1-(n-Butyl)-3-nitroguanidin | 5458-83-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(n-Butyl)-3-nitroguanidin
• 英文别名: 3-Nitro-1-n-butyl-guanidin；N-butyl-N'-nitro-guanidine；N-Butyl-N'-nitro-guanidin；1-Butyl-2-nitroguanidine；1-butyl-2-nitroguanidine
• CAS: 5458-83-3
• 化学式: C₅H₁₂N₄O₂
• 分子量: 160.176
• InChiKey: KPQHRDFCWBWTBA-UHFFFAOYSA-N

物化性质

• 熔点：
  83.5 °C
• 沸点：
  232.4±23.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  96.2
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  4.1
• 海关编码：
  2925290090

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 1-Butyl-3-nitroguanidine
CAS-No. : 5458-83-3
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Flammable solids (Category 2)
Acute toxicity, Oral (Category 3)
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Highly flammable. Toxic if swallowed. Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Danger
Hazard statement(s)
H228 Flammable solid.
H301 Toxic if swallowed.
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P210 Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P301 + P310 IF SWALLOWED: Immediately call a POISON CENTER or doctor/
physician.
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)
R11 Highly flammable.
R25 Toxic if swallowed.
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S16 Keep away from sources of ignition - No smoking.
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.
S45 In case of accident or if you feel unwell, seek medical advice immediately
(show the label where possible).
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C5H12N4O2
Molecular Weight : 160,17 g/mol
Component Concentration
1-Butyl-3-nitroguanidine
CAS-No. 5458-83-3 -

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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. Take victim immediately to hospital. 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
Do NOT induce vomiting. 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

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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
Use water spray to cool unopened containers.

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Wear respiratory protection. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate
ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Contain spillage, and then collect with an electrically protected vacuum cleaner or
by wet-brushing and place in container for disposal according to local regulations (see section 13). Keep
in suitable, closed containers for disposal. Contain spillage, pick up with an electrically protected vacuum
cleaner or by wet-brushing and transfer to a container for disposal according to local regulations (see
section 13).
Reference to other sections
For disposal see section 13.

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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.Keep away from sources of ignition
- No smoking.Take measures to prevent the build up of electrostatic charge.
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

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling
the product.
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, Flame retardant antistatic protective clothing, The type
of protective equipment must be selected according to the concentration and amount of the
dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face particle
respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering
controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use
respirators and components tested and approved under appropriate government standards such
as NIOSH (US) or CEN (EU).

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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: 83 - 86 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) The substance or mixture is a flammable solid with the category 2.
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- no data available
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

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
Heat, flames and sparks. Extremes of temperature and direct sunlight.
Incompatible materials
Strong oxidizing agents, Strong bases
Hazardous decomposition products
Other decomposition products - no data available

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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
no data available
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 Toxic 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

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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

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting
as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal
company. Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: 2930 IMDG: 2930 IATA: 2930
UN proper shipping name
ADR/RID: TOXIC SOLID, FLAMMABLE, ORGANIC, N.O.S. (1-Butyl-3-nitroguanidine)
IMDG: TOXIC SOLID, FLAMMABLE, ORGANIC, N.O.S. (1-Butyl-3-nitroguanidine)
IATA: Toxic solid, flammable, organic, n.o.s. (1-Butyl-3-nitroguanidine)
Transport hazard class(es)
ADR/RID: 6.1 (4.1) IMDG: 6.1 (4.1) IATA: 6.1 (4.1)
Packaging group
ADR/RID: II IMDG: II IATA: II
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1-(n-Butyl)-3-nitroguanidin 在 ammonium hydroxide 、 水 、 锌 作用下， 生成 N-ethyl-N'-butyl-guanidine
  参考文献：
  名称：

  Davis; Rosenquist, Journal of the American Chemical Society, 1937, vol. 59, p. 2114

  摘要：

  DOI：
• 作为产物：
  描述：

  butylguanidine nitrate 在 硫酸 作用下， 生成 1-(n-Butyl)-3-nitroguanidin
  参考文献：
  名称：

  Davis; Elderfield, Journal of the American Chemical Society, 1933, vol. 55, p. 737

  摘要：

  DOI：

文献信息

• Sur la substitution des alcoyl- et arylguanidines par des restes acides
  作者：Eric Junod

  DOI：10.1002/hlca.19520350343

  日期：1952.5.2

  1. La substitution des guanidines alcoylées ou arylées par le chloroformiate de méthyle (effectuée dans l'acétone en présence de NaOH aq. conc.) est totale chez celles qui portent jusqu'à 3 atomes d'hydrogène, à l'exception de la diphénylguanidine asym. – Les nitro-, mono- et dialcoyl-nitro- et monoaryl-cyanoguanidines ont été dicarbométhoxylées. La dicyandiamide elle-même n'est pas acylée dans les

  1.取代甲氧基氯甲酸甲酯的胍基化合物（影响浓NaOH水溶液的浓度）估计总的乙酰胆碱含量约等于3原子的双氢化萘，其余的是diphénylguanidineasym。-二羰基乙氧基上的硝基，单-和二烯丙基-硝基-等单芳基-氰基胍。La dicyandiamideelle-mêmen'est pasacyléedans lesmêmes条件。
• Facile preparation of nitroguanidines containing a sulfoximine motif
  作者：Qun Shao、Hong-sen Li、Yu-long Xiao、Ya Li、Lin-jing Zhao、Xin-feng Ren、Yuan Liu、Jia-qing Liu

  DOI：10.1016/j.tetlet.2019.151450

  日期：2020.1

  synthesis of nitroguanidines containing a sulfoximine motif has been developed. A two-step process starts with the oxidation coupling of sulfides and N-alkyl nitroguanidines to form sulfanylidenes, followed by oxidation with m-chloroperbenzoic (m-CPBA) to give the target sulfoximine-nitroguanidines. The reaction had a broad substrate scope with respect to both sulfides and N-alkyl nitroguanidines under mild

  已经开发了有效合成具有硫代亚胺基序的硝基胍的方法。一个两步骤的过程开始于硫化物和N-烷基胍到形式sulfanylidenes的氧化偶联，接着用氧化米氯过（米-CPBA），得到目标亚磺酰亚胺，胍。在温和的反应条件下，对于硫化物和N-烷基硝基胍而言，反应具有较宽的底物范围。
• Reaction of Aromatic Heterocyclic Nitro Compounds with Potassium Cyanide. III. Some Nitroquinoline 1-Oxides
  作者：TOSHIHIKO OKAMOTO、HIROSHI TAKAHASHI

  DOI：10.1248/cpb.19.1809

  日期：——

  The reaction of 3-nitroquinoline 1-oxide with potassium cyanide in methanol was carried out producing 3-methoxycinchoninonitrile 1-oxide (I) and 3-methoxy-1H-pyrazolo [4, 3-b] quinoline-9-carboxamide (II). 5-Nitroquinoline 1-oxide gave 5-methoxyquinoline-6-carbonitrile 1-oxide (XIII) and 7-aminoisoxazolo [3, 4-f] quinoline 1-oxide (XIV), whereas 6-nitroquinoline 1-oxide gave methyl 5-cyano-6-methoxyquinaldimidate 1-oxide (VI), 5-cyano-6-methoxyquinaldamide 1-oxide (VII), and 1-hydroxy-6-nitrocarbostyril (VIII) by the similar type reactions. 4-Nitroquinoline 1-oxide produced 4-methoxyquinoline 1-oxide.

  3-硝基喹啉-1-氧化物与氰化钾在甲醇中反应，生成了3-甲氧基奎尼啶腈-1-氧化物（I）和3-甲氧基-1H-吡唑[4, 3-b]喹啉-9-羧酰胺（II）。5-硝基喹啉-1-氧化物生成了5-甲氧基喹啉-6-腈-1-氧化物（XIII）和7-氨基异噁唑[3, 4-f]喹啉-1-氧化物（XIV），而6-硝基喹啉-1-氧化物通过类似反应生成甲基5-氰基-6-甲氧基喹啉-1-氧化物（VI）、5-氰基-6-甲氧基喹啉酰胺-1-氧化物（VII）和1-羟基-6-硝基氨基苯乙烯（VIII）。4-硝基喹啉-1-氧化物产生了4-甲氧基喹啉-1-氧化物。
• Design, Synthesis, and Antifungal Activity of Sulfoximine Derivatives Containing Nitroguanidine Moieties
  作者：Yulong Xiao、Hongsen Li、Qun Shao、Yuan Liu、Yonghai Xie、Linjing Zhao、Ya Li

  DOI：10.1002/cbdv.202100839

  日期：2022.3

  discover novel pesticide candidates, a series of sulfoximine derivatives were designed and synthesized via the oxidation coupling reaction of sulfides and N-alkyl nitroguanidines. The compounds were evaluated for their antifungal activity against six phytopathogenic fungi. Most of them exhibited a broad spectrum of fungicidal activity in vitro. Compound 8IV-b displayed good fungicidal activity against

  为了发现新的候选农药，通过硫化物和N-烷基硝基胍的氧化偶联反应设计和合成了一系列亚砜亚胺衍生物。评估了这些化合物对六种植物病原真菌的抗真菌活性。它们中的大多数在体外表现出广谱的杀菌活性。化合物8IV-b对核盘菌、立枯丝核菌、灰霉病菌、禾谷镰刀菌和辣椒疫霉表现出良好的杀菌活性，EC 50值分别为 12.82、12.50、17.25、31.08 和 30.11 mg/L。此外，化合物8III-c和8IV-e对辣椒红的EC 50值分别为22.23和20.67 mg/L ，明显优于市售腐霉利(118.15 mg/L) 。引人注目的是，8IV-d对B. cinerea表现出令人满意的杀菌活性，其 EC 50值（7.42对10.83 mg/L）与对照腐霉利相当，体内生物测定进一步证实8IV-d具有有效的保护作用对B. cinerea的影响200 毫克/升 (72.2 %)。目前的这些发现将促进新型强效杀菌剂的设计和开发。
• 一种硝基胍类化合物及其制备与应用
  申请人：上海工程技术大学

  公开号：CN110903227B

  公开（公告）日：2021-09-10

  本发明涉及一种硝基胍类化合物及其制备与应用，该硝基胍类化合物为具有通式(I)所示结构的化合物，或其药学上可接受的盐、对映异构体、非对映异构体、互变异构体、溶剂化物、多晶型物或前药：其中，R1为C1～C8饱和或不饱和脂肪烃基、苄基、取代苄基或取代吡啶甲基中的一种；R2为C1～C8饱和或不饱和脂肪烃基、苯基、取代苯基或取代吡啶基中的一种。与现有技术相比，本发明的硝基胍类化合物对镰刀菌、赤霉菌、茄匐柄霉菌、疫霉菌、瓜果腐霉、灰霉菌、核盘菌、立枯丝核菌等农业上的真菌病害具有较好的防效，可用作潜在的植物杀菌剂使用。