1-氨基丙基磷酸 | 14047-23-5

• 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-氨基丙基磷酸
• 中文别名: (1-氨基丙基)磷酸
• 英文名称: 1-aminopropanephosphonic acid
• 英文别名: α-aminopropanephosphonic acid；1-aminopropylphosphonic acid；1-Aminopropanphosphonsaeure；(1-Aminopropyl)phosphonate；1-azaniumylpropyl(hydroxy)phosphinate
• CAS: 14047-23-5
• 化学式: C₃H₁₀NO₃P
• mdl: MFCD00015404
• 分子量: 139.091
• InChiKey: DELJNDWGTWHHFA-UHFFFAOYSA-N

物化性质

• 熔点：
  263-268 °C
• 沸点：
  311.9±44.0 °C(Predicted)
• 密度：
  1.373±0.06 g/cm3(Predicted)
• 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)：
  -3.8
• 重原子数：
  8
• 可旋转键数：
  2
• 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
• 安全说明：
  S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2931900090
• 储存条件：
  存放在阴凉干燥处即可。

SDS

Name:	(1-Aminopropyl)phosphonic acid 97% Material Safety Data Sheet
Synonym:	None Known
CAS:	14047-23-5

Section 1 - Chemical Product MSDS Name:(1-Aminopropyl)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#
14047-23-5	(1-Aminopropyl)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# 14047-23-5: 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: Crystalline powder
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 264 - 268 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: C3H10NO3P
Molecular Weight: 139.09

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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# 14047-23-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(1-Aminopropyl)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# 14047-23-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 14047-23-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 14047-23-5 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-氨基丙基磷酸 、 N-苄氧羰基-L-丙氨酸 N-羟基琥珀酰亚胺酯 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Cameron, David G.; Hudson, Harry R.; Pianka, Max, Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 88, # 1-4, p. 15 - 26

  摘要：

  DOI：
• 作为产物：
  描述：

  1-Aminopropylphosphonsaeure-diethylester 在 盐酸 、 溶剂黄146 作用下， 反应 7.0h， 生成 1-氨基丙基磷酸
  参考文献：
  名称：

  1-氨基链烷膦酸。亚磷酸二乙酯加到N-二异丁基铝-亚胺中

  摘要：

  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。

  DOI：

  10.1016/0022-328x(89)85134-4

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。
• 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。
• Use of the dehydrophos biosynthetic enzymes to prepare antimicrobial analogs of alaphosphin
  作者：Despina J. Bougioukou、Chi P. Ting、Spencer C. Peck、Subha Mukherjee、Wilfred A. van der Donk

  DOI：10.1039/c8ob02860e

  日期：——

  enzyme is also tolerant with respect to the amino acid attached to tRNALeu. Using a mutant of leucyl tRNA synthetase that is deficient in its proofreading ability allowed the preparation of a series of aminoacyl-tRNALeu derivatives (Ile, Ala, Val, Met, norvaline, and norleucine). DhpH-C accepted these aminoacyl-tRNA derivatives and condensed the amino acid with l-Ala(P) to form the corresponding phosphonodipeptides

  脱磷生物合成酶DhpH（DhpH-C）的C末端结构域催化Leu-tRNALeu与（R）-1-氨基乙基膦酸酯（丙氨酸的氨基膦酸酯类似物Ala（P））缩合。该反应的产物Leu-Ala（P）是磷酸二肽，一类化合物，以前已被研究用作临床抗生素。在这项研究中，我们表明DhpH-C具有高度的底物耐受性，并且可以将各种氨基膦酸酯（Gly（P），Ser（P），Val（P），1-氨基-丙基膦酸酯和苯基甘氨酸（P））缩合到Leu。而且，该酶对tRNALeu上连接的氨基酸也具有耐受性。使用缺乏校对能力的亮氨酰tRNA合成酶突变体，可以制备一系列氨酰基-tRNALeu衍生物（Ile，Ala，Val，Met，正缬氨酸和正亮氨酸）。DhpH-C接受这些氨基酰基-tRNA衍生物，并将氨基酸与1-Ala（P）缩合形成相应的磷酸二肽。这些肽的一部分显示出抗微生物活性，表明该酶是制备抗微生物肽的通用生物催化剂。我们还研究了来
• One-pot synthesis of α-aminophosphonates via a cascade sequence of allylamine isomerization/hydrophosphonylation
  作者：Liu-Liang Mao、Chen-Chen Li、Qiang Yang、Ming-Xing Cheng、Shang-Dong Yang

  DOI：10.1039/c7cc01391d

  日期：——

  A Rh/Ni-catalyzed cascade sequence of allylamine isomerization and hydrophosphonylation to synthesize [small alpha]-aminophosphonates has been disclosed.

  已经公开了Rh / Ni催化的烯丙胺异构化和氢膦酰化以合成α-氨基膦酸酯的级联序列。