(R)-(+)-2,2’,6,6’-四甲氧基-4,4’-联(二(3,5-二甲苯基基)膦基)-3,3’-二联吡啶 | 442905-33-1

• 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: (R)-(+)-2,2’,6,6’-四甲氧基-4,4’-联(二(3,5-二甲苯基基)膦基)-3,3’-二联吡啶
• 中文别名: (R)-(+)-2,2',6,6'-四甲氧基-4,4'-双(二(3,5-二甲苯基)膦-3,3'-联吡啶；(R)-(-)-N-(3,5-二硝基苯甲酰基)-α-苯乙胺；(R)-(+)-2,2',6,6'-四甲氧基-4,4'-联(二(3,5-二甲苯基基)膦基)-3,3'-二联吡啶；(R)-(+)-2,2',6,6'-四甲氧基-4,4'-联(二(3,5-二甲苯基基)膦基)--3,3'-二联吡啶
• 英文名称: (R)-(+)-2,2',6,6'-tetramethoxy-4,4'-bis(di(3,5-xylyl)phosphino)-3,3'-bipyridine
• 英文别名: (R)-xylyl-CTH-P-PHOS；CTH-(R)-xylyl-P-Phos；(R)-xylyl-P-Phos；(R)-xyl-P-Phos；(R)-2,2',6,6'-tetramethoxy-4,4'-bis[di(3,5-dimethylphenyl)phosphino]-3,3'-bipyridine；(R)-2,2',6,6'-tetramethoxy-4,4'-bis(di(3,5-xylyl)phosphino)-3,3'-bipyridine；[3-[4-bis(3,5-dimethylphenyl)phosphanyl-2,6-dimethoxypyridin-3-yl]-2,6-dimethoxypyridin-4-yl]-bis(3,5-dimethylphenyl)phosphane
• CAS: 442905-33-1
• 化学式: C₄₆H₅₀N₂O₄P₂
• 分子量: 756.862
• InChiKey: JRTHAKOHBMETRC-UHFFFAOYSA-N

物化性质

• 熔点：
  190-194°C
• 沸点：
  791.1±60.0 °C(Predicted)
• 稳定性/保质期：
  按规定使用和贮存不会分解，需避开氧化物、空气、卤素。

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  54
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
: (R)-(+)-2,2',6,6'-Tetramethoxy-4,4′-bis(di(3,5-
Product name
xylyl)phosphino)-3,3'-bipyridine
CAS-No. : 442905-33-1
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]
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)
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 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.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : (R)-Xylyl-P-Phos
Formula : C46H50N2O4P2
Molecular Weight : 756,85 g/mol
Component Concentration
(R)-(+)-2,2',6,6'-Tetramethoxy-4,4'-bis(di(3,5-xylyl)phosphino)-3,3'-bipyridine
CAS-No. 442905-33-1 -

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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
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

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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), Oxides of phosphorus
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
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.

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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.
Store under inert gas.
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
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.
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).

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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 Melting point/range: 190 - 194 °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
Strong oxidizing agents
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
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

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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: - 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
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：

  (R)-(+)-2,2’,6,6’-四甲氧基-4,4’-联(二(3,5-二甲苯基基)膦基)-3,3’-二联吡啶 以 四氢呋喃 、 甲苯 为溶剂， 生成 [((R)-2,2',6,6'-tetramethoxy-4,4'-bis(di-3,5-dimethylphenylphosphine)3,3'-bipyridine)diaquapalladium(II)] trifluoromethane sulfonate
  参考文献：
  名称：

  新型手性二吡啶基膦阳离子钯（II）配合物催化苯乙烯的对映选择性双烷氧基羰基化反应

  摘要：

  制备由一系列手性二吡啶基膦[（R）-P-Phos（1），（R）-tol-P-Phos（2）和（R -Xyl-P-Phos）组成的新钯配合物（3）]已经被描述。络合物[{（R）-1 } Pd（H 2 O）2 ]（OTf）2的结构通过单晶X射线衍射确定。发现这些络合物在苯乙烯的不对称双甲氧基羰基化中有效，在最佳条件下，对-2-苯基丁二酸二甲酯（DMPS）达到高达84％ee和79％的化学选择性。另外，该复合物在DMPS上表现出几乎相同的对映选择性。

  DOI：

  10.1016/s1381-1169(02)00648-9
• 作为产物：
  描述：

  氯二(3,5-二甲基苯基)膦 在 三氯硅烷 、 双氧水 、 铜 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 (R)-(+)-2,2’,6,6’-四甲氧基-4,4’-联(二(3,5-二甲苯基基)膦基)-3,3’-二联吡啶
  参考文献：
  名称：

  一种新的手性二吡啶基膦配体Xyl-P-Phos及其在Ru催化的β-酮酯不对称加氢中的应用

  摘要：

  合成了一种新的手性二吡啶基膦配体Xyl-P-Phos，并通过单晶X射线衍射表征了（S）-Xyl-P-Phos氧化物的结构。已发现该配体的钌配合物Ru（R -Xyl-P-Phos）（C 6 H 6）Cl 2是高活性，对映选择性和空气稳定的催化剂，可用于β-酮酸酯和不对称酮的不对称氢化。在工业应用中显示出良好的潜力。

  DOI：

  10.1016/s0040-4039(02)00062-x
• 作为试剂：
  描述：

  对氰基苯乙酮 在 (R)-(+)-2,2’,6,6’-四甲氧基-4,4’-联(二(3,5-二甲苯基基)膦基)-3,3’-二联吡啶 、 苯硅烷 、 cobalt(II) diacetate tetrahydrate 作用下， 以 甲苯 为溶剂， 反应 36.0h， 以99%的产率得到(S)-1-(4-氰基苯基)乙醇
  参考文献：
  名称：

  Cobalt(ii)-catalyzed asymmetric hydrosilylation of simple ketones using dipyridylphosphine ligands in air

  摘要：

  在存在作为氢供体的PhSiH3的情况下，非消旋的二吡啶膦和易于操作的钴盐Co(OAc)2·4H2O现场形成有效的催化系统，用于多种芳基烷基酮的对映选择性还原，其对映选择性从中等到优秀（最高可达96% ee）。这种方法在空气中处理催化剂和反应物时不需要特别预防措施。

  DOI：

  10.1039/c1ob05494e

文献信息

• Method for Asymmetric Hydrosilylation of Ketones
  申请人：Chan Albert Sun-Chi

  公开号：US20080269490A1

  公开（公告）日：2008-10-30

  Method of asymmetrically hydrosilylating substrates using catalysts having a ligand of the compound of the formula (I) wherein R is optionally substituted alkyl, cycloalkyl, aryl or heteroaryl; R′ is hydrogen, optionally substituted lower alkyl; and R″ is hydrogen, halogen, optionally substituted alkyl, hydroxy, amino (e.g., primary, secondary or tertiary), alkenyl; or an enantiomer thereof; or an enantiomeric mixture thereof with a transition metal. Particularly suitable reactions include the asymmetric hydrosilylation of ketones.

  使用具有化合物公式(I)的配体的催化剂不对称地对底物进行氢硅烷化的方法 其中 R是可选择地取代的烷基、环烷基、芳基或杂环芳基; R′是氢、可选择地取代的较低烷基; 和 R″是氢、卤素、可选择地取代的烷基、羟基、氨基(例如，一级、二级或三级)、烯基; 或其对映体; 或其与过渡金属的对映混合物。特别适合的反应包括酮的不对称氢硅烷化。
• [EN] RUTHENIUM COMPLEX AND METHOD FOR PREPARING OPTICALLY ACTIVE ALCOHOL COMPOUND<br/>[FR] COMPLEXE DE RUTHÉNIUM ET PROCÉDÉ POUR PRÉPARER UN COMPOSÉ ALCOOLIQUE OPTIQUEMENT ACTIF
  申请人：TAKASAGO PERFUMERY CO LTD

  公开号：WO2011135753A1

  公开（公告）日：2011-11-03

  The present invention provides a novel ruthenium complex which has an excellent catalytic activity in terms of reactivity for asymmetric reduction of a carbonyl compound and enantioselectivity, a catalyst using the ruthenium complex, and a method for preparing optically active alcohol compounds using the ruthenium complex. The present invention relates to a ruthenium complex having ruthenacycle structure, a catalyst for asymmetric reduction consisting of the ruthenium complex, and a method for preparing optically active alcohol using the ruthenium complex.

  本发明提供了一种新型钌配合物，其在对羰基化合物的不对称还原反应活性和对映选择性方面具有优异的催化活性，以及使用该钌配合物的催化剂和制备光学活性醇化合物的方法。本发明涉及具有钌环结构的钌配合物，由该钌配合物组成的不对称还原催化剂，以及使用该钌配合物制备光学活性醇的方法。
• Homogeneous asymmetric hydrogenation catalyst
  申请人：Shimizu Hideo

  公开号：US20090203927A1

  公开（公告）日：2009-08-13

  Provide that a useful catalyst for homogeneous hydrogenation, particularly a catalyst for homogeneous asymmetric hydrogenation for hydrogenation, particularly asymmetric hydrogenation, which is obtainable with comparative ease and is excellent in economically and workability, and a process for producing a hydrogenated compound of an unsaturated compound, particularly an optically active compound using said catalyst with a high yield and optical purity.

  提供一种用于均相氢化的有用催化剂，特别是用于均相不对称氢化的催化剂，特别是不对称氢化的催化剂，该催化剂易于获得，在经济性和可操作性方面表现出色，以及一种使用该催化剂产生不饱和化合物的氢化物的方法，特别是使用高产率和光学纯度的该催化剂产生手性活性化合物。
• PROCESS FOR PRODUCING OPTICALLY ACTIVE AMINE
  申请人：TAKASAGO INTERNATIONAL CORPORATION

  公开号：US20150210657A1

  公开（公告）日：2015-07-30

  A process for producing an optically active amine compound, characterized by asymmetrically hydrogenating a prochiral carbon-nitrogen double bond in the presence of a ruthenium complex represented by general formula (1) or (2) (wherein P represents an optically active diphosphine, X represents an anionic group, and Ar represents an optionally substituted arylene group).

  一种制备光学活性胺化合物的方法，其特征在于在存在由通用式（1）或（2）表示的钌配合物的情况下，对一个丙半胱氨基双键进行不对称氢化（其中P代表光学活性二膦，X代表阴离子基团，Ar代表可选择取代的芳基基团）。
• [EN] PROCESS FOR THE PREPARATION OF CHIRAL AMINES BY ASYMMETRIC HYDROGENATION OF PROCHIRAL OXIMES<br/>[FR] PROCÉDÉ DE PRÉPARATION D'AMINES CHIRALES PAR HYDROGÉNATION ASYMÉTRIQUE D'OXIMES PROCHIRAUX
  申请人：SP PROCESS DEV AB

  公开号：WO2015178847A1

  公开（公告）日：2015-11-26

  There is provided a method for the preparation of an enantiomerically enriched amine by asymmetric hydrogenation of a prochiral oxime.

  提供了一种通过对一个非手性亚硝酮进行不对称氢化来制备对映体富集胺的方法。