614-82-4

Basic information

• Product Name: 2,4-dihydroxyphenylacetic acid
• Synonyms: 2,4-dihydroxyphenylacetic acid;2,4-Dihydroxybenzeneacetic acid;2-(2,4-dihydroxyphenyl)acetic acid;2-(2,4-dihydroxyphenyl)ethanoic acid
• CAS NO: 614-82-4
• Molecular Formula: C₈H₈O₄
• Molecular Weight: 168.14672
• EINECS: 210-397-4
• Mol File: 614-82-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 419 °C at 760 mmHg
• Flash Point: 221.4 °C
• Appearance: /
• Density: 1.478 g/cm³
• Vapor Pressure: 9.04E-08mmHg at 25°C
• Refractive Index: 1.642
• PKA: 4.38±0.10(Predicted)
• CAS DataBase Reference: 2,4-dihydroxyphenylacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-dihydroxyphenylacetic acid(614-82-4)
• EPA Substance Registry System: 2,4-dihydroxyphenylacetic acid(614-82-4)

Safety Data

• Hazardous Substances Data: 614-82-4(Hazardous Substances Data)

Usage

General Description

2,4-dihydroxyphenylacetic acid, also known as dopamine, is a chemical compound that plays a crucial role in the brain and body. It is both a neurotransmitter and a precursor to other important metabolites. In the brain, dopamine functions as a neurotransmitter that helps regulate movement, motivation, and emotional responses. It is also involved in the reward system and has been linked to addiction and mood disorders. Outside of the brain, dopamine acts as a neurohormone that helps regulate blood pressure and kidney function. Overall, 2,4-dihydroxyphenylacetic acid is a vital chemical in the body, with its dysregulation being implicated in various neurological and psychiatric disorders.

InChI:InChI=1/C8H8O4/c9-6-2-1-5(3-8(11)12)7(10)4-6/h1-2,4,9-10H,3H2,(H,11,12)

Synthetic route

2-(2,4-bis(benzyloxy)phenyl)acetic acid (66056-40-4) → (2,4-dihydroxyphenyl)acetic acid (614-82-4)

Conditions	Yield
With ammonium formate; palladium on activated charcoal In N,N-dimethyl-formamide for 0.5h; Ambient temperature;	99%

2-(2-bromo-4-hydroxyphenyl)acetic acid (88491-44-5) → (2,4-dihydroxyphenyl)acetic acid (614-82-4)

Conditions	Yield
With copper 8-hydroxyquinolinate; sodium hydroxide	83%
With bis(8-hydroxyquinolato)copper(II); sodium hydroxide at 110℃; for 6h; Concentration; Temperature; Reagent/catalyst;	81%

3-Bromophenol (591-20-8) → (2,4-dihydroxyphenyl)acetic acid (614-82-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / water / 8 h / 40 °C 2: tin(II) chloride dihdyrate; hydrogenchloride / 3 h / 80 °C 3: bis(8-hydroxyquinolato)copper(II); sodium hydroxide / 6 h / 110 °C View Scheme
Multi-step reaction with 3 steps 1: sodium hydroxide 2: tin(II) chloride dihdyrate; hydrogenchloride / water 3: sodium hydroxide; copper 8-hydroxyquinolinate View Scheme

2-(2-bromo-4-hydroxyphenyl)-2-hydroxyacetic acid → (2,4-dihydroxyphenyl)acetic acid (614-82-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: tin(II) chloride dihdyrate; hydrogenchloride / water 2: sodium hydroxide; copper 8-hydroxyquinolinate View Scheme

(2,4-dihydroxyphenyl)acetic acid (614-82-4) → 4-hydroxysalicylic acid (89-86-1)

Conditions	Yield
With iodine; dimethyl sulfoxide at 120℃; for 28h; Sealed tube; Green chemistry;	83%

4-methoxy-benzaldehyde (123-11-5) + (2,4-dihydroxyphenyl)acetic acid (614-82-4) → 6-hydroxy-3-[(4-methoxyphenyl)methylene]benzo[b]furan-2-one

Conditions	Yield
With acetic anhydride; triethylamine at 110℃; for 6h; Green chemistry;	75%

4-hydroxy-benzaldehyde (123-08-0) + (2,4-dihydroxyphenyl)acetic acid (614-82-4) → 6-hydroxy-3-[(4-hydroxyphenyl)methylene]benzo[b]furan-2-one

Conditions	Yield
With acetic anhydride; triethylamine at 110℃; for 6h; Green chemistry;	75%

3,4-dimethoxy-benzaldehyde (120-14-9) + (2,4-dihydroxyphenyl)acetic acid (614-82-4) → 6-hydroxy-3-[(3,4-dimethoxyphenyl)methylene]benzo[b]furan-2-one

Conditions	Yield
With acetic anhydride; triethylamine at 110℃; for 6h; Green chemistry;	70%

3,4,5-trimethoxy-benzaldehyde (86-81-7) + (2,4-dihydroxyphenyl)acetic acid (614-82-4) → 6-hydroxy-3-[(3,4,5-trimethoxyphenyl)methylene]benzo[b]furan-2-one

Conditions	Yield
With acetic anhydride; triethylamine at 110℃; for 6h; Green chemistry;	68%

3,5-dimethoxybenzaldehdye (7311-34-4) + (2,4-dihydroxyphenyl)acetic acid (614-82-4) → 6-hydroxy-3-[(3,5-dimethoxyphenyl)methylene]benzo[b]furan-2-one

Conditions	Yield
With acetic anhydride; triethylamine at 110℃; for 6h; Green chemistry;	66%

(2,4-dihydroxyphenyl)acetic acid (614-82-4) + 2,4-Dihydroxybenzaldehyde (95-01-2) → 7-hydroxy-3-(2’,4’-dihydroxyphenyl)coumarin

Conditions	Yield
With acetic anhydride; triethylamine at 110℃; for 6h; Green chemistry;	65%
With sodium acetate; acetic anhydride; acetic acid for 24h; Reflux;	49%

(2,4-dihydroxyphenyl)acetic acid (614-82-4) → (2,4-Dihydroxy-3-iodo-phenyl)-acetic acid + (2,4-Dihydroxy-5-iodo-phenyl)-acetic acid + (2,4-Dihydroxy-3,5-diiodo-phenyl)-acetic acid

Conditions	Yield
With sodium acetate buffer; dihydrogen peroxide; potassium iodide; lactoperoxidase for 0.25h; Ambient temperature; incubation, pH=5.6;

(2,4-dihydroxyphenyl)acetic acid (614-82-4) + dicyclohexyl-carbodiimide (538-75-0) → C16H14O7 + 1,3-Dicyclohexylurea (2387-23-7)

Conditions	Yield
In water; ethyl acetate at 20℃; for 3h;

(2,4-dihydroxyphenyl)acetic acid (614-82-4) + 2,4-Dihydroxybenzaldehyde (95-01-2) → coumestrol (479-13-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic anhydride; sodium acetate; acetic acid / 24 h / Reflux 2: copper diacetate / diphenylether / 18 h / 258 °C View Scheme

4-methoxy-benzaldehyde (123-11-5) + (2,4-dihydroxyphenyl)acetic acid (614-82-4) → E-2,4-dihydroxy-4’-methoxystilbene

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; acetic anhydride / 6 h / 110 °C / Green chemistry 2: potassium hydroxide / propylene glycol / 0.5 h / 180 °C / Green chemistry View Scheme

3,4-dimethoxy-benzaldehyde (120-14-9) + (2,4-dihydroxyphenyl)acetic acid (614-82-4) → E-2,4-dihydroxy-3’,4’-dimethoxystilbene

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; acetic anhydride / 6 h / 110 °C / Green chemistry 2: potassium hydroxide / propylene glycol / 0.5 h / 180 °C / Green chemistry View Scheme

3,5-dimethoxybenzaldehdye (7311-34-4) + (2,4-dihydroxyphenyl)acetic acid (614-82-4) → E-2,4-dihydroxy-3’,5’-dimethoxystilbene

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; acetic anhydride / 6 h / 110 °C / Green chemistry 2: potassium hydroxide / propylene glycol / 0.5 h / 180 °C / Green chemistry View Scheme

3,4,5-trimethoxy-benzaldehyde (86-81-7) + (2,4-dihydroxyphenyl)acetic acid (614-82-4) → E-2,4-dihydroxy-3’,4’,5’-trimethoxystilbene

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; acetic anhydride / 6 h / 110 °C / Green chemistry 2: potassium hydroxide / propylene glycol / 0.5 h / 180 °C / Green chemistry View Scheme

4-hydroxy-benzaldehyde (123-08-0) + (2,4-dihydroxyphenyl)acetic acid (614-82-4) → 2',4',4-trihydroxystilbene

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; acetic anhydride / 6 h / 110 °C / Green chemistry 2: potassium hydroxide / propylene glycol / 0.5 h / 180 °C / Green chemistry View Scheme

(2,4-dihydroxyphenyl)acetic acid (614-82-4) + 2,4-Dihydroxybenzaldehyde (95-01-2) → E-2,2’,4,4’-tetrahydroxystilbene

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; acetic anhydride / 6 h / 110 °C / Green chemistry 2: potassium hydroxide / propylene glycol / 0.5 h / 140 °C / Green chemistry View Scheme

(2,4-dihydroxyphenyl)acetic acid (614-82-4) → coumestrol (479-13-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / 6 h / 110 °C 2: sodium hydroxide / water 3: copper diacetate; 1,10-Phenanthroline / dimethyl sulfoxide; water / 18 h / 135 °C / Sealed tube; Green chemistry View Scheme

(2,4-dihydroxyphenyl)acetic acid (614-82-4) → 7-hydroxy-3-(2’,4’-dihydroxyphenyl)coumarin

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / 6 h / 110 °C 2: sodium hydroxide / water View Scheme

acetic anhydride (108-24-7) + (2,4-dihydroxyphenyl)acetic acid (614-82-4) + 2,4-Dihydroxybenzaldehyde (95-01-2) → C21H16O8

Conditions	Yield
With triethylamine at 110℃; for 6h;

Upstream product

• 591-20-8 3-Bromophenol 
• 88491-44-5 2-(2-bromo-4-hydroxyphenyl)acetic acid 
• 66056-40-4 2-(2,4-bis(benzyloxy)phenyl)acetic acid 

Downstream Products

• 89-86-1 4-hydroxysalicylic acid 
• 479-13-0 coumestrol 
• 131391-99-6 3-(2,4-dihydroxyphenyl) coumarin 
• 2387-23-7 1,3-Dicyclohexylurea 

Relevant articles and documents

Copper-catalyzed intramolecular cross dehydrogenative coupling approach to coumestans from 2′-hydroxyl-3-arylcoumarins

A copper-catalyzed intramolecular cross dehydrogenative C-O coupling reaction of 2′-hydroxyl-3-arylcoumarins was developed. This protocol provided a facile and efficient strategy for the construction of natural coumestans and derivatives in moderate to high yields. This transformation exhibited good functional group compatibility and was amenable to substrates with free phenolic hydroxyl groups.

Syntheses and biological activities of joro spider toxin analogs to spidamine and joramine

In order to study the structure-activity relationships of spidamine and joramine found in the venom of Joro spider, Nephila clavata, we attempted to synthesize various analogs. Six analogs were convergently synthesized according to our previous method for the synthesis of spidamine, N-(3- aminopropyl-β-alanyl)-N'-(2,4-dihydroxyphenylacetyl-L-asparaginyl)-1,5- pentanediamine and joramine, N-(3-aminopropyl-β-alanyl)-N'-(4- hydroxyphenylacetyl-L-asparaginyl)-1,5-pentanediamine. The biological activities of the analogs and four intermediates were compared with those of synthetic spidamine and joramine in three bioassay systems, lobster neuromuscular synapse, cockroaches and mosquito larvae. The glutamate receptors in these systems were inhibited by some analogs, and the D- asparagine- or indoleacetyl-containing analogs were found to be strong inhibitors. These compounds have potential application as insecticides.