2-Methoxybenzaldehyde

Base Information

• Chemical Name: 2-Methoxybenzaldehyde
• CAS No.: 135-02-4
• Molecular Formula: C8H8O2
• Molecular Weight: 136.15
• Hs Code.: 29124900
• European Community (EC) Number: 205-171-7
• NSC Number: 58960
• UNII: 7CP821WF2W
• DSSTox Substance ID: DTXSID1051690
• Nikkaji Number: J5.602B
• Wikipedia: 2-Methoxybenzaldehyde
• Wikidata: Q18465935
• Metabolomics Workbench ID: 46198
• ChEMBL ID: CHEMBL396295
• Mol file: 135-02-4.mol

Synonyms:2-METHOXYBENZALDEHYDE;135-02-4;o-Anisaldehyde;o-Methoxybenzaldehyde;Benzaldehyde, 2-methoxy-;2-Anisaldehyde;Salicylaldehyde methyl ether;6-Methoxybenzaldehyde;2-Methoxybenzenecarboxaldehyde;Benzaldehyde, o-methoxy-;2-Methoxyphenylformaldehyde;2-methoxy-benzaldehyde;ortho-anisaldehyde;Formylanisole, o-;O-FORMYLANISOLE;2-Methoxy benzaldehyde;EINECS 205-171-7;MFCD00003308;NSC 58960;2-(Methoxy-d3)benzaldehyde;BRN 0606301;UNII-7CP821WF2W;AI3-01375;7CP821WF2W;DTXSID1051690;NSC-58960;4-08-00-00180 (Beilstein Handbook Reference);o -anisaldehyde;orthoanisaldehyde;0-anisaldehyde;o- Anisaldehyde;methoxy benzaldehyde;NSC58960;o-methoxy benzaldehyde;o-methoxy-benzaldehyde;orthomethoxybenzaldehyde;O-Anisaldehyde, 8CI;2 - methoxybenzaldehyde;o-Anisaldehyde, >=97%;(2'-methoxyphenyl)methanone;SCHEMBL66490;2-Methoxybenzaldehyde, 98%;O-ANISALDEHYDE [FHFI];METHOXYBENZALDEHYDE, O-;CHEMBL396295;o-Anisaldehyde, >=97%, FG;DTXCID0030245;FEMA NO. 4077;O-ANISALDEHYDE [USP-RS];CHEBI:172139;2-Methoxybenzaldehyde;O-METHOXYBENZALDEHYDE [FHFI];Tox21_303774;STK199251;AKOS000119747;AB00311;CS-W018515;LS-2895;NCGC00357066-01;2-Methoxybenzaldehyde, analytical standard;AS-13064;CAS-135-02-4;HY-77995;SY001108;o-Anisaldehyde, Salicylaldehyde methyl ether;A0479;FT-0631782;EN300-16099;D71156;A853555;Q-200299;Q18465935;Z53833342;F0913-0491;o-Anisaldehyde, United States Pharmacopeia (USP) Reference Standard

Chemical Property of 2-Methoxybenzaldehyde

Chemical Property:

• Appearance/Colour: light yellow to pale brown
• Vapor Pressure: 0.00128mmHg at 25°C
• Melting Point: 34-40 °C(lit.)
• Refractive Index: 1.5608
• Boiling Point: 243.5 °C at 760 mmHg
• Flash Point: 100.7 °C
• PSA: 26.30000
• Density: 1.088 g/cm³
• LogP: 1.50770
• Storage Temp.: Store below +30°C.
• Sensitive.: Air Sensitive
• Solubility.: Solubility Slightly soluble in water; soluble in ethanol
• Water Solubility.: insoluble
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 136.052429494
• Heavy Atom Count: 10
• Complexity: 112

Purity/Quality:

99% ^*data from raw suppliers

2-Methoxybenzaldehyde ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Benzaldehydes
• Canonical SMILES: COC1=CC=CC=C1C=O
• Description: O-Anisaldehyde (also 2-methoxybenzaldehyde) is found in cassia oil, cinnamon bark, and cinnamon bark oil. It is a clear colorless liquid with a strong aroma. O-Anisaldehyde is used as a flavor agent in foods including nonalcoholic/alcoholic beverages, baked goods, chewing gum, confections, frozen dairy, fruit ices, hard/soft candy, instant coffee, tea, Jams, jellies, and milk products. O-Anisaldehyde has been used to examine the acaricidal activity of Periploca sepium oil and its active component against Tyrophagus and to obtain good enantioselectivities using Cu(OAc)(2)-bis(oxazolines) via hydrogen bonding in asymmetric Henry reaction. o-Methoxybenzaldehyde has a faint, sweet, floral odor. It blends well with cassia. It has a spice-like flavor, quite bitter above 30 - 40 ppm. May be prepared from salicylaldehyde and dimethyl sulfate in weak alkaline solution.
• Uses: 2-Methoxybenzaldehyde has been used to examine the acaricidal activity of Periploca sepium oil and its active component against Tyrophagus. It has also been used to obtain good enantioselectivities using Cu(OAc)(2)-bis(oxazolines) via hydrogen bonding in asymmetric Henry reaction. Intermediate. 2-Methoxybenzaldehyde has been used to obtain good enantioselectivities using Cu(OAc)(2)-bis(oxazolines) via hydrogen bonding in asymmetric Henry reaction.

Technology Process of 2-Methoxybenzaldehyde

There total 212 articles about 2-Methoxybenzaldehyde 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: 80.0%

2-(2-methoxyphenyl)-1,3-dithiolane (24588-76-9) → 2-Methoxybenzoic acid (579-75-9) + ortho-anisaldehyde (135-02-4)

Guidance literature:

With sodium nitrate; sulfuric acid; silica gel; In dichloromethane; at 20 ℃; for 0.166667h;

DOI:10.1055/s-2006-926431

Reference yield: 53.0%

(2-methoxyphenyl)methanol (612-16-8) → formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2-methoxy-phenol (90-05-1) + ortho-anisaldehyde (135-02-4)

Guidance literature:

With Amberlite IRA-120; urea-hydrogen peroxide; 1-n-butyl-3-methylimidazolim bromide; at 70 ℃; for 1h;

DOI:10.1246/cl.2008.496

Reference yield: 50.0%

carbon monoxide (201230-82-2) + methoxybenzene (100-66-3) → tris(4-methoxyphenyl)methane (7511-68-4) + 4-methoxy-benzaldehyde (123-11-5) + ortho-anisaldehyde (135-02-4) + 1-(4-methoxyphenyl)ethanone (100-06-1)

Guidance literature:

With hydrogen fluoride; boron trifluoride; at 45 ℃; for 4.5h; under 37503.8 - 60006 Torr; Further Variations:; Reagents; time; Product distribution;

DOI:10.1055/s-2006-942480

upstream raw materials:

quinoline

hydrogen cyanide

2-Methoxybenzoyl chloride

2-methoxy-benzenediazonium

Downstream raw materials:

N-(2-methoxybenzyl)-(2-pyridyl)amine

3c-(2-methoxy-phenyl)-2-[2]thienyl-acrylonitrile

(2-methoxy-benzyl)-(1H-[1,2,4]triazol-3-yl)-amine

(E)-1-(furan-2-yl)-3 (2-methoxyphenyl)-2-propen-1-one

Refernces

• 1、 Sharma, Pankaj,Gupta, Monika,Gupta, Rajive,Gupta, Manjulla. "Silica functionalized Cu(II) catalysed selective oxidation of benzyl alcohols using TEMPO and molecular oxygen as an oxidant". . p. 1485 - 1489. Retrieved 2015.
• 2、 Sidgwick,Bayliss. "-". . p. 2027,2028. Retrieved 1930.
• 3、 Kargar, Hadi,Fallah-Mehrjardi, Mehdi,Behjatmanesh-Ardakani, Reza,Munawar, Khurram Shahzad,Ashfaq, Muhammad,Tahir, Muhammad Nawaz. "Synthesis, spectral characterization, SC-XRD, HSA, DFT and catalytic activity of a dioxidomolybdenum complex with aminosalicyl-hydrazone Schiff base ligand: An experimental and theoretical approach". . . Retrieved 2021.
• 4、 Chen, Chao,Ni, Shengliang,Zheng, Qing,Yu, Meifang,Wang, Hangxiang. "Synthesis, Structure, Biological Evaluation, and Catalysis of Two Pyrazole-Functionalized NHC–RuIIComplexes". . p. 616 - 622. Retrieved 2017.
• 5、 Kumar, Balagani Sathish,Negi, Arvind S.. "A frank synthesis of alkyl-aryl ethers from 2-halobenzaldehydes and aromatic olefins without transition metal co-catalyst and ligand". . p. 2340 - 2344. Retrieved 2015.
• 6、 Kargar, Hadi,Fallah-Mehrjardi, Mehdi,Behjatmanesh-Ardakani, Reza,Munawar, Khurram Shahzad,Ashfaq, Muhammad,Tahir, Muhammad Nawaz. "Selective oxidation of benzyl alcohols to benzaldehydes catalyzed by dioxomolybdenum Schiff base complex: synthesis, spectral characterization, crystal structure, theoretical and computational studies". . p. 437 - 455. Retrieved 2021.
• 7、 Santaniello, Enzo,Milani, Fulvia,Casati, Rosangela. "Tetrabutylammonium Chlorochromate, A New Mild and Selective Oxidizing Agent". . p. 749 - 751. Retrieved 1983.
• 8、 Wang, Liang,Wang, Yaoyao,Tao, Yu,Zhang, Nana,Li, Shubai. "Nickel catalyzed hydrosilane reduction of (het)arenecarboxylic acids into aldehydes". . p. 271 - 273. Retrieved 2021/05/04.
• 9、 Li, Xue,Bai, Fang,Liu, Chaogan,Ma, Xiaowei,Gu, Chengzhi,Dai, Bin. "Selective Electrochemical Oxygenation of Alkylarenes to Carbonyls". supporting information. p. 7445 - 7449. Retrieved 2021/10/02.