(1-氨基-3-甲基丁基)磷酸 | 20459-60-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 中文名称: (1-氨基-3-甲基丁基)磷酸
• 英文名称: 1-amino-3-methylbutylphosphonic acid
• 英文别名: α-Amino-γ-methyl-butylphosphonsaeure；(1-azaniumyl-3-methylbutyl)-hydroxyphosphinate
• CAS: 20459-60-3
• 化学式: C₅H₁₄NO₃P
• mdl: MFCD00718857
• 分子量: 167.145
• InChiKey: HGCAUCAWEADMPM-UHFFFAOYSA-N

物化性质

• 熔点：
  274-280 °C
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2931900090
• 安全说明：
  S26,S37/39

SDS

Name:	(1-Amino-3-Methylbutyl)Phosphonic Acid 97% Material Safety Data Sheet
Synonym:	None Known
CAS:	20459-60-3

Section 1 - Chemical Product MSDS Name:(1-Amino-3-Methylbutyl)Phosphonic Acid 97% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
20459-60-3	(1-Amino-3-Methylbutyl)Phosphonic Acid	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea.
Inhalation:
Causes respiratory tract irritation. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately 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. Wash mouth out with 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. Do NOT use mouth-to-mouth resuscitation.
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. 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 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. 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:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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# 20459-60-3: 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:
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: Powder
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 274 - 280 deg C (dec)
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Soluble.
Specific Gravity/Density:
Molecular Formula: C5H14NO3P
Molecular Weight: 167.14

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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:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, oxides of phosphorus, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 20459-60-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(1-Amino-3-Methylbutyl)Phosphonic Acid - 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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 20459-60-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 20459-60-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 20459-60-3 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-氨基-3-甲基丁基)磷酸 在 sodium acetate 、 溶剂黄146 、 potassium hydroxide 作用下， 以 水 为溶剂， 反应 4.5h， 生成 [1-[(5Z)-5-[[4-(dimethylamino)-1-naphthyl]methylene]-4-oxo-2-thioxo-thiazolidin-3-yl]-3-methyl-butyl]phosphonic acid
  参考文献：
  名称：

  在计算机驱动的设计和合成罗丹宁衍生物作为针对烯丙基还原酶InhA的新型抗菌素。

  摘要：

  在这里，我们报告针对结核分枝杆菌结核（Mtb）反-2-烯酰基酰基载体蛋白还原酶（InhA）的4-噻唑烷酮（若丹宁）衍生物的设计，合成和生物学评估。在罗丹宁环第5位具有庞大芳族取代基且在N -3位具有色氨酸残基的化合物对InhA的活性最高，IC 50值为2.7至30μM。实验数据显示与计算研究一致的相关性。他们的抗菌活性评估了对结核分枝杆菌（Mm）（铜绿假单胞菌（Mtb）的模型）。Pa），嗜肺军团菌（Lp）和粪肠球菌（Ef），方法是使用抗感染，抗毒力和抗生素检测方法。34种化合物中有19种降低了10μM的Mm毒力。33的MIC为0.21μM，对Mm表现出有希望的抗生素活性，在30μM的抗感染试验中，Lp的生长降低了89％。32显示对Ef的高抗生素活性，MIC为0.57μM。

  DOI：

  10.1021/acs.jmedchem.5b01620
• 作为产物：
  描述：

  N-苄氧羰基-DL-亮氨酸 在 盐酸 、 溴 、 sodium hydride 、 碳酸氢钠 、 silver nitrate 作用下， 反应 22.25h， 生成 (1-氨基-3-甲基丁基)磷酸
  参考文献：
  名称：

  氨基酸和二肽向其膦酸类似物的转化：氨基烷基膦酸和肽II

  摘要：

  酰基氨基羧酸通过Hunsdiecker反应被降解。溴衍生物与NaPO（OC 2 H 5）2反应。通过酸性水解获得氨基膦酸，通过选择性去除掩蔽取代基获得半封闭的衍生物。通过该途径也制备了两个磷酸肽[例如Alafosfalin（4i）]。

  DOI：

  10.1016/s0040-4020(01)86836-8

文献信息

• Preparation of 1-aminoalkylphosphonic acids and 2-aminoalkylphosphonic acids by reductive amination of oxoalkylphosphonates
  作者：Artur Ryglowski、Pawel Kafarski

  DOI：10.1016/0040-4020(96)00590-x

  日期：1996.8

  By reacting dialkyl 1-oxo- or 2-oxoalkylphosphonates with benzhydrylamine followed by reduction with triacetoxyborohydride and acid hydrolysis gave corresponding aminoalkylphosphonic acids with satisfactory yields. The use of benzylamine, α-methylbenzylamine and tritylamine was unsuccessful in the case of dialkyl 1-oxoalkylphosphonates whereas conversion of 2-oxoalkylphosphonates was also achieved

  通过使1-氧代-或2-氧代烷基膦酸二烷基酯与苯甲基胺反应，然后用三乙酰氧基硼氢化物还原并进行酸水解，以令人满意的产率得到相应的氨基烷基膦酸。在1-氧代烷基膦酸二烷基酯的情况下，苄基胺，α-甲基苄基胺和三苯甲基胺的使用是不成功的，而2-氧代烷基膦酸酯的转化率也较低，但仍可实现。
• Tritylamine (Triphenylmethylamine) in Organic Synthesis; I. The Synthesis of<i>N</i>-(Triphenylmethyl)alkanimines, 1-(Triphenylmethylamino)alkylphosphonic Esters, and 1-Aminoalkylphosphonic Acids and Esters
  作者：Mirosław Soroka、Jan Zygmunt

  DOI：10.1055/s-1988-27576

  日期：——

  The application of tritylamine, a synthetic equivalent of ammonia, to the preparation of unknown N-(triphenylmethyl)alkanimines is described. These imines are convenient synthons for preparation of 1-(triphenylmethylamino)alkylphosphonic esters, which can be used as starting materials for synthesis of 1-aminoalkylphosphonic acids and their derivatives.

  三甲胺（氨的合成类似物）在制备未知的N-(三苯甲基)烷基亚胺中的应用已被描述。这些亚胺是制备1-(三苯甲基氨基)烷基膦酸酯的便利合成子，后者可作为合成1-氨基烷基膦酸及其衍生物的起始材料。
• Preparation of optically active 1-aminoalkylphosphonic acids by stereoselective enzymatic hydrolysis of racemic N-acylated 1-aminoalkylphosphonic acids
  作者：V.A Solodenko、T.N Kasheva、V.P Kukhar、E.V Kozlova、D.A Mironenko、V.K Švedas

  DOI：10.1016/s0040-4020(01)86439-5

  日期：1991.1

  N-Phenylacetylated derivatives of 1-aminoalkylphosphonic acids were synthesized and high enantioselectivity of their hydrolysis by penicillin acylase (EC 3.5.1.11) was demonstrated. Stereoselective enzymatic hydrolysis of racemic 1-(N-phenylacetylamino)alkylphosphonic acids was used for preparation of enantiomeric 1-aminoalkylphosphonic acids. The kinetic regularities of penicillin acylase catalyzed

  合成了1-氨基烷基膦酸的N-苯基乙酰化衍生物，并证明了其被青霉素酰基转移酶水解的高对映选择性（EC 3.5.1.11）。外消旋的1-（N-苯基乙酰氨基）烷基膦酸的立体选择性酶水解用于制备对映异构的1-氨基烷基膦酸。建立了青霉素酰基转移酶催化水解的动力学规律，并优化了生物催化过程，以提高光学纯度和光学活性产物的收率。
• Deamination of 1-Aminoalkylphosphonic Acids: Reaction Intermediates and Selectivity
  作者：Anna Brol、Tomasz K. Olszewski

  DOI：10.3390/molecules27248849

  日期：——

  acids in the reaction with HNO2 (generated "in situ" from NaNO2) yields a mixture of substitution products (1-hydroxyalkylphosphonic acids), elimination products (vinylphosphonic acid derivatives), rearrangement and substitution products (2-hydroxylkylphosphonic acids) as well as H3PO4. The variety of formed reaction products suggests that 1-phosphonoalkylium ions may be intermediates in such deamination

  1-氨基烷基膦酸在与 HNO2 的反应中脱氨（从 NaNO2“原位”生成）产生取代产物（1-羟基烷基膦酸）、消除产物（乙烯基膦酸衍生物）、重排和取代产物（2-羟基烷基膦酸）的混合物) 以及 H3PO4。形成的各种反应产物表明 1-phosphonoalkylium 离子可能是此类脱氨反应的中间体。
• Soroka, Miroslaw; Jaworska, Dorota; Szczesny, Zbigniew, Liebigs Annalen der Chemie, 1990, # 11, p. 1153 - 1155
  作者：Soroka, Miroslaw、Jaworska, Dorota、Szczesny, Zbigniew

  DOI：——

  日期：——