1,2-二(膦酰基)苯 | 80510-04-9

• 物质功能分类: 有机原料 - 有机膦化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,2-二(膦酰基)苯
• 中文别名: 1,2-双(膦酰)苯
• 英文名称: 1,2-bis(phosphino)benzene
• 英文别名: 1,2-diphosphinobenzene；(2-phosphanylphenyl)phosphane
• CAS: 80510-04-9
• 化学式: C₆H₈P₂
• 分子量: 142.077
• InChiKey: DKFDVEXWZZOMGS-UHFFFAOYSA-N

物化性质

• 沸点：
  53-55°C 0,25mm
• 密度：
  1.101 g/mL at 25 °C(lit.)
• 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)：
  1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险品标志：
  F
• 安全说明：
  S16,S26,S27,S36/37/39,S43,S7/8
• 危险类别码：
  R17
• 海关编码：
  2931900090
• 危险品运输编号：
  UN 2924
• 储存条件：
  存放在阴凉干燥处即可。

SDS

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Section 1: Product Identification
Chemical Name: 1,2-Bis(phosphino)benzene, 98+%
CAS Registry Number: 80510-04-9
Formula: C6H4(PH2)2
EINECS Number: none
Chemical Family: organophosphine ligand
Synonym: none

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title Compound 80510-04-9 100% no data no data

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Section 3: Hazards Identification
Harmful by inhalation, in contact with skin and if swallowed. May ignite spontaneously on contact with air.
Emergency Overview:
Contact with skin may result in severe chemical burns.
Primary Routes of Exposure: Skin and inhalation
Eye Contact: May cause mild to severe irritation of the eyes.
Skin Contact: Harmful in contact with skin. May cause mild irritation of the skin, or thermal burns if ignited.
Inhalation: Harmful by inhalation. Inhalation may lead to dizziness and headaches.
Harmful if swallowed. Ingestion is an unlikely mode of entry as the material is pyrophoric and has a noxious
Ingestion:
odor.
Acute Health Affects: Harmful by inhalation, in contact with skin and if swallowed.
Chronic Health Affects: No information available on long term exposure to this material.
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 15 minutes. A victim will need
Eye Exposure:
assistance in keeping their eye lids open. Get immediate medical attention.
Wash the affected area immediately with water. Remove contaminated clothing if necessary. Seek medical
Skin Exposure:
assistance if irritation persists.
Remove victim to fresh air immediately. Keep the victim lying down and warm. Give oxygen as soon as
Inhalation:
possible. If shock occurs, respond with appropriate first aid. Transport the victim to a hospital.
Seek medical attention immediately. Keep the victim calm. Give water to dilute the toxin (only if conscious).
Ingestion:
Induce vomiting only if directed by medical personnel.

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SECTION 5: Fire Fighting Measures
Flash Point: no data
Autoignition Temperature: Pyrophoric
Explosion Limits: Pyrophoric
Extinguishing Medium: carbon dioxide, dry powder or foam
The pyrophoric liquid may reignite. Fire fighters should be equipped with an approved positive pressure
Special Fire Fighting Procedures:
self-contained 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: Spontaneously flammable in air, especially in contact with organic matter such as paper or cloth.

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SECTION 6: Accidental Release Measures
'The material may ignite spontaneously in air. Avoid static discharge. Burning material may release
toxic fumes. In case of poor ventilation, leave the area unless fitted with a self-contained breathing apparatus.
Spill and Leak Procedures:
Small spills can be mixed with ground limestone, sodium bicarbonate, or other suitable absorbents, swept up,
and held in a closed metal can.

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SECTION 7: Handling and Storage
Store in a tightly sealed container under an inert atmosphere of nitrogen or argon. Keep away from heat.
Handling and Storage: Material should be transferred under an inert atmosphere of nitrogen or argon in a efficient fume hood. Fire
may occur in emptied container and transfer lines.

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SECTION 8: Exposure Controls and Personal Protection
Always wear approved safety glasses. When handling this substance wear a face shield as added protection.
Eye Protection:
Skin Protection: Wear protective clothing and gloves. Consult with glove manufacturer to determine the proper type of glove.
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 29 CFR 1910.134.
Ventilation: Material has a pungent odor. Always handle material in an efficient fume hood.
Additional Protection: Wear a full face shield, flame resistant lab apron and suitable gloves.

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SECTION 9: Physical and Chemical Properties
Color and Form: colorless liq.
Molecular Weight: 142.08
Melting Point: no data
Boiling Point: 53-55°C /0.25mm
Vapor Pressure: no data
Specific Gravity: no data
Odor: pungent and noxious odor
Solubility in Water: insoluble

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SECTION 10: Stability and Reactivity
Stability: air-sensitive, pyrophoric liquid
Hazardous Polymerization: no hazardous polymerization
Contact with air. Material may spontaneously ignite, especially in the presence of organic matter such as
Conditions to Avoid:
paper or cloth.
Incompatibility: oxidizing agents, halogens, air (pyrophoric), halocarbons, sulfur.
Decomposition Products: carbon dioxide, carbon monoxide, organic vapors, and phosphorus pentoxide.

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SECTION 11: Toxicological Information
RTECS Data: No information available in the RTECS files.
Carcinogenic Effects: No information available.
Mutagenic Effects: No information available.
Tetratogenic Effects: No information 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 this material according to local, state and federal regulations.

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SECTION 14: Transportation
Shipping Name (CFR): Pyrophoric liquids, organic, N.O.S.
Hazard Class (CFR): 4.2
Additional Hazard Class (CFR): NA
Packaging Group (CFR): I
UN ID Number (CFR): UN# 2845
Shipping Name (IATA): Forbidden
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 on the TSCA inventory
SARA (Title 313): not regulated by SARA 313
Second Ingredient: none

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1,2-二(膦酰基)苯 在 双氧水 作用下， 反应 1.0h， 生成 1,2-苯二膦酸
  参考文献：
  名称：

  Woerz, H.-J.; Quien, E.; Latscha, H. P., Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1984, vol. 39, # 12, p. 1706 - 1710

  摘要：

  DOI：
• 作为产物：
  描述：

  1-氯-2-碘苯 在 lithium aluminium tetrahydride 作用下， 以 氨 为溶剂， 生成 1,2-二(膦酰基)苯
  参考文献：
  名称：

  1.3-Benzodiphosphole, 1.2-bis-dimethylaminoalkylidenphosphino-benzen

  摘要：

  DOI：

  10.1016/s0040-4039(01)93018-7

文献信息

• Synthesis of Chiral Hydroxyl Phospholanes from <scp>d</scp>-mannitol and Their Use in Asymmetric Catalytic Reactions
  作者：Wenge Li、Zhaoguo Zhang、Dengming Xiao、Xumu Zhang

  DOI：10.1021/jo000066c

  日期：2000.6.1

  Strategies for protection and deprotection of OH-groups in the presence of phosphines have been explored. Rate acceleration in the Baylis-Hillman reaction was observed when a hydroxyl phosphine was used as the catalyst. Rhodium complexes with chiral bisphospholanes are highly enantioselective catalysts for the asymmetric hydrogenation of various kinds of functionalized olefins such as dehydroamino

  手性羟基一膦3 [（2S，3S，4S，5S）-3,4-二羟基-2，5-二甲基-1-苯基膦烷]和双膦酸酯5a [1,2-双[（2S，3S，4S，5S） -3,4-二羟基-2,5-二甲基磷杂环戊烷基]苯]和5b [1,2-双[（2S，3S，4S，5S）-2,5-二乙基-3,4-二羟基磷杂环戊基]苯]从现成的D-甘露醇中以高收率获得。已经研究了在膦存在下保护和脱保护OH-基团的策略。当使用羟基膦作为催化剂时，在Baylis-Hillman反应中观察到速率加速。铑与手性双膦酸酯的络合物是高度对映选择性的催化剂，用于各种官能化烯烃（如脱氢氨基酸衍生物，衣康酸衍生物和烯酰胺）的不对称氢化。
• Asymmetric catalysis based on chiral phospholanes and hydroxyl phospholanes
  申请人：The Penn State Research Foundation

  公开号：US06727377B2

  公开（公告）日：2004-04-27

  Chiral phosphine ligands derived from chiral natural products including D-mannitol and tartaric acid. The ligands contain one or more 5-membered phospholane rings with multiple chiral centers, and provide high stereoselectivity in asymmetric reactions.

  来自手性天然产物的手性膦配体，包括D-甘露醇和酒石酸。这些配体含有一个或多个含有多个手性中心的5元磷环，可在不对称反应中提供高立体选择性。
• Highly Flexible Synthetic Routes to Functionalized Phospholanes from Carbohydrates
  作者：Yuan-Yong Yan、T. V. RajanBabu

  DOI：10.1021/jo991762j

  日期：2000.2.1

  Highly functionalized phospholanes 15, 17, and 26 and the corresponding diastereomers in which the configurations of the phospholane carbon-2 and carbon-5 are inverted can be readily prepared from d-mannitol by displacement of the appropriate dimesylate or cyclic sulfate with dilithiumphosphide reagents. The diols from which these ligands are prepared can also be converted into diarylphosphinite ligands

  通过用磷化二锂试剂置换合适的二甲磺酸酯或环状硫酸酯，可以容易地从d-甘露醇制备高度官能化的膦烷15、17和26以及其中膦烷碳2和碳5的构型反转的相应非对映异构体。制备这些配体的二醇也可以转化为二芳基亚膦酸酯配体。还描述了产生带有半可溶性叔丁基硫基的相关单膦的途径。这些配体和相关脱保护衍生物的配合物可能可用于有机和水介质中的对映选择性催化。
• Highly Enantioselective Hydrogenation of Simple Ketones Catalyzed by a Rh-PennPhos Complex
  作者：Qiongzhong Jiang、Yutong Jiang、Dengming Xiao、Ping Cao、Xumu Zhang

  DOI：10.1002/(sici)1521-3773(19980504)37:8<1100::aid-anie1100>3.0.co;2-3

  日期：1998.5.4

  Even alkyl methyl ketones undergo asymmetric hydrogenation with high enantioselectivity when a rhodium complex of the conformationally rigid chiral ligand 1 (Me-PennPhos; R=CH3 ) is used as the catalyst. Basic additives such as 2,6-lutidine contribute to the achievement of high enantiomeric excesses.

  当使用构象刚性手性配体1的铑配合物（Me-PennPhos； R ＝ CH 3）作为催化剂时，即使烷基甲基酮也经历高对映选择性的不对称氢化。碱性添加剂（例如2，6-二甲基吡啶）有助于实现高对映体过量。
• Rhodium-hydroxyl bisphospholane catalyzed highly enantioselective hydrogenation of dehydroamino acids and esters
  作者：Wenge Li、Zhaoguo Zhang、Dengming Xiao、Xumu Zhang

  DOI：10.1016/s0040-4039(99)01254-x

  日期：1999.9

  A chiral hydroxyl bisphospholane, 1,2-bis[(2S,3S,4S,5S)-3,4-dihydroxyl-2,5-dimethylphospholanyl]benzene (4), was synthesized from readily available d-mannitol. Its Rh(I) complex catalyzes asymmetric hydrogenation of dehydroamino acids and their ester derivatives with excellent enantioselectivities (98 to >99% ee).

  由容易获得的d-甘露糖醇合成手性羟基双膦，1,2-双[（2 S，3 S，4 S，5 S）-3,4-二羟基-2,5-二甲基磷杂环戊基]苯（4） 。它的Rh（I）配合物催化脱氢氨基酸及其酯衍生物的不对称氢化，具有出色的对映选择性（98至> 99％ee）。