3,5-二甲基-1,2-苯二胺 | 3171-46-8

• 物质功能分类: 有机原料 - 氨基化合物 - 环烷胺、芳香单胺、芳香多胺及其衍生物和盐
• 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: 3,5-二甲基-1,2-苯二胺
• 中文别名: 4,5-二甲基-1,2-苯二胺
• 英文名称: 3,5-dimethylbenzene-1,2-diamine
• 英文别名: 3,5-dimethyl-1,2-phenylenediamine；1,2-diamino-3,5-dimethylbenzene；3,5-Dimethyl-o-phenylendiamin；3,5-dimethyl-1,2-diamino-benzene
• CAS: 3171-46-8
• 化学式: C₈H₁₂N₂
• mdl: MFCD00972722
• 分子量: 136.197
• InChiKey: DMEPVFSJYHJGCD-UHFFFAOYSA-N

物化性质

• 熔点：
  73-78℃
• 沸点：
  272.1±35.0 °C(Predicted)
• 密度：
  1.076±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2921590090
• WGK Germany：
  3
• 危险标志：
  GHS07
• 危险性描述：
  H302,H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338
• 储存条件：
  2-8°C

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 1,2-Diamino-3,5-dimethylbenzene
CAS-No. : 3171-46-8
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 [EU-GHS/CLP]
Acute toxicity, Oral (Category 4)
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
Harmful if swallowed. Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust.
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)
R22 Harmful if swallowed.
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.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : 3,5-Dimethyl-1,2-phenylenediamine
Formula : C8H12N2
Molecular Weight : 136,19 g/mol
Component Concentration
1,2-Diamino-3,5-dimethylbenzene
CAS-No. 3171-46-8 -

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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, nitrogen oxides (NOx)
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. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
Do not let product enter drains.
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.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: 2 - 8 °C
Handle under nitrogen, protect from moisture. Store under nitrogen.
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: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing 73 - 78 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point not applicable
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- log Pow: 1,535
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 acids and 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
Prolonged or repeated exposure may cause allergic reactions in certain sensitive individuals.
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. Causes respiratory tract irritation.
Ingestion 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. 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: - 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
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3,5-二甲基-1,2-苯二胺 在 亚硝酸特丁酯 作用下， 以 乙腈 为溶剂， 反应 0.25h， 以95%的产率得到4,6-dimethyl-1H-benzo[d][1,2,3]triazole
  参考文献：
  名称：

  亚硝酸叔丁酯介导的氮转移反应：室温下苯并三唑和叠氮化物的合成

  摘要：

  的A转换ö苯二胺为苯并三唑类是用在室温下实现叔丁基亚硝酸盐。优化的条件也非常适合将磺酰基和酰基肼转化为相应的叠氮化物。该协议不需要任何催化剂或酸性介质。在短时间内以优异的产率获得了所需的产物。

  DOI：

  10.1039/c8ob01950a
• 作为产物：
  描述：

  5-硝基间二甲苯 在 硫酸 、 5%-palladium/activated carbon 、 氢气 、 硝酸 作用下， 以 甲醇 为溶剂， -10.0~60.0 ℃ 、500.01 kPa 条件下， 反应 9.0h， 生成 3,5-二甲基-1,2-苯二胺
  参考文献：
  名称：

  2-正丙基-4-甲基苯并咪唑-6-羧酸的合成方 法

  摘要：

  本发明涉及一种2‑正丙基‑4‑甲基苯并咪唑‑6‑羧酸的合成方法。3,5‑二甲基硝基苯经硝酸/浓硫酸硝化反应，生成中间产物Ⅱ 3,5‑二甲基‑1,2‑二硝基苯；中间产物Ⅱ在乙醇溶液中，Pd/C催化氢化反应，得中间产物Ⅲ 3,5‑二甲基‑1,2‑苯二胺；中间产物Ⅲ在多聚磷酸溶液中，与正丁酸反应，得到中间产物Ⅳ 2‑正丙基‑4，6‑二甲基苯并咪唑；中间产物Ⅳ在醋酸溶液中，经钴盐空气液相氧化反应，得产物V 2‑正丙基‑4‑甲基苯并咪唑‑6‑羧酸。本发明操作简单，原料易得，所用溶剂均能回收套用，产品含量可达95％以上，收率高达73.2％，污染少，适合于工业化生产。

  公开号：

  CN107118161B

文献信息

• THE CONDENSATION OF PHOSPHONOTHIOIC AND PHOSPHONIC DICHLORIDES WITH <i>o</i>-DIAMINES
  作者：Ralph L. Dannley、Arturs Grava

  DOI：10.1139/v65-469

  日期：1965.12.1

  dichlorides, and phenylenediamines containing electron-donating substituents are more reactive than those containing electron-withdrawing substituents. The diazaphosphole 2-oxides undergo hydrolysis or alcoholysis of only one of the amide groups under mild conditions. The 2-sulfides are much more resistant to hydrolysis than the 2-oxides. The 2-sulfides are converted to the N-methyl derivatives by dimethyl

  已经制备了一系列 2,3-二氢-1H-1,3,2-苯并二氮杂磷 2-硫化物和 2-氧化物，最常见的方法是在回流惰性溶剂中将二胺与膦硫代或膦酰二氯化物缩合。硫代膦酰二氯化物比相应的膦酰二氯反应更慢，含有给电子取代基的苯二胺比含有吸电子取代基的苯二胺反应性更强。二氮杂磷酰 2-氧化物在温和条件下仅对其中一个酰胺基进行水解或醇解。2-硫化物比2-氧化物更耐水解。2-硫化物被硫酸二甲酯和碱转化为N-甲基衍生物。2-氧化物在这些条件下水解。
• Ru@PsIL-Catalyzed Synthesis of <i>N</i> -Formamides and Benzimidazole by using Carbon Dioxide and Dimethylamine Borane
  作者：Vitthal B. Saptal、Takehiko Sasaki、Bhalchandra M. Bhanage

  DOI：10.1002/cctc.201800185

  日期：2018.6.21

  This work reports the synthesis and characterization of ruthenium nanoparticles (Ru NPs) supported on polymeric ionic liquids (PILs). This catalyst shows high catalytic activity towards the N‐formylation of amines and synthesis of benzimidazoles from 1,2‐diamines and carbon dioxide (CO2) by reductive dehydrogenation of dimethylamine borane. This methodology shows excellent functional group tolerance

  这项工作报告了载于聚合物离子液体（PIL）上的钌纳米颗粒（Ru NPs）的合成和表征。该催化剂对胺的N-甲酰化和由1,2-二胺和二氧化碳（CO 2）通过二甲胺硼烷的还原脱氢合成苯并咪唑具有很高的催化活性。该方法显示出优异的官能团耐受性，在合成N-甲酰胺和苯并咪唑的过程中具有广泛的底物范围。有趣的是，该协议还提供了串联减少2-硝基胺和CO 2的方法。合成苯并咪唑 提出了聚合物的离子液相起关键作用，例如帮助静电稳定纳米颗粒，提供离子环境并控制底物/试剂易于接近活性位。开发的方法利用CO 2作为C 1源和水/乙醇作为绿色溶剂系统。另外，发现该催化剂本质上是可再循环的，并且显示出连续五次循环运行而其活性没有明显损失。
• Visible light promoted tandem dehydrogenation-deaminative cyclocondensation under aerobic conditions for the synthesis of 2-aryl benzimidazoles/quinoxalines from <i>ortho</i>-phenylenediamines and arylmethyl/ethyl amines
  作者：Firdoos Ahmad Sofi、Rohit Sharma、Ravi Rawat、Asit K. Chakraborti、Prasad V. Bharatam

  DOI：10.1039/d0nj03002c

  日期：——

  Visible light promoted domino synthesis of 2-aryl benzimidazoles is reported through the reaction of ortho-phenylenediamines and arylmethyl amines under aerobic conditions. The methodology has wide substrate scope and tolerates a wide range of functional groups affording the products in high yields. The use of arylethyl amines instead of arylmethyl amines gives 2-aryl quinoxalines.

  据报道，通过有氧条件下邻苯二胺与芳基甲基胺的反应，可见光促进了2-芳基苯并咪唑的多米诺骨牌合成。该方法具有广泛的底物范围，并且可以耐受多种官能团，从而以高收率提供了产品。使用芳基乙基胺代替芳基甲基胺得到2-芳基喹喔啉。
• Heterocyclic compounds as inhibitors of factor VIIa
  申请人：Glunz W. Peter

  公开号：US20060211720A1

  公开（公告）日：2006-09-21

  The present invention relates generally to compounds that inhibit serine proteases. In particular it is directed to novel heterocyclic compounds, or a stereoisomer or pharmaceutically acceptable salt, solvate, or prodrug form thereof, which are useful as selective inhibitors of serine protease enzymes of the coagulation cascade; for example thrombin, factor VIIa, factor Xa, factor XIa, factor IXa, and/or plasma kallikrein. In particular, it relates to compounds that are factor VIIa inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds and methods of using the same.

  本发明一般涉及抑制丝氨酸蛋白酶的化合物。具体而言，它涉及新颖的杂环化合物，或其立体异构体或药用可接受的盐、溶剂合物或前药形式，这些化合物可用作凝血级联中丝氨酸蛋白酶的选择性抑制剂；例如凝血酶、第VIIa因子、第Xa因子、第XIa因子、第IXa因子和/或血浆激肽。具体而言，它涉及第VIIa因子抑制剂的化合物。本发明还涉及包含这些化合物的药物组合物以及使用它们的方法。
• Synthesis of substituted phenanthrene-9-benzimidazole conjugates: Cytotoxicity evaluation and apoptosis inducing studies
  作者：Niggula Praveen Kumar、Pankaj Sharma、S. Sujana Kumari、Umarani Brahma、Shalini Nekkanti、Nagula Shankaraiah、Ahmed Kamal

  DOI：10.1016/j.ejmech.2017.09.006

  日期：2017.11

  aldehydes with various substituted o-phenylenediamines. The title compounds were evaluated for their in vitro cytotoxic potential against various human cancer cell lines like breast (BT-549), prostate (PC-3 and DU145), triple negative breast cancer (MDA-MB-453), and human colon cancer (HCT-116 and HCT-15) cells. Among the tested compounds, 10o displayed significant in vitro cytotoxic activity against PC-3

  通过将菲醛与各种取代的邻苯二胺缩合，合成了一系列新的菲-9-苯并咪唑共轭物。评价了标题化合物对各种人类癌细胞系（如乳腺癌（BT-549），前列腺癌（PC-3和DU145），三阴性乳腺癌（MDA-MB-453）和人类结肠癌）的体外细胞毒性潜力（HCT-116和HCT-15）细胞。在被测试的化合物中，10o以IC 50表现出对PC-3前列腺癌细胞的显着体外细胞毒活性。值为6.32±0.09μM。此外，细胞周期分析表明它以剂量依赖性方式阻断细胞周期的G2 / M期。为了确定化合物10o对细胞活力的影响；进行了相差显微镜，AO / EB染色，DAPI染色和DCFDA染色研究。在这些研究中，清楚地观察到凋亡特征，表明该化合物通过凋亡抑制细胞增殖。JC-1染色和膜联蛋白结合试验表明PC-3细胞凋亡的程度。此外，相对粘度测量和分子对接研究表明这些化合物通过嵌入与DNA结合。