反式-4-氯-2-丁醇 | 1775-39-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 反式-4-氯-2-丁醇
• 中文别名: 反-4-氯巴豆醇
• 英文名称: 1-chloro-4-hydroxy-2-butene
• 英文别名: trans-4-hydroxy-2-butenyl chloride；(E)-1-chloro-4-hydroxy-2-butene；(E)-1-chloro-2-butene-4-ol；(E)-4-chloro-2-buten-1-ol；1-Chloro-2-butene-4-ol；4-chlorobut-2-enol；trans-4-Chloro-2-butene-1-OL；(E)-4-chlorobut-2-en-1-ol
• CAS: 1775-39-9
• 化学式: C₄H₇ClO
• 分子量: 106.552
• InChiKey: WVRLAHTVGOLBEB-OWOJBTEDSA-N

物化性质

• 沸点：
  182.8±28.0 °C(Predicted)
• 密度：
  1.097±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2905590090

SDS

Name:	Trans-4-Chloro-2-Buten-1-ol Material Safety Data Sheet
Synonym:	None Known
CAS:	1775-39-9

Section 1 - Chemical Product MSDS Name:Trans-4-Chloro-2-Buten-1-ol Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1775-39-9	Trans-4-Chloro-2-Buten-1-ol	ca. 100	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Irritating to eyes, respiratory system and skin.Lachrymator (substance which increases the flow of tears).
Potential Health Effects
Eye:
Produces irritation, characterized by a burning sensation, redness, tearing, inflammation, and possible corneal injury. Lachrymator (substance which increases the flow of tears). May cause chemical conjunctivitis.
Skin:
Causes skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause gastrointestinal irritation with nausea, vomiting and diarrhea.
Inhalation:
Harmful if inhaled. Causes respiratory tract irritation. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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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. Do NOT allow victim to rub eyes or keep eyes closed.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. 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 not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. Do NOT use mouth-to-mouth resuscitation.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas.
Extinguishing Media:
Use water spray to cool fire-exposed containers. Use foam, dry chemical, or carbon dioxide.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
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 ventilation to keep airborne concentrations low.
Exposure Limits CAS# 1775-39-9: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 65 deg C @ 3mmHg
Freezing/Melting Point: Not available.
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: C4H7ClO
Molecular Weight: 106.55

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not currently available.
Conditions to Avoid:
None reported.
Incompatibilities with Other Materials:
Oxidizing agents, strong bases.
Hazardous Decomposition Products:
Hydrogen chloride, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1775-39-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Trans-4-Chloro-2-Buten-1-ol - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
WGK (Water Danger/Protection)
CAS# 1775-39-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1775-39-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1775-39-9 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：

  反式-4-氯-2-丁醇 在 sodium iodide 作用下， 以 乙腈 为溶剂， 生成 (E)-5-hydroxypent-3-enenitrile
  参考文献：
  名称：

  Oligomeric phosphite, phosphodiester, Phosphorothioate and

  摘要：

  提供了合成过程，其中制备了具有磷酸二酯、磷硫酸酯和磷二硫酸酯共价键的寡聚化合物。还提供了在这些过程中有用的合成中间体。

  公开号：

  US05705621A1
• 作为产物：
  描述：

  反-2-丁烯-1,4-二醇 在 三苯基膦 、 N-氯代丁二酰亚胺 作用下， 以 四氢呋喃 为溶剂， 以55%的产率得到反式-4-氯-2-丁醇
  参考文献：
  名称：

  铜催化的 [2,3]- 和 [1,2]- 碘鎓叶立德重排中配体控制的区域发散

  摘要：

  尽管烯丙基叶立德重排对于复杂分子的合成很重要，[2,3]-和[1,2]-重排的催化剂控制仍然是一个未解决的问题。我们开发了第一个由带有不同配体的铜催化剂控制的碘鎓叶立德的区域发散[2,3]-和[1,2]-重排。在 2,2'-联吡啶配体存在下，重氮酯和烯丙基碘通过 [2,3]-重排途径发生反应。或者，膦配体有利于形成[1,2]-重排产物。以高产率、区域选择性和非对映选择性获得了一系列含有广泛官能团的 α-碘酯。氘标记研究表明区域选择性重排的不同机制。

  DOI：

  10.1021/jacs.6b08624

文献信息

• Asymmetric Reductive Carbocyclization Using Engineered Ene Reductases
  作者：Kathrin Heckenbichler、Anna Schweiger、Lea Alexandra Brandner、Alexandra Binter、Marina Toplak、Peter Macheroux、Karl Gruber、Rolf Breinbauer

  DOI：10.1002/anie.201802962

  日期：2018.6.11

  bearing an electron‐withdrawing group, for example, a carbonyl group. This asymmetric reduction has been exploited for biocatalysis. Going beyond its canonical function, we show that members of this enzyme family can also catalyze the formation of C−C bonds. α,β‐Unsaturated aldehydes and ketones containing an additional electrophilic group undergo reductive cyclization. Mechanistically, the two‐electron‐reduced

  来自老黄酶 (OYE) 家族的烯还原酶可还原带有吸电子基团（例如羰基）的 α,β-不饱和化合物中的 C=C 双键。这种不对称还原已被用于生物催化。除了其典型功能之外，我们还发现该酶家族的成员还可以催化 C−C 键的形成。含有额外亲电基团的 α,β-不饱和醛和酮会发生还原环化。从机制上讲，双电子还原酶辅因子 FMN 传递氢化物以生成烯醇化物中间体，该中间体与内部亲电子试剂发生反应。用非质子 Phe 或 Trp 单位点取代关键的 Tyr 残基有利于环化反应而不是自然还原反应。新的转化使得对映选择性合成手性环丙烷的效率高达 >99% 。
• Allylic Disulfide Rearrangement and Desulfurization:  Mild, Electrophile-Free Thioether Formation from Thiols
  作者：David Crich、Franck Brebion、Venkataramanan Krishnamurthy

  DOI：10.1021/ol061381+

  日期：2006.8.1

  see text] Secondary and tertiary allylic 2-pyridyl and 2-benzothiazolyl disulfides react with thiol groups at room temperature to give secondary and tertiary allyl alkyl disulfides. On the addition of a phosphine, a desulfurative sigmatropic rearrangement takes place at room temperature to give thioethers.

  [反应：见正文]仲和叔烯丙基2-吡啶基和2-苯并噻唑基二硫化物在室温下与巯基反应，得到仲和叔烯丙基烷基二硫化物。加入膦后，在室温下发生脱硫的σ重排，得到硫醚。
• Absolute molecular weight polymers and methods for their use
  申请人：Alcon Laboratories, Inc.

  公开号：US05547663A1

  公开（公告）日：1996-08-20

  A process for preparing defined molecular weight polymers, particularly polyquaternary ammonium compounds, is disclosed. As the molecular weights of these compounds can be absolutely defined, rather than defined merely in terms of "number average molecular weight," these compounds are particularly useful as identification standards for other polymers which are made using conventional polymerization processes. The polyquaternary ammonium compounds described are further suitable for use as antimicrobial agents, particularly in ophthalmic compositions.

  本文公开了一种制备定义分子量聚合物的方法，特别是聚季铵盐化合物。由于这些化合物的分子量可以绝对定义，而不仅仅是以“数均分子量”来定义，因此这些化合物特别适用作为使用传统聚合过程制备的其他聚合物的标准。所述的聚季铵盐化合物进一步适用于用作抗菌剂，特别是在眼科配方中。
• Process for the synthesis of oligomeric compounds
  申请人：Isis Pharmaceuticals, Inc.

  公开号：US06051699A1

  公开（公告）日：2000-04-18

  Synthetic processes are provided wherein oligomeric compounds are prepared having phosphodiester, phosphorothioate, and phosphorodithioate covalent linkages. Also provided are synthetic intermediates useful in the processes.

  提供了合成过程，其中制备具有磷酸二酯、磷硫酸酯和磷二硫酸酯共价键的寡聚合物化合物。还提供了在这些过程中有用的合成中间体。
• One-step radiosynthesis of [18F]LBT-999: a selective radioligand for the visualization of the dopamine transporter with PET
  作者：Frédéric Dollé、Julie Helfenbein、Françoise Hinnen、Sylvie Mavel、Zoïa Mincheva、Wadad Saba、Marie-Anne Schöllhorn-Peyronneau、Heric Valette、Lucette Garreau、Sylvie Chalon、Christer Halldin、Jean-Claude Madelmont、Jean-Bernard Deloye、Michel Bottlaender、Joël Le Gailliard、Denis Guilloteau、Patrick Emond

  DOI：10.1002/jlcr.1412

  日期：2007.7

  LBT-999 (8-((E)-4-fluoro-but-2-enyl)-3-beta-p-tolyl-8-aza-bicyclo[3.2.1]octane-2-beta-carboxylicacid methyl ester) is a recently developed cocaine derivative belonging to a new generation of highly selective dopamine transporter (DAT) ligands (KD: 9 nM for the DAT and IC50 > 1000 nM for the serotonin and norepinephrine transporter). Initial fluorine-18-labelling of LBT-999 was based on the robust and reliable two-step radiochemical pathway often reported for such tropane derivatives, involving first the preparation of (E)-1-[18F]fluoro-4-tosyloxybut-2-ene followed by a N-alkylation reaction with the appropriate nor-tropane moiety. In the present work, a simple one-step fluorine-18-labelling of LBT-999 is reported, based on a chlorine-for-fluorine nucleophilic aliphatic substitution, facilitating as expected both automation and final high-performance liquid chromatography (HPLC) purification. The process involves: (A) reaction of K[18F]F–Kryptofix®222 with the chlorinated precursor (3.5–4.5 mg) at 165°C for 10 min in DMSO (0.6 mL) followed by (B) C-18 PrepSep cartridge pre-purification and finally (C) semi-preparative HPLC purification on a Waters Symmetry® C-18. Typically, 3.70–5.92 GBq of [18F]LBT-999 (> 95% chemically and radiochemically pure) could be obtained with specific radioactivities ranging from 37 to 111 GBq/µmol within 85–90 min (HPLC purification and Sep-Pak-based formulation included), starting from a 37.0 GBq [18F]fluoride batch (overall radiochemical yields: 10–16%, non-decay-corrected). Copyright © 2007 John Wiley & Sons, Ltd.

  LBT-999（8-((E)-4-氟-丁-2-烯基)-3-β-对甲苯基-8-氮杂双环[3.2.1]辛烷-2-β-羧酸甲酯）是最近开发的一种可卡因衍生物，属于新一代高选择性多巴胺转运体（DAT）配体（DAT 的 KD：9 nM，5-羟色胺和去甲肾上腺素转运体的 IC50 > 1000 nM）。LBT-999 最初的氟-18 标记是基于此类托烷衍生物经常报道的稳健可靠的两步放射化学途径，首先制备 (E)-1-[18F]氟-4-tosyloxybut-2-ene，然后与适当的正托烷分子进行 N- 烷基化反应。本研究报告了一种简单的一步法氟-18 标记 LBT-999，该方法基于氯对氟的亲核脂肪族取代，有助于实现自动化和最终的高效液相色谱（HPLC）纯化。该过程包括：(A) K[18F]F-Kryptofix®222 与氯化前体（3.5-4.5 毫克）在 165°C 下于 DMSO（0.6 毫升）中反应 10 分钟，然后 (B) C-18 PrepSep 滤芯预纯化，最后 (C) 在 Waters Symmetry® C-18 上进行半制备型 HPLC 纯化。通常情况下，从 37.0 GBq [18F]氟化物批次开始，在 85-90 分钟内可获得 3.70-5.92 GBq [18F]LBT-999（化学纯度和放射化学纯度大于 95%），特定放射性活度范围为 37-111 GBq/µmol（包括 HPLC 纯化和基于 Sep-Pak 的配方）（总体放射化学收率：10-16%，非衰变校正）。Copyright © 2007 John Wiley & Sons, Ltd. All Rights Reserved.