R-(-)-5-(2-氨基丙基)-2-甲氧基苯磺酰胺 | 112101-81-2

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 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: R-(-)-5-(2-氨基丙基)-2-甲氧基苯磺酰胺
• 中文别名: 5-[(2R)-2-氨基丙基]-2-甲氧基苯磺酰胺
• 英文名称: 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
• 英文别名: (R)-(-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide；5-[(R)-(2-amino-propyl)]-2-methoxy-benzenesulfonamide；(R)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide；5-[(2R)-2-aminopropyl]-2-methoxybenzenesulfonamide
• CAS: 112101-81-2
• 化学式: C₁₀H₁₆N₂O₃S
• 分子量: 244.315
• InChiKey: IORITYIZDHJCGT-SSDOTTSWSA-N

物化性质

• 熔点：
  166-167 °C
• 沸点：
  445.5±55.0 °C(Predicted)
• 密度：
  1.247±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  16
• 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：
  104
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2935009090
• 储存条件：
  2-8°C

SDS

Name:	(R)-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide Material Safety Data Sheet
Synonym:
CAS:	112101-81-2

Section 1 - Chemical Product MSDS Name:(R)-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
112101-81-2	(R)-5-(2-Aminopropyl)-2-methoxybenzene		unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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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.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
Notes to Physician:
Treat symptomatically and supportively.

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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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical 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.

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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.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 112101-81-2: Personal Protective Equipment Eyes: Not available.
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: Solid
Color: white to light yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 168 - 172 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: C10H16N2O3S
Molecular Weight: 244.31

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Not available.
Incompatibilities with Other Materials:
Not available.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 112101-81-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(R)-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide - Not listed by ACGIH, IARC, or NTP.

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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.
WGK (Water Danger/Protection)
CAS# 112101-81-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 112101-81-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 112101-81-2 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

制备方法

坦索罗辛中间体。

用途简介

（内容暂时未提供）

反应信息

• 作为反应物：
  描述：

  R-(-)-5-(2-氨基丙基)-2-甲氧基苯磺酰胺 在 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 坦索洛新
  参考文献：
  名称：

  A new enzymatic approach to (R)-Tamsulosin hydrochloride

  摘要：

  An enantio selective baker's yeast mediated approach to the pharmacologically active (R)-enantiomer of Tamsulosin hydrochloride is reported. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.01.012
• 作为产物：
  描述：

  坦索罗辛杂质1 在 甲烷 、 palladium 10% on activated carbon 氢气 、 氨 作用下， 以 甲醇 、 水 为溶剂， 20.0~65.0 ℃ 、490.34 kPa 条件下， 反应 0.5h， 以80%的产率得到R-(-)-5-(2-氨基丙基)-2-甲氧基苯磺酰胺
  参考文献：
  名称：

  WO2008/152653

  摘要：

  公开号：

文献信息

• Process for preparation of tamsulosin and its aralkylamine derivatives
  申请人：Jih Hwu Ru

  公开号：US20070015939A1

  公开（公告）日：2007-01-18

  The present invention discloses a new process for the synthesis of tamsulosin and its aralkylamine derivatives, especially (R)-(−)-5-2-[2-(2-alkoxyphenoxy)ethylamino]propyl}-2-alkoxybenzenesulfonamides having the following formula 1 (where R 1 and R 2 represent C 1 -C 4 alkyl groups) and their hydrochloride thereof, and other various pharmaceutical used salts. Tamsulosin hydrochloride (R 1 =Et, R 2 =Me, in its hydrochloride salt form) is an antagonist of α-A adrenoceptors in the prostate. Tamsulosin•HCl occurs as white crystals, which melt with decomposition at approximately 230° C. It is sparingly soluble in water and in methanol, slightly soluble in glacial acetic acid and in ethanol, and practically insoluble in ether.

  本发明公开了一种合成坦洛新及其芳基胺衍生物的新工艺，特别是具有以下化学式1的(R)-(−)-5-2-[2-(2-烷氧基苯氧基)乙基氨基]丙基}-2-烷氧基苯磺酰胺（其中R1和R2代表C1-C4烷基基团）及其盐酸盐，以及其他各种药用盐。坦洛新盐酸盐（R1=Et，R2=Me，在其盐酸盐形式中）是前列腺α-A肾上腺素受体的拮抗剂。坦洛新•HCl呈白色晶体，约在230°C左右分解熔化。它在水和甲醇中溶解度较低，在冰乙酸和乙醇中稍溶，在醚中几乎不溶。
• [EN] NOVEL PROCESS FOR THE SYNTHESIS OF ENANTIOMERICALLY PURE 2-METHOXY-5-[(2R)-2-(4-ALKYLPIPERAZIN-L-YL)PROPYL]-BENZENESULFONAMIDE<br/>[FR] NOUVEAU PROCÉDÉ DE SYNTHÈSE DE 2-MÉTHOXY-5-[(2R)-2-(4-ALKYLPIPÉRAZIN-L-YL)PROPYL]-BENZÈNESULFONAMIDE ÉNANTIOMÉRIQUEMENT PUR
  申请人：HAVALDAR FREDDY H

  公开号：WO2012101648A1

  公开（公告）日：2012-08-02

  Where R is C1-C3 alkyl, alkenyl A novel process for synthesis of compound of Formula 1 comprising steroselective catalytic reduction of compound of Formula IV under hydrogen gas pressure to obtain an intermediate compound of Formula II, which on coupling in presence of coupling agent and base in presence of organic solvent to obtain compound of Formula X, Formula X on reacting with deprotecting agent in presence of organic solvent results in formation of compound of Formula XI, condensation of Formula XI with alkyl halide results in formation of compound of Formula I.

  其中R为C1-C3烷基，烯基，一种合成化合物Formula 1的新方法包括在氢气压力下进行立体选择性催化还原Formula IV化合物以获得Formula II中间体化合物，Formula II在有机溶剂存在下与偶联剂和碱的存在下偶联生成Formula X化合物，Formula X在有机溶剂存在下与去保护剂反应形成Formula XI化合物，Formula XI与烷基卤化物发生缩合反应形成Formula I化合物。
• Sulfamoyl-substituted phenethylamine derivatives, their preparation, and
  申请人：Yamanouchi Pharmaceutical Co., Ltd.

  公开号：US04731478A1

  公开（公告）日：1988-03-15

  A novel process is provided for the preparation of optical isomers of certain sulfamoyl-substituted phenethylamine derivatives which exhibit .alpha.-adrenergic blocking agents which can be used for various treatments such as for the treatment of congestive heart failure.

  提供了一种新颖的工艺，用于制备具有α-肾上腺素受体阻滞剂性质的某些磺胺基取代苯乙胺衍生物的光学异构体，可用于各种治疗，如治疗充血性心力衰竭。
• 光学活性化合物の製造方法
  申请人：株式会社三洋化学研究所

  公开号：JP2005247811A

  公开（公告）日：2005-09-15

  PROBLEM TO BE SOLVED: To provide a method for simply producing (R)-(-)-5-[2-[2-(2-ethoxyphenoxy)ethylamino]-2-methylethyl]-2-methoxybenzenesulfonamide hydrochloride salt and an intermediate for the same at a reduced cost.

  SOLUTION: This method for producing the optically active compound expressed by chemical formula (6) comprises subjecting a compound expressed by chemical formula (5) to optical resolution with an optical resolution agent which has an optically active saccharide derivative as an asymmetry identifying part.

  COPYRIGHT: (C)2005,JPO&NCIPI

  要解决的问题：提供一种简单生产(R)-(-)-5-[2-[2-(2-乙氧基苯氧基)乙基氨基]-2-甲基乙基]-2-甲氧基苯磺酰胺盐酸盐及其中间体的方法，成本降低。解决方案：该生产表达为化学式（6）的手性活性化合物的方法包括将表达为化学式（5）的化合物与具有手性活性葡萄糖衍生物作为不对称识别部分的光学分辨剂进行光学分辨。版权：（C）2005，JPO&NCIPI
• [EN] AN IMPROVED PROCESS FOR THE PREPARATION OF TAMSULOSIN HYDROCHLORIDE<br/>[FR] PROCEDE AMELIORE DE PREPARATION DE CHLORHYDRATE DE TAMSULOSINE
  申请人：NATCO PHARMA LTD

  公开号：WO2004016582A1

  公开（公告）日：2004-02-26

  The present invention relates to an improved process for the preparation of Tamsulosin hydrochloride. Tamsulosin hydrochloride is a widely used drug for the treatment of benign prostate hyperplasia. Tamsulosin hydrochloride has the formula-I given below. (I) The process employs the novel intermediates quarternised benzylidene ammonium salts, N-(phenyl substituted)-[2-(2-ethoxyphenoxy)ethyl]-[2-(4-methoxy-3-sulphamoylphenyl)-1(R)-methyl-ethyl]ammonium halides of the formula-II, (II) where R represents H, 4-OCH3, 4-OH or 4-fluoro and X represents C1, Br or I. And Schiff's bases, novel phenyl substituted 2-methoxy-5-[(2R)-[(1-E/Z-phenyl methylene)amino]propyl]benzenesulfonamide of the formula-III. (III) where R represents H, 4-OCH3, 4-OH or 4-fluoro.

  该发明涉及一种改进的盐酸坦洛新制备工艺。盐酸坦洛新是一种广泛用于治疗良性前列腺增生的药物。盐酸坦洛新的分子式如下所示。该工艺采用了新型中间体季铵化苄亚甲基胺盐、N-(苯基取代)-[2-(2-乙氧基苯氧基)乙基]-[2-(4-甲氧基-3-磺胺基苯基)-1(R)-甲基乙基]铵卤化物的分子式-II，其中R代表H、4-OCH3、4-OH或4-氟，X代表Cl、Br或I。以及席夫碱，新型苯基取代的2-甲氧基-5-[(2R)-[(1-E/Z-苯基亚甲基)氨基]丙基]苯磺酰胺的分子式-III，其中R代表H、4-OCH3、4-OH或4-氟。