1-碘代戊炔 | 14752-61-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代乙炔及其衍生物
• 中文名称: 1-碘代戊炔
• 中文别名: 1-碘-1-戊炔
• 英文名称: 1-iodopent-1-yne
• 英文别名: 1-iodo-1-pentyne；pentynyl iodide；1-Iodopentyne；1-iodo-pent-1-yne；1-Jod-pent-1-in；1-Iod-pentin-(1)；1-Pentynyl Iodide
• CAS: 14752-61-5
• 化学式: C₅H₇I
• mdl: MFCD00059098
• 分子量: 194.015
• InChiKey: UWPKZGBPLFRGAH-UHFFFAOYSA-N

物化性质

• 沸点：
  53 °C / 22mmHg
• 密度：
  1,67 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险等级：
  3
• 安全说明：
  S16
• 危险类别码：
  R10
• 海关编码：
  2903399090
• 危险品运输编号：
  UN 1993
• 储存条件：
  室温

SDS

1-Pentynyl Iodide Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 1-Pentynyl Iodide

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS
Category 3
Flammable liquids
HEALTH HAZARDS Not classified
Not classified
ENVIRONMENTAL HAZARDS
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Flammable liquid and vapour
Precautionary statements:
[Prevention] Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
Keep container tightly closed.
Use explosion-proof electrical/ventilating/lighting equipment. Take precautionary
measures against ignition by the static discharge and the spark.
Wear protective gloves/eye protection/face protection.
[Response] IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse
skin with water/shower.
[Storage] Store in a well-ventilated place. Keep cool.
Dispose of contents/container through a waste management company authorized by
[Disposal]
the local government.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 1-Pentynyl Iodide
Percent: >97.0%(GC)
CAS Number: 14752-61-5
Synonyms: 1-Iodo-1-pentyne
C5H7I
Chemical Formula:

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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.
1-Pentynyl Iodide

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Section 4. FIRST AID MEASURES
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.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Unsuitable extinguishing Solid streams of water
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
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: Keep containers cool by
spraying with water. Eliminate all ignition sources 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
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Ensure adequate ventilation. Entry to non-involved personnel should be controlled
emergency procedures: around the leakage area by roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Absorb spilled material in dry sand or inert absorbent before recovering it into an
containment and cleaning airtight container. In case of large amount of spillage, contain a spill by bunding.
up: Adhered or collected material should be promptly disposed of, in accordance with
appropriate laws and regulations.
Prevention of secondary Remove all sources of ignition. Fire-extinguishing devices should be prepared in
hazards: case of a fire. Use spark-proof tools and explosion-proof equipment.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent generation of vapour or mist. Keep away from heat/sparks/open flame/hot
surfaces. -No smoking. Take measures to prevent the build up of electrostatic
charge. Use explosion-proof equipment. Wash hands and face thoroughly after
handling.
Use a closed system if possible. Use a ventilation, local exhaust if vapour 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, dark and well-ventilated 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
Engineering controls: Install a closed system or local exhaust. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Vapor respirator. Follow local and national regulations.
Hand protection: Protective gloves.
1-Pentynyl Iodide

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
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): Liquid
Form: Clear
Very pale yellow - Yellow
Colour:
Odour: No data available
pH: No data available
Melting point/freezing point:No data available
Boiling point/range: 53°C/2.9kPa
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: 1.67
Solubility(ies):
[Water] No data available
[Other solvents] No data available

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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:
Spark, Open flame, Static discharge
Conditions to avoid:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Hydrogen Iodide
products:

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

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
No data available
Crustacea:
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
No data available
Henry's Law
constant(PaM3/mol):
1-Pentynyl Iodide

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to 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: 3: Flammable liquid.
UN-No: 1993
Proper shipping name: Flammable liquid, n.o.s.
III
Packing group:

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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.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

聚合物添加剂在材料科学中扮演着重要角色。

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
  1-戊炔	1-Pentyne	627-19-0	C5H8	68.1185

反应信息

• 作为反应物：
  描述：

  1-碘代戊炔 在 bis(cyclohexanyl)borane 、 溶剂黄146 作用下， 以 正戊烷 为溶剂， 反应 0.08h， 以28%的产率得到(Z)-1-iodo-1-pentene
  参考文献：
  名称：

  前手性亲核烯烃与 α-手性 N-磺酰亚胺的非对映选择性加成

  摘要：

  描述了路易斯酸促进前手性E-和Z-烯丙基亲核试剂与手性 α-烷氧基N-甲苯磺酰基亚胺的加成。烯烃几何结构选择性地转移到新形成的碳-碳键上，从而对所得 2-烷氧基-3- N-甲苯磺酰基-4-烷基-5-己烯产物的 C1、C2 和 C3 进行立体化学控制。还提出了阐明高选择性的计算分析。该方法用于合成两种天然存在的硫磺酰胺异构体。

  DOI：

  10.1021/acs.orglett.1c04219
• 作为产物：
  描述：

  1-戊炔 在 正丁基锂 、 碘 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以75 %的产率得到1-碘代戊炔
  参考文献：
  名称：

  (4Z)-Lachnophyllum 内酯，一种对影响地中海农业的害虫具有植物毒性和抗真菌活性的代谢物：一种新的多功能且易于扩展的并行合成

  摘要：

  首次报道了克级的 (4 Z )-Lachnophyllum 内酯 ( 1 ) 的全合成和可调节合成方法。目前的工作从设计目标化合物的逆合成途径开始，关键步骤是 Pd-Cu 双金属级联交叉偶联环化。 ( 4Z )-Lachnophyllumlactone( 1 ) 是一种乙炔呋喃酮，之前从自养杂草Conyza bonariensis的有机提取物中分离出少量。在幼苗生长生物测定中针对茎寄生杂草菟丝子进行测试，与对照相比，( 4Z )-lachnophyllum内酯( 1 )显示出几乎85%的抑制活性，高达0.3mM。在相同浓度下，该化合物对根寄生杂草列当和山毛叶的根生长抑制活性分别高于70%和40%。令人惊讶的是，该化合物对C. bonariensis种子萌发也表现出高达 0.1 mM 的高抑制百分比。这种多功能合成策略还用于获得另外两种天然类似物，即 (4 E )-lachnophyllum

  DOI：

  10.1021/acs.jafc.3c07130

文献信息

• [EN] CONJUGATED UNSATURATED COMPOUNDS<br/>[FR] COMPOSÉS INSATURÉS CONJUGUÉS
  申请人：COMMW SCIENT IND RES ORG

  公开号：WO2009111830A1

  公开（公告）日：2009-09-17

  The present invention relates to a class of conjugated unsaturated compounds, to a method of preparing such compounds, and to the polymerisation and bio-active uses of such compounds including their use as antimicrobial agents. The invention particularly relates to compounds containing three conjugated unsaturated moieties, at least two of which are yne moieties.

  本发明涉及一类共轭不饱和化合物，涉及制备这类化合物的方法，以及这类化合物的聚合和生物活性用途，包括它们作为抗微生物剂的用途。该发明特别涉及含有三个共轭不饱和基团的化合物，其中至少有两个是炔基团。
• A Conia‐Ene‐Type Cyclization under Basic Conditions Enables an Efficient Synthesis of (−)‐Lycoposerramine R
  作者：Felix W. W. Hartrampf、Takayuki Furukawa、Dirk Trauner

  DOI：10.1002/anie.201610021

  日期：2017.1.16

  An enantioselective total synthesis of the Lycopodium alkaloid lycoposerramine R is presented. It relies on a base‐mediated cyclization that resembles the Conia‐ene reaction of ynones and gold‐catalyzed variants thereof. Thus, hydrindanones and other functionalized ring systems bearing an exocyclic alkene can be rapidly accessed at room temperature without noble metal catalysis or substrate preactivation

  提出了对映体总生物碱Lycopodium lycoposerramine R的合成。它依赖于碱基介导的环化反应，类似于炔酮及其金催化的变体的Conia-ene反应。因此，可以在室温下快速获得带有环外烯烃的苯并氢萘酮和其他官能化环系统，而无需贵金属催化或底物预活化。
• Nickel-Catalyzed Homocoupling of (Z)-β-Iodoenol Esters: Stereoselective Access to (Z,Z)-Buta-1,3-diene-1,4-diyl Diesters
  作者：Javier Francos、Victorio Cadierno

  DOI：10.1055/s-0037-1610709

  日期：2019.8

  use of a catalytic system composed of [NiCl2(PPh3)2] (10 mol%), NaI (10 mol%), and excess of Zn dust. The reactions proceed in THF at room temperature with exquisite preservation of the stereochemistry of the C=C bond of the starting iodoolefins, thus leading to the final dienes as the corresponding Z,Z-stereoisomers exclusively. A straightforward and broad-scope procedure to obtain symmetrically substituted

  致力于巴勃罗Espinet教授在他的70之际个生日 抽象的 提出了一种基于对应的（Z）-β-碘烯醇酯的均相偶联的，获得对称取代的buta-1,3-diene-1,4 -diyl disters的简单而广泛的方法。它涉及使用由[NiCl 2（PPh 3）2 ]（10摩尔％），NaI（10摩尔％）和过量的锌粉组成的催化体系。反应在室温下在THF中进行，并精确地保留了起始碘代烯烃的C ＝ C键的立体化学，因此最终形成最终的二烯，仅作为相应的Z，Z-立体异构体。 提出了一种基于对应的（Z）-β-碘烯醇酯的均相偶联的，获得对称取代的buta-1,3-diene-1,4 -diyl disters的简单而广泛的方法。它涉及使用由[NiCl 2（PPh 3）2 ]（10摩尔％），NaI（10摩尔％）和过量的锌粉组成的催化体系。反应在室温下在THF中进行，并精确地保留了起始碘代烯烃的C ＝ C键的立体化学
• Unsymmetrically substituted aliphatic diacetylenes
  作者：Eugen Barbu、John Tsibouklis

  DOI：10.1016/0040-4039(96)01025-8

  日期：1996.7

  A general method for the synthesis of pure samples of unsymmetrically disubstituted diacetylenes of the type CH3(CH2)nCCCCCH2OH (n=2,3,4,5) is described in detail. The materials could be polymerized thermally, in the liquid state.

  该类型的CH不对称二取代的丁二炔的纯样品的合成的一般方法3 （CH 2）Ñ CCCCCH 2描述OH（N = 2,3,4,5）详细地。该材料可以在液态下热聚合。
• Improved syntheses of methyl (14E)- and (14Z)-dehydrocrepenynate: key intermediates in plant and fungal polyacetylene biosynthesis
  作者：Lizhi Zhu、Robert E Minto

  DOI：10.1016/s0040-4039(01)00577-9

  日期：2001.6

  Efficient syntheses of the (14E)- and (14Z)-isomers of methyl dehydrocrepenynate have been achieved. The key steps involve Pd-catalyzed cross-coupling reactions furnishing the CC double bonds between C14 and C15, followed by Wittig reactions to construct the (Z)-alkene at C9. High overall yields and stereoselectivities were achieved for both isomers.

  已经实现了脱氢crepenynate的（14 E）-和（14 Z）异构体的高效合成。关键步骤包括在C14和C15之间提供C CC双键的Pd催化交叉偶联反应，然后进行Wittig反应，以在C9处构建（Z）烯烃。两种异构体均具有较高的总收率和立体选择性。