3-氯乙酰苯胺 | 588-07-8

• 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-氯乙酰苯胺
• 中文别名: 3'-氯乙酰苯胺；3-氯乙酰苯胺,98+；3’-氯乙酰苯胺；3-氯乙酰苯胺,98+%
• 英文名称: 3-Chloroacetanilide
• 英文别名: N-(3-chlorophenyl)acetamide；3'-Chloroacetanilide
• CAS: 588-07-8
• 化学式: C₈H₈ClNO
• mdl: MFCD00016341
• 分子量: 169.611
• InChiKey: MUUQHCOAOLLHIL-UHFFFAOYSA-N

物化性质

• 熔点：
  79-81 °C(lit.)
• 沸点：
  172 °C / 0.8mmHg
• 密度：
  1.1885 (rough estimate)
• 溶解度：
  DMSO（少许）、氯仿（少许）、甲醇（少许）
• 颜色/状态：
  NEEDLES FROM 50% GLACIAL ACETIC ACID
• 稳定性/保质期：
  稳定性和反应性： 要避免的物料：氧化物。 要分解的产品：一氧化碳和二氧化碳、氧化氮、氯化氢。

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

ADMET

代谢

在大白兔中产生4-乙酰胺基-2-氯苯酚：Daly等，生物化学药物，17，31（1968年）；在大鼠中产生间氯苯胺：Bray等，生物化学杂志，47，483（1950年）；在大白兔中产生3-氯糖基丙烯酰胺：Kiese，M和Lenk，W，生物化学药物，20，379（1971年）。/来自表格/

YIELDS 4-ACETAMIDO-2-CHLOROPHENOL IN RABBIT: DALY ET AL, BIOCHEM PHARMAC, 17, 31 (1968); M-CHLOROANILINE IN RAT: BRAY ET AL, BIOCHEM J, 47, 483 (1950); 3-CHLOROGLYCOLLANILIDE IN RABBIT: KIESE, M & LENK, W, BIOCHEM PHARMAC, 20, 379 (1971). /FROM TABLE/

来源:Hazardous Substances Data Bank (HSDB)

代谢

当与兔肝微粒体一起孵化时，3-氯乙酰苯胺在第4位被羟基化成3-氯-4-羟基乙酰苯胺。

WHEN INCUBATED WITH RABBIT LIVER MICROSOMES, 3-CHLOROACETANILIDE WAS HYDROXYLATED IN THE 4-POSITION TO 3-CHLORO-4-HYDROXYACETANILIDE.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• RTECS号：
  AE1000100
• 海关编码：
  2924299090
• 安全说明：
  S26,S37/39
• 储存条件：
  贮存： 将密器密封后，储存在密封的主要容器中，并放置在阴凉、干燥的地方。

SDS

Name:	3 -Chloroacetanilide 98% Material Safety Data Sheet
Synonym:	Acetamide, N-(3-Chlorophenyl)-; M-Chloroacetanilide
CAS:	588-07-8

Section 1 - Chemical Product MSDS Name:3 -Chloroacetanilide 98% Material Safety Data Sheet
Synonym:Acetamide, N-(3-Chlorophenyl)-; M-Chloroacetanilide

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
588-07-8	3'-Chloroacetanilide	98%	209-610-3

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. 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.

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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.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 588-07-8: 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.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Granules
Color: off-white to beige
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 77.00 - 79.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: practically insoluble
Specific Gravity/Density:
Molecular Formula: C8H8ClNO
Molecular Weight: 169.61

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, nitrogen.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 588-07-8: AE1000100 LD50/LC50:
Not available.
Carcinogenicity:
3'-Chloroacetanilide - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
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# 588-07-8: No information available.
Canada
CAS# 588-07-8 is listed on Canada's NDSL List.
CAS# 588-07-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 588-07-8 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

类别：农药

毒性分级：中毒

急性毒性：

• 腹腔注射大鼠 LD50: 350 毫克/公斤
• 腹腔注射小鼠 LD50: 610 毫克/公斤

可燃性危险特性：热分解时排出有毒氮氧化物、氯化物及烟雾

储运特性：库房应低温通风且保持干燥

灭火剂：水、二氧化碳、泡沫、干粉

反应信息

• 作为反应物：
  描述：

  3-氯乙酰苯胺 在 乙醇 、 硫酸 、 硝酸 、 亚硝酸 作用下， 生成 对硝基氯苯
  参考文献：
  名称：

  Beilstein; Kurbatow, Justus Liebigs Annalen der Chemie, 1876, vol. 182, p. 108

  摘要：

  DOI：
• 作为产物：
  描述：

  3-硝基氯苯 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 3-氯乙酰苯胺
  参考文献：
  名称：

  金属铜和铜分散的 SiO2 对芳族硝基化合物还原乙酰化的催化活性研究

  摘要：

  N-芳基乙酰胺如对乙酰氨基酚是药物化学中的重要系统。硝基芳烃的还原乙酰化被认为是制备它们的有效途径。开发了在不同条件下在各种催化剂存在下对硝基芳烃进行一锅还原乙酰化的方案。目前的工作研究了金属铜和负载铜体系在温和条件下对硝基芳烃还原乙酰化的催化作用。通过比较Cu/SiO 2与Cu/TiO 2、Cu/Al 2 O的活性，研究了SiO 2、Al 2 O 3、TiO 2和HAp（羟基磷灰石）等支撑材料的影响。3和Cu/HAp。Cu/SiO 2体系成为一种高效的催化剂。在硝基苯还原为苯胺的反应的第一部分，4 wt% Cu-Al 2 O 3和 4 wt% Cu-HAp 都导致部分转化，直至形成偶氮苯，而 4 wt% Cu-TiO 2则表明苯胺转化率为 31%。然而，使用 4 wt% Cu-SiO 2时，苯胺的转化率达到了 100%。体系的乙酰化得到97％产率的N-苯基乙酰胺。还针对选定的硝基芳烃测试了催化剂的活性。通过粉末

  DOI：

  10.1007/s11164-022-04703-y

文献信息

• PYRAZOLO[1,5a]PYRIMIDINE DERIVATIVES AS IRAK4 MODULATORS
  申请人：Arora Nidhi

  公开号：US20120015962A1

  公开（公告）日：2012-01-19

  Compounds of the formula I or II: wherein X, m, Ar, R 1 and R 2 are as defined herein. The subject compounds are useful for treatment of IRAK-mediated conditions.

  式I或II的化合物： 其中X，m，Ar，R1和R2如本文所定义。所述化合物对于治疗IRAK介导的疾病是有用的。
• Combining Eosin Y with Selectfluor: A Regioselective Brominating System for <i>Para</i>-Bromination of Aniline Derivatives
  作者：Binbin Huang、Yating Zhao、Chao Yang、Yuan Gao、Wujiong Xia

  DOI：10.1021/acs.orglett.7b01427

  日期：2017.7.21

  A mild, metal-free, and absolutely para-selective bromination of aniline derivatives has been developed in excellent yields, wherein the organic dye Eosin Y is employed as the bromine source in company with Selectfluor. Neither air nor moisture sensitive, this facile reaction proceeds smoothly at room temperature and completes within a short time. Mechanistic studies indicate a radical pathway; therefore

  已开发出具有优异收率的温和，无金属且绝对对位选择性的苯胺衍生物溴化物，其中有机染料曙红Y与Selectfluor一起用作溴源。无论是对空气还是对湿气都不敏感，这种反应很容易在室温下进行并在短时间内完成。机理研究表明了一条根本途径。因此，的原位产生的溴化试剂的存在，“Selectbrom”，是假设，可合理解释为独特区域选择性段的-bromination Ñ -acyl-以及Ñ -sulfonylanilines。
• A <i>para</i> -C-H Functionalization of Aniline Derivatives via In situ Generated Bulky Hypervalent Iodinium Reagents
  作者：Chao Tian、Xu Yao、Weizhe Ji、Qian Wang、Guanghui An、Guangming Li

  DOI：10.1002/ejoc.201801058

  日期：2018.11.25

  A general para‐selective C‐H functionalization was achieved via a steric control strategy. Para‐iodo, bromo, chloro, nitro, and trifluormethyl aniline derivatives were prepared via in situ generated, bulky hypervalent iodinium reagents in as little as 10 min. Products can be purified without column chromatography or recrystallization, which significantly reduces the waste and simplifies the work‐up

  通过空间控制策略可实现一般的对选择性C-H功能化。对碘，溴，氯，硝基和三氟甲基苯胺衍生物可在短短10分钟内通过原位生成的大体积高价碘试剂制备。无需柱色谱或重结晶即可纯化产品，从而大大减少了浪费并简化了后处理过程。
• Homogeneous Catalytic Hydrogenation of Amides to Amines
  作者：Jacorien Coetzee、Deborah L. Dodds、Jürgen Klankermayer、Sandra Brosinski、Walter Leitner、Alexandra M. Z. Slawin、David J. Cole-Hamilton

  DOI：10.1002/chem.201204270

  日期：2013.8.12

  Hydrogenation of amides in the presence of [Ru(acac)3] (acacH=2,4‐pentanedione), triphos [1,1,1‐tris‐ (diphenylphosphinomethyl)ethane] and methanesulfonic acid (MSA) produces secondary and tertiary amines with selectivities as high as 93 % provided that there is at least one aromatic ring on N. The system is also active for the synthesis of primary amines. In an attempt to probe the role of MSA and

  在[Ru（acac）3 ]（acacH = 2,4-戊二酮），三[[1,1,1-三（二苯基膦甲基）乙烷]]和甲磺酸（MSA）的存在下进行酰胺加氢生成仲胺和叔胺如果在N上至少有一个芳环，则其选择性高达93％。该系统对伯胺的合成也具有活性。为了探索MSA的作用和反应机理，已经从[Ru（acac）3 ]，三醇和MSA或[RuX（OAc）（triphos）]的反应中制备了一系列甲磺酸钠络合物。 （X = H或OAc）或[RuH 2（CO）（triphos ）]与MSA。晶体学表征复合物包括：[茹（OAC-κ 1 O）2（H 2O）（triphos）]，[Ru（OAc‐κ 2 O，O'）（CH 3 SO 3 ‐κ 1 O）（triphos ）]，[Ru（CH 3 SO 3‐ κ 1 O）2（H 2 O）（三膦）]和[孺2（μ-CH 3 SO 3）3（三磷酸）2 ] [CH 3 SO 3 ]，而其他复合物，例如[茹（OAC-κ
• Scope and selectivity in palladium-catalyzed directed C–H bond halogenation reactions
  作者：Dipannita Kalyani、Allison R. Dick、Waseem Q. Anani、Melanie S. Sanford

  DOI：10.1016/j.tet.2006.06.075

  日期：2006.12

  Palladium-catalyzed ligand directed C–H activation/halogenation reactions have been extensively explored. Both the nature of the directing group and the substitution pattern on the arene ring of the substrate lead to different reactivity profiles, and often different and complementary products, in the presence and absence of the catalyst.

  钯催化的配体定向的C–H活化/卤化反应已得到广泛研究。在存在和不存在催化剂的情况下，导向基团的性质和底物的芳环上的取代图案均导致不同的反应性分布，并且常常导致不同的和互补的产物。

表征谱图