ジニトロベンゼン
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2018/04/28 20:53:07」(JST)
[Wiki en表示]
Dinitrobenzenes are chemical compounds composed of a benzene ring and two nitro group (-NO2) substituents. The three possible arrangements of the nitro groups afford three isomers, 1,2-dinitrobenzene, 1,3-dinitrobenzene, and 1,4-dinitrobenzene. Each isomer has the chemical formula C6H4N2O4 and a molar mass of about 168.11 g/mol. 1,3-Dinitrobenzene is the most common isomer and it is used in the manufacture of explosives.
Contents
- 1 Properties
- 2 Preparation
- 3 Reactions
- 4 References
Properties
The dinitrobenzenes are all crystalline solids. The boiling points of the three isomers are relatively close; however, the melting points significantly differ. 1,4-Dinitrobenzene, which has the highest symmetry, has the highest melting point.
| Dinitrobenzenes |
| IUPAC name |
1,2-Dinitrobenzene |
1,3-Dinitrobenzene |
1,4-Dinitrobenzene |
| Other names |
o-Dinitrobenzene |
m-Dinitrobenzene |
p-Dinitrobenzene |
| Chemical structure |
|
|
|
| CAS number |
528-29-0 |
99-65-0 |
100-25-4 |
| 25154-54-5 (Unspecified isomers)[1] |
| PubChem |
CID 10707 from PubChem |
CID 7452 from PubChem |
CID 7492 from PubChem |
| Chemical formula |
C6H4N2O4 |
| Molar mass |
168.11 g/mol |
| Magnetic Susceptibility |
-65.98·10−6 cm3/mol |
-70.53·10−6 cm3/mol |
-68.30·10−6 cm3/mol |
| Physical state |
solid |
| Appearance |
Colorless crystals |
Yellowish crystals |
Colorless crystals |
| Melting point |
118 °C[2] |
89.6 °C[3] |
174 °C[4] |
| Boiling point |
318 °C[2] |
297 °C[3] |
299 °C[5] |
| Density |
1.565 g/cm3 (17 °C)[5] |
1.575 g/cm3 (18 °C)[5] |
1.625 g/cm3 (18 °C)[5] |
| Vapor pressure |
0.08 Pa (30 °C)[6] |
|
0.07 Pa (30 °C)[6] |
| 0.34 Pa (50 °C)[6] |
|
0.23 Pa (50 °C)[6] |
| Solubility |
Insoluble in water |
| GHS hazards[7] |
|
| R phrases |
R26/27/28-R33-R50/53 |
| S phrases |
(S1/2)-S28-S36/37-S45-S60-S61 |
Preparation
1,3-Dinitrobenzene is accessible by nitration of nitrobenzene. The reaction proceeds under acid catalysis using sulfuric acid. The directing effect of the nitro group of nitrobenzene leads to 93% of the product resulting from nitration at the meta-position. The ortho- and para-products occur in only 6% and 1%, respectively.[8]
Reactions
Reduction of 1,3-dinitrobenzene with sodium sulfide in aqueous solution leads to 3-nitroaniline. Further reduction with iron and hydrochloric acid (HCl) gives m-phenylenediamine.[9]
References
- ^ Record of CAS RN 25154-54-5 in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ^ a b Record of CAS RN 528-29-0 in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 11 March 2008.
- ^ a b Record of CAS RN 99-65-0 in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 11 March 2008.
- ^ Record of CAS RN 100-25-4 in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 11 March 2008.
- ^ a b c d Brockhaus ABC Chemie, VEB F.A. Brockhaus Verlag, Leipzig 1971.
- ^ a b c d Félix-Rivera, Hilsamar (2011). "Triacetone triperoxide thermogravimetric study of vapor pressure and enthalpy of sublimation in 303–338K temperature range". Thermochimica Acta. 514 (1-2): 37–43. doi:10.1016/j.tca.2010.11.034. )
- ^ Globally Harmonized System of Classification and Labelling of Chemicals (Second revised ed.), New York and Geneva: United Nations, 2007, ISBN 978-92-1-116957-7, ST/SG/AC.10/30/Rev.2
- ^ Joachim Buddrus (2003). Grundlagen der organischen Chemie (3 ed.). Berlin: de Gruyter. p. 360. ISBN 3-11-014683-5.
- ^ Hans Beyer and Wolfgang Walter (1981). Lehrbuch der Organischen Chemie (19 ed.). Stuttgart: S. Hirzel Verlag. pp. 536, 542. ISBN 3-7776-0356-2.
UpToDate Contents
全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.
- 1. 薬物過敏症：分類および臨床的特徴drug hypersensitivity classification and clinical features [show details]
…the many different clinical pictures of drug allergy (eg, contact dermatitis to 1-chloro-2,4-dinitrobenzene (DNCB), IgE-mediated anaphylaxis to penicillin). The different types of immunologic drug reactions…
English Journal
- Supersensitive and selective detection of picric acid explosive by fluorescent Ag nanoclusters.
- Zhang JR1, Yue YY, Luo HQ, Li NB.
- The Analyst.Analyst.2016 Feb 7;141(3):1091-7. doi: 10.1039/c5an02251g. Epub 2015 Dec 14.
- Picric acid (PA) explosive is a hazard to public safety and health, so the sensitive and selective detection of PA is very important. In the present work, polyethyleneimine stabilized Ag nanoclusters were successfully used for the sensitive and selective quantification of PA on the basis of fluoresc
- PMID 26661456
- The protective effect of lycopene on hypoxia/reoxygenation-induced endoplasmic reticulum stress in H9C2 cardiomyocytes.
- Gao Y1, Jia P2, Shu W3, Jia D4.
- European journal of pharmacology.Eur J Pharmacol.2016 Feb 1. pii: S0014-2999(16)30020-6. doi: 10.1016/j.ejphar.2016.02.005. [Epub ahead of print]
- Nowadays, drugs protecting ischemia/reperfusion (I/R) myocardium become more suitable for clinic. It has been confirmed lycopene has various protections, but lacking the observation of its effect on endoplasmic reticulum stress (ERS)-mediated apoptosis caused by hypoxia/reoxygenation (H/R). This stu
- PMID 26845695
- Development of highly sensitive and selective antibodies for the detection of the explosive pentaerythritol tetranitrate (PETN) by bioisosteric replacement.
- Hesse A1, Biyikal M2, Rurack K2, Weller MG1.
- Journal of molecular recognition : JMR.J Mol Recognit.2016 Feb;29(2):88-94. doi: 10.1002/jmr.2511. Epub 2015 Oct 14.
- An improved antibody against the explosive pentaerythritol tetranitrate (PETN) was developed. The immunogen was designed by the concept of bioisosteric replacement, which led to an excellent polyclonal antibody with extreme selectivity and immunoassays of very good sensitivity. Compounds such as nit
- PMID 26463875
Japanese Journal
- EGME及び1,3-DNB反復投与時のラット精巣における網羅的タンパク発現解析
- 土屋 卓磨,日堂 佑哉,高橋 則彦,阿部 香織
- 日本毒性学会学術年会 46.1(0), P-70, 2019
- … <p>【目的】代表的な精巣毒性物質であるEthylene glycol monomethyl ether（EGME）及び1,3-Dinitrobenzene（1,3-DNB）はそれぞれ精母細胞及びセルトリ細胞を主要な毒性標的細胞とし，反復投与時の精巣組織或いはホルモン等における経時的推移は異なる。 …
- NAID 130007677444
- コナガ（<i>Plutella xylostella</i>）由来の未分類グルタチオン転移酵素の機能解析
- 山本 幸治,広渡 愛子,塩月 孝博,山田 直隆
- 日本農薬学会誌（Ｊｏｕｒｎａｌ ｏｆ Ｐｅｓｔｉｃｉｄｅ Ｓｃｉｅｎｃｅ） 41(4), 145-151, 2016
- <p>コナガ（<i>Plutella xylostella</i>）由来の未分類グルタチオン転移酵素（GST）をコードするcDNAをRT-PCR法によりクローニングした．得られたクローンの全長を決定しアミノ酸配列を推定したところ，他生物由来のunclassified GSTと67%–73%の相同性を有していた．大腸菌を用いて組換えタンパク質を作製し，単一になるま …
- NAID 130005285072
- 接触性皮膚炎におけるプロスタグランジン最終合成酵素の役割
- 佐々木 由香,落合 翔,原 俊太郎
- 日本毒性学会学術年会 43.1(0), P-76, 2016
- … Balb/c系マウスの腹部に0.5％ 1-fluoro-2,4-dinitrobenzene (DNFB) を塗布して感作させたのち、5日後に0.3% DNFBを耳介に塗布し、接触性皮膚炎を惹起した。 …
- NAID 130005260880
Related Links
- Dinitrobenzene definition, any of three isomeric benzene derivatives having the formula C 6 H 4 NO 2 , made by nitration of benzene or nitrobenzene, the most important of which is the meta form: used chiefly in the manufacture of ...
- Structure, properties, spectra, suppliers and links for: m-dinitrobenzene, 99-65-0. ... 247.64 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column ...