2,4,6-三异丙基苯磺酰叠氮化物 | 36982-84-0

• 物质功能分类: 化学试剂 - 有机试剂 - 叠氮
• 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: 2,4,6-三异丙基苯磺酰叠氮化物
• 中文别名: 2,4,6-三异丙基苯磺酰基叠氮化物；2,4,6-三异丙基苯磺酰叠氮
• 英文名称: 2,4,6-Triisopropylbenzenesulfonyl azide
• 英文别名: Trisyl azide；N-diazo-2,4,6-triisopropylbenzenesulfonamide；(NE)-N-diazo-2,4,6-tri(propan-2-yl)benzenesulfonamide
• CAS: 36982-84-0
• 化学式: C₁₅H₂₃N₃O₂S
• 分子量: 309.433
• InChiKey: AEMWUHCKKDPRSK-UHFFFAOYSA-N

物化性质

• 熔点：
  39-44 °C
• 闪点：
  4℃
• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）
• 稳定性/保质期：

  常规情况下不会分解，也没有危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  56.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  T,Xn,F
• 安全说明：
  S15,S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2929909090
• 危险标志：
  GHS02,GHS07,GHS08
• 危险性描述：
  H225,H302,H304,H315,H336,H361d,H373
• 危险性防范说明：
  P210,P261,P281,P301 + P310,P331
• 储存条件：
  密封、阴凉、干燥、通风保存

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 2,4,6-Triisopropylbenzenesulfonyl azide
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. : 36982-84-0
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
Acute toxicity, Oral (Category 3), H301
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
T Toxic R25
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)
H301 Toxic if swallowed.
Precautionary statement(s)
P280 Wear protective gloves/ protective clothing/ eye protection/ face
protection.
P301 + P310 IF SWALLOWED: Immediately call a POISON CENTER or doctor/
physician.
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : 2,4,6-Triisopropylphenylsulfonyl azide
2,4,6-Tris(1-methylethyl)-benzenesulfonyl azide
Formula : C15H23N3O2S
Molecular Weight : 309,43 g/mol
CAS-No. : 36982-84-0
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
2,4,6-Triisopropylbenzenesulfonyl azide
Self-react. B; Acute Tox. 3; -
H241, H301
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
2,4,6-Triisopropylbenzenesulfonyl azide
T, R 5 - R25 -
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. Take victim immediately to hospital. Consult a physician.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
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), Sulphur oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Wear respiratory protection. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate
ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
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
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
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 formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
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.
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
Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling
the product.
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
Complete suit protecting against chemicals, 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 N99 (US) or type P2 (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.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 39 - 44 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
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 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

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SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Contains the following stabiliser(s):
Water (<15 %)
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong 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 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
no data available
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
Offer surplus and non-recyclable solutions to a licensed disposal company. Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: 2811 IMDG: 2811 IATA: 2811
UN proper shipping name
ADR/RID: TOXIC SOLID, ORGANIC, N.O.S. (2,4,6-Triisopropylbenzenesulfonyl azide)
IMDG: TOXIC SOLID, ORGANIC, N.O.S. (2,4,6-Triisopropylbenzenesulfonyl azide)
IATA: Toxic solid, organic, n.o.s. (2,4,6-Triisopropylbenzenesulfonyl azide)
Transport hazard class(es)
ADR/RID: 6.1 IMDG: 6.1 IATA: 6.1
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：

• 实现功能化糖类Meyer′s内酰胺化反应的高度立体选择性和各向异性合成
• 合成试剂：用于炭疽菌致命性中毒作用的解毒剂
• 细菌性RNA聚合酶抑制剂
• 双环扩展的二肽替代物
• 单个对映异构体分歧杆菌keomycolic酸

反应信息

• 作为反应物：
  描述：

  2,4,6-三异丙基苯磺酰叠氮化物 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 以84%的产率得到(4S)-3-[(S)-2-Azidohex-4-enoyl]-4-(phenylmethyl)-2-oxazolidinone
  参考文献：
  名称：

  Compounds for inhibiting &bgr;-amyloid peptide release and/or its synthesis

  摘要：

  揭示了一些抑制β-淀粉样肽释放和/或其合成的化合物，因此在治疗阿尔茨海默病方面具有用途。还揭示了包括抑制β-淀粉样肽释放和/或其合成的化合物的药物组合物。

  公开号：

  US06207710B1
• 作为产物：
  描述：

  2,4,6-三异丙基苯磺酰基肼 在 亚硝酸特丁酯 作用下， 以 乙腈 为溶剂， 反应 0.25h， 以85%的产率得到2,4,6-三异丙基苯磺酰叠氮化物
  参考文献：
  名称：

  亚硝酸叔丁酯介导的氮转移反应：室温下苯并三唑和叠氮化物的合成

  摘要：

  的A转换ö苯二胺为苯并三唑类是用在室温下实现叔丁基亚硝酸盐。优化的条件也非常适合将磺酰基和酰基肼转化为相应的叠氮化物。该协议不需要任何催化剂或酸性介质。在短时间内以优异的产率获得了所需的产物。

  DOI：

  10.1039/c8ob01950a
• 作为试剂：
  描述：

  3-氯-1-茚满-5-基-丙-1-酮 在 硫酸 、 2,4,6-三异丙基苯磺酰叠氮化物 、 sodium hydride 、 caesium carbonate 、 potassium nitrate 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 115.5h， 生成 4-(2-(2-(5-bromo-3-(3,5-dibromo-4-hydroxybenzylidene)-2-oxoindolin-1-yl)ethoxy)ethoxy)-N-((1,2,3,5,6,7-hexahydro-s-indacen-4-yl)carbamoyl)benzenesulfonamide
  参考文献：
  名称：

  10.1016/j.ejmech.2024.116581

  摘要：

  DOI：

  10.1016/j.ejmech.2024.116581

文献信息

• Iridium(III)-Catalyzed Selective Sulfonamidation of<i>o</i>-Carborane with Sulfonyl Azide by Carboxylic Acid-Assisted B(4)-H Bond Activation
  作者：Huanhuan Li、Fan Bai、Hong Yan、Changsheng Lu、Vladimir I. Bregadze

  DOI：10.1002/ejoc.201601537

  日期：2017.3.10

  An IrIII‐catalyzed direct cage B(4)–H bond sulfonamidation with carboxylic acid assistance is reported. This reaction proceeds in the absence of both external oxidants and ligands, and shows high yields and good functional group tolerance. In particular, direct cage B(4)–H bond amination was achieved by using aryl and aliphatic azides as nitrenoid sources for the first time.

  据报道，在羧酸的辅助下，Ir III催化的直接笼状B（4）-H键磺酰胺化反应。该反应在不存在外部氧化剂和配体的情况下进行，并且显示出高产率和良好的官能团耐受性。特别是，首次通过使用芳基和脂肪族叠氮化物作为类固醇源来实现直接笼状B（4）-H键胺化。
• Synthesis of 3-Pyrrolin-2-ones by Rhodium-Catalyzed Transannulation of 1-Sulfonyl-1,2,3-triazole with Ketene Silyl Acetal
  作者：Rui-Qiao Ran、Jun He、Shi-Dong Xiu、Kai-Bing Wang、Chuan-Ying Li

  DOI：10.1021/ol501514b

  日期：2014.7.18

  α-Imino rhodium carbenoids generated from 1-sulfonyl 1,2,3-triazole were applied to the 3 + 2 cycloaddition with ketene silyl acetal, offering a novel and straightforward synthesis of biologically interesting compound 3-pyrrolin-2-one with broad substrate scope.

  由1-磺酰基1,2,3-三唑生成的α-氨基铑类胡萝卜素与乙烯酮甲硅烷基缩醛应用于3 + 2环加成反应，提供了一种新颖而直接的合成方法，可合成具有广泛底物的生物学上令人感兴趣的化合物3-吡咯啉-2-酮范围。
• Synthesis of Cyclic Amidines from Quinolines by a Borane-Catalyzed Dearomatization Strategy
  作者：Vinh Do Cao、So Hwa Mun、Seo Ha Kim、Gyeong Un Kim、Hyung Guk Kim、Seewon Joung

  DOI：10.1021/acs.orglett.9b04275

  日期：2020.1.17

  herein is the development of a new synthetic route to cyclic amidines from quinolines. The borane-catalyzed 1,4-hydrosilylation of quinoline was utilized for the dearomatization of the quinolines. The dearomatized enamine intermediate was subsequently reacted with a broad range of organic azides to produce the corresponding cyclic amidines (3,4-dihydroquinolinimines) via a [3 + 2] cycloaddition pathway

  本文描述了从喹啉向环am的新合成路线的开发。硼烷催化的喹啉的1，4-氢化硅烷化被用于喹啉的脱芳香化。随后将脱芳香化的烯胺中间体与各种有机叠氮化物反应，以通过[3 + 2]环加成途径生成相应的环状am（3,4-二氢喹啉亚胺）。初步的机理研究表明，在环加成反应中涉及到氢化物的转变。
• 一种芳基磺酰叠氮的微通道合成方法
  申请人：河南智心通生物科技有限公司

  公开号：CN109824556A

  公开（公告）日：2019-05-31

  本发明公开一种芳基磺酰叠氮的微通道合成方法，将叠氮化钠与水搅拌均匀配成物料A，芳基磺酰氯与丙酮搅拌均匀配成物料B，通过连续进料的方式，将物料A与物料B分别以6mL/min~70mL/min的流速输入微通道反应器进行高效反应，制备芳基磺酰叠氮。相对于现有技术，本发明的工艺路线操作安全、转化率高、节约成本，且芳基磺酰叠氮的产率大于80%。
• Rhodium( <scp>II</scp> )‐Catalyzed [4+3] Cyclization of Triazoles with Indole Derivatives and Its Application in the Total Synthesis of (±)‐Aurantioclavine
  作者：Shengguo Duan、Bing Xue、Hui Meng、Zihang Ye、Ze‐Feng Xu、Chuan‐Ying Li

  DOI：10.1002/cjoc.202000657

  日期：2021.5

  rhodium(II)‐catalyzed [4+3] cyclization reaction of 1‐sulfonyl‐1,2‐3‐triazoles and indoles was developed. Azepino[5,4,3‐ cd]indoles, which are widely distributed in ergot alkaloids with various biological activities, could be obtained in good to excellent yields. In addition, the total synthesis of (±)‐aurantioclavine was completed in four steps from the known compound 1a adopting this [4+3] cyclization as a key step

  开发了有效的铑（II）催化的1-磺酰基-1,2-3-3三唑和吲哚的[4 + 3]环化反应。可以以良好或极好的收率获得阿斯皮诺[5,4,3- cd ]吲哚，广泛分布在具有各种生物活性的麦角生物碱中。此外，采用这种[4 + 3]环化作为关键步骤，从已知化合物1a的四个步骤中完成了（±）-金葡糖醇的总合成。