Alpha-(氯甲基)-2,4-二氯苯甲醇 | 13692-14-3

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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: Alpha-(氯甲基)-2,4-二氯苯甲醇
• 中文别名: 2,4-二氯-Alpha-氯甲基苯甲醇；α-(氯甲基)-2,4-二氯苯甲醇；2-氯-1-(2,4-二氯苯基)乙醇；Α-(氯甲基)-2,4-二氯苯甲醇
• 英文名称: 2-chloro-1-(2,4-dichlorophenyl)ethanol
• 英文别名: 1-(2,4-dichlorophenyl)-2-chloroethanol
• CAS: 13692-14-3
• 化学式: C₈H₇Cl₃O
• 分子量: 225.502
• InChiKey: XHEPANNURIQWRM-UHFFFAOYSA-N

物化性质

• 熔点：
  48-52 °C
• 沸点：
  323.04°C (rough estimate)
• 密度：
  1.4250 (rough estimate)
• 溶解度：
  可溶于氯仿（轻微，超声处理），甲醇（轻微）
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2906299090
• 安全说明：
  S24/25
• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319
• 储存条件：
  存放于阴凉干燥处

SDS

Name:	alpha-(Chloromethyl)-2 4-dichlorobenzyl alcohol 98% Material Safety Data Sheet
Synonym:
CAS:	13692-14-3

Section 1 - Chemical Product MSDS Name:alpha-(Chloromethyl)-2 4-dichlorobenzyl alcohol 98% Material Safety Data Sheet
Synonym:

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
13692-14-3	alpha-(Chloromethyl)-2,4-dichlorobenzy	98%	237-206-7

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

---

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:
The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation.
Chronic:
Not available.

---

Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids.
Skin:
Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
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 water spray, dry chemical, carbon dioxide, or chemical foam.

---

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.

---

Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

---

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.
Exposure Limits CAS# 13692-14-3: Personal Protective Equipment Eyes: Wear chemical splash goggles.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
Respirators:
A NIOSH/MSHA approved air purifying dust or mist respirator or European Standard EN 149.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: light yellow or beige
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 52 - 54 deg C
Autoignition Temperature: Not available.
Flash Point: > 112 deg C (> 233.60 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H7Cl3O
Molecular Weight: 225.50

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Acids - acid chlorides - acid anhydrides - oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported.

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 13692-14-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
alpha-(Chloromethyl)-2,4-dichlorobenzyl alcohol - Not listed by ACGIH, IARC, or NTP.

---

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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

---

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.
WGK (Water Danger/Protection)
CAS# 13692-14-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 13692-14-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 13692-14-3 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

2,4-二氯-α-氯甲基苯甲醇主要用于合成益康唑的单环硝基咪唑类似物，并作为异康唑杂质6。此外，它还是咪康唑和益康唑的中间体。

化学性质

该物质为结晶态，熔点在52-54℃之间，闪点大于110℃。

生产方法

通过氢化还原1-2,4-三氯苯乙酮可以制得2,4-二氯-α-氯甲基苯甲醇。

反应信息

• 作为反应物：
  描述：

  Alpha-(氯甲基)-2,4-二氯苯甲醇 在 硝酸 、 sodium hydride 作用下， 以 1,4-二氧六环 、 丙酮 、 乙腈 、 mineral oil 为溶剂， 反应 13.0h， 生成 1-[2-[(2,6-二氯苯基)甲氧基]-2-(2,4-二氯苯基)乙基]-1H-咪唑单硝酸盐
  参考文献：
  名称：

  New copper(II) complexes with isoconazole: Synthesis, structures and biological properties

  摘要：

  There is an increasing demand for novel metal-based complexes with biologically relevant molecules in technology and medicine. Three new Cu(II) coordination compounds with antifungal agent isoconazole (L), namely mononuclear complexes [CuCl2(L)(2)] (1), and [Cu(O2CMe)(2)(L)(2)]center dot 2H(2)O (2) and coordination polymer [Cu(pht)(L)(2)](n) (3) (where H(2)pht - o-phthalic acid) were synthesized and characterized by IR spectroscopy, thermogravimetric analysis and X-ray crystallography. X-ray analysis showed that in all complexes, the isoconazole is coordinated to Cu(II) centres by a N atom of the imidazole fragment. In complex I, the square-planar environment of Cu(II) atoms is completed by two N atoms of isoconazole and two chloride ligands, whereas the Cu(II) atoms are coordinated by two N atoms from two isoconazole ligands and two O atoms from the different carboxylate residues: acetate in 2 and phthalate in 3. The formation of an infinite chain through the bridging phthalate ligand is observed in 3. The biosynthetic ability of micromycetes Aspergillus niger CNMN FD 10 in the presence of the prepared complexes 1-3 as well as the antifungal drug isoconazole were studied. Complexes 2 and 3 accelerate the biosynthesis of enzymes (beta-glucosidase, xylanase and endoglucanase) by this fungus. Moreover, a simplified and improved method for the preparation of isoconazole nitrate was developed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.10.040
• 作为产物：
  描述：

  2,2',4'-三氯苯乙酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.67h， 以90%的产率得到Alpha-(氯甲基)-2,4-二氯苯甲醇
  参考文献：
  名称：

  脂肪酶介导的化学反应合成卢立康唑

  摘要：

  开发了一种基于生物催化的新方法来生产有效的抗真菌化合物卢立康唑。事实证明，脂肪酶Novozym435®是关键步骤的强大生物催化剂，其中仅用15分钟即可制备对映体纯的β-卤代醇。再经过几步后，以高收率和高对映体过量获得卢立康唑。

  DOI：

  10.1002/ejoc.201800250

文献信息

• Enantioselective Reduction of α,β-Unsaturated Ketones and Aryl Ketones by Perakine Reductase
  作者：Sheng Cai、Nana Shao、Yuanyuan Chen、Anbang Li、Jie Pan、Huajian Zhu、Hongbin Zou、Su Zeng、Lianli Sun、Jinhao Zhao

  DOI：10.1021/acs.orglett.9b00950

  日期：2019.6.21

  This report describes the enantioselective reduction of structurally diverse α,β-unsaturated ketones and aryl ketones by perakine reductase (PR) from Rauvolfia. This enzymatic reduction produces α-chiral allylic and aryl alcohols with excellent enantioselectivity and most of the products in satisfactory yields. Furthermore, the work demonstrates 1 mmol scale reactions for product delivery without any

  该报告描述了通过来自Rauvolfia的过氧化氢还原酶（PR）对结构多样的α，β-不饱和酮和芳基酮的对映选择性还原。该酶促还原产生具有优异对映选择性的α-手性烯丙基和芳基醇，并且大多数产物均具有令人满意的产率。此外，该工作证明了用于产物递送的1mmol规模的反应，而对收率和对映选择性没有任何有害影响。还描述了由PR和配体配合物的基于3D结构的建模确定的催化机理。
• FUSED HETEROCYCLIC COMPOUNDS AS ION CHANNEL MODULATORS
  申请人：Corkey Britton Kenneth

  公开号：US20120289493A1

  公开（公告）日：2012-11-15

  The present disclosure relates to compounds that are sodium channel inhibitors and to their use in the treatment of various disease states, including cardiovascular diseases and diabetes. In particular embodiments, the structure of the compounds is given by Formula I: wherein Q, R 1 , X 1 , X 2 , Y and R 2 are as described herein, to methods for the preparation and use of the compounds and to pharmaceutical compositions containing the same.

  本公开涉及一类为钠通道抑制剂的化合物，以及它们在治疗各种疾病状态中的应用，包括心血管疾病和糖尿病。在特定实施例中，该化合物的结构由式I给出： 其中Q、R1、X1、X2、Y和R2如本文所述，以及制备和使用该化合物的方法，以及含有该化合物的药物组合物。
• Lipase mediated enzymatic kinetic resolution of phenylethyl halohydrins acetates: A case of study and rationalization
  作者：Thiago de Sousa Fonseca、Kimberly Benedetti Vega、Marcos Reinaldo da Silva、Maria da Conceição Ferreira de Oliveira、Telma Leda Gomes de Lemos、Martina Letizia Contente、Francesco Molinari、Marco Cespugli、Sara Fortuna、Lucia Gardossi、Marcos Carlos de Mattos

  DOI：10.1016/j.mcat.2020.110819

  日期：2020.4

  light on the different reaction rates, docking studies were carried out with all the substrates using MD simulations. The computational data obtained for the β-brominated substrates, based on the parameters analysed such as NAC (near attack conformation), distance between Ser-O and carbonyl-C and oxyanion site stabilization were in agreement with the experimental results. On the other hand, the data

  在来自南极假丝酵母的脂肪酶B （435）的存在下，通过水解反应将含有与芳香环相连的多个基团的外消旋苯乙基卤代醇乙酸酯分解。在所有情况下，动力学拆分都是高度选择性的（E> 200），导致相应的拆分（See> 99％的）-β-卤代醇。但是，理想的50％转化所需的时间为2,4-二氯苯基氯醇乙酸盐的15分钟到2-氯苯基溴醇乙酸盐的216小时。评价了六种氯醇和五种溴醇，后者的反应性较低。对于β-溴化的底物，芳香环上的位阻起着至关重要的作用，而对于β-氯代衍生物则没有观察到。为了阐明不同的反应速率，使用MD模拟对所有底物进行了对接研究。基于分析的参数（例如NAC（近攻构象），Ser-O与羰基-C之间的距离和氧阴离子位点稳定化）获得的有关β-溴化底物的计算数据与实验结果相符。另一方面，
• 咪康唑及其衍生物作为TGR5激动剂的应用
  申请人：河南大学

  公开号：CN111039880B

  公开（公告）日：2022-06-21

  本发明属于医药技术领域，涉及咪康唑及其衍生物在治疗TGR5参与的生物病理过程的疾病和病症的新用途。所述的咪康唑及其衍生物结构式如下。所述咪康唑及其类似物能够激活TGR5活性，能够用于治疗或预防与TGR5活性调节有关的疾病中的用途。
• THERAPEUTIC COMPOUNDS AND THEIR USE IN CANCER
  申请人：Bajji C. Ashok

  公开号：US20070299258A1

  公开（公告）日：2007-12-27

  The invention relates to compounds of Formulae I-III and their therapeutic uses.

  这项发明涉及到I-III式化合物及其治疗用途。

表征谱图