4-硝基甲苯

4-硝基甲苯
	IUPAC名; 1-Methyl-4-nitrobenzene
别名	p-nitrotoluene ; p-mononitrotoluene
识别
CAS号	99-99-0
PubChem	7473
ChemSpider	13863774
SMILES	O=[N+]([O-])c1ccc(C)cc1;
性质
化学式	C7H7NO2
摩尔质量	137.14 g·mol−1
外观	浅黄色晶体
氣味	芳香
密度	1.1038 g·cm−3 (75 °C)
熔点	51.63 °C（325 K）（）
沸点	238.3 °C（511 K）（）
溶解性（水）	0.04% (20°C)
蒸氣壓	0.1 mmHg (20°C)
磁化率	−72.06·10−6 cm3/mol
危险性
爆炸極限	1.6%–?
PEL	TWA 5 ppm (30 mg/m3) [skin]
	致死量或浓度：
LD50（中位剂量）	1231 mg/kg （小鼠口服）; 1960 mg/kg （大鼠口服）; 1750 mg/kg （兔子口服）
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

4-硝基甲苯，又称对硝基甲苯，是一种有机化合物，化学式 CH₃C₆H₄NO₂.。它是一种浅黄色固体，为硝基甲苯的一种异构体。

制备和反应

类似其它硝基甲苯的异构体，4-硝基甲苯可以由甲苯在室温下硝化而成。^[4] ^[5]它可被氢化成4-甲基苯胺。^[6]它在四氯化碳中可以被一氧化二氯氯化为4-硝基-α,α,α-三氯甲苯。^[7]

应用

4-硝基甲苯的主要应用包括磺化生成 4-硝基甲苯-2-磺酸（其中的-SO₃H 基团与甲基相邻）。该物种可以氧化偶联产生芪衍生物，^[8]可用作染料。^[9]

危险性

有证据表明，4-硝基甲苯对小鼠有毒性和致癌性。^[10]

参考资料

^ ^1.0 ^1.1 ^1.2 ^1.3 ^1.4 ^1.5 NIOSH Pocket Guide to Chemical Hazards. #0464. NIOSH.
^ ^2.0 ^2.1 ^2.2 Lide DR (编). CRC handbook of chemistry and physics: a ready-reference book of chemical and physical data 85. Boca Ratan Florida: CRC Press. 2004. ISBN 0-8493-0485-7.
^ Nitrotoluene. Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ Gerald Booth, Nitro Compounds,Aromatic, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a17_411
^ 潘亞芬、張永士. 基礎化學. : 頁193 [2022-03-19]. （原始内容存档于2022-03-19）.
^ Astha Shukla, Rajib K. Singha, Takehiko Sasaki, Vemulapalli V. D. N. Prasad, Rajaram Bal. Synthesis of Highly Active Pd Nanoparticles Supported Iron Oxide Catalyst for Selective Hydrogenation and Cross‐Coupling Reactions in Aqueous Medium. ChemistrySelect. 2019-05-08, 4 (17): 5019–5032 [2021-07-29]. ISSN 2365-6549. doi:10.1002/slct.201900358 （英语）.
^ F. D. Marsh, W. B. Farnham, D. J. Sam, B. E. Smart. Dichlorine monoxide: a powerful and selective chlorinating reagent. Journal of the American Chemical Society. 1982-08, 104 (17): 4680–4682 [2021-07-29]. ISSN 0002-7863. doi:10.1021/ja00381a032. （原始内容存档于2021-07-29）（英语）.
^ Cumming, William M.; Hopper, I. Vance; Wheeler, T. Sherlock. Preparation 294.—Dinitro-Stilbene-Disulphonic Acid (Na salt). Systematic Organic Chemistry: Modern Methods of Preparation and Estimation. New York: D. Van Nostrand Company. 1926: 314.
^ Hunger, Klaus; Mischke, Peter; Rieper, Wolfgang; Raue, Roderich; Kunde, Klaus; Engel, Aloys, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a03_245
^ National Toxicology, Program. Toxicology and carcinogenesis studies of p-nitrotoluene (CAS no. 99-99-0) in F344/N rats and B6C3F(1) mice (feed studies). National Toxicology Program Technical Report Series. 2002, (498): 1–277. PMID 12118261.

外部链接

CDC – NIOSH Pocket Guide to Chemical Hazards – p-Nitrotoluene （页面存档备份，存于互联网档案馆）

[PGCH-1] 1.0 ^1.1 ^1.2 ^1.3 ^1.4 ^1.5 NIOSH Pocket Guide to Chemical Hazards. #0464. NIOSH.

[CRC_85-2] 2.0 ^2.1 ^2.2 Lide DR (编). CRC handbook of chemistry and physics: a ready-reference book of chemical and physical data 85. Boca Ratan Florida: CRC Press. 2004. ISBN 0-8493-0485-7.

[3] Nitrotoluene. Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[Booth-4] Gerald Booth, Nitro Compounds,Aromatic, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a17_411

[5] 潘亞芬、張永士. 基礎化學. : 頁193 [2022-03-19]. （原始内容存档于2022-03-19）.

[6] Astha Shukla, Rajib K. Singha, Takehiko Sasaki, Vemulapalli V. D. N. Prasad, Rajaram Bal. Synthesis of Highly Active Pd Nanoparticles Supported Iron Oxide Catalyst for Selective Hydrogenation and Cross‐Coupling Reactions in Aqueous Medium. ChemistrySelect. 2019-05-08, 4 (17): 5019–5032 [2021-07-29]. ISSN 2365-6549. doi:10.1002/slct.201900358 （英语）.

[7] F. D. Marsh, W. B. Farnham, D. J. Sam, B. E. Smart. Dichlorine monoxide: a powerful and selective chlorinating reagent. Journal of the American Chemical Society. 1982-08, 104 (17): 4680–4682 [2021-07-29]. ISSN 0002-7863. doi:10.1021/ja00381a032. （原始内容存档于2021-07-29）（英语）.

[8] Cumming, William M.; Hopper, I. Vance; Wheeler, T. Sherlock. Preparation 294.—Dinitro-Stilbene-Disulphonic Acid (Na salt). Systematic Organic Chemistry: Modern Methods of Preparation and Estimation. New York: D. Van Nostrand Company. 1926: 314.

[9] Hunger, Klaus; Mischke, Peter; Rieper, Wolfgang; Raue, Roderich; Kunde, Klaus; Engel, Aloys, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a03_245

[10] National Toxicology, Program. Toxicology and carcinogenesis studies of p-nitrotoluene (CAS no. 99-99-0) in F344/N rats and B6C3F(1) mice (feed studies). National Toxicology Program Technical Report Series. 2002, (498): 1–277. PMID 12118261.

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