(1-氨基戊基)磷酸 | 13138-37-9

• 物质功能分类: 有机原料 - 有机膦化合物
• 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-氨基戊基)磷酸
• 中文别名: 1-氨戊基膦酸
• 英文名称: 1-amino-pentylphosphonic acid
• 英文别名: α-aminopentanephosphonic acid；[(R,S)-1-aminopentyl]phosphonic acid；(R,S)-1-aminopentanephosphonic acid；1-aminopentanephosphonic acid；1-aminopentylphosphonic acid；1-Aminopentylphosphonsaeure；(1-Aminopentyl)phosphonic acid
• CAS: 13138-37-9
• 化学式: C₅H₁₄NO₃P
• mdl: MFCD02093906
• 分子量: 167.145
• InChiKey: NXTPDFMZKSLVRK-UHFFFAOYSA-N

物化性质

• 熔点：
  267-269 °C
• 沸点：
  322.4±44.0 °C(Predicted)
• 密度：
  1.244±0.06 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)：
  -2.9
• 重原子数：
  10
• 可旋转键数：
  4
• 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：
  S37/39

SDS

Name:	(1-Aminopentyl)phosphonic acid 97% Material Safety Data Sheet
Synonym:	None Known
CAS:	13138-37-9

Section 1 - Chemical Product MSDS Name:(1-Aminopentyl)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#
13138-37-9	(1-Aminopentyl)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# 13138-37-9: 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: Crystalline powder
Color: white to off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 267 - 269 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:
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# 13138-37-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(1-Aminopentyl)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# 13138-37-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 13138-37-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 13138-37-9 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-氨基戊基)磷酸 在 三乙烯二胺 、 sodium carbonate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 24.0h， 生成 methyl (2S)-2-[({[(R,S)-1-benzyloxycarbonylaminopentyl(benzyloxy)phosphoryl]oxy}acetyl)amino]-3-methylbutanoate
  参考文献：
  名称：

  有效合成正亮氨酸衍生的磷酸节点肽

  摘要：

  在本工作中，我们详细描述了模仿肽序列Nle-Gly（Ala）和Nle-Gly（Ala）-Val的正亮氨酸衍生的磷酸肽的有效溶液合成。最有效的策略涉及苄基的使用。通过BOP催化的N -Cbz保护的正亮氨酸的膦酸酯衍生物的单苄基酯与衍生化的1-乳酸或乙醇酸的羟基部分的偶联，实现了合成。随后，通过一步钯催化的氢解以良好的产率实现了产物的完全脱保护。我们还制备了Fmoc-Nle-Ψ[PO（OH）O] -CH 2-COOH合成子，并证明该前体是用于固相合成含半胱氨酸的膦酰肽的合适构件。

  DOI：

  10.1016/j.tet.2009.05.051
• 作为产物：
  描述：

  1-acetylaminopentylphosphonic acid 在 盐酸 、 水 作用下， 反应 8.0h， 生成 (1-氨基戊基)磷酸
  参考文献：
  名称：

  有机合成中的三苯甲基胺（triphenylmethylamine）；三、在 N-（三苯基甲基）烷胺与三氯化磷在乙酸中或与在乙酸酐中的膦酸反应中合成 1-氨基烷基膦酸。

  摘要：

  三氯化磷在乙酸中或在乙酸酐中的膦酸（亚磷酸）与 N-（三苯基甲基）链烷胺反应生成 1-乙酰氨基烷基膦酸 1a-j，水解后生成 1-氨基烷基膦酸 2a-j，收率良好。

  DOI：

  10.3998/ark.5550190.0011.b29

文献信息

• Enkephalin analogs and a process for the preparation thereof
  申请人：Richter Gedeon Vegyeszeti Gyar RT

  公开号：US04339440A1

  公开（公告）日：1982-07-13

  The invention relates to new enkephalin analogues of the general formula (I), Tyr-X-Gly-Phe-Y (I) wherein Tyr, Gly and Phe represent L-tyrosyl, glycyl and L-phenylalanyl residue, respectively, X is glycyl residue or a D-.alpha.-aminocarboxylic acid residue with a lower alkyl, lower thioalkyl or phenyl-(lower)-alkyl side chain, and Y is the residue of an L, D or DL-.alpha.-aminophosphonic acid or L, D or DL-.alpha.-aminosulfonic acid, each having a lower alkyl side chain, and salts thereof. These compounds are prepared according to the invention so that an L-, D- or DL-.alpha.-aminophosphonic acid or an L-, D- or DL-.alpha.-aminosulfonic acid, each bearing a lower alkyl side chain, is coupled in the proper order, as defined by formula (I), with the amino acids and/or peptide fragments each having a removable protecting group on the terminal amino group, the protecting group is split off from the terminal amino group, and the free peptide is isolated as such or in the form of its salt. The new compounds according to the invention selectively modify the catecholamine content of the central nucleus of amygdala, thus they may specifically influence the following functions: food intake, emotionality, social behavior, learning and memory processes.

  该发明涉及一般式(I)的新的脑啡肽类似物，其中Tyr、Gly和Phe分别代表L-酪氨酰基、甘氨酰基和L-苯丙氨酰基残基，X是甘氨酰基或具有较低烷基、较低硫代烷基或苯基-(较低)-烷基侧链的D-α-氨基羧酸残基，Y是具有较低烷基侧链的L、D或DL-α-氨基膦酸或L、D或DL-α-氨基磺酸残基，以及它们的盐。根据该发明制备这些化合物，使得L、D或DL-α-氨基膦酸或L、D或DL-α-氨基磺酸，每个带有较低烷基侧链，按照式(I)所定义的正确顺序与氨基酸和/或肽段偶联，每个具有可去保护基的末端氨基团，保护基从末端氨基团上脱落，游离肽被单独分离或以其盐的形式存在。根据该发明的新化合物选择性地修改杏仁核中枢的儿茶酚胺含量，因此它们可能特异地影响以下功能：食物摄入、情绪、社会行为、学习和记忆过程。
• 1-Aminoalkanephosphonic acids. Addition of diethyl phosphite to N-diisobutylaluminio-aldimines
  作者：Zbigniew H. Kudzin、Michał W. Majchrzak

  DOI：10.1016/0022-328x(89)85134-4

  日期：1989.11

  A new route to 1-aminoalkanephosphonic acids starting from nitriles has been elaborated. The nitriles are reduced by Dibal-H into imine derivatives; addition with diethyl phosphite gives the corresponding 1-aminoalkanephosphonates. Hydrolysis of latter compounds gives the 1-aminoalkanephosphonic acids.

  已经阐明了从腈开始合成1-氨基链烷膦酸的新途径。腈被Dibal-H还原为亚胺衍生物。用亚磷酸二乙酯加成得到相应的1-氨基链烷膦酸酯。后一种化合物的水解得到1-氨基链烷膦酸。
• Reactivity of aminophosphonic acids. Oxidative dephosphonylation of 1-aminoalkylphosphonic acids by aqueous halogens
  作者：Józef Drabowicz、Frank Jordan、Marcin H. Kudzin、Zbigniew H. Kudzin、Christian V. Stevens、Paweł Urbaniak

  DOI：10.1039/c5dt03083h

  日期：——

  reactions of 1-aminoalkylphosphonic acids with bromine–water, chlorine–water and iodine–water were investigated. The formation of phosphoric(V) acid, as a result of a halogen-promoted cleavage of the Cα–P bond, accompanied by nitrogen release, was observed. The dephosphonylation of 1-aminoalkylphosphonic acids was found to occur quantitatively. In the reactions of 1-aminoalkylphosphonic acids with other

  研究了1-氨基烷基膦酸与溴水，氯水和碘水的反应。磷酸（形成V）酸，作为℃的卤素促进的切割的结果α -P键，伴随着氮气释放，进行了观察。发现1-氨基烷基膦酸的去膦酰化定量地发生。在31 P NMR研究的1-氨基烷基膦酸与其他卤素-水试剂的反应中，还观察到Cα - P键的断裂，溴和氯的反应速率相当，而碘的反应速率慢得多。
• Synthesis of norleucine-derived phosphonopeptides
  作者：Jan Pícha、Miloš Buděšínský、Miloslav Šanda、Jiří Jiráček

  DOI：10.1016/j.tetlet.2008.05.028

  日期：2008.7

  The synthesis of norleucine-derived phosphonopeptides was achieved by BOP-catalyzed coupling of the monobenzyl ester of a N-CBz-protected phosphonate derivative of norleucine with hydroxyl moieties of derivatized lactic or glycolic acids. The complete deprotection of the product esters/carbamates was achieved in good yields by one-step Pd-catalyzed hydrogenolysis.

  通过BOP催化的N -CBz保护的正亮氨酸的膦酸酯衍生物的单苄基酯与衍生化的乳酸或乙醇酸的羟基部分的偶联，实现了正亮氨酸衍生的磷酸肽的合成。通过一步钯催化的氢解，以良好的产率实现了产物酯/氨基甲酸酯的完全脱保护。
• 1-Aminoalkanephosphonates. Part II. A Facile Conversion of 1-Aminoalkanephosphonic Acids into 0,0-Diethyl 1-aminoalkanephosphonates
  作者：Zbigniew H. Kudzin、Piotr Łyżwa、Jerzy Łuczak、Grzegorz Andrijewski

  DOI：10.1055/s-1997-1508

  日期：1997.1

  1-(N-Trifluoroacetylamino)alkanephosphonate 0,0-diethyl esters 2 C, obtained from parent 1-aminoalkanephosphonic acids 1, have been selectively deprotected on the amino function affording 0,0-diethyl 1-aminoalkanephosphonates 3. Protonation constants of all amino esters 3 synthesized have been determined by potentiometric titration.

  从母体 1-氨基烷基膦酸 1 中得到的 1-(N-三氟乙酰氨基)烷基膦酸 0,0-二乙酯 2 C 在氨基官能团上进行选择性脱保护，得到 0,0-二乙基 1-氨基烷基膦酸 3。通过电位滴定法测定了合成的所有氨基酯 3 的质子常数。