N-benzylidene-1,1,1-trimethylsilanamine | 17599-61-0

• 物质功能分类: 化学试剂 - 有机试剂 - 亚氨、脒
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzylidene-1,1,1-trimethylsilanamine
• 英文别名: N-trimethylsilylbenzaldimine；N-Benzylidenetrimethylsilylamine；1-phenyl-N-trimethylsilylmethanimine
• CAS: 17599-61-0
• 化学式: C₁₀H₁₅NSi
• 分子量: 177.321
• InChiKey: ATGAAABKKYCMRZ-UHFFFAOYSA-N

物化性质

• 沸点：
  50-60 °C
• 密度：
  0.85+/-0.1 g/mL at 25 °C
• 闪点：
  49 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26
• 危险类别码：
  R10
• WGK Germany：
  2
• 危险品运输编号：
  UN 1993 3/PG 3
• 海关编码：
  2931900090
• 储存条件：
  应存放在室温、干燥、密封且充气的环境中。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : N-Trimethylsilylbenzaldimine
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. : 17599-61-0
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
Flammable liquids (Category 3), H226
Skin irritation (Category 2), H315
Eye irritation (Category 2), H319
Specific target organ toxicity - single exposure (Category 3), Respiratory system, H335
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
Xi Irritant R10, R36/37/38
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 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 vapours.
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
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : (Benzylidene)(trimethylsilyl)amine
Formula : C10H15NSi
Molecular Weight : 177,32 g/mol
CAS-No. : 17599-61-0
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
N-Trimethylsilylbenzaldimine
Flam. Liq. 3; Skin Irrit. 2; Eye -
Irrit. 2; STOT SE 3; H226,
H315, H319, H335
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
N-Trimethylsilylbenzaldimine
Xi, R10 - R36/37/38 -
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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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
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

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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, nitrogen oxides (NOx), silicon 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 vapours, 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.
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
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.
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. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Handle and store under inert gas. Air and moisture sensitive.
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

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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 AXBEK (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).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.

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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 50 - 60 °C
boiling range
g) Flash point 48,9 °C
h) Evapouration 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 1,444 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
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
Heat, flames and sparks.
Incompatible materials
Strong oxidizing agentsStrong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

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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 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
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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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
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
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.
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. (N-Trimethylsilylbenzaldimine)
IMDG: FLAMMABLE LIQUID, N.O.S. (N-Trimethylsilylbenzaldimine)
IATA: Flammable liquid, n.o.s. (N-Trimethylsilylbenzaldimine)
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

反应信息

• 作为反应物：
  描述：

  N-benzylidene-1,1,1-trimethylsilanamine 在 盐酸 、 4-二甲氨基吡啶 、 正丁基锂 、 四丁基氟化铵 、 sodium hydride 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 61.42h， 生成 paclitaxel
  参考文献：
  名称：

  β-内酰胺合成子法高效合成紫杉醇及其C-13侧链类似物的新方法

  摘要：

  高效手性酯烯酸酯-亚胺缩合可产生具有优异对映体纯度的3-羟基-4-芳基-β-内酰胺，已成功用于对映体纯紫杉醇C-13侧链N-苯甲酰基-（2 R， 3 S）-3-苯基-异丝氨酸及其类似物。易于衍生自3-羟基-4-苯基-β-内酰胺的（3 R，4 S）-N-苯甲酰基-3-（1-乙氧基乙氧基）-4-苯基-2-氮杂环丁酮与受保护的浆果赤霉素III偶联，然后通过脱保护得到光学纯的紫杉醇和高产率的10-脱乙酰基7,10-双（Troc）-紫杉醇。完全分配的1 H，13显示并讨论了由此合成的紫杉醇的C和2D（COSY和HETCOR）NMR光谱。

  DOI：

  10.1016/s0040-4020(01)91210-4
• 作为产物：
  描述：

  六甲基二硅氮烷 在 正丁基锂 、 苯甲醛 作用下， 以 正己烷 为溶剂， 以92%的产率得到N-benzylidene-1,1,1-trimethylsilanamine
  参考文献：
  名称：

  Process for the stereoselective preparation of a .beta.-phenylisoserine

  摘要：

  这项发明涉及一种立体选择性制备β-苯基异丝氨酸衍生物的方法，通过在受保护的羟基乙酸酰胺的手性活性酰胺（III）上作用具有式（II）的N-羰基苄亚胺，然后水解所得产物。在式（I）、（II）或（III）中，R是可选择取代的苯基基团或R.sub.1--O，Ar是可选择取代的芳基基团，G.sub.1是羟基保护基团。式（I）的产物在制备紫杉醇和紫杉醇脱氧酸时特别有用，这两者具有显著的抗肿瘤性能。

  公开号：

  US05726346A1
• 作为试剂：
  描述：

  N-benzylidenebenzamide 、 在 N-benzylidene-1,1,1-trimethylsilanamine 、 双氧水 、 sodium hydroxide 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 30.0h， 以79%的产率得到(3R,4S)-6-phenylhex-1-ene-3,4-diol
  参考文献：
  名称：

  1,5的对映选择性和选择性合成顺式- （Z ^通过亚胺双Allylboration） -氨基醇：合成反式1,2,3,6-四氢吡啶和Andrachcine的全合成

  摘要：

  描述了反式-1,2,3,6-四氢吡啶8的立体选择性合成。这种合成经由1,5-分子内Mistunobu反应所得顺式（ - Ž） -氨基醇7，其通过醛的高度diastereo-和不对称双allylboration反应制备5和silylimine 6。手性双官能γ-borylallylborane 9 Ë由丙二烯的硼氢化原位产生3与（diisopinocampheyl）硼烷4。该策略已应用于雄激素1的全合成，因此可以确定天然产品的绝对和相对构型。

  DOI：

  10.1021/acs.orglett.7b00995

文献信息

• Copper-catalyzed synthesis of allenylboronic acids. Access to sterically encumbered homopropargylic alcohols and amines by propargylboration
  作者：Jian Zhao、Sybrand J. T. Jonker、Denise N. Meyer、Göran Schulz、C. Duc Tran、Lars Eriksson、Kálmán J. Szabó

  DOI：10.1039/c7sc05123a

  日期：——

  ketones and imines without any additives. Catalytic asymmetric propargylborylation of ketones is demonstrated with high stereoselectivity allowing for the synthesis of highly enantioenriched tertiary homopropargyl alcohols. The reaction is suitable for kinetic resolution of racemic allenylboronic acids affording alkynes with adjacent quaternary stereocenters.

  三取代和四取代的丙二烯基硼酸是通过一种新的多功能铜催化方法制备的。密集官能化的丙二烯基硼酸很容易与酮和亚胺发生炔丙基硼化反应，无需任何添加剂。酮的催化不对称炔丙基硼化反应具有高立体选择性，可以合成高度对映体富集的叔均炔丙醇。该反应适用于外消旋丙二烯基硼酸的动力学拆分，得到具有相邻四元立构中心的炔烃。
• Highly Selective Allylborations of Aldehydes Using α,α-Disubstituted Allylic Pinacol Boronic Esters
  作者：Matthew J. Hesse、Stéphanie Essafi、Charlotte G. Watson、Jeremy N. Harvey、David Hirst、Christine L. Willis、Varinder K. Aggarwal

  DOI：10.1002/anie.201402995

  日期：2014.6.10

  α‐Disubstituted allylic pinacol boronic esters undergo highly selective allylborations of aldehydes to give tetrasubstituted homoallylic alcohols with exceptional levels of anti‐Z‐selectivity (>20:1). The scope of the reaction includes both acyclic and cyclic allylic boronic esters which lead to acyclic and exocyclic tetrasubstituted homoallylic alcohols. The use of β‐borylated allylic boronic esters gave fully

  α，α-二取代烯丙基频哪醇硼酸酯经历的高选择性allylborations醛，得到四取代的高烯丙醇与特殊水平的抗- ž -选择性（> 20：1）。反应范围包括产生无环和环外四取代均烯丙基醇的无环和环状烯丙基硼酸酯。使用β-硼化的烯丙基硼酸酯得到带有硼酸酯的完全取代的烯烃，该酯经过进一步的交叉偶联，从而实现了高度模块化和立体选择性的方法合成二芳基四取代的烯烃。计算分析揭示了观察到的显着选择性的起源。
• Silyl Imine Electrophiles in Enantioselective Catalysis: A Rosetta Stone for Peptide Homologation, Enabling Diverse <i>N</i>-Protected Aryl Glycines from Aldehydes in Three Steps
  作者：Dawn M. Makley、Jeffrey N. Johnston

  DOI：10.1021/ol501297a

  日期：2014.6.6

  es serve in the Bis(AMidine)-catalyzed addition of bromonitromethane with a high degree of enantioselection. This allows for the production of a range of protected α-bromo nitroalkane donors (including Fmoc) for use in Umpolung Amide Synthesis (UmAS). Hence, peptide homologation with nonnatural aryl glycine amino acids is achieved in three steps from aromatic aldehydes, which are plentiful and inexpensive

  我们报告N -（三甲基甲硅烷基）亚胺在双（脒）催化的溴硝基甲烷加成中发挥作用，具有高度的对映选择性。这允许生产一系列受保护的 α-溴硝基烷烃供体（包括 Fmoc），用于 Umpolung 酰胺合成 (UmAS)。因此，与非天然芳基甘氨酸氨基酸的肽同源性是通过三个步骤从芳香醛中实现的，芳香醛丰富且价格低廉。通过避免α-氨基酸中间体，可以避免同源步骤中的差向异构化。
• Access to Nitriles from Aldehydes Mediated by an Oxoammonium Salt
  作者：Christopher B. Kelly、Kyle M. Lambert、Michael A. Mercadante、John M. Ovian、William F. Bailey、Nicholas E. Leadbeater

  DOI：10.1002/anie.201412256

  日期：2015.3.27

  route to access an array of nitriles from aldehydes mediated by an oxoammonium salt (4‐acetylamino‐2,2,6,6‐tetramethylpiperidine‐1‐oxoammonium tetrafluoroborate) and hexamethyldisilazane (HMDS) as an ammonia surrogate has been developed. The reaction likely involves two distinct chemical transformations: reversible silyl‐imine formation between HMDS and an aldehyde, followed by oxidation mediated by the

  一种可扩展，高产，快速的途径，可通过乙氧基铵盐（4-乙酰氨基-2-2,2,6,6-四甲基哌啶-1-氟肟酸四氟硼酸）和六甲基二硅氮烷（HMDS）介导的醛类中的一系列腈的进入已经被开发出来。该反应可能涉及两个不同的化学转化：HMDS和醛之间可逆的甲硅烷基亚胺形成，然后由氧铵盐介导的氧化和甲硅烷基化反应制得腈。废氧化剂可以容易地回收并用于再生氧铵盐氧化剂。
• Lithium-<i>N</i>-lithiomethyldithiocarbamate: Neue<i>N</i>-Alkylaminomethylanion-Äquivalente; III¹. 2-Imidazolidinthione and 1,2-Diamine durch eletrophile Aminoalkylierung mit Iminen und Immoniumsalzen
  作者：Hubertus Ahlbrecht、Christine Schmitt

  DOI：10.1055/s-1994-25556

  日期：——

  Lithium N-Lithiomethyldithiocarbamates: New N-Alkylaminomethyl Anion Equivalents; III.1 2-Imidazolidinethiones and 1, 2-Diamines via Electrophilic Aminoalkylation with Imines and Iminium Salts Treatment of lithium N-butyl-N-lithiomethyldithiocarbamates 3 with various aldimines and ketimines 4 leads to 1,3,4, 4-tetrasubstituted 2-imidazolidinethiones 6. If iminium salts 7 are used as electrophiles, unsymmetrically substituted 1,2-diamines 8 are obtained.

  锂N-甲基二硫代氨基甲酸锂：新型的N-烷胺甲基阴离子等价物；第三部分。1 通过亚胺和亚胺盐的亲电子氨基烷基化合成2-咪唑啉酮和1,2-二胺。将锂N-丁基-N-甲基二硫代氨基甲酸锂3与各种醛亚胺和酮亚胺4反应，得到了1,3,4,4-四取代的2-咪唑啉酮6。如果使用亚胺盐7作为亲电子试剂，则得到不对称取代的1,2-二胺8。