3-Methylsalicylic acid

Last updated
3-Methylsalicylic acid
3-Mesalacid.png
Names
Preferred IUPAC name
2-Hydroxy-3-methylbenzoic acid
Other names
2,3-Cresotic acid
o-Cresotinic acid
2-Hydroxy-m-toluic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.340 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-473-8
KEGG
PubChem CID
UNII
  • InChI=1S/C8H8O3/c1-5-3-2-4-6(7(5)9)8(10)11/h2-4,9H,1H3,(H,10,11)
    Key: WHSXTWFYRGOBGO-UHFFFAOYSA-N
  • CC1=CC=CC(=C1O)C(=O)O
Properties
C8H8O3
Molar mass 152.149 g·mol−1
Appearancewhite solid
Melting point 165.5 °C (329.9 °F; 438.6 K)
Hazards
GHS pictograms GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
GHS Signal word Danger
H302, H315, H318, H335
P261, P264, P270, P271, P280, P301+312, P302+352, P304+340, P305+351+338, P310, P312, P321, P330, P332+313, P362, P403+233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

3-Methylsalicylic acid is an organic compound with the formula CH3C6H3(CO2H)(OH). It is a white solid that is soluble in basic water and in polar organic solvents. At neutral pH, the acid exists as 3-methylsalicylate Its functional groups include a carboxylic acid and a phenol group. It is one of four isomers of methylsalicylic acid.

It can be produced by carboxylation of o-cresol. [1]

See also

Related Research Articles

Benzoic acid Chemical compound

Benzoic acid is a white (or colorless) solid with the formula C6H5CO2H. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, which was for a long time its only source. Benzoic acid occurs naturally in many plants and serves as an intermediate in the biosynthesis of many secondary metabolites. Salts of benzoic acid are used as food preservatives. Benzoic acid is an important precursor for the industrial synthesis of many other organic substances. The salts and esters of benzoic acid are known as benzoates.

Phenols

In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups (—OH) bonded directly to an aromatic hydrocarbon group. The simplest is phenol, C
6
H
5
OH
. Phenolic compounds are classified as simple phenols or polyphenols based on the number of phenol units in the molecule.

Phenol Chemical compound

Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group (−C6H5) bonded to a hydroxy group (−OH). Mildly acidic, it requires careful handling because it can cause chemical burns.

Salicylic acid Chemical compound

Salicylic acid is a lipophilic monohydroxybenzoic acid, a type of phenolic acid, and a beta hydroxy acid (BHA). This colorless crystalline organic acid is widely used in organic synthesis, and functions as a plant hormone. It is derived from the metabolism of salicin.

Phenyl group

In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6H5. Phenyl groups are closely related to benzene and can be viewed as a benzene ring, minus a hydrogen, which may be replaced by some other element or compound to serve as a functional group. Phenyl groups have six carbon atoms bonded together in a hexagonal planar ring, five of which are bonded to individual hydrogen atoms, with the remaining carbon bonded to a substituent. Phenyl groups are commonplace in organic chemistry. Although often depicted with alternating double and single bonds, phenyl groups are chemically aromatic and have equal bond lengths between carbon atoms in the ring.

The cumene process is an industrial process for synthesizing phenol and acetone from benzene and propylene. The term stems from cumene, the intermediate material during the process. It was invented by R. Ūdris and P. Sergeyev in 1942 (USSR)., and independently by Heinrich Hock in 1944

Tosyl group

A toluenesulfonyl (shortened tosyl, abbreviated Ts or Tos) group, H3CC6H4SO2, is a univalent organic group that consists of a tolyl group, H3CC6H4, joined to a sulfonyl group, SO2, with the open valence on sulfur. This group is usually derived from the compound tosyl chloride, H3CC6H4SO2Cl (abbreviated TsCl), which forms esters and amides of toluenesulfonic acid, H3CC6H4SO2OH (abbreviated TsOH). The para orientation illustrated (p-toluenesulfonyl) is most common, and by convention tosyl without a prefix refers to the p-toluenesulfonyl group.

Enols, or more formally, alkenols, are a type of reactive structure or intermediate in organic chemistry that is represented as an alkene (olefin) with a hydroxyl group attached to one end of the alkene double bond. The terms enol and alkenol are portmanteaus deriving from "-ene"/"alkene" and the "-ol" suffix indicating the hydroxyl group of alcohols, dropping the terminal "-e" of the first term. Generation of enols often involves removal of a hydrogen adjacent (α-) to the carbonyl group—i.e., deprotonation, its removal as a proton, H+. When this proton is not returned at the end of the stepwise process, the result is an anion termed an enolate (see images at right). The enolate structures shown are schematic; a more modern representation considers the molecular orbitals that are formed and occupied by electrons in the enolate. Similarly, generation of the enol often is accompanied by "trapping" or masking of the hydroxy group as an ether, such as a silyl enol ether.

Anisole Methoxybenzene

Anisole, or methoxybenzene, is an organic compound with the formula CH3OC6H5. It is a colorless liquid with a smell reminiscent of anise seed, and in fact many of its derivatives are found in natural and artificial fragrances. The compound is mainly made synthetically and is a precursor to other synthetic compounds. It is an ether.

Sulfonic acid

A sulfonic acid (or sulphonic acid) refers to a member of the class of organosulfur compounds with the general formula R−S(=O)2−OH, where R is an organic alkyl or aryl group and the S(=O)2(OH) group a sulfonyl hydroxide. As a substituent, it is known as a sulfo group. A sulfonic acid can be thought of as sulfuric acid with one hydroxyl group replaced by an organic substituent. The parent compound (with the organic substituent replaced by hydrogen) is the parent sulfonic acid, HS(=O)2(OH), a tautomer of sulfurous acid, S(=O)(OH)2. Salts or esters of sulfonic acids are called sulfonates.

Catechol Chemical compound

Catechol ( or ), also known as pyrocatechol or 1,2-dihydroxybenzene, is a toxic organic compound with the molecular formula C6H4(OH)2. It is the ortho isomer of the three isomeric benzenediols. This colorless compound occurs naturally in trace amounts. It was first discovered by destructive distillation of the plant extract catechin. About 20,000 tonnes of catechol is now synthetically produced annually as a commodity organic chemical, mainly as a precursor to pesticides, flavors, and fragrances.

Cyclohexanone Chemical compound

Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oil has an odor reminiscent of that of acetone. Over time, samples of cyclohexanone assume a yellow color. Cyclohexanone is slightly soluble in water and miscible with common organic solvents. Billions of kilograms are produced annually, mainly as a precursor to nylon.

Diazonium compound Diazonium salts of formula R-N≡N+

Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group R−N+
2
X
where R can be any organic group, such as an alkyl or an aryl, and X is an inorganic or organic anion, such as a halogen.

Thiophenol Chemical compound

Thiophenol is an organosulfur compound with the formula C6H5SH, sometimes abbreviated as PhSH. This foul-smelling colorless liquid is the simplest aromatic thiol. The chemical structures of thiophenol and its derivatives are analogous to phenols except the oxygen atom in the hydroxyl group (-OH) bonded to the aromatic ring is replaced by a sulfur atom. The prefix thio- implies a sulfur-containing compound and when used before a root word name for a compound which would normally contain an oxygen atom, in the case of 'thiol' that the alcohol oxygen atom is replaced by a sulfur atom.

Xylenols are organic compounds with the formula (CH3)2C6H3OH. They are volatile colorless solids or oily liquids. They are derivatives of phenol with two methyl groups at various positions relative to the hydroxyl group. Six isomers exist, of which 2,6-xylenol with both methyl groups in an ortho position with respect to the hydroxyl group is the most important. The name xylenol is a portmanteau of the words xylene and phenol.

4-Hydroxybenzoic acid, also known as p-hydroxybenzoic acid (PHBA), is a monohydroxybenzoic acid, a phenolic derivative of benzoic acid. It is a white crystalline solid that is slightly soluble in water and chloroform but more soluble in polar organic solvents such as alcohols and acetone. 4-Hydroxybenzoic acid is primarily known as the basis for the preparation of its esters, known as parabens, which are used as preservatives in cosmetics and some ophthalmic solutions. It is isomeric with 2-hydroxybenzoic acid, known as salicylic acid, a precursor to aspirin, and with 3-hydroxybenzoic acid.

Phloretic acid Chemical compound

Phloretic acid is an organic compound with the formula HOC6H4(CH2)2CO2H. It is a white solid. The compound contains both phenol and carboxylic acid functional groups. It is sometimes called Desaminotyrosine (DAT) because it is identical to the common alpha amino acid tyrosine except for the absence of the amino functional group on the alpha carbon.

4-Methylsalicylic acid is an organic compound with the formula CH3C6H3(CO2H)(OH). It is a white solid that is soluble in basic water and in polar organic solvents. Its functional groups include a carboxylic acid and a phenol group. It is one of four isomers of methylsalicylic acid, including the naturally occurring 6-methylsalicylic acid. The compound has few applications. It can be prepared by hydroxylation of 4-methylbenzoic acid.

6-Methylsalicylic acid Chemical compound

6-Methylsalicylic acid is an organic compound with the formula CH3C6H3(CO2H)(OH). It is a white solid that is soluble in basic water and in polar organic solvents. At neutral pH, the acid exists as 6-methylsalicylate Its functional groups include a carboxylic acid and a phenol group. It is one of four isomers of methylsalicylic acid.

5-Methylsalicylic acid Chemical compound

5-Methylsalicylic acid is an organic compound with the formula CH3C6H3(CO2H)(OH). It is a white solid that is soluble in basic water and in polar organic solvents. At neutral pH, the acid exists as 5-methylsalicylate Its functional groups include a carboxylic acid and a phenol group. It is one of four isomers of methylsalicylic acid.

References

  1. Takayuki Iijima; Tatsuaki Yamaguchi (2001). "K2CO3-Catalyzed Direct Synthesis of Salicylic Acid from Phenol and Supercritical CO2". Applied Catalysis A. 345: 12–17. doi:10.1016/j.apcata.2008.03.037.