29866-54-4

Basic information

• Product Name: 2-CHLORO-6-METHOXY-BENZALDEHYDE
• Synonyms: 2-CHLORO-6-METHOXY-BENZALDEHYDE
• CAS NO: 29866-54-4
• Molecular Formula: C₈H₇ClO₂
• Molecular Weight: 170.59
• Mol File: 29866-54-4.mol

Chemical Properties

• Melting Point: 56-58 °C
• Boiling Point: 263.089 °C at 760 mmHg
• Flash Point: 117.142 °C
• Appearance: /
• Density: 1.245 g/cm³
• Vapor Pressure: 0.01mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2-CHLORO-6-METHOXY-BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-6-METHOXY-BENZALDEHYDE(29866-54-4)
• EPA Substance Registry System: 2-CHLORO-6-METHOXY-BENZALDEHYDE(29866-54-4)

Safety Data

• Hazardous Substances Data: 29866-54-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-6-methoxy-benzaldehyde is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its benzaldehyde group provides a versatile platform for the development of new drugs, contributing to the advancement of medicine.
Used in Fragrance Industry:
In the fragrance industry, 2-chloro-6-methoxy-benzaldehyde is used as a base for creating unique and complex scents. Its aromatic properties allow for the formulation of a wide range of fragrances, enhancing the sensory experience in various products.
Used in Specialty Chemicals:
2-Chloro-6-methoxy-benzaldehyde is also utilized in the production of specialty chemicals, where its chemical structure and reactivity are harnessed for specific applications. This includes the development of dyes, pigments, and other chemical products that require its unique properties.

InChI:InChI=1/C8H7ClO2/c1-11-8-4-2-3-7(9)6(8)5-10/h2-5H,1H3

Upstream product

• 67-56-1 methanol 
• 89-98-5 2-chloro-benzaldehyde 
• 54166-96-0 methyl 2-amino-6-methoxybenzoate 
• 936479-46-8 methyl 6-chloro-2-methoxybenzoate 
• 1038726-89-4 2-chloro-6-methoxyphenylmethanol 
• 387-45-1 2-chloro-6-fluorobenzaldehyde 
• 3260-87-5 3-chloro-o-cresol 
• 108-43-0 3-monochlorophenol 
• 135-02-4 ortho-anisaldehyde 
• 3260-88-6 1-chloro-3-methoxy-2-methylbenzene 
• 18362-30-6 2-chloro-6-hydroxybenzaldehyde 
• 74-88-4 methyl iodide 

Downstream Products

• 3260-89-7 2-chloro-6-methoxybenzoic acid 
• 18362-30-6 2-chloro-6-hydroxybenzaldehyde 
• 1439559-61-1 2-(2-chloro-6-methoxy-4-prop-1-ynyl-phenyl)-3-methoxy-5-prop-2-ynyl-cyclopent-2-en-1-one 
• 1439559-68-8 2-(2-chloro-6-methoxy-4-prop-1-ynyl-phenyl)-4-prop-2-ynyl-cyclopentane-1,3-dione 
• 1439559-22-4 C₁₂H₁₁ClO₃ 
• 1439559-28-0 C₁₂H₉ClO₃ 
• 1439559-34-8 C₁₂H₁₁ClO₃ 
• 1439559-16-6 2-(2-chloro-6-methoxy-phenyl)-3-methoxy-cyclopent-2-en-1-one 
• 1439559-40-6 2-[2-chloro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-methoxy-cyclopent-2-en-1-one 
• 1439559-48-4 2-(4-bromo-2-chloro-6-methoxy-phenyl)-3-methoxy-cyclopent-2-en-1-one 
• 1439559-54-2 2-(4-bromo-2-chloro-6-methoxy-phenyl)-3-methoxy-5-prop-2-ynyl-cyclopent-2-en-1-one 
• 1439559-10-0 (2-chloro-6-methoxy-phenyl)-(2-furyl)methanol 
• 72403-03-3 2-methoxy-6-chlorophenol 
• 1154740-80-3 6-chloro-2H-chromene-3(4H)-one 

Relevant articles and documents

Monodentate Transient Directing Group Enabled Pd-Catalyzed Ortho-C-H Methoxylation and Chlorination of Benzaldehydes

We report Pd-catalyzed ortho-C-H methoxylation and chlorination of benzaldehydes by employing monodentate transient directing groups (TDGs) as an alternative strategy to bidentate TDGs. More importantly, a single crystal of benzaldehyde imine ortho-cyclopalladium intermediate was successfully obtained, and its structure was unambiguously determined by X-ray diffraction, which clearly showed that it was a binuclear palladium species bridged by a pyridone ligand. The utility of this approach was further demonstrated through the synthesis of key intermediates of natural products and drugs.

Diverse ortho-C(sp2)-H functionalization of benzaldehydes using transient directing groups

Pd-catalyzed C-H functionalizations promoted by transient directing groups remain largely limited to C-H arylation only. Herein, we report a diverse set of ortho-C(sp2)-H functionalizations of benzaldehyde substrates using the transient directing group strategy. Without installing any auxiliary directing group, Pd(II)-catalyzed C-H arylation, chlorination, bromination, and Ir(III)-catalyzed amidation, could be achieved on benzaldehyde substrates. The transient directing groups formed in situ via imine linkage can override other coordinating functional groups capable of directing C-H activation or catalyst poisoning, significantly expanding the scope for metal-catalyzed C-H functionalization of benzaldehydes. The utility of this approach is demonstrated through multiple applications, including late-stage diversification of a drug analogue.

A Mild meta-Selective C–H Alkylation of Catechol Mono-Ethers

Catechol mono-ethers are an important class of phenols. They are found in a number of pharmaceuticals, flavoring agents, perfumes, and are used for the preparation of numerous drugs. Herein, we report a mild meta-selective C–H alkylation of these phenols, which is enabled by a cascade of oxidative dearomatization – radical addition – rearomatization process. The method is compatible with reactive functional groups on the parent arenol, such as olefins and halides. Primary, secondary, and teriary alkyl groups can be used, the source of which is most commonly an alkylborane. This process is operationally simple, does not require heating and generally proceeds in good yields.

INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION

Compounds of formula (I): wherein R4, R6 and R7 are defined herein, are useful as inhibitors of HIV replication.

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