6,6′′-二溴-2,2′:6′,2′′-三联吡啶 | 100366-66-3

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 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: 6,6′′-二溴-2,2′:6′,2′′-三联吡啶
• 中文别名: 6,6’’-二溴-2,2’:6’,2’’-三联吡啶；6,6-二溴-2,2:6,2-三联吡啶
• 英文名称: 6,6-dibromo-2,2':6',2-terpyridine
• 英文别名: 6,6''-dibromoterpyridine；6,6″-dibromo-2,2′:6′,2″-terpyridine；6,6''-Dibromo-2,2':6',2''-terpyridine；2,6-bis(6-bromopyridin-2-yl)pyridine
• CAS: 100366-66-3
• 化学式: C₁₅H₉Br₂N₃
• 分子量: 391.065
• InChiKey: PYMBATDYUCQLBC-UHFFFAOYSA-N

物化性质

• 熔点：
  257-263 °C(lit.)
• 沸点：
  473.0±40.0 °C(Predicted)
• 密度：
  1.685±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，未有已知危险反应。应避免与强氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.67
• 氢给体数：
  0.0
• 氢受体数：
  3.0

安全信息

• WGK Germany：
  3
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险标志：
  GHS07
• 危险类别码：
  R36/37/38
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338
• 海关编码：
  2933399090

SDS

---

Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
: 6,6′′-Dibromo-2,2′:6′,2′′-terpyridine
Product name
CAS-No. : 100366-66-3

---

Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
Causes skin irritation.
Causes serious eye irritation.
May cause respiratory irritation.
Precautionary statement(s)
Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36 Wear suitable protective clothing.
Other hazards - none

---

Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C15H9Br2N3
Molecular Weight : 391,06 g/mol
Component Concentration
6,6''-Dibromo-2,2':6',2''-terpyridine
CAS-No. 100366-66-3 -

---

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. 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
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
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
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
Carbon oxides, nitrogen oxides (NOx), Hydrogen bromide gas
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

---

Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
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.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.
Specific end uses
no data available

---

Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 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.
Immersion protection
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: > 480 min
Splash protection
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: > 30 min
test method: EN374
If used in solution, or mixed with other substances, and under conditions which differ from EN 374,
contact the supplier of the CE approved gloves. This recommendation is advisory only and must
be evaluated by an Industrial Hygienist familiar with the specific situation of anticipated use by our
customers. It should not be construed as offering an approval for any specific use scenario.
Body Protection
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).

---

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 Melting point/range: 257 - 263 °C - lit.
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

---

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
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

---

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
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
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation
May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

---

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

---

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.

---

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

---

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
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

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  6,6′′-二溴-2,2′:6′,2′′-三联吡啶 在 copper(I) oxide 、 氨 作用下， 以 乙二醇 为溶剂， 反应 16.0h， 以50%的产率得到6,6″-diamino-2,2′,6′,2″-terpyridine
  参考文献：
  名称：

  迈向光催化烷烃氧化：将双氧插入铂（II）-甲基键中

  摘要：

  始终保持光明的一面：光驱使双氧插入铂-甲基键中会生成甲基过氧配合物（参见图片），它会分解为甲醛和铂羟基配合物。该反应在数分钟内在1 atm O 2和室温下发生，并通过单线态氧的形成进行。

  DOI：

  10.1002/anie.200806187
• 作为产物：
  描述：

  2-乙酰基-6-溴吡啶 在 乙酸铵 、 盐酸 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 5.0h， 生成 6,6′′-二溴-2,2′:6′,2′′-三联吡啶
  参考文献：
  名称：

  2,2'：6'，2''-叔吡啶大环的制备和配位化学。第5部分。含有2,2'：6'，2''-叔吡啶的未取代的十五元环大环

  摘要：

  描述了通过瞬时模板反应制备并入有2,2'：6'，2''-吡啶基部分的简单未取代的五齿大环化合物的方法。描述了配体的钴（II），镍（II），铜（II）和锌（II）配合物，以及这些化合物的氧化还原化学反应。Esr研究表明，形成了具有溶剂分子占据轴向位点的五边形-双锥体络合物。

  DOI：

  10.1039/dt9870000005
• 作为试剂：
  描述：

  2-环己烯-1-酮 、 5-溴-2-戊酮 、 三乙基氯硅烷 在 锰 、 氯化镍二甲氧基乙烷 、 6,6′′-二溴-2,2′:6′,2′′-三联吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以87%的产率得到5-(3-((tripropylsilyl)oxy)cyclohex-2-en-1-yl)pentan-2-one
  参考文献：
  名称：

  镍催化的伯烷基溴化物与烯类的还原共轭加成反应，形成甲硅烷基烯醇醚

  摘要：

  在烯酮上共轭添加有机金属试剂以形成甲硅烷基烯醇醚产物是使活化的烯烃双官能化的通用方法，但所需的有机金属试剂可能会受到限制。镍络合的邻溴化叔吡啶配体催化未受阻的伯烷基溴化物与烯酮和氯硅烷的还原性交亲电子偶联，形成甲硅烷基烯醇醚产物。该条件与多种环状/无环烯酮和官能团相容。

  DOI：

  10.1021/acs.orglett.6b03509

文献信息

• 6,6′-Dihydroxy terpyridine: a proton-responsive bifunctional ligand and its application in catalytic transfer hydrogenation of ketones
  作者：Cameron M. Moore、Nathaniel K. Szymczak

  DOI：10.1039/c2cc36927c

  日期：——

  The ligand 6,6′-dihydroxy terpyridine (dhtp) is presented as a bifunctional ligand capable of directing proton transfer events with metal-coordinated substrates. Solid-state analysis of a Ru(II)-dhtp complex reveals directed hydrogen-bonding interactions of the hydroxyl groups of dhtp with a Ru-bound chloride ligand. The utility of dhtp was demonstrated by chemoselective transfer hydrogenation of ketones.

  配体6,6'-二羟基三吡啶（dhtp）被介绍为一种双功能配体，能够指导与金属配位底物间的质子传递事件。对Ru(II)-dhtp配合物的固态分析揭示了dhtp羟基与Ru结合的氯配体之间的定向氢键相互作用。通过酮的选择性转移氢化反应，展示了dhtp的实用性。
• Synthesis of Some 2,2′:6′,2″-Terpyridines Disubstituted in Positions 6 and 6″ with Head-to-Tail Oriented Amino Acids and Dipeptides: A Simple Entry to a Reversible Inducer of Folding in Amino Acid Sequences
  作者：Rita Annunziata、Maurizio Benaglia、Alessandra Puglisi、Laura Raimondi、Franco Cozzi

  DOI：10.1002/ejoc.200800433

  日期：2008.8

  The 2,2′:6′,2″-terpyridine scaffold has been identified as a conformationally discrete structural element potentially capable of inducing reversible folding in substituents, attached through suitable spacers to its 6,6″-positions, by metal complexation/decomplexation or by protonation/deprotonation. The synthesis of some terpyridine–amino acids and terpyridine–dipeptide conjugates is described. The

  2,2':6',2"-三联吡啶支架已被鉴定为一种构象离散的结构元件，可能能够诱导取代基可逆折叠，通过合适的间隔物连接到其 6,6"-位置，通过金属络合/解络合或通过质子化/去质子化。描述了一些三联吡啶-氨基酸和三联吡啶-二肽缀合物的合成。这些缀合物的组装是通过将 NH2 和 CO2H 保护的甘氨酸、丙氨酸和缬氨酸残基或反向平行定向的 AlaGly/GlyAla 链通过苯乙炔间隔物连接到三联吡啶支架上来实现的。初步实验表明，将 Zn2+ 添加到氨基酸取代的 transoid 三联吡啶系统后，形成了折叠的 cisoid 复合物。还，二肽取代系统的双（质子化）导致折叠加合物的形成。折叠过程的可逆性通过用三乙胺去除 Zn2+ 或用氨水去质子化来证明。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Use of metal complex compounds as catalysts for oxidation using molecular oxygen or air
  申请人：Wieprecht Torsten

  公开号：US20060019853A1

  公开（公告）日：2006-01-26

  Use, as a catalyst for oxidation reactions using molecular oxygen and/or air, of at least one metal complex compound of formula (1) wherein Me is manganese, titanium, iron, cobalt, nickel or copper, X is a coordinating or bridging radical, n and m are each independently of the other an integer having a value of from 1 to 8, p is an integer having a value of from 0 to 32, z is the charge of the metal complex, Y is a counter-ion, q=z/(charge of Y), and L is a ligand of formula (2) wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are each independently of the others hydrogen; unsubstituted or substituted C 1 -C 18 alkyl or aryl; cyano; halogen; nitro; —COOR 12 or —SO 3 R 12 wherein R 12 is in each case hydrogen, a cation or unsubstituted or substituted C 1 -C 18 alkyl or aryl; —SR 13 , —SO 2 R 13 or —OR 13 wherein R 13 is in each case hydrogen or unsubstituted or substituted C 1 -C 18 alkyl or aryl; —NR 14 R 15 ; —(C 1 -C 6 alkylene)-NR 14 R 15 ; —N (+) R 14 R 15 R 16 ; —(C 1 -C 6 alkylene)-N (+) R 14 R 15 R 16 ; —N(R 13 )—(C 1 -C 6 alkylene)-NR 14 R 15 ; —N[(C 1 -C 6 alkylene)-NR 14 R 15 ] 2 ; —N(R 13 )—(C 1 -C 6 alkylene)-N (+) R 14 R 15 R 16 ; —N[(C 1 -C 6 alkylene)-N (+) R 14 R 15 R 16]2 ; —N(R 13 )—N—R 14 R 15 or —N(R 13 )N″R 14 R 15 R 16 , wherein R 13 is as defined above and R 14 , R 15 and R 16 are each independently of the other(s) hydrogen or unsubstituted or substituted C 1 -C 18 alkyl or aryl, or R 14 and R 15 , together with the nitrogen atom linking them, form an unsubstituted or substituted 5-, 6- or 7-membered ring which may contain further hetero atoms. [L n Me m X p ] z Y q (1)

  使用至少一种具有以下式（1）的金属配合物化合物作为氧化反应的催化剂，其中Me为锰、钛、铁、钴、镍或铜，X为配位或桥联基团，n和m分别独立地为1至8之间的整数，p为0至32之间的整数，z为金属配合物的电荷，Y为对离子，q=z/(Y的电荷)，L为具有以下式（2）的配体，其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10和R11各自独立地为氢；未取代或取代的C1-C18烷基或芳基；氰基；卤素；硝基；—COOR12或—SO3R12，其中R12在每种情况下为氢、阳离子或未取代或取代的C1-C18烷基或芳基；—SR13、—SO2R13或—OR13，其中R13在每种情况下为氢或未取代或取代的C1-C18烷基或芳基；—NR14R15；—(C1-C6烷基)-NR14R15；—N(+)R14R15R16；—(C1-C6烷基)-N(+)R14R15R16；—N(R13)—(C1-C6烷基)-NR14R15；—N[(C1-C6烷基)-NR14R15]2；—N(R13)—(C1-C6烷基)-N(+)R14R15R16；—N[(C1-C6烷基)-N(+)R14R15R16]2；—N(R13)—N—R14R15或—N(R13)N″R14R15R16，其中R13如上定义，R14、R15和R16各自独立地为氢或未取代或取代的C1-C18烷基或芳基，或R14和R15与连接它们的氮原子一起形成未取代或取代的5、6或7成员环，该环可能含有进一步的杂原子。[LnMemXp]zYq（1）
• Dinuclear Pd(II) and Pt(II) compounds bearing a bridging π-conjugated moiety: synthesis and reactivity toward alkynes and isocyanides
  作者：Young-Sung Han、Kang-Yeoun Jung、Yong-Joo Kim、Gang Min Lee、Soon W. Lee

  DOI：10.1080/00958972.2018.1508660

  日期：2018.10.18

  Abstract Dinuclear Pd(II) halides that contain bridging π-conjugated groups, trans,trans-[(PR3)2(X)Pd–Y–Pd(X)(PR3)2] (X = Br; YH2 = terpyridine, fluorenone, benzil, benzthiadiazole), were prepared by the oxidative addition of corresponding dihalo π-conjugated reagents to [Pd(styrene)(PR3)2]. Similar reactions involving dihalobenzil, dihalobithiophene, or dihaloterthiophene afforded dinuclear Pt(II) halides

  摘要 双核 Pd(II) 卤化物，包含桥接 π 共轭基团，trans,trans-[(PR3)2(X)Pd–Y–Pd(X)(PR3)2] (X = Br; YH2 = terpyridine, 芴酮通过将相应的二卤 π 共轭试剂氧化加成到 [Pd(苯乙烯)(PR3)2] 上制备。涉及二卤苯、二卤二噻吩或二卤三噻吩的类似反应提供了含有桥连 π 共轭基团的双核 Pt(II) 卤化物。此外，当二卤硅烷衍生物 2,5-dibromo-1,1-二甲基（或二苯基）-3,4-diphenylsilole}与[Pd(苯乙烯)(PR3)2]反应时，单核或双核Pd(II)配合物得到带有二甲基（或二苯基）-3,4-二苯基甲硅烷基团的化合物。双核联噻吩桥连的 Pd(II) 卤化物与 HC≡C–R R = SiPh3, 在 CuI 和 HNEt2 存在下，C(O)OMe} 导致意外形成 [Pd(C≡C–R)2(PR3)2]
• The Synthesis of Poly-Nitrile Aromatic and Oligopyridine Ligands Via Palladium-Catalyzed Cyanation of Aryl Halides
  作者：Kevin John、Jacqueline Veauthier、Christin Carlson、Gavin Collis、Jaqueline Kiplinger

  DOI：10.1055/s-2005-872113

  日期：——

  Modification of Beller's palladium-catalyzed cyanation procedure for simple aromatic halides leads to a versatile and rapid route to complex multi-nitrile aryl and oligopyridyl ligands that improves on known literature methods. By heating the reagents in the high boiling solvent mesitylene to reflux temperatures at ambient pressure, we have observed the conversion of halogenated precursors to the corresponding

  Beller 对简单芳族卤化物的钯催化氰化过程的改进导致了一种通用且快速的复杂多腈芳基和寡吡啶基配体的路线，该路线改进了已知的文献方法。通过在环境压力下将高沸点溶剂均三甲苯中的试剂加热至回流温度，我们观察到卤代前体转化为相应的腈化合物。所得化合物可以从反应混合物的 CH 2 Cl 2 溶液中沉淀出来，并以中等至高产率分离为纯化合物。目前的方法为压力管方法提供了一种更安全的替代方法，因为它不涉及在高压下使用 KCN。