-oxazole

(4S,5S)-4-(4-Chloro-phenyl)-5-nitro-3-phenyl-4,5-dihydro-isoxazole

Refernces

• 1、 Drew, Melanie A.,Tague, Andrew J.,Richardson, Christopher,Pyne, Stephen G.,Hyland, Christopher J. T.. "Palladium-Catalyzed Formal (3 + 2) Cycloaddition Reactions of 2-Nitro-1,3-enynes with Vinylaziridines, -epoxides, and -cyclopropanes". supporting information. p. 4635 - 4639. Retrieved 2021/06/28.
• 2、 Ni, Qijian,Wang, Xuyang,Zeng, Da,Wu, Qianling,Song, Xiaoxiao. "Organocatalytic Asymmetric Synthesis of Aza-Spirooxindoles via Michael/Friedel-Crafts Cascade Reaction of 1,3-Nitroenynes and 3-Pyrrolyloxindoles". supporting information. p. 2273 - 2278. Retrieved 2021/04/05.