胍-13C盐酸 | 286013-04-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 胍-13C盐酸
• 中文别名: 胍-13C盐酸盐
• 英文名称: (13C)-guanidine hydrochloride
• 英文别名: Guanidine-13C hydrochloride；(13C)guanidine;hydrochloride
• CAS: 286013-04-5
• 化学式: CH₅N₃*ClH
• 分子量: 96.5207
• InChiKey: PJJJBBJSCAKJQF-YTBWXGASSA-N

物化性质

• 熔点：
  185-189 °C (lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.74
• 重原子数：
  5
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.9
• 氢给体数：
  4
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36
• 危险类别码：
  R20/21/22
• WGK Germany：
  3

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Guanidine-13C hydrochloride
CAS-No. : 286013-04-5
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]
Acute toxicity, Oral (Category 4)
Skin irritation (Category 2)
Eye irritation (Category 2)
Not a hazardous substance or mixture according to EC-directives 67/548/EEC or 1999/45/EC.
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.
H319 Causes serious eye irritation.
Precautionary statement(s)
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
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : 13CH5N3 · HCl
Molecular Weight : 96,52 g/mol

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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
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
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
no data available
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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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. 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.

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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.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Store under inert gas. hygroscopic
Recommended storage temperature: -20 °C
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
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
Safety glasses with side-shields conforming to EN166 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).

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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: 185 - 189 °C - lit.
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) 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: -1,700
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
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
LD50 Oral - rat - 1.120 mg/kg
LC50 Inhalation - rat - 4,00 h - 5,3 mg/l
LD50 Intraperitoneal - mouse - 500 mg/kg
no data available
Skin corrosion/irritation
Skin - rabbit - Skin irritation
Serious eye damage/eye irritation
Eyes - rabbit - Irritating to eyes.
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
Not mutagenic in Ames Test.
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
no data available
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
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
Toxicity to fish LC50 - Leuciscus idus (Golden orfe)
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
Offer surplus and non-recyclable solutions to a licensed disposal company. 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.

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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

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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：

  胍-13C盐酸 、 dimethyl (1R,4S,5R,8S)-4,8-bis[(3,5-didecoxyphenyl)methyl]-2,6-dihydroxybicyclo[3.3.1]nona-2,6-diene-3,7-dicarboxylate 在 potassium tert-butylate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以65%的产率得到
  参考文献：
  名称：

  A Remarkably Complex Supramolecular Hydrogen-Bonded Decameric Capsule Formed from an Enantiopure C₂-Symmetric Monomer by Solvent-Responsive Aggregation

  摘要：

  The formation of an unprecedented decameric capsule in carbon disulfide, held together by the combination of double and triple hydrogen bonds between isocytosine units embedded in an enantiomerically pure bicyclic framework is reported. The aggregation occurs via symmetry breaking of the enantiopure intrinsically C-2-symmetric monomer brought about by solvent, induced tautomerization of the hydrogen-bonding unit. We show that the topology of the aggregate is responsive to the solvent in which the assembly takes place. In this study we demonstrate that in carbon disulfide the chiral decameric cavity aggregate consisting of three forms of the same monomer, differing in their hydrogen bonding to each other is selectively formed, representing a tube-like structure capped with two C-2-symmetric monomers. The large cylindrical cavity produced selectively accommodates one partially solvated C-60 molecule, and molecular dynamic simulations revealed the special role of the solvent in the inclusion mechanism. The strategy described herein represents the first step toward the creation of a new class of hydrogen-bonded tubular objects from only one small symmetric building block by solvent-responsive aggregation.

  DOI：

  10.1021/jacs.5b03160
• 作为产物：
  描述：

  trichloro[13C]methyl phenyl sulfide 在 氨 、 盐酸 、 水 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 72.5h， 以47%的产率得到胍-13C盐酸
  参考文献：
  名称：

  SINGLE CARBON PRECURSOR SYNTHONS

  摘要：

  [13 C]甲基苯基硫化物的化学性质被利用来生产新的同位素标记前体，这些前体允许从简单且相对便宜的起始材料轻松组装出各种标记分子。这些化合物适用于诸如量子计算、代谢和材料科学等多种研究领域。

  公开号：

  US20080255370A1

文献信息

• Development of a Green and Sustainable Manufacturing Process for Gefapixant Citrate (MK-7264) Part 3: Development of a One-Pot Formylation–Cyclization Sequence to the Diaminopyrimidine Core
  作者：Kallol Basu、Dan Lehnherr、Gary E. Martin、Richard A. Desmond、Yu-hong Lam、Feng Peng、John Y. L. Chung、Rebecca A. Arvary、Michael A. Zompa、Si-Wei Zhang、Jinchu Liu、Zachary E. X. Dance、Patrick Larpent、Ryan D. Cohen、Francisco J. Guzman、Nicholas J. Rogus、Michael J. Di Maso、Hong Ren、Kevin M. Maloney

  DOI：10.1021/acs.oprd.0c00246

  日期：2020.11.20

  robust, and efficient manufacturing route for the synthesis of diaminopyrimidine 1, a key intermediate to gefapixant citrate (MK-7264), is described. A full mechanistic understanding of the cyclization step in the presence of guanidine was established by performing isotopic labeling experiments and identification of impurities. Guided by the mechanistic understanding, further attempts to modify the cyclization

  描述了开发安全，可靠和高效的生产路线的方法，以合成柠檬酸吉法pixant（MK-7264）的关键中间体二氨基嘧啶1。通过进行同位素标记实验和鉴定杂质，建立了在胍存在下环化步骤的完整机理的认识。在机械理解的指导下，还将提出通过使用添加剂减少三嗪（9）形成和胍负载量来修饰环化反应的进一步尝试。这种新开发的方法可提供化合物1 以商业规模获得88-94％的收率，并解决了早期合成路线的缺点，包括高PMI，低原子经济性，长循环时间和多次纯化以达到所需质量。
• Synthesis of [¹³C₄]Baraclude^®(entecavir)
  作者：Scott B. Tran、Ihoezo V. Ekhato、J. Kent Rinehart

  DOI：10.1002/jlcr.1664

  日期：2009.9.15

  Entecavir, labeled as 1H-[13C4]purin-6(9H)-one, was prepared from commercially available [13C]guanidine HCl, 1 and diethyl [1,2,3-13C3]malonate, 2. The reagents were condensed together to give 2-amino-4,6-dichloro[2,4,5,6-13C4]pyrimidine 3, which in turn was coupled to an optically active amino cyclopentanol derivative, 9. A further sequence of eight reaction steps completed the constructions of the purine ring system and the exocyclic olefin attachment on the cyclic pentyl portion, 18. The removal of the methoxide and benzyl protecting groups gave [13C4]entecavir, 20 in an overall yield of 6.8%. The chemical purity of the title compound was determined by HPLC to be 99.23%. The percent isotopic [13C4] abundance was found by mass spectral analysis to be 96.7%. No detectable level of the unlabeled entecavir was found by LC-MS analysis. Copyright © 2009 John Wiley & Sons, Ltd.

  恩替卡韦以市售的[13C]盐酸胍1和[1,2,3-13C3]丙二酸二乙酯2为原料制备出标记为1H-[13C4]嘌呤-6(9H)-酮的恩替卡韦。将这些试剂缩合在一起可得到2-氨基-4,6-二氯[2,4,5,6-13C4]嘧啶3，再将其与具有光学活性的氨基环戊醇衍生物9偶联。接下来的八个反应步骤完成了嘌呤环系统的构建和环戊基部分的外环烯烃连接，即 18。去除甲氧基和苄基保护基团后，得到[13C4]恩替卡韦 20，总产率为 6.8%。经 HPLC 测定，标题化合物的化学纯度为 99.23%。质谱分析发现，[13C4] 同位素丰度为 96.7%。通过 LC-MS 分析，没有发现未标记的恩替卡韦。Copyright © 2009 John Wiley & Sons, Ltd. All Rights Reserved.