trans-4-Bromo-beta-nitrostyrene

Base Information

• Chemical Name: trans-4-Bromo-beta-nitrostyrene
• CAS No.: 5153-71-9
• Molecular Formula: C₈H₆BrNO₂
• Molecular Weight: 228.045
• European Community (EC) Number: 628-050-4
• NSC Number: 121158
• DSSTox Substance ID: DTXSID101308701
• Nikkaji Number: J450.249C,J464.858G
• ChEMBL ID: CHEMBL230582
• Mol file: 5153-71-9.mol

Synonyms:5153-71-9;trans-4-Bromo-beta-nitrostyrene;(E)-1-bromo-4-(2-nitrovinyl)benzene;1-Bromo-4-(2-nitrovinyl)benzene;1-Bromo-4-[(E)-2-nitroethenyl]benzene;3156-37-4;Benzene, 1-bromo-4-[(1E)-2-nitroethenyl]-;trans-1-bromo-4-(2-nitrovinyl)benzene;Benzene, 1-bromo-4-(2-nitroethenyl)-;MFCD00191856;1-bromo-4-[(E)-2-nitrovinyl]benzene;NSC121158;beta-Nitro-4-bromostyrene;4-Bromo-.beta.-nitrostyrene;trans-4-Bromo-A-nitrostyrene;SCHEMBL421633;SCHEMBL421634;CHEMBL230582;(E)-4-Bromo-beta-nitrostyrene;1-(4-Bromophenyl)-2-nitroethene;DTXSID101308701;trans-4-Bromo- beta -nitrostyrene;AMY15450;ANM102849;AKOS003241046;CS-W016767;NSC-121158;trans-4-Bromo-beta-nitrostyrene, 99%;AS-59508;1-Bromo-4-((E)-2-nitro-vinyl)-benzene;1-bromo-4-[(1E)-2-nitroethenyl]benzene;1-bromo-4-[(trans)-2-nitrovinyl]benzene;1-Bromo-4-[(E)-2-nitroethenyl]benzene #;Benzene, 1-bromo-4-[(E)-2-nitroethenyl]-;EN300-55528;EN300-314814

Chemical Property of trans-4-Bromo-beta-nitrostyrene

Chemical Property:

• Vapor Pressure: 0.000654mmHg at 25°C
• Melting Point: 148-150 °C(lit.)
• Refractive Index: 1.636
• Boiling Point: 318.9 °C at 760 mmHg
• Flash Point: 146.7 °C
• PSA: 45.82000
• Density: 1.596 g/cm³
• LogP: 3.21970
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 226.95819
• Heavy Atom Count: 12
• Complexity: 180

Purity/Quality:

98%,99%, ^*data from raw suppliers

trans-4-Bromo-β-nitrostyrene 99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=C[N+](=O)[O-])Br
• Isomeric SMILES: C1=CC(=CC=C1/C=C/[N+](=O)[O-])Br
• Uses: trans-4-Bromo-β-nitrostyrene may be employed as Michael acceptor for the organocatalytic asymmetric Michael addition of protected 3-hydroxypropanal to β-nitrostyrenes.

Technology Process of trans-4-Bromo-beta-nitrostyrene

There total 16 articles about trans-4-Bromo-beta-nitrostyrene 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: 98.0%

→ (E)-1-bromo-4-(2-nitrovinyl)benzene (3156-37-4,5153-71-9)

Guidance literature:

With chloro-trimethyl-silane; copper(ll) sulfate pentahydrate; guanidine nitrate; In acetonitrile; at 0 - 20 ℃; Inert atmosphere;

With triethylamine; In acetonitrile; at 20 ℃; for 0.416667h; stereoselective reaction; Inert atmosphere;

Reference yield: 96.0%

trans-4-bromocinnamic acid (1200-07-3,5676-63-1,17916-60-8) → (E)-1-bromo-4-(2-nitrovinyl)benzene (3156-37-4,5153-71-9)

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: 95.0%

1-bromo-4-ethenyl-benzene (2039-82-9) → (E)-1-bromo-4-(2-nitrovinyl)benzene (3156-37-4,5153-71-9)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; dipotassium peroxodisulfate; sodium nitrite; In 1,2-dichloro-ethane; at 100 ℃; for 24h; stereoselective reaction; Sealed tube;

DOI:10.1016/j.tetlet.2015.11.064

upstream raw materials:

1-bromo-4-ethenyl-benzene

nitromethane

4-bromo-benzaldehyde

3-(4-bromophenyl)acrylic acid

Downstream raw materials:

(S)-3-(4-bromophenyl)-4-nitrobutanal

(2R,3S)-3-(4-bromophenyl)-2-methyl-4-nitrobutanal

nitromethane

1-bromo-4-(2-nitroethyl)benzene