4-Bromobenzaldehyde

Base Information

• Chemical Name: 4-Bromobenzaldehyde
• CAS No.: 1122-91-4
• Deprecated CAS: 2222571-84-6
• Molecular Formula: C7H5BrO
• Molecular Weight: 185.02
• Hs Code.: 29130000
• European Community (EC) Number: 214-365-0
• NSC Number: 21638
• UNII: 4L8VM24F65
• DSSTox Substance ID: DTXSID5061534
• Nikkaji Number: J30.727K
• Wikidata: Q27259983
• ChEMBL ID: CHEMBL3753357
• Mol file: 1122-91-4.mol

Synonyms:Benzaldehyde,p-bromo- (6CI,8CI);1-Bromo-4-formylbenzene;4-Formylbromobenzene;4-Formylphenyl bromide;NSC 21638;p-Bromobenzaldehyde;

Chemical Property of 4-Bromobenzaldehyde

Chemical Property:

• Appearance/Colour: white crystalline solid
• Vapor Pressure: 0.0249mmHg at 25°C
• Melting Point: 55-58 °C
• Refractive Index: 1.547
• Boiling Point: 244 °C at 760 mmHg
• Flash Point: 108.9 °C
• PSA: 17.07000
• Density: 1.577 g/cm³
• LogP: 2.26160
• Storage Temp.: Room temperature.
• Sensitive.: Air Sensitive
• Solubility.: Chloroform, Ethyl Acetate
• Water Solubility.: INSOLUBLE
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 183.95238
• Heavy Atom Count: 9
• Complexity: 95.1

Purity/Quality:

99% ^*data from raw suppliers

4-Bromobenzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-43
• Safety Statements: 26-36/37-36/37/39-22

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Benzaldehydes
• Canonical SMILES: C1=CC(=CC=C1C=O)Br
• Uses: 4-Bromobenzaldehyde is widely utilized as an intermediate for the preparation of agrochemicals, pharmaceuticals and other organic compounds. It is used as a precursor and reacts with sulfamethoxazole to prepare Schiff?s base, 4-[(4-Bromo-benzylidene)-amino]-N-(5-methyl-isoxazol-3-yl)-benzene sulfonamide, which can be used for the photo stability of polyvinyl chloride (PVC). It plays an important role in palladium-catalyzed mono- and bis-arylation of 3,4-(ethylenedioxy)thiophenes. It is employed in a cross-coupling study with potassium vinyltrifluoroborate. Employed in palladium-catalyzed mono- and bis-arylation of 3,4-(ethylenedioxy)thiophenes. Also used in a cross-coupling study with potassium vinyltrifluoroborate.

Technology Process of 4-Bromobenzaldehyde

There total 309 articles about 4-Bromobenzaldehyde 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: 85.0%

(1R*,2R*)-1-(4-bromophenyl)-2-phenylethane-1,2-diol → benzaldehyde (100-52-7) + 4-bromo-benzaldehyde (1122-91-4)

Guidance literature:

With C₂₁H₁₂Cl₆NO₄V; In toluene; at 80 ℃; under 760.051 Torr; chemoselective reaction;

DOI:10.1002/adsc.201800050

Reference yield: 84.0%

4-bromobenzenemethanol (873-75-6) → 4-Bromobenzoic acid (586-76-5) + 4-bromo-benzaldehyde (1122-91-4)

Guidance literature:

With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium chloride; oxygen; In 1,2-dichloro-ethane; at 25 ℃; for 48h; Schlenk technique;

DOI:10.1055/s-0036-1591761

Reference yield: 78.0%

4-chlorobenzoyl chloride (586-75-4) → benzaldehyde (100-52-7) + 4-bromo-benzaldehyde (1122-91-4)

Guidance literature:

With tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; Yield given; Ambient temperature;

DOI:10.1021/jo00335a023

upstream raw materials:

chloroform

diazotiertes 4-Amino-benzaldehyd

bis(4-bromobenzyl) ether

para-bromotoluene

Downstream raw materials:

(E)-3-(4-bromophenyl)-2-methylacrylic acid

1-ethyl-4-(4-bromo-trans-styryl)-pyridinium; iodide

(E)-N'-(4-bromobenzylidene)isonicotinohydrazide

2,6-bis(4'-bromobenzylidene)cyclohexanone

Refernces

• 1、 Zolfigol, Mohammad Ali,Khazaei, Ardeshir,Ghorbani-Choghamarani, Arash,Rostami, Amin. "Microwave-assisted chemoselective regeneration of carbonyl compounds from oximes by silica chromate/WET SiO2 under solvent-free conditions". . p. 2453 - 2458. Retrieved 2006.
• 2、 Keypour, Hassan,Saremi, Shokoufeh Ghahri,Veisi, Hojat,Azadbakht, Reza. "Novel Schiff base Mn(III) and Co(II) complexes supported on Co nanoparticles: Efficient and recyclable magnetic nanocatalysts for alcohol oxidation". . p. 77020 - 77029. Retrieved 2016.
• 3、 Trahanovsky et al.. "-". . p. 3865. Retrieved 1967.
• 4、 Sierra,Mancheno,Saez,Del Amo. "Chromium(0)-carbene complexes as carbene sources: Self-dimerization and inter- and intramolecular C-H insertion reactions catalyzed by Pd(OAc)2". . p. 6812 - 6813. Retrieved 1998.
• 5、 Degani, Iacopo,Fochi, Rita,Regondi, Valeria. "Mercury(II) Oxide/35percent Aqueous Tetrafluoroboric Acid/Tetrahydrofuran: An Improved Reagent for the Hydrolysis of Cyclic Hemithioacetals, Dithioacetals, and Ortho Esters". . p. 51 - 53. Retrieved 1981.
• 6、 Moorthy, Jarugu Narasimha,Singhal, Nidhi,Senapati, Kalyan. "Oxidations with IBX: Benzyl halides to carbonyl compounds, and the one-pot conversion of olefins to 1,2-diketones". . p. 1757 - 1761. Retrieved 2006.
• 7、 Nicolaou,Baran,Zhong. "Selective oxidation at carbon adjacent to aromatic systems with IBX". . p. 3183 - 3185. Retrieved 2001.
• 8、 Lee, Kyoungsoo,Maleczka Jr., Robert E.. "Pd(0)-catalyzed PMHS reductions of aromatic acid chlorides to aldehydes". . p. 1887 - 1888. Retrieved 2006.
• 9、 Iida, Takehiko,Wada, Toshihiro,Tomimoto, Koji,Mase, Toshiaki. "Tributylmagnesium ate complex-mediated novel bromine-magnesium exchange reaction for selective monosubstitution of dibromoarenes". . p. 4841 - 4844. Retrieved 2001.
• 10、 Sharma, Rajesh V.,Soni, Kapil K.,Dalai, Ajay K.. "Preparation, characterization and application of sulfated Ti-SBA-15 catalyst for oxidation of benzyl alcohol to benzaldehyde". . p. 87 - 91. Retrieved 2012.