N-乙基-N-氯乙基苯胺 | 92-49-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-乙基-N-氯乙基苯胺
• 中文别名: N-氯乙烷-N-乙基苯胺；N-(2-氯乙基)-N-乙基苯胺
• 英文名称: N-ethyl-N-(2-chloroethyl)aniline
• 英文别名: N-(2-chloroethyl)-N-ethylaniline
• CAS: 92-49-9
• 化学式: C₁₀H₁₄ClN
• 分子量: 183.681
• InChiKey: DBDNQNARCHWMSP-UHFFFAOYSA-N

物化性质

• 熔点：
  46°C
• 沸点：
  302.39°C (rough estimate)
• 密度：
  1.0821 (rough estimate)
• 颜色/状态：
  NEEDLES FROM ALCOHOL
• 溶解度：
  SOL IN HOT ALCOHOL
• 分解：
  When heated to decomposition it emits toxic vapors of /Nitrogen Oxides and Hydrogen Chloride/.

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

代谢

N-乙基-N-(2-氯乙基)苯胺是微体悬浮液中烷氧基苯胺芥的代谢物。

N-ETHYL-N-(2-CHLOROETHYL)ANILINE IS A METABOLITE OF ALKOXYANILINE MUSTARDS IN MICROSOMAL SUSPENSIONS.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

Dermatotoxin - 皮肤烧伤。

Dermatotoxin - Skin burns.

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

毒理性

• 非人类毒性摘录

乙基苯基-2-氯乙胺，一种单功能芥末，在大鼠体内对沃克癌259进行了测试，发现无效。

ETHYLPHENYL-2-CHLOROETHYLAMINE, A MONOFUNCTIONAL MUSTARD WAS TESTED IN VIVO AGAINST WALKER CARCINOMA 259 IN RATS AND FOUND TO BE INACTIVE.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

经腹腔和皮肤接触途径有毒。经口摄入则有中等毒性。

Poison by intraperitoneal and skin contact routes. Moderately toxic by ingestion.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• TSCA 测试提交

N-(2-氯乙基)-N-乙基苯胺在4组各4只新西兰白兔（性别未指明）上进行急性皮肤毒性评估，测试物质以0.100、0.215、0.464和1.00 ml/kg体重的剂量涂敷于腹部皮肤，在闭合条件下。每组中有2只兔子的皮肤在涂抹测试物质前被磨伤。动物在处理后观察了14天。没有报告使用对照组。死亡率包括0.215 ml/kg和0.464 ml/kg水平各有一只，以及1.00 ml/kg水平有4只。通过移动平均法确定的LD50（及其95%置信区间）为464 ml/kg（0.270 - 0.799）。临床体征包括在0.100和0.215水平出现抑郁和鼻涕；在0.215 ml/kg水平出现弓背姿势、消瘦和半闭眼。在0.464 ml/kg水平观察到的额外体征包括喘息、腹泻、过度流涎、过度活跃和异常蓝眼。单个高剂量兔子在观察期间幸存下来，显示出额外的体征，包括抑郁的翻正和定位反射以及呼吸困难。所有处理组都看到了皮肤刺激的迹象。对死亡兔子进行大体尸检，在所有水平上发现充血的肺；在两个最高剂量水平上发现充血的肾脏；在最高剂量水平上发现自溶、苍白的肝脏和一触即破的胃。

N-(2-chloroethyl)-N-ethylaniline was evaluated for acute dermal toxicity in 4 groups of 4 New Zealand White rabbits (sex not indicated) administered 0.100, 0.215, 0.464, and 1.00 ml/kg bw doses of the test substance to the abdominal skin under occlusive conditions. The skin of 2 rabbits in each group was abraded prior to application of the test substance. Animals were observed for 14 days following treatment. The use of controls was not reported. Mortalities included one at both the 0.215 ml/kg and 0.464 ml/kg levels, and 4 at the 1.00 ml/kg level. The LD50 (and 95% confidence limits) were determined by the moving average method to be 464 ml/kg (0.270 - 0.799). Clinical signs included depression and nasal discharge at the 0.100 and 0.215 levels; hunched posture, emaciation, and half closed eyes at the 0.215 l ml/kg level. Additional signs observed at 0.464 ml/kg level included wheezing, diarrhea, excessive salivation, hyperactivity, and exceptionally blue eyes. The single high dose rabbit that survived long enough for observation displayed the additional signs of depressed righting and placement reflexes and labored respiration. Signs of dermal irritation were seen in all treatment groups. Gross necropsy of rabbits that died revealed congested lungs at all levels; congested kidneys at the two highest dose levels; and autolysis, pale livers and stomachs which fell apart when handled at the highest dose.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• TSCA 测试提交

N-(2-氯乙基)-N-乙基苯胺（CAS # 92-49-9）在4只雄性白兔（未指明品种）中评估了急性皮肤毒性，这些兔子在封闭条件下以200毫克/千克体重的剂量水平暴露于测试物质24小时。在应用测试物质之前，2只兔子的皮肤被磨伤。没有报告使用对照组。所有动物在24小时内死亡。未确定LD50，也未报告临床体征。大体尸检显示胸腔和腹部的器官正常。

N-(2-chloroethyl)-N-ethylaniline ( CAS # 92-49-9) was evaluated for acute dermal toxicity in 4 male albino rabbits (strain not indicated) exposed to the test substance under occlusive conditions at a dose level of 200 mg/kg body weight for 24 hours. The skin of 2 rabbits was abraded prior to application of the test substance. The use of controls was not reported. All animals died within 24 hrs. No LD50 was determined and no clinical signs were reported. Gross necropsy revealed organs of the thorax and abdomen to be normal.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• WGK Germany：
  3
• 海关编码：
  2921420090
• 包装等级：
  III
• 危险类别：
  6.1
• 安全说明：
  S20/21,S28,S45,S60,S61
• 危险品运输编号：
  UN 3283 6.1/PG 2

制备方法与用途

用途：用作有机合成的中间体。

反应信息

• 作为反应物：
  描述：

  N-乙基-N-氯乙基苯胺 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 54.0h， 生成 N-ethyl-N-(2-(4-methoxyphenoxy)ethyl)aniline
  参考文献：
  名称：

  氧化激活的DNA修饰剂可选择性产生细胞毒性

  摘要：

  DNA修饰剂是化疗癌症治疗的坚强后盾，但需要进行重大设计改进，以提高选择性，最大程度降低副作用，并使它们继续广泛使用。本文中，我们提出了一种新颖的设计策略，其中DNA修饰剂包含可氧化的离去基团和氮芥。这些试剂特别是在氧化时形成强亲电试剂。通过水解测得的活化表明，氧化剂可将反应活性提高1700倍。在2'-脱氧鸟苷存在下的反应会导致病变的形成。在HeLa细胞中测得的细胞毒性表明IC 50较低值需要可氧化的氢醌和氮芥子片段。在15种癌细胞系中的细胞毒性测量结果表明，氧化激活的DNA修饰剂具有高度选择性，因为测试的类似物对15种癌细胞系中只有3种的IC 50值小于10μM。相反，顺铂对15个细胞系中的13个具有高度毒性。氧化激活的DNA损伤剂的选择性细胞毒性可能对肾癌细胞有用，因为786-O细胞系模型测定的IC 50值为5μM。

  DOI：

  10.1002/cmdc.201100014
• 作为产物：
  描述：

  N-乙基-N-羟乙基苯胺 在 三氯氧磷 作用下， 反应 1.0h， 以83%的产率得到N-乙基-N-氯乙基苯胺
  参考文献：
  名称：

  通过AB 2单体的偶氮偶联反应和后聚合改性合成超支化的偶氮聚合物

  摘要：

  通过两步偶氮偶合反应合成了一系列的超支化偶氮聚合物，其中，通过偶氮偶合反应使AB 2单体逐步增长聚合，制备了超支化前体偶氮聚合物（HPAP）。通过在外围基团上的后聚合偶氮偶联反应进一步改性。由N-乙基-N-（2-氯乙基）苯胺与3,5-双（羧基）之间的亲核取代反应合成AB 2单体二[2-（N-乙基苯胺基）乙基] -5-氨基间苯二甲酸酯苯胺。在单体的基础上，通过AB 2的重氮盐的逐步增长缩聚反应制备HPAP。单体。然后将超支化前体聚合物与4-硝基苯胺，4-氨基苯甲酸和4-氨基苄腈的重氮盐反应，在周边位置引入不同类型的供体-受体偶氮-发色团。通过光谱方法和热分析表征了偶氮聚合物的结构和性质。通过将旋涂的聚合物薄膜暴露于中等强度（150 mW / cm 2的Ar +激光束）的干涉图样中，将超支化偶氮聚合物用于制造表面起伏光栅（SRG）。）。末端偶氮苯单元对位的吸电子基团的类型对SRG的铭刻率显示出

  DOI：

  10.1021/ma0511393

文献信息

• Water-soluble, deep-red fluorescent squaraine rotaxanes
  作者：Erin L. Cole、Easwaran Arunkumar、Shuzhang Xiao、Bryan A. Smith、Bradley D. Smith

  DOI：10.1039/c2ob06783h

  日期：——

  Eight fluorescent squaraine rotaxanes with deep-red absorption/emission wavelengths were prepared and assessed for chemical stability and suitability as water-soluble, fluorescent tracers. The most stable squaraine rotaxanes have four large stopper groups attached to the ends of the encapsulated squaraine, and two members of this structural class have promise as highly fluorescent tracers with rapid renal clearance and very low tissue uptake in living mice.

  制备了八种深红色吸收/发射波长的荧光方酸轮烷，并评估了其化学稳定性和作为水溶性荧光示踪剂的适用性。最稳定的方酸轮烷具有四个大的塞子基团，位于包封方酸的两端，该结构类的两种成员有望作为高荧光示踪剂，在活体小鼠中具有迅速的肾清除率和极低的组织摄取。
• Development of new nonlinear optical polymers based on epoxy- amine oligomers with Bi-chromophore fragments in the side chain
  作者：Gulshat N. Nazmieva、Tatiana А. Vakhonina、Nataliya V. Ivanova、Anastasiya V. Sharipova、Olga D. Fominykh、Maxim A. Smirnov、Marina Yu Balakina、Oleg G. Sinyashin

  DOI：10.1016/j.polymer.2018.07.007

  日期：2018.8

  For the first time bichromophore nonlinear optically active compounds, 3,5-bis [2- (N-ethyl-4- (4′-nitrophenylazo) anilino) ethoxy] benzyl alcohol, DF1, and 3,5-bis [6- (N-methyl-4- (4′-nitrophenylazo) anilino) hexaoxy] benzyl alcohol, DF2, have been synthesized. The synthesis of the epoxy-amine oligomers containing DF1 and DF2 dendritic fragments in the side chain was preceded by molecular design

  首次双发色团非线性光学活性化合物，3,5-双[2-（N-乙基-4-（4'-硝基苯基偶氮）苯胺基）乙氧基]苄醇，DF1和3,5-双[6-（已经合成了N-甲基-4-（4'-硝基苯基偶氮）苯胺基）六氧基]苄醇DF2。在侧链上包含DF1和DF2树枝状片段的环氧胺低聚物的合成之前，进行了分子设计，这表明与发色团结合到DF2中支化中心的己基能够提供更大的发色团迁移率对于DF1中的乙基，因此从NLO活性的观点确定前者的优先级。 通过温和的条件下通过Steglich方法进行酯化反应，将双发色团化合物引入环氧胺低聚物的侧链中。结果，以良好的收率获得了低聚物OAB-DF1（Tg ＝ 122℃）和OAB-DF2（Tg ＝ 107℃），官能化度分别为60mol％和45mol％。NLO系数d 33的值是通过二次谐波产生技术测量的。它们等于29日下午/ V为OAB-DF1和40分/ V为OAB-DF2。
• New “X-type” second-order nonlinear optical (NLO) dendrimers: fewer chromophore moieties and high NLO effects
  作者：Runli Tang、Shengmin Zhou、Wendi Xiang、Yujun Xie、Hong Chen、Qian Peng、Gui Yu、Binwen Liu、Huiyi Zeng、Qianqian Li、Zhen Li

  DOI：10.1039/c5tc00182j

  日期：——

  A larger NLO effect with NLO coefficient of 195.2 pm V⁻¹ was achieved with 3D-extended conformations, even with only 9 chromophore moieties in the dendrimer.

  在树状聚合物中，即使只有9个色团基团，也可以通过3D扩展构象实现较大的NLO效应，其NLO系数为195.2 pm V⁻¹。
• Azo dyestuff intermediate nitro- or aminobenzenes ring-substituted by a
  申请人：Sterling Drug Inc.

  公开号：US04146558A1

  公开（公告）日：1979-03-27

  Water-soluble cationic dyestuffs of the formulae ##STR1## WHEREIN R.sup.0 is hydrogen, lower-alkyl or hydroxy-lower-alkyl; R.sup.1 is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl; R.sup.2 is lower-alkyl, lower-alkenyl, hydroxy-lower-alkyl or -(lower-alkylene)-NR.sup.0 Y or R.sup.1 and R.sup.2 together with the nitrogen atom, are pyrrolidino, piperidino or 4-lower-alkanoyl piperazino; Y is hydrogen or ##STR2## wherein R is hydrogen, lower-alkyl, lower-alkenyl, phenyl or phenyl-lower-alkyl; A is a member selected from the group consisting of an aromatic azo dyestuff residue attached to the quaternary ammonium nitrogen atom through a lower-alkylene bridge. K is a small integer whose value is dependent on the nature of A such that it has a range from one to two; R.sup.8 is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl; R.sup.9 is lower-alkyl, hydroxy-lower-alkyl or NH.sub.2 ; R.sup.10 is lower-alkyl or lower-alkenyl; A.sup.1 is an aromatic azo dyestuff residue attached to the quaternary ammonium nitrogen atom through a lower-alkylene bridge; G is a small integer whose value is dependent on the nature of A.sup.1 such that it has a range from one to two; R.sup.8 ' is lower-alkyl; R.sup.9 ' is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl; R.sup.10 ' is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl or R.sup.9 ' and R.sup.10 ' together with the nitrogen atom are morpholino; A.sup.2 is an aromatic azo dyestuff residue attached to the quaternary ammonium nitrogen atom through a lower-alkylene bridge; h is a small integer whose value is dependent on the nature of A.sup.2 such that it has a range from one to two; and An is an anion are particularly useful for coloring natural fibers, synthetic fiber-forming materials and cellulosic materials. These dyes dye cotton and paper various shades of stable yellows, reds and oranges. The dyeing from these dyes on paper are less prone to bleed and have a high degree of color discharge when bleached with hypochlorite or chlorine bleaches.

  水溶性阳离子染料的化学式为##STR1## 其中R.sup.0为氢、较低烷基或羟基较低烷基；R.sup.1为较低烷基、较低烯烃基或羟基较低烷基；R.sup.2为较低烷基、较低烯烃基、羟基较低烷基或-(较低烷基)-NR.sup.0 Y或R.sup.1和R.sup.2与氮原子一起，为吡咯烷基、哌啶基或4-较低酰基哌嗪基；Y为氢或##STR2## 其中R为氢、较低烷基、较低烯烃基、苯基或苯基较低烷基；A为从芳香偶氮染料残基中选择的一种，通过较低烷基桥连接到季铵氮原子。K是一个小整数，其值取决于A的性质，范围为一到二；R.sup.8为较低烷基、较低烯烃基或羟基较低烷基；R.sup.9为较低烷基、羟基较低烷基或NH.sub.2；R.sup.10为较低烷基或较低烯烃基；A.sup.1为从芳香偶氮染料残基中选择的一种，通过较低烷基桥连接到季铵氮原子；G是一个小整数，其值取决于A.sup.1的性质，范围为一到二；R.sup.8 '为较低烷基；R.sup.9 '为较低烷基、较低烯烃基或羟基较低烷基；R.sup.10 '为较低烷基、较低烯烃基或羟基较低烷基或R.sup.9 '和R.sup.10 '与氮原子一起为吗啉基；A.sup.2为从芳香偶氮染料残基中选择的一种，通过较低烷基桥连接到季铵氮原子；h是一个小整数，其值取决于A.sup.2的性质，范围为一到二；An为阴离子，特别适用于染色天然纤维、合成纤维形成材料和纤维素材料。这些染料可使棉花和纸张呈现各种稳定的黄色、红色和橙色。这些染料在纸张上的染色不易渗出，漂白时与次氯酸盐或氯漂白剂一起具有高度的色彩释放度。
• Pyroglutamic acid derivatives and related compounds which inhibit leukocyte adhesion mediated by VLA-4
  申请人：ELAN PHARMACEUTICALS, INC.

  公开号：EP1612215A1

  公开（公告）日：2006-01-04

  Disclosed are pyroglutamic acid derivatives and related compounds which bind VLA-4. Certain of these compounds also inhibit leukocyte adhesion and, in particular, leukocyte adhesion mediated by VLA-4. Such compounds are useful in the treatment of inflammatory diseases in a mammalian patient, e.g. human, such as asthma, Alzheimer's disease, atherosclerosis, AIDS dementia, diabetes, inflammatory bowel disease, rheumatoid arthritis, tissue transplantation, tumor metastasis and myocardial ischemia. The compounds can also be administered for the treatment of inflammatory brain diseases such as multiple sclerosis.

  本文披露了与VLA-4结合的吡咯烷酸衍生物和相关化合物。其中某些化合物还抑制白细胞粘附，特别是通过VLA-4介导的白细胞粘附。这些化合物在治疗哺乳动物患者（例如人类）的炎症性疾病中非常有用，如哮喘、阿尔茨海默病、动脉粥样硬化、艾滋病痴呆、糖尿病、炎症性肠病、类风湿性关节炎、组织移植、肿瘤转移和心肌缺血。这些化合物还可用于治疗多发性硬化等炎症性脑部疾病。