201214-53-1

Basic information

• Product Name: methyl 4-acetamido-5-iodo-2-methoxybenzoate
• Synonyms: methyl 4-acetamido-5-iodo-2-methoxybenzoate
• CAS NO: 201214-53-1
• Molecular Formula: C₁₁H₁₂INO₄
• Molecular Weight: 349.12175
• EINECS: -0
• Mol File: 201214-53-1.mol

Chemical Properties

• Boiling Point: 474.802°C at 760 mmHg
• Flash Point: 240.952°C
• Appearance: /
• Density: 1.691g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.613
• Storage Temp.: 2-8°C(protect from light)
• PKA: 13.30±0.70(Predicted)
• CAS DataBase Reference: methyl 4-acetamido-5-iodo-2-methoxybenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-acetamido-5-iodo-2-methoxybenzoate(201214-53-1)
• EPA Substance Registry System: methyl 4-acetamido-5-iodo-2-methoxybenzoate(201214-53-1)

Safety Data

• Hazardous Substances Data: 201214-53-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Methyl 4-acetamido-5-iodo-2-methoxybenzoate is used as a building block in organic synthesis for the creation of various biologically active compounds. Its unique structure allows for the development of new molecules with potential applications in different fields.
Used in Pharmaceutical Research:
In pharmaceutical research, methyl 4-acetamido-5-iodo-2-methoxybenzoate is used as a precursor for the synthesis of drug candidates. Its iodinated and functionalized structure can be further modified to yield compounds with specific therapeutic properties.
Used in Chemical Production:
Methyl 4-acetamido-5-iodo-2-methoxybenzoate is used in the chemical production industry as an intermediate for the synthesis of other complex organic compounds. Its versatility in chemical reactions makes it a valuable component in the production process.
It is important to handle this chemical with care and follow proper safety protocols, as it may pose hazards if not used and stored appropriately.

InChI:InChI=1/C11H12INO4/c1-6(14)13-9-5-10(16-2)7(4-8(9)12)11(15)17-3/h4-5H,1-3H3,(H,13,14)

Upstream product

• 4093-29-2 methyl 4-(acetylamino)-o-anisate 
• 27492-84-8 Methyl 4-amino-2-methoxybenzoate 
• 4136-97-4 methyl 4-aminosalicylate 
• 4093-28-1 methyl 4-acetamido-2-hydroxybenzoate 
• 77-78-1 dimethyl sulfate 
• 201214-52-0 4-Acetylamino-2-hydroxy-5-iodo-benzoic acid methyl ester 
• 65-49-6 4-Aminosalicylic acid 

Downstream Products

• 155928-39-5 4-amino-5-iodo-2-methoxybenzoic acid 
• 201214-54-2 4-Acetylamino-N-(S)-1-aza-bicyclo[2.2.2]oct-3-yl-5-iodo-2-methoxy-benzamide 
• 151334-49-5 4-Amino-N-(S)-1-aza-bicyclo[2.2.2]oct-3-yl-2-methoxy-benzamide 
• 201214-55-3 [125I]-(3S)-Iodozacopride 
• 947263-60-7 4-acetamido-N-(4-(N-tert-butoxycarbonyl-N-butylamino)butyl)-5-iodo-2-methoxybenzamide 
• 176849-94-8 4-acetamido-5-iodo-2-methoxybenzoic acid 

Relevant articles and documents

Synthesis and evaluation of novel radioiodinated benzamides for malignant melanoma

The imaging potential of a series of [123I]benzamides was studied in mice bearing B16F0 melanoma tumors. Compound [123I]25 exhibited tumor uptake >8 %ID/g at 1 h, while that of [123I]14d and [123I]25 reached a maximum of 9-12 %ID/g at 6 h. Standardized uptake values of [123I]14d were higher than 100 between 24 and 72 h after injection. In haloperidol treated animals, the tumor uptake of [ 123I]14d was not significantly different to controls, while significant reduction of [123I]25 uptake was observed, supporting that [123I]14d uptake relates to melanin interaction, whereas part of the mechanism of [123I]25 uptake is related to its σ1-receptor affinity. Benzamides 14d and 25, which display rapid and high tumor uptake, appear to be promising imaging agents for melanoma detection, while 14d, which displays a long lasting and high melanoma/nontarget ratio, is more suitable for evaluation as a potential radiotherapeutic.

Synthesis and radiolabeling of (S)-4-amino-5-iodo-2-methoxy-N (1- azabicyclo[2.2.2]oct-3-yl)benzamide, the Active enantiomer of [125i]iodozacopride, and re-evaluation of its 5-HT3 receptor affinity

We report an improved synthesis of unlabeled (S)-iodozacopride, the radiolabeling of (S)-[125I]iodozacopride via deschloro-(S)-zacopride, and a re-evaluation of its affinity for the 5-HT3 receptor. Unlabeled (S)- iodozacopride was prepared in seven steps from 4-aminosalicylic acid via alkaline hydrolysis of its 4-acetamide derivative. Catalytic hydrogenation of (S)-iodozacopride gave deschloro-(S)-zacopride, identical to that obtained from (S)-3-amino-quinuclidine and 4-amino-2-metihoxybenzoic acid via its corresponding 1-imidazole derivative. Radioiodination to produce (S)- [125I]iodozacopride was accomplished by treatment of deschloro-(S)- zacopride with 5mCi sodium 125iodide and chloramine-T in hydrochloric acid. Purification of the reaction products using an HPLC system capable of detecting chlorinated side-products revealed a mixture of 2.1 mCi (1.3nmol) (S)-[125I]iodozacopride and (S)-zacopride (1.5 nmol). Saturation analysis of the binding of the purified (S)-[125I]iodozacopride to whole rat brain homogenates gave an estimated K(D) of 1.10±0.07 nM. As anticipated, this is approximately haft the K(D) reported for binding of racemic [125I]iodozacopride, and differs from the previously reported value by an order of magnitude. Analysis of the apparent binding affinity of a 1: 1 mixture of (S)-[125I]iodozacopride and (S)-zacopride suggests that the previous result may have been confounded by contamination of the product with unlabeled (S)-zacopride. Competition analysis of the displacement of (S)- [125I]iodozacopride binding by unlabeled (S)-iodozacopride and (S)- zacopride gave K(i) values of 0.95 and 0.21 nM, respectively.