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2-Chlorobenzoic acid

April 09, 2024

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]

2-Chlorobenzoic acid
Names
Preferred IUPAC name
2-Chlorobenzoic acid
Other names
o-Chlorobenzoic acid
Identifiers
  • 118-91-2 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:30793 Y
ChEMBL
  • ChEMBL115243 Y
ChemSpider
  • 8071 Y
ECHA InfoCard 100.003.897
KEGG
  • C02357 Y
  • 8374
UNII
  • 8P0867193V Y
  • DTXSID4024771
  • InChI=1S/C7H5ClO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H,9,10) Y
    Key: IKCLCGXPQILATA-UHFFFAOYSA-N Y
  • InChI=1/C7H5ClO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H,9,10)
    Key: IKCLCGXPQILATA-UHFFFAOYAI
  • O=C(O)c1ccccc1Cl
Properties
C7H5ClO2
Molar mass 156.57 g·mol−1
Appearance white solid
Melting point 142 °C (288 °F; 415 K)
Boiling point 285 °C (545 °F; 558 K)
log P 2.039 [1]
Acidity (pKa) 2.89 [2] [3]
-83.56·10−6 cm3/mol
Hazards
Safety data sheet (SDS)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)

Synthesis and reactions edit

See also: α,α,α-trichlorotoluene

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. Similarly, the chloride is displaced by diphenylphosphide, leading to 2-diphenylphosphinobenzoic acid.

At elevated temperature it decarboxylates.[4]

References edit

  1. ^ 1.2-Chlorobenzoic acid; C7H5ClO2; ChemSpider. Chemspider.com (2015). at [1]
  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 [2]
  4. ^ a b 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. ^ H. T. Clarke and E. R. Taylor (1943). "o-Chlorobenzoic acid". Organic Syntheses; Collected Volumes, vol. 2, p. 135.
 

This article about an organic halide is a stub. You can help Wikipedia by expanding it.

April 09, 2024
chlorobenzoic, acid, organic, compound, with, formula, clc6h4co2h, three, isomeric, chlorobenzoic, acids, that, strongest, acid, this, white, solid, used, precursor, variety, drugs, food, additives, dyes, namespreferred, iupac, name, other, names, chlorobenzoi. 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 2 Chlorobenzoic acid NamesPreferred IUPAC name 2 Chlorobenzoic acidOther names o Chlorobenzoic acidIdentifiersCAS Number 118 91 2 Y3D model JSmol Interactive imageChEBI CHEBI 30793 YChEMBL ChEMBL115243 YChemSpider 8071 YECHA InfoCard 100 003 897KEGG C02357 YPubChem CID 8374UNII 8P0867193V YCompTox Dashboard EPA DTXSID4024771InChI InChI 1S C7H5ClO2 c8 6 4 2 1 3 5 6 7 9 10 h1 4H H 9 10 YKey IKCLCGXPQILATA UHFFFAOYSA N YInChI 1 C7H5ClO2 c8 6 4 2 1 3 5 6 7 9 10 h1 4H H 9 10 Key IKCLCGXPQILATA UHFFFAOYAISMILES O C O c1ccccc1ClPropertiesChemical formula C 7H 5Cl O 2Molar mass 156 57 g mol 1Appearance white solidMelting point 142 C 288 F 415 K Boiling point 285 C 545 F 558 K log P 2 039 1 Acidity pKa 2 89 2 3 Magnetic susceptibility x 83 56 10 6 cm3 molHazardsSafety data sheet SDS Oxford MSDSExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox referencesSynthesis and reactions editSee also a a a trichlorotoluene It is prepared by the oxidation of 2 chlorotoluene The laboratory scale reaction employs potassium permanganate 5 Alternatively it arises by the hydrolysis of a a a trichloro 2 toluene The chloride is readily replaced by ammonia to 2 aminobenzoic acid Similarly the chloride is displaced by diphenylphosphide leading to 2 diphenylphosphinobenzoic acid At elevated temperature it decarboxylates 4 References edit 1 2 Chlorobenzoic acid C7H5ClO2 ChemSpider Chemspider com 2015 at 1 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 2 2 Chlorobenzoic acid C7H5ClO2 PubChem Pubchem ncbi nlm nih gov at 2 a b 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 H T Clarke and E R Taylor 1943 o Chlorobenzoic acid Organic Syntheses Collected Volumes vol 2 p 135 nbsp This article about an organic halide is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title 2 Chlorobenzoic acid amp oldid 1194222942, wikipedia, wiki, book, books, library,

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