2-氨基-4-氯-3-氰基-5-甲酰基噻吩 | 104366-23-6

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 2-氨基-4-氯-3-氰基-5-甲酰基噻吩
• 中文别名: 2-氨基-4-氯-5-甲酰基噻吩-3-甲腈；2-氨基-3-氰基-4-氯-5-甲醛基噻吩；2-氨基-3-氰基-4-氯噻吩-5-甲醛；2-氨基-3-氰基-4-氯-5-甲酰基噻吩
• 英文名称: 2-amino-4-chloro-5-formylthiophene-3-carbonitrile
• 英文别名: 2-amino-3-cyano-4-chloro-5-formylthiophene；2-amino-4-chloro-3-cyano-5-formylthiophene；2-amino-4-chloro-5-formyl-3-cyanothiophene
• CAS: 104366-23-6
• 化学式: C₆H₃ClN₂OS
• mdl: MFCD03788265
• 分子量: 186.622
• InChiKey: XIZSUYSWKGAOCN-UHFFFAOYSA-N

物化性质

• 熔点：
  270-271°C
• 沸点：
  366.3±42.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  8/6.1
• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R43,R34,R22
• WGK Germany：
  3
• 海关编码：
  2934999090
• 危险品运输编号：
  UN 2923 6.1(8) / PGIII
• 包装等级：
  III
• 危险类别：
  8/6.1
• 危险性防范说明：
  P280,P301+P310,P305+P351+P338,P310
• 危险性描述：
  H301,H314,H317

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 2-Amino-4-chloro-5-formyl-3-thiophenecarbonitrile
CAS-No. : 104366-23-6
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Acute toxicity, Oral (Category 3)
Skin corrosion (Category 1B)
Skin sensitization (Category 1)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Harmful if swallowed. May cause sensitization by skin contact. Causes burns.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Danger
Hazard statement(s)
H301 Toxic if swallowed.
H314 Causes severe skin burns and eye damage.
H317 May cause an allergic skin reaction.
Precautionary statement(s)
P280 Wear protective gloves/ protective clothing/ eye protection/ face
protection.
P301 + P310 IF SWALLOWED: Immediately call a POISON CENTER or doctor/
physician.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
P310 Immediately call a POISON CENTER or doctor/ physician.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R22 Harmful if swallowed.
R43 May cause sensitization by skin contact.
R34 Causes burns.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36/37/39 Wear suitable protective clothing, gloves and eye/face protection.
S45 In case of accident or if you feel unwell, seek medical advice immediately
(show the label where possible).
Other hazards
Lachrymator.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : 2-Amino-3-cyano-4-chlorothiophene-5-carboxaldehyde
Formula : C6H3ClN2OS
Molecular Weight : 186,62 g/mol
Component Concentration
2-Amino-4-chloro-5-formyl-3-thiophenecarbonitrile
CAS-No. 104366-23-6 -

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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
Take off contaminated clothing and shoes immediately. Wash off with soap and plenty of water. Take
victim immediately to hospital. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Do NOT induce vomiting. 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
Cough, Shortness of breath, Headache, Nausea, Vomiting
Indication of any immediate medical attention and special treatment needed
no data available

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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
Carbon oxides, nitrogen oxides (NOx), Sulphur oxides, Hydrogen chloride gas
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Wear respiratory protection. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate
ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
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.

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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.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: 2 - 8 °C
Light sensitive. Heat sensitive. Stench.
Specific end uses
no data available

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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 N100 (US) or type P3 (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).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour Stench.
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 270 - 271 °C
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) Autoignition 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

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Oxidizing agents, acids
Hazardous decomposition products
Other decomposition products - no data available

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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 sensitization
May cause allergic skin reaction.
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
Potential health effects
Inhalation
May be harmful if inhaled. Material is extremely destructive to the tissue of
the mucous membranes and upper respiratory tract.
Ingestion Toxic if swallowed. Causes burns.
Skin May be harmful if absorbed through skin. Causes skin burns.
Eyes
Causes eye burns.
Signs and Symptoms of Exposure
Cough, Shortness of breath, Headache, Nausea, Vomiting
Additional Information
RTECS: Not available

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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
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material. 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.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: 2923 IMDG: 2923 IATA: 2923
UN proper shipping name
ADR/RID: CORROSIVE SOLID, TOXIC, N.O.S. (2-Amino-4-chloro-5-formyl-3-thiophenecarbonitrile)
IMDG: CORROSIVE SOLID, TOXIC, N.O.S. (2-Amino-4-chloro-5-formyl-3-thiophenecarbonitrile)
IATA: Corrosive solid, toxic, n.o.s. (2-Amino-4-chloro-5-formyl-3-thiophenecarbonitrile)
Transport hazard class(es)
ADR/RID: 8 (6.1) IMDG: 8 (6.1) IATA: 8 (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

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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
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 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.

反应信息

• 作为反应物：
  描述：

  2-氨基-4-氯-3-氰基-5-甲酰基噻吩 在 亚硝酸特丁酯 作用下， 以 DMF (N,N-dimethyl-formamide) 、 乙腈 为溶剂， 以68%的产率得到5-formyl-4-chlorothiophene-3-carbonitrile
  参考文献：
  名称：

  Thrombin inhibitors

  摘要：

  新型五元杂环胺基化物，其制备和用作胰蛋白酶样丝氨酸蛋白酶的竞争性抑制剂，特别是血栓素和激肽原酶如激肽原酶的抑制剂。含有这些化合物作为活性成分的药物组合物，以及将这些化合物用作血栓素抑制剂、抗凝剂和抗炎药剂。

  公开号：

  US06740647B1
• 作为产物：
  描述：

  N,N-dimethyl-N'-(4-chloro-3-cyano-5-formylthien-2-yl)-formamidine 在 甲酸 作用下， 以 水 为溶剂， 生成 2-氨基-4-氯-3-氰基-5-甲酰基噻吩
  参考文献：
  名称：

  Thiophene derivatives

  摘要：

  通式I的新化合物##STR1##，其中X是氟、氯、溴、SO.sub.2 Y或未取代或取代的羟基或巯基，Y是烷基、烯烃基、环烷基、芳基烷基、芳基、氯或未取代或取代的羟基或氨基，R是氢、C.sub.1 -C.sub.4-烷基或通过亲电取代引入的基团或--CH.dbd.T的公式的基团，其中T是甲烯活性化合物或胺的基团，R.sup.1是氢、酰基或未取代或取代的烷基、环烷基或烯烃基，R.sup.2是氢或未取代或取代的烷基或烯烃基，或R.sup.1和R.sup.2与氮一起形成饱和杂环结构，R.sup.1和R.sup.2一起形成##STR2##的基团，根据其结构，这些化合物可用作重氮化合物和/或偶联组分，或一般作为染料中间体。

  公开号：

  US05206375A1

文献信息

• pH-induced azo-keto and azo-enol tautomerism for 6-(3-methoxypropylamino)pyridin-2-one based thiophene azo dyes
  作者：Xiao-Lei Zhao、Jiao Geng、Hui-Fen Qian、Wei Huang

  DOI：10.1016/j.dyepig.2017.08.020

  日期：2017.12

  post-modification (PM) is proposed to prepare two new types of 2-amino-3-cyano-4-chloro-5-formylthiophene based heterocyclic azo dyes with mono and double 3-methoxypropan-1-amine substituted pyridine components, where the terminal aldehyde radical of the 2-formylthiophene moiety is extended into imine, acetal or α,β-unsaturated cyanoacetic ester group. The evaluation of pH stability of the mono FGT products indicates

  提出了结合官能团转化（FGT）和后修饰（PM）的合成策略，以制备两种新型的基于单氨基和双基3的2-氨基-3-氰基-4-氯-5-甲酰基噻吩基的杂环偶氮染料。 -甲氧基丙-1-胺取代的吡啶组分，其中2-甲酰基噻吩部分的末端醛基扩展成亚胺，乙缩醛或α，β-不饱和氰基乙酸酯基。对单FGT产品的pH稳定性进行评估表明，基本稳定性取决于π通过比较我们合成的噻吩和偶氮苯基染料得到的重氮共轭体系，其中更好的电子离域可促进质子在分子内的转移，导致对碱的稳定性差。此外，环内偶氮酮⇌建议在偶合组分中使用偶氮-烯醇互变异构现象，以解释pH滴定实验中五个等吸收点的出现。相反，无论使用何种重氮组分，所有基于N 2，N 6-双（3-甲氧基丙基）吡啶-2,6-二胺的偶氮染料均具有极高的pH稳定性，因为在两次加成后均不存在质子接受位点。 FGT。还发现，合成的噻吩杂环染料在PM之后表现出大的色域。例如，最大吸收波长（λ最大
• [EN] DISPERSE DYES<br/>[FR] COLORANTS DE DISPERSION
  申请人：CLARIANT INT LTD

  公开号：WO2005056690A1

  公开（公告）日：2005-06-23

  Disperse dyes of the general formula (I) where D is a diazo component derived from a substituted or unsubstituted aromatic amine, K is an aromatic radical of the formula (K1), (K2) oder (K3) and the substituents are each as defined in the first claim. Further described are the preparation and the use of the dyes according to the invention.

  一般公式（I）的分散染料，其中D是由取代或未取代的芳香胺衍生的重氮组分，K是公式（K1）、（K2）或（K3）的芳香基团，且取代基如第一权利要求中所定义。进一步描述了根据本发明的染料的制备和使用。
• pH-controlled synthesis of an aromatic triazene and its copper(II) complexation accompanied by an unexpected aromatic ring halogenation
  作者：Dan Xu、Jiao Geng、Yuan Dai、Yu-Xin Peng、Hui-Fen Qian、Wei Huang

  DOI：10.1016/j.dyepig.2016.08.062

  日期：2017.1

  were synthesized from the reaction between 2-amino-3-cyano-4-chloro-5-formylthiophene and 2-amino-5-nitrophenol under different pH values. Two Cu(II) complexes of the triazene H2L formulated as [Cu(L′)(H2O)2]·DMF}n (C1) and [Cu2L2(DMF)2] (C2) were obtained by means of the reactions between deprotonated triazene ligand L2− and different copper salts (CuCl2·2H2O and Cu(OAc)2·H2O) at room temperature. It

  在不同的pH值下，由2-氨基-3-氰基-4-氯-5-甲酰基噻吩与2-氨基-5-硝基苯酚之间的反应合成了三氮烯异构体（H 2 L）和偶氮染料（D1）。配制成[Cu（L'）（H 2 O）2 ]·DMF} n（C1）和[Cu 2 L 2（DMF）2 ]（C2）的三氮烯H 2 L的两个Cu（II）配合物为通过去质子化的三氮烯配体L 2−与不同的铜盐（CuCl 2 ·2H 2 O和Cu（OAc）2 ·H 2O）在室温下。应当指出，通过不寻常的Cu（II）介导的L 2-的苯基卤化获得了新的原位形成的氯化配体L' 2-，其通过以78％的高产率形成一维配位聚合物C1来证明。使用Cu（OAc）2 ·H 2 O作为金属源的对照实验表明，形成了配体L 2-的双核Cu（II）络合物C2，而没有发生芳环卤化。建议当前的研究可以提出一种在温和的实验条件下以高收率实现芳族卤代的有效方法。
• <i>cis</i> alkenes stabilized by intramolecular sulphur⋯π interactions
  作者：Xiaolei Zhao、Wei Zheng、Yi Zhang、Wei Huang

  DOI：10.1039/c9cc08558k

  日期：——

  A series of alkenes with bistable isomers were obtained containing a thiophene/azoheteroaryl backbone. Visible light and heat-induced reversible cis ⇌ trans isomerizations were evidenced by UV-Vis and 1H NMR spectra. The stabilization of cis alkenes was attributed to intramolecular sulphurπ (Sπ) interactions, which were further supported by theoretical calculations.

  获得了具有噻吩/偶氮杂芳基骨架的一系列具有双稳态异构体的烯烃。UV-Vis和1H NMR光谱证明可见光和热诱导的可逆顺式反式异构化。顺式烯烃的稳定归因于分子内硫（Sπ）相互作用，这在理论计算中得到了进一步支持。
• Pyridone based binary and ternary monomethine dyes derived from 2-amino-4-chloro-5-formylthiophene-3-carbonitrile
  作者：Xiao-Lei Zhao、Jiao Geng、Bin Hu、Dan Xu、Wei Huang

  DOI：10.1016/j.dyepig.2018.03.014

  日期：2018.8

  ophene based heterocyclic hydrazone/azo dyes. UV−Vis spectral analyses reveal that the synthesized heterocyclic dyes exhibit a large color gamut because of the extension of the conjugation length of the chromophore, where the maximum absorption wavelength (λmax) is significantly red-shifted up to 181 nm from binary monomethine to ternary monomethine-azo dyes.

  已经通过一种简单高效的乙酸酐方法制备了新的单次甲基染料，其中常用的吡啶2,6-二酮部分和噻吩衍生物占据了次甲基单元的每一侧。其中，为了进一步调节2-氨基-3-氰基-4-氯-5-的π共轭体系和电子光谱，首先通过特别有用的后修饰合成策略获得了三元甲硫氨酸偶氮染料。基于甲酰基噻吩的杂环/偶氮染料。紫外-可见光谱分析表明，所合成的杂环染料表现出由于延长发色团的共轭长度的，其中，最大吸收波长的大的色域（λ最大）从二元一甲胺到三元一甲胺偶氮染料显着红移至181 nm。