5-降冰片烯-2-甲酰胺 | 95-17-0

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 5-降冰片烯-2-甲酰胺
• 中文别名: 5-降冰片烯-2-酰胺；双环[2.2.1]庚-5-烯-2-甲酰胺
• 英文名称: 5-norbornene-2-carboxamide
• 英文别名: bicyclo<2.2.1>-5-hepten-2-carbonamide；endo-bicyclo<2.2.1>hept-5-ene-2-carboxamide；exo-bicyclo<2.2.1>hept-5-ene-2-carboxamide；bicyclo[2.2.1]hept-5-ene-2-carboxamide；Bicyclo<2.2.1>hept-5-en-2-carboxamid
• CAS: 95-17-0
• 化学式: C₈H₁₁NO
• mdl: MFCD00187896
• 分子量: 137.181
• InChiKey: ZTUUVDYQBLRAAC-UHFFFAOYSA-N

物化性质

• 熔点：
  188°C(lit.)
• 沸点：
  309.2±22.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.625
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi,C
• 海关编码：
  2924299090
• 危险类别：
  6.1
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 包装等级：
  III
• 危险品运输编号：
  2811
• 危险性防范说明：
  P233,P260,P261,P264,P271,P280,P302+P352,P304,P304+P340,P305+P351+P338,P312,P321,P332+P313,P337+P313,P340,P362,P403,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335

SDS

5-Norbornene-2-carboxamide (mixture of isomers)
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 5-Norbornene-2-carboxamide (mixture of isomers)

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
Not classified
HEALTH HAZARDS
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols None
No signal word
Signal word
Hazard statements None
None
Precautionary statements:

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 5-Norbornene-2-carboxamide (mixture of isomers)
Percent: >98.0%(HPLC)(N)
CAS Number: 95-17-0
Synonyms: Bicyclo[2.2.1]hept-5-ene-2-carboxamide (mixture of isomers)
Chemical Formula: C8H11NO

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
5-Norbornene-2-carboxamide (mixture of
isomers)

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Section 5. FIRE-FIGHTING MEASURES
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Use personal protective equipment. Keep people away from and upwind of spill/leak.
Personal precautions,
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Handling is performed in a well ventilated place. Wear suitable protective equipment.
Technical measures:
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Install a closed system or local exhaust as possible so that workers should not be
Engineering controls:
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Form: Crystal- Powder
White - Pale yellow
Colour:
Odour: No data available
pH: No data available
Melting point/freezing point:188°C
No data available
Boiling point/range:
Flash point: No data available
Flammability or explosive
limits:
No data available
Lower:
Upper: No data available
No data available
Relative density:
Solubility(ies):
No data available
[Water]
[Other solvents]
Dimethyl sulfoxide(DMSO)
Slightly soluble:
5-Norbornene-2-carboxamide (mixture of
isomers)

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx)
products:

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Section 11. TOXICOLOGICAL INFORMATION
No data available
Acute Toxicity:
Skin corrosion/irritation: No data available
No data available
Serious eye
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
No data available
IARC =
NTP = No data available
No data available
Reproductive toxicity:

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.
5-Norbornene-2-carboxamide (mixture of
isomers)

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途：5-降冰片烯-2-甲酰胺主要用于生化研究、作为标准品和对照品，以及医药中间体。

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
  (1R,2S,4R)-双环[2.2.1]-5-庚烯-2-羧酸	(1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid	120-74-1	C8H10O2	138.166
  ——	exo-5-norbornene-2-carboxylic acid	934-30-5	C8H10O2	138.166

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  5-降冰片烯-2-甲胺	5-norbornene-2-methylamine	95-10-3	C8H13N	123.198
  ——	N-phenyl-endo-bicyclo<2.2.1>hept-5-ene-2-carboxamide	52889-85-7	C14H15NO	213.279

反应信息

• 作为反应物：
  描述：

  5-降冰片烯-2-甲酰胺 在 4-二甲氨基吡啶 、 碘 、 三乙胺 、 sodium sulfite 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 (3S,3aR,5S,6S,6aS)-1-(tert-butyldimethylsilyl)-6-iodohexahydro-3,5-methanocyclopenta[b]pyrrol-2(1H)-one
  参考文献：
  名称：

  A procedure for “iodolactamization”

  摘要：

  DOI：

  10.1016/s0040-4039(00)94742-7
• 作为产物：
  描述：

  2-氰基-5-降冰片烯 在 RuCl2(η6-C6Me6)(1-benzyl-3,5-diaza-1-azonia-7-phosphaadamantane chloride) 、 水 作用下， 反应 3.0h， 以78%的产率得到5-降冰片烯-2-甲酰胺
  参考文献：
  名称：

  在纯水介质中，中性条件下钌的选择性钌催化水合为酰胺。

  摘要：

  DOI：

  10.1002/chem.200800847

文献信息

• Zirconium-hydride-catalyzed site-selective hydroboration of amides for the synthesis of amines: Mechanism, scope, and application
  作者：Bo Han、Jiong Zhang、Haijun Jiao、Lipeng Wu

  DOI：10.1016/s1872-2067(21)63853-6

  日期：2021.11

  diverse amines. Various readily reducible functional groups, such as esters, alkynes, and alkenes, were well tolerated. Furthermore, the methodology was extended to the synthesis of bio- and drug-derived amines. Detailed mechanistic studies revealed a reaction pathway entailing aldehyde and amido complex formation via an unusual C–N bond cleavage-reformation process, followed by C–O bond cleavage.

  开发用于选择性合成胺的温和高效的催化方法是一个长期的研究目标。在这方面，催化脱氧酰胺还原已被证明是有前途但具有挑战性的，因为这种方法需要选择性的 C-O 键裂解。在此，我们报告了伯、仲和叔酰胺在室温下由地球丰富的金属催化剂 Zr-H 催化的选择性硼氢化反应，以获取不同的胺。各种易于还原的官能团，如酯、炔烃和烯烃，都具有良好的耐受性。此外，该方法还扩展到生物和药物衍生胺的合成。详细的机理研究揭示了一个反应途径，通过一个不寻常的 C-N 键断裂-重整过程形成醛和酰胺复合物，然后是 C-O 键断裂。
• PYRIMIDINE INHIBITORS OF KINASES
  申请人：Curtin Michael

  公开号：US20100317680A1

  公开（公告）日：2010-12-16

  The present invention relates to compounds of formula (I) or pharmaceutical acceptable salts, wherein A 1 , A 2 , A 3 , A 4 , X and Y are defined in the description. The present invention relates also to methods of making said compounds, and compositions containing said compounds which are useful for inhibiting kinases such as aurora and KDR.

  本发明涉及式(I)的化合物或药用可接受的盐，其中A1、A2、A3、A4、X和Y在描述中有定义。本发明还涉及制备所述化合物的方法，以及含有所述化合物的组合物，用于抑制aurora和KDR等激酶。
• 一种酰胺化合物还原制备胺类化合物的方法
  申请人：中国科学院兰州化学物理研究所

  公开号：CN112299938A

  公开（公告）日：2021-02-02

  本发明涉及一种酰胺化合物还原制备胺类化合物的方法，该方法是指在保护气氛中，将酰胺类化合物或环状酰胺、锆金属催化剂、频哪醇硼烷混合，于室温条件下进行酰胺还原反应，12~48h后通过氯化氢的乙醚溶液后处理，即得胺的盐酸盐化合物。本发明操作简单、成本低且具有良好的官能团耐受性和广泛的底物范围。
• [EN] IMIDAZO [4, 5 - B] PYRIDINE DERIVATIVES AS ALK AND JAK MODULATORS FOR THE TREATMENT OF PROLIFERATIVE DISORDERS<br/>[FR] DÉRIVÉS IMIDAZO [4,5-B] PYRIDINE COMME MODULATEURS D'ALK ET DE JAK POUR LE TRAITEMENT DE TROUBLES PROLIFÉRATIFS
  申请人：CEPHALON INC

  公开号：WO2013116291A1

  公开（公告）日：2013-08-08

  This application relates to compounds of the Formula I as defined herein, and/or salts thereof. This application further relates to compositions and methods of using these compounds and/or salts thereof. The compounds of Formula I are useful as ALK and JAK modulators for the treatment of proliferative disorders.

  这项申请涉及到本文所定义的Formula I化合物及/或其盐。此申请进一步涉及到使用这些化合物和/或其盐的组合物和方法。Formula I化合物可用作ALK和JAK调节剂，用于治疗增殖性疾病。
• [EN] FUNGICIDAL 4-SUBSTITUTED-3-{PHENYL[(HETEROCYCLYLMETHOXY)IMINO]METHYL}-1,2,4-OXADIZOL-5(4H)-ONE DERIVATIVES<br/>[FR] DÉRIVÉS DE 3-{PHÉNYL[(HÉTÉROCYCLYLMÉTHOXY)IMINO]MÉTHYL}-1,2,4-OXADIZOL-5(4H)-ONE 4-SUBSTITUÉE FONGICIDES
  申请人：BAYER IP GMBH

  公开号：WO2013037717A1

  公开（公告）日：2013-03-21

  The present invention provides fungicidal 4-substituted-3-phenyl[(heterocyclylmethoxy)imino]methyl}-1,2,4-oxadiazol-5(4H)-one derivatives of formula (I) wherein A represents a pyridyl or thiazole group and X1, Y1 to Y5 represent independently different substituents.

  本发明提供了式(I)的杀真菌4-取代-3-苯基[(杂环甲氧基)亚胺]甲基}-1,2,4-噁二唑-5(4H)-酮衍生物，其中A代表吡啶基或噻唑基，X1、Y1至Y5代表独立不同的取代基。

表征谱图