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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/11/12 02:24:22」(JST)
[Wiki ja表示]
2,4-ジニトロクロロベンゼン
2,4-Dinitrochlorobenzene |
|
IUPAC名
1-Chloro-2,4-dinitrobenzene
|
別称
1-クロロ-2,4-ジニトロベンゼン
DNCB
|
識別情報 |
略称 |
CDNB; DNCB |
CAS登録番号 |
97-00-7 |
PubChem |
6 |
ChemSpider |
5 |
日化辞番号 |
J3.974H |
- c1cc(c(cc1[N+](=O)[O-])[N+](=O)[O-])Cl
|
特性 |
化学式 |
C6H3ClN2O4 |
モル質量 |
202.55 g mol−1 |
外観 |
淡黄色の結晶状粉末 |
融点 |
52-54 ℃
|
沸点 |
315 ℃
|
水への溶解度 |
0.0092 g/L(25 ℃) |
危険性 |
引火点 |
194 ℃ |
発火点 |
432 ℃ |
半数致死量 LD50 |
640 mg/kg(ラット経口)
130 mg/kg(ウサギ経皮) |
特記なき場合、データは常温 (25 °C)・常圧 (100 kPa) におけるものである。 |
2,4-ジニトロクロロベンゼン(英: 2,4-Dinitrochlorobenzene)はベンゼンの誘導体の一種。DNCBとも表記される。
用途
DNCBはほとんどの人のIV型アレルギーを誘発することから、免疫不全症患者のT細胞の活性の診断に使用される。イボの治療に使用されることもある[1][2]。 DNCBは、グルタチオン-S-トランスフェラーゼ (GST) の酵素活性試験の基質として使用されている[3]。DNCBが還元型グルタチオン1分子に抱合されると、340 nmのUV吸収が増大する。
安全性
日本の消防法では、ニトロ化合物として第5類危険物に分類される。皮膚・目に対する刺激性があり、特に皮膚に対してはアレルギー性反応を生じることがある[4]。
脚注
- ^ “Treating warts”. Harvard Medical School. 2010年4月2日閲覧。
- ^ Gibbs S, Harvey I, Sterling J, Stark R (2002). "Local treatments for cutaneous warts: systematic review". BMJ 325 (7362): 461. doi:10.1136/bmj.325.7362.461. PMC 119440. PMID 12202325.
- ^ Habig WH, Pabst MJ, Jakoby WB (1974). "Glutathione S-transferases. The first enzymatic step in mercapturic acid formation". J. Biol. Chem. 249 (22): 7130–7139. PMID 4436300.
- ^ “化学物質等安全データシート: 2,4-ジニトロクロロベンゼン (PDF)”. 昭和化学 (2011年5月17日). 2011年10月25日閲覧。
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この項目は、化学に関連した書きかけの項目です。この項目を加筆・訂正などしてくださる協力者を求めています(プロジェクト:化学/Portal:化学)。 |
[Wiki en表示]
2,4-Dinitrochlorobenzene
|
Names |
IUPAC name
1-Chloro-2,4-dinitrobenzene
|
Other names
Dinitrochlorobenzene; Chlorodinitrobenzene; 2,4-Dinitrochlorobenzene; 2,4-Dinitrophenyl chloride; 4-Chloro-1,3-dinitrobenzene
|
Identifiers |
CAS Registry Number
|
97-00-7 Y |
Abbreviations |
CDNB; DNCB |
ChEBI |
CHEBI:34718 N |
ChemSpider |
5 Y |
EC number |
202-551-4 |
InChI
-
InChI=1S/C6H3ClN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H
Key: VYZAHLCBVHPDDF-UHFFFAOYSA-N
|
Jmol-3D images |
Image |
PubChem |
6 |
SMILES
-
c1cc(c(cc1[N+](=O)[O-])[N+](=O)[O-])Cl
|
Properties |
Chemical formula
|
C6H3ClN2O4 |
Molar mass |
202.55 g·mol−1 |
Appearance |
yellow crystals |
Odor |
almond-like |
Density |
1.6867 g/cm3 |
Melting point |
54 °C (129 °F; 327 K) |
Boiling point |
315 °C (599 °F; 588 K) |
Solubility in water
|
Insoluble[1] |
Solubility |
soluble in ether, benzene, CS2 |
Refractive index (nD)
|
1.5857 (60 °C) |
Hazards |
NFPA 704 |
|
Explosive limits |
2-22% |
Lethal dose or concentration (LD, LC): |
LD50 (Median dose)
|
1.07 g/kg (rat, oral) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
N verify (what is: Y/N?) |
Infobox references |
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2,4-Dinitrochlorobenzene (DNCB) is an organic compound with the formula (O2N)2C6H3Cl. It is a yellow solid that is soluble in organic solvents. It is an important intermediate for the industrial production of other compounds.[2]
DNCB is produced commercially by the nitration of p-nitrochlorobenzene with a mixture of nitric and sulfuric acids. Other methods afford the compound less efficiently include the chlorination of dinitrobenzene, nitration of o-nitrochlorobenzene and the dinitration of chlorobenzene.
Contents
- 1 Uses
- 2 Safety
- 3 References
Uses
By virtue of the two nitro groups, the chloride is susceptible to nucleophilic substitution. In this way, the compound is a precursor to many other compounds. Base gives the dinitrophenol, ammonia the dinitroaniline, methoxide the dinitroanisole, and amines the secondary amines.
Laboratory use
DNCB is used as a substrate in GST enzyme activity assays.[3] The molecule is conjugated to a single molecule of reduced glutathione which then absorbs at 340 nm. Affinity of CDNB for each class of GST varies and so it is not a good measure of activity for some forms (e.g. GSTT and GSTZ).[citation needed]
Safety
DNCB induces a type IV hypersensitivity reaction in almost all people exposed to it, so it is used medically to assess the T cell activity in patients. This is a useful diagnostic test for immunocompromised patients. It can also be used to treat warts.[4]
DNCB can cause contact dermatitis.[5]
References
- ^ "1-Chloro-2,4-dinitrobenzene". Sigma-Aldrich. Retrieved 8 September 2014.
- ^ Gerald Booth (2007). "Nitro Compounds, Aromatic". In: Ullmann's Encyclopedia of Industrial Chemistry. John Wiley & Sons: New York. doi:10.1002/14356007.a17_411
- ^ Habig WH, Pabst MJ, Jakoby WB (1974). "Glutathione S-transferases. The first enzymatic step in mercapturic acid formation". J Biol Chem 249 (22): 7130–7139. PMID 4436300.
- ^ "Treating warts". Harvard Medical School. Retrieved April 2, 2010.
- ^ White SI, Friedmann PS, Moss C, Simpson JM (1986). "The effect of altering area of application and dose per unit area on sensitization by DNCB". Br. J. Dermatol. 115 (6): 663–8. doi:10.1111/j.1365-2133.1986.tb06646.x. PMID 3801307.
UpToDate Contents
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English Journal
- Performance of the N/TERT epidermal model for skin sensitizer identification via Nrf2-Keap1-ARE pathway activation.
- Alloul-Ramdhani M1, Tensen CP1, El Ghalbzouri A2.
- Toxicology in vitro : an international journal published in association with BIBRA.Toxicol In Vitro.2014 Apr 30. pii: S0887-2333(14)00070-8. doi: 10.1016/j.tiv.2014.04.007. [Epub ahead of print]
- Animal testing of chemical ingredients for cosmetic purposes is prohibited. Therefore there is an urgent need for in vitro models to identify chemical allergens. In human skin, keratinocytes (KCs) are abundantly present and are key players in initiation of allergic contact dermatitis. One of the pat
- PMID 24794257
- Role of Ros and HMGB1 In Contact Allergen-Induced IL-18 Production in Human Keratinocytes.
- Galbiati V, Papale A, Galli CL, Marinovich M, Corsini E.
- The Journal of investigative dermatology.J Invest Dermatol.2014 Apr 29. doi: 10.1038/jid.2014.203. [Epub ahead of print]
- Keratinocytes play a key role in all phases of allergic contact dermatitis. We have recently identified the possibility to use IL-18 production for the in vitro identification of contact allergens. The purpose of this study was to characterize the molecular mechanisms underlying allergen-induced IL-
- PMID 24780928
- Topical application of Kochia scoparia inhibits the development of contact dermatitis in mice.
- Choi YY1, Kim MH1, Lee JY2, Hong J2, Kim SH3, Yang WM4.
- Journal of ethnopharmacology.J Ethnopharmacol.2014 Apr 19. pii: S0378-8741(14)00284-0. doi: 10.1016/j.jep.2014.04.009. [Epub ahead of print]
- ETHNOPHARMACOLOGICAL RELEVANCE: Kochia scoparia (Chenopodiaceae) has been reported to have anti-nociceptive, anti-inflammatory, anti-allergic, and anti-pruritic actions. This study investigated the anti-inflammatory effects of externally applied Kochia scoparia water extract (KSW) in 2,4-dinitrochlo
- PMID 24751363
Japanese Journal
- The relationship between CD86 and CD54 protein expression and cytotoxicity following stimulation with contact allergen in THP-1 cells
- Nukada Yuko,Ito Yuichi,Miyazawa Masaaki,Sakaguchi Hitoshi,Nishiyama Naohiro
- The Journal of Toxicological Sciences 36(3), 313-324, 2011
- … Finally, the humoral factors from dead cells induced by dinitrochlorobenzene (DNCB) were exposed to fresh THP-1 cells to confirm whether protein expression depended on cytotoxicity. …
- NAID 130000868807
- Modification of cell-surface thiols elicits activation of human monocytic cell line THP-1 : Possible involvement in effect of haptens 2,4-dinitrochlorobenzene and nickel sulfate
- Hirota Morihiko,Suzuki Mie,Hagino Shigenobu,Kagatani Saori,Sasaki Yoshinori,Aiba Setsuya,Itagaki Hiroshi
- Journal of toxicological sciences 34(2), 139-150, 2009-04-01
- … 2,4-Dinitrochlorobenzene (DNCB), but not dinitrophenol (DNP)-conjugated bovine serum albumin or DNP-conjugated fetal bovine serum, induced CD86 expression. … DNCB and nickel sulfate (NiSO_4) also induced related changes of cell-surface thiols and phosphorylation of p38 MAPK. … However, DNCB is membrane-permeable, and so its direct effect may not be confined to cell membrane proteins. …
- NAID 110007160550
Related Links
- 2,4-Dinitrochlorobenzene. IUPAC名. 1-Chloro-2,4-dinitrobenzene. 別称. 1-クロロ- 2,4-ジニトロベンゼン. DNCB. 識別情報. 略称, CDNB ... DNCBはほとんどの人のIV型 アレルギーを誘発することから、免疫不全症患者のT細胞の活性の診断に使用される。
Related Pictures
★リンクテーブル★
[★]
- 英
- 1-chloro-2,4-dinitrobenzene DNCB