1,1,1,3,3,3-六溴丙酮 | 23162-64-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,1,1,3,3,3-六溴丙酮
• 英文名称: hexabromoacetone
• 英文别名: 1,1,1,3,3,3-hexabromoacetone；HBA；1,1,1,3,3,3-hexabromopropan-2-one
• CAS: 23162-64-3
• 化学式: C₃Br₆O
• 分子量: 531.456
• InChiKey: IHAWQAMKUMLDIT-UHFFFAOYSA-N

物化性质

• 熔点：
  108-111 °C
• 沸点：
  359.8±37.0 °C(Predicted)
• 密度：
  3.442±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xn,N
• 安全说明：
  S24/25,S61
• 危险标志：
  GHS07
• 危险类别码：
  R22,R51/53
• 危险品运输编号：
  UN 2811 6.1/PG 3
• 危险性描述：
  H302

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 1,1,1,3,3,3-Hexabromoacetone
CAS-No. : 23162-64-3
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]
Acute toxicity, Oral (Category 4)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Harmful if swallowed. Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic
environment.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
Precautionary statement(s) none
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R22 Harmful if swallowed.
R51/53 Toxic to aquatic organisms, may cause long-term adverse effects in the
aquatic environment.
S-phrase(s)
S24/25 Avoid contact with skin and eyes.
S61 Avoid release to the environment. Refer to special instructions/ Safety
data sheets.
Other hazards
Lachrymator.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C3Br6O
Molecular Weight : 531,46 g/mol
Component Concentration
1,1,1,3,3,3-Hexabromoacetone
CAS-No. 23162-64-3 -

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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
Flush eyes with water as a precaution.
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
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, Hydrogen bromide 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 dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Avoid breathing dust.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the
environment must be avoided.
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.
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
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
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: powder
Colour: light yellow
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 108 - 111 °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
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion Harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
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
Toxic to aquatic life.

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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: 2811 IMDG: 2811 IATA: 2811
UN proper shipping name
ADR/RID: TOXIC SOLID, ORGANIC, N.O.S. (1,1,1,3,3,3-Hexabromoacetone)
IMDG: TOXIC SOLID, ORGANIC, N.O.S. (1,1,1,3,3,3-Hexabromoacetone)
IATA: Toxic solid, organic, n.o.s. (1,1,1,3,3,3-Hexabromoacetone)
Transport hazard class(es)
ADR/RID: 6.1 IMDG: 6.1 IATA: 6.1
Packaging group
ADR/RID: III IMDG: III IATA: III
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

反应信息

• 作为反应物：
  描述：

  1,1,1,3,3,3-六溴丙酮 在 ammonium hydroxide 作用下， 生成 三溴乙酰胺
  参考文献：
  名称：

  亲电子溴碳与假卤化物阴离子的卤素键†

  摘要：

  紫外可见测量表明，拟卤化物阴离子的相互作用，A -（A - = N 3 -，NCO -，NCS - ）中，用亲电bromocarbons，R-溴（R-BR = CBR 4，CBR 3 NO 2，CBR 3 CONH 2，CBR 3 H，CBR 3楼CBR 3 CN或C 3溴2 ˚F 6），在溶液中导致形成[R-BR，A的-]复合体。这些缔合体的特征是在200-350 nm范围内有很强的吸收带，显示出与相互作用的阴离子和R-Br亲电试剂的前沿（HOMO-LUMO）轨道的分离具有明显的Mulliken相关性。X射线晶体学研究确定了溴碳与多齿假卤化物阴离子之间的卤素键联缔合物​​的主要结构特征。具体地，在（Pr 4 N）NCO·CBr 4，（Pr 4 N）N 3 ·CBr 4和（Pr 4 N）NCO·CBr 3 NO 2共晶体中，亲电子体的溴取代基与卤素键合。 （C N或NN）氰酸根或叠氮化物阴离子的π键。CBr

  DOI：

  10.1039/c4cp00976b
• 作为产物：
  描述：

  3,3,5-三溴环戊烷-1,2,4-三酮 生成 1,1,1,3,3,3-六溴丙酮
  参考文献：
  名称：

  Hantzsch; Strasser, Justus Liebigs Annalen der Chemie, 1931, vol. 488, p. 203,209

  摘要：

  DOI：
• 作为试剂：
  描述：

  壬酸 在 吡啶 、 2,2,2-三氯乙酰胺 、 1,1,1,3,3,3-六溴丙酮 、 三苯基膦 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 1.5h， 生成 2,3-二羟基丙基壬酸酯
  参考文献：
  名称：

  利用六溴丙酮保护醇和醛，并在紫外线照射下使乙缩醛，缩酮和肟脱保护

  摘要：

  六溴丙酮（HBA）有效地用于保护醇和醛，以及对苯甲醛二甲基乙缩醛，Solketal以及其他缩醛和缩酮进行脱保护。在仅10分钟内，甘油的保护产生了90％的solketal，苯甲醛的保护得到了95％的苯甲醛二甲基乙缩醛。仅用2.5mol％的HBA，在15秒内在UV辐射下苯甲醛二甲基乙缩醛的脱保护得到超过90％的苯甲醛产率。HBA还成功用于脱氧。发现溶剂在这些反应的HBA效率中起着重要作用。

  DOI：

  10.1007/s11164-017-3168-0

文献信息

• Hexabromoacetone as tribromoacetylating agent of alcohols and amines and as mediator in the conversion of carboxylic acids into amides in the presence of triphenylphosphine
  作者：Fabrício G. Menezes、Rosane Kolling、Adaílton J. Bortoluzzi、Hugo Gallardo、César Zucco

  DOI：10.1016/j.tetlet.2009.03.093

  日期：2009.5

  Hexabromoacetone has been used as an alternative tribromoacetylating agent of primary alcohols and amines and as mediator in the conversion of carboxylic acids into amides in the presence of triphenylphosphine. The reactions have been performed under mild conditions with moderate to good yields. All the products have been adequately characterized by their physical and spectroscopic properties.

  六溴丙酮已用作伯醇和胺的替代三溴乙酰化剂，并在三苯膦存在下将羧酸转化为酰胺时用作介体。反应已在温和的条件下以中等至良好的产率进行。所有产品均已通过其物理和光谱特性充分表征。
• Experimental and Computational Probes of the Nature of Halogen Bonding: Complexes of Bromine-Containing Molecules with Bromide Anions
  作者：Sergiy V. Rosokha、Charlotte L. Stern、Jeremy T. Ritzert

  DOI：10.1002/chem.201300577

  日期：2013.7.1

  [RBr, Br−] complexes show intense absorption bands in the 200–350 nm range which follow the same Mulliken correlation as those observed for the charge‐transfer associates of bromide anions with common organic π‐acceptors. For a wide range of the associates, intermolecular RBr⋅⋅⋅Br− separations decrease and intramolecular CBr bond lengths increase proportionally to the Br−→RBr charge transfer; and the

  卤键的性质通过一系列电bromocarbons R的联营的实验和计算表征检查溴R（ BR = CBR 3楼CBR 3 NO 2，CBR 3 COCBr 3，CBR 3 CONH 2，CBR 3 CN等）和溴化物阴离子。的[R 溴，溴- ]配合物表现出在200-350纳米范围内强烈吸收带，其遵循相同的马利肯相关的那些用于与普通有机π共受体溴化物阴离子的电荷转移联营观察。对于广泛的同伴，分子间RBr⋅⋅⋅Br -分离减少和分子内Ç  Br键长度成比例地增加于BR - →R 溴电荷转移; 和R的能量 Br⋅⋅⋅Br -键与轨道（电荷转移）和静电相互作用的线性组合相关。上的整体，光谱，结构和热力学特性[R 溴，溴- ]络合物表明除了静电，轨道（电荷转移）的相互作用在R发挥至关重要的作用 Br⋅⋅⋅Br -卤素键。这表明，除了控制超分子组装体的几何形状以外，卤素键还导致相互作用的物
• Continuum of covalent to intermolecular bonding in the halogen-bonded complexes of 1,4-diazabicyclo[2.2.2]octane with bromine-containing electrophiles
  作者：Craig Weinberger、Rachel Hines、Matthias Zeller、Sergiy V. Rosokha

  DOI：10.1039/c8cc04629h

  日期：——

  A gradual change of Br⋯N bond lengths and strengths from the values typical for intermolecular associates to that characteristic of a covalent bond was observed in a series of halogen-bonded complexes. This continuum reveals a fundamental relationship between the limiting types of bonding and implies the onset of covalency in the intermolecular interactions.

  在一系列卤素键合的配合物中，观察到Br⋯N键长和强度从分子间缔合体的典型值到共价键特征的逐渐变化。该连续体揭示了键合的限制类型之间的基本关系，并暗示了分子间相互作用中共价的开始。
• 2-thio-1,3,4-oxadiazoles derivatives as sphingosine-1 phosphate receptors modulators
  申请人：Allergan, Inc.

  公开号：US08729110B1

  公开（公告）日：2014-05-20

  The present invention relates to novel 2-thio-1,3,4-oxadiazoles derivatives, processes for preparing them, pharmaceutical compositions containing them and their use as pharmaceuticals as modulators of sphingosine-1-phosphate receptors.

  本发明涉及新型2-硫代-1,3,4-噁二唑衍生物，其制备过程，含有它们的制药组合物以及它们作为拟调节鞘氨醇-1-磷酸受体的药物的用途。
• 2-THIO-1,3,4-OXADIAZOLES DERIVATIVES AS SPHINGOSINE-1 PHOSPHATE RECEPTORS MODULATORS
  申请人：Allergan, Inc.

  公开号：US20140135291A1

  公开（公告）日：2014-05-15

  The present invention relates to novel 2-thio-1,3,4-oxadiazoles derivatives, processes for preparing them, pharmaceutical compositions containing them and their use as pharmaceuticals as modulators of sphingosine-1-phosphate receptors.

  本发明涉及新型2-硫代-1,3,4-噁二唑衍生物，其制备方法、含有它们的制药组合物以及它们作为拟南芥鞘氨醇-1-磷酸受体调节剂的药物使用。