异氰酸基甲酸甲酯 | 5843-42-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 异氰酸基甲酸甲酯
• 中文别名: 甲基碳化异氰碘酯
• 英文名称: methoxycarbonyl isocyanate
• 英文别名: n-(methoxycarbonyl)isocyanate；methyl carbonisocyanatidate；methyl isocyanatoformate；carbonisocyanatidic acid methyl ester；carbonylcarbamic acid methyl ester；Carbonyl-carbamidsaeure-methylester；methyl N-(oxomethylidene)carbamate
• CAS: 5843-42-5
• 化学式: C₃H₃NO₃
• mdl: MFCD00037079
• 分子量: 101.062
• InChiKey: YOVQDZPAVARTTR-UHFFFAOYSA-N

物化性质

• 沸点：
  97 °C (lit.)
• 密度：
  1.251 g/mL at 25 °C (lit.)
• 闪点：
  87 °F
• 稳定性/保质期：
  避免强氧化剂、强酸和醇。

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  55.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S16,S26,S36/37
• 危险类别码：
  R42,R20/21/22,R10,R36/37/38
• 海关编码：
  2929109000
• WGK Germany：
  3
• 危险品运输编号：
  UN 1993 3/PG 3
• 储存条件：
  -20°C，密闭保存。阴凉处避光保存。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Methyl isocyanatoformate
CAS-No. : 5843-42-5
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 liquids (Category 3)
Acute toxicity, Inhalation (Category 4)
Acute toxicity, Dermal (Category 4)
Acute toxicity, Oral (Category 4)
Skin irritation (Category 2)
Eye irritation (Category 2)
Respiratory sensitization (Category 1)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Flammable. Harmful by inhalation, in contact with skin and if swallowed. Irritating to eyes, respiratory
system and skin. May cause sensitization by inhalation.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Danger
Hazard statement(s)
H226 Flammable liquid and vapour.
H302 Harmful if swallowed.
H312 Harmful in contact with skin.
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H332 Harmful if inhaled.
H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing vapours.
P280 Wear protective gloves/ protective clothing.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
P342 + P311 If experiencing respiratory symptoms: Call a POISON CENTER or doctor/
physician.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R10 Flammable.
R20/21/22 Harmful by inhalation, in contact with skin and if swallowed.
R36/37/38 Irritating to eyes, respiratory system and skin.
R42 May cause sensitization by inhalation.
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 Wear suitable protective clothing and gloves.
Other hazards
Lachrymator.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C3H3NO3
Molecular Weight : 101,06 g/mol
Component Concentration
Methyl isocyanatoformate
CAS-No. 5843-42-5 -

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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. 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
burning sensation, Cough, wheezing, laryngitis, Shortness of breath, Headache, Nausea, Vomiting
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
For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large
fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or
spray; solid streams of water may be ineffective. Cool all affected containers with flooding quantities of
water.
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
Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation.
Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapours accumulating to
form explosive concentrations. Vapours can accumulate in low areas.
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
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).
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 inhalation of vapour or mist.
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. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Recommended storage temperature: -20 °C
Moisture sensitive.
Specific end use(s)
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
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, 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 respirator
with multi-purpose combination (US) or type ABEK (EN 14387) 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: liquid
Colour: colourless
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and 97 °C - lit.
boiling range
g) Flash point 31 °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 1,251 g/cm3 at 25 °C
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignition 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.
Incompatible materials
Strong oxidizing agentsStrong acids, Alcohols, Strong oxidizing agents
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
May cause allergic respiratory 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 Harmful if inhaled. Causes respiratory tract irritation.
Ingestion Harmful if swallowed.
Skin Harmful if absorbed through skin. Causes skin irritation.
Eyes
Causes serious eye irritation.
Signs and Symptoms of Exposure
burning sensation, Cough, wheezing, laryngitis, Shortness of breath, Headache, Nausea, Vomiting
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: 1993 IMDG: 1993 IATA: 1993
UN proper shipping name
ADR/RID: FLAMMABLE LIQUID, N.O.S. (Methyl isocyanatoformate)
IMDG: FLAMMABLE LIQUID, N.O.S. (Methyl isocyanatoformate)
IATA: Flammable liquid, n.o.s. (Methyl isocyanatoformate)
Transport hazard class(es)
ADR/RID: 3 IMDG: 3 IATA: 3
Packaging group
ADR/RID: III IMDG: III IATA: III
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
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

甲氧羰基异氰酸酯可以用于化合物的合成[1]。

反应信息

• 作为反应物：
  描述：

  异氰酸基甲酸甲酯 在 15N-氨 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 [15N](amide) methoxycarbonyl urea
  参考文献：
  名称：

  Revealing CSA Tensors and Hydrogen Bonding in Methoxycarbonyl Urea: A combined ¹³C, ¹⁵N and ¹³C¹⁴N₂ Dipolar Chemical Shift NMR and DFT Study

  摘要：

  甲氧基羰基脲（MCU）是一种潜在的长效氮肥，通过¹³C和¹⁵N偶极化化学位移核磁共振光谱和ab initio计算进行了研究。采用偶极化化学位移核磁共振、选择性同位素标记和ab initio气相计算的组合，揭示了所有¹⁵N核和三个¹³C核中两个的可能分子结构和化学屏蔽张量。计算中发现了四种可能的稳定构型，具有不同的能量。对于这些构型，计算了化学位移张量。虽然具有最低能量的构型的计算的¹³C（脲）化学位移张量方向与实验张量方向吻合良好，但计算和实验张量特征值之间存在显著差异。这些差异明确表明了实验样品中存在的分子间氢键的存在，这在气相计算中被忽略了。实验¹³C（脲）化学位移张量存在四种不同的可能方向，由于对称性而产生的。通过与¹³C化学位移张量的GIAO计算结果进行比较，采用最小能量构型（EEZ），解决了这种歧义。发现在分子中采用了δ₁₁大致指向N（imide）方向，δ₂₂大致指向C=O键方向，δ₃₃与分子框架垂直的方向。

  DOI：

  10.1524/zpch.217.12.1473.20470
• 作为产物：
  描述：

  二甲基氰基亚氨基二碳酸酯 在 phosphorus pentoxide 作用下， 生成 异氰酸基甲酸甲酯
  参考文献：
  名称：

  Diels; Gollmann, Chemische Berichte, 1911, vol. 44, p. 3164

  摘要：

  DOI：

文献信息

• Efficient Preparation of Cyclic α-Alkylidene β-Oxo Imides by Using a Flow Microreactor System
  作者：Masahisa Nakada、Katsuhiro Komuro、Aiichiro Nagaki、Hiroki Shimoda、Masahiro Uwamori、Jun-ichi Yoshida

  DOI：10.1055/s-0037-1610228

  日期：2018.9

  emphasized in the reaction of the organolithium compound with methoxycarbonyl isocyanate, which gave the desired imide in 78% yield by using the flow microreactor system whereas the yield of the corresponding batch reaction was only 2%. The established flow microreactor system was also effectively used for the reaction of the organolithium compound with phenyl isocyanate to afford the desired product in 52%

  描述了 3-iodo-1-methyl-5,6-dihydropyridin-2(1H)-one 通过卤素-锂交换和随后在流动微反应器系统中的反应成功转化为其衍生物。在流动微反应器系统中由 3-iodo-1-methyl-5,6-dihydropyridin-2(1H)-one 产生的有机锂化合物的甲基化以 68% 的产率提供了所需的甲基化产物，而相应批次的产率反应率为 23%。流动微反应器系统的这种优势在有机锂化合物与异氰酸甲氧基羰基酯的反应中得到进一步强调，使用流动微反应器系统以 78% 的收率得到所需的酰亚胺，而相应的间歇反应的收率仅为 2%。
• CHEMOKINE RECEPTOR ANTAGONISTS AND METHODS OF USE THEREOF
  申请人：Millennium Pharmaceuticals, Inc.

  公开号：US20160031908A1

  公开（公告）日：2016-02-04

  Disclosed are novel compounds and a method of treating a disease associated with aberrant leukocyte recruitment and/or activation. The method comprises administering to a subject in need an effective amount of a compound represented by: or physiologically acceptable salt thereof.

  揭示了新颖的化合物以及治疗与异常白细胞召集和/或激活相关的疾病的方法。该方法包括向需要的受试者施用代表的化合物的有效量： 或其生理上可接受的盐。
• HIV protease inhibiting compounds
  申请人：DeGoey A. David

  公开号：US20050148623A1

  公开（公告）日：2005-07-07

  A compound of the formula is disclosed as an HIV protease inhibitor. Methods and compositions for inhibiting an HIV infection are also disclosed.

  披露了一种公式的化合物作为HIV蛋白酶抑制剂。还披露了用于抑制HIV感染的方法和组合物。
• Multicomponent Synthesis of Dihydropyrimidines and Thiazines
  作者：Danielle J. Vugts、Manoe M. Koningstein、Rob F. Schmitz、Frans J. J. de Kanter、Marinus B. Groen、Romano V. A. Orru

  DOI：10.1002/chem.200600168

  日期：2006.9.18

  been observed. Furthermore, the multicomponent reaction seems to be restricted to the use of isocyanates with strongly electron-withdrawing substituents, but an interesting additional exchange reaction under microwave conditions leads to dihydropyrimidines with less electron-withdrawing substituents at N3. In addition, a diastereoselective formation of dihydropyrimidines has been observed when using a

  通过使用膦酸酯，腈，醛和异（硫）氰酸酯之间的四组分反应，可以有效地制备各种不同取代的二氢嘧啶和噻嗪。充分描述了该多组分反应的范围和局限性。已经研究了所有四个组件的变化。腈和醛的输入量可以广泛变化，但是膦酸酯输入量的变化仍然有限。已经观察到有趣的重排导致氨基磷酸酯。此外，多组分反应似乎仅限于使用具有强吸电子取代基的异氰酸酯，但是在微波条件下有趣的附加交换反应会导致二氢嘧啶在N3处具有吸电子取代基较少。此外，当使用手性醛作为输入时，已经观察到二氢嘧啶的非对映选择性形成。最后，通过将异氰酸酯组分改变为异硫氰酸酯，可以有效地形成噻嗪，而不是相应的硫代-二氢嘧啶。
• [EN] NOVEL 17ß LUPANE DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS DE 17SS-LUPANE
  申请人：VIROCHEM PHARMA INC

  公开号：WO2009100532A1

  公开（公告）日：2009-08-20

  The invention relates to 17ß lupane derivatives of formula (I): wherein R1 and X are as defined herein, and pharmaceutically acceptable salts and solvates thereof. These compounds exhibit significant anti-HIV activity. Thus, the invention also relates to methods for prevention or treatment of HIV infection by administering therapeutically effective amounts of a compound of formula (I), or a pharmaceutically acceptable salt or solvate thereof to a subject in need of such treatment.

  该发明涉及公式（I）的17ß鲁潘衍生物，其中R1和X如本文所定义，以及其药学上可接受的盐和溶剂化合物。这些化合物表现出显著的抗HIV活性。因此，该发明还涉及通过向需要此类治疗的受试者施用公式（I）的化合物或其药学上可接受的盐或溶剂化合物的治疗有效量来预防或治疗HIV感染的方法。