| 词条 | N-Acetylanthranilic acid |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 456483862 | Name = N-Acetylanthranilic acid | ImageFile = N-acetylanthranilic_acid.svg | ImageSize = 120px | ImageName = N-acetylanthranilic Acid | IUPACName = 2-Acetamidobenzoic acid | OtherNames = 2-Acetamidobenzoic acid; 2-Carboxyacetanilide; o-Acetoaminobenozic acid; Acetylanthranilic acid; 2-(Acetylamino)benzoic acid |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|changed|??}} | CASNo = 89-52-1 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 36555 | PubChem = 6971 | SMILES = CC(=O)NC1=CC=CC=C1C(=O)O | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 6705 | InChI = 1/C9H9NO3/c1-6(11)10-8-5-3-2-4-7(8)9(12)13/h2-5H,1H3,(H,10,11)(H,12,13) | InChIKey = QSACCXVHEVWNMX-UHFFFAOYAX | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C9H9NO3/c1-6(11)10-8-5-3-2-4-7(8)9(12)13/h2-5H,1H3,(H,10,11)(H,12,13) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = QSACCXVHEVWNMX-UHFFFAOYSA-N |Section2={{Chembox Properties | C=9 | H=9 | N=1 | O=3 | Appearance = | Density = 1.36 g/mL | MeltingPtC = 184 to 186 | MeltingPt_notes = | BoilingPtC = 399 | BoilingPt_notes = | Solubility = | pKa = | pKb = |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = |Section8={{Chembox Related | OtherCompounds = }}N-Acetylanthranilic acid is an organic compound with the molecular formula C9H9NO3. It is an intermediate product in catabolism of quinaldine in Arthrobacter sp., and is further metabolized to anthranilic acid.[1][2] N-Acetylanthranilic acid can be synthesized from 2-bromoacetanilide via palladium-catalyzed carbonylation in tri-n-butylamine-water at 110-130 °C, under 3 atm of carbon monoxide.[3] In the laboratory, it can be easily synthesized from anthranilic acid and acetic anhydride. N-Acetylanthranilic acid exhibits triboluminescence when crushed.[4] The fractured crystals have large electrical potentials between areas of high and low charge. When the electrons suddenly migrate to neutralize these potentials, flashes of deep blue light are created. In the United States, it is a Drug Enforcement Administration-controlled Table I illicit drug precursor,[5] because it has been used in the synthesis of methaqualone. See also
References1. ^{{cite journal | vauthors = Hund HK, de Beyer A, Lingens F | date = 1990 | title = Microbial metabolism of quinoline and related compounds. VI. Degradation of quinaldine by Arthrobacter sp | journal = Biol Chem Hoppe-Seyler | volume= 371 |issue =10 |pages = 1005–1008 | doi = 10.1515/bchm3.1990.371.2.1005 | pmid = 2076195}} {{DEFAULTSORT:Acetylanthranilic acid, N-}}2. ^{{cite journal |vauthors=Overhage J, etal | date = 2005 | title = Identification of large linear plasmids in Arthrobacter spp. encoding the degradation of quinaldine to anthranilate | journal = Microbiology | volume = 151 |issue=2 |pages=491–500 | doi = 10.1099/mic.0.27521-0 | pmid = 15699198}} 3. ^{{cite journal | author = Donald Valentine | author2 = Jefferson W. Tilley | author3 = Ronald A. LeMahieu | date = 1981 | title = Practical, catalytic synthesis of anthranilic acids | journal = Journal of Organic Chemistry | volume=46 |issue = 22 |pages = 4614–4617 | doi = 10.1021/jo00335a075 | pmid = }} 4. ^{{cite journal | vauthors = Erikson J | title = N-acetylanthranilic acid. A highly triboluminescent material | journal = J Chem Educ | date = Oct 1972 | volume = 49 | issue = 10 | pages = 688 | doi = 10.1021/ed049p688 }} 5. ^{{cite web|url=http://www.deadiversion.usdoj.gov/21cfr/cfr/1310/1310_02.htm |title=PART 1310 - Section 1310.02 Substances covered |website=www.deadiversion.usdoj.gov}} 2 : Anthranilic acids|Acetanilides |
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