3-硝基二戊醇 | 5447-99-4

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 3-硝基二戊醇
• 中文别名: 3-硝基-2-戊醇
• 英文名称: 3-nitro-pentan-2-ol
• 英文别名: 3-Nitro-2-pentanol；3-nitropentan-2-ol；Methyl-(1-nitro-propyl)-carbinol；2-Hydroxy-3-Nitropentane；2-Hydroxy-3-nitro-pentan；3-Nitro-pentanol-(2)
• CAS: 5447-99-4
• 化学式: C₅H₁₁NO₃
• mdl: MFCD00007399
• 分子量: 133.147
• InChiKey: CHOTTWGZEKCPHA-UHFFFAOYSA-N

物化性质

• 沸点：
  60 °C0.5 mm Hg(lit.)
• 密度：
  1.075 g/mL at 25 °C(lit.)
• 闪点：
  195 °F
• 稳定性/保质期：
  在常温常压下，它保持稳定。

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 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：
  66
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2905590090
• 储存条件：
  密封保存，应储存在阴凉干燥的地方，并远离火源。

SDS

Name:	3-Nitro-2-pentanol 99% Material Safety Data Sheet
Synonym:	None
CAS:	5447-99-4

Section 1 - Chemical Product MSDS Name:3-Nitro-2-pentanol 99% Material Safety Data Sheet
Synonym:None

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
5447-99-4	3-Nitro-2-pentanol	99.0	226-669-0

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.Combustible liquid.
Potential Health Effects
Eye:
Non-irritating to the eyes.
Skin:
Non-irritating to the skin.
Ingestion:
Low hazard for usual industrial handling. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation.
Chronic:
No information found.

---

Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Get medical aid if irritation develops or persists. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. 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 if cough or other symptoms appear.
Notes to Physician:
Antidote: None reported.

---

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. Will burn if involved in a fire. Use water spray to keep fire-exposed containers cool. Combustible liquid. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Containers may explode when heated.
Extinguishing Media:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam. Use water spray to cool fire-exposed containers.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Remove all sources of ignition.
Provide ventilation.

---

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use only in a well-ventilated area.
Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed.
Keep away from heat, sparks and flame. Avoid ingestion and inhalation. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames.
Storage:
Keep away from heat, sparks, and flame. Keep away from sources of ignition. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

---

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# 5447-99-4: 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: colorless to light yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 60 deg C @ .50mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: 90 deg C ( 194.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.0750g/cm3
Molecular Formula: C5H11NO3
Molecular Weight: 133.15

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, ignition sources, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported.

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 5447-99-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-Nitro-2-pentanol - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION
Other No information available.

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 5447-99-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 5447-99-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 5447-99-4 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-硝基二戊醇 在 苯酐 作用下， 生成 3-硝基-3-戊烯
  参考文献：
  名称：

  Channanow et al., Metodiceskij sbornik, 1959, # 26, p. 59

  摘要：

  DOI：
• 作为产物：
  描述：

  trimethyl(3-nitropentan-2-yloxy)silane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 3-硝基二戊醇
  参考文献：
  名称：

  Lee, Kilsung; Oh, Dong Young, Synthetic Communications, 1989, vol. 19, # 17, p. 3055 - 3060

  摘要：

  DOI：

文献信息

• Synthesis of 2,2′-bipyrrole-5-carboxaldehydes and their application in the synthesis of B-ring functionalized prodiginines and tambjamines
  作者：Papireddy Kancharla、Kevin A. Reynolds

  DOI：10.1016/j.tet.2013.07.067

  日期：2013.9

  Facile, versatile, and cost-effective synthetic routes for the preparation of a range of new 3-alkyl-, 4-alkyl-, 3,4-dialkyl-, and 3-halo-4-alkyl-2,2′-bipyrrole-5-carboxaldehydes have been developed. These 2,2′-bipyrrole-5-carboxaldehydes offer interesting potential as building blocks for making bioactive natural and unnatural products, as demonstrated by the synthesis of B-ring functionalized prodiginines

  已经开发出用于制备一系列新型 3-烷基-、4-烷基-、3,4-二烷基-和 3-卤代-4-烷基-2,2′-联吡咯-5-甲醛的简单、多功能和具有成本效益的合成路线。这些 2,2′-联吡咯-5-甲醛作为制造生物活性天然和非天然产物的构建块具有有趣的潜力，正如 B 环官能化 prodiginines （PG） 和 tambjamines 的合成所证明的那样。
• Regioselective synthesis of 5-unsubstituted benzyl pyrrole-2-carboxylates from benzyl isocyanoacetate
  作者：Noboru Ono、Hiromi Katayama、Siho Nisyiyama、Takuji Ogawa

  DOI：10.1002/jhet.5570310402

  日期：1994.7

  A general synthesis of 5-unsubstituted benzyl pyrrole-2-carboxylates was developed based on the reaction of β-nitroacetates with benzyl isocyanoacetate. The advantage of this route over other pyrrole syntheses was the regiochemical control of the substitution pattern on the pyrrole ring.

  基于β-硝基乙酸酯与异氰基乙酸苄酯的反应，开发了5-未取代的苄基吡咯-2-羧酸酯的一般合成方法。该路线相对于其他吡咯合成的优点是对吡咯环上取代模式的区域化学控制。
• Kinetics and mechanisms of the gas-phase elimination of 2-substituted primary, secondary and tertiary hydroxy groups in nitroalkanes
  作者：Rosa María Domínguez、Armando Herize、Alexandra Rotinov、Alvaro Alvarez-Aular、Gonzalo Visbal、Gabriel Chuchani

  DOI：10.1002/poc.743

  日期：2004.5

  The kinetics of the gas-phase elimination of several 2-substituted primary, secondary and tertiary hydroxy groups in nitroalkanes were determined in a static reaction system over the temperature range 220–400°C and pressure range of 29–235 Torr. The reactions, in seasoned vessels, are homogeneous and unimolecular and obey a first-order rate law. The presence of secondary and tertiary hydroxy substituent

  在静态反应系统中，在温度范围为220–400°C和压力范围为29–235 Torr的条件下，测定了硝基链烷烃中几个2-取代的伯，仲和叔羟基的气相消除动力学。在经验丰富的血管中，反应是均一的和非分子的，并且服从一阶速率定律。在硝基烷烃中，在硝基的2-位上存在仲和叔羟基取代基会导致逆醛醇型分解。可以根据六元环状过渡态合理化该机理，以分别给出相应的醛或酮和硝基烷。然而，硝基烷中的某些伯2-羟基经过脱水过程，其异构化为相应的硝酸烷基酯的能力非常有限。据信脱水机理是通过六元而不是已经报道的四元环状过渡态进行的，从而得到硝基烯烃和水。对于2-甲基-2-硝基-1-戊醇中的伯羟基取代基，消除的产物为HNO2气体和3-羟基-2-甲基-1-丙烯。根据四元循环过渡态机制的类型，此反应是合理的。提出并讨论了羟基硝基烷烃底物的动力学和热力学参数。版权所有©2004 John Wiley＆Sons，Ltd.
• Addition of aldehydes to organic compounds having a carbon-hydrogen bond
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04581178A1

  公开（公告）日：1986-04-08

  Low valent transition metal complexes containing small cone angle phosphine or arsine ligands efficiently catalyze addition of aldehydes to compounds or groups having a C--H bond activated by a nitro or nitrile group, to provide nitroalcohols or cyanohydrins, respectively.

  含有小锥角膦或胂配体的低价过渡金属配合物有效催化醛类与被硝基或腈基激活的C-H键化合物或基团的加成反应，分别生成硝基醇或氰水合物。
• A new methodology for the preparation of 2-cyanopyrroles and synthesis of porphobilinogen
  作者：Maciej Adamczyk、Rajarathnam E. Reddy

  DOI：10.1016/0040-4020(96)00941-6

  日期：1996.11

  Condensation of α-acetoxynitro compounds 4a-f with isocyanoacetonitrile (5) using DBU in THF afforded 2-cyano-3,4-substituted pyrroles 6a-f, in good yield. Porphobilinogen (PBG, 12), the key building block for the preparation of tetrapyrrolic natural products, was synthesized from 2-cyano-3,4-substituted pyrrole 6f, in four steps.

  使用DBU在THF中将α-乙酰氧基硝基化合物4a-f与异氰基乙腈（5）缩合，以良好的产率得到2-氰基-3,4-取代的吡咯6a-f。卟啉胆碱原（PBG，12）是制备四吡咯天然产物的关键组成部分，它是由2-氰基3,4-取代的吡咯6f分四个步骤合成的。

表征谱图