1-苯基双胍 盐酸盐 | 55-57-2

• 物质功能分类: 化学试剂 - 有机试剂 - 胍盐
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 1-苯基双胍 盐酸盐
• 中文别名: 1-苯基双胍盐酸盐
• 英文名称: 1-phenylbiguanide monohydrochloride
• 英文别名: phenylbiguanide hydrochloride；1-phenylbiguanide hydrochloride；N-phenylbiguanide hydrochloride；1-carbamimidamido-N-phenyl methanimidamide hydrochloride；[N'-(N'-phenylcarbamimidoyl)carbamimidoyl]azanium;chloride
• CAS: 55-57-2
• 化学式: C₈H₁₂N₅*Cl
• mdl: MFCD00035040
• 分子量: 213.67
• InChiKey: FHUDRDSKZQDCBC-UHFFFAOYSA-N

物化性质

• 熔点：
  244-247 °C(lit.)
• 溶解度：
  可溶于DMSO（轻微超声处理）、水（轻微超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  0.73
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103
• 氢给体数：
  4
• 氢受体数：
  1

安全信息

• WGK Germany：
  3
• 储存条件：
  存储于室温下

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 1-Phenylbiguanide hydrochloride
CAS-No. : 55-57-2
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)
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.
Precautionary statement(s) none
Supplemental Hazard none
Statements
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C8H11N5 · HCl
Molecular Weight : 213,67 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
Flush eyes with water as a precaution.
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
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), Hydrogen chloride gas
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.Normal measures for preventive fire
protection.
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
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: powder
Colour: white
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 244 - 247 °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- 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
no data available
Incompatible materials
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
LD50 Oral - mouse - 1.200 mg/kg
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
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. May cause respiratory tract irritation.
Ingestion Harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes
May cause 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: DU2550000

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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
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material. 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
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.

反应信息

• 作为反应物：
  描述：

  1-苯基双胍 盐酸盐 在 Lindlar's catalyst 、 乙醇 、 sodium methylate 作用下， 生成 6-甲基-N-苯基-1,3,5-三嗪-2,4-二胺
  参考文献：
  名称：

  Monomer Synthesis.¹ Triazines. A Novel Method for the Reduction of Halomethyl Groups in the Triazine Series

  摘要：

  DOI：

  10.1021/ja01630a026
• 作为产物：
  描述：

  aniline hydrochloride 、 二聚氰胺 在 乙醇 作用下， 生成 1-苯基双胍 盐酸盐
  参考文献：
  名称：

  Smolka; Friedreich, Monatshefte fur Chemie, 1888, vol. 9, p. 230

  摘要：

  DOI：

文献信息

• Synthesis and in vitro anticancer evaluation of some 4,6-diamino-1,3,5-triazine-2-carbohydrazides as Rad6 ubiquitin conjugating enzyme inhibitors
  作者：Hend Kothayer、Sebastian M. Spencer、Kaushlendra Tripathi、Andrew D. Westwell、Komaraiah Palle

  DOI：10.1016/j.bmcl.2016.02.085

  日期：2016.4

  abbreviate our compound names as 'new triazines', have been synthesized, based on the previously reported Rad6B-inhibitory diamino-triazinylmethyl benzoate anticancer agents TZ9 and 4-amino-N'-phenyl-6-(arylamino)-1,3,5-triazine-2-carbohydrazides. Synthesis of the target compounds was readily accomplished in two steps from either bis-aryl/aryl biguanides via reaction of phenylhydrazine or hydrazinehydrate

  4-氨基-6-（芳基氨基）-1,3,5-三嗪-2-碳酰肼（3a-e）和N'-苯基-4,6-双（芳基氨基）-1,3,5-三嗪系列为方便读者阅读，我们合成了-2-碳酰肼（6a-e），根据先前报道的Rad6B抑制性二氨基三嗪基甲基苯甲酸酯苯甲酸酯类抗癌剂TZ9和4-氨基合成了我们的化合物名称“新三嗪”。 -N′-苯基-6-（芳基氨基）-1,3,5-三嗪-2-碳酰肼。通过苯肼或肼与关键的4-氨基-6-双（芳基氨基）/（芳基氨基）-1,3,5-三嗪- 2-羧酸盐中间体。评估了这些新的三嗪衍生物抑制Rad6B泛素结合的能力以及针对几种人类癌细胞系的体外抗癌活性：卵巢癌（OV90和A2780），肺部（H1299和A549），乳腺（MCF-7和MDA-MB231） MTS分析检测结肠癌和结肠癌（HT29）细胞。与先前报道的选择性Rad6抑制剂TZ9相比，所有10种新的三嗪均表现出优异的Rad6B抑制活性。
• Discovery of Small-Molecule Cyclic GMP-AMP Synthase Inhibitors
  作者：Rosaura Padilla-Salinas、Lijun Sun、Rachel Anderson、Xikang Yang、Shuting Zhang、Zhijian J. Chen、Hang Yin

  DOI：10.1021/acs.joc.9b02666

  日期：2020.2.7

  exists for inhibiting cGAS in cells, while others are limited by their poor cellular activity or specificity, which underscores the urgency for discovering new cGAS inhibitors. Here, we describe the development of new small-molecule human cGAS (hcGAS) inhibitors (80 compounds synthesized) with high binding affinity in vitro and cellular activity. Our studies show CU-32 and CU-76 selectively inhibit the DNA

  环鸟苷单磷酸腺苷单磷酸（GMP-AMP）（cGAS）是一种胞质DNA传感器，在I型干扰素应答中起着重要作用。来自入侵微生物或自身来源的DNA触发cGAS的酶促活性。cGAS的异常激活与各种自身免疫性疾病有关。仅存在一种抑制细胞中cGAS的选择性探针，而另一些选择性探针由于其细胞活性或特异性差而受到限制，这突显了发现新的cGAS抑制剂的紧迫性。在这里，我们描述了具有高结合亲和力的体外和细胞活性的新型小分子人cGAS（hcGAS）抑制剂（合成的80种化合物）的开发。我们的研究表明CU-32和CU-76选择性抑制人细胞中的DNA途径，但对RIG-I-MAVS或Toll样受体途径没有影响。
• Biguanide Iridium(III) Complexes with Potent Antimicrobial Activity
  作者：Feng Chen、John Moat、Daniel McFeely、Guy Clarkson、Ian J. Hands-Portman、Jessica P. Furner-Pardoe、Freya Harrison、Christopher G. Dowson、Peter J. Sadler

  DOI：10.1021/acs.jmedchem.8b00906

  日期：2018.8.23

  We have synthesized novel organoiridium(III) antimicrobial complexes containing a chelated biguanide, including the antidiabetic drug metformin. These 16- and 18-electron complexes were characterized by NMR, ESI-MS, elemental analysis, and X-ray crystallography. Several of these complexes exhibit potent activity against Gram-negative bacteria and Gram-positive bacteria (including methicillin-resistant

  我们合成了包含螯合双胍的新型有机铱（III）抗菌复合物，包括抗糖尿病药物二甲双胍。这些16和18电子络合物通过NMR，ESI-MS，元素分析和X射线晶体学表征。这些复合物中的几种显示出对革兰氏阴性菌和革兰氏阳性菌（包括耐甲氧西林的金黄色葡萄球菌（MRSA））的有效活性，并且对白色念珠菌和新形成梭菌具有很高的抗真菌效力。，最低抑制浓度（MIC）在纳摩尔范围内。重要的是，该复合物对哺乳动物细胞显示出低细胞毒性，表明高选择性。它们在肉汤培养基中高度稳定，很少产生抗药性突变。共同给药时，它们可以恢复万古霉素对耐万古霉素肠球菌（VRE）的活性。此外，复合物还可以破坏和根除成熟生物膜中的细菌。对与生物分子反应的研究表明，这些有机金属络合物将活性双胍类物质传递给微生物，而双胍类物质单独给药时本身是无活性的。
• AN EFFICIENT SYNTHESIS OF 1-ARYL-4,6-DIAMINO-1,2-DIHYDRO- 1,3,5-TRIAZINES
  作者：Neungruthai Saesaengseerung、Tirayut Vilaivan、Yodhathai Thebtaranonth

  DOI：10.1081/scc-120005415

  日期：2002.1.1

  ABSTRACT 1-Aryl-4,6-diamino-1,2-dihydro-1,3,5-triazines bearing diverse substituents at C2 and on the aromatic ring have been synthesized in good yield from an acid-catalyzed reaction between corresponding arylbiguanide and carbonyl compound in the presence of triethyl orthoacetate as a water scavenger.

  摘要 1-Aryl-4,6-diamino-1,2-dihydro-1,3,5-triazines 在 C2 和芳环上具有不同的取代基，通过相应的芳基双胍和芳环之间的酸催化反应合成，收率良好。在作为水清除剂的原乙酸三乙酯存在下羰基化合物。
• Reactions of triacetylmethane with monosubstituted hydrazines and amidine analogues. Syntheses of 4-acetyl-3,5-dimethylpyrazole amidinohydrazone and 1,3,5-triazine derivatives
  作者：Kaname Takagi、Abdelilah Bajnati、Michel Hubert-Habart

  DOI：10.1002/jhet.5570270608

  日期：1990.9

  Triacetylmethane (1) reacts with amidinohydrazines in acidic medium to afford 4-acetyl-3,5-dimethylpyrazole amidinohydrazone derivatives 2,4. However, a similar reaction of 1 with thiosemicarbazide or semicarbazide led mainly to 3,5-dimethylpyrazole (6). The great propensity of 1 to hydrolysis accounts for this last transformation, as well as for the fact that with guanidine it led to 2-amino-4,6-dimethylpyrimidine

  三乙酰甲烷（1）与a肼在酸性介质中反应，得到4-乙酰基3,5-二甲基吡唑a衍生物2,4。然而，1与硫代氨基脲或氨基脲的相似反应主要导致3,5-二甲基吡唑（6）。1的水解趋势很强，这是最后一个转化的原因，也是由于胍导致了2-氨基-4,6-二甲基嘧啶（10）和S-甲基异硫脲提供了出乎意料的2-氨基-的事实。 4-甲基-6-甲硫基1,3,5-三嗪（11）。