4-(2-氨基保护羧基)苯甲酸 | 214475-53-3

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 其他氨基酸衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: 4-(2-氨基保护羧基)苯甲酸
• 英文名称: 4-(Fmoc-hydrazino)-benzoic acid
• 英文别名: 4-(2-Fmoc-hydrazino)benzoic acid；4-[2-(9H-fluoren-9-ylmethoxycarbonyl)hydrazinyl]benzoic acid
• CAS: 214475-53-3
• 化学式: C₂₂H₁₈N₂O₄
• 分子量: 374.396
• InChiKey: MLVJMSRGLQCZDE-UHFFFAOYSA-N

物化性质

• 密度：
  1.363±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  29280000
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338
• 储存条件：
  2-8°C

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 4-(2-Fmoc-hydrazino)benzoic acid
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. : 214475-53-3

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Skin irritation (Category 2), H315
Eye irritation (Category 2), H319
Specific target organ toxicity - single exposure (Category 3), 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 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)
Causes skin irritation.
Causes serious eye irritation.
May cause respiratory irritation.
Precautionary statement(s)
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
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Formula : C22H18N2O4
Molecular Weight : 374,39 g/mol
CAS-No. : 214475-53-3
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
4-(2-Fmoc-hydrazino)benzoic acid
CAS-No. 214475-53-3 Skin Irrit. 2; Eye Irrit. 2; STOT <= 100 %
SE 3; H315, H319, H335
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
4-(2-Fmoc-hydrazino)benzoic acid
CAS-No. 214475-53-3 Xi, R36/37/38 <= 100 %
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
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)
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 vapours, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
For personal protection see section 8.
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.
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.
Recommended storage temperature: 2 - 8 °C
Specific end use(s)
Apart 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
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
impervious 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
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).
Control of environmental exposure
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: powder
Colour: light yellow
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 no data available
boiling range
g) Flash point no data available
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 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.
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 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

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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: - 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

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-(2-氨基保护羧基)苯甲酸 在 1-羟基苯并三唑 、 苯甲醚 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 50.5h， 生成 (2S)-3-(4-chlorophenyl)-2-[[4-[2-(9H-fluoren-9-ylmethoxycarbonyl)hydrazinyl]benzoyl]amino]propanoic acid
  参考文献：
  名称：

  芳酰肼作为固相合成的连接基，可在温和的氧化条件下裂解

  摘要：

  我们已经开发了酸/碱稳定的芳基酰肼连接基，该连接基很容易与固相树脂偶联。切割是特定且容易的，需要铜（II）催化剂，碱和亲核试剂进行。该条件与所有20种蛋白原氨基酸均相容，并在20°C下2小时内完成定量切割，从而得到具有C端酸，酰胺或酯官能团的肽。芳基酰肼也可作为简单的“无痕”连接剂提供作用域。

  DOI：

  10.1016/s0040-4039(98)01543-3
• 作为产物：
  描述：

  氯甲酸-9-芴基甲酯 、 4-肼基苯甲酸 在 碳酸氢钠 作用下， 以 1,4-二氧六环 为溶剂， 以75%的产率得到4-(2-氨基保护羧基)苯甲酸
  参考文献：
  名称：

  芳酰肼作为固相合成的连接基，可在温和的氧化条件下裂解

  摘要：

  我们已经开发了酸/碱稳定的芳基酰肼连接基，该连接基很容易与固相树脂偶联。切割是特定且容易的，需要铜（II）催化剂，碱和亲核试剂进行。该条件与所有20种蛋白原氨基酸均相容，并在20°C下2小时内完成定量切割，从而得到具有C端酸，酰胺或酯官能团的肽。芳基酰肼也可作为简单的“无痕”连接剂提供作用域。

  DOI：

  10.1016/s0040-4039(98)01543-3

文献信息

• [EN] COMPOSITIONS AND METHODS FOR TARGETING METASTATIC TUMORS USING MULTIVALENT LIGAND-LINKED CARBOHYDRATE POLYMERS<br/>[FR] COMPOSITIONS ET METHODES PERMETTANT DE CIBLER DES TUMEURS METASTATIQUES A L'AIDE DE POLYMERES MULTIVALENTS CARBOHYDRATES LIES A UN LIGAND
  申请人：PRO PHARMACEUTICALS INC

  公开号：WO2005092097A1

  公开（公告）日：2005-10-06

  Disclosed herein are compositions comprising a drug linked to a multivalent ligand polysaccharide and the use of this composition in the prevention and treatment of cancer. In one aspect, the polysaccharide is obtained by physical and chemical treatment of naturally occurring polymers or semi synthetic polymers which are bridged specifically with one or more anti-cancer chemotherapeutic agents. Another aspect is directed to the effective delivery of the polysaccharide together with the chemotherapeutic agent to diseased tissue including cancerous tissue.

  本文披露了包含药物与多价配体多糖相连的组合物，以及该组合物在预防和治疗癌症中的用途。在一个方面，该多糖是通过对天然聚合物或半合成聚合物进行物理和化学处理获得的，这些聚合物特异地与一个或多个抗癌化疗药物相桥接。另一个方面涉及将多糖与化疗药物有效地输送到包括癌组织在内的患病组织。
• Beyond Basicity: Discovery of Nonbasic DENV-2 Protease Inhibitors with Potent Activity in Cell Culture
  作者：Nikos Kühl、Mila M. Leuthold、Mira A. M. Behnam、Christian D. Klein

  DOI：10.1021/acs.jmedchem.0c02042

  日期：2021.4.22

  The viral serine protease NS2B-NS3 is one of the promising targets for drug discovery against dengue virus and other flaviviruses. The molecular recognition preferences of the protease favor basic, positively charged moieties as substrates and inhibitors, which leads to pharmacokinetic liabilities and off-target interactions with host proteases such as thrombin. We here present the results of efforts

  病毒丝氨酸蛋白酶NS2B-NS3是针对登革热病毒和其他黄病毒的药物发现的有希望的靶标之一。蛋白酶的分子识别偏爱偏向于碱性，带正电荷的部分作为底物和抑制剂，这会导致药代动力学方面的问题以及与宿主蛋白酶（如凝血酶）的脱靶相互作用。我们在这里介绍了专门针对黄病毒病毒的不带电荷的小分子抑制剂的发现和开发的努力结果。发现这些化合物的关键因素是登革热蛋白酶DENV2proHeLa系统的细胞报告基因检测。广泛的结构-活性关系探索在病毒复制测定中产生了具有亚微摩尔活性的新型苯甲酰胺衍生物（EC 500.24μM），针对脱靶蛋白酶的选择性和可忽略的细胞毒性。与大多数以前公开的针对活性部位的黄病毒蛋白酶抑制剂相比，该结构类别的药物相似性增强，并且包括有望用于进一步的临床前开发的候选药物。
• Building Boron Heterocycles into DNA-Encoded Libraries
  作者：Pinwen Cai、Lukas A. Schneider、Cedric Stress、Dennis Gillingham

  DOI：10.1021/acs.orglett.1c03262

  日期：2021.11.19

  DNA-encoded library (DEL) technology uses DNA tags to track the synthetic history of individual members in a split-and-pool combinatorial synthesis scheme. DEL synthesis hinges on robust methodologies that tolerate combinatorial synthesis schemes while not destroying the information in DNA. We introduce here a DEL-compatible reaction that assembles a boron-containing pyridazine heterocycle. The heterocycle

  DNA 编码库 (DEL) 技术使用 DNA 标签来跟踪拆分和池组合合成方案中各个成员的合成历史。 DEL 合成取决于稳健的方法，该方法能够容忍组合合成方案，同时不会破坏 DNA 中的信息。我们在此介绍一种 DEL 相容反应，可组装含硼哒嗪杂环。杂环是独特的，因为它可以与醇发生可逆的共价相互作用——直到现在，这一特性还没有被刻意设计到 DEL 中
• Diagnostic and therapeutic agents
  申请人：Taube Seija

  公开号：US20070258899A1

  公开（公告）日：2007-11-08

  Tumor targeting units are disclosed which have a peptide sequence C y —Y—G-F—X—W-G-Z-C yy (SEQ ID NO: 25), or a pharmaceutically or physiologically acceptable salt thereof. Tumor targeting agents are also disclosed having at least one targeting unit, directly or indirectly coupled to at least one effector unit. Diagnostic or pharmaceutical compositions having at least one targeting unit or at least one targeting agent, and targeting units or targeting agents for the preparation of a medicament for the treatment of cancer related diseases (including cancer), especially for the treatment of colon/colorectal cancer or its metastases are also disclosed.

  揭示了具有肽序列Cy—Y—G-F—X—W-G-Z-Cyy（序列ID编号：25）或其药学或生理上可接受的盐的肿瘤靶向单元。还披露了具有至少一个靶向单元的肿瘤靶向剂，直接或间接地偶联至至少一个效应单元。还披露了具有至少一个靶向单元或至少一个靶向剂的诊断或药物组合物，以及用于制备治疗癌症相关疾病（包括癌症）的药物的靶向单元或靶向剂，特别是用于治疗结肠/结直肠癌或其转移的靶向单元或靶向剂。
• Chemoselective Copper-Mediated Modification of Selenocysteines in Peptides and Proteins
  作者：Zhenguang Zhao、Daphna Shimon、Norman Metanis

  DOI：10.1021/jacs.1c06101

  日期：2021.8.18

  Highly valuable bioconjugated molecules must be synthesized through efficient, chemoselective chemical modifications of peptides and proteins. Herein, we report the chemoselective modification of peptides and proteins via a reaction between selenocysteine residues and aryl/alkyl radicals. In situ radical generation from hydrazine substrates and copper ions proceeds rapidly in an aqueous buffer at near

  必须通过对肽和蛋白质进行有效的化学选择性化学修饰来合成高价值的生物共轭分子。在此，我们报告了通过硒代半胱氨酸残基和芳基/烷基自由基之间的反应对肽和蛋白质进行化学选择性修饰。肼底物和铜离子的原位自由基生成在接近中性 pH (5–8) 的水性缓冲液中快速进行，提供多种与芳基和烷基分子缀合的硒修饰的线性和环状肽和蛋白质，以及亲和标记标签（生物素）。这种化学为化学蛋白质修饰开辟了一条新途径。