4-硝基甲苯

4-硝基甲苯
	IUPAC名; 1-Methyl-4-nitrobenzene
別名	p-nitrotoluene ; p-mononitrotoluene
識別
CAS號	99-99-0
PubChem	7473
ChemSpider	13863774
SMILES	O=[N+]([O-])c1ccc(C)cc1;
性質
化學式	C7H7NO2
摩爾質量	137.14 g·mol−1
外觀	淺黃色晶體
氣味	芳香
密度	1.1038 g·cm−3 (75 °C)
熔點	51.63 °C（325 K）（）
沸點	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
危險性
爆炸極限	1.6%–?
PEL	TWA 5 ppm (30 mg/m3) [skin]
	致死量或濃度：
LD50（中位劑量）	1231 mg/kg （小鼠口服）; 1960 mg/kg （大鼠口服）; 1750 mg/kg （兔子口服）
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

4-硝基甲苯，又稱對硝基甲苯，是一種有機化合物，化學式 CH₃C₆H₄NO₂.。它是一種淺黃色固體，為硝基甲苯的一種異構體。

製備和反應

類似其它硝基甲苯的異構體，4-硝基甲苯可以由甲苯在室溫下硝化而成。^[4] ^[5]它可被氫化成4-甲基苯胺。^[6]它在四氯化碳中可以被一氧化二氯氯化為4-硝基-α,α,α-三氯甲苯。^[7]

應用

4-硝基甲苯的主要應用包括磺化生成 4-硝基甲苯-2-磺酸（其中的-SO₃H 基團與甲基相鄰）。該物種可以氧化偶聯產生芪衍生物，^[8]可用作染料。^[9]

危險性

有證據表明，4-硝基甲苯對小鼠有毒性和致癌性。^[10]

參考資料

^ ^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 (編). 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]. （原始內容存檔於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 （英語）.
^ 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. （原始內容存檔於2021-07-29）（英語）.
^ 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.

外部連結

CDC – NIOSH Pocket Guide to Chemical Hazards – p-Nitrotoluene （頁面存檔備份，存於網際網路檔案館）

[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 (編). 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]. （原始內容存檔於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 （英語）.

[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. （原始內容存檔於2021-07-29）（英語）.

[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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