2-氰乙基N,N-二异丙基氯亚磷酰胺 | 89992-70-1

• 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 - 有机氮化合物
• 中文名称: 2-氰乙基N,N-二异丙基氯亚磷酰胺
• 中文别名: 2-氰乙基N,N-二异丙基氯代亚磷酰胺；2-氰基乙基二异丙基氯代亚磷酰胺；氯代(二异丙基氨基)-β-氰基乙氧基膦；2-氰乙基 N,N-二异丙基氯代亚磷酰胺
• 英文名称: 2-Cyanoethyl N,N-diisopropylchlorophosphoramidite
• 英文别名: 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine；2-cyanoethyl diisopropylchlorophosphoramidite；CEPCl；3-((chloro(diisopropylamino)phosphaneyl)oxy)propanenitrile；2-cyanoethyl-N,N-diisopropylchlorophosphoroamidite；N,N-diisopropylamino-2-cyanoethoxychlorophosphine；3-((chloro(diisopropylamino)phosphino)oxy)propanenitrile；2-cyanoethyl-N,N-diisopropylphosphoramidochloridite；2-cyanoethyl N,N-diisopropylchlorophosphoramindite；2-cyanoethoxy-N,N-diisopropylaminochlorophosphine；chloro (2-cyanoethoxy)(diisopropylamino)phosphine；N,N-diisopropylamino cyanoethyl phosphoramidic chloride；3-(chloro(diisopropylamino)phosphine oxy)propionitrile；chloro(diisopropylamino)-β-cyanoethoxyphosphine；2-cyanoethyl-N,N-diisopropylaminochloro phosphite；3-[chloro-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
• CAS: 89992-70-1
• 化学式: C₉H₁₈ClN₂OP
• mdl: MFCD00011544
• 分子量: 236.681
• InChiKey: QWTBDIBOOIAZEF-UHFFFAOYSA-N

物化性质

• 沸点：
  103-105°C 0,08mm
• 密度：
  1.061 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F
• 溶解度：
  与氯仿和二氯甲烷混溶。
• 稳定性/保质期：

  按规定使用和贮存的不会分解，需避免接触碱性物质、酒精及高温环境。

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.888
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  8
• 危险品标志：
  C
• 安全说明：
  S26,S36/37/39,S45,S8
• 危险类别码：
  R29,R20/21/22,R34,R5
• WGK Germany：
  3
• 海关编码：
  29299090
• 危险品运输编号：
  UN 2845 4.2/PG 1
• 危险类别：
  8
• 包装等级：
  II
• 储存条件：
  -20°C条件下冷藏，需密闭保存并在干燥处存放。

SDS

Name:	2-Cyanoethyl n n-diisopropylchlorophosphoramidite Material Safety Data Sheet
Synonym:	Chloro(diisopropylamino)--cyanoethoxyphosphin
CAS:	89992-70-1

Section 1 - Chemical Product MSDS Name:2-Cyanoethyl n n-diisopropylchlorophosphoramidite Material Safety Data Sheet
Synonym:Chloro(diisopropylamino)--cyanoethoxyphosphin

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
89992-70-1	2-Cyanoethyl N,N-diisopropylchlorophos		unlisted

Hazard Symbols: C
Risk Phrases: 20/21/22 29 34 5

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Contact with water liberates toxic gas. Causes burns. Heating may cause an explosion.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Harmful if absorbed through the skin. Causes skin burns.
Ingestion:
Harmful if swallowed. Causes gastrointestinal tract burns.
Inhalation:
Harmful if inhaled. Causes chemical burns to the respiratory tract.
Chronic:
Not available.

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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 immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Do not induce vomiting. Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
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. Water Reactive. Material will react with water and may release a flammable and/or toxic gas. May explode when heated.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide. DO NOT USE WATER!

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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. Use a spark-proof tool.

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Section 7 - HANDLING and STORAGE
Handling:
Use spark-proof tools and explosion proof equipment. Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Store in a tightly closed container. Store in a dry area. Corrosives area. Deep freeze (below -20C). Store under nitrogen.

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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 general or local explosion-proof ventilation to keep airborne levels to acceptable levels.
Exposure Limits CAS# 89992-70-1: 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: Liquid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: 110 deg C ( 230.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.061
Molecular Formula: C9H18ClN2OP
Molecular Weight: 236.68

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Heating may cause an explosion. Moisture sensitive.
Conditions to Avoid:
Incompatible materials, exposure to moist air or water, heat.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong bases, alcohols.
Hazardous Decomposition Products:
Hydrogen chloride, nitrogen oxides, carbon monoxide, oxides of phosphorus, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 89992-70-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Cyanoethyl N,N-diisopropylchlorophosphoramidite - 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: CORROSIVE LIQUID, ACIDIC, ORGANIC, N.O.S.*
Hazard Class: 8
UN Number: 3265
Packing Group: II
IMO
Shipping Name: CORROSIVE LIQUID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3265
Packing Group: II
RID/ADR
Shipping Name: CORROSIVE LIQUID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3265
Packing group: II

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
R 29 Contact with water liberates toxic gas.
R 34 Causes burns.
R 5 Heating may cause an explosion.
Safety Phrases:
S 8 Keep container dry.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 89992-70-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 89992-70-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 89992-70-1 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

制备方法与用途

应用

N,N-二异丙基氯亚磷酰胺(2-氰基乙基)酯主要用作有机合成与医药化学中间体，可用于药物分子和有机催化反应中膦配体的合成。它具有很高的反应活性，与水或醇类化合物接触很容易进行水解或醇解反应。

合成方法

在氩气保护下，将1当量的N,N-二异丙基乙胺加入到干燥的1 -丁基-3 -甲基咪唑双[ (三氟甲基)磺酰亚胺] 的离子液体和PCl3（均为1当量）的混合溶液中，搅拌5分钟后，再加入1当量的3-羟基丙腈。将反应混合物继续搅拌30分钟，随后添加2当量的二异丙胺，并继续搅拌40分钟。使用干燥的乙醚萃取反应混合物后，分离有机层，向其中加入1-乙基-3-甲基咪唑三(五氟乙基)三氟磷酸盐以稳定产物。最后，在真空下浓缩除去有机溶剂，即可得到目标产物分子2-氰乙基 N,N-二异丙基氯代亚磷酰胺。

反应信息

• 作为反应物：
  描述：

  2-吗啉乙醇 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 3-[[Di(propan-2-yl)amino]-(2-morpholin-4-ylethoxy)phosphanyl]oxypropanenitrile
  参考文献：
  名称：

  [EN] PHOSPHATE ESTERS OF GYRASE AND TOPOISOMERASE INHIBITORS
  [FR] ESTERS PHOSPHORIQUES D'INHIBITEURS DE GYRASES ET DE TOPOISOMÉRASES

  摘要：

  本发明涉及抑制细菌旋转酶和/或拓扑异构酶IV的化合物的磷酸酯以及其药物组成物。这些磷酸酯对治疗细菌感染具有用途。

  公开号：

  WO2012177707A1
• 作为产物：
  描述：

  2-氰乙基二氯磷酸酯 生成 2-氰乙基N,N-二异丙基氯亚磷酰胺
  参考文献：
  名称：

  GASPARUTTO, D.;MOLKO, D.;TEOULE, R., NUCLEOSIDES AND NUCLEOTIDES, 9,(1990) N, C. 1087-1098

  摘要：

  DOI：
• 作为试剂：
  描述：

  1-(2,3-O-isopropylidene-β-D-ribofuranosyl)-5-<(N'-benzoylthiocarbamoyl)amino>pyrazole-4-carboxamide 在 吡啶 、 4-二甲氨基吡啶 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 、 silver nitrate 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 、 sodium hydroxide 、 碘甲烷 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 47.0h， 生成
  参考文献：
  名称：

  [EN] CYCLIC DI-NUCLEOTIDE COMPOUNDS AND METHODS OF USE
  [FR] COMPOSÉS DI-NUCLÉOTIDES CYCLIQUES ET LEURS PROCÉDÉS D'UTILISATION

  摘要：

  揭示了环二核苷酸cGAMP类似物，合成这些化合物的方法，包括这些化合物的药物组合物，以及在医学治疗中使用这些化合物和组合物的用途。

  公开号：

  WO2017161349A1

文献信息

• Synthesis and Properties of Aminoacylamido-AMP:  Chemical Optimization for the Construction of an <i>N</i>-Acyl Phosphoramidate Linkage
  作者：Tomohisa Moriguchi、Terukazu Yanagi、Masao Kunimori、Takeshi Wada、Mitsuo Sekine

  DOI：10.1021/jo0008338

  日期：2000.12.1

  This paper describes the design and synthesis of a new type of aminoacyl-adenylate analogue (aa-AMPN) having an N-acyl phosphoramidate linkage where the oxygen atom of the mixed anhydride bond of aminoacyl-adenylate (aa-AMP) is replaced by an amino group. This new type of aa-AMP analogue is expected to be useful as material for studies on the recognition mechanism of the aminoacylation of tRNA and

  本文介绍了具有N-酰基氨基磷酸酯键的新型氨基酰基-腺苷酸类似物（aa-AMPN）的设计和合成，其中氨基酰基-腺苷酸（aa-AMP）的混合酸酐键的氧原子被氨基。这种新型的aa-AMP类似物有望用作研究tRNA氨基酰化和其他生化反应识别机制的材料。羧酰胺的亚磷酰胺衍生物与核苷衍生物的缩合失败，因为活化的亚磷酰胺衍生物不仅与羟基反应，而且与另一种反应性物质反应。通过5'-O-亚磷酰胺基腺苷衍生物与羧酰胺衍生物的反应研究了另一种方法。选择TBTr和TSE基团分别用于保护氨基酸酰胺的氨基和磷酸基。详细研究表明，使用5-（3,5-二硝基苯基）-1H-四唑作为亚磷酰胺的活化催化剂可在10分钟内迅速缩合，从而得到完全保护的aa-AMPN衍生物。没有发生副反应。通过两步程序对这些产物进行脱保护，得到高产率的aa-AMPN衍生物。还证明由此获得的aa-AMPN在酸性和碱性条件下均是稳定的，例如0.1M HCl（pH
• Phthalimide-Oxy Derivatives for 3′- or 5′-Conjugation of Oligonucleotides by Oxime Ligation and Circularization of DNA by “Bis- or Tris-Click” Oxime Ligation
  作者：Albert Meyer、Jean-Jacques Vasseur、Pascal Dumy、François Morvan

  DOI：10.1002/ejoc.201701317

  日期：2017.12.15

  phosphoramidites exhibiting a phthalimide-oxy group were synthesized. First, after treatment with hydrazine, the resulting 5- and 3-oxyamine oligonucleotides were conjugated with aldehyde derivatives by oxime ligation. Second, oligonucleotides exhibiting an oxyamine at each end were circularized by means of different dialdehydes. Cyclic oligonucleotides of different lengths (9 to 31-mer) were rapidly obtained

  合成了一种固体载体和两种具有邻苯二甲酰亚胺-氧基团的亚磷酰胺。首先，在用肼处理后，所得的 5- 和 3- 氧胺寡核苷酸通过肟连接与醛衍生物缀合。其次，通过不同的二醛环化在每端显示氧胺的寡核苷酸。无需模板即可快速获得不同长度（9 至 31 聚体）的环状寡核苷酸。最后，从带有三个氧胺的寡核苷酸开始合成双环寡核苷酸，该寡核苷酸与三醛反应形成三个肟连接。
• Metal-mediated base pairing in DNA involving the artificial nucleobase imidazole-4-carboxylate
  作者：Nikolas Sandmann、Denise Defayay、Alexander Hepp、Jens Müller

  DOI：10.1016/j.jinorgbio.2018.10.013

  日期：2019.2

  Cu(II)-mediated base pairing. Moreover, it is the smallest nucleoside known to form stable Cu(II)-mediated base pairs. Structures of the X-Cu(II)-X and X-Ag(I)-X base pairs are proposed, too, based on molecular structures obtained using the model nucleobase 1-benzyl-1H-imidazole-4-carboxylate.

  据报道，在金属介导的碱基配对中，将咪唑-4-羧酸盐（X）用作人工核碱基。为此，合成了相应的脱氧核糖核苷，并在结构上表征为其钠盐（1,2-二脱氧-1-（4-羧基咪唑-1-基）-d-呋喃核糖钠。将脱氧核糖核苷掺入不同的DNA双链体（平行链和反平行链）中，并研究了它们的Cu（II）-和Ag（I）结合行为。结果表明，可以同时形成X-Cu（II）-X和X-Ag（I）-X碱基对，前者比后者更稳定。X-Cu（II）-X碱基对的形成伴随着反平行链双链体双链解链温度升高约20°C，平行链双链体的双链体解链温度升高约12°C。咪唑-4-羧酸盐代表Cu（II）介导的碱基配对的第一个基于咪唑的核苷。而且，它是已知形成稳定的Cu（II）介导的碱基对的最小核苷。基于使用模型核碱基1-苄基-1H-咪唑-4-羧酸盐获得的分子结构，也提出了X-Cu（II）-X和X-Ag（I）-X碱基对的结构。
• [EN] GalNAc CLUSTER PHOSPHORAMIDITE<br/>[FR] AGRÉGAT DE GALNAC-PHOSPHORAMIDITE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2017084987A1

  公开（公告）日：2017-05-26

  The invention comprises Gal NAc phosphoramidite derivatives of the formula (I), wherein R1 is a hydroxy protecting group, n is an integer from 0 to 10 and m is an integer from 0 to 20 and its corresponding enantiomers and/ or optical isomers thereof. The invention further comprises a process for the preparation of the Gal NAc phosphoramidite derivatives of the formula (I) and its use in the preparation of therapeutically valuable GalNAc-cluster oligonucleotide conjugates.

  该发明包括公式（I）中的Gal NAc磷酰胺衍生物，其中R1是一个羟基保护基团，n是从0到10的整数，m是从0到20的整数，以及其相应的对映体和/或光学异构体。该发明还包括一种制备公式（I）中的Gal NAc磷酰胺衍生物的方法，以及其在制备具有治疗价值的GalNAc-簇寡核苷酸共轭物中的用途。
• [EN] BIOACTIVE CONJUGATES FOR OLIGONUCLEOTIDE DELIVERY<br/>[FR] CONJUGUÉS BIOACTIFS POUR L'ADMINISTRATION D'OLIGONUCLÉOTIDES
  申请人：UNIV MASSACHUSETTS

  公开号：WO2017030973A1

  公开（公告）日：2017-02-23

  Provided herein are self-delivering oligonucleotides that are characterized by efficient RISC entry, minimum immune response and off-target effects, efficient cellular uptake without formulation, and efficient and specific tissue distribution.

  本文提供的自递送寡核苷酸具有高效的RISC进入、最小的免疫反应和非靶效应、无需配方的高效细胞摄取，以及高效和特异的组织分布。