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CAS

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o-Anisaldehyde, also known as 2-methoxybenzaldehyde, is a clear colorless liquid with a strong aroma and a faint, sweet, floral odor. It is found in cassia oil, cinnamon bark, and cinnamon bark oil (Cinnamomom zeylanicum Blume), particularly in Sri Lanka. It has a spice-like flavor, which is quite bitter above 30-40 ppm. o-Anisaldehyde can be prepared from salicylaldehyde and dimethyl sulfate in a weak alkaline solution. As a chemical, it is a colorless to cream amber crystalline powder with a sweet powdery hawthorn guaiacol vanilla acetophenone almond aroma. It has a medium strength odor with an anisic type and is recommended to be smelled in a 10.00% solution or less.

135-02-4

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135-02-4 Usage

Uses

Used in Flavor Industry:
o-Anisaldehyde is used as a flavor agent for various food products, including nonalcoholic/alcoholic beverages, baked goods, chewing gum, confections, frozen dairy, fruit ices, hard/soft candy, instant coffee, tea, jams, jellies, and milk products. It provides a unique aroma and taste to these products, enhancing their overall sensory experience.
Used in Chemical Synthesis:
o-Anisaldehyde serves as an intermediate in the synthesis of various chemicals and compounds. It has been used to obtain good enantioselectivities using Cu(OAc)(2)-bis(oxazolines) via hydrogen bonding in asymmetric Henry reactions, which is crucial for the development of enantiomerically pure compounds with specific biological activities.
Used in Pest Control:
o-Anisaldehyde has been utilized to examine the acaricidal activity of Periploca sepium oil and its active component against Tyrophagus, a type of mite. This application demonstrates its potential use in the development of natural and effective pest control solutions.

References

[1] George A. Burdock (2016) Fenraoli’s Handbook of Flavor Ingredients, Sixth Edition. [2] https://www.alfa.com/en/catalog/A10770/

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 11, p. 943, 1974 DOI: 10.1002/jhet.5570110616Tetrahedron Letters, 25, p. 1843, 1984 DOI: 10.1016/S0040-4039(01)90056-5

Biochem/physiol Actions

Naturally-occurring aromatic aldehyde with acaricidal activity. May condense with L-tryptophan in foods to form the corresponding phenolic tetrahydro-β-carboline-3-carboxylic acid which is a potent antioxidant.

Safety Profile

Moderately toxic by ingestion. A skin irritant. Mutation data reported. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

Check Digit Verification of cas no

The CAS Registry Mumber 135-02-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 5 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 135-02:
(5*1)+(4*3)+(3*5)+(2*0)+(1*2)=34
34 % 10 = 4
So 135-02-4 is a valid CAS Registry Number.
InChI:InChI=1/C8H8O2/c1-10-8-5-3-2-4-7(8)6-9/h2-6H,1H3

135-02-4 Well-known Company Product Price

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  • TCI America

  • (A0479)  o-Anisaldehyde  >98.0%(GC)

  • 135-02-4

  • 25g

  • 180.00CNY

  • Detail
  • TCI America

  • (A0479)  o-Anisaldehyde  >98.0%(GC)

  • 135-02-4

  • 100g

  • 510.00CNY

  • Detail
  • TCI America

  • (A0479)  o-Anisaldehyde  >98.0%(GC)

  • 135-02-4

  • 500g

  • 1,580.00CNY

  • Detail
  • Alfa Aesar

  • (A10770)  2-Methoxybenzaldehyde, 98%   

  • 135-02-4

  • 100g

  • 381.0CNY

  • Detail
  • Alfa Aesar

  • (A10770)  2-Methoxybenzaldehyde, 98%   

  • 135-02-4

  • 500g

  • 1643.0CNY

  • Detail
  • Alfa Aesar

  • (A10770)  2-Methoxybenzaldehyde, 98%   

  • 135-02-4

  • 2500g

  • 7466.0CNY

  • Detail
  • USP

  • (1036948)  o-Anisaldehyde  United States Pharmacopeia (USP) Reference Standard

  • 135-02-4

  • 1036948-3X0.5ML

  • 4,647.24CNY

  • Detail

135-02-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Methoxybenzaldehyde

1.2 Other means of identification

Product number -
Other names Benzaldehyde, 2-methoxy-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:135-02-4 SDS

135-02-4Relevant articles and documents

Synthesis, characterization, crystal structures, Hirshfeld surface analysis, DFT computational studies and catalytic activity of novel oxovanadium and dioxomolybdenum complexes with ONO tridentate Schiff base ligand

Kargar, Hadi,Bazrafshan, Maryam,Fallah-Mehrjardi, Mehdi,Behjatmanesh-Ardakani, Reza,Rudbari, Hadi Amiri,Munawar, Khurram Shahzad,Ashfaq, Muhammad,Tahir, Muhammad Nawaz

, (2021)

For the first time, two new oxovanadium and dioxomolybdenum Schiff base complexes, VOL(OMe) and MoO2L, were synthesized through the reaction of a ONO tridentate Schiff base ligand (H2L) derived from the condensation of 5-bromosalicyl

Silica functionalized Cu(II) catalysed selective oxidation of benzyl alcohols using TEMPO and molecular oxygen as an oxidant

Sharma, Pankaj,Gupta, Monika,Gupta, Rajive,Gupta, Manjulla

, p. 1485 - 1489 (2015)

A general scheme for the oxidation of benzyl alcohols catalyzed by silica functionalized copper (II) has been designed. TEMPO, a free radical, assists this oxidation that was initiated by molecular oxygen which converts it to a primary oxidant. This catalytic combination i.e. SiO2-Cu(II) in presence of TEMPO and oxygen provides excellent results in terms of yields and reaction time. SiO2-Cu(II) was very well characterized by different spectroscopic techniques such as FTIR, XRD, TGA, XPS, EDAX, SEM, TEM and AAS and is recyclable upto five times which makes it economically beneficial. [Figure not available: see fulltext.]

Oxidation of Benzylic and Allylic Alcohols with Cobalt(III) Acetate in Acetic Acid in the Presence and Absence of Sodium Bromide

Hirano, Masao,Morimoto, Takashi,Itoh, Keiko

, p. 3749 - 3751 (1988)

Benzyl alcohol and its o-, m-, and p-substituted derivatives afforded fairly good yields of the corresponding benzaldehydes through a reaction with a Co(III)-NaBr system.With allylic alcohols, this system failed in a selective formation of unsaturated carbonyl compounds.In the latter cases, the products were effectively obtained by using a higher concentration of cobalt(III)acetate in the absence of NaBr.

Acid catalyzed synthesis of 2-(2-aminophenyl)quinazoline-4-amine and reaction with aromatic aldehydes

Marinho, Elina,Proen?a, M. Fernanda

, p. 6138 - 6143 (2016)

The hydrochloride salt of 2-(2-aminophenyl)quinazoline-4-amine, prepared from a quinazolino[3,4-a]quinazoline, was reacted with aromatic aldehydes under conventional heating or microwave irradiation, leading to high yields of tetracyclic dihydroquinazolines.

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

Kargar, Hadi,Fallah-Mehrjardi, Mehdi,Behjatmanesh-Ardakani, Reza,Munawar, Khurram Shahzad,Ashfaq, Muhammad,Tahir, Muhammad Nawaz

, (2021)

A new dioxidomolybdenum(VI) complex has been successfully prepared by the reaction of an ONO donor Schiff base, derived by condensing 4-amino-2-hydroxybenzohydrazide and 3-methoxysalicylaldehyde, with MoO2(acac)2. The structures of s

Oxidation of benzyl alcohols to benzaldehydes in water catalyzed by a Cu(II) complex with a zwitterionic calix[4]arene ligand

Gao, Jun,Ren, Zhi-Gang,Lang, Jian-Ping

, p. 88 - 92 (2015)

Abstract A water-soluble cationic mononuclear copper(II) complex [Cu(II)L(H2O)]I2 (1, H4L = 5,11,17,23-tetrakis(trimethylammonium)-25,26,27,28-tetrahydroxycalix[4]arene) was employed as a catalyst in the oxidation of benzyl alcohols to benzaldehydes in water. In the presence of TEMPO and H2O2, complex 1 exhibited good catalytic activity towards primary benzyl alcohols with a less catalyst loading (0.25 mol%) and a lower temperature (60 °C). The isolated yields of the aldehydes achieved 63-98% within 12 h.

Synthesis, Structure, Biological Evaluation, and Catalysis of Two Pyrazole-Functionalized NHC–RuIIComplexes

Chen, Chao,Ni, Shengliang,Zheng, Qing,Yu, Meifang,Wang, Hangxiang

, p. 616 - 622 (2017)

Two ruthenium complexes, 3a and 3b, bearing pyrazole-functionalized N-heterocyclic carbenes (NHCs) were prepared, and their structures were characterized by X-ray diffraction analysis. Given their promising anticancer potential, we evaluated the cytotoxic

Novel oxovanadium and dioxomolybdenum complexes of tridentate ONO-donor Schiff base ligand: Synthesis, characterization, crystal structures, Hirshfeld surface analysis, DFT computational studies and catalytic activity for the selective oxidation of benzyl

Amiri Rudbari, Hadi,Ashfaq, Muhammad,Behjatmanesh-Ardakani, Reza,Fallah-Mehrjardi, Mehdi,Forootan, Pooran,Kargar, Hadi,Nawaz Tahir, Muhammad,Shahzad Munawar, Khurram

, (2021)

Two new oxovanadium and dioxomolybdenum Schiff base complexes, [VvO(L)(OCH3)(CH3OH)] and [MoVIO2(L)(CH2CH3OH)], were synthesized by treating an ONO-donor type Schiff base ligand

A frank synthesis of alkyl-aryl ethers from 2-halobenzaldehydes and aromatic olefins without transition metal co-catalyst and ligand

Kumar, Balagani Sathish,Negi, Arvind S.

, p. 2340 - 2344 (2015)

An efficient synthesis of alkyl ethers has been developed for o-deactivated aryl halides and 1-halotetralenes. The method shows good regioselectivity towards ortho substituted halides. Alkali metal carbonates (Li2CO3/Na2CO3/K2CO3/Cs2CO3) have been used without a transition metal co-catalyst and ligand. The method is simple, straight-forward and proceeds to afford products in good isolated yields. The method holds potential for future applications in organic synthesis.

Synthesis, characterization and application of γ-MnO2/graphene oxide for the selective aerobic oxidation of benzyl alcohols to corresponding carbonyl compounds

Kadam, Mahesh M.,Dhopte, Kiran B.,Jha, Neetu,Gaikar, Vilas G.,Nemade, Parag R.

, p. 1436 - 1442 (2016)

A facile low temperature approach was used to synthesize γ-MnO2 on the surface of graphene oxide (GO) through a simple wet precipitation method using MnSO4 as a precursor. X-ray diffraction analysis and Raman spectroscopy confirmed the formation of γ-phase MnO2 in the MnO2/GO nanocomposites. Transmission electron microscopy studies showed that γ-MnO2 exists as flower and needle structures in GO with an average size of approximately 15 nm. Inductively coupled plasma atomic emission spectroscopy studies confirmed a 62.5 wt% loading of γ-MnO2 in the GO nanocomposites. The γ-MnO2/GO catalyst shows good activity for the selective aerobic oxidation of benzyl alcohols to corresponding carbonyl compounds even when present in sub-stoichiometric amounts giving 91% yield over 3 h under mild reaction conditions. The catalyst showed high activity even after three cycles indicating good recyclability.

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