1-羟基苯并三唑 | 2592-95-2

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 其他保护氨基酸
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 中文名称: 1-羟基苯并三唑
• 中文别名: 1-羟基苯并三氮唑(HOBT)；1-羟基苯骈三氮唑；1-羟基苯并三唑(HOBT)；1-羟基苯并三氮唑；1-羟基-苯并-三氮唑(HOBt)；1-羟基苯并三氮唑(无水)；1-羟基-苯并三氮唑；HOBt；N-羟基苯并三氮唑
• 英文名称: benzotriazol-1-ol
• 英文别名: 1-hydroxybenzotriazole；-hydroxybenzotriazole；HOBt；1H-benzo[d][1,2,3]triazol-1-ol；1H-benzotriazol-1-ol；HOAT；1H-1,2,3-benzotriazol-1-ol；1-hydroxybenzotriazole hydrate
• CAS: 2592-95-2
• 化学式: C₆H₅N₃O
• mdl: MFCD00005805
• 分子量: 135.125
• InChiKey: ASOKPJOREAFHNY-UHFFFAOYSA-N

物化性质

• 熔点：
  156-159°C
• 沸点：
  149-150 °C
• 密度：
  1 g/cm3
• 闪点：
  95 °C
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）
• LogP：
  0.146 at 25℃
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 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：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  4.1
• 危险品标志：
  F
• 安全说明：
  S15,S16,S26,S33,S45,S53,S7/9
• 危险类别码：
  R5,R11
• 海关编码：
  2933990090
• 危险品运输编号：
  1325
• 危险类别：
  4.1
• RTECS号：
  DM1288000
• 包装等级：
  III
• 储存条件：
  密封保存在阴凉干燥的环境中。

SDS

Name:	1-Hydroxybenzotriazole 98% Material Safety Data Sheet
Synonym:	HOB
CAS:	2592-95-2

Section 1 - Chemical Product MSDS Name:1-Hydroxybenzotriazole 98% Material Safety Data Sheet
Synonym:HOB

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2592-95-2	1-Hydroxybenzotriazole	98.0	219-989-7

Hazard Symbols: F
Risk Phrases: 11 44

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Highly flammable. Risk of explosion if heated under confinement.Light sensitive.
Potential Health Effects
Eye:
Dust may cause mechanical irritation. May cause lacrimation (tearing), blurred vision, and photophobia. May cause chemical conjunctivitis and corneal damage.
Skin:
May cause skin irritation and possible burns.
Ingestion:
May cause irritation of the digestive tract. May cause nausea, vomiting, abdominal pain, and increased salivation.
Inhalation:
Inhalation of dust may cause respiratory tract irritation. Olfactory fatigue may occur. Can produce delayed pulmonary edema.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid immediately. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If breathing is difficult, give oxygen. Get medical aid. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
Notes to Physician:

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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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Dust can be an explosion hazard when exposed to heat or flame. Flammable solid.
May burn rapidly with flare burning effect. May re-ignite after fire is extinguished. Containers may explode when heated. Risk of explosion if heated under confinement.
Extinguishing Media:
Use water spray to cool fire-exposed containers. For large fires, use water spray, fog or regular foam. Contact professional fire-fighters immediately. For small fires, use dry chemical, carbon dioxide, sand, earth, water spray or regular foam. Cool containers with flooding quantities of water until well after fire is out.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Scoop up with a nonsparking tool, then place into a suitable container for disposal. Avoid generating dusty conditions. Remove all sources of ignition. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed. Keep away from heat, sparks and flame. Avoid ingestion and inhalation. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames.
Storage:
Keep away from sources of ignition. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate general or local explosion-proof ventilation to keep airborne levels to acceptable levels.
Exposure Limits CAS# 2592-95-2: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: white
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 157 deg C dec
Autoignition Temperature: Not available.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: 157 deg C
Solubility in water: 0.3% (20C)
Specific Gravity/Density:
Molecular Formula: C6H5N3O
Molecular Weight: 135.12

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable. Heating above 180C results in rapid exothermic decomposition. Heating may cause an explosion.
Conditions to Avoid:
Incompatible materials, ignition sources, dust generation, excess heat, strong oxidants, heating above the melting point (155-158C).
Incompatibilities with Other Materials:
Strong oxidizing agents, copper nitrate.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, nitrogen.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 2592-95-2: DM1288000 LD50/LC50:
CAS# 2592-95-2: Draize test, rabbit, eye: 100 mg Mild.
Carcinogenicity:
1-Hydroxybenzotriazole - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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
Shipping Name: FLAMMABLE SOLID, ORGANIC, N.O.S.*
Hazard Class: 4.1
UN Number: 1325
Packing Group: III
IMO
Shipping Name: FLAMMABLE SOLID, ORGANIC, N.O.S.
Hazard Class: 4.1
UN Number: 1325
Packing Group: III
RID/ADR
Shipping Name: FLAMMABLE SOLID, ORGANIC, N.O.S.
Hazard Class: 4.1
UN Number: 1325
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: F
Risk Phrases:
R 11 Highly flammable.
R 44 Risk of explosion if heated under confinement.
Safety Phrases:
S 7/9 Keep container tightly closed and in a
well-ventilated place.
S 16 Keep away from sources of ignition - No
smoking.
S 33 Take precautionary measures against static
discharges.
WGK (Water Danger/Protection)
CAS# 2592-95-2: No information available.
Canada
CAS# 2592-95-2 is listed on Canada's DSL List.
CAS# 2592-95-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2592-95-2 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

性质

1-羟基苯并三唑（HOBT）常温常压下为白色或灰白色结晶固体状。其羟基在碱性条件下可以转变为相应的有机盐，因此可以在有机合成中与烷基卤代烃发生亲核取代反应生成烷基化衍生物。

应用

1-羟基苯并三唑（HOBT）广泛应用于有机合成和医药化学领域，常作为多肽类药物分子及生物活性分子的合成与衍生化的重要中间体。此外，它还用于化妆品生产中。

合成

在一个干燥的反应烧瓶中，将25毫摩尔水合肼（1.2毫升）加入到邻硝基氯苯（5毫摩尔）溶解在1-庚醇（10毫升）中的溶液里。然后，在110-120℃下搅拌该溶液5小时。反应结束后，用40%的NaOH水溶剂中和反应混合物，并在减压下除去多余的肼和1-庚醇。将pH值调节至3.2-3.5后，通过过滤收集沉淀产品。随后，使用冷却的5%氯化钠水溶液清洗沉淀物，最后在二氯甲烷和甲醇中进行重结晶提纯，即可得到目标产物分子。

图 1-羟基苯并三唑（HOBT）合成路线

用途

1-羟基苯并三唑（HOBT）用于多肽合成时，以DCC作为冷凝剂可抑制外消旋作用。 此外，它还用作合成乌苯美司的中间体、多肽保护剂以及有机合成中的重要中间体。

反应信息

• 作为反应物：
  描述：

  1-羟基苯并三唑 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 1H-1,2,3-benzotriazol-1-yl 4-amino-5-chloro-2-methoxybenzoate
  参考文献：
  名称：

  苯并三唑-1-基烷基碳酸酯，一种新的方便且廉价的偶联剂，用于制备用于合成酰胺的活性酯

  摘要：

  摘要 苯并三唑-1-基烷基碳酸酯 1 已被发现是一种新的方便且廉价的偶联剂，可用于制备活性酯 2，以高产率和高纯度合成酰胺 3。

  DOI：

  10.1080/00397919908086263
• 作为产物：
  描述：

  硝基氯苯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成 1-羟基苯并三唑
  参考文献：
  名称：

  N-芳基苯并三唑类氮氧衍生物及其合成方法

  摘要：

  本发明公开了一系列N‑芳基苯并三唑类氮氧衍生物及其合成方法。本发明所述的N‑芳基苯并三唑类氮氧衍生物具有如下式(I)所示结构，其制备方法为：取下述式(II)所示结构的N‑羟基苯并三唑衍生物、式(III)所示结构的有机硼试剂、铜盐和碱性物质，置于有机溶剂中，在氧气存在的条件下反应，制得目标物粗品。本发明所述方法简单易控，周期短；制得的部分N‑芳基苯并三唑类氮氧衍生物具有良好的抗肿瘤活性。所述式(I)、式(II)和式(III)所示结构的化合物分别如下：。

  公开号：

  CN105820132B
• 作为试剂：
  描述：

  在 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 N-(3’-(3-(3-(5,5-difluoro-7,9-dimethyl-5H-dipyrrolo[1,2-c:2’,1’-f][1,3,2]diazaborinin-3-yl)propanamido)propoxy)-[1,1’-biphenyl]-3-yl)-4-(5-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-3,6-dihydropyridine-1(2H)-carboxamide
  参考文献：
  名称：

  四氢吡啶 LIMK 抑制剂：结构活性研究和生物学表征

  摘要：

  LIM 激酶 LIMK1 和 LIMK2 已成为开发抑制剂的有前景的靶标，具有治疗多种主要疾病的潜在应用。 LIMK 作为 Rho-GTPase 家族小 G 蛋白的下游效应子，以及肌丝蛋白丝切蛋白（一种肌动蛋白解聚因子）的主要调节因子，在细胞骨架重塑中发挥着至关重要的作用。在本文中，我们描述了新型四氢吡啶吡咯并嘧啶 LIMK 抑制剂的概念、合成和生物学评价。首先构建同源模型是为了更好地理解我们初步化合物的结合模式并解释生物活性的差异。生成了包含 60 多种产品的库，并在中低纳摩尔范围内测量了酶活性。然后对最有前途的衍生物进行了肌动蛋白丝切蛋白磷酸化抑制的评估，从而鉴定出其在激酶选择性组中对 LIMKs 表现出优异的选择性。我们还证明它通过干扰肌动蛋白丝来影响细胞骨架。使用三种不同细胞系对该衍生物进行的细胞迁移研究显示出对细胞运动的显着影响。最终，解决了与LIMK2复合的激酶结构域的晶体结构

  DOI：

  10.1016/j.ejmech.2024.116391

文献信息

• [EN] PYRAZOLE DERIVATIVES USEFUL AS INHIBITORS OF FAAH<br/>[FR] DÉRIVÉS DE PYRAZOLE UTILES COMME INHIBITEURS DE FAAH
  申请人：MERCK & CO INC

  公开号：WO2009151991A1

  公开（公告）日：2009-12-17

  The present invention is directed to certain imidazole derivatives which are useful as inhibitors of Fatty Acid Amide Hydrolase (FAAH). The invention is also concerned with pharmaceutical formulations comprising these compounds as active ingredients and the use of the compounds and their formulations in the treatment of certain disorders, including osteoarthritis, rheumatoid arthritis, diabetic neuropathy, postherpetic neuralgia, skeletomuscular pain, and fibromyalgia, as well as acute pain, migraine, sleep disorder, Alzheimer disease, and Parkinson's disease

  本发明涉及某些咪唑衍生物，其可用作脂肪酰胺水解酶（FAAH）的抑制剂。该发明还涉及包含这些化合物作为活性成分的药物配方，以及这些化合物及其配方在治疗某些疾病中的使用，包括骨关节炎、类风湿性关节炎、糖尿病神经病变、带状疱疹后神经痛、骨骼肌肉疼痛和纤维肌痛，以及急性疼痛、偏头痛、睡眠障碍、阿尔茨海默病和帕金森病。
• PYRAZOLO[1,5a]PYRIMIDINE DERIVATIVES AS IRAK4 MODULATORS
  申请人：Arora Nidhi

  公开号：US20120015962A1

  公开（公告）日：2012-01-19

  Compounds of the formula I or II: wherein X, m, Ar, R 1 and R 2 are as defined herein. The subject compounds are useful for treatment of IRAK-mediated conditions.

  式I或II的化合物： 其中X，m，Ar，R1和R2如本文所定义。所述化合物对于治疗IRAK介导的疾病是有用的。
• [EN] S-NITROSOMERCAPTO COMPOUNDS AND RELATED DERIVATIVES<br/>[FR] COMPOSÉS DE S-NITROSOMERCAPTO ET DÉRIVÉS APPARENTÉS
  申请人：GALLEON PHARMACEUTICALS INC

  公开号：WO2009151744A1

  公开（公告）日：2009-12-17

  The present invention is directed to mercapto-based and S- nitrosomercapto-based SNO compounds and their derivatives, and their use in treating a lack of normal breathing control, including the treatment of apnea and hypoventilation associated with sleep, obesity, certain medicines and other medical conditions.

  本发明涉及基于巯基和S-亚硝基巯基的SNO化合物及其衍生物，以及它们在治疗正常呼吸控制缺失方面的用途，包括治疗与睡眠、肥胖、某些药物和其他医疗状况相关的呼吸暂停和低通气。
• SUBSTITUTED ARYL AND HETEROARYL CARBOXYLIC ACID HYDRAZIDES OR SALTS THEREOF AND USE THEREOF TO INCREASE STRESS TOLERANCE IN PLANTS
  申请人：BAYER CROPSCIENCE AKTIENGESELLSCHAFT

  公开号：US20180206495A1

  公开（公告）日：2018-07-26

  Substituted aryl- and heteroarylcarbonyl hydrazides The invention relates to substituted aryl- and heteroarylcarbonyl hydrazides of the general formula (I) or salts thereof where the radicals of the formula (I) are each as defined in the description for enhancing stress tolerance in plants to abiotic stress, and for enhancing plant growth and/or for increasing plant yield.

  该发明涉及通式（I）的取代芳基和杂芳基羰基肼或其盐，其中通式（I）的基团如描述中所定义，用于增强植物对非生物胁迫的耐受性，促进植物生长和/或增加植物产量。
• [EN] PSMA-TARGETING AMANITIN CONJUGATES<br/>[FR] CONJUGUÉS D'AMANITINE CIBLANT LE PSMA
  申请人：HEIDELBERG PHARMA RES GMBH

  公开号：WO2019057964A1

  公开（公告）日：2019-03-28

  The invention relates to a PSMA-targeting conjugate comprising (a) an amatoxin; (b) a small molecule PSMA-targeting moiety; and (c) optionally a linker linking said amatoxin and said small molecule PSMA-targeting moiety. The invention furthermore relates to a pharmaceutical composition comprising such conjugate.

  这项发明涉及一种PSMA靶向共轭物，包括(a)阿马毒素；(b)小分子PSMA靶向基团；以及(c)可选地连接所述阿马毒素和所述小分子PSMA靶向基团的连接剂。此外，该发明还涉及包含这种共轭物的药物组合物。

表征谱图