1,2-双(二氯膦酰)苯 | 82495-67-8

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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-双(二氯膦酰)苯
• 中文别名: 1,2-双（二氯膦基）苯；1,2-双(二氯磷酸基)苯
• 英文名称: 1,2-bis(dichlorophosphanyl)benzene
• 英文别名: 1,2-bis(dichlorophosphino)benzene；o-bis(dichlorophosphino)benzene；dichloro-(2-dichlorophosphanylphenyl)phosphane
• CAS: 82495-67-8
• 化学式: C₆H₄Cl₄P₂
• 分子量: 279.857
• InChiKey: IGYHSFVSIYJSML-UHFFFAOYSA-N

物化性质

• 沸点：
  97-99 °C(Press: 0.001 Torr)
• 密度：
  1.545 g/mL at 25 °C
• 闪点：
  >110℃

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  12
• 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

• WGK Germany：
  3
• 储存条件：
  室温

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 1,2-Bis(dichlorophosphino)benzene
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 82495-67-8
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
Skin corrosion (Category 1B), H314
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
C Corrosive R34
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Danger
Hazard statement(s)
H314 Causes severe skin burns and eye damage.
Precautionary statement(s)
P280 Wear protective gloves/ protective clothing/ eye protection/ face
protection.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
P310 Immediately call a POISON CENTER or doctor/ physician.
Supplemental Hazard none
Statements
Other hazards
Stench.

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SECTION 3: Composition/information on ingredients
Substances
Formula : C6H4Cl4P2
Molecular Weight : 279,86 g/mol
CAS-No. : 82495-67-8
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
1,2-Bis(dichlorophosphino)benzene
CAS-No. 82495-67-8 Skin Corr. 1B; H314 <= 100 %
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
1,2-Bis(dichlorophosphino)benzene
CAS-No. 82495-67-8 C, R34 <= 100 %
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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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
Take off contaminated clothing and shoes immediately. 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
Do NOT induce vomiting. 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
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
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, Oxides of phosphorus, Hydrogen chloride gas
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 breathing vapours, mist or gas. Ensure adequate ventilation.
Evacuate personnel to safe areas.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Soak up with inert absorbent material and dispose of as hazardous waste. 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 inhalation of vapour or mist.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Handle and store under inert gas. Air and moisture sensitive. Stench.
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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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
Tightly fitting safety goggles. Faceshield (8-inch minimum). 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
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator
with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup
to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air
respirator. Use respirators and components tested and approved under appropriate government
standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: Semi-solid melting to a liquid
b) Odour Stench.
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point > 110 °C
h) Evapouration 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 1,5451 g/cm3 at 25 °C
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignition 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
Stable under recommended storage conditions.
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
In the event of fire: see section 5

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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 sensitisation
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
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available
Cough, Shortness of breath, Headache, Nausea, Vomiting

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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
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
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.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: 3265 IMDG: 3265 IATA: 3265
UN proper shipping name
ADR/RID: CORROSIVE LIQUID, ACIDIC, ORGANIC, N.O.S. (1,2-Bis(dichlorophosphino)benzene)
IMDG: CORROSIVE LIQUID, ACIDIC, ORGANIC, N.O.S. (1,2-Bis(dichlorophosphino)benzene)
IATA: Corrosive liquid, acidic, organic, n.o.s. (1,2-Bis(dichlorophosphino)benzene)
Transport hazard class(es)
ADR/RID: 8 IMDG: 8 IATA: 8
Packaging group
ADR/RID: II IMDG: II IATA: II
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
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

1,2-双(二氯磷酸基)苯是一种有用的化工原料，在相关科研中也有广泛应用。

反应信息

• 作为反应物：
  描述：

  1,2-双(二氯膦酰)苯 在 trans-(S)-(+)-bis(μ-chloro)bis[N,N-dimethyl-α-(2-naphthyl)ethylamine-C,N]dipalladium 、 叔丁基氯化镁 、 magnesium 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 25.33h， 生成 (S,S)-BenzP*
  参考文献：
  名称：

  合成，反应性和拆分的C 2对称，对苯二甲酸，立体异构苯二膦，手性双（膦）的基础。

  摘要：

  尽管二膦酸（R 2 P–PR 2）中的金字塔倒置障碍与膦（PR 3）中的金字塔倒置障碍相似，但很少有人将P-立体异构手性二膦用作不对称合成的基础。报道了苯并二膦反式-1,2-（（P（t- Bu））2 C 6 H 4的合成，反应性和拆分。与MeOTf烷基化，然后添加亲核试剂，得到了有用的C 2对称P-立体异构配体BenzP *和新型类似物。

  DOI：

  10.1021/ol301935q
• 作为产物：
  描述：

  o-Dilithiobenzol 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 1,2-双(二氯膦酰)苯
  参考文献：
  名称：

  Drewelies, Kurt; Latscha, Hans Peter, Angewandte Chemie, 1982, vol. 94, # 8, p. 642

  摘要：

  DOI：

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。
• α，β−不飽和カルボン酸の合成方法
  申请人：積水化学工業株式会社

  公开号：JP2019156790A

  公开（公告）日：2019-09-19

  【課題】α，β−不飽和カルボン酸の生成量を向上させることができるα，β−不飽和カルボン酸の合成方法。【解決手段】α,β−不飽和カルボン酸の合成方法であって、遷移金属錯体に、ルイス酸及び塩基の存在下で、アルケンと二酸化炭素とを反応させて、中間体として特定の構造を有する金属ラクトン化合物を形成させると共に前記金属ラクトン化合物に前記ルイス酸及び前記塩基を作用させることを含み、前記塩基の共役酸の酸乖離定数（ｐＫａ１）と前記α,β−不飽和カルボン酸の酸乖離定数（ｐＫａ２）との関係がｐＫａ１＜ｐＫａ２であるα，β−不飽和カルボン酸の合成方法。【選択図】なし

  可以的，这段文字的中文翻译如下： 【课题】能够提高α，β-不饱和羧酸生成量的α，β-不饱和羧酸合成方法。【解决方法】一种α，β-不饱和羧酸的合成方法，包括在过渡金属配合物存在的情况下，在Lewis酸和碱存在的情况下，使烯烃和二氧化碳发生反应，形成具有特定结构的金属内酯化合物作为中间体，并使Lewis酸和碱作用于所述金属内酯化合物，其中碱的共轭酸的酸离解常数（pKa1）与α，β-不饱和羧酸的酸离解常数（pKa2）之间的关系为pKa1 < pKa2，这是一种α，β-不饱和羧酸的合成方法。【选择图】无
• Boraformylation and Silaformylation of Allenes
  作者：Tetsuaki Fujihara、Ayumi Sawada、Tatsuya Yamaguchi、Yosuke Tani、Jun Terao、Yasushi Tsuji

  DOI：10.1002/anie.201611314

  日期：2017.2

  The boraformylation of allenes with B2(pin)2 and a formate ester as boron and formyl source, respectively, proceeds in the presence of a copper catalyst. The reaction selectively affords the corresponding β‐boryl β,γ‐unsaturated aldehydes in good to high yields. Furthermore, the silaformylation of allenes was achieved with a formate ester and PhMe2Si−B(pin) as the silicon source.

  在铜催化剂的存在下，分别用B 2（pin）2和甲酸酯作为硼和甲酰基源的丙二烯的硼甲酰化。该反应选择性地以高产率至高产率提供相应的β-硼基β，γ-不饱和醛。此外，用甲酸酯和PhMe 2 Si-B（pin）作为硅源可以实现丙二烯的甲硅烷基化。
• BINOL-Based Diphosphonites as Ligands in the Asymmetric Rh-Catalyzed Conjugate Addition of Arylboronic Acids
  作者：Manfred T. Reetz、Dominique Moulin、Andreas Gosberg

  DOI：10.1021/ol010219y

  日期：2001.12.1

  [reaction: see text] BINOL-based diphosphonites having achiral backbones are useful ligands in the Rh-catalyzed conjugate addition of arylboronic acids to alpha,beta-unsaturated carbonyl compounds. The nature of the achiral backbone determines the direction and degree of enantioselectivity, with er values of up to 99.5:0.5 possible.

  [反应：见正文]具有非手性骨架的基于BINOL的二膦酸酯是芳基硼酸在Rh催化的向α，β-不饱和羰基化合物的共轭加成反应中的有用配体。非手性骨架的性质决定了对映选择性的方向和程度，er值可能高达99.5：0.5。
• Ligand-controlled Iron-catalyzed Cross Coupling of Benzylic Chlorides with Aryl Grignard Reagents
  作者：Shintaro Kawamura、Masaharu Nakamura

  DOI：10.1246/cl.2013.183

  日期：2013.2.5

  The selective cross coupling of benzylic chlorides with aryl Grignard reagents has been achieved by using catalytic amounts of FeCl2 and electronically tuned ortho-phenylenebisphosphine ligands. Al...

  苄基氯化物与芳基格氏试剂的选择性交叉偶联已通过使用催化量的 FeCl2 和电子调谐的邻亚苯基双膦配体实现。阿尔...