2,6-吡啶二羧酸二丁酯 | 41727-17-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2,6-吡啶二羧酸二丁酯
• 英文名称: dibutyl pyridine-2,6-dicarboxylate
• CAS: 41727-17-7
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: SJGUKBIVRJZPJZ-UHFFFAOYSA-N

物化性质

• 熔点：
  66-68 °C(lit.)
• 沸点：
  168-170 °C(Press: 1 Torr)
• 密度：
  1.084±0.06 g/cm3(Predicted)
• 保留指数：
  2068

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933399090

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Dibutyl 2,6-Pyridinedicarboxylate
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.

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SECTION 2: Hazards identification
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
This substance is not classified as dangerous according to Directive 67/548/EEC.
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.

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SECTION 3: Composition/information on ingredients
Substances
Molecular weight : 279,33 g/mol
No components need to be disclosed according to the applicable regulations.

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SECTION 4: First aid measures
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
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.
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

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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
Nature of decomposition products not known.
Advice for firefighters
Wear self-contained breathing apparatus for firefighting if necessary.
Further information
No data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapours, mist or gas.
For personal protection see section 8.
Environmental precautions
No special environmental precautions required.
Methods and materials for containment and cleaning up
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
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 Solids
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
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
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
No special environmental precautions required.

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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

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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

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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 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.

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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
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

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
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

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,6-吡啶二羧酸二丁酯 在 sodium tetrahydroborate 、 silica gel 、 1H-苯并咪唑-2-硫醇 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 57.58h， 生成
  参考文献：
  名称：

  Synthesis, spectroscopic characterization and density functional studies of a bis-benzimidazole derivative and of its complexes with palladium(II) halides

  摘要：

  摘要 2,6-bis(苯并咪唑-2'-基硫甲基)吡啶（L）配体及其钯(II)络合物[Pd(L)X]X（X = Cl, Br, 和 I）已被合成并通过光谱数据进行表征。该配体（L）通过常规加热以及微波辐射法制备。微波辐射法显示出额外特点，包括易于处理，反应速度更快且产率更高。摩尔电导率数据表明，络合物在DMSO中形成1:1电解质。通过量子化学计算阐明了(L)及其络合物的几何结构、基态能量和振动光谱。在单核络合物中，钯原子与三个氮原子和一个末端卤素原子以略微扭曲的平面方形排列配位。当前的元素分析、FT-IR（中红外和远红外）、1H和13C NMR光谱与Pd离子周围的平面方形几何形状一致。通过热重和差热分析评估了络合物的热行为。

  DOI：

  10.1016/j.crci.2013.10.016
• 作为产物：
  描述：

  吡啶-2.6-二羧酸二甲酯 、 正丁醇 在 Zn₄(OCOCF₃)6O 作用下， 以 异丙醚 为溶剂， 反应 40.0h， 以99%的产率得到2,6-吡啶二羧酸二丁酯
  参考文献：
  名称：

  四核锌簇催化轻度条件下各种甲基酯的酯交换反应

  摘要：

  开发了由四核锌簇促进的新的催化酯交换反应。温和的反应条件使各种功能化底物的反应能够以良好或高收率进行。在无溶剂条件下的大规模反应以低E因子值（0.66）进行，表明本催化剂具有很高的环境和经济优势。

  DOI：

  10.1021/jo800625v

文献信息

• A convenient synthetic route to polypyridine-esters by palladium-promoted carboalkoxylation
  作者：Abdelkrim El-ghayoury、Raymond Ziessel

  DOI：10.1016/s0040-4039(98)00820-x

  日期：1998.6

  smoothly with CO (1 atm) and n-butanol in the presence of a tertiary amine and a catalytic amount of bis(triphenylphosphine)palladium dichloride to afford the corresponding esters. When ethanol and a disubstituted substrate are used under milder conditions, selective mono-carboalkoxylation occurs. Amidation is effected using a primary amine as nucleophile.

  在叔胺和催化量的二氯化三（三苯基膦）钯的存在下，带有卤化物或三氟甲磺酸酯基团的吡啶和低聚吡啶与CO（1 atm）和正丁醇平稳反应，得到相应的酯。当在较温和的条件下使用乙醇和二取代的底物时，会发生选择性的单碳烷氧基化。使用伯胺作为亲核试剂进行酰胺化。
• Facile Synthesis of Polypyridine Esters:  A Route to Functionalized Aldehydes
  作者：Abdelkrim El-ghayoury、Raymond Ziessel

  DOI：10.1021/jo000635g

  日期：2000.11.1

  synthesized and fully characterized. The principal reaction involves the palladium(0)-catalyzed carboalkoxylation of the bromo-, chloro- or triflate-substituted pyridine unit with carbon monoxide in the presence of a primary alcohol as nucleophile and a tertiary amine as base. Monofunctionalization of disubstituted compounds is realized by reaction in ethanol under mild conditions (70 degrees C, 1 atm

  基于吡啶，1,8-萘啶，1,10-菲咯啉，2,2'-联吡啶和2,2'：6'，6''-叔吡啶单元的各种酯取代的低聚吡啶综合和充分表征。主要反应涉及在伯醇为亲核试剂和叔胺为碱的情况下，用一氧化碳对溴，氯或三氟甲磺酸取代的吡啶单元进行钯（0）催化的碳烷氧基化。通过在温和的条件下（70摄氏度，1个大气压的二氧化碳）在乙醇中反应，可以实现双取代化合物的单官能化。用硼氢化钠逐步还原选择的酯，然后进行Swern氧化，以良好的收率得到相应的甲醛。首次报道了几种产品。本文报道的合成方法代表了大规模制备酯官能化的低聚吡啶的有价值的方法，其随后可转化为相应的醇或酸。这些程序也为合理设计带有不同功能的配体提供了一种实用的方法。
• Palladium-Catalyzed Butoxycarbonylation of Polybromo(hetero)arenes: A Practical Method for the Preparation of (Hetero)arenepolycarboxylates and -carboxylic Acids
  作者：Baoming Ji、Weilong Wu、Yongkang Jing、Deyi Zhang、Xianghe Yan、Rong Liang、Zhiqiang Lu

  DOI：10.1055/a-1587-8859

  日期：2022.1

  The palladium-catalyzed alkoxycarbonylation of polybromo­(hetero)arenes was investigated systematically. The results show that cheap and readily available in situ Pd(OAc)2/rac-BINAP catalyst can catalyze the butoxycarbonylation of various polybromo(hetero)arenes efficiently, and gave (hetero)arenepolycarboxylates with moderate to high yield (59–94%). Using this method, two new compounds, 4,4′-bis(butoxycarbonyl)-1

  系统地研究了钯催化的多溴（杂）芳烃的烷氧基羰基化反应。结果表明，廉价且易于获得的原位 Pd(OAc)2/rac-BINAP 催化剂可以有效地催化各种多溴（杂）芳烃的丁氧基羰基化，并以中等至高产率（59-94%）得到（杂）芳烃聚羧酸盐。 . 使用这种方法，报告了两种新化合物 4,4'-双（丁氧基羰基）-1,1'-双-2-萘酚和 [2,2'-联嘧啶]-5,5'-二羧酸二丁酯，用于第一次。此外，通过丁氧基羰基化和水解成功地进行了克级规模的羧酸盐和羧酸的制备。这显示了 Pd(OAc)2/rac-BINAP 催化体系的广泛底物和实际应用。而且，
• The Preparation of Pyridine-carboxylates from Chloropyridines by the Palladium-catalyzed Alkoxycarbonylation
  作者：Yves Bessard、Roger Crettaz

  DOI：10.3987/com-99-8622

  日期：——

  The preparation of pyridinecarboxylates and pyridinedicarboxylates by alkoxycarbonylation of chloropyridines with carbon monoxide in the presence of palladium acetate and 1,1'-bis(diphenylphosphino)ferrocene is described. The process uses readily available starting materials and affords pyridinecarboxylates in good to very good yields.
• PLESHAKOV, M. G.;LYAN, P. M.;SNEGOTSKIJ, V. I.;PILIPENKO, V. S., TEZ. DOKL. BCEC. NAUCH.-TEXN. KONF. OXRANA OKRUZH. SREDY HA PREDPRIYATIYA+
  作者：PLESHAKOV, M. G.、LYAN, P. M.、SNEGOTSKIJ, V. I.、PILIPENKO, V. S.

  DOI：——

  日期：——