4-氨基苯甲酸甲酯盐酸盐 | 63450-84-0

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: 4-氨基苯甲酸甲酯盐酸盐
• 中文别名: 5-甲基-4,6-二羟基嘧啶
• 英文名称: methyl 4-aminobenzoate hydrochloride
• 英文别名: methyl p-aminobenzoate hydrochloride；methyl 4-aminobenzoate hydrochloric acid；4-aminobenzoic acid methyl ester hydrochloride；methyl para-aminobenzoate hydrochloride；(4-Methoxycarbonylphenyl)azanium;chloride；(4-methoxycarbonylphenyl)azanium;chloride
• CAS: 63450-84-0
• 化学式: C₈H₉NO₂*ClH
• 分子量: 187.626
• InChiKey: UMLFQRYMOHDCCK-UHFFFAOYSA-N

物化性质

• 熔点：
  208 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.48
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 安全说明：
  S24/25

SDS

Name:	Methyl 4-aminobenzoate hydrochloride 97% Material Safety Data Sheet
Synonym:
CAS:	63450-84-0

Section 1 - Chemical Product MSDS Name:Methyl 4-aminobenzoate hydrochloride 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
63450-84-0	Methyl 4-aminobenzoate hydrochloride	97%	264-184-6

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 63450-84-0: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 208 - 210 deg C(decom)
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H10ClNO2
Molecular Weight: 188

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents, reducing agents, acids, bases.
Hazardous Decomposition Products:
Hydrogen chloride, chlorine, nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 63450-84-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl 4-aminobenzoate hydrochloride - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 63450-84-0: No information available.
Canada
CAS# 63450-84-0 is listed on Canada's NDSL List.
CAS# 63450-84-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 63450-84-0 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-氨基苯甲酸甲酯盐酸盐 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 60.0~65.0 ℃ 、784.54 kPa 条件下， 以71.7%的产率得到4-氨基环己甲酸甲酯盐酸盐
  参考文献：
  名称：

  Short and Efficient Process for the Synthesis of trans-4-Aminocyclohexanecarboxylic Acid Derivatives

  摘要：

  This contribution relates to an industrially feasible process for the preparation of isomerically pure trans-4-amino-1-cyclohexanecarboxylic acid derivatives that are useful building blocks in the synthesis of several pharmacologically active compounds such as glimepiride, L-370518.

  DOI：

  10.1021/op900195w
• 作为产物：
  描述：

  4-乙酰氨基苯甲酸甲酯 在 氯化亚砜 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以98.8%的产率得到4-氨基苯甲酸甲酯盐酸盐
  参考文献：
  名称：

  A facile and efficient method for the selective deacylation of N-arylacetamides and 2-chloro-N-arylacetamides catalyzed by SOCl2

  摘要：

  亚硫酰氯在无水条件下高效且选择性地促进了N-芳基乙酰胺和2-氯-N-芳基乙酰胺的去酰化反应，且不影响酯基、氨基磺酰基或苄氧酰胺基。这种方法已成功应用于多种底物，包括不同的N-芳基乙酰胺和2-氯-N-芳基乙酰胺，具有试剂成本低、选择性好、产率高、反应时间短和操作简便等吸引人的优点。这种新方法可能被用于选择性地在芳香族酰胺和烷基酰胺之间进行去酰化反应。

  DOI：

  10.1007/s11164-011-0327-6

文献信息

• Discovery of N-(2-Aminophenyl)-4-(bis(2-chloroethyl)amino)Benzamide as a Potent Histone Deacetylase Inhibitor
  作者：Lihui Zhang、Xiaoyang Li、Yiming Chen、Minghui Wan、Qixiao Jiang、Li Zhang、C. James Chou、Weiguo Song、Lei Zhang

  DOI：10.3389/fphar.2019.00957

  日期：——

  Inhibition of histone deacetylases (HDACs) has been an important emerging therapy for the treatment of multiple cancers. However, the application of HDAC inhibitors is restricted by the limited potency against solid tumors. In order to discover novel HDAC inhibitors with potent antitumor activities, nitrogen mustard group was introduced to the structure of CI994. The derived molecule N-(2-aminophe

  组蛋白脱乙酰酶（HDAC）的抑制已成为治疗多种癌症的重要新兴疗法。然而，HDAC抑制剂的应用因对抗实体瘤的效力有限而受到限制。为了发现具有有效抗肿瘤活性的新型HDAC抑制剂，在CI994的结构中引入了氮芥基团。衍生分子 N-(2-氨基苯基)-4-(双(2-氯乙基)氨基)苯甲酰胺 (NA) 对 HDAC1、HDAC2、和HDAC3，分别。在抗增殖测定中，NA 对 A2780 和 HepG2 细胞生长的抑制作用分别比辛二酰苯胺异羟肟酸 (SAHA)（27.3 和 19.5 μM）高 10.3 倍（2.66 μM）和 11.3 倍（1.73 μM）。进一步基于 HepG2 细胞的细胞周期和细胞凋亡研究表明，诱导 G2/M 期停滞和细胞凋亡有助于 NA 的抗肿瘤作用。建议NA可以作为先导化合物来开发用于治疗实体瘤的双功能HDAC抑制剂。
• Discovery of N-(2-Amino-4-Fluorophenyl)-4-[bis-(2-Chloroethyl)-Amino]-Benzamide as a Potent HDAC3 Inhibitor
  作者：Yiming Chen、Jinhong Feng、Yajie Hu、Xuejian Wang、Weiguo Song、Lei Zhang

  DOI：10.3389/fonc.2020.592385

  日期：——

  In discovery of HDAC inhibitors with improved activity and selectivity, fluorine substitution was performed on our previously derived lead compound. The synthesized molecules N-(2-amino-4-fluorophenyl)-4-[bis-(2-chloroethyl)-amino]-benzamide (FNA) exhibited class I (HDAC1, 2, and 3) selectivity in the in vitro enzymatic assay and especially potent against HDAC3 activity (IC50: 95.48 nM). The results

  在发现具有改进的活性和选择性的HDAC抑制剂后，对我们先前衍生的铅化合物进行了氟取代。合成分子N-（2-氨基-4-氟苯基）-4- [bis-（2-氯乙基）-氨基]-苯甲酰胺（FNA）在I类（HDAC1、2和3）中具有选择性 体外酶促测定，尤其对HDAC3活性有效（IC 50：95.48 nM）。结果体外抗增殖试验表明，与SAHA（17.25μM）相比，FNA对HepG2细胞表现出实体瘤细胞抑制活性，IC 50值为1.30μM。而且，体内异种移植模型研究表明，与SAHA（TGI为48.13％）相比，FNA可以抑制肿瘤生长，其中TGI为48.89％。进一步的基于HepG2细胞的凋亡和细胞周期研究表明，促进凋亡和G2 / M期阻滞有助于FNA的抗肿瘤活性。此外，药物联合结果显示0.5μMFNA可以提高紫杉醇和喜树碱的抗癌活性。本研究揭示了FNA作为高效先导化合物用于进一步发现同工型选择性HDAC抑制剂的潜力。
• Discovery of indole-3-butyric acid derivatives as potent histone deacetylase inhibitors
  作者：Yiming Chen、Lihui Zhang、Lin Zhang、Qixiao Jiang、Lei Zhang

  DOI：10.1080/14756366.2020.1870457

  日期：2021.1.1

  Abstract In discovery of HDAC inhibitors (HDACIs) with improved anticancer potency, structural modification was performed on the previous derived indole-3-butyric acid derivative. Among all the synthesised compounds, molecule I13 exhibited high HDAC inhibitory and antiproliferative potencies in the in vitro investigations. The IC50 values of I13 against HDAC1, HDAC3, and HDAC6 were 13.9, 12.1, and

  摘要 在发现具有改善的抗癌效力的 HDAC 抑制剂 (HDACIs) 时，对先前衍生的吲哚-3-丁酸衍生物进行了结构修饰。在所有合成的化合物中，分子I13在体外研究中表现出高 HDAC 抑制和抗增殖能力。I13对 HDAC1、HDAC3 和 HDAC6的 IC 50值分别为 13.9、12.1 和 7.71 nM。在基于癌细胞的筛选中，与 SAHA 相比，分子I13在抑制 U937、U266、HepG2、A2780 和 PNAC-1 细胞方面显示出增加的抗增殖活性。在 HepG2 异种移植模型中，50 mg/kg/d 的I13与 100 mg/kg/d 的 SAHA 相比，可以抑制无胸腺小鼠的肿瘤生长。发现诱导细胞凋亡在分子I13的抗癌效力中起重要作用。总的来说，发现了一种具有高抗癌活性的 HDACI ( I13 )，可用作进一步 HDACI 设计的先导化合物。
• Compounds containing a michael-acceptor, especially maleimide or maleic
  申请人：Vanguard Medica Limited

  公开号：US05877204A1

  公开（公告）日：1999-03-02

  The present invention relates to compounds which are useful as sunscreens. The compounds persist on the skin for much longer than conventional sunscreens because they comprise a Michael acceptor linked directly or indirectly to a chromophore. The Michael acceptor is capable of undergoing a conjugate addition reaction with thiol groups present in cysteine residues of keratin and thus the compound is chemically bound to the skin and will not be removed by immersion in water.

  本发明涉及作为防晒剂有用的化合物。这些化合物在皮肤上持续时间比传统防晒剂长得多，因为它们包含一个与色团直接或间接连接的迈克尔受体。迈克尔受体能够与角蛋白半胱氨酸残基中存在的巯基发生共轭加成反应，因此该化合物与皮肤化学结合，不会被水浸泡而去除。
• Cobalt‐Catalyzed Deoxygenative Hydroboration of Nitro Compounds and Applications to One‐Pot Synthesis of Aldimines and Amides
  作者：Kristina A. Gudun、Raikhan Zakarina、Medet Segizbayev、Davit Hayrapetyan、Ainur Slamova、Andrey Y. Khalimon

  DOI：10.1002/adsc.202101043

  日期：2022.2

  The commercially available and bench-stable Co(acac)2 ligated with bis[(2-diphenylphosphino)phenyl] ether (dpephos) was employed for selective room temperature hydroboration of nitro compounds with HBPin (TOF up to 4615 h−1), tolerating halide, hydroxy, amino, ether, ester, lactone, amide and heteroaromatic functionalities. These reactions offered a direct access to a variety of N-borylamines RN(H)BPin

  使用与双[(2-二苯基膦基)苯基]醚 (dpephos) 连接的可商购且台式稳定的 Co(acac) 2与 HBPin 选择性室温硼氢化硝基化合物（TOF 高达 4615 h -1），耐受卤化物、羟基、氨基、醚、酯、内酯、酰胺和杂芳族官能团。这些反应提供了直接获得各种原位N-硼胺 RN(H)BPin的途径用醛和羧酸处理产生一系列醛亚胺和仲羧酰胺，而不需要脱水和/或偶联剂。以顺序一锅法将这些转化结合起来，可以从容易获得且廉价的硝基化合物直接和选择性地合成醛亚胺和仲羧酰胺。