2-mercapto-4,5-dimethoxybenzylamine hydrochloride | 21407-29-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-mercapto-4,5-dimethoxybenzylamine hydrochloride
• 英文别名: 4,5-dimethoxy-2-mercaptobenzylamine hydrochloride；2-Mercapto-4,5-dimethoxybenzylammonium chloride；4,5-dimethoxy-2-mercaptobenzylammonium chloride；4,5-Dimethoxy-2-mercapto-benzyl-ammoniumchlorid；4,5-Dimethoxy-2-mercapto-benzylamine hydrochloride；2-(aminomethyl)-4,5-dimethoxybenzenethiol;hydrochloride
• CAS: 21407-29-4
• 化学式: C₉H₁₃NO₂S*ClH
• 分子量: 235.735
• InChiKey: RZTPGZUSXJKGER-UHFFFAOYSA-N

物化性质

• 熔点：
  174-180 °C
• 稳定性/保质期：
  <p>遵照规定使用和储存，则不会分解。</p>

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.5
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 危险品标志：
  C
• 安全说明：
  S24/25
• 危险类别码：
  R34
• 海关编码：
  2930909090

SDS

Name:	4 5-Dimethoxy-2-Mercapto-Benzylamine Hydrochloride 92% Material Safety Data Sheet
Synonym:	None known
CAS:	21407-29-4

Section 1 - Chemical Product MSDS Name:4 5-Dimethoxy-2-Mercapto-Benzylamine Hydrochloride 92% Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
21407-29-4	4,5-Dimethoxy-2-Mercapto-Benzylamine H	92	unlisted

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.Stench.Corrosive.
Potential Health Effects
Eye:
Causes eye burns. May cause chemical conjunctivitis and corneal damage.
Skin:
Causes skin burns. May cause skin rash (in milder cases), and cold and clammy skin with cyanosis or pale color.
Ingestion:
May cause severe and permanent damage to the digestive tract. Causes gastrointestinal tract burns. May cause perforation of the digestive tract. Mercaptans may cause nausea and headache. Exposure to high concentrations of mercaptans can produce unconsciousness with cyanosis (bluish discoloration of skin due to deficient oxygenation of the blood), cold extremities and rapid pulse. May cause systemic effects.
Inhalation:
Causes chemical burns to the respiratory tract. Aspiration may lead to pulmonary edema. May cause systemic effects. Exposure to high concentrations of mercaptans can produce unconsciousness with cyanosis (bluish discoloration of skin due to deficient oxygenation of the blood), cold extremities and rapid pulse. Mercaptans may cause nausea and headache.
Chronic:
Effects may be delayed.

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Section 4 - FIRST AID MEASURES
Eyes: Get medical aid immediately. Do NOT allow victim to rub eyes or keep eyes closed. Extensive irrigation with water is required (at least 30 minutes).
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. Destroy contaminated shoes.
Ingestion:
Do not induce vomiting. If victim is conscious and alert, give 2-4 cupfuls of milk or water. Never give anything by mouth to an unconscious person. Get medical aid.
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. 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:

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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. Use water spray to keep fire-exposed containers cool. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.
Extinguishing Media:
For small fires, use dry chemical, carbon dioxide, or water spray.
For large fires, use dry chemical, carbon dioxide, alcohol-resistant foam, or water spray. Cool containers with flooding quantities of water until well after fire is out.

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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. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
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.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Corrosives area.

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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# 21407-29-4: 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: Solid
Color: beige
Odor: stench
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 175.00 - 180.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: soluble
Specific Gravity/Density:
Molecular Formula: C9H13NO2S.HCl
Molecular Weight: 235.73

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Strong acids, strong bases, strong oxidizing agents, strong reducing agents.
Hazardous Decomposition Products:
Hydrogen chloride, nitrogen oxides, carbon monoxide, oxides of sulfur, irritating and toxic fumes and gases, carbon dioxide, hydrogen sulfide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 21407-29-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4,5-Dimethoxy-2-Mercapto-Benzylamine Hydrochloride - 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
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2811
Packing Group: II
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: II
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: II

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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 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 21407-29-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 21407-29-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 21407-29-4 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：

  2-mercapto-4,5-dimethoxybenzylamine hydrochloride 在 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 2.5h， 生成 9,10-Dimethoxy-6-methyl-7H,12aH-5-oxa-12-thia-6a-aza-benzo[a]anthracene
  参考文献：
  名称：

  Szabo, Janos; Bernath, Gabor; Sohar, Pal, Heterocycles, 1987, vol. 26, # 9, p. 2381 - 2384

  摘要：

  DOI：
• 作为产物：
  描述：

  S,N-dibenzoyl-4,5-dimethoxy-2-mercaptobenzylamine 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 5.0h， 以76.4%的产率得到2-mercapto-4,5-dimethoxybenzylamine hydrochloride
  参考文献：
  名称：

  Szabo, J.; Varga, I.; Fodor, L., Acta Chimica Hungarica, 1984, vol. 115, # 4, p. 429 - 437

  摘要：

  DOI：

文献信息

• Generation of an<i>S</i>-Peptide via an<i>N</i>–<i>S</i>Acyl Shift Reaction in a TFA Solution
  作者：Ken’ichiroh Nakamura、Megumi Sumida、Toru Kawakami、Thomas Vorherr、Saburo Aimoto

  DOI：10.1246/bcsj.79.1773

  日期：2006.11

  An N–S acyl shift reaction of thiol-containing peptides in a trifluoroacetic acid (TFA) solution was confirmed by a combination of 13C NMR spectroscopy, reversed-phase (RP) HPLC, and MS analyses. A model peptide containing a cysteine residue was transformed into an S-peptide in a TFA solution. The S-peptide was quickly transformed to the original peptide during RP-HPLC analysis even when an eluent that contained 0.1% TFA was used. A peptide that had an N-2-mercapto-4,5-dimethoxybenzyl (Dmmb) group was also transformed into an S-peptide, forming a thioester bond with the thiol of the Dmmb group by TFA treatment. The generated S-peptide was isolated by directly injecting the reaction mixture into a RP-HPLC and was readily converted to the corresponding 2-sulfoethyl thioester via an intermolecular thiol exchange reaction with sodium 2-mercaptoethanesulfonate. The 2-sulfoethyl peptide thioester is widely used as a building block in polypeptide synthesis. The N–S acyl shift reaction observed in peptides with or without an auxiliary group provides a new route for the preparation of peptide thioesters.

  在三氟乙酸（TFA）溶液中，通过13C NMR光谱学、反相（RP）高效液相色谱（HPLC）和质谱分析的组合，证实了含硫醇肽的N–S酰基移位反应。一个含有半胱氨酸残基的模型肽在TFA溶液中转化为S-肽。即使在含有0.1% TFA的洗脱液中进行RP-HPLC分析时，S-肽也迅速转变为原始肽。含有N-2-巯基-4,5-二甲氧基苄基（Dmmb）基团的肽也通过TFA处理转化为S-肽，与Dmmb基团的硫醇形成硫酯键。生成的S-肽通过直接将反应混合物注入RP-HPLC中分离，并通过与硫醇乙磺酸钠的分子间硫醇交换反应，容易地转化为相应的2-磺乙基硫酯。2-磺乙基肽硫酯广泛用作多肽合成中的构建块。在有无辅助基团的肽中观察到的N–S酰基移位反应为肽硫酯的制备提供了一条新途径。
• Synthesis of 1,2-benzisothiazoles by the oxidative ring contraction of 2-aryl- and 4-aryl-3,4-dihydro-2H-1,3-benzothiazines
  作者：János Szabó、Erzsébet Szűcs、Lajos Fodor、Gábor Bernáth、Pál Sohár

  DOI：10.1016/s0040-4020(01)80102-2

  日期：1989.1

  4-aryl isomers of the latter (11a, b) furnished 2-substituted 1,2-benzisothiazolidine 1-oxides (7a-c) and their 3-aryl analogues (12a, b), respectively. The observed conversions of the 1,3-benzothiazines to 1,2-benzisothiazole and to 1,2-benzisothiazolidines are new ring transformation reactions of 3,4-dihydro-1,3-benzothiazines, representing a new route for the synthesis of 1,2-benzisothiazoles and

  6,7-二甲氧基-2-芳基-3,4-二氢-2H-1,3-苯并噻嗪（1a-e）的高碘酸钠氧化得到5,6-二甲氧基-1,2-苯并噻唑（4）。N-取代的类似物（6a-c）和后者的4-芳基异构体（11a，b）提供了2-取代的1,2-苯并噻唑烷1-氧化物（7a-c）及其3-芳基类似物（12a， b）分别。观察到的1,3-苯并噻嗪向1,2-苯并噻唑并向1,2-苯并噻唑烷的转化是3,4-二氢-1,3-苯并噻嗪的新环转化反应，代表了1的合成新途径，2-苯并噻唑及其氢化衍生物。
• 2,3-Dihydroferroceno[3,4]pyrrolo[2,1-b]thiazol-5(8b)-ones: Synthesis, Structure and DFT Study on the Mechanism of Chemo- and Diastereoslective Annulations of (Sp)-2-Formylferrocenecarbonyl Fluoride and (Sp)-2-Formylferrocenecarboxylic Acid
  作者：Zoltán Kovács、Antal Csámpai

  DOI：10.3390/molecules26051420

  日期：——

  synthetic control experiments and a series of further DFT modelling studies, including energetic and MO analysis of the iminium intermediates, we propose a mechanism for the thiazolidine-forming annulations that proceed via primary N-acylation followed by proton-mediated cyclocondensation and subsequent diastereoselective sulfhydryl-attack on the resulting iminium center.

  通过在室温下在吡啶存在下于二氯甲烷中进行的易处理但具有足够反应性的（S p）-2-甲酰基二茂铁碳酰氟与半胱胺盐酸盐和对映体半胱氨酸甲酯的环化反应将具有平面手性和中心手性的2,3-二氢铁茂铁[3,4]吡咯并[2,1-b]噻唑-5（8 bH）-的第一成员制备为单一对映体。还为直接探索这些有机金属杂环的合成拟定了一种原子经济程序（S p通过CDI和TFA原位活化的）-2-甲酰基二茂铁羧酸依次加入到反应混合物中。分离的非对映异构体的相对构型，因此，是通过DFT结构优化支持的NMR测量确定的。根据合成控制实验的结果以及一系列进一步的DFT建模研究，包括对亚胺中间体的能量分析和MO分析，我们提出了形成噻唑烷环化反应的机理，该机理是通过主要的N-酰化反应，然后进行质子反应-进行的。介导的环缩合反应以及随后对所得亚胺中心的非对映选择性巯基攻击。
• Synthesis of 4,5-dihydro-1,4-benzothiazepine derivatives via ring expansion
  作者：L. Fodor、J. Szabó、G. Bernáth、L. Párkányi、P. Sohár

  DOI：10.1016/s0040-4039(01)92424-4

  日期：1981.1

  Basic treatment in methanol of a chloro-β-lactam fused with dihydrobenzothiazine led to the corresponding 1,4-benzothiazepine derivative via a new ring expansion. The structure of the product, deduced from IR and 1H NMR data, was confirmed by X-ray measurements.

  在甲醇中对氯-β-内酰胺与二氢苯并噻嗪稠合的碱性处理通过新的扩环反应生成相应的1,4-苯并噻氮庚因衍生物。由IR和1 H NMR数据推导的产物结构通过X射线测量证实。
• Tandem ligation at X-Cys and Gly-Gly positions via an orthogonally protected auxiliary group
  作者：Jane C. Spetzler、Thomas Hoeg-Jensen

  DOI：10.1016/j.bmc.2007.05.006

  日期：2007.7

  acetamidomethyl (Acm) and incorporated into a peptide thioester for use in tandem native chemical ligation. Upon ligation between the thioester and a Cys-peptide, Acm was removed from Dmmb using silver acetate, and a second ligation reaction was done at the Dmmb position. Dmmb removal using TFMSA-TFA effected overall tandem ligation at X-Cys and Gly-Gly.

  4,5-二甲氧基-2-巯基苄胺（Dmmb）已被乙酰氨基甲基（Acm）保护，并掺入肽硫酯中，用于串联天然化学连接。在硫酯和Cys-肽之间连接后，使用乙酸银从Dmmb去除Acm，并且在Dmmb位置进行第二次连接反应。使用TFMSA-TFA去除Dmmb会影响X-Cys和Gly-Gly的整体串联连接。