Cinnamyl bromide

Base Information

• Chemical Name: Cinnamyl bromide
• CAS No.: 4392-24-9
• Molecular Formula: C9H9Br
• Molecular Weight: 197.074
• Hs Code.: 29039990
• European Community (EC) Number: 224-511-5
• NSC Number: 78446
• Nikkaji Number: J478.801J,J205.770K
• Wikidata: Q76305006
• Mol file: 4392-24-9.mol

Synonyms:Cinnamyl bromide;4392-24-9;(3-bromoprop-1-en-1-yl)benzene;(E)-(3-Bromoprop-1-en-1-yl)benzene;3-Bromo-1-phenyl-1-propene;[(E)-3-bromoprop-1-enyl]benzene;26146-77-0;3-phenyl-2-propenyl bromide;3-Bromo-1-phenyl propene-1;EINECS 224-511-5;[(1E)-3-bromoprop-1-en-1-yl]benzene;(3-Bromo-1-propen-1-yl)benzene;E-cinnamyl bromide;(E)-(3-bromoprop-1-enyl)benzene;3-Phenylallyl bromide;(E)-cinnamyl bromide;trans-Cinnamyl bromide;C9-H9-Br;[3-Bromo-1-propenyl]benzene;1-Phenyl-3-bromo-1-propene;SCHEMBL250822;SCHEMBL625625;E-(3-bromo-propenyl)-benzene;RUROFEVDCUGKHD-QPJJXVBHSA-;((E)-3-bromo-propenyl)-benzene;[(E)-3-bromo-1-propenyl]benzene;3-Bromo-1-phenyl-1-propene purum;AMY13659;NSC78446;[(1E)-3-Bromo-1-propenyl]benzene;[(1E)-3-bromoprop-1-enyl]benzene;Cinnamyl bromide, predominantly trans;MFCD00000245;NSC 78446;NSC-78446;3-Bromo-1-phenyl-1-propene, 97%;[(E)-3-bromo-prop-1-enyl]-benzene;1-((E)-3-bromoprop-1-enyl)benzene;1-[(E)-3-bromo-1-propenyl]benzene;AKOS015839134;AS-47511;CS-0063176;CS-0356738;EN300-343546;F14018;EN300-1246893;A826457;W-106217;3-Bromo-1-phenyl-1-propene, purum, >=98.0% (GC);3,5-DI-O-(P-TOLUOYL)-5-(2-HYDROXYETHYL)-2-DEOXYURIDINE;InChI=1/C9H9Br/c10-8-4-7-9-5-2-1-3-6-9/h1-7H,8H2/b7-4+

Chemical Property of Cinnamyl bromide

Chemical Property:

• Appearance/Colour: light yellow to beige cryst. low melting solid
• Vapor Pressure: 0.247mmHg at 25°C
• Melting Point: 26-29 °C(lit.)
• Refractive Index: n20/D 1.621(lit.)
• Boiling Point: 212.8 °C at 760 mmHg
• Flash Point: 105.2 °C
• PSA: 0.00000
• Density: 1.332 g/cm³
• LogP: 3.09470
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Water Solubility.: Soluble in methanol. Insoluble in water.
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 195.98876
• Heavy Atom Count: 10
• Complexity: 101

Purity/Quality:

99.5% ^*data from raw suppliers

Cinnamyl Bromide >98.0%(GC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=CCBr
• Isomeric SMILES: C1=CC=C(C=C1)/C=C/CBr
• Uses: Cinnamyl bromide, is used in the synthesis of naftifine.

Technology Process of Cinnamyl bromide

There total 56 articles about Cinnamyl bromide 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%

3-Phenylpropenol (104-54-1) → Cinnamyl bromide (4392-24-9)

Guidance literature:

With 1,1,1,2,2,2-hexamethyldisilane; pyridinium hydrobromide perbromide; In chloroform; at 25 ℃; for 0.5h;

DOI:10.1021/jo01297a020

Reference yield: 98.0%

Acetyl bromide (506-96-7) + benzyl cinnamyl ether (101306-31-4) → Benzyl acetate (140-11-4) + Cinnamyl bromide (4392-24-9)

Guidance literature:

With lithium bromide; In dichloromethane; at 30 - 35 ℃; for 6h; Inert atmosphere;

DOI:10.1021/jo801659g

Reference yield: 89.0%

1-((E)-3-(methoxymethoxy)prop-1-enyl)benzene (91970-13-7) → Cinnamyl bromide (4392-24-9)

Guidance literature:

With tetrabutylammomium bromide; 1-(n-butyl)-3-methylimidazolium tetrachloroindate; at 135 - 140 ℃; for 0.0333333h; chemoselective reaction; Microwave irradiation; Neat (no solvent);

DOI:10.1016/j.tetlet.2010.04.056

upstream raw materials:

1-phenylpropene

3-Phenylpropenol

1-Phenyl-2-propen-1-ol

(2E)-3-phenyl-2-propen-1-ol

Downstream raw materials:

diethyl (E)-cinnamyl malonate

N-(E)-cinnamyl-hydroxylamine

3-(trans-cinnamyloxy)-estra-1,3,5⁽¹⁰⁾-trien-17-one

N,N-dicinnamyl-N-tosylamine

Refernces

• 1、 Crawford, Evan T.,De Jesús Cruz, Pedro,Johnson, Jeffrey S.,Liu, Shubin. "Stereodivergent Nucleophilic Additions to Racemic β-Oxo Acid Derivatives: Fast Addition Outcompetes Stereoconvergence in the Archetypal Configurationally Unstable Electrophile". supporting information. p. 16264 - 16273. Retrieved 2021/10/21.
• 2、 Mupparapu, Nagaraju,Lin, Yu-Hsin Cindy,Kim, Tae Ho,Elshahawi, Sherif I.. "Regiospecific Synthesis of Calcium-Independent Daptomycin Antibiotics using a Chemoenzymatic Method". supporting information. p. 4176 - 4182. Retrieved 2021/02/01.