| Identification | More | [Name]
2,3-Dimethylbenzoic acid | [CAS]
603-79-2 | [Synonyms]
2,3-DIMETHYLBENZOIC ACID
O-XYLENE-3-CARBOXYLIC ACID
RARECHEM AL BO 0357
2,3-dimethyl-benzoicaci
Hemellitic acid
hemelliticacid
Benzoic acid, 2,3-dimethyl-(7CI,8CI,9CI)
vic.-o-xylylic acid | [EINECS(EC#)]
210-058-0 | [Molecular Formula]
C9H10O2 | [MDL Number]
MFCD00002479 | [Molecular Weight]
150.17 | [MOL File]
603-79-2.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powder | [Melting point ]
144-146 °C (lit.) | [Boiling point ]
271.51°C (estimate) | [density ]
1.0937 (estimate) | [refractive index ]
1.5188 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
powder to crystal | [pka]
pKa: 3.771(25°C) | [color ]
White to Almost white | [BRN ]
971590 | [InChI]
InChI=1S/C9H10O2/c1-6-4-3-5-8(7(6)2)9(10)11/h3-5H,1-2H3,(H,10,11) | [InChIKey]
RIZUCYSQUWMQLX-UHFFFAOYSA-N | [SMILES]
C(O)(=O)C1=CC=CC(C)=C1C | [CAS DataBase Reference]
603-79-2(CAS DataBase Reference) | [NIST Chemistry Reference]
Benzoic acid, 2,3-dimethyl-(603-79-2) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S22:Do not breathe dust . | [WGK Germany ]
3
| [RTECS ]
DG8734000
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29163990 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powder | [Uses]
2,3-Dimethylbenzoic Acid is used as a reagent in the synthesis of pyridyl benzamides as inhibitors for the kinetoplastid Trypanosoma brucei. 2,3-Dimethylbenzoic Acid is also used as a reagent in the synthesis of 2,3-Dihydro-1H-isoindole-4-carboxylic Acid (D450070) which is a reagent used in the synthesis of aminoalkylbenzoic acid derivatives for the treatment of faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, neuropathic pain, neuropathological disorders and sleep disorders. | [Definition]
ChEBI: A dimethylbenzoic acid in which the two methyl groups are located at positions 2 and 3. | [General Description]
2,3-Dimethylbenzoic acid shows high binding affinity with antenna-specific odorant-binding protein of the alfalfa plant bug, Adelphocoris lineolatus. | [Synthesis]
1. 40 mL of dry o-xylene was rapidly added to a 250 mL PTFE-lined autoclave under argon protection. 2. 2.5 g of anhydrous aluminum trichloride (AlCl3) and 1.16 g of dry N-butylimidazole were added sequentially. Add 2.5 g of anhydrous aluminum trichloride (AlCl3) and 1.16 g of dry N-butylimidazole sequentially, and seal the reaction vessel after addition. 2. Connect a carbon dioxide cylinder to the autoclave through a pipeline, adjust the valve so that the CO2 pressure is maintained at 6 MPa, start the stirrer, and set the rotation speed at 1,000 rpm, and then begin to heat the system to 40°C, and the reaction lasts for 48 hours. 3. At the end of the reaction, 150 mL of water was added to the system and stirred for 30 min. 4. The reaction mixture was extracted three times with 50 mL of ether, and the organic phases were combined, concentrated and dried to give 2.76 g of an off-white solid, i.e., crude 2,3-dimethylbenzoic acid. 5. The above crude product was dissolved in 20 mL of a 10% (w/w) sodium hydroxide solution, and filtered to remove insoluble matter, to give a filtrate. 6. The filtrate was extracted with 1 mol/L hydrochloric acid to adjust the pH of the filtrate to 1 and let it stand at room temperature for 60 min. 7. The mixture was transferred to -10°C for further crystallization and filtered to obtain crystals. 8. The crystals were dried to obtain 2.29 g of white solid 2,3-dimethylbenzoic acid in 81.3% yield. | [Purification Methods]
Crystallise the acid from EtOH. It is volatile in steam. The amide has m 156o (from H2O). [Beilstein 9 H 531, 9 III 2434, 9 IV 1797.] | [References]
[1] Patent: CN107827742, 2018, A. Location in patent: Paragraph 0059; 0060 |
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