1,2,3-三氯丙烯 | 96-19-5

• 物质功能分类: 化学农药原药 - 除草剂 - 氨基甲酸酯类除草剂
• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 中文名称: 1,2,3-三氯丙烯
• 英文名称: 1,2,3-trichloropropene
• 英文别名: 1,2,3-Trichlor-propen；1,2,3-Trichloro-1-propene；1,2,3-trichloroprop-1-ene
• CAS: 96-19-5
• 化学式: C₃H₃Cl₃
• mdl: MFCD01696328
• 分子量: 145.416
• InChiKey: HIILBTHBHCLUER-UHFFFAOYSA-N

物化性质

• 熔点：
  -30°C (estimate)
• 沸点：
  145°C
• 密度：
  1,43 g/cm3
• 闪点：
  82°C
• 溶解度：
  乙腈（少量溶解）、氯仿（少量溶解）、DMSO（少量溶解）、甲醇（少量溶解）
• 物理描述：
  1,2,3-trichloropropene appears as an amber liquid. May be absorbed through the skin. Vapors are heavier than air. Contact with vapors or liquid may cause burns or irritation.
• 蒸汽压力：
  vapor pressure = 4.4 mm Hg @ 25 °C
• 分解：
  WHEN HEATED TO DECOMP, IT PRODUCES TOXIC FUMES.
• 折光率：
  INDEX OF REFRACTION: 1.5030 @ 20 °C/D
• 稳定性/保质期：
  有毒，对人体的肺和胃有刺激作用，因为产品中含有微量氯丙酮，因此具有催泪性。操作时应穿戴好防护用品；若衣物被污染，应立即更换。

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

毒理性

• 非人类毒性摘录

该化合物在兔眼外部进行了测试，根据24小时后观察到的伤害程度，在1到10的刻度上进行评分。最严重伤害的物质被评为了10。1,2,3-三氯丙烯在兔眼上的评分为5。

The compound was tested externally on the eyes of rabbits, and, according to the degree of injury observed after 24 hours, rated on a scale of 1 to 10. The most severely injurious substances have been rated 10. 1,2,3-Trichloropene rated 5 on rabbit eyes.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

Sprague-Dawley 大鼠，金色叙利亚仓鼠每天暴露于25 ppm 6小时，每周5天，持续94天，出现眼睛和上呼吸道刺激；雄性仓鼠和两种性别的大鼠体重下降；大鼠的SGPT升高，雄性仓鼠肝脏细胞体积减小。

SPRAGUE-DAWLEY RATS, GOLDEN SYRIAN HAMSTERS EXPOSED TO 25 PPM 6 HR DAILY, 5 DAYS/WK, 94 DAYS, REVEALED EYE & UPPER RESP TRACT IRRITATION; DECR BODY WT IN MALE HAMSTERS & BOTH SEXES OF RATS; ELEVATED SGPT IN RATS, DECR LIVER CELL SIZE IN MALE HAMSTER LIVERS.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

在大鼠和叙利亚仓鼠中进行的肝脏非蛋白巯基（NPSH）检测表明，单次吸入暴露产生的剂量相关肝脏NPSH浓度降低在大鼠和仓鼠中均可观察到，但在重复暴露后并未发现这种现象。

HEPATIC NONPROTEIN SULFHYDRYL (NPSH) ASSAYS IN SPRAGUE-DAWLEY RATS & SYRIAN HAMSTERS GIVEN SINGLE INHALATION EXPOSURES PRODUCED DOSE-RELATED DECR OF HEPATIC NPSH CONCN IN BOTH RATS & HAMSTERS, WHICH WAS NOT OBSERVED AFTER REPEATED EXPOSURES.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

在接触10和25 ppm的狗中观察到眼部刺激。

EYE IRRITATION WAS OBSERVED IN DOGS EXPOSED TO 10 & 25 PPM.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• TSCA 测试提交

1,2,3-三氯丙烯在鼠伤寒沙门氏菌测试株TA98、TA100和TA1535（Ames试验）中的致突变性进行了评估，分别考察了在有和无Aroclor诱导的大鼠肝脏S9代谢活化作用的情况。根据初步毒性测定，使用液体预孵化技术，在最高达0.28微升/平板的浓度下对1,2,3-三氯丙烯进行了测试。1,2,3-三氯丙烯在TA100测试株中，在代谢活化作用下产生了阳性反应。

The mutagenicity of 1,2,3-trichloropropene was evaluated in Salmonella tester strains TA98, TA100 and TA1535 (Ames Test), both in the presence and absence of Aroclor-induced rat liver S9 metabolic activation. Based on preliminary toxicity determinations, 1,2,3-trichloropropene, was tested at concentrations up to 0.28ul/plate using the liquid preincubation technique. 1,2,3-Trichloropropene produced a positive response in tester strain TA100 with metabolic activation.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  6.1(b)
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R20/21/22,R36/37/38
• 危险品运输编号：
  2810
• RTECS号：
  UD2450000
• 海关编码：
  2903299090
• 包装等级：
  III
• 危险类别：
  6.1(b)
• 储存条件：
  自用时以管道运输，外销则可用铁桶包装。

SDS

1,2,3-Trichloropropene (cis- and trans- mixture)
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 1,2,3-Trichloropropene (cis- and trans- mixture)

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS
Category 4
Flammable liquids
HEALTH HAZARDS
Category 4
Acute toxicity (Oral)
Acute toxicity (Dermal) Category 3
Category 2
Acute toxicity (Inhalation)
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
Specific target organ toxicity Respiratory tract irritation
- Single exposure [Category 3]
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Danger
Signal word
Hazard statements Combustible liquid
Harmful if swallowed
Toxic in contact with skin
Fatal if inhaled
Causes skin irritation
Causes serious eye irritation
May cause respiratory irritation
Precautionary statements:
[Prevention] Keep away from flames and hot surfaces.
Do not breathe dust/fume/gas/mist/vapours/spray.
Use only outdoors or in a well-ventilated area.
Do not eat, drink or smoke when using this product.
Wash hands thoroughly after handling.
Wear respiratory protection.
Wear protective gloves and eye/face protection.

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Section 2. HAZARDS IDENTIFICATION
[Response] IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for
breathing. Immediately call a POISON CENTER or doctor/physician.
IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell.
Rinse mouth.
IF IN EYES: 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.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Remove/Take off immediately all contaminated clothing.
Wash contaminated clothing before reuse.
Call a POISON CENTER or doctor/physician if you feel unwell.
[Storage] Store in a well-ventilated place. Keep container tightly closed.
Store locked up.
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
Substance/mixture:
Components: 1,2,3-Trichloropropene (cis- and trans- mixture)
Percent: >95.0%(GC)
CAS Number: 96-19-5
Chemical Formula: C3H3Cl3

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Section 4. FIRST AID MEASURES
Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Inhalation:
Immediately call a POISON CENTER or doctor/physician.
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. Call a POISON CENTER or doctor/physician.
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: Call a POISON CENTER or doctor/physician 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:
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: 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 extra personal protective equipment (self-contained breathing apparatus). Keep
Personal precautions,
protective equipment and people away from and upwind of spill/leak. Ensure adequate ventilation. Entry to non-
emergency procedures: involved personnel should be controlled around the leakage area by roping off, etc.
Environmental precautions: Prevent product from entering drains.

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Section 6. ACCIDENTAL RELEASE MEASURES
Methods and materials for Absorb spilled material in a suitable absorbent (e.g. rag, dry sand, earth, saw-dust).
containment and cleaning In case of large amount of spillage, contain a spill by bunding. Adhered or collected
up: 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 flames and hot surfaces. 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, ventilation.
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 locked up.
Store away from incompatible materials such as oxidizing agents.
Comply with laws.
Packaging material:

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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: Half or full facepiece respirator, self-contained breathing apparatus(SCBA), supplied
air respirator, etc. Use respirators approved under appropriate government standards
and follow local and national regulations.
Impervious gloves.
Hand protection:
Eye protection: Safety goggles. A face-shield, if the situation requires.
Skin and body protection: Impervious 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
Colorless - Very pale yellow
Colour:
Odour: No data available
pH: No data available
Melting point/freezing point:No data available
Boiling point/range: 145°C
Flash point: 82°C
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: 1.43
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:
Open flame
Conditions to avoid:
Incompatible materials: Oxidizing agents

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Section 10. STABILITY AND REACTIVITY
Hazardous decomposition Carbon monoxide, Carbon dioxide, Hydrogen chloride
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: ihl-rat LCLo:500 ppm/4H
orl-rat LD50:616 mg/kg
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
RTECS Number: UD2450000

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
No data available
Fish:
Crustacea: No data available
No data available
Algae:
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
Log Pow: No data available
No data available
Soil adsorption (Koc):
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 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: 6.1: Toxic substance.
2810
UN-No:
Proper shipping name: Toxic liquid, organic, n.o.s.
II
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

化学性质
本品为无色液体，沸点142℃，相对密度1.414，易溶于四氯化碳和氯仿，不溶于水。

用途
1,2,3-三氯丙烯是除草剂燕麦敌的中间体。

生产方法
其制备方法为：将四氯丙烷与乙醇加入反应釜中，搅拌并加热至回流。在1小时内分批加入氢氧化钾，加毕后继续回流2小时，随后冷却、过滤，滤液用水洗两次，水层用二氯乙烷萃取，并与油层合并，脱溶剂后减压蒸馏，收集74～91℃/13.3 kPa的馏分即为成品。

反应方程式如下：
Cl₂CH₂Cl + KOH → Cl₂CH₂C=CHCl + KCl + H₂O

反应信息

• 作为反应物：
  描述：

  1,2,3-三氯丙烯 在 氯 作用下， 反应 3.5h， 生成 五氯丙烷
  参考文献：
  名称：

  [EN] PROCESS FOR THE PRODUCTION OF CHLORINATED PROPANES AND/OR PROPENES
  [FR] PROCÉDÉ POUR LA PRODUCTION DE PROPANES ET/OU PROPÈNES CHLORÉS

  摘要：

  提供了生产氯代丙烷和/或丙烯的工艺。本工艺利用甲基乙炔作为低成本的起始材料，甲基乙炔是生产乙烯和/或丙烯的副产物，可以单独使用或与丙二烯、丙烯和/或丙烷结合使用。在后者的实施例中，该工艺还可用于提供一个基本纯净的丙烷流。

  公开号：

  WO2013074394A1
• 作为产物：
  描述：

  1,2,3-Trichlor-2-brom-propan 在 sodium hydroxide 作用下， 生成 1,2,3-三氯丙烯
  参考文献：
  名称：

  Kirrmann; Kremer, Bulletin de la Societe Chimique de France, 1948, p. 168

  摘要：

  DOI：

文献信息

• A Mild and Convenient Barbier-Type Allylation of Aldehydes to Homoallylic Alcohols via Iodide Ion Promoted Stannylation of Allylic Bromides and Chlorides with Tin(II) Chloride
  作者：Toshiro Imai、Shinya Nishida

  DOI：10.1055/s-1993-25871

  日期：——

  Barbier-type allylation of aldehydes with allylic bromides and tin(II) chloride dihydrate is largely accelerated by adding stoichiometric or substoichiometric amounts of sodium iodide. This method has some merits such as lower temperature, shorter reaction time and/or more choices of solvents for the reaction. Moreover, the activation by the iodide ion enables the use of relatively unreactive allylic chlorides of various structural types (e.g., 3-chloro-2-chloromethylpropene as an isobutene dianion equivalent) and, thus, expands synthetic applicability of this reaction. The major role of the iodide salt is attributed to the in situ generation of the corresponding allylic iodide.

  巴比尔型醛与烯丙基溴和二水合氯化亚锡的偶联反应通过添加化学计量或亚化学计量的碘化钠，得到了显著的加速。这种方法具有一些优点，如较低的反应温度、更短的反应时间以及/或更多选择性的溶剂使用。此外，碘离子引发的活化使得可以利用相对不活泼的各种结构类型的烯丙基氯化物（例如，作为异丁烯二负离子等价物的3-氯-2-氯甲基丙烯），从而扩大了这一反应的合成应用范围。碘盐的主要作用归因于其在位生成相应的烯丙基碘化物。
• Reactions of cyclopentadienylmetal-2-alkenyl carbonyl complexes with sulfur dioxide. Isolation and characterization of metal—η2-alkenesulfinate intermediates
  作者：R.L. Downs、A. Wojcicki

  DOI：10.1016/s0020-1693(00)87267-9

  日期：1978.1

  The isolation and characterization of the 2-alkene-S-sulfinato products of the reactions of transition metal-2-alkenyl complexes η5-C5H5M(CO)xCH2C(R)CR′R″ (M = Fe and x = 2, M = Mo and x = 3, M = W and x = 3; R = R′ = R″ = H, R = R′ = H and R″ = CH3, R = H and R′ = R″ = CH3, R = R′ = H and R″ = C6H3, R = CH3 and R′ = R″ = H, and/or R = R′ = H and R″ = Cl) with SO2 under a variety of conditions are

  过渡金属-2-烯基配合物η5-C5H5M（CO）xCH2C（R）CR'R''（M = Fe and x = 2，M = Mo and x = 3，M = W and x = 3; R = R′= R''= H，R = R′= H且R''= CH3，R = H且R′= R''= CH3，R描述了在各种条件下用SO 2 ＝ R′＝ H且R″ ＝ C 6 H 3，R ＝ CH 3且R′＝ R″ ＝ H，和/或R ＝ R′＝ H且R″ ＝ Cl）。包含1,3重排的MS（O）2C（R'）（R''）C（R）CH2和/或未重排的MS（O）2CH2C（R）CR'R''烯丙基片段的产物是由不对称的2-烯基配合物获得。另外，某些金属2-烯烃-S-亚磺酸盐表现出与烯丙基CC键有关的顺-反异构现象。通过使用M = Fe而不是M = Mo或低温纯净的SO2可以促进重排S-磺胺基异构体的形成，此外，随着取代基
• PROCESSES FOR PREPARING 1,1,2,3-TETRACHLOROPROPENE
  申请人：Merkel Daniel C.

  公开号：US20090030249A1

  公开（公告）日：2009-01-29

  Provided is a continuous process for preparing 1,1,2,3-tetrachloro-1-propene having the steps of catalytically dehydrochlorinating CH 2 ClCCl 2 CH 2 Cl in the gas phase to produce CHCl═CClCH 2 Cl; chlorinating the CHCl═CClCH 2 Cl to form CHCl 2 CCl 2 CH 2 Cl; and catalytically dehydrochlorinating the CHCl 2 CCl 2 CH 2 Cl in the gas phase to form CCl 2 ═CClCH 2 Cl.

  提供了一种制备1,1,2,3-四氯-1-丙烯的连续过程，包括以下步骤：在气相中催化脱氯化CH2ClCCl2CH2Cl，产生CHCl═CClCH2Cl；将CHCl═CClCH2Cl氯化成CHCl2CCl2CH2Cl；在气相中催化脱氯化CHCl2CCl2CH2Cl，形成CCl2═CClCH2Cl。
• [EN] PROCESS FOR THE PRODUCTION OF CHLORINATED PROPENES<br/>[FR] PROCÉDÉ DE PRODUCTION DE PROPÈNES CHLORÉS
  申请人：DOW GLOBAL TECHNOLOGIES LLC

  公开号：WO2014100066A1

  公开（公告）日：2014-06-26

  Processes for the production of chlorinated propenes are provided. The processes make use of 1,2-dichloropropane as a starting material and subject a feedstream comprising the same to an ionic chlorination process. At least a portion of any tri- and tetrachlorinated propanes not amenable to ionic chlorination conditions are removed from the ionic chlorination product stream, or, are subjected to chemical base dehydrochlorination step. In this way, recycle of intermediates not amenable to ionic chlorination reactions is reduced or avoided, as is the buildup of these intermediates within the process. Selectivity and, in some embodiments, yield of the process is thus enhanced.

  提供了制备氯代丙烯的工艺。该工艺利用1,2-二氯丙烷作为起始物质，并将含有1,2-二氯丙烷的进料流经过离子氯化过程。对于任何不能适应离子氯化条件的三氯丙烷和四氯丙烷的部分至少从离子氯化产物流中移除，或者经过化学碱脱氢氯化步骤。通过这种方式，既减少或避免了不适应离子氯化反应的中间体的回收，也避免了这些中间体在过程中的积聚。因此，该工艺的选择性和在某些实施例中产量得到了增强。
• [EN] PROCESS FOR THE PRODUCTION OF CHLORINATED PROPANES AND/OR PROPENES<br/>[FR] PROCÉDÉ POUR LA PRODUCTION DE PROPANES ET/OU DE PROPÈNES CHLORÉS
  申请人：DOW GLOBAL TECHNOLOGIES LLC

  公开号：WO2013074414A1

  公开（公告）日：2013-05-23

  Processes for the production of chlorinated propenes are provided wherein the feedstream comprises 1,2-dichlropropane. The present processes make use of at least one reactor twice, i.e., at least two reactions occur in the same reactor. Cost and time savings are thus provided. Additional savings can be achieved by conducting more than two chlorination reactions, or all chlorination reactions, in one chlorination reactor, and/or by conducting more than two dehydrochlorination reactions, or all dehydrochlorination reactions, within a single dehydrochlorination reactor.

  本发明提供了生产氯代丙烯的工艺，其中进料流包括1,2-二氯丙烷。本工艺利用至少一个反应器进行两次反应，即至少有两个反应在同一反应器中发生。因此，提供了节省成本和时间的优势。通过在一个氯化反应器中进行两个或所有氯化反应，并在一个脱氯反应器中进行两个或所有脱氯反应，可以实现额外的节省。

表征谱图