2420-16-8

Basic information

• Product Name: 3-Chloro-4-hydroxybenzaldehyde
• Synonyms: Benzaldehyde, 3-chloro-4-hydroxy-;TIMTEC-BB SBB004014;TIMTEC-BB SBB005887;AKOS B028967;3-CHLORO-4-HYDROXYBENZALDEHYDE;3-CHLORO-4-HYROXYBENZALDEHYDE;3-Chloro-4-hydroxybenzaldehyde 98%;3-Chloro-4-hydroxybenzaldehyde, 99+%
• CAS NO: 2420-16-8
• Molecular Formula: C₇H₅ClO₂
• Molecular Weight: 156.57
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Aldehydes;Phenyls & Phenyl-Het;Benzaldehyde;Phenyls & Phenyl-Het;C7;Carbonyl Compounds
• Mol File: 2420-16-8.mol

Chemical Properties

• Melting Point: 145-147 °C(lit.)
• Boiling Point: 150 °C / 14mmHg
• Flash Point: 105.634 °C
• Appearance: white to pink solid, powder or crystals
• Density: 1.2683 (rough estimate)
• Vapor Pressure: 0.00363mmHg at 25°C
• Refractive Index: 1.5812 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 6.30±0.18(Predicted)
• Sensitive: Air Sensitive
• CAS DataBase Reference: 3-Chloro-4-hydroxybenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chloro-4-hydroxybenzaldehyde(2420-16-8)
• EPA Substance Registry System: 3-Chloro-4-hydroxybenzaldehyde(2420-16-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-43-41-37/38-22-20/21/22
• Safety Statements: 26-37/39-36/37/39-36-37
• WGK Germany: 3
• Hazardous Substances Data: 2420-16-8(Hazardous Substances Data)

Usage

Chemical Properties

White solid

InChI:InChI=1/C7H5ClO2/c8-7-3-6(10)2-1-5(7)4-9/h1-4,10H

Upstream product

• 50-00-0 formaldehyd 
• 95-57-8 2-monochlorophenol 
• 302-17-0 chloral hydrate 
• 67-66-3 chloroform 
• 68243-92-5 2,2,2-trichloro-1-(3-chloro-4-hydroxy-phenyl)-ethanol 
• 141805-79-0 3-Chlor-4-hydroxybenzylchlorid 
• 105960-29-0 2-chloro-4-(hydroxymethyl)phenol 
• 507-40-4 tert-butylhypochlorite 
• 123-08-0 4-hydroxy-benzaldehyde 
• 76-03-9 trichloroacetic acid 
• 127-68-4 sodium 3-nitrobenzenesulfonate 
• 100-39-0 benzyl bromide 
• 6640-27-3 2-chloro-p-cresol 
• 100-97-0 hexamethylenetetramine 

Downstream Products

• 105540-95-2 isonicotinic acid-(3-chloro-4-hydroxy-benzylidenehydrazide) 
• 73747-73-6 (3-chloro-4-hydroxy-benzylidene)-malonic acid 
• 52268-43-6 2-ethyl-3t-(3-chloro-4-hydroxy-phenyl)-acrylic acid 
• 105960-29-0 2-chloro-4-(hydroxymethyl)phenol 
• 66422-84-2 4-benzyloxy-3-chlorobenzaldehyde 
• 107149-89-3 N,N'-(3-chloro-4-hydroxy-benzylidene)-bis-propionamide 
• 124685-93-4 (2S,4S)-2-(4-Acetoxy-3-chloro-phenyl)-3-acetyl-5,5-dimethyl-thiazolidine-4-carboxylic acid 
• 124652-13-7 (2R,4S)-2-(3-Chloro-4-hydroxy-phenyl)-5,5-dimethyl-thiazolidine-4-carboxylic acid 
• 124652-13-7 (2S,4S)-2-(3-Chloro-4-hydroxy-phenyl)-5,5-dimethyl-thiazolidine-4-carboxylic acid 
• 1849-76-9 3-bromo-5-chloro-4-hydroxybenzaldehyde 
• 16231-54-2 ethyl [2-chloro-4-formylphenoxy]acetate 
• 124956-02-1 3-Chloro-4-[(2-methoxyethoxy)methoxy]benzaldehyde 
• 81490-64-4 3-chloro-4-hydroxy-5-[(4-hydroxypiperidin-1-yl)methyl]benzaldehyde 
• 108898-23-3 3-chloro-4-(octyloxy)benzaldehyde 

Relevant articles and documents

Activator free, expeditious and eco-friendly chlorination of activated arenes by N-chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI)

N-Chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI) has been explored for the first time as a chlorinating reagent for direct chlorination of various activated arenes and heterocycles without any activator. A comparative in-silico study was performed to determine the electrophilic character for NCBSI and commercially available N-chloro reagents to reveal the reactivity on a theoretical viewpoint. The reagent was prepared by an improved method avoiding the use of hazardous t-butyl hypochlorite. This reagent was proved to be very reactive compared to other N-chloro reagents. The precursor of the reagent N-(phenylsulfonyl)benzene sulfonamide was recovered from aqueous spent, which can be recycled to synthesize NCBSI. The eco-friendly protocol was equally applicable for the synthesis of industrially important chloroxylenol as an antibacterial agent.

Preparation method of 3-methoxy-4-hydroxybenzaldehyde

The invention discloses a preparation method of 3-methoxy-4-hydroxybenzaldehyde, which belongs to the technical field of biochemical technology materials. The method comprises the following specific steps of adding o-chlorophenol, anhydrous aluminum chloride and toluene into a three-neck flask, stirring for dissolving, heating for reflux, then adding diethylamine, continuously refluxing, adding formic anhydride lithium salt, adjusting the PH value, carrying out suction filtration, carrying out reduced pressure distillation, and collecting fractions to obtain 3-chloro-4-hydroxybenzaldehyde, and adding the obtained 3-chloro-4-hydroxybenzaldehyde, anhydrous magnesium chloride and benzene into a three-neck flask, mixing, dissolving, heating, refluxing, dropwise adding a 10% sodium hydroxide solution, uniformly adding sodium methoxide in three batches, cooling to room temperature, adjusting the PH value, carrying out suction filtration, and carrying out reduced pressure distillation to finally obtain the 3-methoxy-4-hydroxybenzaldehyde product. Compared with a traditional method, the synthetic route is not long, the reaction condition is mild, and the yield is high.

Towards the total synthesis of chondrochloren A: Synthesis of the (Z)-enamide fragment

The stereoselective synthesis of the (Z)-enamide fragment of chondrochloren (1) is described. A Buchwald-type coupling between amide 3 and (Z)-bromide 4 was used to generate the required fragment. The employed amide 3 comprising three chiral centers was o

PRODRUGS OF FUSED-BICYCLIC C5aR ANTAGONISTS

The present disclosure provides, inter alia, Compounds of Formulae IA, IB, IC, IIA, IIB and IIC or pharmaceutically acceptable salts thereof that are modulators of the C5a receptor. Also provided are pharmaceutical compositions and methods of use including the treatment of diseases or disorders involving pathologic activation from C5a and non-pharmaceutical applications.

Rate enhancements due to ultrasound in isoquinolinium dichromate and isoquinolinium chlorochromate catalyzed chlorination of aromatic compounds in presence of KHSO4/KCl

Chlorination of aromatic compounds underwent magnificent rate accelerations in isoquinolinium dichromate and isoquinolinium chlorochromate catalyzed chlorination of aromatic hydrocarbons in the presence of KCl and KHSO4. Reaction times reduced highly significantly from 4-5 h in conventional protocol to 30-40 min under sonication, followed by high yields of monochloro derivatives as products with high regioselectivity.

A process for preparing a broad pH fluorescent probe of the organic compound and use thereof (by machine translation)

The present invention discloses a process for the preparation of a wide range of fluorescent probe in the pH of the organic compound, the organic compound can be produced according to the actual need to carry out any proportion of combination, and can be fixed in the hydrophilic high polymer further preparing and detecting water environment acidity and alkalinity of the product. The product can be realized to the pH value of the continuous measuring, thereby greatly improving the efficiency, sensitivity and repeatability. (by machine translation)

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Regioselective C-H chlorination: Towards the sequential difunctionalization of phenol derivatives and late-stage chlorination of bioactive compounds

We have developed a protocol for the auxillary directed C-H chlorination of phenol derivatives using catalytic amounts of palladium acetate that is amenable to the late-stage chlorination of diflufenican and estrone. The 2-pyridine group allows for a highly efficient palladium-catalyzed chlorination and sequential ortho C-H functionalization reaction of phenol derivatives to produce a variety of symmetrical and unsymmetrical 2,4,6-trisubstituted phenols.

Exploration of phenylpropanoic acids as agonists of the free fatty acid receptor 4 (FFA4): Identification of an orally efficacious FFA4 agonist

The long chain free fatty acid receptor 4 (FFA4/GPR120) has recently been recognized as lipid sensor playing important roles in nutrient sensing and inflammation and thus holds potential as a therapeutic target for type 2 diabetes and metabolic syndrome. To explore the effects of stimulating this receptor in animal models of metabolic disease, we initiated work to identify agonists with appropriate pharmacokinetic properties to support progression into in vivo studies. Extensive SAR studies of a series of phenylpropanoic acids led to the identification of compound 29, a FFA4 agonist which lowers plasma glucose in two preclinical models of type 2 diabetes.

Synthesis of salicylaldehydes from phenols via copper-mediated duff reaction

A copper-mediated Duff reaction for ortho-selective formylation of phenols has been developed. In the presence of copper species, significant improvements of yield and ortho-selectivity of the Duff formylation were achieved, which provides an easy access to salicylaldehydes from phenols.