正十二烷基磷酸 | 5137-70-2

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: 正十二烷基磷酸
• 中文别名: 正十二烷基膦酸；十二烷基磷酸；十二烷基膦酸；1-十二烷基膦酸
• 英文名称: dodecylphosphonic acid
• 英文别名: n-dodecylphosphonic acid；1-dodecylphosphonic acid；DDPA；n-dodecanephosphonic acid
• CAS: 5137-70-2
• 化学式: C₁₂H₂₇O₃P
• mdl: MFCD00015832
• 分子量: 250.318
• InChiKey: SVMUEEINWGBIPD-UHFFFAOYSA-N

物化性质

• 熔点：
  68-70°C
• 沸点：
  283°C (estimate)
• 密度：
  0.9360 (estimate)
• LogP：
  2.485 at 25℃
• 稳定性/保质期：
  在常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• TSCA：
  Yes
• 危险等级：
  8
• 危险品运输编号：
  UN3261
• 海关编码：
  2931900090
• 包装等级：
  III
• WGK Germany：
  3
• 危险类别：
  8
• 危险性防范说明：
  P234,P260,P264,P280,P301+P330+P331+P310,P303+P361+P353+P310+P363,P304+P340+P310,P305+P351+P338+P310,P390,P405,P406,P501
• 危险性描述：
  H290,H314
• 储存条件：
  请将药品存放在避光、阴凉干燥的地方，并密封保存。

SDS

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Section 1: Product Identification
Chemical Name: n-Dodecylphosphonic acid, min. 97%
CAS Registry Number: 5137-70-2
Formula: CH3(CH2)11P(O)(OH)2
EINECS Number: 225-897-8
Chemical Family: organic phosphonic acid
Synonym: 1-Dodecanephosphonic acid

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 5137-70-2 100% no data no data

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Section 3: Hazards Identification
Emergency Overview: Irritating to skin, eyes and respiratory tract.
Primary Routes of Exposure: Inhalation, skin, eyes
Eye Contact: Dust causes moderate to severe irritation of the eyes.
Skin Contact: Causes irritation to the skin
Inhalation: Causes irritation to the nose, mucous membranes and respiratory tract
Ingestion: No information on the physiological effects of ingestion. May be harmful if swallowed.
Acute Health Affects: Irritating to skin, eyes and respiratory tract.
Chronic Health Affects: No information available on long-term chronic effects
NTP: No
IARC: No
OSHA: No

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SECTION 4: First Aid Measures
Immediately flush the eyes with copious amounts of water for at least 10-15 minutes. A victim may need
Eye Exposure:
assistance in keeping their eye lids open. Get immediate medical attention.
Wash the affected area with water. Remove contaminated clothes if necessary. Seek medical assistance if
Skin Exposure:
irritation persists.
Remove the victim to fresh air. Closely monitor the victim for signs of respiratory problems, such as difficulty
Inhalation:
in breathing, coughing, wheezing, or pain. In such cases seek immediate medical assistance.
Seek medical attention immediately. Keep the victim calm. Give the victim water (only if conscious). Induce
Ingestion:
vomiting only if directed by medical personnel.

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SECTION 5: Fire Fighting Measures
Flash Point: no data
Autoignition Temperature: no data
Explosion Limits: no data
Extinguishing Medium: carbon dioxide, dry chemical or foam
If this product is involved in a fire, fire fighters should be equipped with a NIOSH approved positive pressure
Special Fire Fighting Procedures:
self-contained breathing apparatus and full protective clothing.
Hazardous Combustion and If involved in a fire, this material may emit irritating organic fumes
Decomposion Products:
Unusual Fire or Explosion Hazards: No unusual fire or explosion hazards

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SECTION 6: Accidental Release Measures
Small spills can be mixed with vermiculite, sodium carbonate or other suitable non-combustible adsorbent and
Spill and Leak Procedures:
swept up.

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SECTION 7: Handling and Storage
Handling and Storage: Store in a tightly sealed container in a cool, dry place.

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SECTION 8: Exposure Controls and Personal Protection
Eye Protection: Always wear approved safety glasses when handling a chemical substance in the laboratory.
Skin Protection: Wear protective clothing and gloves. Consult with glove manufacturer to determine the proper type of glove.
Ventilation: It is imperative that this material be handled in an efficient fume hood.
If ventilation is not available a respirator should be worn. The use of respirators requires a Respirator
Respirator:
Protection Program to be in compliance with 29 CFR 1910.134.
Ventilation: It is imperative that this material be handled in an efficient fume hood.
Additional Protection: No additional protection required.

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SECTION 9: Physical and Chemical Properties
Color and Form: white to off-white powder
Molecular Weight: 250.31
Melting Point: 96-98°
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: not determined
Solubility in Water: insoluble

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SECTION 10: Stability and Reactivity
Stability: air and moisture stable
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: none
Incompatibility: oxidizing agents
Decomposition Products: carbon dioxide, carbon monoxide and organic fumes

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SECTION 11: Toxicological Information
RTECS Data: Intraperitoneal(mouse); LDLo: 500mg/kg.
Carcinogenic Effects: no data
Mutagenic Effects: no data
Tetratogenic Effects: no data

---

SECTION 12: Ecological Information
Ecological Information: No information available

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SECTION 13: Disposal Considerations
Disposal: Dispose of according to local, state and federal regulations

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SECTION 14: Transportation
Shipping Name (CFR): Non-hazardous
Hazard Class (CFR): NA
Additional Hazard Class (CFR): NA
Packaging Group (CFR): NA
UN ID Number (CFR): NA
Shipping Name (IATA): Non-hazardous
Hazard Class (IATA): NA
Additional Hazard Class (IATA): NA
Packaging Group (IATA): NA
UN ID Number (IATA): NA

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SECTION 15: Regulatory Information
TSCA: Listed in the TSCA inventory
SARA (Title 313): Title compound not listed
Second Ingredient: none

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  正十二烷基磷酸 在 吡啶 、 五氯化磷 作用下， 生成 dodecylphosphonate de dimethyle
  参考文献：
  名称：

  The Thermal Reaction between Alkylating Agents and Phosphonate or Phosphate Esters

  摘要：

  DOI：

  10.1021/jo01050a077
• 作为产物：
  描述：

  溴代十二烷 在 potassium hydroxide semihydrate 、 磷化氢 、 十六烷基三甲基溴化铵 、 硝酸 作用下， 以 水 、 甲苯 为溶剂， 反应 8.0h， 以61%的产率得到正十二烷基磷酸
  参考文献：
  名称：

  胶束/相转移催化红磷和超碱对烷基溴的膦酰化反应合成长链正烷基膦酸

  摘要：

  基于超碱体系KOH / H 2 O /甲苯/相转移催化剂中烷基溴与红磷的直接膦酰化作用，开发了一种单锅法合成烷基膦酸的方法。十六烷基三甲基溴化铵已成功用作胶束相转移催化剂，超碱性氢氧根阴离子的载体。

  DOI：

  10.1002/ejoc.202100067
• 作为试剂：
  描述：

  2,6-二氟吡啶 在 N-氯代丁二酰亚胺 、 正丁基锂 、 五甲基二乙烯三胺 、 正十二烷基磷酸 、 potassium carbonate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 68.0h， 生成 6-(azetidin-1-yl)-3-chloro-2-fluoropyridin-4-amine
  参考文献：
  名称：

  [EN] INHIBITORS OF THE BCL6 BTB DOMAIN PROTEIN-PROTEIN INTERACTION AND USES THEREOF
  [FR] INHIBITEURS DE L'INTERACTION PROTÉINE-PROTÉINE DU DOMAINE BCL6 BTB ET LEURS UTILISATIONS

  摘要：

  本申请涉及公式I（I）化合物或其药用可接受的盐、溶剂化合物和/或前药，包括含有这些化合物或药用可接受的盐、溶剂化合物和/或前药的组合物，以及在治疗可通过抑制与BCL6 BTB的相互作用可治疗的疾病、紊乱或状况中的各种用途，如癌症。

  公开号：

  WO2019153080A1

文献信息

• Chromonic nanoparticles containing bioactive compounds
  申请人：Mohanty Sanat

  公开号：US20070086965A1

  公开（公告）日：2007-04-19

  A chromonic nanoparticle mixture prepared by combining (i) a continuous water-soluble polymer phase and (ii) a discontinuous chromonic phase comprising a chromonic material; and non-covalently crosslinking the resulting chromonic nanoparticles with a polyvalent cation salt.

  通过将（i）连续的水溶性聚合物相和（ii）包含色相材料的不连续色相相结合制备的色相纳米颗粒混合物；并且用多价阳离子盐非共价交联所得的色相纳米颗粒。
• Cannabinoid CB1 Receptor Chemical Affinity Probes: Methods Suitable for Preparation of Isopropyl [11,12-³H]Dodecylfluorophosphonate and [11,12-³H]Dodecanesulfonyl Fluoride
  作者：Yoffi Segall、Gary B. Quistad、John E. Casida

  DOI：10.1081/scc-120021043

  日期：2003.7

  described along with conditions for their reduction with hydrogen (or potentially tritium) gas to the 1-dodecane derivatives as candidate high-potency (IC50 0.5–7 nM) chemical affinity probes for the mouse brain cannabinoid CB1 receptor and fatty acid amide hydrolase.

  摘要 描述了十二烷-11-烯基氟膦酸异丙酯和十二-11-烯磺酰氟的制备以及它们用氢气（或潜在的氚）气还原为 1-十二烷衍生物作为候选高效能 (IC50 0.5–7 nM) 的条件小鼠脑大麻素 CB1 受体和脂肪酸酰胺水解酶的化学亲和探针。
• Synthesis and antiproliferative activity of cytidine-5′-alkylphosphonophosphates and structurally related compounds
  作者：H. Brachwitz、U. Lachmann、Y. Thomas、J. Bergmann、W.E. Berdel、P. Langen

  DOI：10.1016/0009-3084(96)02599-6

  日期：1996.9

  The chemical synthesis of cytidine-5'-alkyl- and cytidine-5'-alkyl (acyl)deoxyglycerophosphonophosphates is reported. The compounds obtained represent a novel class of cytostatically active agents based on phospholipids, which inhibit the growth of various tumor cell lines in vitro. They are phosphono analogs of the cytidine-5'-diphosphate-diacylglycerol (CDP-DAG) possessing a structurally modified lipid

  报道了胞苷-5'-烷基-和胞苷5'-烷基（酰基）脱氧甘油磷酸膦的化学合成。获得的化合物代表一类基于磷脂的新型细胞抑制活性剂，其在体外抑制各种肿瘤细胞系的生长。它们是具有结构上经修饰的脂质部分和耐磷脂酶C的PC键的胞苷5'-二磷酸-二酰基甘油（CDP-DAG）的膦酰基类似物。胞苷-5'-烷基膦磷酸酯的抗增殖功效在很大程度上取决于烷基链的长度。发现胞嘧啶核苷5'-十六烷基磷酸磷酸酯是这项研究中测试的最有效的化合物。它的细胞抑制作用明显高于烷基（酰基）脱氧甘油衍生物和相应的二磷酸酯。通过快速原子轰击质谱法（FAB）确认了新化合物的结构。讨论了FAB碎片模式。
• Cross-linkable phosphonate-containing supramolecular complexes and their use for delivery of therapeutic and diagnostic agents
  申请人：——

  公开号：US20030224038A1

  公开（公告）日：2003-12-04

  Cross-linkable, phosphonate containing supramoleuclar aggregates are disclosed, which may be used to advantage, for example, as drug delivery vehicles for the treatment of bone-related disorders.

  公开了含有交联性、膦酸盐的超分子聚集体，可以用作药物传递载体，例如用于治疗与骨相关的疾病。
• [EN] LPA RECEPTOR AGONISTS AND ANTAGONISTS<br/>[FR] AGONISTES DES RÉCEPTEURS DE LPA ET ANTAGONISTES
  申请人：RXBIO INC

  公开号：WO2010051053A1

  公开（公告）日：2010-05-06

  Disclosed are compounds according to formula (I) as well as pharmaceutical compositions which include those compounds. Also disclosed are methods of using such compounds, which have activity as agonists or as antagonists of LPA receptors; such methods including treating cancer, producing radioprotection and/or radiomitigation, enhancing cell proliferation, treating a wound, treating apoptosis or preserving or restoring function in a cell, tissue, or organ, culturing cells, preserving organ or tissue function, and treating a dermato logical condition.

  揭示了按照式(I)的化合物，以及包括这些化合物的药物组合物。还揭示了使用这些化合物的方法，这些方法具有作为LPA受体激动剂或拮抗剂的活性；这些方法包括治疗癌症、产生放射保护和/或减轻放射损伤、增强细胞增殖、治疗伤口、治疗凋亡或在细胞、组织或器官中保护或恢复功能、培养细胞、保护器官或组织功能，以及治疗皮肤病理条件。