3,5-dibromo-4-hydroxy-benzaldehyde-oxime | 25952-74-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3,5-dibromo-4-hydroxy-benzaldehyde-oxime
• 英文别名: 3,5-Dibrom-4-hydroxy-benzaldehyd-oxim；3,5-Dibrom-4-hydroxy-benzaldoxim；2,6-Dibromo-4-[(hydroxyamino)methylidene]cyclohexa-2,5-dien-1-one；2,6-dibromo-4-(hydroxyiminomethyl)phenol
• CAS: 25952-74-3
• 化学式: C₇H₅Br₂NO₂
• 分子量: 294.93
• InChiKey: UVKQTDFYDUQTKK-UHFFFAOYSA-N

物化性质

• 熔点：
  198 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  12
• 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：
  52.8
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2928000090

SDS

Name:	3 5-Dibromo-4-hydroxybenzaldehyde oxime 97% Material Safety Data Sheet
Synonym:
CAS:	25952-74-3

Section 1 - Chemical Product MSDS Name:3 5-Dibromo-4-hydroxybenzaldehyde oxime 97% Material Safety Data Sheet
Synonym:

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
25952-74-3	3,5-Dibromo-4-hydroxybenzaldehyde oxim	97%	unlisted

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

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

---

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.
Ingestion:
Get medical aid. 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.
Notes to Physician:
Treat symptomatically and supportively.

---

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.
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.

---

Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a tightly closed container. Store in a dry area. Keep refrigerated. (Store below 4C/39F.)

---

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# 25952-74-3: Personal Protective Equipment Eyes: Not available.
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: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 198 - 201 deg C
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: C7H5Br2NO2
Molecular Weight: 295

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Acids, bases, oxidizing agents, reducing agents, acid chlorides.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, hydrogen bromide, bromine.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 25952-74-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3,5-Dibromo-4-hydroxybenzaldehyde oxime - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

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

---

Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

---

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# 25952-74-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 25952-74-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 25952-74-3 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3,5-dibromo-4-hydroxy-benzaldehyde-oxime 在 三氟甲磺酸酐 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以85%的产率得到溴苯腈
  参考文献：
  名称：

  三苯基膦-三氟甲磺酸酐的核磁共振研究和亲电性能；出色的脱水剂系统，可将醛肟转化为腈

  摘要：

  NMR研究了三苯基膦与各种量的三氟甲磺酸酐在0°C下的反应。通过将1.3当量的Ph 3 P与Tf 2混合而形成的试剂结构已经建立了O（1.0mmol）作为平衡混合物，其主要由三氟甲烷亚磺酸三苯基（三氟甲基磺酰氧基）phosph和三氟甲烷亚磺酸盐相应的双（三苯基）氧二phosph二聚体组成。该系统的亲电特性已被用于开发将醛肟转化为腈的温和方法中。脱水是在0°C的非常温和的条件下进行的，首先激活肟氧，然后用碱处理，然后消除三苯膦氧化物。探索了该有用方法的底物范围和官能团耐受性。

  DOI：

  10.1016/j.tetlet.2010.01.119
• 作为产物：
  描述：

  3,5-二溴-4-羟基苯甲醛 在 吡啶 、 盐酸羟胺 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 3,5-dibromo-4-hydroxy-benzaldehyde-oxime
  参考文献：
  名称：

  钌催化的水中醛糖肟重排为伯酰胺

  摘要：

  醛肟于伯酰胺的重排已使用容易获得的芳烃-钌（II）络合物将[RuCl研究2（η 6 -C 6我6）{P（NME 2）3 }]（5摩尔％）作为催化剂。反应在纯水中于100°C干净地进行，无需任何助催化剂的帮助，在较短的反应时间（1-7小时）后，以高收率（70-90％）得到所需的酰胺。该方法对芳香族，杂芳香族，α，β-不饱和和脂肪族醛肟均有效，并能耐受多个官能团。使用18的反应曲线和实验O标记的水表明在这些转化中涉及两种不同的机制。在两者中，腈中间体最初都是通过醛肟的脱水而形成的。然后通过醛肟或水的第二分子的作用将这些中间体水合为相应的酰胺。还讨论了苯甲醛肟重排成苯甲酰胺的动力学分析。

  DOI：

  10.1021/om3006917

文献信息

• Cyclic Aromatic Analogues of the Hendrickson Reagent; NMR Studies and Electrophilic Properties
  作者：Ziad Moussa

  DOI：10.1055/s-0031-1289998

  日期：2012.2

  in the conversion of aldoximes into nitriles. The dehydration occurred rapidly at room temperature and produced high yields with a variety of alkyl- and arylaldoximes, tolerating a wide range of substrates and functional groups. 1,2-bis(diphenylphosphino)benzene - 1,2-bis(diphenylphosphoryl)benzene - trifluoromethanesulfonic anhydride - ­Hendrickson reagent - dehydration - aldoximes - nitriles

  Hendrickson'POP'试剂的两个新型环状芳香族类似物1,1,3,3-四苯基-1,3-二氢-2,1,3-苯并恶二磷-1,3-二（双氟甲烷磺酸盐）和双（三氟甲烷磺酸盐）通过用二氯甲烷中的三氟甲磺酸酐分别处理1，2-双（二苯基膦基）苯或1，2-双（二苯基磷酰基）苯，可以很容易地制得）。³¹ P和¹9F NMR研究表明，虽然形成了后者的络合物​​作为唯一产物，但显示出前者是与1-（二苯基膦基）-2- [二苯基（三氟甲基磺酰氧基）膦基]苯三氟甲烷亚磺酸盐和1,2平衡的主要成分。 -双[二苯基（三氟甲基磺酰氧基）膦基]苯双（三氟甲亚磺酸盐）。脱水的“ POP”系统被用于将醛肟转化为腈。脱水在室温下迅速发生，并产生高收率的多种烷基和芳基醛肟，可耐受各种底物和官能团。 1,2-双（二苯基膦基）苯-1,2-双（二苯基磷酰基）苯-三氟甲磺酸酐-亨德里克森试剂-脱水-醛肟-腈
• Oxime ethers and pesticidal preparations containing them
  申请人：Ciba-Geigy AG

  公开号：US03941839A1

  公开（公告）日：1976-03-02

  New oxime ethers and pesticidal and herbicidal preparations containing them are disclosed. The oxime ethers correspond to the formula ##SPC1## Wherein R.sub.1 is a hydrogen atom or a lower alkyl radical; R.sub.2 is an aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radical; or wherein R.sub.1 and R.sub.2 form part of a saturated or unsaturated carbocycle or a 5-, 6- or 7-membered heterocycle; R.sub.3 is a nitro, trifluoromethyl, formyl, lower carbalkoxy, sulfamyl or mono- or di-lower alkyl sulfamyl radical; R.sub.4.sub.- and R.sub.5.sub.- each is a hydrogen or halogen atom, an amino, mono- or di-lower alkyl amino, lower alkoxy, cycloalkoxy, lower alkylthio, nitro, lower carbalkoxy, arylthio, lower aralkylthio or lower alkyl group, or 5-, 6- or 7-membered heterocycle.

  揭示了新的肟醚化合物和含有它们的杀虫剂和除草剂制剂。这些肟醚化合物对应于以下结构式：其中R1为氢原子或较低的烷基基团；R2为脂肪族、环脂肪族、芳基脂肪族、芳香族或杂环基团；或者R1和R2构成饱和或不饱和的碳环或5、6或7元杂环的一部分；R3为硝基、三氟甲基、甲酰基、较低的羰基烷氧基、磺胺基或单或双较低的烷基磺胺基基团；R4和R5分别为氢或卤素原子、氨基、单或双较低的烷基氨基、较低的烷氧基、环烷氧基、较低的烷基硫氧基、硝基、较低的羰基烷氧基、芳基硫氧基、较低的芳基烷基硫氧基或较低的烷基基团，或者为5、6或7元杂环。
• Paal; Kromschroeder, Chemische Berichte, 1895, vol. 28, p. 3236
  作者：Paal、Kromschroeder

  DOI：——

  日期：——
• Ruthenium-Catalyzed Rearrangement of Aldoximes to Primary Amides in Water
  作者：Rocío García-Álvarez、Alba E. Díaz-Álvarez、Javier Borge、Pascale Crochet、Victorio Cadierno

  DOI：10.1021/om3006917

  日期：2012.9.10

  The rearrangement of aldoximes to primary amides has been studied using the readily available arene-ruthenium(II) complex [RuCl2(η6-C6Me6)P(NMe2)3}] (5 mol %) as catalyst. Reactions proceeded cleanly in pure water at 100 °C without the assistance of any cocatalyst, affording the desired amides in high yields (70–90%) after short reaction times (1–7 h). The process was operative with both aromatic

  醛肟于伯酰胺的重排已使用容易获得的芳烃-钌（II）络合物将[RuCl研究2（η 6 -C 6我6）P（NME 2）3 }]（5摩尔％）作为催化剂。反应在纯水中于100°C干净地进行，无需任何助催化剂的帮助，在较短的反应时间（1-7小时）后，以高收率（70-90％）得到所需的酰胺。该方法对芳香族，杂芳香族，α，β-不饱和和脂肪族醛肟均有效，并能耐受多个官能团。使用18的反应曲线和实验O标记的水表明在这些转化中涉及两种不同的机制。在两者中，腈中间体最初都是通过醛肟的脱水而形成的。然后通过醛肟或水的第二分子的作用将这些中间体水合为相应的酰胺。还讨论了苯甲醛肟重排成苯甲酰胺的动力学分析。
• NMR Studies and electrophilic properties of triphenylphosphine–trifluoromethanesulfonic anhydride; a remarkable dehydrating reagent system for the conversion of aldoximes into nitriles
  作者：Ziad Moussa、Saleh A. Ahmed、Ahmad S. ElDouhaibi、Shaya Y. Al-Raqa

  DOI：10.1016/j.tetlet.2010.01.119

  日期：2010.4

  NMR Studies on the reaction of triphenylphosphine with various amounts of triflic anhydride at 0 °C is described. The reagent structure resulting from mixing 1.3 equiv of Ph3P with Tf2O (1.0 mmol) has been established as an equilibrium mixture consisting mainly of triphenyl(trifluoromethylsulfonyloxy)phosphonium trifluoromethanesulfinate and the corresponding bis(triphenyl)oxodiphosphonium trifluoromethanesulfinate

  NMR研究了三苯基膦与各种量的三氟甲磺酸酐在0°C下的反应。通过将1.3当量的Ph 3 P与Tf 2混合而形成的试剂结构已经建立了O（1.0mmol）作为平衡混合物，其主要由三氟甲烷亚磺酸三苯基（三氟甲基磺酰氧基）phosph和三氟甲烷亚磺酸盐相应的双（三苯基）氧二phosph二聚体组成。该系统的亲电特性已被用于开发将醛肟转化为腈的温和方法中。脱水是在0°C的非常温和的条件下进行的，首先激活肟氧，然后用碱处理，然后消除三苯膦氧化物。探索了该有用方法的底物范围和官能团耐受性。