Benzaldehyde

Base Information

• Chemical Name: Benzaldehyde
• CAS No.: 100-52-7
• Molecular Formula: C7H6O
• Molecular Weight: 106.124
• Hs Code.: 2912210000
• European Community (EC) Number: 202-860-4,640-369-0,693-271-5
• ICSC Number: 0102
• NSC Number: 7917
• UN Number: 1990
• UNII: TA269SD04T
• DSSTox Substance ID: DTXSID8039241
• Nikkaji Number: J4.010J
• Wikipedia: Benzaldehyde
• Wikidata: Q372524
• NCI Thesaurus Code: C2591
• RXCUI: 1314334
• Metabolomics Workbench ID: 38822
• ChEMBL ID: CHEMBL15972
• Mol file: 100-52-7.mol

Synonyms:benzaldehyde;benzaldehyde, formyl-(14)C-labeled

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Chemical Property of Benzaldehyde

Chemical Property:

• Appearance/Colour: colorless liquid
• Vapor Pressure: 0.974mmHg at 25°C
• Melting Point: -26 °C
• Refractive Index: n20/D 1.545(lit.)
• Boiling Point: 178.7 °C at 760 mmHg
• Flash Point: 62.8 °C
• PSA: 17.07000
• Density: 1.049 g/cm³
• LogP: 1.49910
• Water Solubility.: <0.01 g/100 mL at 19.5℃
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 106.041864811
• Heavy Atom Count: 8
• Complexity: 72.5
• Transport DOT Label: Class 9

Purity/Quality:

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn:Harmful
• Statements: R22:
• Safety Statements: S24:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Benzaldehydes
• Canonical SMILES: C1=CC=C(C=C1)C=O
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes.
• Importance and Versatility: Benzaldehyde is a vital organic compound widely used as an intermediate in various industries. It serves as a key building block for the synthesis of perfumes, epoxy resins, plasticizers, drugs, sweeteners, and fine chemicals.
• Industrial Production: Benzaldehyde is industrially produced through two main processes: the catalytic oxidation of toluene to benzoic acid with oxygen and the hydrolysis of benzyl chloride.; Current synthetic routes have drawbacks such as high temperatures, long reaction times, and the production of chloride wastes, resulting in low catalytic conversion and poor benzaldehyde yield.
• Alternative Production Methods: Selective oxidation of styrene to benzaldehyde has gained attention due to its simplicity and environmental friendliness.; Various homogeneous and heterogeneous catalysts have been explored for this process, with heterogeneous catalysts being more promising due to easy separation and recycling.
• Challenges in Toluene Oxidation: Toluene oxidation to benzaldehyde presents challenges, with traditional processes requiring high temperatures and pressures.; Photocatalysis offers a green and low-energy consumption alternative, but its low solar energy conversion efficiency limits practical applications.; Strategies to improve photocatalytic efficiency include enhancing separation and migration rates of photogenerated charge carriers.

Technology Process of Benzaldehyde

There total 6900 articles about Benzaldehyde 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: 78.8%

1,1-dimethylethyl-1-phenylethyl peroxide (28047-94-1) → 1-Phenylethanol (98-85-1,13323-81-4) + benzaldehyde (100-52-7) + acetophenone (98-86-2) + acetone (67-64-1) + tert-butyl alcohol (75-65-0)

Guidance literature:

In chlorobenzene; at 129.2 ℃; Product distribution; Rate constant; also with styrene, dimethylaniline, and 2,6-di-tert-butyl-p-cresol (radical traps);

DOI:10.1021/jo00144a022

Reference yield: 71.0%

2-phenyl-1,3-oxathiolane (5721-88-0) + 2-carboxybenzene diazonium chloride (4661-46-5) → benzaldehyde (100-52-7) + phenylthioethylene (1822-73-7)

Guidance literature:

With methyloxirane; In 1,2-dichloro-ethane; for 0.75h; Mechanism; Heating;

DOI:10.1016/S0040-4039(00)98960-3

Reference yield: 67.0%

ethylbenzene (100-41-4,27536-89-6) → styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + ethene (74-85-1) + benzaldehyde (100-52-7) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

With air; Cd-Sn-P-O; at 515 ℃; under 760 Torr; Mechanism; Product distribution; other catalyst, vari. of reagebt composition, of temperature; selectivity to styrene conversion investigated;

upstream raw materials:

diazomethane

2-acetoxy-2-phenylacetyl chloride

piperidine

5-[(phenyl)(phenylamino)]pentan-3-one

Downstream raw materials:

DL-O¹,O⁶-dibenzoyl-O²,O³;O⁴,O⁵-((RS,RS)-dibenzylidene)-galactitol

11-benzylidene-2,3-dimethoxy-strychnidin-10-one

acetophenone

(E)-6-methyl-4-styryl-2H-chromen-2-one

Refernces

• 1、 Estrada, Miguel,Costa, Vinícius V.,Beloshapkin, Sergey,Fuentes, Sergio,Stoyanov, Evgenii,Gusevskaya, Elena V.,Simakov, Andrey. "Aerobic oxidation of benzyl alcohol in methanol solutions over Au nanoparticles: Mg(OH)2 vs MgO as the support". . p. 96 - 103. Retrieved 2014.
• 2、 Park, Jinhee,Li, Jian-Rong,Chen, Ying-Pin,Yu, Jiamei,Yakovenko, Andrey A.,Wang, Zhiyong U.,Sun, Lin-Bing,Balbuena, Perla B.,Zhou, Hong-Cai. "A versatile metal-organic framework for carbon dioxide capture and cooperative catalysis". . p. 9995 - 9997. Retrieved 2012.
• 3、 Farzaneh, Faezeh,Sadeghi, Yasaman. "Immobilized V-MIL-101 on modified Fe3O4 nanoparticles as heterogeneous catalyst for epoxidation of allyl alcohols and alkenes". . p. 275 - 281. Retrieved 2015.
• 4、 Rohmann, Kai,H?lscher, Markus,Leitner, Walter. "Can Contemporary Density Functional Theory Predict Energy Spans in Molecular Catalysis Accurately Enough to Be Applicable for in Silico Catalyst Design? A Computational/Experimental Case Study for the Ruthenium-Catalyzed Hydrogenation of Olefins". . p. 433 - 443. Retrieved 2016.
• 5、 Neeli, Chinna Krishna Prasad,Narani, Anand,Marella, Ravi Kumar,Rama Rao, Kamaraju Seetha,Burri, David Raju. "Selective benzylic oxidation of alkylaromatics over Cu/SBA-15 catalysts under solvent-free conditions". . p. 5 - 9. Retrieved 2013.
• 6、 Bagherzadeh, Mojtaba,Ashouri, Fatemeh,Crossed D Signakovi?, Marijana. "Synthesis, structural characterization and application of a 2D coordination polymer of Mn-terephthalate as a heterogeneous catalyst for olefin oxidation". . p. 167 - 173. Retrieved 2014.
• 7、 Wang, Yongjun,Wen, Xu,Rong, Chunying,Tang, Senpei,Wu, Wenfeng,Zhang, Chao,Liu, Yachun,Fu, Zaihui. "Weakly distorted 8-quinolinolato iron(III) complexes as effective catalysts for oxygenation of organic compounds by hydrogen peroxide". . p. 103 - 109. Retrieved 2016.
• 8、 Corey,Fleet. "-". . p. 4499,4500. Retrieved 1973.
• 9、 Zolfigol, Mohammad A.,Shirini, Farhad,Mohammadpoor-Baltork, Iraj,Choghamarani, Arash Gh.,Hajjami, Maryam,Sedaghat, Abdol M.. "Silica chromate as an oxidising agent for the chemoselective oxidation of alcohols and the oxidative deprotection of trimethylsilyl ethers". . p. 113 - 116. Retrieved 2005.
• 10、 Fujihira, Masamichi,Satoh, Yoshiharu,Osa, Tetsuo. "HETEROGENEOUS PHOTOCATALYTIC OXIDATION OF AROMATIC COMPOUNDS ON SEMICONDUCTOR MATERIALS: THE PHOTO-FENTON REACTION". . p. 1053 - 1056. Retrieved 1981.