Salicylaldehyde

Base Information

• Chemical Name: Salicylaldehyde
• CAS No.: 90-02-8
• Deprecated CAS: 1563136-87-7
• Molecular Formula: C7H6O2
• Molecular Weight: 122.123
• Hs Code.: 29122990
• European Community (EC) Number: 201-961-0
• NSC Number: 187662,49178
• UNII: 17K64GZH20
• DSSTox Substance ID: DTXSID1021792
• Nikkaji Number: J10.607K
• Wikipedia: Salicylaldehyde
• Wikidata: Q414492
• Pharos Ligand ID: NUCH8RWMTFHC
• Metabolomics Workbench ID: 46396
• ChEMBL ID: CHEMBL108925
• Mol file: 90-02-8.mol

Synonyms:2-hydroxybenzaldehyde;salicylaldehyde;Salicylaldehyde ester

Chemical Property of Salicylaldehyde

Chemical Property:

• Appearance/Colour: colourless to yellow oily liquid with a bitter almond odour
• Vapor Pressure: 1 mm Hg ( 33 °C)
• Melting Point: 1-2 °C(lit.)
• Refractive Index: 1.448 - 1.453
• Boiling Point: 193.7 °C at 760 mmHg
• PKA: 8.37(at 25℃)
• Flash Point: 76.7 °C
• PSA: 37.30000
• Density: 1.226 g/cm³
• LogP: 1.20470
• Storage Temp.: Store below +30°C.
• Sensitive.: Air & Light Sensitive
• Solubility.: 4.9g/l
• Water Solubility.: slightly soluble
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 122.036779430
• Heavy Atom Count: 9
• Complexity: 101

Purity/Quality:

99% ^*data from raw suppliers

Salicylaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,N
• Statements: 21/22-36/38-68-36/37/38-20/21/22-51-36-51/53-22
• Safety Statements: 26-36/37-36/37/39-36-61-64-29/35

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)O
• Description: Salicylaldehyde (2-hydroxybenzaldehyde) is an organic compound with the formula C6H4CHO-2-OH. Along with 3-hydroxybenzaldehyde and 4-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde. It is a colorless or pale yellow liquid with a bitter almond odor and a burning taste. It is soluble in alcohol, benzene, and ether, and very slightly soluble in water. Salicylaldehyde is found in shrubs of the genus Spiraea and is usually produced from phenol by the action of chloroform in the presence of an alkali base. It is used in the production of coumarin, saligenin, and salicylaldoxime (an important analytical reagent), and also in analytical chemistry—for example, to detect hydrazine. Besides, salicylaldehyde is a key precursor to various chelating agents and a flavouring ingredient.
• Uses: Salicylaldehyde, is used as flavor and fragrance components. Salicylaldehyde is also a common highly-functionalized arene, that can be used as a precursor in the synthesis of other chemicals.

Technology Process of Salicylaldehyde

There total 422 articles about Salicylaldehyde 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: 52.0%

pyCo(N,N'-bis(salicylidene)-o-phenylenediamino)NO2 + boron trifluoride diethyl etherate (109-63-7) → pyCo(N,N'-bis(salicylidene)-o-phenylenediamino)NO*BF3 + benzaldehyde (100-52-7) + salicylaldehyde (90-02-8)

Guidance literature:

With benzyl alcohol; In 1,2-dichloro-ethane; byproducts: BF3-pyridine complex, H2O; under Ar addn. of BF3*Et2O to mixt. of alcohol and complex in (CH2)2Cl2, further addn. of BF3*Et2O, heating in 60°C oil bath for 30 min,addn. 1 drop of pyridine in hexane, removing BF3-pyridine complex pptd.; solvent removing in vac., addn. of petroleum ether to resulting oil, filtration, drying under Ar;

DOI:10.1021/ja00402a044

Reference yield: 48.0%

1-phenyl-2-nitroprop-1-ene (705-60-2,18315-84-9,58321-79-2) → benzylidene dichloride (98-87-3) + benzaldehyde (100-52-7) + salicylaldehyde (90-02-8) + acetoximino-2 chloro-1 phenyl-1 propane (81932-05-0)

Guidance literature:

With aluminium trichloride; chlorure d'acetyle; In dichloromethane; at 0 ℃; for 5h;

DOI:10.1016/0040-4020(81)85014-4

Reference yield: 46.0%

2-methoxybenzaldehyde O-methyloxime (107369-63-1) → salicylonitrile (611-20-1) + 2-methoxy-benzonitrile (6609-56-9) + salicylaldehyde (90-02-8)

Guidance literature:

at 650 ℃; under 0.03 Torr;

DOI:10.1039/b103181n

upstream raw materials:

3-oxo-2,3-dihydrobenzo[b]furan

formic acid

carbonic acid bis-(2-dichloromethyl-phenyl ester)

salicylonitrile

Downstream raw materials:

4-(3-oxo-3-phenyl-propionimidoyl)-morpholine

4-(2-hydroxythiobenzoyl)morpholine

2-(dimorpholinomethyl)phenol

2-[3-(piperidin-1-yl)propoxy]benzaldehyde

Refernces

• 1、 Shahamat, Zahra,Nemati, Firouzeh,Elhampour, Ali. "Highly effective oxidation of benzyl alcohols to benzaldehydes over a new hypervalent iodine(III) reagent with the polymeric framework and magnetic feature as reusable heterogeneous nanocatalyst". . . Retrieved 2020.
• 2、 Zhou, Jing-Yao,Chen, Zhao-Gen,Wu, Shi-Hui. "Tin-promoted Stereocontrolled Intramolecular Allylation of Carbonyl Compounds: a Facile and Stereoselective Method for Ring Construction". . p. 2783 - 2784. Retrieved 1994.
• 3、 Dash, Anadi C.,Dash, Bhasker,Panda, Debraj. "Hydrolysis of Imines. 4. Micellar Effects upon the Spontaneous Acid, Base, and Copper(II) Ion Induced Hydrolysis of N-Salicylidene-2-aminothiazole and N-Salicylidene-2-aminopyridine". . p. 2905 - 2910. Retrieved 1985.
• 4、 Winkler, Daniela,Banke, Sophie,Kurz, Philipp. "Fluorimetric Detection of Phosphates in Water Using a Disassembly Approach: A Comparison of FeIII-, ZnII-, MnII- and MnIII-salen Complexes". . p. 933 - 939. Retrieved 2020.
• 5、 Huang, You,Li, Xiaohu. "Phosphine-catalyzed sequential (2+3)/(2+4) annulation of γ-vinyl allenoates: Access to the synthesis of chromeno[4,3-: B] pyrroles". supporting information. p. 9934 - 9937. Retrieved 2021/10/12.
• 6、 Dhabbe, Rohant,Gaikwad, Pratapsingh,Kakade, Bhalchandra,Kamble, Prakash,Kurane, Rajnikant,Parase, Haridas,Sabale, Sandip. "Magneto-structural properties and reliability of (Mn/Ni/Zn) substituted cobalt-copper ferrite heterogeneous catalyst for selective and efficient oxidation of aryl alcohols". . . Retrieved 2021/09/28.