1,2-双(二氯膦)-1,2-二甲基肼 | 37170-64-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 1,2-双(二氯膦)-1,2-二甲基肼
• 英文名称: N,N'-bis(dichlorophosphino)-N,N'-dimethylhydrazine
• 英文别名: 1,2-bis(dichlorophosphino)-1,2-dimethylhydrazine；N,N'-bis(dichlorophosphino)dimethylhydrazine；bis(dichlorophosphino)-1,2-dimethylhydrazine；Cl2PN(Me)N(Me)PCl2；1,2-bis(dichlorophosphino)-1,2-dimethyl hydrazine；1,2-bis(dichlorophosphanyl)-1,2-dimethylhydrazine
• CAS: 37170-64-2
• 化学式: C₂H₆Cl₄N₂P₂
• 分子量: 261.843
• InChiKey: QUBGOLWADXVEJJ-UHFFFAOYSA-N

物化性质

• 沸点：
  242.0±23.0 °C(Predicted)
• 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)：
  3.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2928000090
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R20/21/22,R36/37/38
• 储存条件：
  存于阴凉干燥处

SDS

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Section 1: Product Identification
Chemical Name: 1,2-Bis(dichlorophosphino)-1,2-dimethylhydrazine, min. 98%
CAS Registry Number: 37170-64-2
Formula: Cl2PN(CH3)N(CH3)PCl2
EINECS Number: none
Chemical Family: organophosphorus compound
Synonym: None

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title Compound 37170-64-2 100% no data no data

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Section 3: Hazards Identification
Harmful by inhalation and if swallowed. Inhalation of vapors may lead to headache and dizziness. Corrosive to
Emergency Overview:
skin, eyes and mucous membranes.
Primary Routes of Exposure: Ingestion, skin, inhalation
Eye Contact: Causes burns to the eyes.
Skin Contact: Causes burns to the skin.
The material has a pungent odor. Inhalation may lead to headaches and dizziness. Corrosive to nose and
Inhalation:
mucous membranes.
Ingestion: Harmful if swallowed.
Acute Health Affects: Harmful by inhalation and if swallowed. Corrosive to skin, eyes and respiratory tract.
Chronic Health Affects: No information available 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: no data
Explosion Limits: no data
Extinguishing Medium: carbon dioxide, dry powder or foam
If involved in a fire, fire fighters should be equipped with a NIOSH approved positive pressure self-contained
Special Fire Fighting Procedures:
breathing apparatus 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 hazards.

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SECTION 6: Accidental Release Measures
Small spills can be mixed with vermiculite or other suitable absorbents. Spillage in areas not adequately
Spill and Leak Procedures: ventilation will require an evacuation of site. Emergency response teams will require self-contained breathing
apparatus. Spill should be absorbed into vermiculite or other suitable absorbent.

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SECTION 7: Handling and Storage
Handling and Storage: Material must be handled and stored under an inert atmosphere of nitrogen or argon.

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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 gloves and clothing.
Ventilation: Material has a pungent odor. Always handle 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: Material has a pungent odor. Always handle 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: colorless to slightly cloudy liq.
Molecular Weight: 261.84
Melting Point: no data
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: acidic odor
Solubility in Water: reacts with water

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SECTION 10: Stability and Reactivity
Stability: air and moisture-sensitive liquid
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: contact with air and moisture
Incompatibility: water, oxidizing agents and halogens
carbon dioxide, carbon monoxide, phosphorus pentoxide, nitrogen oxides, hydrogen chloride, and organic
Decomposition Products:
fumes.

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

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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 local, state and federal regulations.

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SECTION 14: Transportation
Shipping Name (CFR): Corrosive liquids, N.O.S.
Hazard Class (CFR): 8
Additional Hazard Class (CFR): NA
Packaging Group (CFR): II
UN ID Number (CFR): UN# 1760
Shipping Name (IATA): Corrosive liquid, N.O.S.
Hazard Class (IATA): 8
Additional Hazard Class (IATA): NA
Packaging Group (IATA): II
UN ID Number (IATA): UN# 1760

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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：

  1,2-双(二氯膦)-1,2-二甲基肼 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 2,5-Dichloro-3,4-dimethyl-[1,3,4,2,5]oxadiazadiphospholidine
  参考文献：
  名称：

  Noeth,H.; Ullmann,R., Chemische Berichte, 1976, vol. 109, p. 1942 - 1963

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-二甲基肼 在 三氯化磷 作用下， 生成 1,2-双(二氯膦)-1,2-二甲基肼
  参考文献：
  名称：

  Kriel, Frederik H.; Coates, Judy, South African Journal of Chemistry, 2012, vol. 65, p. 271 - 279

  摘要：

  DOI：

文献信息

• Ligand effects in chromium diphosphine catalysed olefin co-trimerisation and diene trimerisation
  作者：Lucy E. Bowen、Manutsavin Charernsuk、Thomas W. Hey、Claire L. McMullin、A. Guy Orpen、Duncan F. Wass

  DOI：10.1039/b913302j

  日期：——

  A series of symmetric and unsymmetric N,N-bis(diarylphosphino)amine (‘PNP’) ligands (Ar2PN(R)PNAr′2: R = Me, Ar2 = o-anisyl, Ar′2 = Ph, 1, R = Me, Ar2 = o-tolyl, Ar′2 = Ph, 2, R = Me, Ar2 = Ph(o-ethyl), Ar′2 = Ph, 3, R = Me, Ar2 = Ar′2 = o-anisyl, 4, R = iPr, Ar2 = Ar′2 = Ph, 5) and symmetric N,N′-bis(diarylphosphino)dimethylhydrazine (‘PNNP’) ligands (Ar2PN(Me)N(Me)PAr2: Ar2 = o-tolyl, 6, Ar2 = o-anisyl, 7) have been synthesised. Catalytic screening for ethene/styrene co-trimerisation and isoprene trimerisation was performed via the in situ complexation to [CrCl3(THF)3] followed by activation with methylaluminoxane (MAO). PNNP catalytic systems showed a significant increase in activity and selectivity over previously reported PNP systems in isoprene trimerisation. Comparing the symmetric and unsymmetric variants in ethene and styrene co-trimerisation resulted in a switch in selectivity, an unsymmetric catalytic (o-anisyl)2PN(Me)PPh2 (1) ligand system affording unique incorporation of two styrenic monomers into the co-trimer product distribution differing from the familiar two ethene and one styrene ω-substituted alkenes. Complexes of the type [(diphosphine)Cr(CO)4] 8–11 were also synthesised, the single-crystal X-ray diffraction of which are reported. We propose the mechanisms of these catalytic transformations and an insight into the effect of the ligand series on the chromacyclic catalytic intermediates.

  一系列对称和不对称的N,N-bis(diarylphosphino)胺（‘PNP’）配体（Ar2PN(R)PNAr′2: R = Me, Ar2 = o-甲氧基苯基, Ar′2 = 苯, 1; R = Me, Ar2 = o-甲苯基, Ar′2 = 苯, 2; R = Me, Ar2 = 苯（o-乙基）, Ar′2 = 苯, 3; R = Me, Ar2 = Ar′2 = o-甲氧基苯基, 4; R = iPr, Ar2 = Ar′2 = 苯, 5）和对称的N,N′-bis(diarylphosphino)二甲基肼（‘PNNP’）配体（Ar2PN(Me)N(Me)PAr2: Ar2 = o-甲苯基, 6; Ar2 = o-甲氧基苯基, 7）已被合成。通过原位与[CrCl3(THF)3]复合后激活的甲基铝氧烷（MAO）进行乙烯/苯乙烯共三聚化和异戊二烯三聚化的催化筛选。PNNP催化体系在异戊二烯三聚化中表现出了显著的活性和选择性的提高，相较于之前报道的PNP体系。在乙烯和苯乙烯共三聚化中，对称和不对称变体的比较导致选择性的转换，不对称催化（o-甲氧基苯基）2PN(Me)PPh2（1）配体体系在共三聚产物分布中独特地引入了两个苯乙烯单体，与熟悉的两个乙烯和一个苯乙烯的ω-取代烯烃有所不同。类型为[(双膦)Cr(CO)4]的配合物8-11也已合成，并报告了其单晶X射线衍射结果。我们提出了这些催化转化的机制，并深入探讨了配体系列对铬环催化中间体的影响。
• Chiral Phosphoramidites
  申请人：Reetz Manfred T.

  公开号：US20080207942A1

  公开（公告）日：2008-08-28

  Phosphoramidites with the general formulae I to VI are claimed together with the use of these compounds as ligands of transition metal compounds, in particular in transition metal catalysts, in the hydrogenation, transfer hydrogenation, hydroboration, hydrocyanation, 1,4-addition, hydroformylation, hydrosilylation, hydrovinylation, and Heck reactions of prochiral olefins, ketones, or ketimines.

  主张具有一般公式I至VI的磷酰胺酯，以及将这些化合物用作过渡金属化合物的配体，特别是在过渡金属催化剂中，在顺反式烯烃、酮或酮亚胺的氢化、转移氢化、氢硼化、氢氰化、1,4-加成、羰基化、硅烷化、氢乙烯化和Heck反应中。
• The preparation and coordination chemistry of phosphorus(iii) derivatives of dialkyl hydrazines
  作者：Alexandra M. Z. Slawin、Matthew Wainwright、J. Derek Woollins

  DOI：10.1039/b107072j

  日期：2002.2.5

  The formation of the new inorganic hydrazine based ligands R2PNR′NR′PR2 [R′ = Et, R = Cl, Ph, OPh, CH2Ph, o-MeOC6H4: R′ = Me, R = o-MeC6H4, o-MeOC6H4] is reported. These ligands have been complexed at Pd(II) and Pt(II) centres and demonstrative X-ray structures have been determined. When R = o-MeOC6H4 the oxygen atoms of two of the OMe groups coordinate pseudo axially.

  新的基于无机肼的配体R 2 PNR'NR'PR 2 [R'= Et，R = Cl，Ph，OPh，CH 2 Ph，o -MeOC 6 H 4的形成：R'= Me，R = o报道了-MeC 6 H 4，o -MeOC 6 H 4 ]。这些配体已经在Pd（II）和Pt（II）中心络合，并且确定了X射线的结构。当R ＝ o- MeOC 6 H 4时，两个OMe基团的氧原子伪轴向配位。
• Solid-State Structures of<i>trans</i>-[RuCl₂{Cl₂PN(Me)N(Me)PCl₂}₂] and<i>cis</i>-[MCl₂{Cl₂PN(Me)N(Me)PCl₂}] (M = Pt^IIand Pd^II) Studied by X-ray Crystallography and¹³C CPMAS NMR Spectroscopy
  作者：Satoshi Takara、Andrei S. Batsanov、Douglas J. Schaffer、Michael Takase、Janice A. Kunishige、Susan J. Lee

  DOI：10.1246/bcsj.80.1776

  日期：2007.9.15

  Solid-state structures of trans-[RuCl2Cl2PN(Me)N(Me)PCl2}2] (1), cis-[PdCl2Cl2PN(Me)N(Me)PCl2}] (2), and cis-[PtCl2Cl2PN(Me)N(Me)PCl2}] (3) were studied by using 13C CPMAS NMR spectroscopy and X-ray crystallography. The ruthenium atom in 1 was on a crystallographic inversion center and had a slightly distorted octahedral coordination. 2 and 3 contained palladium and platinum atoms in a square-planar geometry, respectively. In 2, axial sites of the Pd atom were filled by intermolecular Pd···Cl contacts to form an infinite chain. Molecules of 3 pack in an edge-to-face manner and no obvious “axial” contacts at the Pt atom were observed. Different geometries of hydrazide nitrogens in 1, 2, and 3 were observed: in 1 and 2, one of the nitrogen atoms was trigonal planar and the other one was pyramidal; the two hydrazine nitrogen atoms in 3 had trigonal planar geometry. 13C CPMAS NMR spectra are consistent with X-ray data. The P–N distances are shorter than normally accepted P–N single bond lengths, suggesting a degree of P–N π bonding.

  利用 13C CPMAS NMR 光谱和 X 射线晶体学研究了反式-[RuCl2Cl2PN(Me)N(Me)PCl2}2]（1）、顺式-[PdCl2Cl2PN(Me)N(Me)PCl2}]（2）和顺式-[PtCl2Cl2PN(Me)N(Me)PCl2}]（3）的固态结构。1 中的钌原子位于晶体学反转中心，具有轻微扭曲的八面体配位。2 和 3 中的钯原子和铂原子分别呈正方形几何结构。在 2 中，钯原子的轴向位点被分子间的钯--铂接触填满，形成一个无限链。3 的分子以边对面的方式堆积，在铂原子上没有观察到明显的 "轴向 "接触。在 1、2 和 3 中观察到肼氮原子的不同几何形状：在 1 和 2 中，一个氮原子为三棱锥平面，另一个为金字塔形；3 中的两个肼氮原子为三棱锥平面。13C CPMAS NMR 光谱与 X 射线数据一致。P-N 间距比通常认为的 P-N 单键长度短，表明存在一定程度的 P-N π 键合。
• [EN] METHOD FOR PRODUCING AMIDINE DERIVATIVES<br/>[FR] PROCÉDÉ DE PRODUCTION DE DÉRIVÉS D'AMIDINE
  申请人：BIOCRYST PHARM INC

  公开号：WO2016029216A2

  公开（公告）日：2016-02-25

  The invention provides methods and intermediates useful in the synthesis of a compound of formula (I): or a pharmaceutically acceptable salt, solvate, ester or prodrug thereof; wherein the variables are as defined herein.

  本发明提供了用于合成式(I)化合物的方法和中间体，或其药学上可接受的盐、溶剂和前药酯；其中变量如本文所定义。