(S)-(-)-N-[1-(羟甲基)-2-苯基乙基]-4-甲基苯磺酰胺 | 82495-70-3

• 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: (S)-(-)-N-[1-(羟甲基)-2-苯基乙基]-4-甲基苯磺酰胺
• 中文别名: (S)-(-)-n-[1-(羟基甲基)-2-苯基乙基]-4-甲基苯磺酰胺
• 英文名称: (2S)-2-p-toluenesulfonamido-3-phenylpropanol
• 英文别名: (S)-N-(1-hydroxy-3-phenylpropan-2-yl)-4-methylbenzenesulfonamide；N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]-4-methylbenzenesulfonamide
• CAS: 82495-70-3
• 化学式: C₁₆H₁₉NO₃S
• 分子量: 305.398
• InChiKey: QSUGRMCPSKTJTP-HNNXBMFYSA-N

物化性质

• 熔点：
  63-67 °C(lit.)
• 沸点：
  502.3±60.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  避免使用强氧化剂。

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 储存条件：
  保持贮藏器密封，储存在阴凉、干燥处，并确保工作间有良好的通风或排气装置。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
: (S)-(−)-N-[1-(Hydroxymethyl)-2-phenylethyl]-4-
Product name
methylbenzenesulfonamide
CAS-No. : 82495-70-3
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S37/39 Wear suitable gloves and eye/face protection.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C16H19NO3S
Molecular Weight : 305,39 g/mol
Component Concentration
(S)-(-)-N-[1-(Hydroxymethyl)-2-phenylethyl]-4-methylbenzenesulfonamide
CAS-No. 82495-70-3 -

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Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx), Sulphur oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end use(s)
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Impervious clothing., The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: powder
Colour: white
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 63 - 67 °C - lit.
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material. Dissolve or mix the material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine Pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (S)-(-)-N-[1-(羟甲基)-2-苯基乙基]-4-甲基苯磺酰胺 在 copper(II) 2-ethylhexanoate 、 sodium hydride 、 caesium carbonate 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.33h， 生成 N-(((2S,5S)-5-benzyl-4-tosylmorpholin-2-yl)methyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  通过铜促进烯烃的氧化反应立体选择性合成吗啉

  摘要：

  报道了一种新的 2-乙基己酸铜 (II) 促进的醇和胺在烯烃上的加成（氧胺化）。醇加成是分子内的，而与胺的偶联发生在分子间。合成了几种 2-氨基甲基吗啉，收率和非对映选择性都非常好。

  DOI：

  10.1021/ol301984b
• 作为产物：
  描述：

  L-苯丙氨酸乙酯盐酸盐 在 sodium tetrahydroborate 作用下， 以 乙醇 、 水 、 苯 为溶剂， 反应 4.67h， 生成 (S)-(-)-N-[1-(羟甲基)-2-苯基乙基]-4-甲基苯磺酰胺
  参考文献：
  名称：

  通过分子内亚氨基 Diels-Alder 反应非对映选择性合成反式稠合吡咯并 [3,4-b] 喹啉

  摘要：

  摘要 通过芳香胺衍生的醛亚胺与 (S)-2-(N-(3-methylbut-) 分子内环化反应合成了一系列 1aR,2S,4aS-六氢吡咯并[3,4-b]喹啉。 2-烯基)-N-甲苯磺酰氨基)-3-甲基丙醛/(S)-2-(N-(3-甲基丁-2-烯基)-N-甲苯磺酰氨基)-3-苯基丙醛在乙腈中用 InCl3 作为催化剂，在在温和的条件下，产量高，持续时间短。图形概要

  DOI：

  10.1080/00397911.2011.572218
• 作为试剂：
  描述：

  6-methyl-hepta-4,5-dienylamine 在 tetrakis(dimethylamido)titanium(IV) 、 (S)-(-)-N-[1-(羟甲基)-2-苯基乙基]-4-甲基苯磺酰胺 作用下， 以 氘代苯 为溶剂， 反应 51.0h， 生成 2-(2-methylprop-1-en-1-yl)pyrrolidine 、 2-(2-methylprop-1-en-1-yl)pyrrolidine
  参考文献：
  名称：

  Asymmetric hydroamination of aminoallenes catalyzed by titanium and tantalum complexes of chiral sulfonamide alcohol ligands

  摘要：

  A series of bidentate sulfonamide alcohol ligands with varying steric and electronic properties was synthesized. The titanium and tantalum complexes of these ligands, prepared in situ from either Ti(NMe2)(4) or Ta(NMe2)(5), were used as catalysts for the asymmetric hydroamination of 6-methyl-hepta-4,5-dienylamine, giving exclusively the alpha-vinylpyrrolidine product. The titanium derived catalysts gave products with low stereoselectivity, up to 11% ee favoring (+)-2-(2-methyl-propenyl)-pyrrolidine, while the tantalum derived catalysts gave products with higher and opposite stereoselectivity, up to 34% ee favoring (-)-2-(2-methyl-propenyl)-pyrrolidine. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.08.001

文献信息

• β-Cyclodextrin-Catalyzed Monosulfonylation of Amines and Amino Acids in Water
  作者：R. Sridhar、B. Srinivas、V. Pavan Kumar、M. Narender、K. Rama Rao

  DOI：10.1002/adsc.200600652

  日期：2007.8.6

  A mild and efficient procedure has been developed for the first time under biomimetic conditions for the monosulfonylation of various amines and amino acids catalyzed by β-cyclodextrin in water at room temperature to afford the corresponding sulfonamides in high yields.

  首次在仿生条件下开发了一种温和而有效的方法，用于室温下水中β-环糊精催化的各种胺和氨基酸的单磺酰化反应，从而以高收率提供相应的磺酰胺。
• Diversity-Oriented Synthesis Based on the DPPP-Catalyzed Mixed Double-Michael Reactions of Electron-Deficient Acetylenes and β-Amino Alcohols
  作者：Yi Chiao Fan、Ohyun Kwon

  DOI：10.3390/molecules16053802

  日期：——

  opane (DPPP)-catalyzed mixed double-Michael reactions of β-amino alcohols with electron-deficient acetylenes. These reactions are very suitable for the diversity-oriented parallel syntheses of oxizolidines because: (i) they are performed under mild metal-free conditions and (ii) the products are isolated without complicated work-up. To demonstrate the applicability of mixed double-Michael reactions

  在这项研究中，我们通过 1,3-双（二苯基膦）-丙烷 (DPPP) 催化 β-氨基醇与缺电子乙炔的混合双迈克尔反应制备了恶唑烷。这些反应非常适用于面向多样性的 oxizolidines 平行合成，因为：（i）它们在温和的无金属条件下进行；（ii）无需复杂的后处理即可分离产物。为了证明混合双迈克尔反应在制备五元环杂环中的适用性，我们从 5 种 β-氨基醇和 12 种缺电子乙炔制备了 60 种不同的恶唑烷。我们从蛋白质氨基酸衍生的 β-氨基醇合成了对映异构纯形式的这 60 种恶唑烷中的 36 种。
• Formamides as Lewis Base Catalysts in S_NReactions-Efficient Transformation of Alcohols into Chlorides, Amines, and Ethers
  作者：Peter H. Huy、Sebastian Motsch、Sarah M. Kappler

  DOI：10.1002/anie.201604921

  日期：2016.8.16

  and waste‐balance (E‐factor down to 2). Chiral substrates are converted with excellent levels of stereochemical inversion (99 %→≥95 % ee). In a practical one‐pot procedure, the primary formed chlorides can be further transformed into amines, azides, ethers, sulfides, and nitriles. The value of the method was demonstrated in straightforward syntheses of the drugs rac‐Clopidogrel and S‐Fendiline.

  简单的甲酰胺催化剂可促进以苯甲酰氯为唯一试剂将醇类有效转化为烷基氯。这些亲核取代是通过亚胺基活化的醇作为中间体进行的。这种新颖的方法甚至可以在无溶剂条件下进行，其特点是具有出色的官能团耐受性，可扩展性（> 100 g）和废物平衡（电子因子低至2）。手性底物的转化具有优异的立体化学转化水平（99％→≥95％ee）。在实际的一锅法中，初步形成的氯化物可以进一步转化为胺，叠氮化物，醚，硫化物和腈。该方法的价值在药物rac ‐ Clopidogrel和S‐芬迪林。
• Multicomponent Synthesis of Chiral Sulfinimines
  作者：Caroline Roe、Heather Hobbs、Robert A. Stockman

  DOI：10.1002/chem.201003222

  日期：2011.2.25

  Two oxathiozolidine‐S‐oxide templates have been developed and used in a four‐component coupling protocol for the synthesis of a wide range of chiral sulfinimines in high enantiomeric excesses. The templates can be synthesized from cheap commodity chemicals in three steps in high yields. Furthermore the template is easily recovered in high yields for recycling.

  已开发出两个氧杂硫唑烷-S-氧化物模板，并用于四组分偶联方案中，用于合成大量对映体过量的手性亚氨嘧啶。模板可以由廉价的商品化学品分三步以高收率合成。此外，可以容易地以高收率回收模板以进行回收。
• Synthesis of enantioenriched 1,2-trans-diamines using the borono-Mannich reaction with N-protected α-amino aldehydes
  作者：Stéphanie Norsikian、Margaux Beretta、Alexandre Cannillo、Amélie Martin、Pascal Retailleau、Jean-Marie Beau

  DOI：10.1039/c5cc01716e

  日期：——

  The three-component Petasis borono-Mannich reaction starting with easily accessible N-protected α-amino aldehydes produces efficiently and diastereoselectively 1,2-trans-diamines with an enantiomeric excess of up to 98%.

  Petasis硼-曼尼希三组分反应以易获得的N-保护α-氨基醛为起始物，高效地、对映选择性地产生1,2-反式-二胺，其对映体过量高达98%。