丁基二异丙氧基硼烷 | 86595-32-6

• 物质功能分类: 化学试剂 - 有机试剂 - 硼烷
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 中文名称: 丁基二异丙氧基硼烷
• 英文名称: n-butyldiisopropoxyborane
• 英文别名: butyldiisopropoxyborane；(iPrO)2B(nBu)；butyl-diisopropoxy-borane；Butyl-diisopropoxy-boran；butyl-di(propan-2-yloxy)borane
• CAS: 86595-32-6
• 化学式: C₁₀H₂₃BO₂
• mdl: MFCD00010342
• 分子量: 186.102
• InChiKey: QNRNUKUCUSOJKW-UHFFFAOYSA-N

物化性质

• 沸点：
  145-147 °C746 mm Hg(lit.)
• 密度：
  0.794 g/mL at 25 °C(lit.)
• 闪点：
  85 °F
• 稳定性/保质期：
  避免使用强氧化剂

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S16,S26,S36/37/39
• 危险类别码：
  R10,R36/37/38
• WGK Germany：
  3
• 危险品运输编号：
  UN 1993 3/PG 3
• 海关编码：
  2931900090
• 储存条件：
  请将贮藏器密封保存，并存放在阴凉干燥处。确保工作环境有良好的通风或排气设施。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Butyldiisopropoxyborane
CAS-No. : 86595-32-6
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Flammable liquids (Category 3)
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Flammable. Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H226 Flammable liquid and vapour.
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R10 Flammable.
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S16 Keep away from sources of ignition - No smoking.
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36/37/39 Wear suitable protective clothing, gloves and eye/face protection.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : Diisopropyl butylboronate
Formula : C10H23BO2
Molecular Weight : 186,1 g/mol
Component Concentration
Butyldiisopropoxyborane
CAS-No. 86545-32-6 -

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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
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
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
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large
fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or
spray; solid streams of water may be ineffective. Cool all affected containers with flooding quantities of
water.
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.

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation.
Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapours accumulating to
form explosive concentrations. Vapours can accumulate in low areas.
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
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).
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid inhalation of vapour or mist.
Keep away from sources of ignition - No smoking.Take measures to prevent the build up of electrostatic
charge.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Specific end use(s)
no data available

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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
Face shield and safety glasses 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.
Body Protection
impervious clothing, 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 respirator
with multi-purpose combination (US) or type ABEK (EN 14387) 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).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: liquid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and 145 - 147 °C at 995 hPa - lit.
boiling range
g) Flash point 29 °C - closed cup
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
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 0,794 g/cm3 at 25 °C
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

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
Heat, flames and sparks.
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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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 sensitization
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
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation
May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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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
no data available
Other adverse effects
no data available

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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. Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: 1993 IMDG: 1993 IATA: 1993
UN proper shipping name
ADR/RID: FLAMMABLE LIQUID, N.O.S. (Butyldiisopropoxyborane)
IMDG: FLAMMABLE LIQUID, N.O.S. (Butyldiisopropoxyborane)
IATA: Flammable liquid, n.o.s. (Butyldiisopropoxyborane)
Transport hazard class(es)
ADR/RID: 3 IMDG: 3 IATA: 3
Packaging group
ADR/RID: III IMDG: III IATA: III
Environmental hazards
ADR/RID: no IMDG Marine Pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途：该衍生化试剂具有潜在价值，可应用于双功能团化合物的GC和GC-MS分析。

反应信息

• 作为反应物：
  描述：

  丁基二异丙氧基硼烷 在 硫酸 作用下， 生成 正丁基硼酸
  参考文献：
  名称：

  P1 Phenethyl peptide boronic acid inhibitors of HCV NS3 protease

  摘要：

  A series of peptide boronic acids containing extended, hydrophobic P1 residues was prepared to probe the shallow, hydrophobic S1 region of HCV NS3 protease. The p-trifluoromethylphenethyl P1 substituent was identified as optimal with respect to inhibitor potency for NS3 and selectivity against elastase and chymotrypsin. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00682-0
• 作为产物：
  描述：

  硼酸三异丙酯 在 正丁基锂 作用下， 以 乙醚 为溶剂， 以92-95的产率得到丁基二异丙氧基硼烷
  参考文献：
  名称：

  Brown, Herbert C.; Srebnik, Morris; Cole, Thomas E., Organometallics, 1986, vol. 5, # 11, p. 2300 - 2303

  摘要：

  DOI：

文献信息

• A facile one-pot synthesis of alkylarylcarbinols from α,α-dichloroarylmethanes and trialkylboranes in the presence of magnesium or lithium
  作者：Nan-Sheng Li、Su Yu、George W. Kabalka

  DOI：10.1016/s0022-328x(96)06722-8

  日期：1997.3

  α-Chlorobenzylmagnesium chloride or α-chlorobenzyllithium generated from α,α-dichloroarylmethane and magnesium or lithium, reacts in situ with trialkylboranes in THF at room temperature to produce the corresponding alkylarylcarbinols in good yields after oxidation with sodium perborate.

  由α，α-二氯芳基甲烷和镁或锂生成的α-氯苄基氯化镁或α-氯苄基锂在室温下与三烷基硼烷在THF中原位反应，用过硼酸钠氧化后以高收率产生相应的烷基芳基甲醇。
• Reagent-Controlled Asymmetric Homologation of Boronic Esters by Enantioenriched Main-Group Chiral Carbenoids
  作者：Paul R. Blakemore、Stephen P. Marsden、Huw D. Vater

  DOI：10.1021/ol053055k

  日期：2006.2.1

  and (S)-1-chloro-2-phenylethyllithium (26), generated in situ by sulfoxide ligand exchange from (-)-(R(S),R)-1-chloro-2-phenylethyl p-tolyl sulfoxide (8), effected the stereocontrolled homologation of boronic esters. sec-Alcohols derived from the product boronates by oxidation with basic hydrogen peroxide exhibited % ee closely approaching that of sulfoxide 8 in examples employing Li-carbenoid 26.

  [反应：参见正文]通过亚砜配体交换从原位生成的推定对映体富集类胡萝卜素物质（R）-1-氯-2-苯基乙基氯化镁（9）和（S）-1-氯-2-苯基乙基锂（26） （-）-（R（S），R）-1-氯-2-苯基乙基对甲苯基亚砜（8）实现了硼酸酯的立体控制同源性。在使用Li-类胡萝卜素26的实例中，通过用碱性过氧化氢氧化衍生自硼酸盐产物的仲醇所显示的ee百分数接近于亚砜8的百分数。
• Alkylation of α,α-dichloroarylmethane with trialkylboranes: Synthesis of alkylarylcarbinols
  作者：George W. Kabalka、Nan-Sheng Li、Su Yu

  DOI：10.1016/0040-4039(95)01870-n

  日期：1995.11

  The alkylation of α,α-dichloroarylmethane with trialkylboranes occurs readily in the presence of t-butyllithium at −78 °C. The reaction affords the corresponding alkylarylcarbinols in good yields after oxidation with sodium perborate.

  α-α-二氯芳基甲烷与三烷基硼烷的烷基化反应容易在叔丁基锂存在下于-78°C进行。用过硼酸钠氧化后，该反应以良好的产率提供相应的烷基芳基甲醇。
• Boron-Based Diastereomerism and Enantiomerism in Imine Complexes - Determination of the Absolute Configuration at Boron by CD Spectroscopy
  作者：Manfred Braun、Sebastian Schlecht、Marco Engelmann、Walter Frank、Stefan Grimme

  DOI：10.1002/ejoc.200800787

  日期：2008.11

  Boron turns out to be a stable stereogenic center in imine complexes of aryl and alkyl boronates. Diastereomerically pure complexes 7a–c are obtained from chiral imine ligands 5a,b that are derived from the amino alcohol (R)-4. The configuration at the boron atom is determined by crystal structure analyses. Racemic boronates 10a–c, available from a condensation of aryl boronic acids 6 with the achiral

  硼在芳基和烷基硼酸酯的亚胺配合物中被证明是稳定的立体中心。非对映体纯配合物 7a-c 是从手性亚胺配体 5a、b 中获得的，这些配体是从氨基醇 (R)-4 衍生而来的。硼原子的构型由晶体结构分析确定。外消旋硼酸酯 10a-c 可从芳基硼酸 6 与非手性亚胺配体 9 缩合获得，可通过 HPLC 在手性柱上分离为稳定的对映异构体。外消旋势垒 ΔG≠ 已确定为 105–115 kJ mol–1。计算和测量的 CD 光谱的比较允许明确指定对映体硼酸亚胺复合物 10a 中硼的绝对构型。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2008）
• Process for lithium mono- and diorganylborohydrides
  申请人：Aldrich-Boranes, Inc.

  公开号：US04772751A1

  公开（公告）日：1988-09-20

  Improved processes for liberating boronic, RB(OR').sub.2, and borinic, RR'BOR', esters from their "ate" complexes, free of alcohol are provided. Pyrolysis of lithium organylborates LiRB(OR').sub.3 and LiRR'BOR', wherein R is an organyl group and R' is straight or branched-chain lower alkyl, directly yields the relatively volatile boronic and borinic esters in high purity, leaving behind a residue of lithium alkoxide. Treatment of the lithium organylborates with an appropriate acid halide cleanly liberates either volatile or non-volatile boronic or borinic esters, readily separated from the lower alkyl ester produced as a by-product. The novel compound lithium dimethylborohydride is also provided.

  提供了从其“ate”络合物中解放出无醇的硼酸酯，RB（OR'）2和硼烷酯，RR'BOR'的改进过程。锂有机硼酸盐LiRB（OR'）3和LiRR'BOR'的热解，其中R是有机基团，R'是直链或支链低级烷基，直接产生相对挥发性的高纯度硼酸酯和硼烷酯，留下锂烷氧化物残留物。用适当的酸卤处理锂有机硼酸盐可以干净地释放出挥发性或非挥发性的硼酸酯或硼烷酯，并容易与产生的低级烷基酯副产物分离。还提供了新型化合物锂二甲基硼氢化物。