2-二苯基膦-6-甲基吡啶 | 132682-77-0

• 物质功能分类: 医药中间体 - 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: 2-二苯基膦-6-甲基吡啶
• 英文名称: 2-(diphenylphosphino)-6-methylpyridine
• 英文别名: diphenyl(6-methyl-2-pyridyl)phosphine；diphenyl(6-methyl-pyrid-2-yl)phosphine；2-(diphenylphosphanyl)-6-methylpyridine；diphenyl-(6-methyl-pyridin-2-yl)phosphine；2-Diphenylphosphino-6-methylpyridine；(6-methylpyridin-2-yl)-diphenylphosphane
• CAS: 132682-77-0
• 化学式: C₁₈H₁₆NP
• 分子量: 277.305
• InChiKey: XEXYRTTUCDBSPJ-UHFFFAOYSA-N

物化性质

• 熔点：
  81-83°C
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  29333990
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

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Section 1: Product Identification
Chemical Name: 2-Diphenylphosphino-6-methylpyridine, 98%
CAS Registry Number: 132682-77-0
Formula: C18H16NP
EINECS Number: none
Chemical Family: organophosphine ligand
Synonym: 2-Diphenylphosphanyl-6-methyl-pyridine

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 132682-77-0 100% no data no data

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Section 3: Hazards Identification
Emergency Overview: Irritating to skin, eyes and respiratory tract. May be harmful if swallowed.
Primary Routes of Exposure: Inhalation, skin, eyes
Eye Contact: Causes moderate irritation of the eyes.
Skin Contact: Causes mild to moderate irritation of the skin.
Inhalation: Inhalation causes irritation to the nose, mucous membranes and respiratory tract.
Ingestion: No specific information is available on the physiological effects of ingestion.
Acute Health Affects: Irritating to skin, eyes and respiratory tract.
Chronic Health Affects: No information on long-term chronic effects.
NTP: No
IARC: No
OSHA: No

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SECTION 4: First Aid Measures
Immediately flush the eyes with copious amounts of water for at least 10-15 minutes. A victim may need
Eye Exposure:
assistance in keeping their eye lids open. Get immediate medical attention.
Wash the affected area with water. Remove contaminated clothes if necessary. Seek medical assistance if
Skin Exposure:
irritation persists.
Remove the victim to fresh air. Closely monitor the victim for signs of respiratory problems, such as difficulty
Inhalation:
in breathing, coughing, wheezing, or pain. In such cases seek immediate medical assistance.
Seek medical attention immediately. Keep the victim calm. Give the victim water (only if conscious). Induce
Ingestion:
vomiting only if directed by medical personnel.

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SECTION 5: Fire Fighting Measures
Flash Point: no data
Autoignition Temperature: none
Explosion Limits: none
Extinguishing Medium: carbon dioxide, dry powder or foam.
Fire fighters should be equipped with a NIOSH approved positive pressure self-contained breathing apparatus
Special Fire Fighting Procedures:
and full protective clothing.
Hazardous Combustion and If involved in a fire this material may emit toxic organic fumes and vapors of phosphorus pentoxide.
Decomposion Products:
Unusual Fire or Explosion Hazards: No unusual fire or explosion hazard.

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SECTION 6: Accidental Release Measures
Small spills can be mixed with vermiculite, sodium carbonate or other suitable non combustible adsorbent and
Spill and Leak Procedures:
swept up.

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SECTION 7: Handling and Storage
Handling and Storage: Store the material in a cool, dry place in a tightly sealed container.

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SECTION 8: Exposure Controls and Personal Protection
Eye Protection: Always wear approved safety glasses when handling a chemical substance in the laboratory.
Skin Protection: Wear protective clothing and gloves.
Ventilation: Handle the material in an efficient fume hood.
If ventilation is not available a respirator should be worn. The use of respirators requires a Respirator
Respirator:
Protection Program to be in compliance with 29 CFR 1910.134.
Ventilation: Handle the material in an efficient fume hood.
Additional Protection: No additional protection required.

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SECTION 9: Physical and Chemical Properties
Color and Form: white to off-white xtl.
Molecular Weight: 277.3
Melting Point: 81-83 °
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: not determined
Solubility in Water: insoluble

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SECTION 10: Stability and Reactivity
Stability: air and moisture stable
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: none
Incompatibility: strong oxidizing agents and halogens
Decomposition Products: carbon dioxide, carbon monoxide, organic fumes and phosphorus oxides.

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SECTION 11: Toxicological Information
RTECS Data: No information available in the RTECS files.
Carcinogenic Effects: no data
Mutagenic Effects: no data
Tetratogenic Effects: no data

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SECTION 12: Ecological Information
Ecological Information: No information available

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SECTION 13: Disposal Considerations
Disposal: Dispose of according to federal, state, and local regulations.

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SECTION 14: Transportation
Shipping Name (CFR): Non-hazardous
Hazard Class (CFR): NA
Additional Hazard Class (CFR): NA
Packaging Group (CFR): NA
UN ID Number (CFR): NA
Shipping Name (IATA): Non-hazardous
Hazard Class (IATA): NA
Additional Hazard Class (IATA): NA
Packaging Group (IATA): NA
UN ID Number (IATA): NA

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SECTION 15: Regulatory Information
TSCA: Not listed in the TSCA inventory.
SARA (Title 313): Title compound not listed.
Second Ingredient: none

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  p-叠氮甲苯 、 2-二苯基膦-6-甲基吡啶 以 四氢呋喃 为溶剂， 以73%的产率得到2-(p-MeC6H4NPPh2)-6-MeC5H3N
  参考文献：
  名称：

  [C（Ph（2）P = NSiMe3）{6-（2-RC5H3N）}] 2-或[CH（Ph2P = NSiMe3）{6-（2-RC5H3N）}]-（R = 3,5-二甲基-1-吡唑基或亚氨基磷杂烷基）配体。

  摘要：

  [C（Ph2P = NSiMe3）{6-（2-RC5H3N）}] 2-或[CH（Ph2P = NSiMe3）支持的几种锡（II），铅（II）和（II）配合物的合成与表征报道了{6-（2-RC5H3N）}-（R ＝ 3，5-二甲基-1-吡唑基或亚氨基磷杂烷基）配体。2-R-6- {CH2P（Ph2）= NSiMe3} C5H3N与M [N（SiMe3）2] 2（M = Sn，Pb）的反应生成锡（II）和铅（II）络合物[M {C（ Ph2P ＝ NSiMe3）{6-（2-RC5H3N）}}] 2 [3，M ＝ Sn，R ＝ 3，5-二甲基-1-吡唑基。4，M = Pb，R = 3,5-二甲基-1-吡唑基; 9，M = Sn，R = Me3SiN = P（Ph2）; 10，M ＝ Pb，R ＝ Me 3 SiN ＝ P（Ph 2）]。当R = p-MeC6H4N = P（Ph2）时，N，N螯合锡（II）络合物，[Sn

  DOI：

  10.1039/b906266a
• 作为产物：
  描述：

  (6-methylpyridin-2-yl)diphenylphosphine oxide 在 甲基二乙氧基硅烷 、 双(对硝基苯基)磷酸酯 作用下， 以 甲苯 为溶剂， 以88%的产率得到2-二苯基膦-6-甲基吡啶
  参考文献：
  名称：

  Highly Chemoselective Metal-Free Reduction of Phosphine Oxides to Phosphines

  摘要：

  Unprecedented chemoselective reductions of phosphine oxides to phosphines proceed smoothly in the presence of catalytic amounts of specific Bronsted acids. By utilizing inexpensive silanes, e.g., PMHS or (EtO)(2)MeSiH, other reducible functional groups such as ketones, aldehydes, olefins, nitriles, and esters are well-tolerated under optimized conditions.

  DOI：

  10.1021/ja3069165
• 作为试剂：
  描述：

  甲醇 、 2-丙炔-1-醇 在 甲烷磺酸 、 palladium diacetate 、 2-二苯基膦-6-甲基吡啶 作用下， 以 1,2-二氯乙烷 为溶剂， 60.0 ℃ 、3.04 MPa 条件下， 反应 3.0h， 以85.6%的产率得到2-(羟甲基)丙烯酸甲酯
  参考文献：
  名称：

  炔丙醇烷氧羰基化的新见解

  摘要：

  Pd（OAc）2与二苯基-（6-甲基-吡啶-2-基）膦和甲磺酸结合可有效地催化炔丙醇具有挑战性的羰基化反应。在20–50°C的二氯乙烷中，该反应几乎可以完全实现区域选择性的2-（羟甲基）丙烯酸烷基酯。在50°C下工作时，可实现高达450 h -1的周转频率数（TOF），而在30°C下可获得约730的最大周转数（TON）。催化剂的寿命受到限制，因为羰基化产物与配体的磷原子反应生成季phospho盐。该反应导致催化剂失活，并最终导致钯黑的形成。

  DOI：

  10.1016/j.mcat.2017.09.029

文献信息

• Synthesis, Structure, and Characterization of Dinuclear Copper(I) Halide Complexes with P^N Ligands Featuring Exciting Photoluminescence Properties
  作者：Daniel M. Zink、Michael Bächle、Thomas Baumann、Martin Nieger、Michael Kühn、Cong Wang、Wim Klopper、Uwe Monkowius、Thomas Hofbeck、Hartmut Yersin、Stefan Bräse

  DOI：10.1021/ic300979c

  日期：2013.3.4

  highly luminescent dinuclear copper(I) complexes has been synthesized in good yields using a modular ligand system of easily accessible diphenylphosphinopyridine-type P^N ligands. Characterization of these complexes via X-ray crystallographic studies and elemental analysis revealed a dinuclear complex structure with a butterfly-shaped metal-halide core. The complexes feature emission covering the visible

  使用易于获得的二苯基膦基吡啶型P ^ N配体的模块化配体系统，已经以高收率合成了一系列高发光度的双核铜（I）配合物。通过X射线晶体学研究和元素分析对这些配合物进行表征，揭示出具有蝶形金属卤化物核的双核配合物结构。配合物具有发射光谱，覆盖从蓝色到红色的可见光谱，以及高达96％的高量子产率。密度泛函理论计算表明，HOMO主要由金属核和桥接卤化物的轨道组成，而LUMO主要位于P ^ N配体的杂环部分。因此，桥联配体的杂环部分的修饰允许发光波长的系统调节。通过增加N-杂环的芳族体系或通过吡啶基部分的官能化，获得具有在481至713nm处的最大发射的配合物。对于代表性的化合物，已表明可以将环境温度发射指定为热激活的延迟荧光，其特征在于在ϕ时只有6.5μs的极短的发射衰减时间。PL = 0.8。提出将这些化合物应用于OLED中的单重态收获。
• The Chemistry of New Nitrosyltungsten Complexes with Pyridyl-Functionalized Phosphane Ligands
  作者：Jürgen Baur、Heiko Jacobsen、Peter Burger、Georg Artus、Heinz Berke、Lutz Dahlenburg

  DOI：10.1002/1099-0682(200007)2000:7<1411::aid-ejic1411>3.0.co;2-m

  日期：2000.7

  MeCN from [W(CH3CN)3(CO)2(NO)][BF4] led to the following cationic compounds incorporating mono- and bidentate coordinated phosphane ligands: cis,cis-[W(CO)2(NO)(Ph2PR)(η2-Ph2PR)][BF4], [R = 2-pyridyl (9a), 2-picolyl (11)], cis,cis-[W(CO)(NO)(η2-Ph2Ppy)2][BF4] (20), trans,trans-[W(CO)(NO)(η2-Ph2Ppy)2][BPh4] (21), fac-[W(CO)2(NO)(Me2Ppy)3][BF4] (16), fac-[W(CO)2(NO)(Me2P-tert-Bupy)3][BF4] (18), cis,c

  吡啶基膦的配位化学，例如 2-(6-tert-butylpyridyl)diphenylphosphane (Ph2P-tert-Bupy) (6) 和 2-(6-tert-butylpyridyl)二甲基膦 (Me2P-tert-Bupy) (7) 对报道了许多亚硝基钨配合物。[W(CH3CN)3(CO)2(NO)][BF4] 中松散配位的 MeCN 的置换导致以下阳离子化合物结合了单齿和双齿配位磷烷配体：顺式，顺式-[W(CO)2( NO)(Ph2PR)(η2-Ph2PR)][BF4]，[R = 2-吡啶基 (9a)，2-吡啶甲基(11)]，顺，顺-[W(CO)(NO)(η2-Ph2Ppy) 2][BF4] (20), trans,trans-[W(CO)(NO)(η2-Ph2Ppy)2][BPh4] (21), fac-[W(CO)2(NO)(Me2Ppy)3 ][BF4] (16)
• A General Bifunctional Catalyst for the Anti-Markovnikov Hydration of Terminal Alkynes to Aldehydes Gives Enzyme-Like Rate and Selectivity Enhancements
  作者：Douglas B. Grotjahn、Daniel A. Lev

  DOI：10.1021/ja046360u

  日期：2004.10.1

  A new, bifunctional catalyst for anti-Markovnikov hydration of terminal alkynes to aldehydes (6) allows practical room-temperature hydration of alkyl-substituted alkynes. Other outstanding features include near-quantitative aldehyde yields from both alkyl- and aryl-substituted alkynes and wide functional group tolerance. The uncatalyzed rate of alkyne hydration is measured for the first time, showing

  一种用于末端炔烃反马尔可夫尼科夫水合生成醛 (6) 的新型双功能催化剂允许烷基取代炔烃在室温下实际水合。其他突出特点包括来自烷基和芳基取代的炔烃的接近定量的醛产率和广泛的官能团耐受性。首次测量炔烃水合的未催化速率，表明醛形成的酶样速率和选择性提高了 6。对于醛形成，未催化速率 <1 x 10-10 mol h-1 表示半衰期> 600 000 年。催化速率高达 23.8 mol (mol 6)-1 h-1 和 10 000:1 比有利于醛。因此，由 6 引起的速率和选择性的变化分别 > 2.4 x 1011 和 300 000。
• Nonsymmetrical Bis-Azine Biaryls from Chloroazines: A Strategy Using Phosphorus Ligand-Coupling
  作者：Benjamin T. Boyle、Michael C. Hilton、Andrew McNally

  DOI：10.1021/jacs.9b08504

  日期：2019.9.25

  in demand as these compounds have multiple applications in the chemical sciences and are challenging targets for metal-catalyzed cross-coupling reactions. Most approaches focus on developing new reagents as the formal nucleophilic coupling partner that can function in metal-catalyzed processes. We present an alternative approach using pyridine and diazine phosphines as nucleophilic partners and chloroazines

  需要独特的方法来合成双嗪联芳基化合物，因为这些化合物在化学科学中有多种应用，并且是金属催化交叉偶联反应的挑战性目标。大多数方法侧重于开发新试剂，作为可以在金属催化过程中发挥作用的正式亲核偶联伙伴。我们提出了一种替代方法，使用吡啶和二嗪膦作为亲核伙伴和氯嗪，其中杂联芳键是通过串联 SNAr-磷配体偶联序列形成的。杂芳基膦由氯嗪制备并且是长期稳定的固体。使用这种策略可以从丰富的氯嗪中形成一系列双嗪联芳基化合物，这对于使用传统方法来说是具有挑战性的。
• General and Selective Copper-Catalyzed Reduction of Tertiary and Secondary Phosphine Oxides: Convenient Synthesis of Phosphines
  作者：Yuehui Li、Shoubhik Das、Shaolin Zhou、Kathrin Junge、Matthias Beller

  DOI：10.1021/ja301764m

  日期：2012.6.13

  Novel catalytic reductions of tertiary and secondary phosphine oxides to phosphines have been developed. Using tetramethyldisiloxane (TMDS) as a mild reducing agent in the presence of copper complexes, PO bonds are selectively reduced in the presence of other reducible functional groups (FGs) such as ketones, esters, and olefins. Based on this transformation, an efficient one pot reduction/phosphination

  已经开发了将叔和仲氧化膦新型催化还原为膦的方法。在铜配合物的存在下使用四甲基二硅氧烷 (TMDS) 作为温和的还原剂，PO 键在其他可还原的官能团 (FG) 的存在下被选择性还原，例如酮、酯和烯烃。基于这种转化，有效的一锅还原/膦化多米诺序列允许以良好的产率合成各种官能化的芳族和脂肪族膦。