(S)-2-羟基对甲苯磺酸 | 143731-32-2

• 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)-2-羟基对甲苯磺酸
• 中文别名: (S)-2-羟基-p-甲苯磺酸丁酯
• 英文名称: (S)-(-)-2-hydroxybutyl tosylate
• 英文别名: (S)-2-Hydroxybutyl tosylate；[(2S)-2-hydroxybutyl] 4-methylbenzenesulfonate
• CAS: 143731-32-2
• 化学式: C₁₁H₁₆O₄S
• 分子量: 244.312
• InChiKey: UVSOURZMHXZMJW-JTQLQIEISA-N

物化性质

• 沸点：
  250 °C
• 密度：
  1.2976 (rough estimate)
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 安全说明：
  S24/25

SDS

Name:	(S)-2-Hydroxybutyl p-tosylate 98+% Material Safety Data Sheet
Synonym:	None
CAS:	143731-32-2

Section 1 - Chemical Product MSDS Name:(S)-2-Hydroxybutyl p-tosylate 98+% Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
143731-32-2	(S)-2-Hydroxybutyl p-tosylate	98+	unlisted

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

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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:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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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. 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.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep refrigerated. (Store below 4C/39F.)

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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# 143731-32-2: 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.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: colorless to light yellow
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: > 250 deg C @ 760.00mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not applicable.
Flash Point: > 93 deg C (> 199.40 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: slightly soluble
Specific Gravity/Density: Not available.
Molecular Formula: C11H16O4S
Molecular Weight: 244.31

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Irritating and toxic fumes and gases.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 143731-32-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(S)-2-Hydroxybutyl p-tosylate - 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# 143731-32-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 143731-32-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 143731-32-2 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

反应信息

• 作为反应物：
  描述：

  1-(Tosyloxy)butan-2-ol 、 (S)-2-羟基对甲苯磺酸 在 toluene-4-sulfonic acid 2-hydroxypropyl ester 作用下， 反应 96.0h， 以(R)-2-acetoxybutyl p-toluenesulfonate (99.0% ee) were obtained at 47.1% conversion的产率得到(R)-2-acetoxybutyl p-toluenesulfonate
  参考文献：
  名称：

  Enzymatic method of making 1,2-diol derivatives and their esters

  摘要：

  本发明涉及一种新的方法，通过酶法从通式1所表示的外消旋醇制备通式2所表示的光学活性醇及其酯，通式3。更详细地说，本发明涉及一种从通式1所表示的醇中，使用脂肪酶作为催化剂，通过立体特异性转酯化反应转化次级羟基，使用有机溶剂或仅使用酰基供体而不使用有机溶剂，生产用作制药中间体的光学活性醇及其酯的方法。根据本发明，通过将1,2-二醇的主要羟基转化为对甲苯磺酰基，并通过脂肪酶立体特异性地转酯化次级羟基，可以生产高产率的高光学纯度的光学活性醇和酯。

  公开号：

  US20070026508A1
• 作为产物：
  描述：

  1-(Tosyloxy)butan-2-ol 生成 (S)-2-羟基对甲苯磺酸
  参考文献：
  名称：

  Amine assisted enzymatic esterification of 1,2-diol monotosylates

  摘要：

  The enzymatic esterification of 1,2-diol monotosylates in organic solvent under standard conditions often fails to achieve the desired 50% conversion due to enzyme inactivation by acidic contaminants. The inclusion of an amine affords rapid conversion to 50% and provides enhanced enantioselectivity.

  DOI：

  10.1016/s0957-4166(00)86160-1

文献信息

• A Systematic Study on the Bakers’ Yeast Reduction of 2-Oxoalkyl Benzoates and 1-Chloro-2-alkanones
  作者：Takashi Sakai、Kou Wada、Takahiko Murakami、Kiichiro Kohra、Norihisa Imajo、Yukihiro Ooga、Sadao Tsuboi、Akira Takeda、Masanori Utaka

  DOI：10.1246/bcsj.65.631

  日期：1992.3

  The bakers’ yeast reduction of a series of 2-oxoalkyl arenecarboxylates [R(C=O)CH2O(C=O)C6H4-p-X] (1a–f) (R = CH3 to n-C6H13; X = H) and the phenyl-modified derivatives (1g–l) (R = n-C5H11, X = OH, CH3, F, Cl, Br, or I) as well as 1-chloro-2-alkanones R(C=O)CH2Cl (6a–f) (R = CH3 to n-C6H13) were systematically investigated. The substrate specificities, configuration and %ee of the reduction products were found to be highly dependent on the length of the alkyl group (R) and the α substituent. Thus, the benzoates 1a–f gave optically active 2-hydroxyalkyl benzoates (2a–f) (R, configuration, %ee) (a: CH3, S, 99; b: C2H5, S, 98; c: C3H7, S, 26; d: n-C4H9, R, 55; e: n-C5H11, S, 15; f: n-C6H13, S, 63) in 11–91% yields. Among the modification experiments of the phenyl group, 1g–l, the p-iodo substituent markedly increased the ee from 15 to 71%, although the yield was rather lowered (22% yield). The reduction of α-chloro ketones 6a–f also gave optically active 1-chloro-2-alkanols (7a–f) [(R, configuration, %ee) (a: CH3, S, 83; b: C2H5, S, 54; c: C3H7, R, 49; d: n-C4H9, R, 80; e, n-C5H11, R, 65; f, n-C6H13, R, 41)] in 16–69% yields.

  对一系列2-氧代烷基苯甲酸酯[R(C=O)CH2O(C=O)C6H4-p-X]（1a-f）（R = CH3 至 n-C6H13；X = H）和苯基修饰衍生物（1g-l）（R = n-C5H11，X = OH、CH3、F、Cl、Br 或 I）以及1-氯-2-烷酮R(C=O)CH2Cl（6a-f）（R = CH3 至 n-C6H13）的面包酵母还原进行了系统研究。发现底物特异性、构型和还原产物的%ee高度依赖于烷基链的长度（R）和α取代基。因此，苯甲酸酯1a-f得到了光学活性的2-羟基烷基苯甲酸酯（2a-f）（R，构型，%ee）（a：CH3，S，99；b：C2H5，S，98；c：C3H7，S，26；d：n-C4H9，R，55；e：n-C5H11，S，15；f：n-C6H13，S，63），产率为11-91%。在苯基修饰实验中，1g-l，碘取代基显著提高了ee值，从15%增加到71%，尽管产率明显下降（产率22%）。α-氯代酮6a-f的还原也得到了光学活性的1-氯-2-烷醇（7a-f）[（R，构型，%ee）（a：CH3，S，83；b：C2H5，S，54；c：C3H7，R，49；d：n-C4H9，R，80；e，n-C5H11，R，65；f，n-C6H13，R，41）]，产率为16-69%。
• Enzymatic method of making 1,2-diol derivatives and their esters with succine anhydride
  申请人：Hwang Ook Soon

  公开号：US20060234362A1

  公开（公告）日：2006-10-19

  The present invention relates to a new process for the preparation of optically active alcohols represented by the general formula 2 and their esters represented by the general formula 3 in scheme 1. In more detail, this invention relates to the process for the preparation of optically active alcohols and their esters which are used as pharmaceutical intermediates by reacting the hydroxyl group stereospecifically by lipase after adding racemic alcohols represented by the general formula 1 and succinic anhydride as an acylating agent to the organic solvent. According to this invention, the primary hydroxyl group of 1,2-diols is transformed by other functional group and the secondary hydroxyl group is esterified stereospecifically with succinic anhydride as an acylating agent. Optically active alcohols and their esters of high optical purity in high yield can be produced by using succinic anhydride as an acylating agent because alcohols can be separated from their esters more easily than those of other conventional methods.

  本发明涉及一种制备光学活性醇的新工艺，其通式为2，以及它们的酯，其通式为3，如图1所示。更详细地说，本发明涉及一种制备光学活性醇及其酯的工艺，通过在有机溶剂中加入通式1的混合醇和琥珀酸酐作为酰化试剂后，通过脂肪酶立体特异性地反应羟基基团。根据本发明，1,2-二醇的主要羟基基团被转化为其他官能团，次要羟基基团通过琥珀酸酐作为酰化试剂被立体特异性地酯化。由于醇可以比其他传统方法更容易地与它们的酯分离，因此可以使用琥珀酸酐作为酰化试剂生产高光学纯度和高收率的光学活性醇及其酯。
• Process for the enzymatic separation of the optical isomers of tosyloxy-alkanols
  申请人：MINISTERO DELL' UNIVERSITA' E DELLA RICERCA SCIENTIFICA E TECNOLOGICA

  公开号：EP0490407A2

  公开（公告）日：1992-06-17

  Described is a process for the biotechnological resolution, by means of stereoselective enzymatic esterification, of the racemic mixture of optical isomers of tosyloxy-alkanols of general formula (I): wherein R represents an alkyl, haloalkyl or C2-Cio alkenyl group, either linear or branched, and n is 1 or 2, by using aliphatic acid anhydrides in the presence of an enzyme which is capable of selectively catalyzing the esterification of the (R) isomer, leaving the (S) isomer basically unchanged.

  本发明描述了一种通过立体选择性酶法酯化，以生物技术解决通式(I)的对羟基烷 醇光学异构体外消旋混合物的工艺： 其中 R 代表直链或支链烷基、卤代烷基或 C2-Cio 烯基，n 为 1 或 2，使用脂肪族酸酐，在一种酶的存在下，该酶能选择性地催化（R）异构体的酯化反应，而（S）异构体基本不变。
• Hamaguchi, Shigeki; Ohashi, Takehisa; Watanabe, Kiyoshi, Agricultural and Biological Chemistry, 1986, vol. 50, # 6, p. 1629 - 1632
  作者：Hamaguchi, Shigeki、Ohashi, Takehisa、Watanabe, Kiyoshi

  DOI：——

  日期：——
• Method for producing optically active glycol derivatives
  申请人：KANEGAFUCHI KAGAKU KOGYO KABUSHIKI KAISHA

  公开号：EP0197484B1

  公开（公告）日：1992-02-05