2-溴-2-氰基-N,N-二甲基乙酰胺 | 15430-62-3

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-溴-2-氰基-N,N-二甲基乙酰胺
• 中文别名: 2-(N,N-二甲基氨基甲酰基)-2-溴乙腈；N,N-二甲基-2-溴-2-氰基乙酰胺
• 英文名称: N,N-dimethyl-2-bromo-3-nitrilopropionamide
• 英文别名: 2-Bromo-2-cyano-N,N-dimethylacetamide；2-Bromo-2-cyano-N,N-dimethylacetamid；2-Brom-2-cyan-N,N-dimethyl-acetamid
• CAS: 15430-62-3
• 化学式: C₅H₇BrN₂O
• 分子量: 191.027
• InChiKey: HLAJXHYCSPHGGI-UHFFFAOYSA-N

物化性质

• 熔点：
  57°C
• 沸点：
  135 °C / 3mmHg
• 密度：
  1.560±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2926909090

SDS

2-Bromo-2-cyano-N,N-dimethylacetamide
SAFETY DATA SHEET

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Section 1. IDENTIFICATION OF THE SUBSTANCE OR MIXTURE AND OF THE SUPPLIER
Product name: 2-Bromo-2-cyano-N,N-dimethylacetamide

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Section 2. HAZARDS IDENTIFICATION
Classification of the GHS
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Category 4
Acute toxicity (Oral)
Acute toxicity (Dermal) Category 4
Category 4
Acute toxicity (Inhalation)
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements
Pictograms or hazard symbols
Signal word Warning
Hazard statement Harmful by inhalation, in contact with skin and if swallowed
Causes skin irritation
Causes serious eye irritation
Precautionary statements
[Prevention] Avoid breathing.
Use only outdoors or in a well-ventilated area.
Do not eat, drink or smoke when using this product.
Wash hands thoroughly after handling.
Wear protective gloves and eye/face protection.
IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for
[Response]
breathing. Call a POISON CENTER or doctor/physician if you feel unwell.
IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell.
Rinse mouth.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Wash contaminated clothing before reuse.
Call a POISON CENTER or doctor/physician if you feel unwell.
[Disposal] Dispose of contents/container through a waste management company authorized by
the local government
2-Bromo-2-cyano-N,N-dimethylacetamide

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Component(s): 2-Bromo-2-cyano-N,N-dimethylacetamide
Percent: >90.0%(GC)
CAS Number: 15430-62-3
Synonyms: N,N-Dimethyl-2-bromo-2-cyanoacetamide , 2-(N,N-Dimethylcarbamoyl)-2-
bromoacetonitrile
Chemical Formula: C5H7BrN2O

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Call a POISON CENTER or doctor/physician if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards: Take care as it may decompose upon combustion or in high temperatures to
generate poisonous fume.
Specific methods: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Use personal protective equipment. Keep people away from and upwind of spill/leak.
Personal precautions,
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Storage
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store under inert gas.
Store locked up.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Law is followed.
2-Bromo-2-cyano-N,N-dimethylacetamide

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator, self-contained breathing apparatus(SCBA), supplied air respirator,
etc. Use respirators approved under appropriate government standards and follow
local and national regulations.
Hand protection: Impervious gloves.
Safety goggles. A face-shield, if the situation requires.
Eye protection:
Skin and body protection: Impervious protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
crystal - powder
Form:
Color: White - Pale yellow
No data available
Odor:
pH: No data available
Melting point/freezing point:57 °C
Boiling Point/Range: 135 °C/0.4kPa
Flash Point: No data available
Explosive limits
No data available
Lower:
Upper: No data available
No data available
Density:
Solubility: Soluble in : Methanol

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Section 10. STABILITY AND REACTIVITY
Stability: Stable under proper conditions.
Reactivity: No special reactivity has been reported.
Conditions to avoid: Air-sensitive
Incompartible materials: oxidizing agents
Hazardous Decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx), Hydrogen bromide,
Hydrogen cyanide
Products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
No data available
NTP =
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobillity in soil
log Pow: No data available
Soil adsorption (Koc): No data available
2-Bromo-2-cyano-N,N-dimethylacetamide

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Section 12. ECOLOGICAL INFORMATION
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
Not Listed
UN-No:

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26,
2002): Safe use and production, the storage of a dangerous chemical, transport, loading and unloading were
prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-溴-2-氰基-N,N-二甲基乙酰胺 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 48.0h， 生成 2-amino-1,5,6-tricyano-4,4-bis[(cyclohexylideneamino)oxy]-N,N-dimethyl-3-azabicyclo[3.1.0]hex-2-ene-6-carboxamide
  参考文献：
  名称：

  Siaka; Lukin; Nasakin, Russian Journal of Organic Chemistry, 1999, vol. 35, # 2, p. 269 - 274

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N-二甲基氰乙酰胺 在 溴 作用下， 生成 2-溴-2-氰基-N,N-二甲基乙酰胺
  参考文献：
  名称：

  Monobromination of Cyanoacetamides and Amidinoacetamide with Molecular Bromine

  摘要：

  DOI：

  10.1248/cpb.22.965

文献信息

• N-acylsulfonamide apoptosis promoters
  申请人：——

  公开号：US20020055631A1

  公开（公告）日：2002-05-09

  N-Benzoyl arylsulfonamides having the formula 1 are BCL-Xl inhibitors and are useful for promoting apoptosis. Also disclosed are BCL-Xl inhibiting compositions and methods of promoting apoptosis in a mammal.

  N-苯甲酰芳基磺胺酰胺具有以下化学式，是BCL-Xl抑制剂，有助于促进细胞凋亡。还公开了BCL-Xl抑制组合物和在哺乳动物中促进细胞凋亡的方法。
• N-Acylsulfonamide apoptosis promoters
  申请人：——

  公开号：US20020086887A1

  公开（公告）日：2002-07-04

  N-Benzoyl arylsulfonamides having the formula 1 Are BCL-X1 inhibitors and are useful for promoting apoptosis. Also disclosed are BCL-X1 inhibiting compositions and methods of promoting apoptosis in a mammal.

  N-苯甲酰芳基磺胺酰胺具有以下化学式，是BCL-X1抑制剂，有助于促进细胞凋亡。还公开了BCL-X1抑制组合物和在哺乳动物中促进细胞凋亡的方法。
• A Convenient Synthesis of Dialkyl (<i>E</i>)-2,3-Dicyanobutendioates
  作者：Yoichi Yamada、Heinosuke Yasuda

  DOI：10.1055/s-1990-27009

  日期：——

  Dialkyl (E)-2,3-dicyanobutendioates 4, potentially useful intermediates for the synthesis of a wide variety of heterocyclic compounds, are conveniently prepared by the reaction of alkyl bromocyanoacetates 2 with potassium thiocyanate in acetonitrile followed by treatment with water. The starting alkyl bromocyanoacetates are prepared by the photochemical reaction of the appropriate alkyl cyanoacetate with bromine in carbon tetrachloride.

  4，二烷基（E）-2,3-二氰基丁二烯二酯是一类可能有用且能合成多种杂环化合物中间体的化合物，可通过二烷基溴氰基乙酸酯2与硫氰酸钾在乙腈中的反应，然后用水处理而方便地制备。起始原料二烷基溴氰基乙酸酯则是通过适当二烷基氰基乙酸酯与四氯化碳中的溴进行光化学反应制备得到的。
• Enantioselective α-Alkylation of Aldehydes by Photoredox Organocatalysis: Rapid Access to Pharmacophore Fragments from β-Cyanoaldehydes
  作者：Eric R. Welin、Alexander A. Warkentin、Jay C. Conrad、David W. C. MacMillan

  DOI：10.1002/anie.201503789

  日期：2015.8.10

  The combination of photoredox catalysis and enamine catalysis has enabled the development of an enantioselective α‐cyanoalkylation of aldehydes. This synergistic catalysis protocol allows for the coupling of two highly versatile yet orthogonal functionalities, allowing rapid diversification of the oxonitrile products to a wide array of medicinally relevant derivatives and heterocycles. This methodology

  光氧化还原催化和烯胺催化的结合使醛的对映选择性α-氰基烷基化的发展成为可能。这种协同催化方案可实现两个高度通用但正交的功能的耦合，从而使乙腈产物迅速多样化，成为多种医学上相关的衍生物和杂环。该方法也已应用于木脂素天然产物（-）-bursehernin的全合成。
• N-ACYLSULFONAMIDE APOPTOSIS PROMOTERS
  申请人：Augeri David J.

  公开号：US20090137585A1

  公开（公告）日：2009-05-28

  N-Benzoyl arylsulfonamides having the formula are BCL-Xl inhibitors and are useful for promoting apoptosis. Also disclosed are BCL-Xl inhibiting compositions and methods of promoting apoptosis in a mammal.

  具有以下式子的N-苯甲酰基芳基磺酰胺是BCL-Xl抑制剂，有助于促进细胞凋亡。本文还披露了BCL-Xl抑制剂组合物和在哺乳动物中促进细胞凋亡的方法。

表征谱图