18093-05-5

Basic information

• Product Name: 2-Chloroveratraldehyde
• Synonyms: 2-Chloro-4,5-dimethoxybenzaldehyde;2-chloro-4,5-dimethoxybenzaldehyde(SALTDATA: FREE)
• CAS NO: 18093-05-5
• Molecular Formula: C₉H₉ClO₃
• Molecular Weight: 200.61896
• Mol File: 18093-05-5.mol

Chemical Properties

• Melting Point: 144 °C
• Boiling Point: 303.6 °C at 760 mmHg
• Flash Point: 132.3 °C
• Appearance: /
• Density: 1.245 g/cm³
• Vapor Pressure: 0.000923mmHg at 25°C
• Refractive Index: 1.549
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2-Chloroveratraldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloroveratraldehyde(18093-05-5)
• EPA Substance Registry System: 2-Chloroveratraldehyde(18093-05-5)

Safety Data

• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S36:Wear suitable prot
• HazardClass: IRRITANT
• Hazardous Substances Data: 18093-05-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloroveratraldehyde is used as a building block for the synthesis of pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its unique chemical structure allows for the creation of a wide range of compounds with potential medicinal applications.
Used in Agrochemical Industry:
2-Chloroveratraldehyde is used as a starting material for the preparation of agrochemicals, specifically in the development of new pesticides and other agricultural chemicals. Its potential antifungal and antimicrobial properties make it a valuable component in the formulation of effective crop protection products.
Used in Organic Chemistry Research:
2-Chloroveratraldehyde is used as a subject of study in the field of organic chemistry, particularly in the development of new synthetic methodologies. Its reactivity and potential for forming complex molecules make it an important compound for advancing the understanding of chemical reactions and the creation of novel chemical entities.

InChI:InChI=1/C9H9ClO3/c1-12-8-3-6(5-11)7(10)4-9(8)13-2/h3-5H,1-2H3

Upstream product

• 22608-87-3 2-amino-4,5-dimethoxybenzaldehyde 
• 507-40-4 tert-butylhypochlorite 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 67-66-3 chloroform 
• 7782-50-5 chlorine 
• 37686-56-9 6-chloro-3,4-dihydroxybenzaldehyde 
• 74-88-4 methyl iodide 
• 63190-11-4 (3,4-dimethoxy-6-nitro-benzyliden)-aniline 
• 18268-76-3 6-chlorovaniline 
• 77-78-1 dimethyl sulfate 
• 20357-25-9 6-nitroveratraldehyde 

Downstream Products

• 141648-16-0 6-chloro-3.4-dimethoxy-trans-cinnamic acid 
• 106008-08-6 2-(4',5'-Dimethoxy-2'-chlorostyryl)-4-(δ-diethylamino-α-methylbutylamino)-7-chloroquinazoline 
• 27164-17-6 C₁₀H₁₀ClNO₄ 
• 854660-04-1 6-chloro-3,4-dimethoxy-2-nitro-benzaldehyde 
• 1372790-79-8 4'-fluoro-4,5-dimethoxy-3'-methyl-2-vinylbiphenyl 
• 1372790-72-1 4'-fluoro-4,5-dimethoxy-2-vinylbiphenyl 
• 1372790-73-2 5-(4,5-dimethoxy-2-vinyl phenyl)benzo[d][1,3]-dioxole 
• 1033196-50-7 1-chloro-4,5-dimethoxy-2-vinylbenzene 
• 41001-78-9 8,9-dimethoxylphenanthridine 
• 1186033-47-5 C₁₁H₁₄O₃S 
• 89938-55-6 2-chloro-4-methoxy-5-hydroxybenzaldehyde 
• 18268-76-3 6-chlorovaniline 
• 949591-99-5 N-{4-[(4-aminocyclohexyl)methyl]cyclohexyl}-N-(2-chloro-4,5-dimethoxybenzyl)-4-(1H-indol-3-yl)butanamide trifluoroacetic acid salt 
• 949592-01-2 N-{4-[(4-aminocyclohexyl)methyl]cyclohexyl}-N-(2-chloro-4,5-dimethoxybenzyl)-4-[2-(4-hydroxybenzyl)-1H-indol-3-yl]butanamide trifluoroacetic acid salt 

Relevant articles and documents

Structure of 4-(2-chloro-4,5-dimethoxybenzylidene)-2-methyl-5-oxazolone. X-ray and NMR study

The azlactone of 6-chloroveratraldehyde 3 (4-(2-chloro-4,5-dimethoxybenzylidene)-2-methyl-5-oxazolone) was synthesized from 6-chloroveratraldehyde 2 and its structure investigated using X-ray crystallographic and nuclear magnetic resonance methods. Compound 3 crystallized in the P21/c (#14) space group (Z = 4) with cell dimensions a = 9.148(2), b = 22.938(2), c = 6.707(1) A, and β = 111.50(2)°. The X-ray study shows that azlactone 3 exists as the Z-isomer and crystallizes as a planar structure, i.e., both the phenyl and azlactone ring systems, as well as the functional groups attached to them, lie in the same plane. The 1H and 13C NMR spectral values also support the formation of the Z-isomer only, during the synthesis of 4-(2-chloro-4,5-dimethoxybenzylidene)-2-methyl-5-oxazolone.

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 straightforward and versatile protocol for the direct conversion of benzylic azides to ketones and aldehydes

The synthesis of carbonyl compounds from benzylic azides through benzylideneamides is described for the first time. NaH-mediated activation of benzyl azides allows a rapid water-promoted oxidation under a facile protocol with good yields.

PYRAZOLO-HETEROARYL COMPOUNDS USEFUL TO TREAT TNF-ALPHA AND IL-1 MEDIATED DISEASES

A compound of formula (I) wherein the groups R1-R4, X and Y are as defined in the specification, useful to treat TNF-Alpha and IL-1 mediated diseases.

Comparative α- and β-adrenoceptor activity of 2- and 6-ring-chlorinated noradrenaline analogues

The α- and β-adrenoceptor activity of the 2- and 6-ring-chlorinated analogues of noradrenaline (norepinephrine) were evaluated in vitro. The 2-chloro-substituted analogue exhibits a far greater affinity for β1-chronotropic receptors than the 6-chloro-substituted analogue, whereas no significant differences are apparent for their α-adrenergic affinities.