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

---

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.

---

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.

---

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

---

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

---

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.

---

Section 12 - ECOLOGICAL INFORMATION

---

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

---

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

---

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.

---

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：

  N,N-二甲基-对苯二胺 、 alkaline earth salt of/the/ methylsulfuric acid 在 乙醇 、 4-dimethylaminophenylamine dihydrochloride 作用下， 生成 N,N-dimethyl-N'-(5-nitro-[2]pyridyl)-p-phenylenediamine
  参考文献：
  名称：

  Mangini; Colonna, Gazzetta Chimica Italiana, 1943, vol. 73, p. 323,327

  摘要：

  DOI：

文献信息

• Substituted phenyl piperazinyl pyrrolidin-2-ones and related compounds
  申请人：Rhone-Poulenc Sante

  公开号：US04547504A1

  公开（公告）日：1985-10-15

  Pyrrolidine derivatives of the formula: ##STR1## wherein X represents an oxygen or sulphur atom, R represents a hydrogen atom or an alkyl radical, R.sub.o represents a hydrogen atom, an alkyl radical or a phenyl radical optionally substituted by a halogen atom or by an alkyl, alkoxy, alkylthio or nitro radical, A represents a nitrogen atom or a radical .dbd.CH--, the symbol Y represents a hydrogen or halogen atom or an alkyl, alkoxy, alkylthio, alkylcarbonyl, nitro, amino, alkylcarbonylamino, alkylamino, dialkylamino, alkylsulphinyl, alkylsulphonyl, alkoxycarbonyl, cyano, trifluoromethyl, hydroxy, mercapto, alkylcarbonyloxy or alkylcarbonylthio radical, n represents zero or 1, and p represents 1, 2 or 3, it being understood that the alkyl and alkoxy radicals, and alkyl and alkoxy moieties of any of the aforementioned groups, contain from 1 to 4 carbon atoms are new therapeutically useful compounds, more particularly useful as antidepressants.

  吡咯烷衍生物的化学式为：##STR1## 其中X代表氧或硫原子，R代表氢原子或烷基基团，R.sub.o代表氢原子、烷基基团或苯基基团，该苯基基团可以选择性地被卤原子、烷基、烷氧基、烷硫基或硝基基团取代，A代表氮原子或.dbd.CH--基团，符号Y代表氢或卤原子或烷基、烷氧基、烷硫基、烷羰基、硝基、氨基、烷羰胺基、烷基氨基、二烷基氨基、烷基砜基、烷基砜酰基、烷氧羰基、氰基、三氟甲基、羟基、巯基、烷基羰氧基或烷基羰硫基基团，n代表零或1，p代表1、2或3，其中烷基和烷氧基基团以及任何上述基团的烷基和烷氧基部分含有1至4个碳原子，是新的具有治疗用途的化合物，特别适用作抗抑郁药。
• Substituted 3-cyano quinolines
  申请人：American Cyanamid Company

  公开号：US06002008A1

  公开（公告）日：1999-12-14

  This invention provides compounds having the formula: ##STR1## wherein: X is cycloalkyl which may be optionally substituted; or is a pyridinyl, pyrimidinyl, or phenyl ring; wherein the pyridinyl, pyrimidinyl, or phenyl ring may be optionally substituted; n is 0-1; Y is --NH--, --O--, --S--, or --NR--; R is alkyl of 1-6 carbon atoms; R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are each, independently, hydrogen, halogen, alkyl, alkenyl, alkynyl, alkenyloxy, alkynyloxy, hydroxymethyl, halomethyl, alkanoyloxy, alkenoyloxy, alkynoyloxy, alkanoyloxymethyl, alkenoyloxymethyl, alkynoyloxymethyl, alkoxymethyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylsulfonamido, alkenylsulfonamido, alkynylsulfonamido, hydroxy, trifluoromethyl, cyano, nitro, carboxy, carboalkoxy, carboalkyl, phenoxy, phenyl, thiophenoxy, benzyl, amino, hydroxyamino, alkoxyamino, alkylamino, dialkylamino, aminoalkyl, N-alkylaminoalkyl, N,N-dialkylaminoalkyl, phenylamino, benzylamino, ##STR2## R.sub.5 is alkyl which may be optionally substituted, or phenyl which may be optionally substituted; R.sub.6 is hydrogen, alkyl, or alkenyl; R.sub.7 is chloro or bromo R.sub.8 is hydrogen, alkyl, aminoalkyl, N-alkylaminoalkyl, N,N-dialkylaminoalkyl, N-cycloalkylaminoalkyl, N-cycloalkyl-N-alkylaminoalkyl, N,N-dicycloalkylaminoalkyl, morpholino-N-alkyl, piperidino-N-alkyl, N-alkyl-piperidino-N-alkyl, azacycloalkyl-N-alkyl, hydroxyalkyl, alkoxyalkyl, carboxy, carboalkoxy, phenyl, carboalkyl+, chloro, fluoro, or bromo; Z is amino, hydroxy, alkoxy, alkylamino, dialkylamino, morpholino, piperazino, N-alkylpiperazino, or pyrrolidino; m=1-4,q=1-3, and p=0-3; any of the substituents R.sub.1, R.sub.2, R.sub.3, or R.sub.4 that are located on contiguous carbon atoms can together be the divalent radical --O--C(R.sub.8).sub.2 --O--; or a pharmaceutically acceptable salt thereof with the proviso that when Y is --NH--, R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are hydrogen, and n is 0, X is not 2-methylphenyl, which are inhibitors of protein tyrosine kinase.

  这项发明提供了具有以下结构的化合物：##STR1## 其中：X是环烷基，可以选择性地被取代；或者是吡啶基、嘧啶基或苯环；其中吡啶基、嘧啶基或苯环可以选择性地被取代；n为0-1；Y为--NH--、--O--、--S--或--NR--；R为1-6个碳原子的烷基；R.sub.1、R.sub.2、R.sub.3和R.sub.4分别独立地是氢、卤素、烷基、烯基、炔基、烯氧基、炔氧基、羟甲基、卤甲基、烷酰氧基、烯酰氧基、炔酰氧基、烷酰氧甲基、烯酰氧甲基、炔酰氧甲基、烷氧甲基、烷氧基、烷基硫、烷基亚砜基、烷基磺酰基、烷基磺酰胺基、烯基磺酰胺基、炔基磺酰胺基、羟基、三氟甲基、氰基、硝基、羧基、羧基烷氧基、羧基烷基、苯氧基、苯基、噻吩氧基、苄基、氨基、羟氨基、烷氧氨基、烷基氨基、二烷基氨基、氨基烷基、N-烷基氨基烷基、N,N-二烷基氨基烷基、苯基氨基、苄氨基、##STR2## R.sub.5是可以选择性取代的烷基，或者是可以选择性取代的苯基；R.sub.6是氢、烷基或烯基；R.sub.7是氯或溴；R.sub.8是氢、烷基、氨基烷基、N-烷基氨基烷基、N,N-二烷基氨基烷基、N-环烷基氨基烷基、N-环烷基-N-烷基氨基烷基、N,N-二环烷基氨基烷基、吗啉-N-烷基、哌啶-N-烷基、N-烷基-哌啶-N-烷基、氮杂环烷基-N-烷基、羟基烷基、烷氧基烷基、羧基、羧基烷氧基、苯基、羧基+、氯、氟或溴；Z是氨基、羟基、烷氧基、烷基氨基、二烷基氨基、吗啉基、哌嗪基、N-烷基哌嗪基或吡咯烷基；m=1-4，q=1-3，p=0-3；任何位于相邻碳原子上的R.sub.1、R.sub.2、R.sub.3或R.sub.4取代基可以共同形成二价基团--O--C(R.sub.8).sub.2 --O--；或其药学上可接受的盐，但当Y为--NH--时，R.sub.1、R.sub.2、R.sub.3和R.sub.4为氢，n为0时，X不是2-甲基苯基，这些化合物是蛋白酪氨酸激酶的抑制剂。
• Method of treating or inhibiting colonic polyps
  申请人：American Cyanamid Company

  公开号：US06384051B1

  公开（公告）日：2002-05-07

  This invention provides a method of treating or inhibiting colonic polyps which comprises providing a compound of formula 1 wherein: R1, R2, R3, R4, X, Y, and n are as defined hereinbefore, or a pharmaceutically acceptable salt thereof.

  本发明提供了一种治疗或抑制结肠息肉的方法，包括提供如下公式1的化合物： 其中： R1、R2、R3、R4、X、Y和n如前文所定义，或其药用可接受的盐。
• Fused imidazoheterocyclic compounds and pharmaceutical compositions
  申请人：A. H. Robins Company, Inc.

  公开号：US04772600A1

  公开（公告）日：1988-09-20

  Imidazoheterocyclic compounds having the formula: ##STR1## wherein the A ring is pyridine in any of its four positions; B is carbonyl, thioxomethyl or hydroxymethylene; Z is hydrogen, halogen, loweralkyl, hydroxy, loweralkoxy, diloweralkylamino or nitro; Ar is phenyl, pyrido, thienyl or furanyl; and W forms a wide combination of groups with B, including acids, esters, alcohols, amides and ketones. The compounds have CNS activity in a method for treating a living animal body as muscle relaxants, anticonvulsants and antianxiety agents.

  咪唑杂环化合物的化学式为：##STR1## 其中A环是吡啶的四个位置中的任意一个；B是羰基、硫代甲基或羟甲基；Z是氢、卤素、较低烷基、羟基、较低烷氧基、二较低烷基氨基或硝基；Ar是苯基、吡啶基、噻吩基或呋喃基；W与B形成多种组合，包括酸、酯、醇、酰胺和酮。这些化合物在治疗活体动物身体的方法中具有中枢神经系统活性，可用作肌肉松弛剂、抗惊厥剂和抗焦虑剂。
• Regioselective Covalent Modification of Hemoglobin in Search of Antisickling Agents
  作者：Soobong Park、Brittany L. Hayes、Fatima Marankan、Debbie C. Mulhearn、Linda Wanna、Andrew D. Mesecar、Bernard D. Santarsiero、Michael E. Johnson、Duane L. Venton

  DOI：10.1021/jm020361k

  日期：2003.3.1

  the resulting increase in solubility of the modified hemoglobin. Depending on the attached R-group, the isothiocyanates were found to react either with the Cysbeta93 or the N-terminal amine of the alpha-chain. One of the most effective compounds in the series, 2-(N,N-dimethylamino)ethyl isothiocyanate, selectively reacts with the thiol of Cysbeta93 which, in conjunction with the cationic group, was seen

  尽管镰状血红蛋白产生镰状细胞疾病的分子缺陷已经知道了数十年，但仍然没有有效的药物治疗作用于血红蛋白本身。在这项工作中，检查了一系列不同取代的异硫氰酸盐（R-NCS）与血红蛋白的区域选择性反应，试图改变镰刀型血红蛋白的溶解性。电喷雾质谱，分子建模，X射线晶体学和常规蛋白质化学用于研究这种区域选择性以及由此产生的修饰血红蛋白溶解度的增加。取决于所连接的R基团，发现异硫氰酸酯与Cysbeta93或α链的N端胺反应。该系列中最有效的化合物之一，2-（N，N-二甲基氨基）乙基异硫氰酸酯，与Cysbeta93的巯基发生选择性反应，后者与阳离子基团一起干扰了局部的血红蛋白结构。这种改性的HbS在完全脱氧状态下显示出约30％的溶解度增加，同时氧亲和力也显着增加。该化合物和相关的类似物似乎很容易穿过红细胞膜。讨论了这些结构变化与抑制胶凝的关系。增强HbS氧亲和力并直接抑制脱氧HbS聚合的双重活性，以及​​易