(1-aminocyclopentyl)phosphonic acid | 67550-64-5

• 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
• 英文名称: (1-aminocyclopentyl)phosphonic acid
• 英文别名: alpha-Aminocyclopentylphosphonic acid
• CAS: 67550-64-5
• 化学式: C₅H₁₂NO₃P
• mdl: MFCD20547577
• 分子量: 165.129
• InChiKey: FBXFXDVQDQRPCE-UHFFFAOYSA-N

物化性质

• 熔点：
  274-276 °C
• 沸点：
  354.3±44.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)
• 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)：
  -3.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• 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
• 储存条件：
  存放在阴凉干燥处即可。

SDS

Name:	(1-Amino-1-cyclopentyl)phosphonic acid 97% Material Safety Data Sheet
Synonym:	alpha-Aminobenzylphosphonic acid
CAS:	67550-64-5

Section 1 - Chemical Product MSDS Name:(1-Amino-1-cyclopentyl)phosphonic acid 97% Material Safety Data Sheet
Synonym:alpha-Aminobenzylphosphonic acid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
67550-64-5	(1-Amino-1-cyclopentyl)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. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled. Can produce delayed pulmonary edema.
Chronic:
No information found.

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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 cool, dry place. Store in a tightly closed container.

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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# 67550-64-5: 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 - 276 deg C (de
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: C5H12NO3P
Molecular Weight: 165.13

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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:
Dust generation.
Incompatibilities with Other Materials:
Strong 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# 67550-64-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(1-Amino-1-cyclopentyl)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# 67550-64-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 67550-64-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 67550-64-5 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-aminocyclopentyl)phosphonic acid 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 15.0h， 生成 (1-氨基环戊基)膦酸二乙酯
  参考文献：
  名称：

  A Facile Conversion of Aminoalkanephosphonic Acids into Their Diethyl Esters. The Use of Unblocked Aminoalkanephosphonic Acids in Phosphono Peptide Synthesis

  摘要：

  报告采用简单高效的两步法，从氨基烷基膦酸制备氨基烷基膦酸二乙酯。 所获得的酯类可作为膦肽合成的底物。

  DOI：

  10.1055/s-1988-27550
• 作为产物：
  描述：

  O,O-diisopropyl cyclopentylphosphonate 在 palladium on activated charcoal 盐酸 、 正丁基锂 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 溶剂黄146 为溶剂， -78.0~25.0 ℃ 、100.0 kPa 条件下， 反应 14.5h， 生成 (1-aminocyclopentyl)phosphonic acid
  参考文献：
  名称：

  A New and Efficient Synthesis of α-Amino Cycloalkyl-Phosphonic AcidsviaElectrophilic Azidation of Cycloalkylphosphonates

  摘要：

  alpha-Amino cyclobutyl-, cyclopentyl- and cyclohexylphosphonic acids (13) were efficiently prepared from the related unsubstituted cycloalkphosphonates (5), in three steps including electrophilic azidation of the corresponding lithiated carbanions, hydrogenation of the intermediate alpha-azido cycloalkyl-phosphonates (10) and acidic hydrolysis of the resulting alpha-amino cycloalkyl-phosphonates (12).

  DOI：

  10.1080/00397919608004650

文献信息

• Single-Step Ugi Multicomponent Reaction for the Synthesis of Phosphopeptidomimetics
  作者：Andrea F. G. Gargano、Stefanie Buchinger、Michal Kohout、Wolfgang Lindner、Michael Lämmerhofer

  DOI：10.1021/jo401372x

  日期：2013.10.18

  optimization of an effective microwave-assisted multicomponent reaction to produce a novel class of phosphopeptidomimetic compounds. When using aminophosphonic acids (α, β, γ), aldehydes, and isocyanides as reactants and alcohols as solvents, these building blocks are merged to functionalized amido-aminophosphonate structures in a novel Ugi-type one-pot transformation reaction. A high level of structural diversity

  本文介绍了设计和优化有效的微波辅助多组分反应，以生产一类新型的磷酸肽模拟化合物。当使用氨基膦酸（α，β，γ），醛和异氰酸酯作为反应物，并用醇作为溶剂时，这些结构单元在新型的Ugi型单锅转化反应中合并为官能化的氨基-氨基膦酸酯结构。通过这种合成方法可以实现高水平的结构多样性，从而为生产新型生物活性分子的功能化构建基块提供了平台。通过反应参数的变化以及对各种反应底物的评估，探索了这种多组分合成方案的一般范围。
• N-(Phosphonoacetyl)amino phosphonates. Phosphonate analogs of N-(phosphonoacetyl)-L-aspartic acid (PALA)
  作者：Pawel Kafarski、Barbara Lejczak、Przemyslaw Mastalerz、Danuta Dus、Czeslaw Radzikowski

  DOI：10.1021/jm00149a002

  日期：1985.11

  Michaelis-Arbuzov reaction of N-(chloroacetyl)amino phosphonic acids or their esters, followed by acidolysis, gives moderate yields of N-(phosphonoacetyl) derivatives of a variety of (aminoalkyl)phosphonic acids, including analogues of the cytostatic agent PALA, in which the alpha- or beta-carboxylic groups in the aspartate moiety are replaced by a PO3H2 function. Assay of cytostatic activity with

  N-（氯乙酰基）氨基膦酸或其酯的Michaelis-Arbuzov反应，然后酸解，可得到中等收率的各种（氨基烷基）膦酸的N-（膦酰基乙酰基）衍生物，包括细胞抑制剂PALA的类似物。天冬氨酸部分中的α-或β-羧基被PO3H2取代。用人KB细胞系的细胞抑制活性的测定表明，用PO 3 H 2取代PALA中的任何COOH基团会导致细胞抑制活性的完全丧失。在该报告中描述的其他[N-（膦酰基乙酰基）氨基]烷基膦酸的情况下也未观察到活性。
• Synthesis and stability of 1-aminoalkylphosphonic acid quaternary ammonium salts
  作者：Anna Brol、Tomasz K. Olszewski

  DOI：10.1039/d1ob00703c

  日期：——

  convenient alkylating agent is reported. During the course of the reaction, phosphonic acid quaternary ammonium derivatives, along with their corresponding monoesters are formed. Subsequent direct acidic hydrolysis of the crude reaction mixture leads to the desired novel N,N,N-trialkyl-N-(1-phosphonoalkyl)ammonium salts with overall yields of up to 88%. The developed protocol is general in scope and the products

  报道了使用 Me 2 SO 4作为方便的烷基化剂在碱性条件下对简单的 1-氨基烷基膦酸进行季铵化的有效方案。在反应过程中，形成膦酸季铵衍生物及其相应的单酯。随后粗反应混合物的直接酸水解产生所需的新的N , N , N-三烷基-N-(1-膦酰基烷基)铵盐，总收率高达 88%。开发的方案在范围上是通用的，产品通过简单的结晶纯化，得到稳定的固体。带有膦基的新型季铵盐通常在酸性和碱性介质中不反应。然而，它们中的一些在碱的存在下会发生霍夫曼消除和取代反应。
• Synthesis of New (3-Aminopyrrolidin-3-yl)phosphonic Acid - A Cucurbitine Analogue - and (3-Aminotetrahydrothiophen-3-yl)phosphonic Acid via Phosphite Addition to Heterocyclic Hydrazones
  作者：Antoine Fadel、Nicolas Rabasso

  DOI：10.1055/s-2008-1067130

  日期：2008.8

  (3-hydrazinopyrrolidin-3-yl)-, (3-hydrazinotetrahydrothiophen-3-yl)-, (3-hydrazinotetrahydrofuran-3-yl)-, and (1-hydrazinocyclopentyl)phosphonates. Cleavage of the hydrazine N-N bonds followed by acidic hydrolysis of the phosphonate functions of the (3-aminoheterocyclopentyl)phosphonates gave the new (3-aminopyrrolidin-3-yl)- and (3-aminotetrahydrothiophen-3-yl)phosphonic acids. This synthesis was achieved

  腙是通过碳环杂环酮与 Denzoyana 甲苯磺酰肼缩合制备的。这些腙与亚磷酸酯进行亲核加成以有效地提供 (3-肼基吡咯烷-3-基)-、(3-肼基四氢噻吩-3-基)-、(3-肼基四氢呋喃-3-基)-和(1-肼基环戊基)膦酸盐. 肼 NN 键断裂，然后酸水解 (3-氨基杂环戊基) 膦酸盐的膦酸盐官能团，得到新的 (3-氨基吡咯烷-3-基)-和 (3-氨基四氢噻吩-3-基)膦酸。该合成是从适当的酮以四步顺序实现的。
• Soroka, Miroslaw, Liebigs Annalen der Chemie, 1990, # 4, p. 331 - 334
  作者：Soroka, Miroslaw

  DOI：——

  日期：——