4-hydroxyimino-4,5,6,7-tetrahydro-[2,1,3]benzoxadiazole | 57153-55-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: 4-hydroxyimino-4,5,6,7-tetrahydro-[2,1,3]benzoxadiazole
• 英文别名: 6,7-dihydrobenzo[c][1,2,5]oxadiazol-4(5H)-one oxime；6,7-dihydro-2,1,3-benzoxadiazol-4(5H)-one oxime；4-hydroxyimino-4,5,6,7-tetrahydrobenzofurazan；6,7-dihydro-5H-benzo[1,2,5]oxadiazol-4-one oxime；6,7-dihydro-5H-benz[1,2,5]oxadiazol-4-one oxime；6,7-Dihydro-5H-benz[1,2,5]oxadiazol-4-on-oxim；N-(4,5,6,7-tetrahydro-2,1,3-benzoxadiazol-4-ylidene)hydroxylamine；N-(6,7-dihydro-5H-2,1,3-benzoxadiazol-4-ylidene)hydroxylamine
• CAS: 57153-55-6
• 化学式: C₆H₇N₃O₂
• mdl: MFCD00673161
• 分子量: 153.14
• InChiKey: MPQCYPOGJHSLHA-UHFFFAOYSA-N

物化性质

• 熔点：
  166-168°C

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 安全说明：
  S22,S24/25

SDS

Name:	4 5 6 7-Tetrahydro-2 1 3-benzoxadiazol-4-one oxime 97% Material Safety Data Sheet
Synonym:
CAS:	57153-55-6

Section 1 - Chemical Product MSDS Name:4 5 6 7-Tetrahydro-2 1 3-benzoxadiazol-4-one oxime 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
57153-55-6	4,5,6,7-Tetrahydro-2,1,3-benzoxadiazol	97%	unlisted

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# 57153-55-6: 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: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 166 - 168 deg C
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: C6H7N3O2
Molecular Weight: 153

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 57153-55-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4,5,6,7-Tetrahydro-2,1,3-benzoxadiazol-4-one oxime - 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# 57153-55-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 57153-55-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 57153-55-6 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

反应信息

• 作为反应物：
  描述：

  4-hydroxyimino-4,5,6,7-tetrahydro-[2,1,3]benzoxadiazole 在 盐酸 、 聚合甲醛 作用下， 反应 0.33h， 以87.5%的产率得到4,5,6,7-四氢-2,1,3-苯并噁二唑-4-酮
  参考文献：
  名称：

  苯并二呋喃，苯并二呋喃和苯并呋喃氮杂呋喃的4,5'-二氢衍生物的合成

  摘要：

  DOI：

  10.1007/bf00486813
• 作为产物：
  描述：

  1,2,3-环己三酮三肟 在 氯化亚砜 作用下， 以 liquid sulphur dioxide 为溶剂， 生成 4-hydroxyimino-4,5,6,7-tetrahydro-[2,1,3]benzoxadiazole
  参考文献：
  名称：

  1, 2-环戊二酮二肟和1, 2, 3-和1,3,5-环己三酮三肟在液态二氧化硫中的反应

  摘要：

  1, 2-环戊二酮二肟 (II)、1, 2, 3-环己三酮三肟 (III) 和 1, 3, 5-环己三酮三肟 (IV) 经试剂处理后在液态二氧化硫中表现出不同的特征行为。通过缩合反应从 II 与亚硫酰氯形成 5, 6-二氢-4H-环戊-[c] 呋喃 (V) 和通过裂解反应从 II 与三氧化硫形成 γ-氰基丁酸 (VI) 是观察到的。在来自 III 和亚硫酰氯以及来自 III 和溴的反应混合物中发现了 7-Hydroxi-rnino-4, 5, 6, 7-四氢苯并[c]呋喃 (VII)，并伴有大量树脂物质。建议通过三氧化硫进行单脱肟。1, 3, 5-环己三酮三肟 (IV) 仅产生黑色焦油状物质，这可能是由于 IV 的不稳定性所致。

  DOI：

  10.1246/bcsj.35.722

文献信息

• Semmler-Wolff aromatization of 4-hydroxyimino-4,5,6,7-tetrahydro-[2,1,3]benzoxadiazole and 4-hydroxyimino-4,5,6,7-tetrahydro[2,1,3]benzoxadiazole 1-oxide and some properties of the obtained amines
  作者：V. A. Samsonov、G. E. Salʼnikov、L. B. Volodarskii

  DOI：10.1007/s10593-010-0596-9

  日期：2010.11

  The Semmler-Wolff aromatization of 4-hydroxyimino-4,5,6,7-tetrahydro[2,1,3]benzoxadiazole and its 1-oxide derivative in sulfuric acid and in acetic anhydride gave 4-amino[2,1,3]benzoxadiazole and 4-acetamido[2,1,3]benzoxadiazole 1-oxide. Some reactions of the resultant amines were studied.

  在硫酸和乙酸酐中将4-羟基亚氨基-4,5,6,7-四氢[2,1,3]苯并恶二唑及其1-氧化物衍生物进行Semmler-Wolff芳构化，得到4-氨基[2,1,3 ]苯并二唑和4-乙酰氨基[2,1,3]苯并二唑1-氧化物。研究了所得胺的一些反应。
• REACTION OF THE SODIUM SALT OF 2-HYDROXYIMINOCYCLO-HEXANONE WITH HYDROXYLAMMONIUM CHLORIDE
  作者：CHARLES V. BANKS、JAMES L. PFLASTERER

  DOI：10.1021/jo01131a006

  日期：1953.3
• 1,2,5-Oxadiazolo[3,4-g]indoles via annelation of 6,7-dihydrobenzo[c][1,2,5]oxadiazol-4(5H)-one oxime with acetylene
  作者：Arsalan B. Budaev、Andrei V. Ivanov、Olga V. Petrova、Vladimir A. Samsonov、Igor A. Ushakov、Aleksei Ya. Tikhonov、Lyubov N. Sobenina、Boris A. Trofimov

  DOI：10.1016/j.mencom.2019.01.016

  日期：2019.1

  6,7-Dihydrobenzo[c][1,2,5]oxadiazol-4(5H)-one oxime is annelated with acetylene in the KOH/DMSO/H2O system under pressure to give NH- or N-vinyl-5,8-dihydro-4H-[1,2,5]-oxadiazolo[3,4-g]indoles in 29 and 68% yields, respectively. These derivatives are readily aromatized with DDQ at room temperature to the expected indoles.
• From 1,2,5-Oxadiazolo[3,4-g]indoles to Pyrrolo[2,3-f]quinoxalines in One Preparative Stage
  作者：A. B. Budaev、A. V. Ivanov、O. V. Petrova、A. Ya. Tikhonov、V. A. Samsonov、L. N. Sobenina、B. A. Trofimov

  DOI：10.1134/s1070428019020234

  日期：2019.2

  Pyrrolo[2,3-f]quinoxalines are synthesized by heating 1,2,5-oxadiazolo[3,4-g]indoles with ethanolamine in the presence of p-toluenesulfonic acid.
• The Reactions of 1, 2-Cyclopentanedione Dioxime and of 1, 2, 3-and 1,3,5-Cyclohexanetrione Trioximes in Liquid Sulfur Dioxide
  作者：Niichiro Tokura、Isoo Shirai、Tokuji Sugahara

  DOI：10.1246/bcsj.35.722

  日期：1962.5

  2-Cyclopentanedione dioxime (II), 1, 2, 3-cyclohexanetrione trioxime (III) and 1, 3, 5-cyclohexanetrione trioxime (IV) were treated with reagents and exhibited different and characteristic behaviors in liquid sulfur dioxide. The formation of 5, 6-dihydro-4H-cyclopenta-[c] furazan (V) from II with thionyl chloride by a condensation reaction and of γ-cyanobu-tyric acid (VI) from II with sulfur trioxide by

  1, 2-环戊二酮二肟 (II)、1, 2, 3-环己三酮三肟 (III) 和 1, 3, 5-环己三酮三肟 (IV) 经试剂处理后在液态二氧化硫中表现出不同的特征行为。通过缩合反应从 II 与亚硫酰氯形成 5, 6-二氢-4H-环戊-[c] 呋喃 (V) 和通过裂解反应从 II 与三氧化硫形成 γ-氰基丁酸 (VI) 是观察到的。在来自 III 和亚硫酰氯以及来自 III 和溴的反应混合物中发现了 7-Hydroxi-rnino-4, 5, 6, 7-四氢苯并[c]呋喃 (VII)，并伴有大量树脂物质。建议通过三氧化硫进行单脱肟。1, 3, 5-环己三酮三肟 (IV) 仅产生黑色焦油状物质，这可能是由于 IV 的不稳定性所致。