3-甲醛苯甲酸甲酯 | 52178-50-4

• 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: 3-甲醛苯甲酸甲酯
• 中文别名: 3-醛基苯甲酸甲酯；甲基m-甲酰苯甲酸甲酯；3-甲酰苯甲酸甲酯
• 英文名称: Methyl 3-formylbenzoate
• CAS: 52178-50-4
• 化学式: C₉H₈O₃
• mdl: MFCD00189379
• 分子量: 164.161
• InChiKey: UVSBCUAQEZINCQ-UHFFFAOYSA-N

物化性质

• 熔点：
  48-52 °C
• 沸点：
  272.8±23.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  如果按照规格正确使用和储存，则不会分解，没有已知的危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R22
• WGK Germany：
  3
• 海关编码：
  2918300090
• 危险品运输编号：
  NONH for all modes of transport
• 储存条件：
  请将贮藏器密封保存，并存放在阴凉、干燥处。同时，确保工作环境有良好的通风或排气设施。

SDS

Name:	Methyl 3-formylbenzoate Material Safety Data Sheet
Synonym:	Methyl benzaldehyde-4-carboxylat
CAS:	52178-50-4

Section 1 - Chemical Product MSDS Name:Methyl 3-formylbenzoate Material Safety Data Sheet
Synonym:Methyl benzaldehyde-4-carboxylat

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
52178-50-4	Methyl 3-formylbenzoate		unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
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# 52178-50-4: 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: Crystalline powder
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 49 - 51 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: practically insoluble
Specific Gravity/Density:
Molecular Formula: C9H8O3
Molecular Weight: 164.2

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 52178-50-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl 3-formylbenzoate - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 52178-50-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 52178-50-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 52178-50-4 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质：类白色结晶

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  间苯二甲酸二甲酯	dimethyl Isophthalate	1459-93-4	C10H10O4	194.187
  间苯二甲酸单甲酯	benzene 1,3-dicarboxylic acid monomethyl ester	1877-71-0	C9H8O4	180.16
  3-甲基苯甲酸甲酯	1-methoxycarbonyl-3-methylbenzene	99-36-5	C9H10O2	150.177
  3-羟甲基苯甲酸甲酯	methyl 3-(hydroxymethyl)benzoate	67853-03-6	C9H10O3	166.177
  3-羧基苯甲醛	3-Carboxybenzaldehyde	619-21-6	C8H6O3	150.134
  3-氰基苯甲酸甲酯	methyl 3-cyanobenzoate	13531-48-1	C9H7NO2	161.16
  3-(溴甲基)苯甲酸甲酯	3-methoxycarbonylbenzyl bromide	1129-28-8	C9H9BrO2	229.073
  3-(氨甲基)苯甲酸甲酯	3-methoxycarbonyl benzylamine	93071-65-9	C9H11NO2	165.192
  ——	methyl 3-(dibromomethyl)benzoate	——	C9H8Br2O2	307.969
  ——	3-carbomethoxybenzaldiacetate	70760-00-8	C13H14O6	266.251
• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  间苯二甲酸单甲酯	benzene 1,3-dicarboxylic acid monomethyl ester	1877-71-0	C9H8O4	180.16
  3-羟甲基苯甲酸甲酯	methyl 3-(hydroxymethyl)benzoate	67853-03-6	C9H10O3	166.177
  3-羧基苯甲醛	3-Carboxybenzaldehyde	619-21-6	C8H6O3	150.134
  3-甲酰基苯甲酸叔丁酯	tert-butyl 3-formylbenzoate	247186-56-7	C12H14O3	206.241
  3-氰基苯甲酸甲酯	methyl 3-cyanobenzoate	13531-48-1	C9H7NO2	161.16
  3-(氟甲基)苯甲酸甲酯	methyl 3-(fluoromethyl)benzoate	89540-39-6	C9H9FO2	168.168
  3-乙烯苯甲酸甲酯	methyl 3-ethenylbenzoate	38383-50-5	C10H10O2	162.188
  ——	methyl 3-(iodomethyl)benzoate	854645-25-3	C9H9IO2	276.074
  3-(溴甲基)苯甲酸甲酯	3-methoxycarbonylbenzyl bromide	1129-28-8	C9H9BrO2	229.073
  3-(氨甲基)苯甲酸甲酯	3-methoxycarbonyl benzylamine	93071-65-9	C9H11NO2	165.192

反应信息

• 作为反应物：
  描述：

  3-甲醛苯甲酸甲酯 在 水 、 1-丙基磷酸酐 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 2-甲基四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 反应 1.0h， 生成 3-[[[((1R)-1-(4-氟苯基)乙基](3-喹啉基羰基)氨基]甲基]苯甲酸
  参考文献：
  名称：

  [EN] ARYL SUBSTITUTED CARBOXAMIDE DERIVATIVES AS TRPM8 MODULATORS
  [FR] DÉRIVÉS DE CARBOXAMIDE SUBSTITUÉS PAR ARYLE EN TANT QUE MODULATEURS DE TRPM8

  摘要：

  本发明提供了一种化合物，其化学式为（I）：其中A、R1、R2和R3如本文所定义，或其药学上可接受的盐。这些化合物是小分子TRPM8阻断剂，因此在预防或治疗包括寒冷痛觉异常和雷诺综合征在内的各种疾病、症状或综合征中有用。

  公开号：

  WO2012120398A1
• 作为产物：
  描述：

  3-甲基苯甲酸甲酯 在 dipotassium peroxodisulfate 、 cobalt(II) diacetate tetrahydrate 、 三氟乙酸 、 三氟乙酸酐 作用下， 以64%的产率得到3-甲醛苯甲酸甲酯
  参考文献：
  名称：

  在 TFA/TFAA 中用过硫酸钾进行钴 (ii) 催化的苄基氧化†

  摘要：

  本文报道了钴催化的 C(sp 3 )-H 氧化反应以提供醛。这种转化表现出高化学选择性，并耐受各种带有吸电子取代基的甲基芳烃。该反应提供了从甲基芳烃中快速获得各种醛的途径。值得注意的是，TFA/TFAA 首次作为混合溶剂用于钴催化的苄基亚甲基氧化反应。

  DOI：

  10.1039/c9ra03346g

文献信息

• [EN] CINNOLINE DERIVATIVES USEFUL AS CB-1 RECEPTOR INVERSE AGONISTS<br/>[FR] DÉRIVÉS DE CINNOLINE UTILES EN TANT QU'AGONISTES INVERSES DE RÉCEPTEURS CB-1
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2016115013A1

  公开（公告）日：2016-07-21

  The present invention is directed to cinnoline derivatives of formula (I) pharmaceutical compositions containing them and their use in the treatment of disorders and conditions mediated by the CB-1 receptor; more particularly, use in the treatment of disorders and conditions responsive to inverse agonism of the CB-1 receptor. More particularly, the compounds of the present invention are useful in the treatment of metabolic disorders.

  本发明涉及公式（I）的喹啉衍生物，含有它们的药物组合物以及它们在治疗由CB-1受体介导的疾病和症状中的应用；更具体地，在治疗对CB-1受体的反向激动作用响应的疾病和症状中的应用。更具体地说，本发明的化合物在治疗代谢性疾病中是有用的。
• Aromatic amine derivative and use thereof
  申请人：Taniguchi Takahiko

  公开号：US20090325956A1

  公开（公告）日：2009-12-31

  The present invention provides a novel SCD inhibitor. An SCD inhibitor containing a compound represented by the formula [I] wherein ring A is an optionally substituted aromatic ring, ring B is an optionally substituted ring, ring C is an optionally substituted aromatic ring, R is a hydrogen atom, an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, and X is a spacer having 1 to 5 atoms in the main chain, or a salt thereof, or a prodrug thereof.

  本发明提供了一种新型SCD抑制剂。一种包含由下式[I]表示的化合物的SCD抑制剂 其中环A是可选择取代的芳香环，环B是可选择取代的环，环C是可选择取代的芳香环，R是氢原子，可选择取代的碳氢基团或可选择取代的杂环基团，X是具有主链中1到5个原子的间隔物，或其盐，或其前药。
• [EN] NOVEL 3,3-DIMETHYL TETRAHYDROQUINOLINE DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS DE 3,3-DIMÉTHYLTÉTRAHYDROQUINOLÉINE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2011128251A1

  公开（公告）日：2011-10-20

  A compound of formula (I) as well as pharmaceutically acceptable salt thereof, wherein R1 to R5 have the significance given in claim 1, can be used as a medicament.

  化合物的化学式（I）及其药用盐，其中R1至R5具有权利要求1中给定的含义，可用作药物。
• NOVEL 3,3-DIMETHYL TETRAHYDROQUINOLINE DERIVATIVES
  申请人：Chen Li

  公开号：US20110257151A1

  公开（公告）日：2011-10-20

  A compound of formula (I) as well as pharmaceutically acceptable salt thereof, wherein R 1 to R 5 have the significance given in claim 1 , can be used as a medicament.

  式（I）的化合物以及其药学上可接受的盐，其中R1至R5具有权利要求1中给定的含义，可用作药物。
• Discovery and preliminary structure–activity relationship of 1H-indazoles with promising indoleamine-2,3-dioxygenase 1 (IDO1) inhibition properties
  作者：Shan Qian、Tao He、Wei Wang、Yanying He、Man Zhang、Lingling Yang、Guobo Li、Zhouyu Wang

  DOI：10.1016/j.bmc.2016.10.003

  日期：2016.12

  necessary for IDO1 inhibition, and the substituent groups at the both 4-position and 6-position largely affect inhibitory activity. The docking model exhibited that the effective interactions of 1H-indazoles with ferrous ion of heme and key residues of hydrophobic Pocket A and B ensured the IDO1 inhibitory activities. The study suggested that the 1H-indazole was a novel interesting scaffold for IDO

  吲哚胺2,3-双加氧酶1（IDO1）介导的色氨酸降解的犬尿氨酸途径被确定为逃避潜在有效免疫应答的肿瘤细胞中重要的免疫效应子途径。IDO1是抗癌治疗的一个有吸引力的靶标，并且IDO1抑制剂的发现在学术研究实验室和制药组织中都在紧锣密鼓地进行中。我们的研究发现1H-吲唑是一种具有重要IDO1抑制活性的新型关键药效团。合成了一系列新的1H-吲唑衍生物并确定了酶抑制活性，化合物2g表现出最高的活性，IC50值为5.3μM。1H-吲唑衍生物作为新型IDO1抑制剂的结构活性关系（SARs）分析表明1H-吲唑支架对于IDO1抑制是必需的，并且4位和6位的取代基都对抑制活性有很大影响。 。对接模型显示1H-吲唑与血红素亚铁离子以及疏水性口袋A和B的关键残基的有效相互作用确保了IDO1抑制活性。研究表明1H-吲唑是抑制IDO进一步发展的一种新颖有趣的支架。对接模型显示1H-吲唑与血红素亚铁离子以及疏水性口袋

表征谱图