1-氨基-2-甲丙基磷酸 | 66254-55-5

• 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-2-甲丙基磷酸
• 中文别名: (1S)-(-)-(1-氨基-2-甲基丙基)磷酸
• 英文名称: l-(1-amino-2-methylpropyl)phosphonic acid
• 英文别名: <(+)-(S)-1-amino-2-methylpropyl>phosphonic acid；(+)-(S)-(1-amino-2-methylpropyl)phosphonic acid；(S)-1-amino-2-methylpropanephosphonic acid；(S)-Val^P；(S)-H2PO3(HC(CH(CH3)2NH2)；(1S)-(-)-(1-Amino-2-methylpropyl)phosphonic acid；[(1S)-1-amino-2-methylpropyl]phosphonic acid
• CAS: 66254-55-5
• 化学式: C₄H₁₂NO₃P
• 分子量: 153.118
• InChiKey: DGSLPJDIFKVSIB-BYPYZUCNSA-N

物化性质

• 熔点：
  272-277 °C(lit.)
• 比旋光度：
  -1.0° (20/D) (c=1 ,1N NaOH)
• 沸点：
  302.9±44.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  在常温常压下稳定，应远离氧化剂。

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  9
• 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
• 海关编码：
  2931900090

SDS

Name:	(1S)-(-)-(1-Amino-2-methylpropyl)phosphonic acid Material Safety Data Sheet
Synonym:	None Known
CAS:	66254-55-5

Section 1 - Chemical Product MSDS Name:(1S)-(-)-(1-Amino-2-methylpropyl)phosphonic acid Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
66254-55-5	(1S)-(-)-(1-Amino-2-methylpropyl)phosp	100	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.
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.
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.
Avoid contact with skin and eyes. 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# 66254-55-5: 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: Crystals
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 270 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: C4H12NO3P
Molecular Weight: 153.12

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
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# 66254-55-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(1S)-(-)-(1-Amino-2-methylpropyl)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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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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# 66254-55-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 66254-55-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 66254-55-5 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：

  sodium molybdate 、 1-氨基-2-甲丙基磷酸 以 水 为溶剂， 生成 (S,S)-Na2[Mo5O15(O3P(CH(CH(CH3)2)(NH3)]2
  参考文献：
  名称：

  手性Strandberg型钼酸盐[（RPO3）2Mo5O15] 2-作为分子胶凝剂：具有增强的光学活性的自组装纤维状纳米结构。

  摘要：

  DOI：

  10.1002/anie.200801629
• 作为产物：
  描述：

  (+)-(S)-diethyl (1-amino-2-methylpropyl)phosphonate 在 盐酸 作用下， 以 水 为溶剂， 反应 15.0h， 以85%的产率得到1-氨基-2-甲丙基磷酸
  参考文献：
  名称：

  N-糖基硝酮的亲核加成。α-氨基膦酸的不对称合成† ‡

  摘要：

  这解释了的1,3-偶极环加成的非对映选择性的假说Ñ -glycosylnitrones 1 - 3通向5,5-二取代的异恶唑烷4 - 6的动能端基异构效应的基础上预测，亲核试剂应该添加到ñ -具有高度非对映选择性的糖基硝酮。为了检验该预测，已经研究了锂和二烷基亚磷酸锂向由肟9和（苄氧基）乙醛制备的结晶（Z）-硝基1的亲核加成反应。亚磷酸锂的添加使N-glycosyl- Ñ -hydroxyaminophosphonates 12 - 16（78-92 DE％）以高收率（方案4） 。亚磷酸钾的添加显示出低得多的非对映选择性。糖苷切割，氢解，和脱烷基化的12 - 16得到（+） - （小号）-phosphoserine（+） - 19（34-45％来自9）。通过N-（3,3,3-三氟-2-甲氧基-2-甲氧基-2-苯基丙酰）衍生物24的X射线分析证实了其绝对构型。类似地，结晶的硝酮25得到N-糖

  DOI：

  10.1002/hlca.19850680629

文献信息

• Nucleophilic Additions toN-Glycosylnitrones. Asymmetric Synthesis of ?-Aminophosphonic Acids
  作者：Rolf Huber、Andreas Knierzinger、Jean-Pierre Obrecht、Andrea Vasella

  DOI：10.1002/hlca.19850680629

  日期：1985.9.25

  The hypothesis which explains the diastereoselectivity of the 1,3-dipolar cycloaddition of the N-glycosylnitrones 1–3 leading to the 5,5-disubstituted isoxazolidines 4–6 on the basis of a kinetic anomeric effect predicts that nucleophiles should add to N-glycosylnitrones with a high degree of diastereoselectivity. To test this prediction, the nucleophilic addition of lithium and potassium dialkylphosphites

  这解释了的1,3-偶极环加成的非对映选择性的假说Ñ -glycosylnitrones 1 - 3通向5,5-二取代的异恶唑烷4 - 6的动能端基异构效应的基础上预测，亲核试剂应该添加到ñ -具有高度非对映选择性的糖基硝酮。为了检验该预测，已经研究了锂和二烷基亚磷酸锂向由肟9和（苄氧基）乙醛制备的结晶（Z）-硝基1的亲核加成反应。亚磷酸锂的添加使N-glycosyl- Ñ -hydroxyaminophosphonates 12 - 16（78-92 DE％）以高收率（方案4） 。亚磷酸钾的添加显示出低得多的非对映选择性。糖苷切割，氢解，和脱烷基化的12 - 16得到（+） - （小号）-phosphoserine（+） - 19（34-45％来自9）。通过N-（3,3,3-三氟-2-甲氧基-2-甲氧基-2-苯基丙酰）衍生物24的X射线分析证实了其绝对构型。类似地，结晶的硝酮25得到N-糖
• Nucleophilic additions toN-glycosylnitrones part IV Asymmetric synthesis ofN-hydroxy-?-aminophosphonic and ?-aminophosphonic acids
  作者：Rolf Huber、Andrea Vasella

  DOI：10.1002/hlca.19870700603

  日期：1987.9.23

  proved inert towards the phosphite anions, they reacted with P(OSiMe3)3 under catalysis by Lewis acids. Thus, P(OSiMe3)3 reacted with the crystalline (Z)-N-glycosylnitrones 2 and 8 to give the optically active N-hydroxy-α-aminophosphonic acids 4 and 10, respectively, and hence the α-aminophosphonic acids 5 and 11 in yields up to 92% and with an enantiomeric excess (e.e.) up to 97% (Scheme 1). The absolute

  添加亚磷酸阴离子和三（三甲基硅烷基）亚磷酸酯（P（OSiMe 3）3），以Ñ -glycosyl- Ç -arylnitrones检查。尽管这些硝酮对亚磷酸根阴离子呈惰性，但它们在路易斯酸催化下与P（OSiMe 3）3反应。因此，P（OSiMe 3）3与结晶的（Z）-N-糖基硝酮2和8反应，得到旋光的N-羟基-α-氨基膦酸4和10。因此，α-氨基膦酸5和11的产率最高为92％，对映体过量（ee）最高为97％（方案1）。膦酸酯的绝对构型取决于性质，在一种情况下取​​决于催化剂的量（图）。在HCIO 4或Zn（OTF）2催化下，将p（OSiMe 3）3添加到2中，在两种情况下均得到（+）-（R）-苯基磷酸甘氨酸5（光学纯度分别为79–84和90–93％）。光学纯度（op）几乎不受这些催化剂的量（0.02-； 1当量）的影响。但是，用ZnCl 2催化可得到痕量的催化剂，（-）-（S）-5（op 79％），而等摩尔量的ZnCl
• New .alpha.-amino phosphonic acid derivatives of vinblastine: chemistry and antitumor activity
  作者：Gilbert Lavielle、Patrick Hautefaye、Corinne Schaeffer、Jean A. Boutin、Claude A. Cudennec、Alain Pierre

  DOI：10.1021/jm00111a012

  日期：1991.7

  A series of new amino phosphonic acid derivatives of vinblastine (1, VLB) has been synthesized and tested in vitro and in vivo for antitumor activity. The compounds were obtained from O4-deacetyl-VLB azide. All of the new products studied were capable of inhibiting tubulin polymerization in vitro. The most potent antitumor compounds bore an alkyl substituent on the phosphonate. In these compounds,

  合成了长春碱的一系列新的氨基膦酸衍生物（1，VLB），并在体内和体外测试了其抗肿瘤活性。该化合物获自O4-脱乙酰基-VLB叠氮化物。研究的所有新产品均具有体外抑制微管蛋白聚合的能力。最有效的抗肿瘤化合物在膦酸酯上带有烷基取代基。在这些化合物中，抗肿瘤活性强烈取决于膦酸酯的立体化学。膦酸酯（1S）-[1-[（O4-脱乙酰基-3-脱（甲氧基羰基）vincaleukoblastin-3-基]羰基]氨基] -2-甲基丙基]膦酸二乙酯对癌细胞系均表现出显着活性。体外和体内。
• A highly convenient route to optically pure α-aminophosphonic acids
  作者：Robert Hamilton、Brian Walker、Brian J. Walker

  DOI：10.1016/0040-4039(95)00750-7

  日期：1995.6

  Pure diasteriomers, obtained simply and directly by reaction of hypophosphorous acid salts of (R)(+) or (S)(−) - N-α-methylbenzylamine with aldehydes, can be simultaneously deprotected and oxidised in one step to provide a highly convenient synthesis of α - aminophosphonic acids in high optical purity.

  通过（R）（+）或（S）（-）-N-α-甲基苄基胺的次磷酸盐与醛反应简单而直接获得的纯非对映异构体，可以在一个步骤中同时脱保护和氧化，从而提供了高度便利的条件光学纯度高的α-氨基膦酸的合成。
• Kafarski, Pawel; Lejczak, Barbara; Szewczyk, Jerzy, Canadian Journal of Chemistry, 1983, vol. 61, p. 2425 - 2430
  作者：Kafarski, Pawel、Lejczak, Barbara、Szewczyk, Jerzy

  DOI：——

  日期：——