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三苯基硼烷 | 960-71-4

中文名称
三苯基硼烷
中文别名
三苯硼[烷];三苯基硼
英文名称
triphenylborane
英文别名
BPh3;triphenylboron
三苯基硼烷化学式
CAS
960-71-4
化学式
C18H15B
mdl
MFCD00003007
分子量
242.128
InChiKey
MXSVLWZRHLXFKH-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    145 °C (lit.)
  • 沸点:
    203 °C/15 mmHg (lit.)
  • 密度:
    0.898 g/mL at 25 °C
  • 闪点:
    1 °F
  • 物理描述:
    Liquid
  • 稳定性/保质期:
    在常温常压下稳定,避免与水分和空气接触以防止氧化。

计算性质

  • 辛醇/水分配系数(LogP):
    5.91
  • 重原子数:
    19
  • 可旋转键数:
    3
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.0
  • 拓扑面积:
    0
  • 氢给体数:
    0
  • 氢受体数:
    0

ADMET

毒理性
  • 副作用
生殖毒素 - 对生殖系统有毒的化学物质,包括对后代缺陷以及损伤男性和女性生殖功能的毒性。生殖毒性包括发育影响。参见生殖毒性风险评估指南。
Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment.
来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
毒理性
  • 毒性数据
LC50 (大鼠) = 73 毫克/立方米/4小时
LC50 (rat) = 73 mg/m3/4hr
来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

安全信息

  • TSCA:
    No
  • 危险等级:
    4.1
  • 危险品标志:
    Xn,F
  • 安全说明:
    S16,S22,S24/25,S26,S33,S36
  • 危险类别码:
    R36/37/38,R19,R11
  • WGK Germany:
    3
  • RTECS号:
    ED2367500
  • 海关编码:
    2931900090
  • 包装等级:
    III
  • 危险类别:
    4.1
  • 危险标志:
    GHS02,GHS07,GHS08
  • 危险品运输编号:
    UN 1993 3/PG 2
  • 危险性描述:
    H225,H302,H319,H335,H351
  • 危险性防范说明:
    P210,P280,P301 + P312 + P330,P305 + P351 + P338,P370 + P378,P403 + P235
  • 储存条件:
    存储在干燥的惰性气体中,并确保容器密封良好。应将其存放在阴凉、干燥的地方。

SDS

SDS:7f2a0ff702a9c0737f801265414e35a5
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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Triphenylborane
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 960-71-4


SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Flammable solids (Category 1), H228
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
F Highly flammable R11
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Danger
Hazard statement(s)
Flammable solid.
Precautionary statement(s)
Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
Supplemental Hazard none
Statements
Other hazards - none

SECTION 3: Composition/information on ingredients
Substances
Formula : C18H15B
Molecular Weight : 242,12 g/mol
CAS-No. : 960-71-4
EC-No. : 213-504-2
No components need to be disclosed according to the applicable regulations.
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Do NOT induce vomiting. Never give anything by mouth to an unconscious person. Rinse mouth with
water. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Borane/boron oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
Use water spray to cool unopened containers.

SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Remove all
sources of ignition. Evacuate personnel to safe areas.
For personal protection see section 8.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Contain spillage, and then collect with an electrically protected vacuum cleaner or
by wet-brushing and place in container for disposal according to local regulations (see section 13). Keep
in suitable, closed containers for disposal. Contain spillage, pick up with an electrically protected vacuum
cleaner or by wet-brushing and transfer to a container for disposal according to local regulations (see
section 13).
Reference to other sections
For disposal see section 13.

SECTION 7: Handling and storage
Precautions for safe handling
Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.Keep away from sources of ignition
- No smoking.Take measures to prevent the build up of electrostatic charge.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Air sensitive.
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Full contact
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
test method: EN374
If used in solution, or mixed with other substances, and under conditions which differ from EN 374,
contact the supplier of the CE approved gloves. This recommendation is advisory only and must
be evaluated by an industrial hygienist and safety officer familiar with the specific situation of
anticipated use by our customers. It should not be construed as offering an approval for any
specific use scenario.
Body Protection
Flame retardant antistatic protective clothing, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face particle
respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering
controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use
respirators and components tested and approved under appropriate government standards such
as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.

SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid, powder
Colour: beige
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 145 °C - lit.
point
f) Initial boiling point and 203 °C at 20 hPa - lit.
boiling range
g) Flash point no data available
h) Evapouration rate no data available
i) Flammability (solid, gas) The substance or mixture is a flammable solid with the category 1.
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
Heat, flames and sparks. Extremes of temperature and direct sunlight.
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: ED2367500
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

SECTION 13: Disposal considerations
Waste treatment methods
Product
Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting
as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal
company.
Contaminated packaging
Dispose of as unused product.

SECTION 14: Transport information
UN number
ADR/RID: 1325 IMDG: 1325 IATA: 1325
UN proper shipping name
ADR/RID: FLAMMABLE SOLID, ORGANIC, N.O.S. (Triphenylborane)
IMDG: FLAMMABLE SOLID, ORGANIC, N.O.S. (Triphenylborane)
IATA: Flammable solid, organic, n.o.s. (Triphenylborane)
Transport hazard class(es)
ADR/RID: 4.1 IMDG: 4.1 IATA: 4.1
Packaging group
ADR/RID: II IMDG: II IATA: II
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

SECTION 15: Regulatory information
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
Further information
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any


SECTION 16 - ADDITIONAL INFORMATION
N/A


制备方法与用途

概述

三苯基硼烷可用作医药合成中间体。如果吸入三苯基硼烷,请将患者移至新鲜空气处;若皮肤接触,应脱去污染衣物,并用肥皂水和清水彻底清洗受污染部位,如有不适请就医;若眼睛接触,需分开眼睑并使用流动清水或生理盐水冲洗,随后立即就医;如误食,请漱口并禁止催吐,务必立即就医。

用途

三苯基硼烷不仅可用作医药合成中间体,还可用于制备一种船舶专用低表面能防污涂料、无金属的硼掺杂炭材料过氧化氢电还原催化剂以及航空皮革坐垫和金属涂料等。

分类
  • 类别:有毒物品
  • 毒性分级:高毒
  • 急性毒性(口服):
    • 大鼠 LD50: 196 毫克/公斤
  • 刺激数据
    • 眼睛(兔):110 毫克/24小时,重度刺激
可燃性危险特性

遇热、明火燃烧;火灾现场会释放硼化物辛辣刺激烟雾。

储运特性

需存放在通风、低温和干燥的库房中,并保持防潮。应将三苯基硼烷与食品及氧化剂分开存放和运输。

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    三苯基硼烷四乙基硼酸钠 作用下, 以 xylene 为溶剂, 生成 四苯硼钠
    参考文献:
    名称:
    Grassberger,M.A.; Koester,R., Angewandte Chemie, 1969, vol. 81, p. 261
    摘要:
    DOI:
  • 作为产物:
    描述:
    四苯硼钠 在 HCl 作用下, 以 乙腈 为溶剂, 生成 三苯基硼烷
    参考文献:
    名称:
    Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Na: SVol.3, 3.7, page 1233 - 1245
    摘要:
    DOI:
  • 作为试剂:
    描述:
    三苯基硼烷 作用下, 以 四氢呋喃 为溶剂, 生成
    参考文献:
    名称:
    混合较重 Sn=Ge 亚乙烯基中的双 1,2-碳迁移
    摘要:
    双1,2-碳迁移使得亚锡亚烷基异构化为亚亚锗亚烷基。理论研究表明异构化过程涉及碳硼烷基和芳基的逐步迁移。反应性研究表明,在用IMe 4处理后,亚锡亚锡经历了有趣的电子重新分布,生成甲亚砜-亚锡加合物,并且很容易与(AlCp*) 4反应,得到独特的异核铝基锡亚锡。
    DOI:
    10.1002/anie.202401570
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文献信息

  • Nickel-catalyzed Conjugate Addition of Arylboron Reagents to α,β-Unsaturated Carbonyl Compounds with the Aid of a Catalytic Amount of an Alkyne
    作者:Eiji Shirakawa、Yuichi Yasuhara、Tamio Hayashi
    DOI:10.1246/cl.2006.768
    日期:2006.7
    Alkynes in combination with a catalytic amount of a nickel complex were found to catalyze the conjugate addition of arylboron reagents to α,β-unsaturated carbonyl compounds, where use of an optical...
    发现炔烃与催化量的镍络合物结合可催化芳基硼试剂与 α,β-不饱和羰基化合物的共轭加成,其中使用光学...
  • Ring-opening of Epoxides Mediated by Frustrated Lewis Pairs
    作者:Tetiana Krachko、Emmanuel Nicolas、Andreas W. Ehlers、Martin Nieger、J. Chris Slootweg
    DOI:10.1002/chem.201801909
    日期:2018.8.27
    studies, the mechanism of these reactions was found to proceed via activation of the epoxide by the Lewis acidic borane moiety followed by nucleophilic attack of the phosphine of a second FLP molecule. The resulting chain‐like intermediates afford the final cyclic products by ringclosure and concurrent release of the second equivalent of FLP that behaves as catalyst in this reaction.
    用2-甲基环氧乙烷,2-苯基环氧乙烷和2-甲基环氧乙烷处理t Bu 2 PCH 2 BPh 2(1)和o- Ph 2 P(C 6 H 4)BCat(Cat = catechol)(4) 2-(三氟甲基)环氧乙烷导致环氧化物开环,分别生成六元和七元杂环2 a – c和5 a – c。这些两性离子产物进行光谱表征,和化合物2,图2b,5和通过单晶X射线结构分析对5 c进行了结构表征。基于计算和动力学研究,发现这些反应的机理是通过路易斯酸性硼烷部分激活环氧化物,然后亲核攻击第二个FLP分子的膦来进行的。最终的链状中间体通过闭环并同时释放第二个等效的FLP(在该反应中起催化剂作用)而提供最终的环状产物。
  • Deaggregation of Zinc Dihydride by Lewis Acids Including Carbon Dioxide in the Presence of Nitrogen Donors
    作者:Florian Ritter、Louis J. Morris、Karl N. McCabe、Thomas P. Spaniol、Laurent Maron、Jun Okuda
    DOI:10.1021/acs.inorgchem.1c02207
    日期:2021.10.18
    complexes show an exchange with free BPh3 as well as [HBPh3]−. DFT calculations suggest the presence of [HBPh3]− anion with a highly polarized B–H bond that interacts with the Lewis acidic zinc hydride cation [(L2)Zn(H)]+. The hydridotriphenylborates [(Ln)Zn(H)(HBPh3)] underwent CO2 insertion to give (formato)zinc (formoxy)triphenylborate complexes [(Ln)Zn(OCHO)][(OCHO)BPh3] (Ln = TMPDA, PMDTA, Me4TACD)
    热敏聚合二氢化锌[ZnH 2 ] n可以方便地通过ZnEt 2与[AlH 3 (NEt 3 )]反应制备。当在螯合 N-供体配体 L n = N , N , N ', N '-四甲基乙二胺(TMEDA), N , N , N ', N '-四甲基-1存在下与 CO 2 (1 bar)反应时, 3-丙二胺 (TMPDA)、N,N,N',N",N'' -五甲基二亚乙基三胺 (PMDTA) 和 1,4,7,10-四甲基-1,4,7,10-四氮杂环十二烷 (Me 4TACD),很容易插入到 Zn-H 键中。根据齿数n,甲酸盐 [(L n )Zn(OCHO) 2 ] 被分离并在结构上进行表征,无论是作为分子 (L n = TMEDA、TMPDA、PMDTA) 还是电荷分离的离子对 [(L n ) Zn(OCHO)][OCHO] (L n = Me 4 TACD)。[ZnH 2 ] n与温和的路易斯酸
  • Revisiting the 1,2,4-Triaza-3,5-diborolyl Ligand:  σ and π Coordination Modes in the Alkali Metal and Rhodium Complexes of a Planar, 6-π-Electron B<sub>2</sub>N<sub>3</sub><sup>-</sup> Ring
    作者:Hanh V. Ly、Joanna H. Chow、Masood Parvez、Robert McDonald、Roland Roesler
    DOI:10.1021/ic7013286
    日期:2007.10.1
    precursor 1. The alkali metal derivatives were characterized by multinuclear NMR, mass spectrometry, and single-crystal X-ray diffraction. The structural determinations revealed extended 2D structures for 2a and 2b and an extended 1D structure for 2c. All three solvent-free structures are dominated by sigma interactions, and pi interactions are also present for the potassium derivative. Addition of triphenylborane
    1-甲基-3,5-二苯基-4-甲基氨基-1,2,4-三氮杂-3,5-二硼烯丙基的锂(2a),钠(2b)和钾(2c)盐是通过将其去质子化而制得的中性前体1中的环氮。通过多核NMR,质谱和单晶X射线衍射对碱金属衍生物进行了表征。结构确定显示2a和2b的扩展2D结构和2c的扩展1D结构。所有三个无溶剂结构均以sigma相互作用为主,并且钾衍生物也存在pi相互作用。将三苯基硼烷加到2a,2b和2c中分别生成加合物3a,3b和3c,并通过多核NMR和质谱对其进行表征。已经对锂盐和钾盐进行了结构确定,表明Ph3B配位在环的2位,而碱金属则被侧基甲基氨基配位。锂离子还由3a的单体结构中的三个乙腈分子配位,而钾离子由3个苯基的配位结构,形成3c的一维聚合物结构。2a与[Rh(cod)Cl] 2的反应生成二聚体4,该二聚体4包含两个1,2,4-三氮杂3,5-二硼烯丙基环,该两个桥环通过无取代基的环氮原子桥接两个Rh(cod)片段。
  • Transition‐Metal‐Free Oxidative Cross‐Coupling of Tetraarylborates to Biaryls Using Organic Oxidants
    作者:Carolin Gerleve、Armido Studer
    DOI:10.1002/anie.202002595
    日期:2020.9
    tetraarylborates undergo selective (cross)‐coupling through oxidation with Bobbitt's salt to give symmetric and unsymmetric biaryls. The organic oxoammonium salt can be used either as a stoichiometric oxidant or as a catalyst in combination with in situ generated NO2 and molecular oxygen as the terminal oxidant. For selected cases, oxidative coupling is also possible with NO2/O2 without any additional
    容易制备的四芳基硼酸盐通过用博比特盐氧化进行选择性(交叉)偶联,得到对称和不对称的联芳基化合物。有机氧铵盐可用作化学计量氧化剂或与原位产生的NO 2和作为末端氧化剂的分子氧组合用作催化剂。对于某些情况,也可以使用 NO 2 /O 2进行氧化偶联,无需任何额外的氮氧自由基助催化剂。四芳基硼酸盐的无过渡金属催化氧化配体交叉偶联是前所未有的,所引入的方法提供了获得各种联芳基和杂联芳基系统的途径。
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表征谱图

  • 氢谱
    1HNMR
  • 质谱
    MS
  • 碳谱
    13CNMR
  • 红外
    IR
  • 拉曼
    Raman
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mass
cnmr
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  • 峰位数据
  • 峰位匹配
  • 表征信息
Shift(ppm)
Intensity
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