(R)-(+)-1-Boc-2-吡咯烷甲腈 | 228244-20-0

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: (R)-(+)-1-Boc-2-吡咯烷甲腈
• 中文别名: (R)-1-Boc-2-氰基吡咯烷；1-N-Boc-2-吡咯烷甲腈；(R)-N-叔丁氧羰基-2-氰基吡咯烷；R-(+)-1-Boc-2-吡咯烷甲腈
• 英文名称: tert-butyl (R)-2-cyanopyrrolidine-1-carboxylate
• 英文别名: (R)-1-Boc-2-cyanopyrrolidine；tert-butyl (2R)-2-cyanopyrrolidine-1-carboxylate
• CAS: 228244-20-0
• 化学式: C₁₀H₁₆N₂O₂
• 分子量: 196.249
• InChiKey: MDMSZBHMBCNYNO-MRVPVSSYSA-N

物化性质

• 熔点：
  32-37℃
• 沸点：
  307.9±35.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)
• 闪点：
  >110℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品运输编号：
  NONH for all modes of transport
• 海关编码：
  2933990090
• WGK Germany：
  3
• 危险性防范说明：
  P261,P264,P280,P337+P313,P302+P352+P312,P304+P340+P312
• 危险性描述：
  H302+H312+H332,H315,H319
• 储存条件：
  室温

SDS

---

Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : (R)-(+)-1-Boc-2-pyrrolidinecarbonitrile
CAS-No. : 228244-20-0
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

---

Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Acute toxicity, Oral (Category 4)
Skin irritation (Category 2)
Eye irritation (Category 2)
Skin sensitization (Category 1)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Harmful if swallowed. Irritating to eyes, respiratory system and skin. May cause sensitization by skin
contact.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
H315 Causes skin irritation.
H317 May cause an allergic skin reaction.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust.
P280 Wear protective gloves.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R22 Harmful if swallowed.
R36/37/38 Irritating to eyes, respiratory system and skin.
R43 May cause sensitization by skin contact.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36/37/39 Wear suitable protective clothing, gloves and eye/face protection.
Other hazards - none

---

Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C10H16N2O2
Molecular Weight : 196,25 g/mol
Component Concentration
(R)-(+)-1-Boc-2-pyrrolidinecarbonitrile
CAS-No. 228244-20-0 -

---

Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

---

Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

---

Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

---

Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

---

Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Face shield and safety glasses Use equipment for eye protection tested and approved under
appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).

---

Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 32 - 36 °C - lit.
point
f) Initial boiling point and no data available
boiling range
g) Flash point > 110 °C - closed cup
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- log Pow: 1,5
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

---

Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

---

Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
May cause allergic skin reaction.
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion Harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

---

Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

---

Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material. Dissolve or mix the material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

---

Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

---

---

SECTION 15 - REGULATORY INFORMATION
N/A

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (R)-(+)-1-Boc-2-吡咯烷甲腈 在 sodium methylate 作用下， 以 甲苯 为溶剂， 反应 10.0h， 生成 (2'R)-5-<2'-N-(tert-butoxycarbonyl)pyrrolidinyl>-3,6-bis(trifluoromethyl)-1,2,4-triazine
  参考文献：
  名称：

  由（S）-和（R）-脯氨酸合成手性2-（2'-吡咯烷基）吡啶：神经元烟碱乙酰胆碱受体的潜在配体

  摘要：

  据报道，从（S）-和（R）-脯氨酸开始的新型光学活性尼古丁类似物的直接合成的新策略是利用迄今未知的手性5-（2）的逆电子需求的Diels-Alder反应作为关键步骤进行合成的。 '-吡咯烷基）-1,2,4-三嗪（S）-和（R）-16。这些用作制备不同的，高度对映体富集的2-（2'-吡咯烷基）吡啶，天然（-）-去甲烟碱和（-）-烟碱的修饰以及神经元烟碱型乙酰胆碱受体的潜在配体的合适前体。多步合成在温和的条件下进行，具有良好的总收率和原始立体异构中心的立体化学完整性。

  DOI：

  10.1016/s0957-4166(99)00028-2
• 作为产物：
  描述：

  D-脯氨酸 在 N-甲基吗啉 、 三聚氯氰 、 sodium hydroxide 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.25h， 生成 (R)-(+)-1-Boc-2-吡咯烷甲腈
  参考文献：
  名称：

  Evidence and exploitation of dicationic ammonium–nitrilium superelectrophiles: direct synthesis of unsaturated piperidinones

  摘要：

  利用超酸激活，氨基腈的反应性通过瞬时形成高度活性的铵盐-腈盐超电亲电子体得到增强。

  DOI：

  10.1039/d0cc02910f

文献信息

• The preparation of optically active α-amino 4H-[1,2,4]oxadiazol-5-ones from optically active α-amino acids
  作者：John E. Mangette、Matthew R. Johnson、Van-Duc Le、Rajesh A. Shenoy、Howard Roark、Michael Stier、Thomas Belliotti、Thomas Capiris、Peter R. Guzzo

  DOI：10.1016/j.tet.2009.09.045

  日期：2009.11

  Optically active α-amino 4H-[1,2,4]oxadiazol-5-ones (oxadiazolones) were prepared from optically active α-amino acids in five synthetic steps. The oxadiazolone moiety serves as a bioisosteric replacement for the carboxylic acid. Incorporation of an α-amino oxadiazolone into a representative dipeptide mimic is described.

  在五个合成步骤中，由旋光性α-氨基酸制备旋光性α-氨基4 H- [1,2,4]恶二唑-5-酮（恶二唑酮）。恶二唑酮部分用作羧酸的生物立体替代物。描述了将α-氨基恶二唑酮掺入代表性的二肽模拟物中。
• One-Pot Oxidative Conversion of Alcohols into Nitriles by Using a TEMPO/PhI(OAc)2/NH4OAc System
  作者：Jean-Michel Vatèle

  DOI：10.1055/s-0033-1341124

  日期：——

  A direct conversion of alcohols into nitriles with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO), iodosobenzene diacetate, and ammonium acetate as a nitrogen source is reported. This transformation, which proceeds through an oxidation–imination–aldimine oxidation sequence in situ, has been applied to a range of aliphatic, benzylic, heteroaromatic, allylic, and propargyl alcohols. Highly chemoselective

  据报道，使用 2,2,6,6-四甲基哌啶-1-氧基 (TEMPO)、二乙酸碘苯和乙酸铵作为氮源，将醇直接转化为腈。这种通过原位氧化-亚胺化-醛亚胺氧化序列进行的转化已应用于一系列脂肪醇、苄醇、杂芳醇、烯丙醇和炔丙醇。还实现了在仲醇存在下伯醇的高度化学选择性氨氧化。
• MGluR5 modulators I
  申请人：Wallberg Andreas

  公开号：US20070259862A1

  公开（公告）日：2007-11-08

  The present invention is directed to novel compounds, to a process for their preparation, their use in therapy and pharmaceutical compositions comprising the novel compounds.

  本发明涉及新化合物，以及用于它们的制备方法，它们在治疗中的应用以及包含这些新化合物的药物组合物。
• mGluR5 modulators III
  申请人：Isaac Methvin

  公开号：US20070259926A1

  公开（公告）日：2007-11-08

  The present invention is directed to novel compounds, to a process for their preparation, their use in therapy and pharmaceutical compositions comprising the novel compounds.

  本发明涉及新化合物，涉及它们的制备方法，它们在治疗中的应用以及包含这些新化合物的药物组合物。
• IMIDAMIDE SPHINGOSINE KINASE INHIBITORS
  申请人：Lynch Kevin R.

  公开号：US20120214858A1

  公开（公告）日：2012-08-23

  Imidamide (amidine) analogs that can inhibit the activity of sphingosine kinase 1 and sphingosine kinase 2 (SphK1 & SphK2) are provided. The compounds can prevent angiogenesis in tumors.

  提供可以抑制神经酰胺激酶1和神经酰胺激酶2（SphK1和SphK2）活性的Imidamide（胺基）类似物。这些化合物可以预防肿瘤中的血管生成。