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词条 2-Chlorobenzoic acid
释义

  1. Synthesis and reactions

  2. References

{{chembox
| verifiedrevid = 477197744
| ImageFile=2-Chlorobenzoic acid - Vect.svg
| ImageSize=120px
| IUPACName=2-chlorobenzoic acid
| OtherNames=o-Chlorobenzoic acid
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8071
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C02357
| InChI = 1/C7H5ClO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H,9,10)
| InChIKey = IKCLCGXPQILATA-UHFFFAOYAI
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 115243
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C7H5ClO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H,9,10)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = IKCLCGXPQILATA-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=118-91-2
| PubChem= 8374
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 30793
| SMILES = O=C(O)c1ccccc1Cl
}}
|Section2={{Chembox Properties
| C=7 | H=5 | Cl=1 | O=2
| Appearance=white solid
| Density=
| MeltingPtC=142
| BoilingPtC=285
| LogP = 2.039 [1]
| pKa = 2.89 [2] [3]
| Solubility=
| MagSus = -83.56·10−6 cm3/mol
|Section3={{Chembox Hazards
| ExternalSDS = Oxford MSDS {{dead link|date=February 2017}}
| FlashPt=
| AutoignitionPt =
}}2-Chlorobenzoic acid is an organic compound with the formula ClC6H4CO2H. It is one of three isomeric chlorobenzoic acids, the one that is the strongest acid. This white solid is used as a precursor to a variety of drugs, food additives, and dyes.[4]

Synthesis and reactions

It is prepared by the oxidation of 2-chlorotoluene. The laboratory scale reaction employs potassium permanganate.[5] Alternatively it arises by the hydrolysis of α,α,α-trichloro-2-toluene.

The chloride is readily replaced by ammonia to 2-aminobenzoic acid. At elevated temperature it decarboxylates.[4]

References

1. ^1.2-Chlorobenzoic acid; C7H5ClO2; ChemSpider. Chemspider.com (2015). at  
2. ^Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 1838
3. ^2.2-Chlorobenzoic acid; C7H5ClO2 - PubChem. Pubchem.ncbi.nlm.nih.gov at [https://pubchem.ncbi.nlm.nih.gov/compound/2-Chlorobenzoic_acid#section=Vapor-Pressure]
4. ^Takao Maki, Kazuo Takeda "Benzoic Acid and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a03_555}}.
5. ^{{OrgSynth | title = o-Chlorobenzoic acid | collvol = 2 | collvolpages = 135 | prep = cv2p0135 | author = H. T. Clarke and E. R. Taylor | year = 1943}}
{{DEFAULTSORT:Chlorobenzoic acid, 2-}}{{organohalide-stub}}

2 : Benzoic acids|Chloroarenes

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