N-Boc-(甲苯磺酰)甲胺 | 433335-00-3

• 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: N-Boc-(甲苯磺酰)甲胺
• 中文别名: N-Boc-（甲苯磺酰基）甲胺；N-BOC-(甲苯磺酰)甲胺
• 英文名称: N-Boc-(tosyl)methylamine
• 英文别名: tert-butyl N-[(4-methylphenyl)sulfonylmethyl]carbamate
• CAS: 433335-00-3
• 化学式: C₁₃H₁₉NO₄S
• 分子量: 285.364
• InChiKey: WJECUHBEAHRZPC-UHFFFAOYSA-N

物化性质

• 熔点：
  115-119 °C
• 沸点：
  455.1±45.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• WGK Germany：
  3
• 危险品标志：
  Xn
• 海关编码：
  2924299090

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : N-Boc-(tosyl)methylamine
CAS-No. : 433335-00-3
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]
Acute toxicity, Oral (Category 4)
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
Harmful if swallowed. Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
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)
R22 Harmful if swallowed.
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36/37 Wear suitable protective clothing and gloves.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : tert-Butyl tosylmethylcarbamate
(Toluene-4-sulfonylmethyl)carbamic acid, tert-butyl ester
N-Boc-(p-tosyl)methanamine
Formula : C13H19NO4S
Molecular Weight : 285,36 g/mol
Component Concentration
N-Boc-(tosyl)methylamine
CAS-No. 433335-00-3 -

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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
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
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
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
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.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Store under inert gas.
Specific end uses
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
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.
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
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
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: solid
Colour: white
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 115 - 119 °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- log Pow: 2,222
octanol/water
p) Autoignition 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
no data available
Incompatible materials
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
Prolonged or repeated exposure may cause allergic reactions in certain sensitive individuals. The
preceding data, or interpretation of data, was determined using Quantitative Structure Activity Relationship
(QSAR) modeling.
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 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
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material. 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: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
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
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
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
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
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

反应信息

• 作为反应物：
  描述：

  N-Boc-(甲苯磺酰)甲胺 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.08h， 生成 diethyl N-(tert-butoxycarbonyl)aminomethylphosphonate
  参考文献：
  名称：

  N -Boc-1-氨基烷基膦酸二乙酯的快速一锅法合成

  摘要：

  已经开发了N -Boc-1-氨基烷基膦酸二乙酯的一般的一锅式，无提纯的合成方法。该方法包括在氢化氢对四氢呋喃中的α-酰胺基烷基-对甲苯砜的作用下，将碱式亚磷酸二乙酯钠的Michael催化加成到N- Boc亚胺中。

  DOI：

  10.1016/s0040-4039(01)02289-4
• 作为产物：
  描述：

  对甲基苯磺酰甲基异腈 、 叔丁醇 在 碘 、 二甲基亚砜 作用下， 以82%的产率得到N-Boc-(甲苯磺酰)甲胺
  参考文献：
  名称：

  DMSO 中碘介导的醇和 TosMIC 中氨基甲酸酯的有效直接获取

  摘要：

  报道了一种由碘/DMSO 系统促进的由醇和 TosMIC 合成氨基甲酸酯的新方法。该方法为在温和条件下快速构建氨基甲酸酯提供了一种一步、直接和实用的策略。该反应通过异氰化物顺序氧化为异氰酸酯和醇与异氰酸酯的亲核加成以高产率提供氨基甲酸酯而进行。

  DOI：

  10.1055/s-0037-1610229

文献信息

• Synthesis and antiproliferative activity of novel α- and β-dialkoxyphosphoryl isothiocyanates
  作者：Mateusz Psurski、Katarzyna Błażewska、Anna Gajda、Tadeusz Gajda、Joanna Wietrzyk、Józef Oleksyszyn

  DOI：10.1016/j.bmcl.2011.05.113

  日期：2011.8

  A series of 15 mostly new dialkoxyphosphoryl alkyl and aralkyl isothiocyanates were synthesized using two alternative strategies, and their in vitro antiproliferative activity against several cancer cell lines (including drug resistant) is here demonstrated. The IC50 values measured for the new compounds are within the range of 6.3–21.5 μM, and they are quite similar to the activity of two best and

  使用两种替代策略合成了一系列15种大部分为新的二烷氧基磷酰基烷基烷基和芳烷基异硫氰酸酯，并在此证明了它们对几种癌细胞系（包括耐药性）的体外抗增殖活性。对新化合物测得的IC 50值在6.3-21.5μM的范围内，与两种最佳，研究最广泛的天然异硫氰酸苄酯（A）和异硫氰酸苯乙酯（B）的活性非常相似。）。初步研究利用细胞周期和使用代表性化合物对A549肺癌细胞系进行的还原型谷胱甘肽水平分析发现，其作用机理可能存在重要差异，可能与其化学性质有关。疏水性化合物主要与还原的胞质谷胱甘肽反应，导致其耗尽，从而导致氧化应激并将细胞周期阻滞在G0 / G1期。另一方面，亲水性化合物会导致中度的细胞周期停滞和大量的细胞死亡，与中度减少的谷胱甘肽耗竭有关。这些表明异硫氰酸酯的化学结构的显着变化是可能的，这不会导致抗增殖活性的显着变化，但同时引起作用机理的差异。
• Arginase Inhibitors and Their Therapeutic Applications
  申请人：OncoArendi Therapeutics S.A.

  公开号：US20170319536A1

  公开（公告）日：2017-11-09

  Disclosed are small molecule therapeutic compounds that are potent inhibitors of arginase 1 and arginase 2 activity. Also disclosed are pharmaceutical compositions comprising the compounds, and methods for using the compounds for treating or preventing a disease or condition associated with arginase activity.

  揭示了一种小分子治疗化合物，它们是较强的精氨酸酶1和精氨酸酶2活性抑制剂。还揭示了包含这些化合物的药物组合物，以及使用这些化合物治疗或预防与精氨酸酶活性相关的疾病或状况的方法。
• A Short and Scalable Synthesis of Orthogonally Protected Bis(aminomethyl)malonic Acid: Access to Bioactive Macrocyclic Peptides
  作者：Muthalagu Vetrichelvan、Vijayabhaskar Bokkala、Surendran Renganathan、Arvind Mathur、Richard Rampulla、Anuradha Gupta

  DOI：10.1055/s-0036-1588505

  日期：2017.11

  and scalable process for the preparation of multi-gram quantities of orthogonally protected bis(aminomethyl)malonic acid in good yield from readily available starting material is described. These orthogonally protected amino acids are important building blocks to make peptides based drugs, glycoconjugates, and in the total synthesis of peptide natural products. The newly developed route has only six

  摘要 描述了一种短程且可扩展的方法，该方法用于从容易获得的起始原料中以高收率制备数克量的正交保护的双（氨基甲基）丙二酸。这些正交保护的氨基酸是制造基于肽的药物，糖结合物以及在肽天然产物的总合成中的重要组成部分。新开发的路线只有六个步骤，总产率为27％，这是关键步骤之一，其中丙二酸对酰亚胺的亲核攻击。 描述了一种短程且可扩展的方法，该方法用于从容易获得的起始原料中以高收率制备数克量的正交保护的双（氨基甲基）丙二酸。这些正交保护的氨基酸是制造基于肽的药物，糖结合物以及在肽天然产物的总合成中的重要组成部分。新开发的路线只有六个步骤，总产率为27％，这是关键步骤之一，其中丙二酸对酰亚胺的亲核攻击。
• New access to racemic β3-amino acids
  作者：Michał Nejman、Anna Śliwińska、Andrzej Zwierzak

  DOI：10.1016/j.tet.2005.04.077

  日期：2005.8

  A general simple procedure having the potential for large scale preparations of racemic β3-amino acids has been developed. The procedure involves base-catalyzed Michael-type addition of sodium diethyl malonate to N-Boc-α-amidoalkyl-p-tolyl sulfones in tetrahydrofuran. Hydrolysis of the adducts by refluxing with 6 M aqueous hydrochloric acid affords β3-amino acid hydrochlorides in high yield and excellent

  具有用于外消旋β大规模制备的潜在的一般简单的程序3 -氨基酸已经研制成功。该方法包括在四氢呋喃中将碱式催化的丙二酸二乙酯钠的迈克尔型加成到N -Boc-α-酰氨基烷基-对甲苯基砜中。通过用6M盐酸水溶液，得到回流加合物的水解β 3吨以高收率和优异的纯度α-氨基酸盐酸盐。
• Transition metal-free selective C–S bond cleavage of Ugi-adducts for rapid preparation of peptidomimetics
  作者：Chao Liu、Liangliang Song、Vsevolod A. Peshkov、Erik V. Van der Eycken

  DOI：10.1039/d1gc04421d

  日期：——

  A transition metal-free C–S bond cleavage and subsequent Mannich reaction of Ugi-adducts with alcohols as well as thiols is developed. Diverse novel peptidomimetics containing N,O- or N,S-aminals are synthesized in a rapid, highly efficient and step-economical fashion. This method features exclusive selectivity, broad substrate scope, excellent yield and functional group tolerance, and was applied

  开发了 Ugi 加合物与醇和硫醇的无过渡金属 C-S 键断裂和随后的 Mannich 反应。以快速、高效和分步经济的方式合成了多种含有N、O - 或N、S - 缩醛胺的新型肽模拟物。该方法具有独特的选择性、广泛的底物范围、优异的产率和官能团耐受性，适用于非布索坦、丙磺舒和美金刚衍生的底物。