4-dimethylaminophenylamine dihydrochloride | 536-46-9

• 物质功能分类: 有机原料 - 氨基化合物 - 无环单胺、多胺及其衍生物和盐
• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-dimethylaminophenylamine dihydrochloride
• 英文别名: N,N-dimethyl-p-phenylene diamine dihydrochloride；4-dimethylaminoaniline dihydrochloride；p-(dimethylamino)aniline dihydrochloride；(4-aminophenyl)-dimethylazanium;chloride
• CAS: 536-46-9
• 化学式: C₈H₁₄N₂*2Cl
• 分子量: 209.119
• InChiKey: KTWNIUBGGFBRKH-UHFFFAOYSA-N

物化性质

• 熔点：
  222 °C (dec.)(lit.)
• 溶解度：
  2000g/l
• 稳定性/保质期：
  1. 暴露在空气中会变黑。
  2. 容易吸潮，吸入、口服或接触皮肤都有毒，大量使用时应穿戴适当的防护服。

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.3
• 氢给体数：
  2
• 氢受体数：
  2

ADMET

毒理性

• 副作用

神经毒素 - 其他中枢神经系统神经毒素

Neurotoxin - Other CNS neurotoxin

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

安全信息

• TSCA：
  Yes
• 危险等级：
  6.1
• 危险品标志：
  T
• 安全说明：
  S36/37,S45
• 危险类别码：
  R23/24/25
• WGK Germany：
  3
• 海关编码：
  2921590090
• 危险品运输编号：
  UN 2811 6.1/PG 2
• 危险类别：
  6.1
• RTECS号：
  ST1750000
• 包装等级：
  III
• 危险性防范说明：
  P261,P264,P280,P301+P310,P305+P351+P338,P311
• 危险性描述：
  H300,H311+H331,H319
• 储存条件：
  充氮气密封、避光和干燥保存，建议储存在-20℃的环境中。

SDS

Name:	N N-Dimethyl-P-Phenylenediamine Dihydrochloride 99% Material Safety Data Sheet
Synonym:	USAF EK-742
CAS:	536-46-9

Section 1 - Chemical Product MSDS Name:N N-Dimethyl-P-Phenylenediamine Dihydrochloride 99% Material Safety Data Sheet
Synonym:USAF EK-742

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
536-46-9	N,N-Dimethyl-p-Phenylenediamine Dihydr	99	208-635-7

Hazard Symbols: T
Risk Phrases: 23/24/25

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Toxic by inhalation, in contact with skin and if swallowed.Hygroscopic (absorbs moisture from the air).Light sensitive.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation. The toxicological properties of this material have not been fully investigated.
Skin:
May cause skin irritation. The toxicological properties of this material have not been fully investigated.
Ingestion:
May cause digestive tract disturbances. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

---

Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid immediately. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Wash clothing before reuse.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Notes to Physician:

---

Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Do NOT get water inside containers. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions.
Provide ventilation. Do not get water inside containers.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Wash hands before eating. Use only in a well-ventilated area. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation. Store protected from light.
Do not allow contact with water. Wash clothing before reuse.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Store protected from moisture. Store protected from light.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 536-46-9: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Chunks
Color: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 222 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: N/A
Explosion Limits, upper: N/A
Decomposition Temperature:
Solubility in water: freely soluble
Specific Gravity/Density:
Molecular Formula: C8H12N2.2HCl
Molecular Weight: 209.12

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, light, moisture.
Incompatibilities with Other Materials:
Strong oxidizing agents, acids, acid chlorides, acid anhydrides.
Hazardous Decomposition Products:
Hydrogen chloride, nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 536-46-9: ST1300000 LD50/LC50:
Not available.
Carcinogenicity:
N,N-Dimethyl-p-Phenylenediamine Dihydrochloride - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2811
Packing Group: II
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: II
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: II

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T
Risk Phrases:
R 23/24/25 Toxic by inhalation, in contact with skin
and if swallowed.
Safety Phrases:
S 28A After contact with skin, wash immediately with
plenty of water.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 536-46-9: No information available.
Canada
CAS# 536-46-9 is listed on Canada's DSL List.
CAS# 536-46-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 536-46-9 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

简介

N,N-二甲基对苯二胺盐酸盐是一种白至灰白色的结晶性粉末，易吸湿。遇光及氧气逐渐变色。其熔点为199℃，易溶于水、乙醇、苯和三氯甲烷中，微溶于乙醚。与有机过氧化物反应可产生紫红色产物。

制备

一种N,N-二甲基对苯二胺盐酸盐的制备方法包括以下步骤：

1. 取1摩尔对硝基氯苯溶解于400ml甲苯中，得溶液A。
2. 取1.1摩尔二甲胺盐酸盐溶解于180ml水中，加入上述溶液A中。
3. 在20～25℃下搅拌，滴加1.1摩尔15％氢氧化钠水溶液。升温至35℃后，在30分钟内再滴加0.66摩尔15％氢氧化钠水溶液，然后保温反应60分钟。
4. 静置、分相，甲苯层加入活性镍催化剂并进行加氢还原。
5. 过滤分离催化剂。甲苯层通入氯化氢气体，得到N,N-二甲基对苯二胺二盐酸盐沉淀。
6. 离心后，获得纯度为99.7％、收率为94.5％(以对硝基氯苯计)的N,N-二甲基对苯二胺二盐酸盐198g。

用途

该物质主要用于分析试剂。具体应用包括：

• 用于硫化氢和硫化物的比色测定及钒的检测。
• 用于检验和比色测定硫化氢、硫化物，在酸性溶液中能与氧化剂作用形成红色，适用于铬酸盐滴定钡盐时作为指示剂。
• 用于测定钒；以显色反应检验氧化剂；检定空气中氯、溴、锰及臭氧（试纸）。
• 在显微分析中检验氧化酶；用于检验丙酮、尿酸、铊盐等。

反应信息

• 作为反应物：
  描述：

  4-dimethylaminophenylamine dihydrochloride 在 iron(III) chloride 、 谷胱甘肽 、 zinc diacetate 、 sodium acetate 作用下， 以 水 为溶剂， 生成 亚甲兰
  参考文献：
  名称：

  H2S 和 NIR 光驱动纳米马达通过增强肿瘤代谢共生的破坏来诱导双硫下垂以进行靶向抗癌治疗

  摘要：

  二硫下垂是一种通过破坏肿瘤代谢共生 （TMS） 而引起的程序性细胞死亡的新机制，在癌症治疗中显示出巨大的潜力。然而，双硫下垂的疗效受到实体瘤中药物渗透性差的限制。在此，已经构建了硫化氢 （H2S） 和近红外 （NIR） 光驱动纳米马达 （表示为 HGPP） 以有效穿透肿瘤并诱导二硫下垂。HGPP 证明谷胱甘肽 （GSH） 反应性释放 H2S，它与 NIR 光诱导的光热效应相结合，驱动 HGPP 运动以促进肿瘤深部渗透。释放的 H2S 会诱导肿瘤酸中毒并破坏 TMS，其中细胞饥饿后的二硫键积累导致二硫下垂。此外，HGPP 诱导肝癌特异性细胞摄取并催化葡萄糖和氧气转化产生过氧化氢 （H2O2），导致葡萄糖饥饿。总体而言，本研究开发了一种多功能 Janus 纳米马达，为基于双硫线下垂的实体瘤治疗提供了一种新策略。

  DOI：

  10.1016/j.cclet.2024.110314
• 作为产物：
  描述：

  methyl red 在 铁粉 、 氯化铵 作用下， 以 乙醇 、 水 为溶剂， 反应 0.25h， 以85%的产率得到4-dimethylaminophenylamine dihydrochloride
  参考文献：
  名称：

  A Simple Reduction Method of Azo-Compounds to Amines Using Fe Powder in the Presence of NH4Cl

  摘要：

  A series of azo-compounds were reduced to related aromatic amines in the presence of Fe powder and ammonium chloride. This one step protocol led to the formation of products in middle to high yields, especially when electron releasing substituted aromatic azo-compounds were reduced.

  DOI：

  10.1007/s00706-007-0633-2
• 作为试剂：
  描述：