(1-氨基-甲基苯)磷酸 | 18108-22-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (1-氨基-甲基苯)磷酸
• 英文名称: 1-amino-1-phenylmethylphosphonic acid
• 英文别名: amino(phenyl)methylphosphonic acid；1-aminobenzylphosphonic acid；α-aminobenzylphosphonic acid；(α-Amino-benzyl)-phosphonsaeure；phosphonophenylglycine；1-Amino-1-phenylmethanphosphonsaeure；Aminophenylmethanphosphonsaeure；NSC 133811；[Amino(phenyl)methyl]phosphonic acid
• CAS: 18108-22-0
• 化学式: C₇H₁₀NO₃P
• mdl: MFCD00014809
• 分子量: 187.135
• InChiKey: ZKFNOUUKULVDOB-UHFFFAOYSA-N

物化性质

• 熔点：
  254-257 °C
• 沸点：
  407.9±55.0 °C(Predicted)
• 密度：
  1.446±0.06 g/cm3(Predicted)
• 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)：
  -3.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 储存条件：
  存于阴凉干燥处。

SDS

Name:	(1-Amino-1-phenylmethyl)phosphonic acid 97% Material Safety Data Sheet
Synonym:	alpha-Aminobenzylphosphonic aci
CAS:	18108-22-0

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

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
18108-22-0	(1-Amino-1-phenylmethyl)phosphonic aci	97%	unlisted

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

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
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.
Chronic:
Not available.

---

Section 4 - FIRST AID MEASURES
Eyes: 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.
Ingestion:
Get medical aid. 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.
Notes to Physician:
Treat symptomatically and supportively.

---

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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

---

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.

---

Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

---

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# 18108-22-0: Personal Protective Equipment Eyes: Not available.
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.

---

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: 283 - 285 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: C7H10NO3P
Molecular Weight: 187.13

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable.
Conditions to Avoid:
Incompatible materials.
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

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 18108-22-0: SZ6562500 LD50/LC50:
Not available.
Carcinogenicity:
(1-Amino-1-phenylmethyl)phosphonic acid - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

---

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# 18108-22-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 18108-22-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 18108-22-0 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (1-氨基-甲基苯)磷酸 在 sodium hydroxide 、 氢溴酸 、 溶剂黄146 作用下， 生成 diethyl 1-aminophenylmethylphosphonate
  参考文献：
  名称：

  含氨基膦酸的肽的合成

  摘要：

  在水性和非水性介质中均制备了包含C端α-氨基苄基膦酸的二肽。还讨论了制备含α-氨基膦酸的肽所必需的中间体的合成。描述了通过二环己基碳二亚胺，酰氯和1-乙氧基羰基-2-乙氧基-1,2-二氢喹啉偶联氨基膦酸和氨基羧酸的相似性和区别。

  DOI：

  10.1002/jps.2600630711
• 作为产物：
  描述：

  苯甲醛吖嗪 生成 (1-氨基-甲基苯)磷酸
  参考文献：
  名称：

  Rachon,J.; Wasielewski,C., Roczniki Chemii, 1975, vol. 49, p. 397 - 402

  摘要：

  DOI：

文献信息

• A Methylidene Group in the Phosphonic Acid Analogue of Phenylalanine Reverses the Enantiopreference of Binding to Phenylalanine Ammonia-Lyases
  作者：Zsófia Bata、Renzhe Qian、Alexander Roller、Jeannie Horak、László Csaba Bencze、Csaba Paizs、Friedrich Hammerschmidt、Beáta G. Vértessy、László Poppe

  DOI：10.1002/adsc.201700428

  日期：2017.6.19

  formed prosthetic 3,5-dihydro-4-methylidene-5H-imidazol-5-one (MIO) group. MIO enzymes catalyze the stereoselective synthesis of α- or β-amino acid enantiomers, making these chemical processes environmentally friendly and affordable. Characterization of novel inhibitors enables structural understanding of enzyme mechanism and recognizes promising herbicide candidates as well. The present study found that

  芳香族氨基酸氨裂合酶和芳香族氨基酸2,3-氨基变位酶含有翻译后形成的人工3,5-二氢-4-亚甲基-5 H-imidazol-5-one（MIO）组。MIO酶催化α-或β-氨基酸对映异构体的立体选择性合成，从而使这些化学过程对环境友好且负担得起。新型抑制剂的表征使人们对酶的机理有了结构上的了解，并认识到有希望的除草剂候选物。本研究发现，天然底物苯丙氨酸的氨基膦酸类似物的对映体和在β位带有亚甲基的新型衍生物均抑制了代表MIO酶的苯丙氨酸解氨酶（PAL）。X射线方法明确地确定了所有测试对映异构体在合成过程中的绝对构型。酶动力学测量表明，亚甲基取代的底物类似物的对映异构体与天然1-苯丙氨酸是最强的抑制剂。等温滴定热法（ITC）确认了结合常数，并提供了配体结合的热力学驱动力的详细分析。分子对接表明（R）-和（S）-对映异构体的结合可以通过镜像堆积来实现。
• Studies on Organophosphorus Compounds XXVIII. An Improved Synthetic Route to 1-Amino-Substituted Benzyl Phosphonic and -Phosphinic Acids
  作者：Chengye Yuan、Youmao Qi

  DOI：10.1055/s-1988-27610

  日期：——

  An improved method for the synthesis of 1-aminosubstituted benzyl phosphonic and -phosphinic acids under mild conditions is described. It consists of the reaction of diphenoxy chlorophosphine (1) or dichlorophenylphosphine (6) with substituted benzaldehydes 2 and a phosphoramidate 3 in the presence of a Lewis acid, followed by selective cleavage of the protective group of the resultant 1-(phosphorylamino)-substituted benzylphosphonate 4 or phosphinate 7, 9. A tentative reaction mechanism is postulated.

  描述了一种在温和条件下合成1-氨基取代的苯甲基膦酸和膦酸酯的改进方法。该方法包括在路易斯酸存在下，二苯氧基氯膦（1）或二氯苯基膦（6）与取代苯甲醛（2）和膦酰胺酸酯（3）反应，随后选择性断裂所得的1-（膦酰胺基）-取代苯甲基膦酸酯（4）或膦酸酯（7, 9）的保护基团。推测了可能的反应机制。
• 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。
• 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。
• [EN] THIENOPYRIMIDINE INHIBITORS OF FARNESYL AND/OR GERANYLGERANYL PYROPHOSPHATE SYNTHASE<br/>[FR] INHIBITEURS THIÉNOPYRIMIDINE DE FARNÉSYL ET/OU DE GÉRANYLGÉRANYL PYROPHOSPHATE SYNTHASE
  申请人：UNIV MCGILL

  公开号：WO2014078957A1

  公开（公告）日：2014-05-30

  The present invention relates to novel compounds, compositions containing same and methods for inhibiting human farnesyl pyrophosphate synthase or for the treatment or prevention of disease conditions using said compounds;

  本发明涉及新化合物、含有该化合物的组合物以及通过抑制人类法尼基焦磷酸合酶或使用该化合物治疗或预防疾病症状的方法；