2,5-二硝基甲苯 | 619-15-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,5-二硝基甲苯
• 英文名称: 2,5-dinitrotoluene
• 英文别名: 2,5-Dinitrotoluol；2-methyl-1,4-dinitrobenzene；2,5-DNT
• CAS: 619-15-8
• 化学式: C₇H₆N₂O₄
• mdl: MFCD00047688
• 分子量: 182.136
• InChiKey: KZBOXYKTSUUBTO-UHFFFAOYSA-N

物化性质

• 熔点：
  52.5 °C
• 沸点：
  284 °C
• 密度：
  1.282 g/cm3(Temp: 111 °C)
• 物理描述：
  YELLOW-TO-ORANGE-YELLOW CRYSTALS WITH CHARACTERISTIC ODOUR.
• 颜色/状态：
  Needles from alcohol
• 闪点：
  404 °F (207 °C) (closed cup) /Dinitrotoluenes/
• 溶解度：
  In water, 219 mg/L at 25 °C
• 蒸汽密度：
  Relative vapor density (air = 1): 6.3
• 蒸汽压力：
  0.0005 mm Hg at 25 °C /extrapolated/
• 分解：
  Spontaneously decomposes above 536 °F (280 °C) & will cause an explosion if confined. ... Air of oxygen is not required for decomposition or oxidation. ... Contamination of DNT with organic materials lowers decomposition temperature & increases risk of explosion. /Dinitrotoluenes/
• 粘度：
  0.0055393 Pa.s at 323.48 K (est)
• 燃烧热：
  -3.4460E+09 J/kmol /Standard Net Heat of Comb/
• 表面张力：
  0.052567 N/m at 323.48 K (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  4

ADMET

代谢

从人类肠道中分离的大肠杆菌W3110菌株产生的5种DNT同分异构体（2,3-、2,4-、2,5-、2,6-和3,4-DNT）的代谢物已被鉴定。从大肠杆菌产生的代谢物中获得的数据是2-硝基甲苯和羟基氨基硝基甲苯。这一发现表明，在Escherichia coli中，DNT通过羟基氨基硝基甲苯还原为氨基硝基甲苯。另外，DNT同分异构体的还原活性为2,3-DNT的3- > 2-，2,4-DNT的4- > 2-，2,5-DNT的5- > 2-，以及3,4-DNT的3- > 4-。

The metabolites produced from 5 DNT isomers (2,3-, 2,4-, 2,5-, 2,6- and 3,4-DNT) by Escherichia coli strain W3110, isolated from human intestine, were identified. Data obtained from metabolites produced by the Escherichia coli were 2 monoaminonitrotoluenes and hydroxylaminonitrotoluenes in all cases. This finding indicates that DNT is reduced via hydroxylaminonitrotoluenes to monoaminonitrotoluenes in Escherichia coli. In addn, the redn reactivities of DNT isomers were 3- > 2- for 2,3-DNT, 4- > 2- for 2,4-DNT, 5- > 2- for 2,5-DNT and 3- > 4- for 3,4-DNT.

来源:Hazardous Substances Data Bank (HSDB)

代谢

二硝基甲苯在大鼠体内的生物活化被认为通过以下过程发生：甲基团通过细胞色素p450依赖途径被氧化成醇；苯甲基醇与葡萄糖酸酸结合并随胆汁排出体外。肠道微生物菌群水解葡萄糖苷酸并还原一个硝基团，形成可以重新从肠道吸收的氨基硝基苄醇。氨基团通过肝脏酶氧化成羟胺并与硫酸盐结合。硫酸酯的分解产生高度亲电子的硝基碳正离子（或碳正离子），它可以与DNA和其他生物亲核物质反应。

Bioactivation of dinitrotoluene in the rat is thought to occur by the following processes: The methyl group is oxidized to an alcohol by a cytochrome p450 dependent pathway; the benzyl alcohol is conjugated with glucoronic acid and excreted in the bile. Intestinal microflora hydrolyze the glucuronide and reduce one nitro group, forming an aminonitrobenzyl alcohol which can be readsorbed from the intestine. The amino group oxidized to an hydroxylamine by hepatic enzymes and conjugated with sulfate. Decomposition of the sulfate ester yields a highly electrophilic nitrenium (or carbonium) ion which can react with DNA and other biological nucleophiles.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

A3; 对动物已确认的致癌物，对人类的相关性未知。/二硝基甲苯/

A3; Confirmed animal carcinogen with unknown relevance to humans. /Dinitrotoluene/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 暴露途径

这种物质可以通过吸入、皮肤接触和摄入被身体吸收。

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 吸入症状

咳嗽。喉咙痛。嘴唇、手指甲和皮肤发青。

Cough. Sore throat. Blue lips, fingernails and skin.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 皮肤症状

可能被吸收！发红。疼痛。

MAY BE ABSORBED! Redness. Pain.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 眼睛症状

红肿。疼痛。

Redness. Pain.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

安全信息

• 危险品标志：
  T,N
• 危险类别码：
  R45
• 储存条件：
  | 室温 |

SDS

Name:	2 5-Dinitrotoluene Material Safety Data Sheet
Synonym:	2,5-DNT; 2-Methyl-1,4-dinitrobenzene
CAS:	619-15-8

Section 1 - Chemical Product MSDS Name:2 5-Dinitrotoluene Material Safety Data Sheet
Synonym:2,5-DNT; 2-Methyl-1,4-dinitrobenzene

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
619-15-8	2,5-Dinitrotoluene	100	210-581-4

Hazard Symbols: T N
Risk Phrases: 23/24/25 45 48/22 62 51/53

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Toxic by inhalation, in contact with skin and if swallowed. May cause cancer. Harmful : danger of serious damage to health by prolonged exposure if swallowed. Possible risk of impaired fertility. Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. Absorption into the body may cause cyanosis (bluish discoloration of skin due to deficient oxygenation of the blood).
Ingestion:
May cause irritation of the digestive tract. Methemoglobinemia is characterized by dizziness, drowsiness, headache, shortness of breath, cyanosis (bluish discoloration of skin due to deficient oxygenation of the blood), rapid heart rate and chocolate-brown colored blood. May be harmful if swallowed. May form methemoglobin which in sufficient concentration causes cyanosis (bluish discoloration of skin due to deficient oxygenation of the blood).
Inhalation:
May cause respiratory tract irritation. May cause methemoglobinemia, cyanosis (bluish discoloration of skin due to deficient oxygenation of the blood), convulsions, tachycardia, dyspnea (labored breathing), and death. Methemoglobinemia is characterized by dizziness, drowsiness, headache, shortness of breath, cyanosis (bluish discoloration of skin due to deficient oxygenation of the blood), rapid heart rate and chocolate-brown blood.
Chronic:
May cause methemoglobinemia, which is characterized by chocolate-brown colored blood, headache, weakness, dizziness, breath shortness, cyanosis (bluish skin due to deficient oxygenation of blood), rapid heart rate, unconsciousness and possible death. May cause cancer according to animal studies.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. Do NOT use mouth-to-mouth resuscitation.
Notes to Physician:
For methemoglobinemia, administer oxygen alone or with Methylene Blue depending on the methemoglobin concentration in the blood.
Antidote: Methylene blue, alone or in combination with oxygen is indicated as a treatment in nitrite induced methemoglobinemia.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Use water with caution and in flooding amounts. Containers may explode when heated. Combustible material; may burn but does not ignite readily.
Extinguishing Media:
Do NOT get water inside containers. For small fires, use dry chemical, carbon dioxide, or water spray. For large fires, use water spray, fog or regular foam. Cool containers with flooding quantities of water until well after fire is out.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels below recommended exposure limits. Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower.
Exposure Limits CAS# 619-15-8: CAS# 25321-14-6: United States OSHA: 1.5 mg/m3 TWA Belgium - TWA: 0.15 mg/m3 VLE Malaysia: 0.2 mg/m3 TWA Spain: 0.15 mg/m3 VLA-ED Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: yellow
Odor: toluene-like odor
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 53 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.2800g/cm3
Molecular Formula: C7H6N2O4
Molecular Weight: 182.14

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Metals, strong oxidizing agents, caustics (e.g. ammonia, ammonium hydroxide, calcium hydroxide, potassium hydroxide, sodium hydroxide).
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 619-15-8: XT1750000 CAS# 25321-14-6: XT1300000 LD50/LC50:
CAS# 619-15-8: Draize test, rabbit, skin: 500 mg/24H Moderate; Oral, mouse: LD50 = 652 mg/kg; Oral, rat: LD50 = 517 mg/kg.
CAS# 25321-14-6: Oral, mouse: LD50 = 750 mg/kg.
Carcinogenicity:
2,5-Dinitrotoluene - Not listed by ACGIH, IARC, or NTP.
Dinitrotoluene (mixed isomers) - ACGIH: A3 - Confirmed animal carcinogen with unknown relevance to California: carcinogen, initial date 5/1/96 Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION
Other No information available.

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: DINITROTOLUENES
Hazard Class: 6.1
UN Number: 2038
Packing Group: II
IMO
Shipping Name: DINITROTOLUENES
Hazard Class: 6.1
UN Number: 2038
Packing Group: II
RID/ADR
Shipping Name: DINITROTOLUENES
Hazard Class: 6.1
UN Number: 2038
Packing group: II
USA RQ: CAS# 25321-14-6: 10 lb final RQ; 4.54 kg final RQ

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T N
Risk Phrases:
R 45 May cause cancer.
R 23/24/25 Toxic by inhalation, in contact with skin
and if swallowed.
R 48/22 Harmful : danger of serious damage to health
by prolonged exposure if swallowed.
R 51/53 Toxic to aquatic organisms, may cause
long-term adverse effects in the aquatic environment.
R 62 Possible risk of impaired fertility.
Safety Phrases:
S 53 Avoid exposure - obtain special instructions
before use.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
S 61 Avoid release to the environment. Refer to
special instructions/safety data sheets.
WGK (Water Danger/Protection)
CAS# 619-15-8: 3
CAS# 25321-14-6: No information available.
Canada
CAS# 619-15-8 is listed on Canada's NDSL List.
CAS# 25321-14-6 is listed on Canada's DSL List.
CAS# 619-15-8 is not listed on Canada's Ingredient Disclosure List.
CAS# 25321-14-6 is listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 619-15-8 is listed on the TSCA inventory.
CAS# 25321-14-6 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,5-二硝基甲苯 生成 2,3,6-三硝基甲苯
  参考文献：
  名称：

  De Beule, Bulletin des Societes Chimiques Belges, 1933, vol. 42, p. 27,63, 65, 79

  摘要：

  DOI：
• 作为产物：
  描述：

  3-硝基甲苯 生成 2,5-二硝基甲苯
  参考文献：
  名称：

  Brady, Journal of the Chemical Society, 1922, vol. 121, p. 330

  摘要：

  DOI：

文献信息

• Gold nanoparticles anchored onto the magnetic poly(ionic-liquid) polymer as robust and recoverable catalyst for reduction of Nitroarenes
  作者：Firouz Matloubi Moghaddam、Seyed Ebrahim Ayati、Hamid Reza Firouzi、Seyed Hassan Hosseini、Ali Pourjavadi

  DOI：10.1002/aoc.3825

  日期：2017.12

  Gold nanoparticles supported on poly ionic‐liquid magnetic nanoparticles (MNP@PIL@Au) were synthesized by reduction of HAuCl4 with sodium borohydride. The synthesized catalyst was characterized using by AAS, TEM, FT‐IR, EDS, TGA and XRD techniques. The performance of the synthesized catalyst was investigated in the reduction of nitroarenes with NaBH4. The reaction was carried out for various nitroarenes

  通过用硼氢化钠还原HAuCl4来合成负载在聚离子液体磁性纳米颗粒（MNP @ PIL @ Au）上的金纳米颗粒。使用AAS，TEM，FT-IR，EDS，TGA和XRD技术对合成的催化剂进行了表征。研究了合成催化剂在NaBH 4还原硝基芳烃方面的性能。该反应是在水中和温和条件下对各种硝基芳烃进行的，产率很高。在其他官能团（例如卤化物和炔烃）存在下，还原硝基的催化剂选择性相当好。催化剂的再循环进行了8次，而其催化活性没有任何明显的损失。
• [EN] DIHYDROBENZOFURAN DERIVATIVES AS INSECTICIDAL COMPOUNDS<br/>[FR] DÉRIVÉS DE DIHYDROBENZOFURANE UTILISABLES EN TANT QUE COMPOSÉS INSECTICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2014135095A1

  公开（公告）日：2014-09-12

  Provided are compounds of formula (I) and methods of controlling insects, acarines, nematodes or molluscs, which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I).

  提供的是公式(I)的化合物以及控制昆虫、蜱虫、线虫或软体动物的方法，该方法包括将公式(I)的化合物的杀虫剂、杀蜱剂、杀线虫剂或杀软体动物剂有效量的化合物应用于害虫、害虫的栖息地或易受害虫侵害的植物上。
• Regiospecificity in nucleophilic displacement of aromatic nitro-groups
  作者：Fabio Benedetti、Donald R. Marshall、Charles J. M. Stiriling

  DOI：10.1039/c39820000918

  日期：——

  Displacement of nitro-groups by thiolate ions from aromatic polynitro-compounds is highly selective for nitro-groups adjacent to alkyl groups except when the thiolate ion is bulky, the alkyl group is bulky, or both.

  硫醇盐离子从芳香族多硝基化合物置换硝基基团对于与烷基相邻的硝基基团具有高度选择性，除非硫醇盐离子笨重，烷基笨重或两者兼有。
• PROCESS FOR THE PREPARATION OF NITRATED AROMATICS AND MIXTURES THEREOF
  申请人：Mackenroth Wolfgang

  公开号：US20110306795A1

  公开（公告）日：2011-12-15

  A process for the preparation of mononitroaromatics and dinitroaromatics, in which a hydrate melt of at least one metal nitrate M(NO 3 ) 3 is used as a nitrating medium, it being possible for M to be the metals Fe, Cr, Y, La, Ce, Al, Bi and In, and the metal nitrate having a water content of from 4 to 9 mol of water per M(NO 3 ) 3 , leads to simplifications of the process and improved yields.

  一种用于制备单硝基芳香族化合物和二硝基芳香族化合物的方法，其中使用至少一种金属硝酸盐M(NO3)3的水合物熔融物作为硝化介质，M可以是Fe、Cr、Y、La、Ce、Al、Bi和In等金属，且金属硝酸盐的水含量为每M( )3含4至9摩尔水，这会导致工艺简化并提高收率。
• Competition between electron-donor and electron-acceptor substituents in nitrotoluene isomers: a photoelectron spectroscopy and ab initio investigation
  作者：Flaminia Rondino、Daniele Catone、Giuseppe Mattioli、Aldo Amore Bonapasta、Paola Bolognesi、Anna Rita Casavola、Marcello Coreno、Patrick O'Keeffe、Lorenzo Avaldi

  DOI：10.1039/c3ra45705b

  日期：——

  reactivity of the three nitrotoluene isomers: a joint experimental and theoretical study, based on X-ray photoelectron spectroscopy (XPS) measurements and ab initio calculations, addressing the complex interplay between the competing electron-donor and electron-acceptor effects of the nitro- and methyl-substituents on the chemical properties of the nitrotoluene isomers. As the main results of the investigation

  我们目前对三种硝基甲苯异构体的化学结构，物理性质和反应性之间的紧密关系进行研究：基于X射线光电子能谱（XPS）测量和从头算的联合实验和理论研究，解决了两者之间的复杂相互作用硝基和甲基取代基对硝基甲苯异构体化学性质的竞争性电子给体和电子受体效应。作为调查的主要结果，我们：（i）指出准确的从头算起在所有合格场所中，计算在光发射测量的完全分配以及质子亲和力估计中起着关键作用；（ii）基于芳香环不同取代基的感应和共振效应，以及甲基与π共轭体系的超共轭连接，更定量地回顾教科书模型；（iii）提供计算的质子亲和力和核心电离能之间的相关模式的准确分析，这是一个有力的工具，能够预测亲电芳族取代反应中多取代分子的位点特异性反应性。

表征谱图