2-氯丙烯基异硫氰酸酯 | 14214-31-4

• 物质功能分类: 化学农药原药 - 杀虫剂中间体
• 分子结构分类: 有机化合物 - 有机硫化合物 - 异硫氰酸盐
• 中文名称: 2-氯丙烯基异硫氰酸酯
• 英文名称: 1-isothiocyanato-2-chloro-2-propene
• 英文别名: 2-chloroallyl isothiocyanate；2-chloropropenyl isothiocyanate；2-chloro-3-isothiocyano-1-propene；2-chloro-3-isothiocyanato-1-propene；2-chloro-3-isothiocyanatoprop-1-ene
• CAS: 14214-31-4
• 化学式: C₄H₄ClNS
• mdl: MFCD01716868
• 分子量: 133.601
• InChiKey: DGBFPSVUFUDQNA-UHFFFAOYSA-N

物化性质

• 沸点：
  182°C
• 密度：
  1.2700

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  T
• 安全说明：
  S45
• 危险类别码：
  R25
• 海关编码：
  2930909090
• 储存条件：
  2-8°C

SDS

---

SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 2-Chloro-3-Isothiocyanatopropene
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

---

SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Acute toxicity, Oral (Category 3), H301
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
T Toxic R25
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Danger
Hazard statement(s)
H301 Toxic if swallowed.
Precautionary statement(s)
P301 + P310 IF SWALLOWED: Immediately call a POISON CENTER or doctor/
physician.
Supplemental Hazard none
Statements
Other hazards
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.

---

SECTION 3: Composition/information on ingredients
Substances
Molecular weight : 133,6 g/mol
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
2-Chloro-3-Isothiocyanatopropene
Acute Tox. 3; H301 <= 100 %
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
2-Chloro-3-Isothiocyanatopropene
T, R25 <= 100 %
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

---

SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Take victim immediately to hospital. Consult a physician.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
No data available

---

SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Nature of decomposition products not known.
Advice for firefighters
Wear self-contained breathing apparatus for firefighting if necessary.
Further information
No data available

---

SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Wear respiratory protection. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
For personal protection see section 8.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

---

SECTION 7: Handling and storage
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Storage class (TRGS 510): Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous
materials causing chronic effects
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

---

SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling
the product.
Personal protective equipment
Eye/face protection
Face shield and safety glasses Use equipment for eye protection tested and approved under
appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face particle
respirator type N99 (US) or type P2 (EN 143) respirator cartridges as a backup to engineering
controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use
respirators and components tested and approved under appropriate government standards such
as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.

---

SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour No data available
c) Odour Threshold No data available
d) pH No data available
e) Melting point/freezing No data available
point
f) Initial boiling point and No data available
boiling range
g) Flash point No data available
h) Evaporation rate No data available
i) Flammability (solid, gas) No data available
j) Upper/lower No data available
flammability or
explosive limits
k) Vapour pressure No data available
l) Vapour density No data available
m) Relative density No data available
n) Water solubility No data available
o) Partition coefficient: n- No data available
octanol/water
p) Auto-ignition No data available
temperature
q) Decomposition No data available
temperature
r) Viscosity No data available
s) Explosive properties No data available
t) Oxidizing properties No data available
Other safety information
No data available

---

SECTION 10: Stability and reactivity
Reactivity
No data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
No data available
Conditions to avoid
No data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
In the event of fire: see section 5

---

SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
No data available
Skin corrosion/irritation
No data available
Serious eye damage/eye irritation
No data available
Respiratory or skin sensitisation
No data available
Germ cell mutagenicity
No data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
No data available
Specific target organ toxicity - single exposure
No data available
Specific target organ toxicity - repeated exposure
No data available
Aspiration hazard
No data available
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

---

SECTION 12: Ecological information
Toxicity
No data available
Persistence and degradability
No data available
Bioaccumulative potential
No data available
Mobility in soil
No data available
Results of PBT and vPvB assessment
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.
Other adverse effects
No data available

---

SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

---

SECTION 14: Transport information
UN number
ADR/RID: 2811 IMDG: 2811 IATA: 2811
UN proper shipping name
ADR/RID: TOXIC SOLID, ORGANIC, N.O.S. (2-Chloro-3-Isothiocyanatopropene)
IMDG: TOXIC SOLID, ORGANIC, N.O.S. (2-Chloro-3-Isothiocyanatopropene)
IATA: Toxic solid, organic, n.o.s. (2-Chloro-3-Isothiocyanatopropene)
Transport hazard class(es)
ADR/RID: 6.1 IMDG: 6.1 IATA: 6.1
Packaging group
ADR/RID: III IMDG: III IATA: III
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
No data available

---

SECTION 15: Regulatory information
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
No data available
Chemical Safety Assessment
For this product a chemical safety assessment was not carried out

---

SECTION 16: Other information
Full text of H-Statements referred to under sections 2 and 3.
Acute Tox. Acute toxicity
H301 Toxic if swallowed.
Full text of R-phrases referred to under sections 2 and 3
T Toxic
R25 Toxic if swallowed.
Further information
Copyright 2014 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

化学性质
本品为无色液体，沸点73～76℃/2.4kPa，不溶于水，能溶解于有机溶剂。

用途
2-氯丙烯基异硫氰酸酯是杀虫剂噻虫嗪、噻虫胺的中间体。

生产方法
其制备方法是在反应釜中加入乙腈、2,3-二氯丙烯和硫氰化钠，在催化剂的作用下加热回流3.5小时。反应结束后，过滤除去不溶物，浓缩滤液后加入二氯甲烷再次过滤，再浓缩剩余物，并在140℃油浴中加热1小时，减压蒸馏得产品。反应方程式如下：
CH₂=CHClCH₂Cl + NaSCN → CH₂=CHClCH₂NCS

反应信息

• 作为反应物：
  描述：

  2-氯丙烯基异硫氰酸酯 在 氨 作用下， 生成 (2-chloro-allyl)-thiourea
  参考文献：
  名称：

  Henry, Chemische Berichte, 1872, vol. 5, p. 188

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-二氯丙烯 以 水 为溶剂， 生成 2-氯丙烯基异硫氰酸酯
  参考文献：
  名称：

  Process for producing isothiocyanate derivatives

  摘要：

  本发明公开了一种用于生产2-卤代烯丙基异硫氰酸酯的方法，其化学式表示为：##STR1## 其中X1是卤素原子。该方法包括在加热的水存在下，将化合物与硫氰酸盐反应。所述化合物的化学式表示为：##STR2## 其中X1是卤素原子，X2是一个离去基团。所述硫氰酸盐的化学式表示为M(SCN)n，其中M是金属或铵基团，n是M的价数。根据本发明的生产方法，2-卤代烯丙基异硫氰酸酯\x9bI!可在工业上大规模生产，产率高，其具有杀虫效果，可用作药物、农药等中间体。

  公开号：

  US05726338A1

文献信息

• Process for the preparation of chlorothiazole derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05180833A1

  公开（公告）日：1993-01-19

  Novel processes for preparing 2-chlorothiazoles, useful as an intermediate for insecticides, from allyl isothiocyanate derivatives having the formula [II]: ##STR1## wherein X represents a leaving group, are simple and convenient reaction procedures under mild conditions without need of a large excess of a chlorinating agent. Further, processes for preparing 5-(aminomethyl)-2-chlorothiazole or salts thereof from the compound [II] achieve higher yields by simple, convenient and inexpensive procedures.

  制备2-氯噻唑的新方法，该化合物作为杀虫剂中间体具有用途，其原料为烯丙基异硫氰酸酯衍生物，具有式[II]的结构：##STR1##其中X代表离去基团。这些方法在温和条件下进行，操作简便，无需大量过量的氯化剂。此外，从化合物[II]出发制备5-(氨基甲基)-2-氯噻唑或其盐的方法，通过简单、便捷且成本低廉的步骤，实现了更高的产率。
• Synthesis and Herbicidal Activity of 2-Cyano-3-(2-chlorothiazol-5-yl)methylaminoacrylates
  作者：Qingmin Wang、Heng Li、Yonghong Li、Runqiu Huang

  DOI：10.1021/jf035312a

  日期：2004.4.1

  series of 2-cyano-3-(2-chlorothiazol-5-yl)methylaminoacrylates were synthesized as herbicidal inhibitors of PSII electron transport. All of these compounds exhibited good herbicidal activities. In particular, (Z)-ethoxyethyl 2-cyano-3-isopropyl-3-(2-chlorothiazol-5-yl)methylaminoacrylate showed excellent herbicidal activities even at a dose of 75 g/ha. A suitable group at the 3-position of acrylate was essential

  合成了一系列2-氰基-3-（2-氯噻唑-5-基）甲基氨基丙烯酸酯作为PSII电子传递的除草抑制剂。所有这些化合物均表现出良好的除草活性。特别地，即使在75g / ha的剂量下，（Z）-乙氧基乙基2-氰基-3-异丙基-3-（2-氯噻唑-5-基）甲基氨基丙烯酸酯也显示出优异的除草活性。丙烯酸酯的3-位的合适基团对于高除草活性是必不可少的。含有2-氯-5-噻唑基的2-氰基丙烯酸酯是一类新型的除草剂，其除草活性与具有氯吡啶基或氯苯基的现有类似物相当。
• 噻虫嗪生产方法及萃取剂
  申请人：邯郸市瑞田农药有限公司

  公开号：CN110981866B

  公开（公告）日：2022-08-12

  本发明提供噻虫嗪生产方法及萃取剂，属于农药技术领域，具体提供一种以以乙二醇水杨酸酯作为络合剂的萃取剂；还提供一种复合萃取剂，该萃取剂包括络合剂和稀释剂，该络合剂包括乙二醇水杨酸酯和P204，其中，乙二醇水杨酸酯和P204的萃合比为1:1.5‑1:2。本发明提供的萃取剂以乙二醇水杨酸酯作为络合剂，能够与噻虫嗪的‑N‑发生较强的离子缔合，生成结构相同的离子萃合物，增加分配比；与P204复合萃取时，能够促进噻虫嗪的强吸电子基团硝基‑NO2与P204的‑OH发生氢键缔合，当乙二醇水杨酸酯和P204萃取剂在萃合比为1:1.5‑2时，能够协同增效分配比，提高萃取率。
• Process for the preparation of thiazole derivatives
  申请人：Syngenta Crop Protection, Inc.

  公开号：US06369233B1

  公开（公告）日：2002-04-09

  The Invention relates to a process for the preparation of a compound of the formula wherein Q, Y, Z, R1, R2, R3, R4 and R5 are as defined in the specification, which comprises a) reacting a compound of the formula  with a halogenating agent to form a compound of the formula b) converting a compound of formula (II) by means of a halogenating agent into a compound of the formula  optionally c) converting the compound of formula (IV) into a compound of formula (III); d) converting a compound of formula (III) by means of a compound of the formula e) converting a compound (IV) by means of a compound (V) into a compound (VI); and f) converting a compound (VI) by means of a chlorinating agent into a compound (I); a compound (IV); to a process for the preparation of a compound (III) and to a process for the preparation of a compound (IV).

  本发明涉及一种制备式中Q、Y、Z、R1、R2、R3、R4和R5如规范中所定义的化合物的方法，包括：a)将式(I)的化合物与卤化剂反应形成式(II)的化合物；b)通过卤化剂将式(II)的化合物转化为式(III)的化合物；可选c)将式(IV)的化合物转化为式(III)的化合物；d)通过式的化合物将式(III)的化合物转化为式(V)的化合物；e)通过式(V)的化合物将式(IV)的化合物转化为式(VI)的化合物；f)通过氯化剂将式(VI)的化合物转化为式(I)的化合物；以及制备化合物(III)和制备化合物(IV)的方法。
• 一种1-异硫氰酸基-2-氯-2-丙烯的合成方法
  申请人：岳阳景嘉化工有限公司

  公开号：CN108892630A

  公开（公告）日：2018-11-27

  本发明公开了一种1‑异硫氰酸基‑2‑氯‑2‑丙烯的合成方法，将可溶性硫氰酸盐、2，3‑二氯丙烯溶于有机溶剂中，加热，反应得到1‑异硫氰基‑2‑氯‑2‑丙烯。本发明工艺简单，反应路径短，成本低，收益高，摩尔收率＞99.5％(相对二氯丙烯)。工艺设计合理、过程安全可控，无废水工艺，省去处理污水的成本。

表征谱图