57-15-8

• 常用中文名：三氯叔丁醇
• 常用英文名：Chlorobutanol
• CAS号：57-15-8
• 分子式：C₄H₇Cl₃O
• 分子量：177.457
• 相关类别： 原料药 消化系统用药 止吐催吐药
• 发布时间：2018-09-12 19:43:36
• 更新时间：2024-01-02 16:45:50
• Chlorobutanol 是一种药物防腐剂,具有镇静催眠作用。Chlorobutanol 对多种革兰氏阳性和革兰氏阴性细菌 ( Gram-positive and Gram-negative bacteria) 以及几种霉菌孢子和真菌 (fungi) 具有抗性。

名称

• 中文名: 三氯叔丁醇
• 英文名: 1,1,1-Trichloro-2-methyl-2-propanol hemihydrate
• 中文别名: 2-三氯甲基-2-丙醇; 安钠新
• 英文别名: tert-Trichlorobutyl alcohol; MFCD00004461; 1,1,1-Trichloro-2-methylpropan-2-ol; 2-Propanol, 1,1,1-trichloro-2-methyl-; chlorobutanol; 1,1,1-Trichloro-2-methyl-2-propanol; Trichloro-tert-butanol; EINECS 200-317-6; Trichloro-t-butyl alcohol

物化性质

• 密度: 1.4±0.1 g/cm3
• 沸点: 167.0±0.0 °C at 760 mmHg
• 熔点: ~78 °C
• 分子式: C₄H₇Cl₃O
• 分子量: 177.457
• 闪点: 61.8±25.9 °C
• 精确质量: 175.956253
• PSA: 49.69000
• LogP: 2.07
• 蒸汽压: 0.6±0.6 mmHg at 25°C
• 折射率: 1.491
• 储存条件:

  储存与阴凉干燥处。

• 稳定性:

  常温常压下性质稳定。

• 分子结构:

  五、分子性质数据：

  1、 摩尔折射率：26.96

  2、 摩尔体积（cm³/mol）：103.4

  3、 等张比容（90.2K）：246.4

  4、 表面张力（dyne/cm）：32.2

  5、 极化率（10^-24cm³）：10.68

• 计算化学:

  1.疏水参数计算参考值（XlogP）:无

  2.氢键供体数量:1

  3.氢键受体数量:1

  4.可旋转化学键数量:0

  5.互变异构体数量:无

  6.拓扑分子极性表面积20.2

  7.重原子数量:8

  8.表面电荷:0

  9.复杂度:83.8

  10.同位素原子数量:0

  11.确定原子立构中心数量:0

  12.不确定原子立构中心数量:0

  13.确定化学键立构中心数量:0

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

• 更多:

  1. 性状：无色结晶体。以含半分子结晶水型和无水型两种结晶存在。

  2. 密度（g/mL,25/4℃）： 未确定

  3. 相对蒸汽密度（g/mL,空气=1）：未确定

  4. 熔点（ºC）：含半分子结晶水型者熔点78℃，无水型者熔点97

  5. 沸点（ºC,常压）：167

  6. 沸点（ºC, 32.7kPa）：135

  7. 折射率：未确定

  8. 闪点（ºC）：未确定

  9. 比旋光度（º）：未确定

  10. 自燃点或引燃温度（ºC）：未确定

  11. 蒸气压（kPa,25ºC）：未确定

  12. 饱和蒸气压（kPa,60ºC）：未确定

  13. 燃烧热（KJ/mol）：未确定

  14. 临界温度（ºC）：未确定

  15. 临界压力（KPa）：未确定

  16. 油水（辛醇/水）分配系数的对数值：未确定

  17. 爆炸上限（%,V/V）：未确定

  18. 爆炸下限（%,V/V）：未确定

  19. 溶解性：含半分子结晶水型者微溶于水（1：250），易溶于乙醇（1：1）、甘油（1：10）、乙醚、氯仿及挥发油。无水型者易溶于热水，1g能溶于1ml乙醇或10ml甘油中，溶于乙醚、石油醚、丙酮、氯仿、冰醋酸、油类。

生物活性

• 描述: Chlorobutanol 是一种药物防腐剂,具有镇静催眠作用。Chlorobutanol 对多种革兰氏阳性和革兰氏阴性细菌 ( Gram-positive and Gram-negative bacteria) 以及几种霉菌孢子和真菌 (fungi) 具有抗性。
• 相关类别:
  研究领域 >> 感染
  信号通路 >> 抗感染 >> 真菌
  研究领域 >> 神经疾病
  信号通路 >> 抗感染 >> 细菌
• 参考文献:

  [1]. Smoak IW, et al. Chlorobutanol: maternal serum levels and placental transfer in the mouse. Vet Hum Toxicol. 1997 Oct;39(5):287-90.

  [2]. Friesen WT, et al. The antibacterial stability of chlorobutanol stored in polyethylene bottles. Am J Hosp Pharm. 1971 Jul;28(7):507-12.

MSDS

Name: 1 1 1-Trichloro-2-methyl-2-propanol hemihydrate Material Safety Data Sheet Synonym: beta,beta,beta-Trichloro-tert-butyl alcohol hemihydrate; Trichloro-tert-butanol hemihydrate; Acetone chloroform hemihydrate; Chlorobutanol; Chloretone (Parke, Davis); Coliquifilm (Allergan); Methaform; Sedaform CAS: 57-15-8 Section 1 - Chemical Product MSDS Name:1 1 1-Trichloro-2-methyl-2-propanol hemihydrate Material Safety Data Sheet Synonym:beta,beta,beta-Trichloro-tert-butyl alcohol hemihydrate; Trichloro-tert-butanol hemihydrate; Acetone chloroform hemihydrate; Chlorobutanol; Chloretone (Parke, Davis); Coliquifilm (Allergan); Methaform; Sedaform Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS CAS# Chemical Name content EINECS# 57-15-8 1,1,1-Trichloro-2-methyl-2-propanol he 98 unlisted Hazard Symbols: XN Risk Phrases: 22 Section 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW Harmful if swallowed. Potential Health Effects Eye: May cause eye irritation. Skin: May cause skin irritation. Ingestion: May cause irritation of the digestive tract. May be harmful if swallowed. Inhalation: May cause respiratory tract irritation. Chronic: No information found. 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. Skin: In case of contact, flush skin with plenty of water. Remove contaminated clothing and shoes. Get medical aid if irritation develops and persists. Wash clothing before reuse. Ingestion: If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid. Inhalation: If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. Notes to Physician: Treat symptomatically and supportively. 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. This material in sufficient quantity and reduced particle size is capable of creating a dust explosion. Runoff from fire control or dilution water may cause pollution. Extinguishing Media: In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant 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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions. Provide ventilation. 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: Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. 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# 57-15-8: CAS# 6001-64-5: 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 minimize contact with skin. 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: Powder Color: white Odor: camphor pH: Not available. Vapor Pressure: Not available. Viscosity: Not available. Boiling Point: 167 deg C @ 760 mm Hg Freezing/Melting Point: 75-79 deg C Autoignition Temperature: Not applicable. Flash Point: Not applicable. Explosion Limits, lower: Not available. Explosion Limits, upper: Not available. Decomposition Temperature: >167 deg C Solubility in water: 2.5 g/l @ 20C Specific Gravity/Density: Molecular Formula: C4H7Cl3O.0.5H2O Molecular Weight: 186.47 Section 10 - STABILITY AND REACTIVITY Chemical Stability: Stable under normal temperatures and pressures. Substance sublimes readily. Conditions to Avoid: Dust generation, excess heat. Incompatibilities with Other Materials: Strong oxidizing agents, strong alkalies. Hazardous Decomposition Products: Hydrogen chloride, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide. Hazardous Polymerization: Has not been reported. Section 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 57-15-8: UC0175000 CAS# 6001-64-5 unlisted. LD50/LC50: CAS# 57-15-8: Draize test, rabbit, eye: 9180 ug/30S Mild; Draize test, rabbit, skin: 850 ug Mild; Oral, mouse: LD50 = 150 mg/kg; Oral, rat: LD50 = 510 mg/kg. CAS# 6001-64-5. Oral, rabbit, LDLo: 213 mg/kg. Carcinogenicity: 2-Propanol, 1,1,1-trichloro-2-methyl- - Not listed by ACGIH, IARC, or NTP. 1,1,1-Trichloro-2-methyl-2-propanol hemihydrate - 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 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: XN Risk Phrases: R 22 Harmful if swallowed. Safety Phrases: WGK (Water Danger/Protection) CAS# 57-15-8: 2 CAS# 6001-64-5: No information available. Canada CAS# 57-15-8 is listed on Canada's DSL List. CAS# 57-15-8 is not listed on Canada's Ingredient Disclosure List. CAS# 6001-64-5 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 57-15-8 is listed on the TSCA inventory. CAS# 6001-64-5 is not listed on the TSCA inventory. It is for research and development use only. SECTION 16 - ADDITIONAL INFORMATION N/A

毒性和生态

毒理学数据: 1、皮肤或眼睛刺激性：兔子，皮肤接触，标准 Draize test试验，850ug，轻度反应； 兔子，眼睛接触，标准 Draize test实验，9180ug/30，轻度反应 2、急性毒性：狗经口LDLo：238mg/kg；兔子经口LDLo：213mg/kg；青蛙肠外LDLo：800mg/kg 3、致突变性：突变microorganismsTEST系统：细菌-鼠伤寒沙门氏菌：20umol/plate CHEMICAL IDENTIFICATION RTECS NUMBER : UC0175000 CHEMICAL NAME : 2-Propanol, 1,1,1-trichloro-2-methyl- CAS REGISTRY NUMBER : 57-15-8 BEILSTEIN REFERENCE NO. : 0878167 LAST UPDATED : 199701 DATA ITEMS CITED : 8 MOLECULAR FORMULA : C4-H7-Cl3-O MOLECULAR WEIGHT : 177.46 WISWESSER LINE NOTATION : QX1&1&XGGG HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : Standard Draize test ROUTE OF EXPOSURE : Administration onto the skin SPECIES OBSERVED : Rodent - rabbit TYPE OF TEST : Standard Draize test ROUTE OF EXPOSURE : Administration into the eye SPECIES OBSERVED : Rodent - rabbit TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Mammal - dog DOSE/DURATION : 238 mg/kg TOXIC EFFECTS : Lungs, Thorax, or Respiration - other changes TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 213 mg/kg TOXIC EFFECTS : Lungs, Thorax, or Respiration - dyspnea Nutritional and Gross Metabolic - body temperature decrease TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Parenteral SPECIES OBSERVED : Amphibian - frog DOSE/DURATION : 800 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Vascular - regional or general arteriolar or venous dilation Lungs, Thorax, or Respiration - other changes MUTATION DATA TYPE OF TEST : Mutation in microorganisms TEST SYSTEM : Bacteria - Salmonella typhimurium DOSE/DURATION : 20 umol/plate REFERENCE : MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 90,91,1981 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - T1007 No. of Facilities: 798 (estimated) No. of Industries: 3 No. of Occupations: 13 No. of Employees: 25038 (estimated) No. of Female Employees: 21000 (estimated)

安全

• 危害码 (欧洲): Xn
• 风险声明 (欧洲): R22:Harmful if swallowed. R36/37/38:Irritating to eyes, respiratory system and skin .
• 安全声明 (欧洲): S26-S36/37/39
• WGK德国: 3
• 海关编码: 2905143000

合成路线

3294-57-3 67-64-1 ~% 57-15-8

文献：Journal of the American Chemical Society, , vol. 87, # 3 p. 681 - 682

56-23-5 67-64-1 ~66% 57-15-8

文献：Struebing, Baerbel; Jeroschewski, Paul; Deutsch, Angelika Zeitschrift fuer Chemie (Stuttgart, Germany), 1980 , vol. 20, # 12 p. 442 - 443

67-66-3 67-64-1 ~83% 57-15-8

文献：Bal'on, Ya. G.; Shul'man, M. D.; Vakulenko, L. I. Journal of Organic Chemistry USSR (English Translation), 1989 , vol. 25, # 7.1 p. 1231 - 1237 Zhurnal Organicheskoi Khimii, 1989 , vol. 25, # 7 p. 1369 - 1376

75-16-1 ~% 57-15-8

文献：Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, , vol. 142, p. 133 Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, , vol. 143, p. 1223 Chem. Zentralbl., , vol. 77, # II p. 1178

917-64-6 76-02-8 ~% 57-15-8

文献：Roczniki Farm., vol. 2, p. 99 Chem. Zentralbl., , vol. 95, # II p. 304

67-64-1 ~% 57-15-8

文献：Chemische Berichte, , vol. 14, p. 2451

67-66-3 67-64-1 ~% 123-42-2 57-15-8

文献：Journal of the American Pharmaceutical Association (1912-1977), , vol. 28, p. 492 Chem. Zentralbl., , vol. 110, # II p. 4464

512-47-0 7664-93-9 ~% 75-87-6 57-15-8

文献：DE151188 ;

上下游产品

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制备

1.由丙酮与氯仿反应而得：将氯仿、丙酮按1：0.5的配料比加入反应锅内，冷至8℃，搅拌下缓缓加入氢氧化钾，控制温度不超过15℃。加完后维持同温搅拌2h，放料、过滤，滤液浓缩至没有馏液滴出为止。停止加热，降温至25℃加入冰水，搅拌，析出结晶、离心结晶、离心分离，滤饼用蒸馏水洗涤至无氯离子为止。在60-65℃下干燥约2h，过筛，包装。收率为56%（以氯仿计）。原料消耗定额：氯仿1247kg/t、丙酮1688kg/t、氢氧化钾285kg/t。

海关

海关编码	2905143000