5-(溴甲基)-4-甲基-2-[4-(三氟甲基)苯基]-1,3-噻唑 | 439134-78-8

• 物质功能分类: 有机原料 - 杂环化合物
• 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: 5-(溴甲基)-4-甲基-2-[4-(三氟甲基)苯基]-1,3-噻唑
• 英文名称: 5-(bromomethyl)-4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole
• CAS: 439134-78-8
• 化学式: C₁₂H₉BrF₃NS
• 分子量: 336.175
• InChiKey: IBJHFQRRDNHDBG-UHFFFAOYSA-N

物化性质

• 熔点：
  64 °C
• 沸点：
  373.7±52.0 °C(Predicted)
• 密度：
  1.551±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2934100090
• 包装等级：
  II
• 危险类别：
  8
• 危险性防范说明：
  P301+P330+P331,P303+P361+P353,P363,P304+P340,P310,P321,P260,P264,P280,P305+P351+P338,P405,P501
• 危险品运输编号：
  3261
• 危险性描述：
  H314
• 储存条件：
  存储条件为2-8°C，并需保存在惰性气体中。

SDS

Name:	5-(Bromomethyl)-4-methyl-2-[4-(trifluoromethyl)phenyl]-1 3-thiazole Material Safety Data Sheet
Synonym:	None Known
CAS:	439134-78-8

Section 1 - Chemical Product MSDS Name:5-(Bromomethyl)-4-methyl-2-[4-(trifluoromethyl)phenyl]-1 3-thiazole Material Safety Data Sheet
Synonym:None Known

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
439134-78-8	5-(Bromomethyl)-4-methyl-2-[4-(trifluo	97+	unlisted

Hazard Symbols: C
Risk Phrases: 34

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
Chronic exposure may cause effects similar to those of acute exposure.

---

Section 4 - FIRST AID MEASURES
Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid immediately.
Skin:
In case of contact, immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Get medical aid immediately. Wash clothing before reuse.
Ingestion:
If swallowed, do NOT induce vomiting. Get medical aid immediately.
If victim is fully conscious, give a cupful of water. Never give anything by mouth to an unconscious person.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If breathing is difficult, give oxygen. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
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:
Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions. Provide ventilation. Vacuum or sweep up material and place into a suitable, dry disposal container.

---

Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing.
Keep container tightly closed. Do not ingest or inhale. Discard contaminated shoes. Use only with adequate ventilation.
Storage:
Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances. Store under an inert atmosphere.

---

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# 439134-78-8: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 68.5-70.5 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C12H9F3NSBr
Molecular Weight: 336.18

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Alcohols, amines, oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide, hydrogen fluoride gas, hydrogen bromide.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 439134-78-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
5-(Bromomethyl)-4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: Pseudomonas putida:

---

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

---

Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: CORROSIVE SOLID, ACIDIC ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing Group: III
IMO
Shipping Name: CORROSIVE SOLID, ACIDIC ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing Group: III
RID/ADR
Shipping Name: CORROSIVE SOLID, ACIDIC ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing group: III

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
Safety Phrases:
S 6 Keep under nitrogen.
S 22 Do not breathe dust.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 439134-78-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 439134-78-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 439134-78-8 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-(溴甲基)-4-甲基-2-[4-(三氟甲基)苯基]-1,3-噻唑 在 一水合肼 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 ethyl 2-methyl-2-[(4-{[({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)amino]carbonyl}phenyl)oxy]propanoate
  参考文献：
  名称：

  Substituted 2-[(4-Aminomethyl)phenoxy]-2-methylpropionic Acid PPARα Agonists. 1. Discovery of a Novel Series of Potent HDLc Raising Agents

  摘要：

  The peroxisome proliferator activated receptors PPAR alpha, PPAR gamma, and PPAR delta are ligand-activated transcription factors that play a key role in lipid homeostasis. The fibrates raise circulating levels of high-density lipoprotein cholesterol and lower levels of triglycerides in part through their activity as PPAR alpha agonists; however, the low potency and restricted selectivity of the fibrates may limit their efficacy, and it would be desirable to develop more potent and selective PPAR alpha agonists. Modification of the selective PPAR delta agonist 1 (GW501516) so as to incorporate the 2-aryl-2-methylpropionic acid group of the fibrates led to a marked shift in potency and selectivity toward PPAR alpha agonism. Optimization of the series gave 25a, which shows EC50 = 4 nM on PPAR alpha and at least 500-fold selectivity versus PPAR delta and PPAR gamma. Compound 25a (GW590735) has been progressed to clinical trials for the treatment of diseases of lipid imbalance.

  DOI：

  10.1021/jm058056x
• 作为产物：
  描述：

  4-(三氟甲基)硫代苯甲酰胺 在 N-溴代丁二酰亚胺(NBS) 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 15.66h， 生成 5-(溴甲基)-4-甲基-2-[4-(三氟甲基)苯基]-1,3-噻唑
  参考文献：
  名称：

  WO2006/121223

  摘要：

  公开号：

文献信息

• BENZOAZEPIN-OXY-ACETIC ACID DERIVATIVES AS PPAR-DELTA AGONISTS USED FOR THE INCREASE OF HDL-C, LOWER LDL-C AND LOWER CHOLESTEROL
  申请人：Kuo Gee-Hong

  公开号：US20070244094A1

  公开（公告）日：2007-10-18

  The invention is directed to compounds of Formula (I) useful as PPAR agonists. Pharmaceutical compositions and methods of treating one or more conditions including, but not limited to, diabetes, nephropathy, neuropathy, retinopathy, polycystic ovary syndrome, hypertension, ischemia, stroke, irritable bowel disorder, inflammation, cataract, cardiovascular diseases, Metabolic X Syndrome, hyper-LDL-cholesterolemia, dyslipidemia (including hypertriglyceridemia, hypercholesterolemia, mixed hyperlipidemia, and hypo-HDL-cholesterolemia), atherosclerosis, obesity, and other disorders related to lipid metabolism and energy homeostasis complications thereof, using compounds of the invention are also described.

  该发明涉及一种化合物，其化学式为（I），可用作PPAR激动剂。还描述了使用该发明的化合物治疗糖尿病、肾病、神经病、视网膜病变、多囊卵巢综合征、高血压、缺血、中风、肠易激综合征、炎症、白内障、心血管疾病、代谢X综合征、高LDL胆固醇血症、血脂异常（包括高甘油三酯血症、高胆固醇血症、混合性高脂血症和低HDL胆固醇血症）、动脉粥样硬化、肥胖以及其他与脂质代谢和能量稳态并发症相关的疾病的药物组合物和治疗方法。
• Thia-and oxazoles and their use as ppars activators
  申请人：——

  公开号：US20040102493A1

  公开（公告）日：2004-05-27

  A compound of formula (I) or pharmaceutically acceptable salts and solvates thereof. R 1 and R 2 are independently H or C 1-3 alkyl, m is 0-3; X 1 is NH, NCH 3 , O, S; R 3 , R 4 and R 5 are independently H, CH 3 , CF 3 , OCH 3 , allyl or halogen; X 2 is (CR 10 R 11 )n wherein n is 1 or 2; R 10 and R 11 independently represent H, fluorine or C 1-16 alkyl; R 26 and R 27 are independently H, C 1-3 alkyl or R 26 and R 27 together with the carbon atom to which they are bonded form a 3-5 membered cycloalklyl ring. R 6 and R 7 independently represent H, fluorine or C 1-16 alkyl; R 9 is C 1-6 alkyl or CF 3 ; One of Y and Z is N, the other is S or O; Each R 8 independently represents CF 3 , OCH 3 , CH 3 or halogen; y is O, 1, 2, 3, 4, 5. Use of a compound of formula (I) for the manufacture of a medicament for the prevention or treatment of a hPPAR mediated disease or condition, such as dyslipidemia, syndrome X, heart failure, hypercholesteremia, cardiovascular disease, type II diabetes mellitus, type 1 diabetes, insulin resistance hyperlipidemia, obesity, anorexia bulimia, inflammation and anorexia nervosa. 1

  一种具有化学式（I）或其药学上可接受的盐和溶剂的化合物。R1和R2独立地表示H或C1-3烷基，m为0-3；X1为NH、NCH3、O、S；R3、R4和R5独立地表示H、CH3、CF3、OCH3、烯丙基或卤素；X2为（CR10R11）n，其中n为1或2；R10和R11独立地表示H、氟或C1-16烷基；R26和R27独立地表示H、C1-3烷基或R26和R27与它们结合的碳原子一起形成3-5环的环烷基环。R6和R7独立地表示H、氟或C1-16烷基；R9为C1-6烷基或CF3；Y和Z中的一个为N，另一个为S或O；每个R8独立地表示CF3、OCH3、CH3或卤素；y为O、1、2、3、4、5。使用具有化学式（I）的化合物制备用于预防或治疗hPPAR介导的疾病或症状的药物，例如脂质代谢异常、X综合征、心力衰竭、高胆固醇血症、心血管疾病、2型糖尿病、1型糖尿病、胰岛素抵抗性高脂血症、肥胖、厌食症、炎症和神经性厌食症。
• [EN] PROCESS FOR PREPARING THIAZOLE DERIVATIVE AND THE INTERMEDIATE COMPOUNDS FOR PREPARING THE SAME<br/>[FR] PROCEDE POUR L'ELABORATION DE DERIVE THIAZOLE ET COMPOSES INTERMEDIAIRES A CET EFFET
  申请人：KANG HEONJOONG

  公开号：WO2003106442A1

  公开（公告）日：2003-12-24

  The present invention provides a process for preparing thiazole derivatives of formula (XI), that activate the delta subtype of the human Peroxisome Proliferator Activated Receptor (hPPARδ), and also provides processes for compounds of formula (VI), (VII), (VIII) and (IX), intermediate compounds for preparation of the above compounds of formula (XI).

  本发明提供了一种制备式（XI）噻唑衍生物的方法，该方法激活人类过氧化物酶体增殖物激活受体（hPPARδ）的δ亚型，并且提供了式（VI）、（VII）、（VIII）和（IX）化合物的方法，用于制备上述式（XI）化合物的中间体化合物。
• [EN] NOVEL COMPOUNDS AS CALCIUM CHANNEL BLOCKERS<br/>[FR] NOUVEAUX COMPOSÉS UTILISÉS COMME BLOQUEURS DES CANAUX CALCIQUES
  申请人：ABBOTT LAB

  公开号：WO2010039947A1

  公开（公告）日：2010-04-08

  The present application relates to calcium channel inhibitors containing compounds of formula (I) wherein Ar1, Ar2, L1, L2, n, R1, R4, X and Y are as defined in the specification. The present application also relates to compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.

  本申请涉及含有式（I）化合物的钙通道抑制剂，其中Ar1、Ar2、L1、L2、n、R1、R4、X和Y如规范中所定义。本申请还涉及包含这些化合物的组合物，以及使用这些化合物和组合物治疗疾病和疾病的方法。
• 一种选择性PPARδ激动剂GW501516的制备方法
  申请人：无锡科华生物科技有限公司

  公开号：CN109897013B

  公开（公告）日：2023-04-07

  本发明公开了一种选择性PPARδ激动剂GW501516的制备方法，属于医药中间体合成技术领域。以邻甲基苯酚为原料，通过氧化剂和碘/溴化钾得到4‑碘/溴‑2‑甲基苯酚，接着与氯/溴乙酸叔丁酯反应得到(4‑溴/碘‑2‑甲基苯氧基)‑乙酸叔丁基酯，随后进行格氏试剂交换，依次与硫粉和5‑(溴甲基)‑4‑甲基‑2‑[4‑(三氟甲基)苯基]‑1,3‑噻唑反应得到2‑[2‑甲基‑4‑‑[[[4‑甲基‑2‑[4‑(三氟甲基)苯基]‑5‑噻唑基]甲基]硫代]苯氧基]乙酸叔丁酯，最后水解得到选择性PPARδ激动剂GW501516。本发明工艺操作简便，条件温和，原料价廉易得，为该药物的合成放大提供了借鉴。