alpha-Bromocinnamic aldehyde

Base Information

• Chemical Name: alpha-Bromocinnamic aldehyde
• CAS No.: 5443-49-2
• Molecular Formula: C9H7BrO
• Molecular Weight: 211.058
• Hs Code.: 29130000
• NSC Number: 19806
• Nikkaji Number: J726.494A
• Mol file: 5443-49-2.mol

Synonyms:(e)-2-bromo-3-phenylacrylaldehyde;.alpha.-Bromocinnamaldehyde;.alpha.-Bromocinnamic aldehyde;99686-39-2;alpha-Bromo-cis-cinnamaldehyde;SCHEMBL1552546;NSC19806;NSC-19806;CS-0369174

Chemical Property of alpha-Bromocinnamic aldehyde

Chemical Property:

• Appearance/Colour: light yellow to ochre crystalline powder
• Vapor Pressure: 0.000874mmHg at 25°C
• Melting Point: 66-68 °C(lit.)
• Refractive Index: 1.627
• Boiling Point: 304.4 °C at 760 mmHg
• Flash Point: 110.2 °C
• PSA: 17.07000
• Density: 1.499 g/cm³
• LogP: 2.62130
• Storage Temp.: 2-8°C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 209.96803
• Heavy Atom Count: 11
• Complexity: 157

Purity/Quality:

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

α-Bromocinnamaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36/37/39-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=C(C=O)Br
• Isomeric SMILES: C1=CC=C(C=C1)/C=C(\C=O)/Br
• Uses: α-Bromocinnamaldehyde was used in the synthesis of 3,4-diaryl 1H-pyrazoles. It was also used in the preparation of spiro imidazolidine-oxazolidine intermediate via guanidinium ylide mediated aziridination.

Technology Process of alpha-Bromocinnamic aldehyde

There total 11 articles about alpha-Bromocinnamic aldehyde 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%

2,3-dibromo-3-phenyl propanal (66894-04-0,62248-40-2) → α-bromocinnamaldehyde (5443-49-2)

Guidance literature:

With caesium carbonate; In toluene; at 25 ℃;

DOI:10.1002/chem.201103358

Reference yield: 85.0%

3-phenyl-propenal (104-55-2) → α-bromocinnamaldehyde (5443-49-2)

Guidance literature:

With pyridine; Phenylselenyl bromide; In dichloromethane; at 37 ℃; for 168h;

DOI:10.1016/S0040-4039(01)81890-6

Reference yield: 80.0%

ethanol (64-17-5) + 2,2-dibromo-3-phenyl-propionaldehyde → α-bromocinnamaldehyde (5443-49-2) + ethyl cinnamate (4192-77-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,3-bis(mesityl)imidazolium chloride; In tetrahydrofuran; at 20 ℃; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2012.05.109

upstream raw materials:

diethyl ether

2,3-dibromo-3-phenyl propanal

Triphenylphosphin-brom-formyl-methylen

benzaldehyde

Downstream raw materials:

(R,E)-3-bromo-1-nitro-4-phenylbut-3-en-2-ol

Methyl cinnamate

ethyl cinnamate

prop-2-ynyl 3-phenylacrylate

Refernces

First synthesis of cis-enediynes from 1,5-diynes by an acid-mediated allylic rearrangement

10.1016/0040-4039(96)01924-7

The study presents the first synthesis of cis-enediynes from 1,5-diyne 7 through an acid-mediated allylic rearrangement using (+)-10-camphorsulfonic acid (CSA) in CH2Cl2 at 20 °C in the presence of ROH or RSH. The key chemicals involved include the starting material 1,5-diyne 7, which is prepared from a-bromocinnamaldehyde (5) via cross-coupling with H2C(CH2)4OMe and subsequent addition of LiCCCH2SiMe3. The reaction yields cis-enediyne 10 as the major product, along with trans-enediyne 8 and 1,5-diyne 9. The study also explores the allylic rearrangement in the presence of various nucleophiles (ROH and RSH), achieving high regioselectivity and trans/cis stereoselectivity. The synthesized cis-enediynes can be oxidized to form diradicals capable of DNA cleavage. Additionally, an 11-membered ring enediyne 15 is synthesized using a similar acid-promoted allylic rearrangement strategy, highlighting the potential for enediyne prodrug design and synthesis.