| Identification | More | [Name]
2,3-Dichlorobenzoic acid | [CAS]
50-45-3 | [Synonyms]
2,3-DICHLOROBENZOIC ACID
RARECHEM AL BO 0323
TIMTEC-BB SBB003641
2,3-dichloro-benzoicaci
2,3-DICHLOROBENZOIC ACID PESTANAL, 250 M
2,3-Dichlorobenzoicacid,98%
2,3-Dichlorobenzoic
2,3-Dichlorbenzoesure
2,3-DICHLOROBENZOIC ACID pure | [EINECS(EC#)]
200-039-5 | [Molecular Formula]
C7H4Cl2O2 | [MDL Number]
MFCD00002413 | [Molecular Weight]
191.01 | [MOL File]
50-45-3.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powder | [Melting point ]
168-170 °C (lit.) | [Boiling point ]
273.68°C (rough estimate) | [density ]
1.4410 (rough estimate) | [refractive index ]
1.4590 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | [form ]
neat | [pka]
2.53±0.25(Predicted) | [color ]
White to Off-White | [Water Solubility ]
slightly soluble | [BRN ]
1946217 | [InChI]
InChI=1S/C7H4Cl2O2/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3H,(H,10,11) | [InChIKey]
QAOJBHRZQQDFHA-UHFFFAOYSA-N | [SMILES]
C(O)(=O)C1=CC=CC(Cl)=C1Cl | [CAS DataBase Reference]
50-45-3(CAS DataBase Reference) | [EPA Substance Registry System]
50-45-3(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P305+P351+P338 | [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 .
S37/39:Wear suitable gloves and eye/face protection .
S36:Wear suitable protective clothing .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
2
| [RTECS ]
DG6475000
| [TSCA ]
TSCA listed | [REACH Registrations]
Active | [HazardClass ]
IRRITANT | [HS Code ]
29163900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
2,3-Dichlorobenzoic acid sodium salt-->2,3-Dichlorobenzonitrile-->2,3-Dichlorobenzamide-->2,3-Dichloroaniline-->2,6-Dichlorobenzoic acid-->Carbon dioxide-->2-Chlorobenzoic acid | [Preparation Products]
Lamotrigine-->2,3,4-Trichlorobenzoic acid-->2,3-Dichlorobenzyl alcohol-->2,3-Dichlorobenzyl bromide-->2,3-Dichlorophenylacetonitrile-->2,3-Dichlorobenzoyl cyanide |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powder | [Uses]
2,3-Dichlorobenzoic acid is the key intermediate for antiepileptic drug Lamotrigine (L173250) and other pharmaceuticals for the treatment of central nervous system (CNS) disorders and disease. | [Definition]
ChEBI: 2,3-dichlorobenzoic acid is a chlorobenzoic acid that is benzoic acid in which the ring hydrogens at positions 2 and 3 are substituted by chloro groups. It has a role as an impurity and a bacterial xenobiotic metabolite. It is a chlorobenzoic acid and a dichlorobenzene. It is functionally related to a benzoic acid. It is a conjugate acid of a 2,3-dichlorobenzoate. | [General Description]
2,3-Dichlorobenzoic acid is an intermediate metabolite of polychlorinated biphenyls (PCBs). | [Synthesis]
2,3-Dichlorobenzoic acid was prepared from 2,3-dichloroaniline by diazotization and Myerwine reaction to 2,3-dichlorobenzaldehyde, and then oxidized by potassium permanganate, with an overall yield of 45%.
Another synthesis of 2,3-dichlorobenzoic acid:
Step (a) A solution of 2,3-dichloroiodobenzene in sodium dried ether was added dropwise to magnesium turnings and a crystal of iodine with warming so as to form a Grignard reagent.
Step (b) The mixture of Step (a) was stirred and refluxed then cooled and transferred dropwise, under nitrogen, into a stirred mixture of sodium dried ether containing solid carbon dioxide.
Step (c) The mixture of Step (b) was stirred for 2 hours, left overnight to warm to room temperature, then treated with ice and aqueous hydrochloric acid, and the product extracted with ether. The combined ether extracts were washed with water then repeatedly extracted with an aqueous sodium hydroxide. These basic solutions were combined, stirred with activated charcoal for 10 minutes, filtered and the cooled filtrate was acidified with concentrated hydrochloric acid at lO.degree. C.
Step (d) The resultant solid was filtered off, washed with water (2.times.20 mis) and dried in vacuo. Yield 77.6%. | [Purification Methods]
Aromatic acid impurities (to <0.05%) can be removed via the (±)--methylbenzylamine salt as described for 2,4-dichlorobenzoic acid [Ley & Yates Organic Process Research & Development 12 120 2008.] Crystallise the acid from H2O, aqueous EtOH, or 30% aqueous AcOH and several times from *C6H6, then dry it in vacuo at 40o overnight. The methyl ester has m 35-39o . [Hope & Riley J Chem Soc 123 2478 1923, Lock Monatsh Chem 90 687 1959, Shorter & Mather J Chem Soc 4744 1961, Beilstein 9 II 228, 9 IV 998.] |
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