3-[(二甲氨基)甲基]-4-羟基苯甲醛 | 116546-04-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-[(二甲氨基)甲基]-4-羟基苯甲醛
• 中文别名: 3-[(二甲基氨基)甲基]-4-羟基苯甲醛
• 英文名称: 3-((dimethylamino)methyl)-4-hydroxybenzaldehyde
• 英文别名: 4-hydroxy-3-[(dimethylamino)methyl]-benzaldehyde；2-[(Dimethylazaniumyl)methyl]-4-formylphenolate
• CAS: 116546-04-4
• 化学式: C₁₀H₁₃NO₂
• mdl: MFCD07186317
• 分子量: 179.219
• InChiKey: RONWGSMHSGHRJS-UHFFFAOYSA-N

物化性质

• 沸点：
  280.6±30.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2922509090

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 3-[(Dimethylamino)Methyl]-4-Hydroxybenzaldehyde
: CBR00370
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.

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SECTION 2: Hazards identification
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.

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SECTION 3: Composition/information on ingredients
Substances
Molecular weight : 179,22 g/mol
No components need to be disclosed according to the applicable regulations.

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SECTION 4: First aid measures
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
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.
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
Nature of decomposition products not known.
Advice for firefighters
Wear self-contained breathing apparatus for firefighting if necessary.
Further information
No data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapours, mist or gas.
For personal protection see section 8.
Environmental precautions
No special environmental precautions required.
Methods and materials for containment and cleaning up
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
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.
Storage class (TRGS 510): Non Combustible Solids
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
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
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
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
No special environmental precautions required.

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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 No data available
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.
Possibility of hazardous reactions
No data available
Conditions to avoid
No data available
Incompatible materials
No data available
Hazardous decomposition products
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
No data available
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
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.
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.
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：

  3-[(二甲氨基)甲基]-4-羟基苯甲醛 在 咪唑 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 4-Hydroxymethyl-2-piperidin-1-ylmethyl-phenol
  参考文献：
  名称：

  Synthesis, spectroscopic characterization and chemical reactions of stable o-QM on solid phase

  摘要：

  通过在固相（RTHP）上锚定反应性邻-QM 中间体，实现了醌甲醚稳定化的新方法。研究人员探讨了受支持的邻-QM 对以 N 和 S 为中心的亲核物的反应性和选择性。

  DOI：

  10.1039/b205793j
• 作为产物：
  描述：

  4-cyano-3-<(dimethylamino)methyl>phenol 在 镍 甲酸 作用下， 反应 3.0h， 以60%的产率得到3-[(二甲氨基)甲基]-4-羟基苯甲醛
  参考文献：
  名称：

  酰基辅酶A：胆固醇O-酰基转移酶（ACAT）的抑制剂，作为降血脂药。8.将酰胺或胺官能团引入一系列双取代的脲和氨基甲酸酯中。体外对ACAT抑制作用和体内功效的影响。

  摘要：

  制备了一系列含有酰胺基或胺基的双取代脲，并评估了它们在体外抑制酰基-CoA：胆固醇O-酰基转移酶的能力以及在体内各种由胆固醇喂养的大鼠模型中降低血浆总胆固醇的能力。这类化合物中极性或可电离官能团的存在可以赋予这些化合物更大的水溶性，从而改善向肠道小肠细胞内酶位置的转运。即使是在水性媒介物中给药，这类化合物在慢性胆固醇喂养的高胆固醇血症大鼠模型中也能降低胆固醇。通常，在高胆固醇血症的急性大鼠模型中，含胺化合物比酰胺更有效和有效。进一步的结构活性关系研究表明，酰胺/胺基团的优选位置是尿素部分的β，而不是α，并且在该系列中，要获得良好的体外效果，必须存在仲胺（或酰胺）质子效力。这些化合物之一9n（-）在水性介质中给药给预先建立的高胆固醇血症的大鼠时，可降低血浆总胆固醇（-47％）和提高高密度脂蛋白胆固醇（+ 256％）。

  DOI：

  10.1021/jm00038a010

文献信息

• Discovery of potent and orally bioavailable 17β-hydroxysteroid dehydrogenase type 3 inhibitors
  作者：Koichiro Harada、Hideki Kubo、Jun Abe、Mari Haneta、Arnel Conception、Shinichi Inoue、Satoshi Okada、Kazuhiko Nishioka

  DOI：10.1016/j.bmc.2012.03.052

  日期：2012.5

  and consequently a number of compounds from this series demonstrated single-digit nanomolar 17β-HDS3 inhibitory activity in vitro. Subsequent optimization work in pursuit of the improvement of oral bioavailability demonstrated in vivo proof-of-concept by prodrug strategy based on phosphate esters for these 17β-HSD3 inhibitors. When a phosphate ester 16 was administered orally at a high dose of 100 mg/kg

  先前我们已经报道了衍生自亚苄基恶唑烷二酮和噻唑烷二酮支架的新型3类有效的17β-羟类固醇脱氢酶抑制剂（17β-HSD3）的发现。在这项研究中，这些类似物是在基于人类细胞的分析中进行设计，合成和评估的。建立了围绕该药效团的详细的结构-活性关系（SAR），因此，该系列化合物中的许多化合物在体外均表现出一位数的纳摩尔17β-HDS3抑制活性。为改善口服生物利用度而进行的后续优化工作已通过基于磷酸酯的前药策略针对这些17β-HSD3抑制剂进行了体内概念验证。当以100 mg / kg的高剂量口服磷酸酯16时，图16显示，在促黄体生成激素释放激素（LH-RH）诱导的T产生测定中，相对于阳性对照，有效的睾丸激素（T）降低作用大约两倍。给药后4小时，降低T的作用持续在对照的约10％水平。基于该系列的非甾体分子具有为治疗前列腺癌提供独特而有效的临床机会的潜力。
• [EN] NOVEL ACRYLAMIDE DERIVATIVES AS ANTIMALARIAL AGENTS<br/>[FR] NOUVEAUX DÉRIVÉS D'ACRYLAMIDE COMME AGENTS ANTIPALUDIQUES
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2014141175A1

  公开（公告）日：2014-09-18

  The invention relates to novel acrylamide derivatives of the formula (I) wherein R1, R 2, R 3, X, and ring A are as defined in the description, and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including pharmaceutical compositions containing those compounds and their use as medicaments for the treatment or prevention of protozoal infections, such as especially malaria.

  该发明涉及公式（I）中的新型丙烯酰胺衍生物，其中R1、R2、R3、X和环A如描述中所定义，并且它们作为活性成分用于制备药物组合物。该发明还涉及相关方面，包括含有这些化合物的药物组合物以及它们作为药物治疗或预防原虫感染，尤其是疟疾的用途。
• COMPOUNDS OF PHOSPHINANES AND AZAPHOSPHINANES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：LES LABORATOIRES SERVIER

  公开号：US20180016288A1

  公开（公告）日：2018-01-18

  Compounds of formula (I) wherein: Ak 1 represents an alkyl chain, X represents —(CH 2 ) m —, —CH(R)—, —N(R)—, —CH 2 —N(R)—, —N(R)—CH 2 — or —CH 2 —N(R)—CH 2 —, m and R are as defined in the description, R 1 and R 2 each represent H when X represents —(CH 2 ) m —, —CH(R)—, —N(R)—, —CH 2 —N(R)— or —N(R)—CH 2 —, or together form a bond when X represents —CH 2 —N(R)—CH 2 —, R 3 represents NH 2 , Cy-NH 2 , Cy-Ak 3 -NH 2 or piperidin-4-yl, Cy and Ak 3 are as defined in the description, R 4 and R 5 , which may be identical or different, each represent H or F, their optical isomers, and addition salts thereof with a pharmaceutically acceptable acid. Medicinal products containing the same which are useful in treating conditions requiring a TAFIa inhibitor.

  式(I)的化合物中： Ak1代表一个烷基链， X代表—(CH2)m—，—CH(R)—，—N(R)—，—CH2—N(R)—，—N(R)—CH2—或—CH2—N(R)—CH2—， m和R如描述中所定义， R1和R2分别在X代表—(CH2)m—，—CH(R)—，—N(R)—，—CH2—N(R)—或—N(R)—CH2—时代表H， 或者当X代表—CH2—N(R)—CH2—时，它们一起形成一个键， R3代表NH2，Cy-NH2，Cy-Ak3-NH2或哌啶-4-基， Cy和Ak3如描述中所定义， R4和R5，可能相同也可能不同，每个代表H或F， 它们的光学异构体， 以及它们与药学上可接受的酸形成的盐。 包含这些化合物的药品，在治疗需要TAFIa抑制剂的情况下有用。
• 查尔酮曼尼希碱类化合物、其制备方法和用途
  申请人：四川大学

  公开号：CN109678736B

  公开（公告）日：2022-04-22

  本发明公开了一类新型的查尔酮曼尼希碱类化合物（I）及其药学上可接受的盐、其制备方法、药物组合物和在制备治疗和/或预防神经系统相关疾病药物中的用途，包括但不限于血管性痴呆、阿尔茨海默氏病、帕金森氏病、亨廷顿氏病、HIV相关痴呆病、多发性硬化症、肌萎缩侧索硬化症、神经性疼痛、青光眼、缺血性脑卒中、出血性脑卒中、以及脑外伤引起的神经损伤等疾病；。
• A molecular approach to rationally constructing specific fluorogenic substrates for the detection of acetylcholinesterase activity in live cells, mice brains and tissues
  作者：Xiaofeng Wu、Jong Min An、Jizhen Shang、Eugene Huh、Sujie Qi、Eunhye Lee、Haidong Li、Gyoungmi Kim、Huimin Ma、Myung Sook Oh、Dokyoung Kim、Juyoung Yoon

  DOI：10.1039/d0sc04213g

  日期：——

  hydrolase tightly associated with neurological diseases. Currently, developing specific substrates for imaging AChE activity still remains a great challenge due to the interference from butyrylcholinesterase (BChE) and carboxylesterase (CE). Herein, we propose an approach to designing specific substrates for AChE detection by combining dimethylcarbamate choline with a self-immolative scaffold. The representative

  乙酰胆碱酯酶（AChE）是与神经系统疾病紧密相关的极其关键的水解酶。目前，由于丁酰胆碱酯酶（BChE）和羧酸酯酶（CE）的干扰，开发用于成像AChE活性的特定底物仍然是一个巨大的挑战。在本文中，我们提出了一种通过结合氨基甲酸二甲酯胆碱和自消灭支架来设计用于AChE检测的特定底物的方法。代表性的P10可以有效消除CE和BChE的干扰。通过对细胞中的AChE活性进行成像已证明了P10的高特异性。而且，P10也可用于成功绘制正常小鼠大脑不同区域的AChE活性图，这可能为临床研究中的AChE评估提供重要数据。这种合理有效的方法也可以为设计具有不同特性的探针以研究生物系统中的AChE和为其他酶设计特异性底物的另一种方法提供坚实的基础。