37470-46-5

Basic information

• Product Name: 4-HYDROXY-3-IODOBENZOIC ACID
• Synonyms: BUTTPARK 22\07-100;3-IODO-4-HYDROXYBENZOIC ACID;4-HYDROXY-3-IODOBENZOIC ACID;2-Iodo-4-carboxyphenol;4-Carboxy-2-iodophenol
• CAS NO: 37470-46-5
• Molecular Formula: C₇H₅IO₃
• Molecular Weight: 264.02
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 37470-46-5.mol

Chemical Properties

• Melting Point: 172-175℃
• Boiling Point: 330 °C at 760 mmHg
• Flash Point: 153.4 °C
• Appearance: /
• Density: 2.155
• Vapor Pressure: 6.86E-05mmHg at 25°C
• Refractive Index: 1.712
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 4-HYDROXY-3-IODOBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-3-IODOBENZOIC ACID(37470-46-5)
• EPA Substance Registry System: 4-HYDROXY-3-IODOBENZOIC ACID(37470-46-5)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 37470-46-5(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
4-Hydroxy-3-iodobenzoic acid is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for selective reactions and transformations, making it a valuable building block for the development of new molecules with potential applications in various fields.
Used in Pharmaceutical Industry:
4-Hydroxy-3-iodobenzoic acid is used as a precursor in the synthesis of pharmaceutical compounds. Its ability to undergo enantioselective cross-electrophile aryl-alkenylation of unactivated alkenes enables the creation of chiral molecules with potential therapeutic applications. This process is crucial for the development of enantiomerically pure drugs, which can have improved efficacy and reduced side effects compared to their racemic counterparts.
Used in Enantioselective Synthesis:
4-Hydroxy-3-iodobenzoic acid is used as a reactant in enantioselective cross-electrophile aryl-alkenylation reactions. This process allows for the selective formation of one enantiomer over the other, which is essential for the production of enantiomerically pure compounds. Enantioselective synthesis is particularly important in the pharmaceutical industry, as the different enantiomers of a drug can have different biological activities and side effect profiles.

InChI:InChI=1/C7H5IO3/c8-5-3-4(7(10)11)1-2-6(5)9/h1-3,9H,(H,10,11)

Upstream product

• 618-76-8 3,5-diiodo-4-hydroxybenzoic acid 
• 99-96-7 4-hydroxy-benzoic acid 
• 1571-72-8 3-amino-4-hydroxybenzoic acid 
• 7732-18-5 water 
• 64-17-5 ethanol 
• 7553-56-2 iodine 

Downstream Products

• 15126-06-4 methyl 3-iodo-4-hydroxybenzoate 
• 475650-18-1 1-[1-(4-hydroxy-3-iodo-benzoyl)-piperidin-4-yl]-1,4-dihydro-benzo[d][1,3]oxazin-2-one 
• 35387-93-0 3-iodo-4-methoxy-benzoic acid methyl ester 
• 609-23-4 2,4,6-Triiodophenol 
• 41072-98-4 3.5-Diiod-4-acetoxybenzoesaeure 
• 951288-65-6 triethylammonium 3-diphenylphosphine-4-hydroxybenzoate 
• 15126-09-7 butyl 3-iodo-4-hydroxybenzoate 
• 1104641-57-7 3-benzyl-3-methyl-2,3-dihydro-benzofuran-6-carboxylic acid 
• 1104641-56-6 3-benzyl-3-methyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester 
• 1104641-58-8 4-iodo-3-(2-methyl-allyl oxy)-benzoic acid methyl ester 
• 1131614-23-7 4-difluoromethoxy-3-iodo-benzoic acid methyl ester 
• 1311175-57-1 tert-butyl 4-hydroxy-3-iodobenzoate 
• 1311175-63-9 tert-butyl 4-hydroxy-3-(1-hydroxy-2,2-dimethylcyclopentyl)benzoate 
• 25804-49-3 tert-butyl 4-hydroxybenzoate 

Relevant articles and documents

Active Site Binding Is Not Sufficient for Reductive Deiodination by Iodotyrosine Deiodinase

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Pd-Catalyzed ipso, meta-Dimethylation of ortho-Substituted Iodoarenes via a Base-Controlled C-H Activation Cascade with Dimethyl Carbonate as the Methyl Source

A methyl group can have a profound impact on the pharmacological properties of organic molecules. Hence, developing methylation methods and methylating reagents is essential in medicinal chemistry. We report a palladium-catalyzed dimethylation reaction of ortho-substituted iodoarenes using dimethyl carbonate as a methyl source. In the presence of K2CO3 as a base, iodoarenes are dimethylated at the ipso- and meta-positions of the iodo group, which represents a novel strategy for meta-C-H methylation. With KOAc as the base, subsequent oxidative C(sp3)-H/C(sp3)-H coupling occurs; in this case, the overall transformation achieves triple C-H activation to form three new C-C bonds. These reactions allow expedient access to 2,6-dimethylated phenols, 2,3-dihydrobenzofurans, and indanes, which are ubiquitous structural motifs and essential synthetic intermediates of biologically and pharmacologically active compounds.

Imidazole-containing condensed tricyclic compound and application thereof

The invention discloses an imidazole-containing condensed tricyclic compound adopting the structure as shown in the formula (I) or pharmaceutically acceptable salts, stereisomers or prodrug molecules thereof. The imidazole-containing condensed tricyclic compound has the IDO1 activity regulation function, can enhance T-cell activation through blocking immune checkpoints IDO1, is used for treating IDO1-mediated immunosuppression, and therefore, can become an effective medicine for treating malignant tumors. When used together with checkpoint protein anti-body drugs or other anti-cancer drugs, the imidazole-containing condensed tricyclic compound can enhance the anti-cancer effect. Meanwhile, the imidazole-containing condensed tricyclic compound has the potential of effectively treating IDO1 abnormity related immunosuppressive diseases and has a high application value.

CuLi2Cl4 catalysed cross-coupling strategy for the formal synthesis of the diterpenoid (+)-subersic acid from (?)-sclareol

A CuLi2Cl4-catalysed regioselective cross-coupling is used in a key step leading to the concise synthesis of (+)-subersic acid with an overall yield of 25.7% from commercially available (-)-sclareol. The coupled product 15-(2-methoxy-5-carbomethoxy)phenyl-labda-8(9),13Ediene was obtained in 62% yield under CuLi2Cl4 conditions starting from 2-iodo-4-carbomethoxyanisole and 15-acetoxy-labda-8(9),13Ediene. These were derived from 4-hydroxybenzoic acid and (-)-sclareol respectively. The 15-(2-methoxy-5-carbomethoxy)phenyl-labda- 8(9),13E-diene was easily transformed into (+)-subersic acid by demethylation of the phenol ether and ester. This cross-coupling strategy showed a good functional group tolerance and various (+)-subersic acid derivatives were obtained in moderate yields.

Heterocyclic modulators of cannabinoid receptors

Heterocyclic compounds which modulate cannabinoid receptors are presented. Pharmaceutical compositions containing these compounds, methods of using these compounds as modulators of cannabinoid receptors and processes for synthesizing these compounds are a

An efficient synthesis of (+)-subersic acid

This paper describes a concise and practical route to (+)-subersic acid from naturally occurring (-)-Sclareol in 7 steps. The key step of this route relied on the cross coupling of the diterpene with the arene fragment using the arylation of allylic acetate followed by β-acetoxy elimination type Heck reaction. A seven-step synthetic route was developed to synthesize (+)-subersic acid from (-)-Sclareol. The cross coupling of the diterpene with the arene fragment using the arylation of allylic acetate followed by β-acetoxy elimination type Heck reaction was acted as the key reaction.

NEUROPROTECTIVE CB2 RECEPTOR AGONISTS

A method of treating or preventing a neuroinflammatory and/or neurodegenerative disease in a subject by administering a pharmaceutically effective amount of a CB2 receptor agonist is described. The CB2 receptor agonist can be a compo

PROCESS FOR PRODUCTION OF PHENOL DERIVATIVES SUBSTITUTED WITH IODINE AT ORTHO POSITION

A process in which a phenol derivative is iodinated to produce a 2-iodophenol or 2,6-diiodophenol derivative substituted with iodine at an ortho position thereof is provided, which does not require any step of recovery of iodine but can produce it at low cost, in high yield and with high quality. A phenol derivative is mixed with a pyridine and hydrogen peroxide or iodic acid as an oxidizing agent, and reacted with molecular iodine. As a result, iodination can be performed very efficiently with iodine in an amount close to the theoretical amount relative to the phenol derivative, and the 2-iodophenol or 2,6-diiodophenol derivative can be obtained in high yield and with high quality.

A mild and simple iodination of phenols with trichloroisocyanuric acid/I2/wet SiO2 system

Molecular iodine in the presence of trichloroisocyanuric acid and wet sio2 has been utilized efficiently for iodination of phenols under mild reaction conditions.

S1P RECEPTORS MODULATORS

The invention relates to novel compounds that have S1P receptor modulating activity and, preferably, apoptotic activity and/or anti proliferative activity against cancer cells and other cell types. Further, the invention relates to a pharmaceutical comprising at least one compound of the invention for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression, for example, cancer. A further aspect of the invention relates to the use of a pharmaceutical comprising at least one compound of the invention for the manufacture of a medicament for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression such as cancer.