2,4-二氯-5-氟-3-硝基苯甲酸 | 106809-14-7

• 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: 2,4-二氯-5-氟-3-硝基苯甲酸
• 中文别名: 2,4-二氯-3-硝基-5-氟苯甲酸；3-硝基-5-氟苯甲酸
• 英文名称: 2,4-dichloro-5-fluoro-3-nitro-benzoic acid
• 英文别名: 2, 4-dichloro-5-fluoro-3-nitrobenzoic acid；2,4-dichloro-3-nitro-5-fluorobenzoic acid；2,4-dichloro-5-fluoro-3-nitrobenzoic acid
• CAS: 106809-14-7
• 化学式: C₇H₂Cl₂FNO₄
• mdl: MFCD03427137
• 分子量: 254.002
• InChiKey: PCSAPCNEJUEIGU-UHFFFAOYSA-N

物化性质

• 熔点：
  193-197 °C (lit.)
• 沸点：
  390.4±42.0 °C(Predicted)
• 密度：
  1.7139 (estimate)
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2916399090
• 危险类别：
  IRRITANT
• 安全说明：
  S26,S37/39
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  应存于阴凉干燥处。

SDS

Name:	2 4-Dichloro-5-Fluoro-3-Nitrobenzoic Acid Material Safety Data Sheet
Synonym:	None Known
CAS:	106809-14-7

Section 1 - Chemical Product MSDS Name:2 4-Dichloro-5-Fluoro-3-Nitrobenzoic Acid Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
106809-14-7	2,4-Dichloro-5-Fluoro-3-Nitrobenzoic A	ca. 100	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea.
Inhalation:
Causes respiratory tract irritation. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

---

Section 4 - FIRST AID MEASURES
Eyes: Immediately 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. Wash mouth out with 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:
Treat symptomatically and supportively.

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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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

---

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. 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:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 106809-14-7: 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:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C7H2Cl2FNO4
Molecular Weight: 254

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents, carbon dioxide, acids, acid chlorides, acetic anhydride.
Hazardous Decomposition Products:
Hydrogen chloride, nitrogen oxides, carbon monoxide, carbon dioxide, hydrogen fluoride gas.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 106809-14-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2,4-Dichloro-5-Fluoro-3-Nitrobenzoic Acid - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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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: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Not regulated as a hazardous material.

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 106809-14-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 106809-14-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 106809-14-7 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质：淡黄色粉末，熔点为191-194℃。

反应信息

• 作为反应物：
  描述：

  2,4-二氯-5-氟-3-硝基苯甲酸 在 氢气 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 3-氨基-2,4-二氯-5-氟苯甲酸
  参考文献：
  名称：

  Process for the preparation of benzoic acid derivatives

  摘要：

  一种制备式子为##STR1##的化合物的方法，其中X.sup.1和X.sup.2分别独立地为氯或氟，而Y为氯，溴，氟或碘，包括将式子为##STR2##的化合物经过Sandmeyer或Balz-Schiemann反应以产生式子为##STR3##的羧酸，然后将羧酸(Ia)转化为式子为##STR4##的酰氯。化合物(II)是新的，该产品是抗菌剂的已知中间体。

  公开号：

  US04851160A1
• 作为产物：
  描述：

  2,4-二氯-5-氟苯乙酮 在 硫酸 、 硝酸 作用下， 反应 3.0h， 以91%的产率得到2,4-二氯-5-氟-3-硝基苯甲酸
  参考文献：
  名称：

  一种2,4-二氯-5-氟-3-硝基苯甲酸的制备方法

  摘要：

  本发明涉及一种2,4-二氯-5-氟-3-硝基苯甲酸的制备方法，属于化工技术领域，具体属于化学合成领域。一种2,4-二氯-5-氟-3-硝基苯甲酸的制备方法，该方法使2,4-二氯-5-氟苯乙酮与发烟硝酸于浓硫酸中反应，其中，2,4-二氯-5-氟苯乙酮、发烟硝酸、浓硫酸的摩尔比为1：6～15：11～25。利用本发明提供方法制得的产品纯度高、收率高，且该方法产生的三废少、操作简单，有利于工业化。

  公开号：

  CN103922942B

文献信息

• Defluorinated Sparfloxacin as a New Photoproduct Identified by Liquid Chromatography Coupled with UV Detection and Tandem Mass Spectrometry
  作者：Michael Engler、Guido Rüsing、Fritz Sörgel、Ulrike Holzgrabe

  DOI：10.1128/aac.42.5.1151

  日期：1998.5

  Photodegradation of sparfloxacin was observed by means of high-pressure liquid chromatography with UV detection and liquid chromatography coupled with UV detection and tandem mass spectrometry (LC-MS/MS). Three products were detected. Comparison with an independently synthesized derivative of sparfloxacin revealed the structure of one product which is believed to be 8-desfluorosparfloxacin. The second product is likely to be formed by the splitting off of a fluorine and a cyclopropyl ring. Thus, photodefluorination of quinolone antibacterial agents is found and proved for the first time by LC-MS/MS.

  通过高压液相色谱联合紫外检测和液相色谱联合紫外检测和串联质谱（LC-MS/MS），观察到了斯帕氟沙星的光降解。检测到了三种产物。与独立合成的斯帕氟沙星衍生物进行比较，揭示了其中一种产物的结构，被认为是8-去氟斯帕氟沙星。第二种产物可能是通过氟和环丙基环的分裂形成的。因此，第一次通过LC-MS/MS发现并证明了喹诺酮抗菌剂的光去氟作用。
• 4-Hydroxy-quinoline-3-carboxylic
  申请人：Bayer Aktiengesellschaft

  公开号：US04870182A1

  公开（公告）日：1989-09-26

  A process for the preparation of a compound of the formula ##STR1## in which Y is a nitrile group, an ester group COOR.sup.1 or an acid amide CONR.sup.2 R.sup.3, R.sup.1, R.sup.2 and R.sup.3 each independently is hydrogen or C.sub.1 -C.sub.4 -alkyl, and R.sup.3 may also be phenyl, and X.sup.2, X.sup.3, X.sup.4 and X.sup.5 each independently is hydrogen, halogen, nitro, cyano, alkyl having 1-3 carbon atoms, alkoxy having 1-3 carbon atoms, alkylmercapto having 1-3 carbon atoms, alkylsulphonyl having 1-3 carbon atoms, or a phenylsulphonyl group which is optionally substituted in the aryl radical, comprising reacting an aminoacrylate of the formula in which X.sup.1 is halogen, a nitro group, an alkoxy, alkoxy, alkylmercapto or alkylsulphonyl group having 1-3 carbon atoms in each case, or an arylsulphonyl group, W is hydrogen or a --CH.sub.2 CH.sub.2 Z radical, Z is is a nitrile group, an ester group COOR.sup.4 or an acid amide group CONR.sup.5 R.sup.6, and R.sup.4, R.sup.5 and R.sup.6 each independently is hydrogen or C.sub.1 -C.sub.4 -alkyl, and R.sup.5 may also be phenyl, with an acid acceptor in an aprotic solvent. Some of the reactants are new, as are the products which are intermediates for antibacterially active 1-alkyl-4-quinolone-3-carboxylic acids.

  一种制备公式为##STR1##的化合物的方法，其中Y是腈基，酯基COOR.sup.1或酸酰胺基CONR.sup.2R.sup.3，R.sup.1、R.sup.2和R.sup.3各自独立地是氢或C.sub.1-C.sub.4-烷基，R.sup.3也可以是苯基，X.sup.2、X.sup.3、X.sup.4和X.sup.5各自独立地是氢、卤素、硝基、氰基、具有1-3个碳原子的烷基、具有1-3个碳原子的烷氧基、具有1-3个碳原子的烷基硫基、具有1-3个碳原子的烷基磺酰基，或者是在芳基上可选择地取代的苯基磺酰基，包括在无水溶剂中与一种酸受体反应的公式为的氨基丙烯酸酯，其中X.sup.1是卤素、硝基、烷氧基、烷氧基、具有1-3个碳原子的烷基硫基或烷基磺酰基，或者是芳基磺酰基，W是氢或-CH.sub.2 CH.sub.2 Z基团，Z是腈基，酯基COOR.sup.4或酸酰胺基CONR.sup.5R.sup.6，R.sup.4、R.sup.5和R.sup.6各自独立地是氢或C.sub.1-C.sub.4-烷基，R.sup.5也可以是苯基，与一种无水溶剂中的酸受体反应。其中一些反应物是新的，产品是抗菌活性1-烷基-4-喹啉酮-3-羧酸的中间体。
• Process for the preparation of quinolone derivatives
  申请人：——

  公开号：US20040073030A1

  公开（公告）日：2004-04-15

  This invention relates to an improved process for the preparation of quinolone drugs of the formula (I), wherein R=C 1 -C 6 alkyl, C 3 -C 6 cycloalklyl, aryl, substituted aryl, NR 1 R 2 =diarylamino, arylalkylamino, C 1 -C 6 -dialkylamino, piprazinyl, N or C alkyl (C 1 -C 6 ) substituted piperazinyl, morpholino, pyrrolidinyl, substituted pyrrolidinyl, aralkyl, substituted aralkyl etc. Some of the compounds falling within the formula (I) are ciprofloxacin, enrofloxin, pefloxacin, etc. These compounds are useful as antibacterial drugs. The process of the present invention for preparation of compound of formula (I) comprises in enhancing the reactivity of the displaceable halogen (X) in the compound of the formula (II) towards various amines of formula (III) wherein R=as defined for compound of formula (I), R 3 =COOR 6 (R 6 =C 1 -C 6 alkyl, aryl, aralkyl), nitrile a carboxamide (—CONR 7 R 8 , R 7 and R 8 =C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, aralkyl), X=Cl, Br, F; NR 1 R 2 =as defined above by introducing a nitro group ortho to the displaceable halo group and subsequently removing the nitro group in a conventional manner. The process of the present invention enhances the yield of the compound of the formula (I) and also improves the quality of the prepared compound. 1

  本发明涉及一种改进的制备喹诺酮类药物的方法，其中R=C1-C6烷基，C3-C6环烷基，芳基，取代芳基，NR1R2=二芳基氨基，芳基烷基氨基，C1-C6-二烷基氨基，哌嗪基，N或C烷基（C1-C6）取代哌嗪基，吗啉基，吡咯啉基，取代吡咯啉基，芳基烷基，取代芳基烷基等。公式（I）中的一些化合物包括环丙沙星，依诺沙星，氟氧氟沙星等。这些化合物可用作抗菌药物。本发明的制备公式（I）化合物的方法包括增强公式（II）化合物中可置换卤原子（X）对公式（III）中各种胺的反应性，其中R=如公式（I）中定义，R3=COOR6（R6=C1-C6烷基，芳基，芳基烷基），腈或羧酰胺（—CONR7R8，R7和R8=C1-C6烷基，C3-C6环烷基，芳基烷基），X=Cl，Br，F；NR1R2=如上定义，通过在可置换卤基的邻位引入硝基基团，然后以常规方式去除硝基基团。本发明的方法提高了公式（I）化合物的产量，同时提高了制备化合物的质量。
• Synthesis and Antibacterial Properties of New 8-Nitrofluoroquinolone Derivatives
  作者：Yusuf Al-Hiari、Inas Al-Mazari、Ashok Shakya、Rula Darwish、Rana Abu-Dahab

  DOI：10.3390/12061240

  日期：——

  substituted primary amine appendages at the C-7 position to give derivatives 9a-g, in which the amino group is appended to substituted benzenes or aromatic heterocycles, is part of a primary alpha-amino acid or just a simple primary aliphatic amine. This nucleophilic aromatic substitution step was a very simple procedure since the 8-nitro group of the above synthon facilitated the addition of weak nucleophiles

  这项研究的目的是制备新的8-硝基氟喹诺酮模型并研究其抗菌性能。最初的工作涉及大规模制备合成子7-氯-1-环丙基-6-氟-8-硝基-4-氧代-1,4-二氢喹啉-3-羧酸（3），然后引入取代的伯在C-7位上的胺附件得到衍生物9a-g，其中氨基被连接到取代的苯或芳族杂环上，是伯α-氨基酸的一部分，或者仅仅是简单的伯脂族胺。该亲核芳族取代步骤是非常简单的步骤，因为上述合成子的8-硝基促进了C-7处弱亲核体的添加。使用NMR，IR，EA和MS对制备的所有化合物进行完全鉴定和表征，并且与预期结构一致。制备的靶标和中间体对革兰氏阳性和/或革兰氏阴性菌株显示出令人感兴趣的抗菌活性。特别地，对甲苯胺，对氯苯胺和苯胺衍生物显示出针对金黄色葡萄球菌的良好活性，MIC范围为约2-5μg/ mL。总之，更多的亲脂基团似乎增强了对革兰氏阳性菌株的活性。
• 1,8-bridged 4-quinolone-3-carboxylic acid antibacterials
  申请人：Bayer Aktiengesellschaft

  公开号：US04725595A1

  公开（公告）日：1988-02-16

  Antibacterially active new 1,8-bridged 4-quinolone-3-carboxylic acid derivatives of the formula ##STR1## in which Y is carboxyl or a derivative thereof R.sup.1, R.sup.2, R.sup.3, R.sup.4, X.sup.1, X.sup.2 and X.sup.5 are H or various radicals, Z is O, NH, substituted NH, --CON< or --SO.sub.2 N<, m and n are 0 or 1, and A, B, D and E are CH or substituted C or up to three of them are N, and physiologically acceptable salts thereof. Novel intermediates are described as well as processes for making the intermediates and end products.

  具有抗菌活性的新型1,8-桥联4-喹啉-3-羧酸衍生物的公式为##STR1## 其中，Y为羧基或其衍生物，R1，R2，R3，R4，X1，X2和X5为H或不同的基团，Z为O，NH，取代的NH，--CON<或--SO.sub.2 N<，m和n为0或1，A，B，D和E为CH或取代的C，其中最多三个为N，以及其生理上可接受的盐。新的中间体也被描述，以及制造中间体和最终产物的过程。