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ETHYL 3-METHYLBENZOYLFORMATE, also known as ethyl 3-methylbenzoylformate, is a colorless to pale yellow liquid chemical compound with the molecular formula C11H12O3. It possesses a fruity odor and is commonly utilized as a flavoring agent in the food and beverage industry. Additionally, it finds applications in the synthesis of other organic compounds and as a fragrance in cosmetic and personal care products. With its low toxicity and general safety for use in food and consumer products when following good manufacturing practices, it is a valuable component in various industries.

66644-68-6

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66644-68-6 Usage

Uses

Used in Food and Beverage Industry:
ETHYL 3-METHYLBENZOYLFORMATE is used as a flavoring agent for its fruity odor, enhancing the taste and aroma of various food and drink products.
Used in Cosmetic and Personal Care Products:
ETHYL 3-METHYLBENZOYLFORMATE is used as a fragrance component in cosmetic and personal care products, providing a pleasant scent and improving the sensory experience for users.
Used in Organic Synthesis:
ETHYL 3-METHYLBENZOYLFORMATE is used as a key intermediate in the synthesis of other organic compounds, contributing to the development of new chemical products and materials.
It is important to handle and store ETHYL 3-METHYLBENZOYLFORMATE carefully to avoid exposure and potential hazards, ensuring the safety and quality of the final products in which it is used.

Check Digit Verification of cas no

The CAS Registry Mumber 66644-68-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,6,6,4 and 4 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 66644-68:
(7*6)+(6*6)+(5*6)+(4*4)+(3*4)+(2*6)+(1*8)=156
156 % 10 = 6
So 66644-68-6 is a valid CAS Registry Number.
InChI:InChI=1/C11H12O3/c1-3-14-11(13)10(12)9-6-4-5-8(2)7-9/h4-7H,3H2,1-2H3

66644-68-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name ethyl 2-(3-methylphenyl)-2-oxoacetate

1.2 Other means of identification

Product number -
Other names ethyl 3-methylphenylglyoxylate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:66644-68-6 SDS

66644-68-6Relevant academic research and scientific papers

Electrochemical two-electron oxygen reduction reaction (ORR) induced aerobic oxidation of α-diazoesters

Chen, Liang,Gao, Meng,Lu, Cuifen,Ma, Chao,Ruan, Mengyao,Wen, Ziyang,Yang, Fan,Yang, Guichun

, p. 2168 - 2171 (2022/02/17)

Electrochemical oxygen reduction reaction (ORR) is a powerful tool for introducing oxygen functional groups in synthetic chemistry. However, compared with the well-developed one-electron oxygen reduction process, the applications of two-electron oxygen re

General Synthesis of Chiral α,α-Diaryl Carboxamides by Enantioselective Palladium-Catalyzed Cross-Coupling

Li, Bowen,Aliyu, Muinat A.,Gao, Zhenhua,Li, Tiejun,Dong, Wei,Li, Junchen,Shi, Enxue,Tang, Wenjun

supporting information, p. 4974 - 4978 (2020/07/03)

A general synthesis of chiral α,α-diaryl carboxamides is developed by enantioselective cross-coupling between 2-bromo-2-aryl carboxamides and arylboronic acids, leading to a series of chiral α,α-diaryl carboxamides with various electronic properties and functionalities in moderate to excellent enantioselectivities and yields. The employment of a sterically bulky chiral P,P═O ligand L2 is critical for the reactivity and selectivity. This protocol is applied to an efficient asymmetric synthesis of a key intermediate of dopamine receptor agonist SKF 38393.

Controllable chemoselectivity in the coupling of bromoalkynes with alcohols under visible-light irradiation without additives: Synthesis of propargyl alcohols and α-ketoesters

Ni, Ke,Meng, Ling-Guo,Ruan, Hongjie,Wang, Lei

supporting information, p. 8438 - 8441 (2019/07/22)

The chemoselectivity of visible-light-induced coupling reactions of bromoalkynes with alcohols can be controlled by simple changes to the reaction atmosphere (N2 or O2). A N2 atmosphere favours propargyl alcohols via a direct C-C coupling process, whereas an O2 atmosphere results in the generation of α-ketoesters through the oxidative CC/C-O coupling pathway.

Ambient and aerobic carbon-carbon bond cleavage toward α-ketoester synthesis by transition-metal-free photocatalysis

Yu, Qing,Zhang, Yating,Wan, Jie-Ping

supporting information, p. 3436 - 3441 (2019/06/24)

The α-oxoesterification of the CC double bond in readily available enaminones enabling efficient synthesis of α-ketoesters is developed. The reactions showing general tolerance to the reactions of primary and secondary alcohols proceed well under air via Rose Bengal (RB)-based photocatalysis. Particularly, this mild synthetic method has been discovered to tolerate various polyhydroxylated substrates such as phenolic alcohol, diols and triols with an excellent selectivity of mono-oxoesterification. What is more noteworthy is that α-ketoester functionalized 16-dehydropregnenolone acetate resulting from the elaboration on a natural product has been obtained practically.

COMPOUNDS HAVING MUSCARINIC RECEPTOR ANTAGONIST AND BETA2 ADRENERGIC RECEPTOR AGONIST ACTIVITY

-

Paragraph 0398, (2016/09/12)

Compounds of formula I, defined herein, act both as muscarinic receptor antagonists and beta2 adrenergic receptor agonists and are useful for treating broncho-obstructive and inflammatory diseases.

Chiral Frustrated Lewis Pairs Catalyzed Highly Enantioselective Hydrosilylations of 1,2-Dicarbonyl Compounds

Ren, Xiaoyu,Du, Haifeng

supporting information, p. 810 - 813 (2016/02/09)

A highly enantioselective hydrosilylation of 1,2-dicarbonyl compounds was successfully realized for the first time utilizing the combination of tricyclohexylphosphine and chiral alkenylborane derived in situ from diyne as a frustrated Lewis pair catalyst. A variety of optically active α-hydroxy ketones and esters were obtained in 52-98% yields with 86-99% ee's.

Novel Synthesis of α-Keto Esters and Amides by an sp3 C-H Oxidation of Nitromethyl Aryl Ketones Promoted by Ion-Supported (Diacetoxyiodo)benzene

Jiang, Xiaoying,Gan, Bing,Liu, Jiwei,Xie, Yuanyuan

supporting information, p. 2737 - 2741 (2016/11/25)

A simple and efficient method is described for the preparation of α-keto esters or amides from nitromethyl aryl ketones. In the presence of nucleophiles (alcohols or amines), the ion-supported (di-acetoxyiodo)benzene-promoted sp3 C-H oxidation of nitromethyl aryl ketones proceeded efficiently under mild conditions to give the corresponding α-keto esters and amides in moderate to good yields. This is the first reported use of (diacetoxyiodo)benzene in the synthesis of α-keto esters and amides. The reaction is ecofriendly and has the -advantages of mild conditions, short reaction times, and a recyclable reagent.

Copper(II)-Catalyzed Benzylic C(sp3)-H Aerobic Oxidation of (Hetero)Aryl Acetimidates: Synthesis of Aryl-α-ketoesters

Kumar, Yogesh,Jaiswal, Yogesh,Kumar, Amit

, p. 12247 - 12257 (2016/12/23)

A straightforward method is developed in this paper for the synthesis of α-ketoesters through copper-catalyzed aerobic oxidation of (hetero)aryl acetimidates using molecular oxygen as a sustainable oxidant. The reaction represents the first example of the direct synthesis of aryl-α-ketoesters from arylacetimidates through the aerobic oxidation of a benzylic C(sp3)-H (CO) bond in moderate to good yield. This transformation occurs under mild reaction conditions with a wide range of substrates and utilizes a readily available oxidant and catalyst. The synthetic utility of this transformation is demonstrated through scaled-up synthesis. A plausible reaction mechanism is also proposed.

A novel method for synthesis of α-keto esters with phenyliodine(III) diacetate

Xie, Yuanyuan,Liu, Jiwei,Huang, Yingyi,Yao, Lixia

supporting information, p. 3793 - 3795 (2015/06/08)

A rapid and efficient synthesis of α-keto esters from β-ketonitriles using phenyliodine(III) diacetate is reported. This protocol gave α-keto esters in good yields. This is the first time to report the application of hypervalent iodine(III) reagents in the synthesis of α-keto esters. A plausible reaction mechanism is proposed.

Cationic Ir/Me-BIPAM-catalyzed asymmetric intramolecular direct hydroarylation of α-ketoamides

Shirai, Tomohiko,Ito, Hajime,Yamamoto, Yasunori

supporting information, p. 2658 - 2661 (2014/03/21)

Asymmetric intramolecular direct hydroarylation of α-ketoamides gives various types of optically active 3-substituted 3-hydroxy-2-oxindoles in high yields with complete regioselectivity and high enantioselectivities (84-98 % ee). This is realized by the use of the cationic iridium complex [Ir(cod) 2](BArF4) and the chiral O-linked bidentate phosphoramidite (R,R)-Me-BIPAM. Carbon's got a brand new bond: Asymmetric intramolecular direct hydroarylation of α-ketoamides gives various optically active 3-substituted 3-hydroxy-2-oxindoles in high yields with complete regioselectivity and high enantioselectivities. This is realized by the use of an asymmetric cationic iridium complex formed in situ (see Scheme).

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