3-羟基异喹啉 | 7651-81-2

• 物质功能分类: 医药中间体 - 杂环化合物 - 喹啉类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 中文名称: 3-羟基异喹啉
• 中文别名: 3-异喹啉醇
• 英文名称: 3-isoquinolinol
• 英文别名: 3-Hydroxyisoquinoline；isoquinolin-3-ol；3-Hydroxyisochinolin；2H-isoquinolin-3-one
• CAS: 7651-81-2
• 化学式: C₉H₇NO
• mdl: MFCD00075524
• 分子量: 145.161
• InChiKey: GYPOFOQUZZUVQL-UHFFFAOYSA-N

物化性质

• 熔点：
  192-194 °C (lit.)
• 沸点：
  551.9±23.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解。避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S37/39
• 危险类别码：
  R22,R41
• WGK Germany：
  3
• 海关编码：
  2933499090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  请确保贮藏器密封，并将其放入一个紧密封装的容器中。储存时应选择阴凉、干燥的地方。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 3-Hydroxyisoquinoline
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. : 7651-81-2
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
Acute toxicity, Oral (Category 4), H302
Serious eye damage (Category 1), H318
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
Xn Harmful R22, R41
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 Danger
Hazard statement(s)
H302 Harmful if swallowed.
H318 Causes serious eye damage.
Precautionary statement(s)
P280 Wear protective gloves/ eye protection/ face protection.
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
Synonyms : 3-Isoquinolinol
Formula : C9H7NO
Molecular Weight : 145,16 g/mol
CAS-No. : 7651-81-2
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
3-Hydroxyisoquinoline
Acute Tox. 4; Eye Dam. 1; -
H302, H318
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.Normal measures for preventive fire
protection.
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.
Specific end use(s)
A part 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
Face shield and safety glasses 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
Where risk assessment shows air-purifying respirators are appropriate use a full-face particle
respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering
controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. 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: crystalline
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: 192 - 194 °C - lit.
point
f) Initial boiling point and 267 °C at 1.013 hPa
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 insoluble
o) Partition coefficient: n- log Pow: 1,887
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
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
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. 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
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

制备过程如下：

1. 用橡胶隔片密封含有磁性随动件的可重新密封反应管。
2. 在氩气流下用火焰干燥反应管。
3. 向反应管中依次加入tBu3P·HBF4（10.9毫克，0.0377毫摩尔）和Pd2（dba）3（17.3毫克，0.0189毫摩尔）。
4. 将芳基溴（83.6毫克）溶解在无水甲苯（0.9毫升）中，并通过注射器将其加入反应管内。
5. 向反应管中添加乙酸叔丁酯（87.6毫克）。
6. 将反应混合物冷却至-78°C，用氩气脱气15分钟。
7. 通过注射器向混合物中加入脱气的LiHDMS溶液（0.942毫升，1M甲苯溶液），再次脱气15分钟。
8. 更换橡胶隔膜，并在室温下搅拌反应16小时。
9. 通过加入饱和的NaHCO3水溶液（25 mL）淬灭反应。
10. 使用Et2O（3×25 mL）萃取水层，用Na2SO4干燥合并的有机物，过滤并去除溶剂。最后，通过快速柱色谱法纯化产物[石油/EtOAc 50:1，分级至5:1]。

用途：

3-羟基异喹啉是聚乙烯醇（PVA）与尼罗红聚合物混合物中使用的化合物，可通过福斯特共振能量转移产生白光。它可用作有机和医药中间体。

反应信息

• 作为反应物：
  描述：

  3-羟基异喹啉 在 环己烷 、 五氟化锑 作用下， 以 三氟甲磺酸 为溶剂， 反应 1.0h， 以94%的产率得到5,6,7,8-四氢-3(2H)-异喹啉酮
  参考文献：
  名称：

  1-和3-异喹啉醇的超酸性活化及其亲电反应。

  摘要：

  当在CF（3）SO（3）H-SbF（5）酸体系中活化时，异美1和3异喹啉醇（11和12）经历与环己烷的选择性离子氢化反应，得到5,6,7,8-tetrahydro-1 （2H）-和5,6,7,8-四氢-3（2H）-异喹啉酮（22和27）。在氯化铝的影响下，还分别获得了3,4-二氢-1（2H）-和1,4-二氢-3（2H）-异喹啉酮（23和28）类似的产物。在温和的条件下，化合物11和12在卤化铝存在下也与苯缩合，得到3,4-二氢-3-苯基-1（2H）-和1,4-二氢-1-苯基-3（2H） ）-异喹啉酮（分别为24和29）。在强酸性HBr-AlBr（3）下延长反应时间或催化提供了另一种反应途径，可产生5,6-dihydro-6,8-diphenyl-1（2H）-和5,6,7,8-tetrahydro-6 ，8-二苯基-3（2H）-异喹啉酮（25和30），分别。还发现在邻二氯苯中存在卤化铝的情况

  DOI：

  10.1021/jo0204855
• 作为产物：
  描述：

  3-溴异喹啉 在 copper(ll) sulfate pentahydrate 、 铜 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 12.0h， 生成 3-羟基异喹啉
  参考文献：
  名称：

  Xingjun, Jiang; Jianbo, He; Hongli, Chen, Indian Journal of Heterocyclic Chemistry, 2017, vol. 27, # 1, p. 65 - 70

  摘要：

  DOI：

文献信息

• Compounds and uses thereof for decreasing activity of hormone-sensitive lipase
  申请人：——

  公开号：US20030166644A1

  公开（公告）日：2003-09-04

  Use of compounds to inhibit hormone-sensitive lipase, pharmaceutical compositions comprising the compounds, methods of treatment employing these compounds and compositions, and novel compounds. The present compounds are inhibitors of hormone-sensitive lipase and may be useful in the treatment and/or prevention of medical disorders where a decreased activity of hormone-sensitive lipase is desirable.

  使用化合物抑制激素敏感性脂肪酶，包括这些化合物的药物组合物，使用这些化合物和组合物的治疗方法，以及新化合物。目前的化合物是激素敏感性脂肪酶的抑制剂，可能在治疗和/或预防需要降低激素敏感性脂肪酶活性的医学疾病中有用。
• Fused azabicyclic compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor
  申请人：——

  公开号：US20040157849A1

  公开（公告）日：2004-08-12

  Compounds of formula (I) 1 are novel VR1 antagonists that are useful in treating pain, inflammatory thermal hyperalgesia, urinary incontinence and bladder overactivity.

  式（I）的化合物是新颖的VR1拮抗剂，可用于治疗疼痛、炎症性热性过敏、尿失禁和膀胱过度活动。
• [EN] SUBSTITUTED 2-AZABICYCLO[3.1.1]HEPTANE AND 2-AZABICYCLO[3.2.1]OCTANE DERIVATIVES AS OREXIN RECEPTOR ANTAGONISTS<br/>[FR] DÉRIVÉS DE 2-AZABICYCLO[3.1.1]HEPTANE ET DE 2-AZABICYCLO[3.2.1]OCTANE SUBSTITUÉS EN TANT QU'ANTAGONISTES DU RÉCEPTEUR DE L'OREXINE
  申请人：CHRONOS THERAPEUTICS LTD

  公开号：WO2019043407A1

  公开（公告）日：2019-03-07

  There is provided a compound of formula (I), wherein L1 to L3, R1 to R4, X, A and B have meanings given in the description, and pharmaceutically acceptable salts, solvates and prodrugs thereof, which compounds are useful as antagonists of the orexin-1 and orexin-2 receptors or as selective antagonists of the orexin-1 receptor, and thus, in particular, in the treatment or prevention of inter alia substance dependence, addiction, anxiety disorders, panic disorders, binge eating, compulsive disorders, impulse control disorders, cognitive impairment and Alzheimer's disease.

  提供一种化合物，其化学式为（I），其中L1至L3，R1至R4，X，A和B的含义如描述中所给，并且其药学上可接受的盐、溶剂合物和前药，这些化合物可用作促进睡眠素-1和促进睡眠素-2受体的拮抗剂或作为促进睡眠素-1受体的选择性拮抗剂，因此，特别适用于治疗或预防物质依赖、成瘾、焦虑障碍、恐慌障碍、暴饮暴食、强迫障碍、冲动控制障碍、认知障碍和阿尔茨海默病等疾病。
• Substituted N, N-disubstituted diamino compounds useful for inhibiting cholesteryl ester transfer protein activity
  申请人：——

  公开号：US20020120011A1

  公开（公告）日：2002-08-29

  The invention relates to substituted polycyclic aryl and heteroaryl tertiary-heteroalkylamine compounds useful as inhibitors of cholesteryl ester transfer protein (CETP; plasma lipid transfer protein-I) and compounds, compositions and methods for treating atherosclerosis and other coronary artery diseases. Preferred tertiary-heteroalkylamine compounds are substituted N,N-disubstituted diamines. A preferred specific N,N-disubstituted diamine is the compound: 1

  这项发明涉及替代多环芳基和杂环芳基的三级杂烷基胺化合物，可用作胆固醇酯转移蛋白（CETP；血浆脂质转移蛋白-I）的抑制剂，以及用于治疗动脉粥样硬化和其他冠状动脉疾病的化合物、组合物和方法。首选的三级杂烷基胺化合物是取代的N,N-二取代二胺。首选的具体N,N-二取代二胺化合物是：1
• [EN] HEPATITIS C VIRUS INHIBITORS<br/>[FR] INHIBITEURS DU VIRUS DE L'HEPATITE C
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2003099274A1

  公开（公告）日：2003-12-04

  Hepatitis C virus inhibitors are disclosed having the general formula:(I) wherein R1, R2, R3, R', B, Y and X are described in the description. Compositions comprising the compounds and methods for using the compounds toinhibit HCV are also disclosed.

  丙型肝炎病毒抑制剂公开了具有以下通式：其中R1、R2、R3、R'、B、Y和X在描述中有所描述。还公开了包含该化合物的组合物以及使用该化合物抑制HCV的方法。