2-溴十二烷 | 13187-99-0

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 烃类卤化物
• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 中文名称: 2-溴十二烷
• 英文名称: 2-bromododecane
• CAS: 13187-99-0
• 化学式: C₁₂H₂₅Br
• 分子量: 249.234
• InChiKey: GIUUCQVKMWBSRT-UHFFFAOYSA-N

物化性质

• 熔点：
  -96 °C (lit.)
• 沸点：
  130 °C/6 mmHg (lit.)
• 密度：
  1.02 g/mL at 25 °C (lit.)
• 闪点：
  >230 °F
• 保留指数：
  1505

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  13
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2903399090
• WGK Germany：
  3

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 2-Bromododecane
CAS-No. : 13187-99-0

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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)
Causes skin irritation.
Causes serious eye irritation.
May cause respiratory irritation.
Precautionary statement(s)
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.
S37/39 Wear suitable gloves and eye/face protection.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C12H25Br
Molecular Weight : 249,23 g/mol
Component Concentration
2-Bromododecane
CAS-No. 13187-99-0 -
EC-No. 236-142-7

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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, 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 breathing vapors, mist or gas. Ensure adequate ventilation.
Evacuate personnel to safe areas.
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 contact with skin and eyes. Avoid inhalation of vapour or mist.
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. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
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
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).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: liquid
Colour: colourless
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: -96 °C - lit.
point
f) Initial boiling point and 130 °C at 8 hPa - lit.
boiling range
g) Flash point 113 °C - closed cup
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 19,989 hPa at 20 °C
46,871 hPa at 55 °C
l) Vapour density no data available
m) Relative density 1,02 g/cm3 at 25 °C
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, Strong bases
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.
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

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-溴十二烷 在 三乙基硼 tri(2-furyl)germane 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.0h， 以99%的产率得到十二烷
  参考文献：
  名称：

  用 Tri-2-furylgermane 还原有机卤化物：化学计量和催化还原

  摘要：

  Tri-2-furylgermane 被证明是一种有效的有机卤化物自由基还原试剂。在催化量的三乙基硼烷存在下，在 25°C 下，在 THF 中用三-2-呋喃基锗烷处理 1-溴十二烷，几乎可以定量地得到十二烷。在相同的反应条件下，2-碘乙醛烯丙缩醛的自由基环化得到五元产物。这些反应在催化量的氢化锗存在下用 NaBH4 进行。该反应在水中以及在 THF 中进行，以良好的收率得到相应的还原化合物。

  DOI：

  10.1246/bcsj.74.747
• 作为产物：
  描述：

  1-十二烯十二碳烯α-十二碳烯α-十二碳烯 在 polystyrylmethylenehexadecyldibutylphosphonium bromide 氢溴酸 作用下， 反应 8.0h， 以89%的产率得到2-溴十二烷
  参考文献：
  名称：

  Khurana, Jitender M.; Tetenyi, Peter; Kodomari, Mitsuo, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 1129 - 1130

  摘要：

  DOI：

文献信息

• Triethylborane-Induced Radical Reactions with Gallium Hydride Reagent HGaCl₂
  作者：Satoshi Mikami、Kazuya Fujita、Tomoaki Nakamura、Hideki Yorimitsu、Hiroshi Shinokubo、Seijiro Matsubara、Koichiro Oshima

  DOI：10.1021/ol015904j

  日期：2001.6.1

  gallium hydride reagent, HGaCl2, was found to act as a radical mediator, like tributyltin hydride. Treatment of alkyl halides with the gallium hydride reagent, generated from gallium trichloride and sodium bis(2-methoxyethoxy)aluminum hydride, provided the corresponding reduced products in excellent yields. Radical cyclization of halo acetals was also successful with not only the stoichiometric gallium

  [请参阅反应]。发现氢化镓试剂HGaCl2像氢化三丁基锡一样起自由基介体的作用。用由三氯化镓和双（2-甲氧基乙氧基）铝氢化钠生成的氢化镓试剂处理卤代烷，可提供相应的还原产物，收率很高。不仅用化学计量的镓试剂而且用催化量的三氯化镓结合化学计量的氢化铝作为氢化物源，卤代乙缩醛的自由基环化也是成功的。
• Potential antiatherosclerotic agents. 4. [(Functionalized-alkyl)amino]benzoic acid analogs of cetaben
  作者：Vern G. DeVries、Elwood E. Largis、Thomas G. Miner、Robert G. Shepherd、Janis Upeslacis

  DOI：10.1021/jm00364a011

  日期：1983.10

  the alkyl group of cetaben is substituted with various functional groups or replaced entirely by a functionalized alkanoyl moiety is described. Also reported are the syntheses of branched-chain (alkylamino)benzoic acids in which branching is specifically localized at the terminus of the alkyl chain. Structure-activity relationships of these compounds, both as hypolipidemic agents and as inhibitors of

  描述了一系列类似物的合成，其中cetaben的烷基被各种官能团取代或完全被官能化的烷酰基部分取代。还报道了支链（烷基氨基）苯甲酸的合成，其中支化特别地位于烷基链的末端。讨论了这些化合物的结构活性关系，这些化合物既作为降血脂药，又作为脂肪酰基辅酶A：胆固醇酰基转移酶（ACAT）的抑制剂。专门合成了某些化合物以检验以下假设：位于Cetaben烷基链末端附近的基团可能会延迟分子的代谢降解，从而增强生物活性。发现其中一些（48-50）是合成的最活跃的类似物。
• Electron transfer-induced reduction of organic halides with amines
  作者：Takahide Fukuyama、Yuki Fujita、Hayato Miyoshi、Ilhyong Ryu、Shih-Chieh Kao、Yen-Ku Wu

  DOI：10.1039/c8cc02445f

  日期：——

  Reduction of a variety of organo halides was examined by using amines as a sacrificial hydrogen source. UV light-induced reduction of vinyl and aryl halides with triethylamine proceeded smoothly to give the corresponding reduced products. High temperature heating also caused the reduction and DABCO (1,4-diazabicyclo[2.2.2]octane) also served as a good reducing reagent.

  通过使用胺作为牺牲氢源，研究了各种有机卤化物的还原。UV光诱导的三乙胺对乙烯基卤化物和芳基卤化物的还原反应顺利进行，得到了相应的还原产物。高温加热也引起了还原，DABCO（1,4-二氮杂双环[2.2.2]辛烷）也用作良好的还原剂。
• Radical Reaction by a Combination of Phosphinic Acid and a Base in Aqueous Media
  作者：Hideki Yorimitsu、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1246/bcsj.74.225

  日期：2001.2

  Treatment of various organic halides with phosphinic acid (hypophosphorous acid) in aqueous ethanol in the presence of a radical initiator and a base gave the corresponding reduced products in high yields. Addition of a base is indispensable for the reduction of halides by phosphinic acid. Allylic ether of o-iodophenol or 2-haloalkanal allylic acetal underwent radical cyclization under the same conditions

  在自由基引发剂和碱的存在下，在乙醇水溶液中用次膦酸（次磷酸）处理各种有机卤化物，以高产率得到相应的还原产物。添加碱对于通过次膦酸还原卤化物是必不可少的。邻碘苯酚的烯丙醚或2-卤代烷醛烯丙缩醛在相同条件下进行自由基环化反应，得到相应的环状产物，收率极好。发现氘代次膦酸是有机卤化物自由基氘化的有效链载体。例如，将氘代次膦酸、碳酸钾、2,2'-偶氮双(异丁脒)二盐酸盐作为引发剂和对碘苯甲酸的氧化氘溶液加热回流，得到对氘苯甲酸，产率为94%。混合二恶烷/D2O 溶剂系统与 DBU 和过二硫酸钾相结合，对于以高产率和高氘掺入量氘化疏水底物至关重要。合作...
• Cobalt‐Catalyzed Cross‐Coupling Reaction between Functionalized Primary and Secondary Alkyl Halides and Aliphatic Grignard Reagents
  作者：Gérard Cahiez、Christophe Chaboche、Christophe Duplais、Arianna Giulliani、Alban Moyeux

  DOI：10.1002/adsc.200800166

  日期：2008.7.7

  The coupling of primary and secondary unactivated alkyl bromides with alkyl-Grignard reagents was performed in good yields under mild conditions by using a new catalytic system: consisting of cobalt chloride and tetramethylethylenediamine (CoCl2⋅2 LiI, 4 TMEDA). The reaction is very chemoselective since ketone, ester and nitrile functions are tolerated.

  由氯化钴和四甲基乙二胺（氯化钴：通过使用新催化体系在温和条件下良好的产率进行初级和次级未活化的烷基溴化物与烷基-格氏试剂的偶联2 ⋅2的LiI，4 TMEDA）。该反应具有很高的化学选择性，因为可以耐受酮，酯和腈的作用。

表征谱图