(溴二氟甲基)三苯基溴化磷 | 58201-66-4

• 物质功能分类: 化学试剂 - 有机试剂 - 含磷化合物
• 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: (溴二氟甲基)三苯基溴化磷
• 中文别名: (溴二氟甲基)三苯基溴化膦
• 英文名称: (bromodifluormethyl)triphenylphosphonium bromide
• 英文别名: (bromodifluoromethyl)triphenylphosphonium bromide；[bromo(difluoro)methyl]-triphenylphosphanium;bromide
• CAS: 58201-66-4
• 化学式: Br*C₁₉H₁₅BrF₂P
• 分子量: 472.107
• InChiKey: LLFPAYWKPAHZHA-UHFFFAOYSA-M

物化性质

• 熔点：
  179-184 °C
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 安全说明：
  S24/25
• 储存条件：
  存于阴凉干燥处

SDS

Name:	(Bromodifluoromethyl)triphenylphosphonium bromide 97% Material Safety Data Sheet
Synonym:	None
CAS:	58201-66-4

Section 1 - Chemical Product MSDS Name:(Bromodifluoromethyl)triphenylphosphonium bromide 97% Material Safety Data Sheet
Synonym:None

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
58201-66-4	(Bromodifluoromethyl)triphenylphosphon	97	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

---

Section 4 - FIRST AID MEASURES
Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid.
Skin:
In case of contact, flush skin with plenty of water. Remove contaminated clothing and shoes. Get medical aid if irritation develops and persists. Wash clothing before reuse.
Ingestion:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

---

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. This material in sufficient quantity and reduced particle size is capable of creating a dust explosion.
Extinguishing Media:
Use extinguishing media most appropriate for the surrounding fire.

---

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.

---

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 breathing dust.
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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 58201-66-4: 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 minimize contact with skin.
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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: white
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 179-184 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C19H15Br2F2P
Molecular Weight: 472.12

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Dust generation, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of phosphorus, irritating and toxic fumes and gases, carbon dioxide, hydrogen fluoride gas, hydrogen bromide.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 58201-66-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(Bromodifluoromethyl)triphenylphosphonium bromide - 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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 58201-66-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 58201-66-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 58201-66-4 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：

  (溴二氟甲基)三苯基溴化磷 在 溴 作用下， 以 乙腈 为溶剂， 以59%的产率得到Bromodifluoromethyl-triphenylphosphonium tribromide
  参考文献：
  名称：

  Bender; Wulff-Molder; Vogt, Zeitschrift fur Naturforschung, B: Chemical Sciences, 2000, vol. 55, # 2, p. 167 - 170

  摘要：

  DOI：
• 作为产物：
  描述：

  (triphenylphosphonio)difluoroacetate 在 溴 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以72%的产率得到(溴二氟甲基)三苯基溴化磷
  参考文献：
  名称：

  二氟亚甲基磷酸甜菜碱与以杂原子为中心的亲电子试剂的相互作用

  摘要：

  通过使二氟亚甲基膦甜菜碱与卤化试剂以及芳基亚硫基和芳基硒烯基氯化物反应，可获得一系列二氟化phospho盐。该反应通过使磷酸甜菜碱脱羧，然后通过以杂原子为中心的亲电子试剂捕集二氟化磷叶立德而进行。通过X射线衍射分析研究了salts盐的晶体结构。对于含有CF 2 I基团和碘化物抗衡离子的盐，I = I相互作用在固态下被确认。通过量子化学计算来评估该卤素键的性质。

  DOI：

  10.1016/j.jfluchem.2019.02.008

文献信息

• Visible-Light-Induced Hydrodifluoromethylation of Alkenes with a Bromodifluoromethylphosphonium Bromide
  作者：Qing-Yu Lin、Xiu-Hua Xu、Ke Zhang、Feng-Ling Qing

  DOI：10.1002/anie.201509282

  日期：2016.1.22

  Bromodifluoromethylphosphonium bromide was solely used as the precursor of difluorocarbene. Herein, an unprecedented visible‐light‐induced hydrodifluoromethylation of alkenes with bromodifluoromethylphosphonium bromide using H2O and THF as hydrogen sources for the synthesis of difluoromethylated alkanes is described. This difluoromethylation is characterized by mild reaction conditions, ready availability

  溴化二氟甲基溴化solely仅用作二氟卡宾的前体。本文描述了前所未有的可见光诱导的烯烃加氢溴化二氟甲基methyl化氢加氢二氟甲基化反应，使用H 2 O和THF作为氢源合成二氟甲基化的烷烃。这种二氟甲基化的特点是反应条件温和，试剂容易获得以及出色的官能团耐受性。
• Preparation and synthetic utility of fluorinated phosphonium salts, -phosphonium salts and phosphoranium salts [1]
  作者：Donald J. Burton

  DOI：10.1016/s0022-1139(00)81218-x

  日期：1983.10

  fluorohalomethanes provides a rapid and high yield synthesis of various types of fluorinated phosphonium salts, bis-phosphonium salts and phosphoranium salts. These salts are useful precursors to fluorine-containing ylides, carbenes and methide ions. Examples of the preparation, mechanism of formation, and synthetic utility of these novel reagents is described.

  叔膦与氟代卤甲烷的反应提供了各种类型的氟化phospho盐，双-盐和phosphor盐的快速且高产率的合成。这些盐是有用的含氟烷基化物，卡宾和甲基离子的前体。描述了这些新型试剂的制备，形成机理和合成效用的实例。
• Substituted imidazo[1,5-A][1,2,4]triazolo[1,5-D][1,4]benzodiazepine derivatives
  申请人：Buettelmann Bernd

  公开号：US20060128691A1

  公开（公告）日：2006-06-15

  The present invention is concerned with substituted imidazo[1,5-a][1,2,4]triazolo[1,5-d][1,4]benzodiazepine derivatives of the formula I wherein R 1 is hydrogen, halogen, lower alkyl, lower alkyl substituted by halogen, lower alkoxy, lower alkoxy substituted by halogen, nitro, cycloalkyl, —O(CH 2 ) m O(CH 2 ) m OH or —C≡C—R′; R 2 is hydrogen or methyl; R 3 is lower alkyl, lower alkyl substituted by halogen, lower alkenyl, lower alkenyl substituted by halogen, lower alkynyl, —(CH 2 ) n -cycloalkyl, —(CR′R″) m —CH 3 , phenyl that is unsubstituted or substituted by halogen, pyridinyl or thienyl each of which is unsubstituted or substituted by lower alkyl, —(CH 2 ) n —NH-cycloalkyl, lower alkenyl-cycloalkyl, lower alkynyl-(CR′R″) m OH, or lower alkynyl-phenyl wherein the phenyl ring is unsubstituited or substituted by halogen, CF 3 , lower alkyl or lower alkoxy; R′ is hydrogen or lower alkyl; R″ is hydrogen, hydroxy or lower alkyl; n is 0, 1 or 2; m is 1, 2 or 3 ; and o is 1 or 2; and pharmaceutically acceptable acid addition salts thereof. This class of compounds have high affinity and selectivity for GABA A α 5 receptor binding sites. Thus, the invention also relates to methods of enhancing cognition and treating cognitive disorders like Alzheimer's disease.

  本发明涉及公式I的取代咪唑[1,5-a][1,2,4]三唑[1,5-d][1,4]苯二氮杂环己烷衍生物，其中R1为氢、卤素、较低烷基、被卤素取代的较低烷基、较低烷氧基、被卤素取代的较低烷氧基、硝基、环烷基、—O(CH2)mO(CH2)mOH或—C≡C—R′；R2为氢或甲基；R3为较低烷基、被卤素取代的较低烷基、较低烯基、被卤素取代的较低烯基、较低炔基、—(CH2)n-环烷基、—(CR′R″)m—CH3、苯基（未取代或被卤素取代）、吡啶基或噻吩基，每种基未取代或被较低烷基取代、—(CH2)n—NH-环烷基、较低烯基-环烷基、较低炔基-(CR′R″)mOH或较低炔基-苯基，其中苯环未取代或被卤素、CF3、较低烷基或较低烷氧基取代；R′为氢或较低烷基；R″为氢、羟基或较低烷基；n为0、1或2；m为1、2或3；o为1或2；及其药学上可接受的酸盐。这类化合物对GABA A α5受体结合位点具有高亲和力和选择性。因此，该发明还涉及增强认知和治疗像阿尔茨海默病这样的认知障碍的方法。
• Organic Colorant Complexes from Reactive Dyes and Articles Containing the Same
  申请人：Milliken & Company

  公开号：US20150299468A1

  公开（公告）日：2015-10-22

  An organic colorant complex with the following general structure: AB n (DE) m T x Q y wherein A is an organic chromophore; B is an electrophilic reactive group covalently bonded to A directly or through a linking group; D is a nucleophilic linking group covalently bonding B and E, selected from the group consisting of NR, O, S, and 4-oxyanilino (—HN-Ph-O—); wherein R is selected from the group consisting of H, alkyl, aryl, and E; E is an organic alkyl and aryl group or an end group; T is an ionic group covalently linked to A; O is an organic cation, bonded to the organic chromophore A through ionic interaction with T; n, m, x, and y are independent integers from 1 to 10.

  具有以下一般结构的有机着色剂复合物：ABn(DE)mTxQy其中A是有机色团；B是与A直接或通过连接基团共价键合的亲电性反应基团；D是共价键合B和E的亲核连接基团，选自NR、O、S和4-氧基苯胺基（—HN-Ph-O—）组成的群；其中R选自H、烷基、芳基和E组成的群；E是有机烷基和芳基或末端基团；T是与A共价连接的离子基团；O是有机阳离子，通过与T的离子相互作用与有机色团A结合；n、m、x和y是独立的1至10之间的整数。
• Synthetic and mechanistic aspects of the reactions between bromodifluoromethyltriphenylphosphonium bromide and dibromofluoromethyltriphenylphosphonium bromide and trialkylphosphites
  作者：Richard M. Flynn、Donald J. Burton、Denise M. Wiemers

  DOI：10.1016/j.jfluchem.2008.04.003

  日期：2008.7

  exchange process involves the formation of difluorocarbene via   dissociation of the intermediate difluoromethylene ylide, capture of the difluorocarbene by the trialkylphosphite to give [(RO)3P+CF2−], which captures bromine followed by dealkylation to the product, bromodifluoromethylphosphonate. The equilibria involved in the multi-step mechanism are all shifted to the phosphonate product by the final dealkylation

  溴氟甲基三苯基溴化in以两种不同的方式与亚磷酸三烷基酯反应。溴代二氟甲基三苯基phosph与亚磷酸三烷基酯进行快速交换反应，以良好或极好的收率得到相应的溴代二氟甲基膦酸酯。用类似的二乙氧基苯基亚膦酸酯也发生类似的交换反应，得到相应的乙氧基苯基亚膦酸酯。从机理上讲，交换过程包括通过  中间体二氟亚甲基叶立德的离解形成二氟卡宾，亚磷酸三烷基酯捕获二氟卡宾以生成[（RO）3P + CF2-]，它捕获溴，然后脱烷基化为产物溴二氟甲基膦酸酯。通过最后的脱烷基步骤，多步机理中涉及的平衡都转化为膦酸酯产物。相反，二溴氟甲基三苯基溴化does不与亚磷酸三烷基酯进行交换反应。亚磷酸酯用作卤化试剂，从二溴氟甲基phosph盐中提取溴，生成溴氟亚甲基叶立德，其很容易被醛或酮原位捕获，从而获得高收率的E / Z-溴代氟烯烃。没有观察到溴氟亚甲基叶立德的解离。