1-氨基丙基磷酸 | 98048-99-8

• 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: (1S)-(+)-(1-氨丙基)膦酸；(1S)-(+)-(1-氨基丙基)磷酸；(S)-(+)-(1-氨丙基)膦酸
• 英文名称: (S)-(1-aminopropyl)phosphonic acid
• 英文别名: (+)-1-aminopropylphosphonic acid；(1S)-(+)-(1-Aminopropyl)phosphonic acid；[(1S)-1-aminopropyl]phosphonic acid
• CAS: 98048-99-8
• 化学式: C₃H₁₀NO₃P
• 分子量: 139.091
• InChiKey: DELJNDWGTWHHFA-VKHMYHEASA-N

物化性质

• 熔点：
  265-269 °C(lit.)
• 比旋光度：
  +16.5 degrees (20/D) (c=2, 1N NaOH)
• 稳定性/保质期：
  常温常压下稳定，应避免与强氧化剂接触。

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：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2931900090

SDS

Name:	(s)-(1-aminopropyl)phosphonic acid Material Safety Data Sheet
Synonym:
CAS:	98048-99-8

Section 1 - Chemical Product MSDS Name:(s)-(1-aminopropyl)phosphonic acid Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
98048-99-8	(S)-(1-Aminopropyl)phosphonic acid		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.
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.

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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.

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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.
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.

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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.

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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# 98048-99-8: 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.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystals
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 260 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C3H10NO3P
Molecular Weight: 139.09

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, thermal decomposition may produce toxic fumes of phosphorous oxides and/or phosphine.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 98048-99-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(S)-(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# 98048-99-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 98048-99-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 98048-99-8 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

• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 21.0h， 以0.16 g的产率得到1-氨基丙基磷酸
  参考文献：
  名称：

  腈向 1-氨基膦酸的转化和高对映体过量的磷同型半胱氨酸的制备

  摘要：

  图形摘要摘要将多种腈还原为醛亚胺的二异丁基铝盐，向其中加入亚磷酸二异丙酯。相应的 1-氨基膦酸酯被脱保护得到外消旋 1-氨基膦酸或与 Boc2O 反应生成 N-Boc 保护的 1-氨基膦酸酯。2-苄硫基-1-(叔丁氧基羰基氨基)丙基膦酸酯的对映异构体通过手性HPLC从外消旋体获得并转化为(R)-和(S)-高半胱氨酸、(R)-和(S)-的膦酸类似物2-氨基丁酸和(S)-甲硫氨酸，通过手性HPLC测定，所有ee>97%。

  DOI：

  10.1080/10426507.2017.1284844

文献信息

• A versatile asymmetric synthesis of α-amino α-alkyl-phosphonic acids of high enantiomeric purity
  作者：Stephen Hanessian、Youssef L. Bennani

  DOI：10.1016/s0040-4039(00)97092-8

  日期：1990.1

  A general protocol for the synthesis of α-amino-α- alkyl phosphonic acids in either enantiomeric form is described based on the alkylation of chiral bicyclic phosphonamides derived from (R,R)- and (S,S)-1,2-diaminocyclohexane.

  基于衍生自（R，R）-和（S，S）-1,2-二氨基环己烷的手性双环膦酰胺的烷基化，描述了以对映体形式合成α-氨基-α-烷基膦酸的一般方案。
• Asymmetric Synthesis of α-Amino Phosphonic Acids by Diastereoselective Addition of Trimethyl Phosphite onto Chiral Oxazolidines¹
  作者：Catherine Maury、Tawfik Gharbaoui、Jacques Royer、Henri-Philippe Husson

  DOI：10.1021/jo960020c

  日期：1996.1.1

  A simple and general asymmetric synthesis of alpha-amino phosphonic acids is described. The method involves the highly selective addition of trialkyl phosphite onto various chiral oxazolidines. Oxazaphosphorinanes thus obtained with an excellent diastereoselectivity furnish the corresponding (S)-alpha-substituted amino phosphonic acids in good overall yields and high ee (77-->97%) after simple deprotection

  描述了α-氨基膦酸的简单且一般的不对称合成。该方法涉及将亚磷酸三烷基酯高度选择性地添加到各种手性恶唑烷上。如此获得的具有出色的非对映选择性的草氮磷杂环丁烷在简单的脱保护后以良好的总收率和较高的ee（77-> 97％）提供了相应的（S）-α-取代的氨基膦酸。
• A simple and general method for the asymmetric synthesis of α-aminophosphonic acids
  作者：Catherine Maury、Jacques Royer、Henri-Philippe Husson

  DOI：10.1016/s0040-4039(00)60023-0

  日期：1992.10

  A simple and general method for the asymmetric synthesis of α-aminophosphonic acids is described. A chiral phosphonate prepared in one step from R-(−)-phenylglycinol was alkylated with good diastereoselectivity using different electrophiles.

  描述了一种不对称合成α-氨基膦酸的简单通用方法。使用不同的亲电试剂，以良好的非对映选择性将由R-（-）-苯基甘氨醇一步制备的手性膦酸酯烷基化。
• Electrophilic Amination and Azidation of Chiral α-Alkyl Phosphonamides: Asymmetric Syntheses of α-Amino α-Alkyl Phosphonic Acids†
  作者：Stephen Hanessian、Youssef L. Bennani

  DOI：10.1055/s-1994-25679

  日期：——

  Stereoselective electrophilic aminations of chiral non racemic α-alkyl phosphonamides, derived from N,N′-dimethyl (R,R)-1,2-diamino-cyclohexane, proceed with moderate to excellent enantioselectivities. The products are hydrolyzed and reduced to the corresponding α-alkyl α-amino phosphonic acids. The sense of asymmetric induction was confirmed by X-ray crystal structure analysis.

  由 N,N′-二甲基 (R,R)-1,2-二氨基环己烷衍生的手性非外消旋δ-烷基膦酰胺的立体选择性亲电胺化反应，具有中等到极好的对映选择性。产物被水解并还原成相应的δ-烷基δ-氨基膦酸。X 射线晶体结构分析证实了不对称诱导的意义。
• Conversion of nitriles to 1-aminophosphonic acids and preparation of phosphahomocysteines of high enantiomeric excess
  作者：Renzhe Qian、Jeannie Horak、Friedrich Hammerschmidt

  DOI：10.1080/10426507.2017.1284844

  日期：2017.6.3

  1-aminophosphonic acids or reacted with Boc2O to yield N-Boc-protected 1-aminophosphonates. The enantiomers of 2-benzylthio-1-(t-butoxycarbonylamino)propylphosphonate were obtained from the racemate by chiral HPLC and converted to phosphonic acid analogs of (R)- and (S)-homocysteine, (R)- and (S)-2-aminobutyric acid and (S)-methionine, all of ee >97% as determined by chiral HPLC.

  图形摘要摘要将多种腈还原为醛亚胺的二异丁基铝盐，向其中加入亚磷酸二异丙酯。相应的 1-氨基膦酸酯被脱保护得到外消旋 1-氨基膦酸或与 Boc2O 反应生成 N-Boc 保护的 1-氨基膦酸酯。2-苄硫基-1-(叔丁氧基羰基氨基)丙基膦酸酯的对映异构体通过手性HPLC从外消旋体获得并转化为(R)-和(S)-高半胱氨酸、(R)-和(S)-的膦酸类似物2-氨基丁酸和(S)-甲硫氨酸，通过手性HPLC测定，所有ee>97%。