1466-76-8 Usage
Description
2,6-Dimethoxybenzoic acid is a white to off-white crystalline powder with chemical properties that make it a valuable compound in the synthesis of various organic compounds. It is characterized by the presence of two methoxy groups at the 2nd and 6th positions of the benzoic acid structure, which contribute to its reactivity and potential applications in different industries.
Uses
Used in Pharmaceutical Industry:
2,6-Dimethoxybenzoic acid is used as a key intermediate in the synthesis of indoles and coumarins, which are important classes of organic compounds with significant biological activities. Specifically, it is utilized in the synthesis of Novobiocin (N888500), a potent inhibitor of heat-shock protein 90 (Hsp90). Hsp90 is a molecular chaperone protein that plays a crucial role in the stabilization and activation of various client proteins involved in cell survival, proliferation, and differentiation. Inhibition of Hsp90 has been shown to have therapeutic potential in the treatment of breast cancer by disrupting the function of its client proteins, leading to the suppression of cancer cell growth and survival.
Used in Chemical Synthesis:
2,6-Dimethoxybenzoic acid is also used as a versatile building block in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structural features, such as the presence of methoxy groups and the carboxylic acid functionality, make it a valuable starting material for the development of new molecules with potential applications in various industries.
Flammability and Explosibility
Notclassified
Purification Methods
Crystallise the acid from water or 1,1-dichloroethane (m 187.5-188.5o). [Beilstein 10 H 388, 10 I 185, 10 II 259, 10 III 1401, 10 IV 1456.]
Check Digit Verification of cas no
The CAS Registry Mumber 1466-76-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,4,6 and 6 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 1466-76:
(6*1)+(5*4)+(4*6)+(3*6)+(2*7)+(1*6)=88
88 % 10 = 8
So 1466-76-8 is a valid CAS Registry Number.
InChI:InChI=1/C9H10O4/c1-12-6-4-3-5-7(13-2)8(6)9(10)11/h3-5H,1-2H3,(H,10,11)/p-1
1466-76-8Relevant articles and documents
The gold(I)-catalysed protodecarboxylation mechanism
Dupuy, St??phanie,Crawford, Luke,B??hl, Michael,Nolan, Steven P.
, p. 3399 - 3408 (2015)
A mechanistic study of the gold-catalysed protodecarboxylation is described. Each reaction step has been investigated experimentally and computationally. More specifically, the activation parameters for the decarboxylation step have been determined through kinetic studies. Further experimental studies on the hydrolysis of the arylgold intermediate have revealed that the protodeauration can become competitive with the decarboxylation process at high conversions. This switch in rate-limiting step has been shown to be pKa-dependent. These studies have been supported by DFT calculations and permit a better understanding of which prevalent features of the reaction mechanism account for the decarboxylation process.
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Screttas
, p. 869 (1972)
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Gilman et al.
, p. 667 (1940)
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Metal-Free Dehomologative Oxidation of Arylacetic Acids for the Synthesis of Aryl Carboxylic Acids
Kalmode, Hanuman P.,Vadagaonkar, Kamlesh S.,Shinde, Suresh L.,Chaskar, Atul C.
, p. 3781 - 3786 (2017/04/11)
A novel I2-promoted direct conversion of arylacetic acids into aryl carboxylic acids under metal-free conditions has been described. This remarkable transformation involves decarboxylation followed by an oxidation reaction enabled just by using DMSO as the solvent as well as an oxidant. Notably, aryl carboxylic acids are isolated by simple filtration technique and obtained in good to excellent yields. This protocol is free from chromatographic purification, which makes it applicable for large-scale synthesis.
